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KB and Me

True story, if it had been fantasy, it would have ended much differently First time writer, so please be gentle.

Avatar : The Legend of Korra and the Immortal Avatar

I’m not sure whetere or not I should continue this story due to it not being particularly suited to this type of website and I will leave it to the readers as to bth continue it and eventually add a sex scene between Korra and Raiden or not. This is the order time if have written something that has been posted for ratings and criticism. Any Tips on how to improve would be appreciated

MY DAUGHTE IS A CUM DUMPSTE 3

I would like to apologize for the delay in continuing this story. I have received a series of requests to continue it and I am humbled that my perverse thoughts and writing style appeal to so many. It’s tough times and working two jobs while keeping this hobby quiet has proven difficult. But without further delay, here is the next chapter of my first ever publication.
I was rarely the first to rise, but I was feeling rather relieved by the prior days activity. My daughter was turning into every pervert’s wet dream and my wife was none the wiser. Part of me, the very small portion of integrity and self-respect that remained had made an un-negotiable promise. I swore to myself that I would not have sex with Renee. It’s not because I did not want to, but I felt that there is a limit to any perverse thought. I felt at this moment, my limit was the absolute refusal to take her virginity.
I walked into the bathroom and started the water to the shower. As the room began to steam, I undressed and stepped inside. My dick has been steadily hard for two solid days. Part of me chuckled as I thought of a stupid Viagra commercial and the recommendation to see a doctor if it lasts more than four hours. I lathered up my cock and balls and got a crazy thought. It had been about a year since I last did some manscaping. A perverted smile came across my face as I picked up my razor.
Although it had been awhile since I last shaved my balls, I was able to get the job done like a seasoned pro. I shaved them clean as a whistle and trimmed my pubes into a thin triangle. I even ventured the razor into my crack and did the best I could to shave around my asshole and gooch. I even thought about going to a distant salon and considered a wax. But that is not a serious consideration. I fear the embarrassment and pain declined that mental option.
As I stepped out of the shower to dry off I was feeling rather sexy for the first time in a long time. I strutted back into the bedroom with my wood and new trim on proud display. Stacey was still sleeping as I walked up to the bed. I was thinking of a fun way to wake her up to show off my new toy. As I approached my bed I noticed my phone was blinking. Knowing I had a new text and it was probably from Renee I anxiously picked up my phone right as Stacey began to stir.
Before I could open the message I heard “mmmmm is that for me big boy…?” from Stacey in her sexy but not really awake voice. In truth I did think much about Stacey when I did it, but I had no problem with her enjoying it. Stacey reached out and grabbed my cock with her hand and gave it a few short tugs as I stared down at her. I hadn’t forgotten my phone in my hand and I didn’t want to make any obvious way of hiding it. Fortunately I didn’t have to. Noticing the phone in my hand she said “someone is feeling naughty this morning… But honey I look terrible. Let’s not take any photo’s right now. Let me go pee then I will take care of my little friend here.” With that said she leans forward and briefly licked the head of my dick and trotted into the bathroom. She slapped my bare ass as she passed by.
Although I was excited to get some, I was sadly more excited to see what my daughter had sent me. I quickly turned on the screen of my phone and smiled when I noticed I had gotten three new messages but only one was from Renee. The others were from work friends, I would check them later. I had only one that peeked my interest.
I opened the message and involuntarily grunted when I opened the picture message. It was a photo of Renee’s sweet hairless pussy with the newly acquired dildo plunged to the fake balls inside. The photo was not of high quality but it was still the hottest photo I had ever seen. My dick was literally bouncing with excitement and if I hadn’t had so many orgasms the past couple days then I could have ejected my trembling squirming juniors from my steel hardened prick. My manhood was nothing to be particularly proud of, but with the new manscape and its particular hardness I was strutting around like a peacock knowing two women in my own house wanted it. I use the term “woman” loosely when im referring to Renee. She will be starting High School in August and I reserve that descriptive term for later in her development. As of now she is just a crazy young girl who has educated herself well on the kinkiest of all foreplay and sex via internet pornography.
Just then Stacey walked out of the bathroom with a grin and a skip towards me. She was wearing only a bra and a smile. She shuffled up to me and planted a strong kiss on me. “We don’t have long because I have work, so nut quickly okay?’’ she said as she grabbed my cock and pulled me towards the bed like a leash.
Stacey sat on the bed and gave my prick three deep plunges in her mouth to get it lubricated. I was so aroused I knew busting a nut quickly would be easy. Stacey bent over the bed and looked over her shoulder at me with her “fuck me” eyes and said “If you dump your load quickly I will bring you home some ice cream”… It’s odd that it was just then I realized how much she really knew me. She knew motivating me with food in a form of dirty talk would get the results she wanted.
Without delay I entered her and sunk my dick to the hilt. She screamed out in delight “Oh yeah Daddy YEAH” as I began my thrusting. Hearing her say that placed Renee right in my thoughts. I immediately pictured Renee replacing Stacey on the bed. Her smaller/shorter stature getting jolted by my thrusts. At that moment I felt the upcoming orgasm hit me hard and my knees buckled as I thrusted as hard as I could. I felt every last drop of my swimmers dive into the depths of her sopping pussy.
I backed out of her quickly with a loud sloppy flop. I always liked doing that so I could watch my cum spew from her womb. As I observed the leak I smiled from ear to ear and took a seat on the bed next to her. I gasped my breath while she lay there for a moment. She slowly stood up and waddled back to the bathroom while my spunk slid down her legs. It’s odd, but I find that sight extremely erotic.
I fell back on my bed and grabbed my phone thinking Renee may have sent me a message. Sadly she hadn’t. I stood up and got dressed in some pajama pants. The ones with an opening fly, and I pulled on a t-shirt. As Stacey scurried out of the bathroom towards the bedroom door I followed her. She needed to leave right away if she was going to make it to work on time. Her hours really are awful.
As we walked through the living room to the kitchen I was stunned to see Renee sitting at the breakfast bar. She was sitting on a stool in an outfit I feel was straight out of a stripper supply store. She was wearing the classic schoolgirl outfit. From the toes up she wore knee high white socks, a black and red plaid skirt that draped over the stool, and a white tank top without a bra highlighting her clearly erect nipples and small breasts. She even polished the outfit off with pigtails and a ribbon. It was the sexiest outfit I had ever seen. It was obvious that she was intentionally dressed like a slut and the truth is… I absolutely fucking loved it. The problem is, there is no way Stacey was not going to notice as well. Trouble was brewing.
Renee was sitting there eating a bowl of cereal as Stacey stomped into the kitchen collecting her things from the countertops stuffing them into her purse. Renee was staring at me with almost teary eyes. They were not eyes of sadness, but more of an anxious yearning. Her face appeared sweaty and her hairline was damp.
Stacey approached Renee and kissed her on top of her head. “Have a good day at school sweetie… please get some laundry done tonight.” Stacey said to Renee. Stacey then approached me and gave me a peck on the mouth. She whispered “later stud” and gave me a small squeeze on my butt. Stacey then scrambled out the front door. I couldn’t believe Stacey didn’t say or appear to notice Renee’s outfit.
I approached Renee who brightened the room with a huge smile as I approached. “Good morning daddy…” she spoke in her most innocent voice. “I’ve been waiting for you… I’m having SOOOO much fun with my new toy. Thank you again daddy I absolutely love iiiiiiiit” she said trailing off at the end.
I was puzzled by her behavior as I sat in the stool next to her. Renee then sat up straight and started shifting her hips forward and backwards violently. She arched her back and let out a loud cry and displayed every symptom of an orgasm. I saw a flood of liquid drip down the legs of the stool she sat on. I couldn’t believe my eyes. She literally just had an orgasm on the stool without doing anything. Renee started breathing more casually and sighed in in obvious relief. She turned and looked at me with a blushing smile on her face. “I really needed that…” she said as she collected her composure.
She obviously noticed my puzzled face. She said “I have to go to school soon… and this cereal is not what I want to eat.” Renee slowly and shakily started rising off the stool until she was almost standing on the stool pegs. Renee swung her leg off the stool and stood next to the stool. I choked when I noticed the source of her behavior. The dildo I gave her the day prior was standing erect on the stool. She had been sitting on the stool with the dildo plunged into her pussy the whole time.
I was so fucking turned on by this that I reached down and unbuttoned the fly of my pajama pants. Catching my drift, Renee jumped to me and reached into the fly tugging my cock out almost violently. Renee gasped when she realized my newly shaven ball sack. She instantly attacked them orally and sucked a nut into her mouth with a slurping sound. “Daddy?” she mumbled. “Yes sweetheart” I said with my head arched back. “You just fucked mommy didn’t you… I can taste her.” She said as she took the head into her mouth. I didn’t exactly know how to respond, and I didn’t want to lie so I nodded in a yes. Renee pulled my dick from her mouth and said with an almost pouty tone “it tastes good. Do you want to fuck me now too?” This was that moment that I was preparing myself for. As badly as I wanted to take her… I still could not take her virginity. It was just too wrong I convinced myself.
“I just cant do that to you sweetheart…” I said with less conviction than I wanted. “But daddy… why not… Im your slut…” she replied after pulling her mouth free momentarily. As erotic as this moment was, I still was not budging on my decision and I said the only honest answer I could think of. “Sweetheart… I love you and I love what your doing to me… But I cant take your virginity… It’s just too far.” I immediately regretted my words the moment they left my mouth. I was just praying my cock would not leave hers.
“I gave my virginity to my new toy right there… I named it DADDY” she said pulling away and steadily stoking my knob. I was approaching an orgasm. I really just want to push her to the ground and ravish her. She let go of my cock and stood up. I was devastated that she let me go. Was this the end?… I really fucked up this time.
Renee grabbed “DADDY” from the stool with a pop. She retuned between my legs and set the dildo on the linoleum floor between my feet. Renee hiked up her skirt with her left hand and spit a long string of saliva into her right hand. She used the spit soaked palm to wipe her bare pussy. Renee then lowered herself onto the dildo and I watched as the head penetrated her womb. She used slow rocking motions to slowly ease herself onto the toy. With a groaning sigh Renee said “that’s better. I’m gonna fuck my daddy one way or another.” Renee then leaned forward and hands free lifted me into her mouth. She leaned forward as far as she could before she gagged. Determined she kept it in as long as she could before she pulled back gagging again. She looked into my eyes as her eyes began to well and her face flushed from the continuous choking and pleasure in her pussy.
“Daddy listen to me…” Renee said with a serious stern face and voice. “You can do anything… ANYTHING… you want to me… I want to try everything there is… I’m you toy.” My mind went to a dark place at this moment. Getting a green light to explore every sour thought I ever imagined guilt free prompted an evil chuckle. That statement changed my life.
“Stand up slut!” I barked, giving into my deepest awful thoughts. Visibly surprised by my changed demeanor Renee jumped to attention with a confused look. I grabbed Renee around the waist and picked her up to my chest. I planted our faces together and buried my tongue as far into her mouth as I could. She let out a moan as I did this. A THUD rang through the kitchen as I dropped her onto her ass on the kitchen bar. I put my hand over her face and pushed her hand causing her upper body to fall back on the bar. I dropped to my knees and took in my first close up of her perfect bare pussy. I did not waste any time before I went to town with my mouth. I pulled out all my learned skills. I licked her clit, I tongued her hole. Hell, I even tongued her tiny asshole. Renee bucked and squired all over the countertop as I applied my talent. I knew she was going to bust any moment. She was screaming and moaning “Daddy…Oh Daddy!!!”… I used my hand to stimulate her clit and opened my mouth around her opening. One last ear shattering scream caused the flood gates to open and a river of fluid shot from her pussy with more force than I expected. I was without a doubt completely drenched from head to shoulders. As she subsided her orgasm I stood up with a bulging mouth of pussy squirt. I reached over and grabbed Renee by a pig tail and sat her up. I cupped her neck/chin with my hand and angled her face upwards. Renee understood what I wanted and opened her mouth. I leaked her fluid from my mouth into her mouth small amounts at a time. She graciously swallowed every drop I provided her. After the last drop was drunk, I pushed her back onto the bar. I removed my pants and walked around to her face and dropped my balls onto her nose. Without hesitation she opened her mouth and allowed my aching balls into her mouth. She lathered them softly and gently. Without intention I stumbled forward a step and my balls fell onto her neck.
I felt a sensation I had never felt before. Renee without missing a beat, starting licking my asshole. I jumped at first but the new feeling was… fantastic. My dick was throbbing at the new pleasure. I backed up and dropped my cock into her mouth. I was possessed and did not control myself. I began thrusting without giving her the opportunity to lube and adjust to the new activity.
Renee was gagging and gargling but I did not stop. I pumped as much as I could before hitting the wall of her throat. I didn’t want to kill her, but I did want her to understand what I wanted my “toy” to do. I felt my orgasm bulging in my groin Renee obviously sensed this and acted in a way that I again had never experienced before. Renee forced her middle finger into my asshole and pressed forward towards my cock. The sensation at first was surprising and made me jolt. But I unloaded the largest flood of semen I have ever seen. Renee used her free hand to stroke my cock as her mouth waited open underneath. By the time my unearthly orgasm subsided her mouth was filled to the brim with hot frothy cum. I took a step back and Renee released her finger from my ass. She stared at me upside down and closed he mouth. She rolled to her stomach while maintaining eye contact. She gulped hard. I could see her straining and forcing herself not to gag. Her eyes were watery as she opened her mouth and displayed an empty oral cavity.
“Did I do good daddy?” she said with her sweet upbeat personality. She smiled and giggled a little. “That was very good baby girl… very, very, very good.” I said before walking to the bar and sitting on the stool. “Now, go clean yourself off and get to school…” I said with a slightly more authority tone.
With a pouty face Renee left to her room. About 30 minutes later she came back downstairs in slightly more appropriate school clothing. I met her at the front door and gave her a kiss. Her pouty attitude instantly changed as we began making out. I was hunched over so far to reach her face that I think I could have touched the ground. As I released her and stood up she bit her lower lip and gave me her best “fuck me” face. I pulled out my wallet and gave Renee my credit card. Surprised and confused she took it from my hand. “I think you should be able to order whatever toys you want… Just don’t get too carried away. And a little something for me wouldn’t hurt either.” Renee instantly leaped into my arms and planted a wet kiss on my face. We kissed for about a minute before I heard the school bus honk. We both jumped at the sound and I sat her back onto her feet. With a giant gin on her face Renee opened the door and ran to the bus.
Unfortunately I was leaving for work tomorrow. I am a roofing consultant and I have a three day job that I leave for tomorrow morning. Hopefully I can handle going more than 45 minutes without a spooge release. I walked over to the couch and took a seat. The smell of young pussy filled the house. I was in bliss for this moment.

