Looking back I now realize that these experiences don’t come along often. They’re somewhat random and need to be appreciated and savored at the time. It was sometime in the mid-80s, I was 22 at the time with some sexual experience, but I wasn’t what you’d call a ladies man.

I didn’t normally make the first move and probably missed a few chances along the way. For example, the cute girl handling our AP processing. I delayed and delayed and next thing I knew she was dating one of the IT guys. I was handling the Expense application in our data processing department when our new supervisor was introduced to us. Being the only guy in our small department I no doubt took most notice of what a babe she was. Donna was about 5-6, long dark brown hair, dark dark brown eyes, small nose, wide smile. While she was talking to some of the other staff I took in her striking shape, proud healthy breasts, narrow waist wide shapely hips. Wow, it was going to be nice, and a bit distracting, to have this beauty strolling around the department every day.

“Hello, you must be Bill?”

“Um, yes. Not such a tough guess?”

“Well, with the other options left being Mary and Lisa..” We chatted a bit about what I did there and my plans. Honestly for a guy my age it was kind of tough to keep my eyes up. But I got through. The younger guys in other departments would ask me at lunch or after meetings about working for Donna. Many comments about her tits and ass and whether I’d tried asking her out.

“No, of course not. She’s not interested in me. She must have