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Experimentation Vol 3

Experimentation Volume 3
Happiness filled my life in a way it never had before. No one had ever thought to treat me the way Mistress did every day. I was her slave; she owned me, yet Mistress often brought me breakfast in bed! She continued with my reading lessons, and I continued with her sex lessons. It was probably a result of the circumstances, but for the first time in my life, I realized that I was falling in love. Love was something that I’d never known, and I didn’t really know how to respond to it. The strange thing was that the situation was mutual; Mistress began to fall for me, and she didn’t really know what to do about it either. Mistress began to give me an allowance, in the fashion parents did with their offspring. I got fifty dollars a week, in cash; fifty dollars that I could spend on little luxuries for myself.
When Mistress took me home, on the first day, she told me that there was one wardrobe in the bedroom that was out of bounds for me. I wondered what was in it; in fact I was desperately curious to find out its contents, but I left it alone. It was two months until Mistress gave me permission to open the wardrobe, and I was quite surprised to see the contents. They weren’t exactly things a young lady was expected to keep in her bedroom. That wardrobe contained almost two dozen swords from around the world. I was immediately fascinated with the collection, and asked Mistress to teach me all about swords, and the cultures that created them.
After almost four months of mutual sexual pleasure with Mistress’, it was my thirty-third birthday, and on the morning of that day, Mistress gave me the first birthday card I’d ever received. The wording from Mistress was, ‘For my Princess; my companion and my friend. All my love, Mistress.’ Inside the card was a smaller envelope with no markings. I opened the envelope to find hundred dollar bills; ten of them, and I found myself speechless. No one had ever given me a noticeable amount of money before, and told me I spend it on whatever I liked. My first thought was to save my present and hope that Mistress gave me many more such presents. That way, I was sure I would be able to buy my sister’s freedom. Perhaps I could even buy my own eventually. Of course, being a slave meant that I couldn’t have a bank account to save the money in, so I asked Mistress if she would open an account for me, so that I could save my money easily. Naturally, she agreed, and I got my savings account in Mistress’ name. Then, whatever out of my allowance I didn’t spend, I saved for the future.
My first problem, of course, was that I had to find my sister. I didn’t know where she was, so I was obviously going to have considerable work ahead of me. However, she was my sister, and I wanted to help her.
My first thought was to ask my parents if they knew where my sister was. If I was lucky, she would still be where they were, and hopefully would stay there until I could save up enough money and try to convince her owner to sell her to Mistress. Again, being a slave meant that I could not have property, but if I gave Mistress the money, she could buy my sister, and free her for me. I would pay every dollar of her asking price, and more, if Mistress would do what I wanted. I knew that my father was able to read and write, so I typed a letter on Mistress’ computer, bought a book of stamps the next time Mistress asked me to go shopping, and sent it to my father, along with a supply of envelopes, paper, stamps and pens; just hoping he’d get the package. My luck was in, and my father received it. He replied to me, in considerable surprise at my literacy, and gave me some bad news. My sister had been sold a couple of years earlier, but he could give me the address of her owner, and he confirmed that she also could read and write, so would be able to reply to any letters she received, if she received them.
When I got the reply from my father, Mistress handed me the envelope with a smile on her face. “Never had post before, Princess?” she asked. I almost took Mistress’ fingers off, when I snatched the envelope from her hand and ripped it open. It was a fabulous feeling, reading my first ever letter, although the feeling didn’t last when I read the news it contained. It was clear to Mistress that I was upset, so she put an arm around my waist, and kissed me. “Need a new letter pack then, Princess?” she asked.
“Yes Mistress; I just hope she’ll be able to answer,” I replied.
Mistress supplied me with my pack of stationary and stamps and I wrote to my sister. She was every bit as surprised as my father at my newfound ability to write. She was an administrator, which required her to be literate, and she asked me what I did for my owner. What did I tell her? I asked Mistress for her opinion and she said that I should describe myself as a ‘domestic.’ All of what I did for Mistress would be classified as ‘domestic’ work, in as much as it was done inside her apartment. As long as my sister remained in her position, she was safe, and I could be content with knowing that, until the time arrived that I could try to free her from her life of slavery.
She and I traded letters intensively for months, and I kept her well supplied with letter writing materials, at Mistress’ expense. In that time, Christmas came and went, and the contents of my savings account tripled to more than three thousand dollars, and my bra increased by one cup size. I took Mistress by surprise by giving her a Christmas present bought from my allowance. I told my sister the story of my first trip to the fetish store with Mistress, and included the story of our second visit.
That was every bit as entertaining as the first time, and I could even read the writing on the products. Mistress had decided that she required a larger dildo for me to make love to her with. I knew we were going shopping, the way we usually did, but she didn’t have to tell me where we were going. The spiked collar around Mistress’ neck indicated that we were going to the fetish shop, and that I was again going to have to pretend to be Mistress’ owner.
As instructed by Mistress, I clipped on her leash just after we got out of the car, and I led her by it into the store. The response was much as predicted. “Hey, look who’s come back. It’s the lucky bitch with the fantastic bit of pussy! Are your tits bigger than the last time you were here?”
“Yes, I’ve been under the knife.”
“Thought so. You broke the little bit of pussy in properly, after you took her home, last time?”
“Given the price I paid for her, you’re damn straight I did! She’s a wonderful fuck, with such a lovely tight pussy. There are times I wonder how it might feel to be a man, and whenever I’d got my double-ended rubber prick buried clit-deep in her pussy, I do think like that. What would it feel like to be able to spunk in her cunt daily, I wonder? With tits like those to squeeze, I fuck her several times a day when I have the energy!” I had to laugh dirtily, like a letch, as I spoke; it was expected of me.
You gonna tell me what you paid for her, yet?”
“Due to favourable circumstances, I got her for the bargain price of thirty five grand!” I replied; even managing to sound as if I was gloating over my purchase. I suppose that if I had been in that position, I may well have gloated over what I’d gotten, at the price I supposedly got it for.
“Thirty five? Lucky cow! How did you achieve that feat?” I could sense the jealousy in her voice, and I was sure I could see it all over her face.
I pulled Mistress closer to me, and put my arms around her waist. “She’d been bought as a gift to her previous owner’s son, but for reasons unknown, he was still unable to get his prick solid enough to stick it in her. She was kept intact until he was going to be capable of fucking his present; he never got the chance. Financial trouble hit the family, and they needed money, fast. Coincidentally, I happened to hear about their troubles, and remembered the girl they’d bought for their son for when he overcame his limp prick problem, and made an offer for her. They needed a quick sale, and thirty five thousand in cash, was sufficient incentive for me to take ownership. I realize how lucky I was to get her so cheap, and I intend to take maximum advantage of that as often as I can.”
“I’d ask if you were willing to sell her to me, but in your place, I wouldn’t let that go any time soon either.”
“Not a chance, and you know it!”
“I can dream, can’t I?” She produced a business card, which she handed me, “In case you change your mind, or, however unlikely it is, eventually get bored with Miss. Tits, there. I’ll pay top dollar for her in either of those situations.”
I took the card, but I knew it wasn’t relevant; after all, I couldn’t sell what I didn’t own. Even if did own Mistress, I could never have sold her to the sort of pervert that room was full of; they wouldn’t have treated her the way I would have, and the way I already did. She treated me better than most, if not all, of the women in that room would have treated her. Some men didn’t treat their wives as well as Mistress treated her obedient, horny, blonde sex slave.
(For example, there was the time I’d come down with food poisoning. At the time, we didn’t know the cause of the condition, but I was ill; very much so. Mistress summoned a doctor to attend to me, and with the experiences I’d had, that was something I had not been expecting. No other owner had summoned a doctor for me, or for any other slave I’d ever known, yet Mistress didn’t bat an eyelid at the expense of the doctor, or the hospital visit she recommended. Mistress took me to A & E, and paid my bills. She even got all combative with the doctors who didn’t originally want to treat me because I had no medical history. It was beautifully done, and in a way I wouldn’t have dreamt of. Mistress told them that they had a responsibility to treat any sick person with the money to pay, and seeing as Mistress could pay for my treatment, they were obliged to treat me. She also threatened to sue the asses off them all if I didn’t survive the treatment. I was an expensive piece of property and she wanted me back in first class condition, ‘or fucking else!’ Mistress also commented that at home, she never restrained me, and if I complained about being chained up, or otherwise mistreated, there’d be absolute bloody hell to pay! She left me in hospital for three days, visiting twice a day on each of them, with flowers, chocolates and kisses. The bill for my treatment was half as much as my purchase price, yet Mistress paid it without hesitation because I was worth it! “It’s only money,” Mistress commented, when she signed the forms.)
During that visit, I was asked how I got such fine service from my girl. At first, no one there would believe that I’d never had to beat Mistress. I explained it very simply. “When I got her, she’d seen other slaves facing their punishments for infractions, and she knew what she could expect if she misbehaved. She didn’t misbehave, and at the end of the first week, I rewarded her with a shopping trip. That was before you first saw her, and before I first fucked her. I mastered treating a beautiful young woman, as what she was, and not mistreating her. I trained this one, with the carrot, rather than the stick, and it works. I get what I want, and I treat her like a lover! I give her fine clothes, and good food; and I make love her, making the experience as enjoyable for her as it is for me. And that, my new friends, is the way to get such service from a slave; it gives her an incentive to do what you want her to do. Give her treats and presents, and lots and lots of orgasms. She drives, too; she’s my chauffeur!”
******
When my reading and writing skills had reached high school standards, and after year and a bit, Mistress handed me an A4 envelope with the instruction to fill in the forms it contained. It was my application for a driving license. Everyone knew that slaves didn’t get to drive cars; it would just make it easier for them to escape from their owners. However, it wasn’t illegal to teach a slave to drive; it was just assumed that no owner would ever bother. I hadn’t expected that I would learn that skill either.
It took me a while, but I actually learned to drive, and was added to Mistress’ insurance policy. I had trouble with the local police on a couple of occasions, but Mistress got me out of trouble, and then, to avoid that sort of trouble, she bought me my own car. I got the car delivered on Mistress’ and my second anniversary. It had my name on its registration document. Mistress’ lawyer found a loophole in the property law, in that in the case of cars, the registered keeper isn’t necessarily the legal owner, which was why we got away with it. I knew nothing about the car until it got delivered, and I was asked to put my signature on the paperwork to confirm that it was mine. When Mistress told me that my car had arrived, I was stunned. When I saw it, I was even more stunned! I’d expected a little family compact, and when I laid eyes on a mint condition nineteen fifty seven Cadillac Eldorado convertible; all gleaming black pain, fins and chrome, I didn’t know what to do, or what to say. I didn’t even move to catch the keys, as Mistress threw them to me. She had to pick the keys up, put them in my right hand and wrap my fingers around them, before I seemed able to keep hold of them. Even then, I didn’t make any move towards the car until Mistress stood behind me and began to literally push me towards it. I saw the irony though; Mistress had given a five thousand dollar slave a car worth ten times her value; maybe more! I didn’t ask Mistress what she paid for the car; I just promised her that that I would be careful when I drove it.
When I finally got in the car, and Mistress had encouraged me to go out and burn some rubber, she also opened her purse and put her hand in it. I was surprised when she handed me a tazer and said, “Just in case some cunt tries to steal your nice new car.” Being a slave, I wasn’t allowed a gun, but the old laws had been written before the invention of the current generation of non-lethal defensive weapons, and the majority of them weren’t on the list of prohibited weapons for a slave. For example, Mace was a prohibited weapon for a slave, so Mistress gave me a can of corrosive oven cleaner instead. Nastier than Mace it might have been, but it was a domestic item, and therefore not illegal for a slave to have in her purse. Mistress’ lawyer eventually found a loophole in the law which allowed me to have a gun on my person, and not get arrested, and put to death for it. Laughable though it sounds to everyone, including myself and Mistress, I am legally Mistress’ personal bodyguard! We both know that a medal winning kick-boxing champion such as Mistress, would very easily, and very quickly kick seven shades of shit out of yours truly in a fair fight, but that single piece of paper showing me to be a licensed bodyguard, permits me to legally carry even a fully automatic firearm in a public place; just like Mistress.
******
After three years of service to Mistress, I’d almost forgotten that she’d bought me from my previous owner, for cash, and took me home, rather than met me in a gay club, charmed me, and made me want to go home with her at the end of the night for the obvious reason. I like to think that in that situation, I would have gone home with Mistress from that club.
In those three years I had been able to save almost eight thousand dollars towards my goal of freeing my sister from her bondage. I knew that a trained administrator wouldn’t be cheap to buy, and that the paltry eight thousand I had saved up, was going to be nowhere near enough. I’d need three or four times what I had, but figured that I had plenty of time to save up, because I didn’t see it likely that my sister’s owner would sell her any time soon, if she was any good at what she did.
In those three years, I had taught Mistress to make love like an old fashion courtesan, and she became very good at it. I think that over the same period, my own pleasure skills improved, too. At least Mistress thought that they did! It was on our third anniversary that Mistress gave me her third, and final, cherry. I’d thought that her pussy was tight, but when I first tried to push the smaller of our double-ended pricks up her ass, I realized that it was even tighter.
Mistress offered me her ass, and instructed me to fuck it. I had always given Mistress anything she wanted; in or out of the bedroom, and what she had just asked for would be no exception, but it would be different. While Mistress would get what she wanted, it would not be the way she wanted; well, not the first time anyway. Even the smallest of our toys would be too big for an orifice so tight. She got on all fours, sticking her ass in the air, and repeated the demand for what she wanted.
I settled down, off to one side of Mistress’ thighs, caressing, stroking and cupping those lovely firm young buttocks in my hands, while making sure that Mistress could hear my voice quietly. As my fingers explored the crevice in between her buttocks, she lifted her hips up off the bed, and I quickly pushed all six of our pillows underneath her belly to support her shapely body. As I lowered my head and began to run my tongue over her buttocks, she responded by reaching around with her hands and parting them to make it easier for me.
Mistress had the most delectable little asshole imaginable, and I couldn’t resist the urge to kiss it. Nor could I resist the urge to rim that lovely little anus, while slipping a couple of fingers into her pussy at the same time.
When I did that, she let out a little, low groan, of pure pleasure, and that just encouraged me to go a little further. I put my mouth to that tight ring and started to probe it with my tongue. After a couple of minutes, I reached into the drawer in the bedside cabinet, for my tube of KY and for the only item in my little collection of toys that I used on my own asshole on rare occasions back in Marseilles.
I applied the lubricant to her ring, smiling in pleasure at the low moan that the sensation elicited. She cried out as my fingertip slipped into her rear entrance, and she gave little gasps as I moved that finger around, probing and stretching her ringpiece, quickly adding a second finger, and then a third. Once the third finger was sliding in and out without a problem, it was time to go a step further. I lifted our one and only anal dildo from where I had put it on the pillow next to Mistress’ head, and very gently, I eased the tip of it into her asshole.
Mistress moaned as I moved the dildo in and out of her rectum, clearly enjoying what I was doing. I started to move it faster, in and out, and she thrust her hips up in time to my thrusts. After a while I stopped using the anal dildo, pulled it out of Mistress’ ass, and reached back into the bedside drawer for a conventional, vaginal, vibrator. I squeezed lube onto that, rubbed it in, and switched it on, before seeing if it would fit up Mistress’ ass. I didn’t force it in; I didn’t dare try to do that. It had to go in without too much pressure.
As I was gently trying to insert the large vibrator into Mistress’ tight little asshole, I asked her to, “Try and relax your little botty Mistress; this is quite large, but I’ll be gentle, I promise I will.”
“I’ll try,” she whispered back, and slowly the vibrator disappeared into her bum. Mistress groaned loudly as I started to push the vibrator up her adorable little bum. I began pushing it in harder, and she started gasping and panting, fingering her pussy as I did so. Mistress moved in time with my thrusts, pushing backwards and upwards with her pelvis, as I pushed down with the big vibrator, moaning, as the obscenely large piece of vibrating plastic disappeared within her slender little body, and the sight was just so beautiful.
I could tell that Mistress was just about ready to climax as I reached underneath her, pushing her hand away from her pussy, to tickle her clit. The resulting climax was just wonderful to behold. I’d heard her squeal in orgasm before, but that time, she simply screamed, as the climax overtook her, and seemed to go on for an inordinate amount of time.
Gasping for breath, those lovely tits still heaving, she rolled over to look up at me, face flushed red with her exertions, and looked up into my eyes. She said just three words to me, “Fucking wonderful babe,” and those simple words made my entire day. Mistress took me by surprise, yet again that night, by pointing at the double-ender we normally used and saying, “Use that on me next time, Princess, that way you’ll get some pleasure as well.”
“When’s ‘next time’,” I asked, hoping it wouldn’t be too long; the next night perhaps, or at least that same week.
“Right about now, babes,” was the answer, before Mistress rolled back over and positioned herself on all fours, pointing that delectable little bottom right at me; both of her holes still glistening with different types of lubricant. What could a woman do at a moment like that, except what her Mistress asked?
I knelt there for a few seconds, just looking at her bottom, before she began to get impatient. She took me by surprise by turning very serious and looking right into my eyes. “Princess”, she said, in her most stern voice, “when I tell you to vigorously nail me up the ass like a proper little cheap whore, I don’t mean kneel there and drool like a baby at the prospect. You and I both know that you’ve wanted to bugger me witless since the first time you pushed a large piece of latex rubber up my pussy, and now is your chance. I mean, grab the dildo and do what I demand; and I am demanding to be buggered witless.
I’ve done it to you so many times, and I’ll admit that I enjoy buggering you, so tonight, I’ll take it the same way if you’d like me to. You’ve earned it so many times over by now, and it’s overdue that I repay the pleasure. How could I love you so much, and not give you the odd little thing that I know would make you so happy? You will be gentle with me though, won’t you?” Despite the words, it wasn’t a question! I had wanted to do my Mistress in the ass, for a considerable while, but I hadn’t realized just how transparent I was with my wants. I hadn’t mentioned it to Mistress, and never would have, but once the offer was made, I was going to take it.
“I’ll be as gentle as you like, Mistress, I swear I will be. You already know that I will, or you wouldn’t have offered me this gorgeous little peach.”
“In that case my big Princess, now’s your one chance to convert me to your way of thinking; on the all-important subject of ass fucking, anyway. I feel brave enough to let you shove your rubber cock up mine, tonight; the way you’ve wanted to do for a while; but if you don’t do it now, you may not get another chance. If I don’t get my pleasure now, I may not find the nerve to ask again, and you’ll have blown your chance.” She changed her position ever so slightly, pointed at her bum with one finger and said, “Ass… fuck… right now…you beautiful, dirty blonde cow!”
I grabbed our double-ended dildo and said, “Yes Mistress, whatever you demand!”
I did what she demanded of me, and I was still a little nervous as I knelt behind her and placed the tip of the double-ender at her rectum before very slowly, and very gently, pushing it in, all the way to where my pubes would have been, as Mistress encouraged me. “That’s it Princess, shove it in nice and deep. Bugger your randy little Mistress rigid, the way you’ve been dreaming about since the first day you pulled my knickers down to my ankles and I watched as I stepped out of them. I can take it all the way, just like you can.”
The feeling of pushing the double-ender up Mistress’ ass was wonderful; her ass was even tighter than her pussy, and when I had the toy as deep as it would go, and was pressing the front of my thighs against the back of her own, I held still, and reached forward to gently cup Mistress’ big tits in both of my hands. Then I asked her if she felt ok with what was happening. She nodded, and said, “Continue with the big rubber cock, Princess, and make me squeal!”
Following the very clear instruction I had received, I began working the dildo back and forth slowly, in short thrusts, and gradually extending the length of the thrusts, while keeping them soft and gentle. I knew, right from the start, that Mistress was enjoying anal sex, and I was quite proud of myself for giving the woman I loved the pleasure she wanted. I was gentle with her, as I should be; only becoming vigorous when asked to be, or more accurately when it was demanded of me that I be more vigorous, and that I thrust a little harder. That was the moment when I realized just how tight Mistress’ asshole really was. I don’t suppose that my own was any less tight, the first time I got fucked up it, but my memory of that instance was of the pain I endured from it, and the way I cried and begged for my Master to stop hurting me. Needless to say, the bastard did no such thing; he simply pulled my hair harder, and told me to shut up.
As I held my position with my legs pressed up against Mistress’ legs, and felt her wiggle her hips, I knew it was time to do what she wanted, and slowly pulled the rubber prick out of her asshole, in preparation to push it back in again. I knew I was going to have to be very gentle with my Mistress, and her virgin ass. She was right when she asserted that I’d wanted to do that for a long time, although not as long as she thought. The day I first pulled her lace panties down and got a good look at her considerable bush, I was more concerned about making sure that she was willing to keep it out where I could get at it. Doing her up her lovely peachy ass didn’t enter my mind. It was an idea that I didn’t have until much later, and we were watching one of her newest porn films. I had Mistress on all fours on the living room floor; skirt up around her waist, panties around her ankles, and three fingers knuckle deep in her pussy as I stroked her clit and talked dirty to her. We were watching a particular scene where one woman was vigorously doing another woman in the ass with a big double-ended dildo, and I was sure that Mistress’ pussy was getting wetter and literally pulsating around my invading fingers as she watched the big rubber prick being pushed into a greased-up ass in front of the camera, while the owner of the ass moaned loudly.
******
Then there was Mistress’ third trip to the fetish shop, in her spiked collar. She wanted to take her role-playing in that store to the next stage, presumably in one of the rooms on the upper floor. I wasn’t quite sure how it would work out, but, as was always the case, what Mistress wanted, Mistress got! She dressed herself like a fifty dollar whore, put on the collar and gave me the leash. Mistress chose to return to the store on the same day, and at roughly the same time as the previous two occasions, hoping that the same women would be in the store, as the last two occasions.
They’d been green-eyed before, and she wanted to make them even worse. There were ways of doing that, as long as she had the nerve to go through with a performance on a bed in one of the rooms, and I wasn’t entirely sure if she would, or not. After all, I was the only woman she’d shown herself to, and I doubted her willingness to take her clothes off in front of many other women. Of course, everything depended on one of the other women creating a situation where Mistress could get her wish without being seen to be offering herself on a plate. She couldn’t offer, and being the jealous owner type, I wouldn’t either. We’d have to be seen to have been maneuvered into having Mistress perform on another woman.
My part was going to be quite difficult to get exactly right; I had to get Mistress the sort of woman she wanted to play with, while making it all appear to be completely unplanned. A lot of it was going to have to come from my instinct once things began. I knew Mistress’ taste in women; I’d had plenty of time to judge what got her nipples to stand to attention and her pussy to get wet. Her taste in women tended to run, mainly, to those like herself; small-boned and petite, with a large, round ass and big, firm tits. Facial features weren’t so important, though; big tits were far more important than a pretty face. Now, I knew she wouldn’t want to be made to service another Mistress; she’d want to give a little pleasure to a slave who may not have had a great deal of it recently.
Mistress’ idea worked out quite well. When I led her through the doorway, on her leash, in her sexy outfit, we got a round of applause. There were several familiar faces; all women who seemed to spend a considerable amount of time in the store, along with their girls. While a couple of them had men on leashes, most had young women in tow. Running on my instinct, despite my initial surprise, it only took me about five seconds to guess which set of panties Mistress was going to want to get into. The girl was of mixed race; uncommon in the day. She was in her early teens, standing about four feet ten inches tall, with an ass like a peach and tits like watermelons; just Mistress’ type! Her skin color didn’t matter too much, or at least I didn’t think it would. To look at her, I was a little curious about her parentage. If she’d been born in America, then the black half of her parentage would have to have been slave stock, but what about the white half? Was the other half also slave stock, unable to find a white slave to marry, or a member of the Master’s family; probably one of his sons.
Master himself probably wouldn’t have bothered with a Negro woman, but a horny son with no girlfriend just might have. For a teenage boy, pussy was pussy, and waiting until she reached eighteen often wouldn’t feature in his plans! Sons of rich families often forced themselves onto young, often pre-teen, slave girls, because they were too young to have sex with free women. While it was technically illegal to have sex with any underage girl, even a slave, the cops tended not to give a damn. Usually the illegitimate child would end up in the slave compound because its father didn’t give a damn. After all, he’d already gotten what he wanted, and the kid was often just an embarrassing reminder of how desperate he had been to get himself some pussy. I’d seen it happen with my own eyes. In some households, slaves could do what they liked to one another, as long as it didn’t interfere with the duties they had to carry out for their owners, and if that included the big slave raping any and all of the cute female slaves, strictly according to rota, then who gave a flying fuck? In other households, slaves were required to treat each other the way the owning family treated each other. In my household, if a slave man wanted to fuck a slave woman, he had to get her permission first. Just as a child, I saw the effects of not doing so. He was in his late twenties, stood about two meters twenty, and was built like an ox. The young woman didn’t stand a chance of fighting him off. He was a new purchase and didn’t understand the rules of his new household. A hundred strokes of the lash, and eight hours staked out in the burning sun, taught him the error of his ways, and he never did anything like it again.
I had heard stories whilst in the slave compound of other ways a mixed race child could be conceived. One woman told us all her horror story. Her owner liked live sex shows that he could watch along with his guests. Those shows usually had but one theme, her, and often one or two other white women, being repeatedly raped by several male black slaves, to the cheers of the audience. She’d had three babies to the other slaves, and as soon as those children had been weaned off milk, they were sold off. That was the one thing a slave owner could get into huge amounts of trouble for doing! Whipping an adult slave to death was quite acceptable; yet selling a child of under thirteen could get an owner five to ten years in a jail cell, maybe more, depending on the age of the slave! No slave could be legally sold until he or she had reached thirteen years of age. That was to prevent babies being sold to pedophiles, as had happened in the past. Slaves or not, no baby should be subjected to that, and her owner had been caught breaking that law. All his slaves were confiscated by the state, and auctioned off, and he had been banned from ever buying any more. One of the other young women in the compound with us had been one of those babies and she added her horror story to the others. I realized, as I was listening to them, that my life could have been far worse than it actually was.
Anyway, it was time to manipulate the women in that room, so that Mistress got what she wanted. The outfit was to begin the conversation, and I was to steer it in the direction Mistress wished. Her plan was fine. “Well then, lucky bitch…you’re still hanging on to Miss. Tits, I see. Don’t suppose you’ve changed your mind on parting with her yet?” The same woman who had asked to buy Mistress the first time, was clearly still intending to buy her from me.
I didn’t even see fit to answer the question; mainly because I thought that silence would serve me better than any choice of words. “Didn’t think so. What does she do for you that no other girl could do?”
“She serves me well in the bedroom, like no one else I ever owned. She knew nothing when I bought her, and I taught her personally. Could I buy better? Could your girl do better than mine” I challenged.
“Seems like we need a comparison here! Would you permit your bitch to give a demonstration on one of us?” she asked. Bait taken then!!!
“Well, Princess?” I asked Mistress. “Would you care to demonstrate your talents on one of the women in this room?”
“Can I pick my own partner Mistress, please?” Mistress asked me.
“Anyone have an objection to my girl picking her own demonstration partner?” I asked the room in general.
“No,” was the standard answer from those who voiced an answer. “Bingo, Mistress; you’ve just got your girl,” I thought to myself. “Time to see if I read you as well as I think I can.”
Mistress looked around the room and walked towards the girl I expected she would go for. Seeing as she was still on her leash, I had to follow her. “I’d like this girl, Mistress, if that’s ok,” she said. I looked at the girl’s owner, and she nodded her head. Mistress had got her busty piece of teenage pussy!
“I’ll allow a basic demonstration down here, but any more than that, and she,” I pointed to the woman who had requested the demo, “can pay for the necessary room upstairs.”
“Agreed, just as long as I get a bedside seat,” she replied. “Oh, Mistress” I thought, “this is going to be fun.”
Mistress took the girl’s hands in her own and asked, “What is your name, young lady, mine is Jennie.” I knew that Mistress’ first name was Erika, and I just ignored the lie.
“Abigail,” replied a young woman with a smile on her face at being addressed in such a pleasant manner.
“Well then Abigail, will you allow me to make love to you?”
“Yes, Jennie; if Mistress wants me to.” She turned to her owner and asked for permission. That permission, of course, was immediately forthcoming. Everyone wanted that demo’, and allowing her girl to be fucked by another girl was a small price to pay while I put my money where my mouth was.
“Mistress,” asked ‘Jennie’, “Where should I make love to Abigail; behind the empty counter?”
“It’s as good a place as any,” I replied, seeing as it was as good a place as any.
Mistress unclipped the leash from her collar, and did the same for Abigail. Then she led her behind the empty counter, as many of us leaned over to watch what was going to occur. “Lie down, sweetie,” instructed Mistress. Abigail lay down on her back and Mistress parted her legs, before kneeling between them. We all watched as Mistress open Abigail’s sexy little top and began to tease her little nipples. The music had already been shut off, and we could all listen to the soft sounds of pleasure that Abigail was making. The expression on Abigail’s face told a complete story. I don’t think that her Mistress was a tenth as gentle with her as mine was with me. Abigail was smiling, whimpering and writhing, as Mistress fondled her nipples. After a few minutes, Mistress knelt upright and scooted backwards. She then lifted Abigail’s skirt and pulled down her panties. Poking out her tongue, she began to gently suck on Abigail’s clit and probe the inside of her pussy, at the same time as sticking her ass out. She was giving the body language equivalent of the words, “Here are my dildo holes ladies; does anyone want to play with them for me while I eat this under-age pussy?”
As Mistress munched on Abigail’s pussy, one of the audience members knelt down behind her, and looked up at me; clearly she’d recognized the gesture, and was the first one to work up the nerve to interfere. She raised her eyebrows in a questioning gesture, and I nodded my head. She quickly lifted Mistress’ short skirt to reveal the surprising fact that she hadn’t bothered to put panties on before we came out. I didn’t even know that she hadn’t put any on. “She’s got no panties on!” she announced very loudly. Running a hand under Mistress’ crotch, she brought it out and showed everyone that it was wet. She licked Mistress’ juice off her hand, and put it back where it had come from. After which she began to softly finger Mistress’ tight pussy. I was surprised when she released her grip on her girl’s leash and told her to, “Go and please Miss. Tits’s owner, and keep her sweet!” For the first time in my life, I was going to have a slave girl treating me like a genuine Mistress. I could get her to do anything I reasonably wanted, in order to be pleasured! She walked up to me and asked, “What can I do for you, to give you pleasure, Mistress?”
What indeed? “I want what your Mistress is doing to my girl,” I replied, as I leaned over the counter and stuck my ass out. The girl reached up my skirt and pulled down my panties, allowing me to step out of them. What surprised me most was the fact that I recognized feeling within myself; feelings of jealousy! Despite the fact that I had a teenage girl with her hands up my skirt, I was jealous of the woman who was crouching behind my Mistress and had fingers in her pussy. She was my owner, so what right did I have to be jealous of anything she did, or anything she got? While I wanted to keep that young, fit, body all to myself, I shouldn’t have expected Mistress to be faithful to her slave. The funny thing was that I did expect Mistress to be faithful to me, even though I knew I shouldn’t. After all, Mistress had told me that she loved me, and everyone knew that lovers should be faithful to each other. I suppose, however, that the teenage hands wandering around my ass and pussy were indications that I also was in the process of being unfaithful to the woman I loved, and I wondered if Mistress would feel as jealous of me, as I was of her. However, to judge by what Mistress was doing, I doubted that she’d even see what I was doing, let alone be feeling anything but the pussy on her tongue and the fingers in her own pussy. Hopefully, I also wouldn’t be feeling much more than the fingers in my pussy quite soon.
I felt the touch of the slave girl’s fingers around my crotch, and the unmistakable sensation of the application of artificial lubrication being applied to my pussy lips. Then she slipped the first finger inside me, and as I hoped, my jealousy began to fade as my pleasure began to take over. In a way it was a strange feeling, as the girl giving me pleasure wanted none in return. She didn’t expect to gain anything out of what was happening, and concentrated purely on my pleasure. Despite merely being in her teens, the so far unnamed girl was pretty good at what she did. Her fingers were stimulating my sensitive spots like a professional; as I did for my Mistress. My first thought, after that one, was to offer the girl the same in return, but that probably wouldn’t suit my role.
Anyway, as I enjoyed the sensation in my loins, and listened to Mistress vocalizing her pleasure through Abigail’s pussy, I noticed that everyone in the room was looking down at the three women on the floor. Mentally, I compared the shy, reserved and innocent young woman I had to encourage to show me her pussy, in order to show her what my fingers and tongue could do to it, to the dirty little lesbo slut on the sex shop floor, being fingered by a complete stranger, and eating out another complete stranger. How my beautiful, shy, little Mistress had changed since that first night! I wondered how far Mistress was prepared to go, that day, but I figured that after she’d worked up the courage, she’d go all the way with the woman kneeling behind her. In a way, she was going to discover how the other half lived, because the woman was not going to treat her in quite the same way I did. Mistress wouldn’t be hurt, because that was property damage, and the penalties could be severe if the other woman willfully damaged my property. Injuring another owner’s slave was equal to damaging her car, or breaking the windows of her house. In America, a slave was a valuable piece of property, and prison sentences had been known to be handed out to people who intentionally injured them. Another question I asked myself was ‘did I want to watch Mistress be fucked?’ I decided that I did. I had a gun in my purse, and I thought it likely that I‘d be the only person in the room, apart from Mistress, who did. (Getting a permit to buy a gun wasn’t exactly easy, and getting one to allow you to carry it concealed was much more difficult. The articles of Confederation originally allowed a citizen to carry whatever the hell he damn-well pleased. Times, of course, had changed considerably. The much revised articles from the nineteen twenties put very strict limits on what a citizen could own, and that hadn’t changed much in the following hundred years. While you could own a rifle, it had to be manual operation. Machine pistols were only allowed by special permit, and Mistress and I both had those permits.) I intended to make sure that Mistress was not mistreated, with force if need be.

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You never know who you’ll meet at the Pavilion.

Sean Reynolds sat on the edge of the bed, with only a white bath towel draped across his lap to protect his modesty – a modesty that was in serious danger from the sight only a dozen or so feet away. Short of closing his eyes, it would’ve been impossible for the twenty-one year old redhead not to see the woman in whose name the motel room had been registered. She had, after all, left the door to the bathroom wide open, just so he could watch her.

How I Spent My Summer Vacation Chapter 1

OK. This my first attempt at adult writing. Be kind and constructive and you will motivate me to post more of the story.
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Chapter 1
Background
My name is Caine. I first read about sex in Cuba on the internet. I hooked up on the internet with a guy who had made the trip three times and could only brag about the great times he had every time. Sammy and I wrote back and forth enough that I figured I had to give it a try.
Learning about Cuba
Doing my own internet search I was able to research, finding most everything Sammy had told me was correct; and more. It seems that I can hook up with a young lady with an apartment for a night, or a month if I wish, if I pay for the food and our meals out!! What’s more, if I get tired of her she will refer me to any number of her girl friends and I can swap out. Seems almost too good to be true! Well, reality was something different. The key is to understand that the Cuban government does not allow the internet in Cuba, and then understand what Cubans do to get around that ban. You dig deep enough and you find websites in Mexico and Canada that advertize Cuban ‘vacations’. It is all veiled to prevent Government reprisals against those who use the system.
First I didn’t need any swap outs. Second, Maria kept me well entertained. She even liked my ideas and caused me to have one of the best months of my life. It seems that young ladies are commonly ‘available’ as young as 14 or 15. As long as there is no violence against them, the police look the other way. I guess the cops just look at them as ‘working girls’.
Cuba boasts the lowest rate of Sexually Transmitted Diseases [STD’s] in the world. I still packed a case of assorted condoms since I couldn’t find any data as to their availability. You see, I can only use the EX-Large size. Anything smaller acts like a tourniquet and only covers my cap and about first one third of my length anyway.
If you go to any of the large ‘clubs’ you will pay around $10US in cover charges. However, the ‘clubs’ are mainly populated with women out looking for a ‘date’. It’s not unusual to find 150 to 175 women, and only 25 or 30 male tourists. These women will charge you anything they think you will pay, but never less than $50US. Maria did much better for me.
The United States is still quite stuffy over Americans going to Cuba. There are no direct flights. You can fly there, though, via Cancun, in Mexico, or through Ontario (or maybe Toronto), Canada.
I talked my boss into letting me take most of Friday off. I hoped he’d go along with it, as I had made reservations to leave my hometown on a 2PM flight to Cancun. I made my connecting flight OK and arrived in Havana before dark. Maria and I had set it up that I would be met at the airport by her brother, Roberto, who drove a cab. He took me to Maria’s place, and wouldn’t take any money. He said, “Maria has already paid me, and she would be very mad at me if I even take a tip from you.” He came inside with me and introduced me to his sister. I think I said that Maria is 17. She is about 5’4″ and must weigh all of 110 pounds. She greeted me with a big smile, a bigger kiss, and a quick goodbye to her brother.
We ate a light meal of great fresh fruits and fresh baked bread. Maria asked if I would like to watch a video with her. I said, “Sure.” We settled in for some preliminary ‘get-to-know-you’ time.
Maria’s apartment is fairly small. When you come in the door you are looking straight through the living room and out some picture windows at beautiful scenery. To the left is an efficiency kitchen with a small one burner stove and a small dining table for two or three, but a large, very new refrigerator. I remarked on the new fridge. Maria is very proud of it. It is the first thing she has bought on her own with her own money. Looking to the right from the door is a half-wall with a bedroom nook behind it, and the bath beyond it. Her living room has one chair, and a small couch and assorted end tables and some tasteful lamps. We snuggled on the couch, but I don’t remember the movie. The couch is just big enough for me, sitting straight on the right side, and Maria sitting with her back my left side. She soon placed her right hand on my thigh. I responded by draping my left arm over her. Gee, that put my hand on her left breast! Maria responded by snuggling even tighter against me. I nuzzled her neck and she giggled, and turned her head slightly. This placed my lips in line with her ear. I blew lightly in her ear and then tongued it. This sent shivers from her head to her toes. While she was turning toward me she remarked, “It looks like this is going to be a great week!”
We kissed a full, complete, and long kiss. Both exploring the others mouth with our tongues. Her turning moved my hand from her breast. So I used my right hand to continue what my left had started. After a bit Maria asked if I would like to move to the bedroom. I told her I really needed to take a shower before we got serious since I had not had a shower since I caught my plane from home. Maria said, ” Showers are always a good thing. We can both take one. Then we will both be fresh for what comes after.” We held hands as we walked into the bedroom. We didn’t discuss it. We just both began undressing each other, interrupting often to hold each other and kiss. Maria went in the bathroom first to do ‘girl things’. When I heard the shower come on I went in. The shower was fairly small so we had to stand close together. We started with me lathering up Maria’s arms, then her back, followed by lathering her very nice breasts. I then slid down with back against the wall and my knees out in front of me. This way I could pick up one of her feet and place it on my knee so I could wash her foot and ankle. Once done there I washed her calf and thigh. My hand just naturally went up the inside of her thigh and put my fingers up into her pussy. Maria jumped and said, “OH!” when she suddenly felt me inside her. “I wasn’t ready for that!” “Sorry”, I said. “No-No. Don’t be sorry. It feels good. It just came as a surprise.” “Oh good. I like to provide surprises.” , I grinned. So I finished up that leg and put it back on the floor of the shower and picked up her other foot. She helped placing her foot on my other knee and I started washing it, just like the other leg. When I reached her pussy this time she was expecting me and I didn’t disappoint her. But, after I had washed that side of her pussy I put my hands around her hips and pulled her clit right into my mouth. “Wow, I wasn’t ready for that, either!” “I was just taste testing. It wouldn’t do to leave any soap in there. We wouldn’t want a soap rash, would we?” “Oh of course not. I guess I have never been taste tested before! I’m supposed to be the ‘pro’ here but you seem to be doing the teaching.” “Well, I guess it’s because I get as much enjoyment out of seeing my partners cumming as I do cumming myself.”
“Well, I guess it’s my turn to lather you up.” And, she did. Maria even tried my method of scooting her back down the wall and putting my foot on her knee and washing me from my foot to my crotch. She did a great job of washing my balls with the first leg. On the second leg she worked her way up to the top and saved washing my cock to the last. After a thorough washing she held my now steel hard cock in her hand and slipped it into her mouth. At first just the cap went in. But after a couple of short strokes she plunged my rather substantial cock to the back of her throat. She could take about a third of my cock. “I know I don’t do this very well, but I gag whenever I try to throat a cock.” “It’s OK. I think I only know one woman that can throat me”. She withdrew my cock so she could take a breath, took my cock back in her mouth. Her hand kept stroking the rest of my cock. Maria was an expert. I said, “If you do that one more time I will cum so hard I won’t be of any use for you ’til later.” She withdrew my cock completely and said, “Well, I wouldn’t want to do that.”, and she laughed. We toweled each other off and moved into the bedroom.
We shared the double bed that took up most of the bedroom.
Maria’s English was very good. I asked how see became so proficient. Maria said, “Well, most of my ‘dates’ are from North America. So I study in the English as a Second Language group.” I asked, “What is this study group?” “Since most ‘dates’ come from over sea’s nearly all working girls are learning or already speak a second language. Besides English there are study groups for Russ, Estonian and Portuguese. There are probably more. These are just the ones I know of.” “Your level is good enough to be teaching English.” She kind of blushed, “Well, I am a tutor for new girls just coming into the ‘business’.”
It was Sunday morning. We were laying in bed recovering from our latest ‘sexual exercise’ when Maria asked, “Will I be able to satisfy you for a whole month? You are using up most of my bag of tricks in the first three days!” I said, “Well, to tell you the truth, I have a fantasy I would like to share with you. Would you like to hear about it?” Maria sat up in bed and turned toward me allowing the sheet to drop to her waist exposing her beautiful petite breasts, “Yes. Tell me!” “Well.” I hesitated, “I would like to fuck a virgin.” “Caine, maybe you haven’t noticed, but there aren’t many virgins in Havana.” “I know, but, you told me yesterday there were many still in your home village.” Maria had shared with me that it took about a four hour bus ride to her home village. It was quite isolated and a very poor place. “Tell me how much does it cost for a family of four to buy enough food for a year?” Maria thought about it, and said, “It depends a lot on the current prices of food. They vary all the time. But, I think that $50US would usually do it.” I already had this information, but I wanted Maria to confirm it for me.
“Hmmm, how about if you took the bus home Tuesday, the stayed with your mom for a couple of days. If I gave you $100US, do you think you might be able to find a family that might trade a daughters virginity for $50US?” “Maybe, but, you said you would give me $100US?” “Yes, you spend what you need to on bus fares, clothes, I don’t know, any other ‘expenses’, and you get to keep the balance. I’m thinking maybe you could take the Thursday bus back maybe with a friend in tow for me?”
Maria thought about my offer. She said she knew of at least two girls that might work with. Both of them were younger than her, and lived in single parent families. Their dad’s had both been killed, and their mom’s could hardly make ends meet. Maria asked, “Do you have any other ‘requirements’ other than they be virgins?” “Not really, just that they won’t get me in trouble with the law. I think they ought to have the beginnings of some tits, you know I like them small.” Maria looked down at her barely B cups and blushed. “Hey, I’m not trying to make you feel bad. You have just what I like. Hmmm, maybe I should say they need to have at least a little bit of pussy bush growing, too.”
“OK. As long as their parents are OK with it, they have the beginnings of some tits and pussy hair they will be acceptable to you?” I thought for a minute and said, “Oh, YES!” Maria thought for a minute, “I am certain that the police will look the other way as long as the parents don’t complain, and they have the beginnings of a woman’s body. I know a couple of other girls here in Havana who started out when they were 9 and 10 years old. The law never hassled them. Their parents did not file any reports since the girls were both bringing in the only money the families made.” “Well, I’m not looking for anybody THAT young.”, as I got a mental picture of a nine year-old with hazelnut sized breasts and a little fuzzy pussy.
“OK. If I leave on the Tuesday morning bus I should be back Thursday late afternoon. The only thing is what are you going to do for those three days?” “I can just look after myself. I can go out and buy some food and bring it back here to cook it.”, I said. Maria was adamant, “No. That won’t work.” “Why not?”, I asked. “Because your Spanish is not good enough. You might get what you want, but probably not. And, if you do, it will be way over-priced if you try and buy it. No, I have another plan.”
Monday morning, after we had shared wake-up exercises, and our shower Maria said she had some errands to run and she would bring back some fresh fruit and things for lunch. We kissed and she headed out the door. Now I knew from my research that most girls did not have apartments but relied on their ‘dates’ to pay for hotel rooms for them to have a place to stay. Since I had found Maria I had not worried about that situation much.
About an hour before noon, I heard a key in the lock. When the door opened not only Maria came in, but another girl, too. She was a little shorter than Maria and could not weigh over 85 pounds. While there was no doubt of her womanly attributes (Her narrow red tube top and black, skin tight short shorts made that plain enough to see.) she had to be younger that Maria. Maria said, “Caine, I want you to meet Charlotta. Charlotta, this is Caine.” I greeted Charlotta not completely understanding what was going on. “Charlotta will be your maid, housekeeper and ‘companion’ while I am gone. She will do your shopping, laundry, and anything else you would like.” Maria smiled when she repeated, “…and anything else you would like.”
“Hmmm, does that mean I can’t go out in public while you are gone?” “Oh, No. Charlotta will just be your escort and ‘friend’ when you are out and about. By the way Charlotta likes to go out to a special swimming beach she knows about.” “What goes on there?”, I asked, already having a pretty good guess. Maria shocked me when she grinned and replied, “I don’t know! I have never been there. You will just have to ask Charlotta. By the way Charlotta is taking English as a Second Language class and wants to make sure that you tutor her and correct her English mistakes.”
‘Well, this certainly looks like a great situation both ways.”, I said, holding my arms out to Charlotta. She immediately set down the two shopping bags she was carrying, grinned, and came into my arms. As I hugged her, she returned the hug with a true full-body hug!!
After lunch, Charlotta gave me a hug and a kiss, and said, “I’ll come back tomorrow after Maria has left. You will have to let me in because Maria doesn’t have another key. I’ll bring about two days of food that I think you will like.” “Do I need to give you any money to buy the food?”, I asked. Maria broke in and said, “No Caine. I have that already taken care of.” After Charlotta left I asked Maria about the food, and other expenses that Charlotta and I might need to spend. “You can pay her public expenses. Bus fares, taxis, and food that you eat if you dine out. The deal I have for her is, she gets a place to crash and an English tutor. That and I am paying for the food she brings here and cooks for the two of you. Beyond that you could buy her a small gift, but not too often. Does that sound OK?” I thought for a few minutes then said, “Wait here a minute.” I went into the bedroom and dug through my backpack that served as my suitcase. I found what I was looking for and took it back out into the living room. I sat beside Maria I opened the small box. “I bought these in Cancun even though I didn’t have any particular use in mind for them.” I opened the box so Maria could see its contents. A dainty sterling chain with a single pearl drop was the first thing that caught her eye. Then, as I shifted some tissue paper around and you could see the set of earrings, again, in sterling. They had pearl drops that matched the necklace. Finally, in the bottom of the box was the bracelet. It too was sterling and pearls. All the pearls matched. “I could give her these. What do you think?”, I asked. “They’re beautiful! Were they for me?” “I bought them before I had ever met you. At the time I bought them I thought they might be for you, but not anymore.” Maria’s face fell, “You mean you wouldn’t have given them to me?” “Nope. They aren’t good enough for you.”, I said. Maria thought about that. Then gave me a big hug and a long kiss. She giggled like a little girl, and said, “Caine, I think this is the first time I ever hugged and kissed someone for not giving me a gift!”
“I think these would be very nice for Charlotta. Give her the necklace first. Then the second week the earrings, and finally the bracelet, but keep the ones you haven’t given her a secret so each new piece will be another surprise.”
Maria gave me a nice departing kiss and hug as she hurried out the door, “I must hurry so I can get a seat on the bus.” I ask, “I thought you said the bus doesn’t leave for another hour?” “I did, but all the seats will be taken a half hour before the bus leaves. Everybody else has to stand.” An hour later there was a knock on the door. I open it and greeted Charlotta. She had her hands full of shopping bags. I took some from her and we put everything in the kitchen. Then I got a great hug and kiss.
“What shall we do first?” , Charlotta asked. “Well, I haven’t taken my morning shower as yet.” , I respond. Charlotta grins, “How would you like someone to scrub your back?” “Only if I get to scrub your back!” , I answer. “OK” We go into the bedroom and I turn and kiss her again, “May I undress you?” , I ask. “Sure. Then I get to undress you though.” , Charlotta says. I start with her blouse. I unbutton it from the top down. The blouse material was thick enough that you could not see the her bra through it, but with the buttons undone I could see it is a very pretty rose color. I remark on its color, and I ask, “Do your panties match your pretty bra?” Charlotta giggled and said, “You’ll just have to undress me down there to find out, won’t you?”
I slip her blouse off her shoulders, fold it and hang it over the back of a chair. I can see that Charlotta has a bit more size to her tits than Maria has, even before I take her bra off. Sure enough, They are just about perfect B+ cups. I turn her around and unhook her bra. Then I put my hands on her back with my thumbs hooked on both shoulder straps. As I move my hands around from her back then under her arms both shoulder straps slide off. As I continue to move my hands around her chest I cup both her breasts in my hands and pull her back against me in a snug hug. Charlotta responds by backing her tight ass up against my dick. As she gyrates against me she can feel my beginning erection.
Roberto had made it a habit to stop by sometime each day to check on me and make certain all was well. I mentioned to him, (His English wasn’t as good as Maria’s or Charlotta’s, but very good enough for driving Norte Americano’s around.) that Charlotta and I were going to a beach to swim the next day, if this fine weather held. Roberto had a short conversation with Charlotta, then turned back to me. “OK, I will pick you up at 2 pm tomorrow and drive you to Charlotta’s beach, then I will come back at 6 pm to bring you home. I asked Roberto if he would get into trouble taking up so much time and gas running us around. He smiled and said, “No, my boss thinks I am really working hard when I tell him I have booked customers in advance. We do it all the time with arrivals at the airport. But, maybe, you could give me a little gas money, just so Maria doesn’t find out.” I laughed and said, “It will be our little secret.”
Roberto was good to his word and was right on time. The drive to the beach took about half an hour. Charlotta had packed us a little food and some canned juices. She also packed two beach towel apiece. Roberto dropped us off, getting our hamper out of the trunk and handing it to me to carry. Waving cheerfully, Roberto got back in his cab and drove away shouting, “Have a good time!!” and laughing until we couldn’t hear him anymore. The parking lot was small and rather unkept. Charlotta took me by the hand and led me over to a path through the trees and undergrowth. “The beach is out of sight from the land, and only people who want to see come close from the water. After about a five minute walk we came out of the undergrowth and onto a sandy beach. The beach curved around in a crescent shape with two tiny headlands of rock out in the water. The crescent beach was probably a mile long. There were couples and small groups scattered all around. Some people were swimming, all were nude. Charlotta said, “Come on. I see some people I know over this way.” Still holding hands we made for her friends, who, when seeing Charlotta, began to yell and wave to us. When we got to their spot everyone stood up as Charlotta introduced me around. Each lady there came up and gave me a full-body hug. I said, “This is rather embarrassing to be being hugged by all you beautiful women and me with all my clothes still on.” Two of the ladies laughed and said, “Well, well. We need to take care of that, right now!”, and with that they relieved me of all my clothes in something around fifteen seconds. The guys were eyeing Charlotta, but she knew what was coming and stripped off her clothes even before I was naked. However, in my case, all the ladies came back and re-introduced themselves, complete with ‘new’ hugs!
Charlotta explained that I was a ‘friend’ from ‘the country to the north’ and that I only spoke a little Spanish, but that I was helping tutor her in English. This brought positive nods from the group. Two girls and one guy said they, too, were studying English and would I please correct them if they made mistakes.
Charlotta asked me if I would like to go for a swim with her? I got up from where we were sitting, took her hand and we walked down and into the water. I guess I had not thought about what the water temperature might be in this part of the world. I certainly didn’t expect it to be as warm as it was. Charlotta and I splashed, swam and played in the water for about a half hour. We were both getting a little tired. I was standing on the sandy bottom with water about up to my armpits when Charlotta swam up to me, put her arms around my neck and her legs around my waist. A great kiss punctuated Charlotta’s question, “Can we fuck out here in the water?” “Well, the water has made me a little soft. Do you suppose you could do something about that?” “Oh yes!”, and she took a large breath and lowered herself down into the water, using her amazing mouth and started me on the path to real ‘hardness’. We spent about another half hour out in the water. When we came ashore, holding hands, Charlotta’s friends immediately began teasing us even before we were all the way back to our towels. The girls all wanted to know if Charlotta had left any for them. While the guys all wanted to know if I needed any help ‘satisfying’ Charlotta. One girl didn’t wait for answers. Anna jumped up and ran to us, and practically jumped into my arms, planted a big kiss on me and asked, “How about me next?” I looked over and said, “Charlotta?” She responded with a big smile and, “It’s a free country.”, and everybody laughed at the big joke. Anna grabbed a beach towel in one hand, and my hand with her other hand, and said, “Come on, we need a little part privacy.” “Do you mean, ‘A little more privacy?” “Sí, and thank you for correcting me.” We headed for the tree line, but not toward the trail we had come in on. Anna took us to a little nitch in the undergrowth. It was a very private little spot about ten feet in diameter. The only way anyone one would even see in was by coming in. Anna spread out the large beach towel on the smooth sand and sat down on it. She then extended her arms up to me. I took her hands in mine and let her guide me until I was sitting beside her on the towel.
Anna was a little older than Charlotta. She was 19, about 5″ 5″ and probably about 125 pounds She had long blonde hair. Her eyes were a very pale blue and her skin was the lightest shade of brown that I had seen on the island. “Are you from Scandinavia?” “No. I’m Cuban, but my father was from Norway. I never knew him.” There was no fat showing anywhere on her body. Just muscles. When Anna leaned toward me I met her and we shared a nice kiss. Anna took my right hand and pulled it up and onto her right breast, “I like to have these massaged. Do you give good massages?” “I’m not a professional, but people say I do a good job.” With that I laid her back on the towel and began a true massage of her right breast. I started at the base, squeezing and kneading her. As my hand would slip toward her nipple I would move my hands and start a her breast base. After about five round trips I was clear up to her nipple. Holding her breast tightly I brought my mouth down and sucked her nipple into my mouth, using my lips to hold it as I pulled up and away with my mouth. By the third cycle of this and Anna was wreathing on the beach towel. I let my hands slide off her right breast and slid them across to her left breast, and started all over again. Anna reached down and began massaging her clit. “Oh, you really are good. Maria told me you were also big and long.” “Well, I don’t know about now. Charlotta just drained me about ten minutes ago.” Anna said, “Hmmm. Just let me worry about that.”
I finished her left breast and she sat up, pushing me into the down position on the towel. She moved to her knees placing her mouth over my dick. I understood that some women could actually ‘throat a man’. I had only been throated once. And not very deeply. However, I didn’t think I ever expected to meet someone who could ‘accept me’ since I am known as ‘quite large’ [I have to be careful here. Others have told me this. I do not wish to be consider a bragger.], and didn’t think anyone would attempt it on me. Anna was about to prove me wrong. She took my semi-limp dick into her mouth, and began swallowing my cap. I had never felt anything like that before. Anna was good for 30 to 45 seconds before she would withdraw me from her mouth and take a breath. By the third cycle she had me hard as a steel bar.
The amazing thing was, she was actually swallowing almost half my cock! I said, “Anna, another cycle or two and I’m gonna cum!” “Oh no! I get you in my pussy for your load!” At that point she moved very fast. In a single motion she positioned herself over me and lowered herself onto my shaft. I was concerned about her not being wet enough yet. Not an issue. Anna impaled herself on my cock in one great thrust. Then began a leisurely pumping of my dick. “Caine, how long can you hold out?” “What do you mean?” I didn’t understand if she was trying to rush me, or get me to hold on longer. “I would like to cum first, Caine. But I want you to cum soon after me.” “Oh. Ok. I think I can hold out for a couple of minutes, if that’s what you mean.” “Yes, yes, yes. Hold out for me.”, as she kept moving up and down my shaft. Shortly thereafter Anna screamed, “I’M CUMMING!!” Which was a good thing, because her muscle contractions just about pulled my cum out of me. I mean, I was pumping, but I never had a woman who’s vaginal muscles were so strong as to milk me.
And that’s where Charlotta found us. Anna on top of me with my arms around her. Both of us sound to sleep. “Come on my lover boy. It’s time to pack up and meet Roberto in about ten minutes.” I woke up and tried to remember what had happened. After just having Charlotta, then Anna, I realized I had never been drained this completely in my Life. We had to wake Anna up so I could get out from under her. As she awoke I asked her a question, “Anna, I think I heard you mention Maria when we were just getting started. Did I hear you correctly?” Anna smiled and said, “Maria and I have been friends for years. She told me how big you were and she thought we might have a good ‘fit’. I will have to thank her. She is correct. And, thank you for one of the greatest fucks I have ever had.” “No, I must thank you I have never been throated like that, and I’ll probably never have it topped. Thank You.”
Charlotta cut in, “OK. Enough thank you’s. Caine, we have to go.” We went, waving to the rest of Charlotta’s friends as we walked passed them, and got to the parking lot with five minutes to spare to find Roberto waiting for us. On the way into town I asked Roberto if we were late? “Oh no. My last fare took me almost half way to the beach, so I just came out here and took a little nap, but, don’t tell my boss.”
I laughed and said, “It will be our little secret.”
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The Highschool Life of Ry Ch.1

Alright you guys, here is the complete version of this chapter as well as a promise from myself, that there will be many many chapters to come. to give you an idea, these first chapters will be apart of “book one: Sophomore Year”. I am planning to have 3 total books for highschool (sophomore, junior, senior) then the College life saga will begin. This will only continue through the positive feedback in the comments, I do not care about votes.

The New Boy

I may not continue Why dont boys like me? and possibly make a sequel to Game Night? Leave in the comments what you think I should do.

Sucking Roberts cock

This is a true story of my first time with another male, Robert was a boy i grew up with, he was a neighbor, family friend and was maybe 5 years older than me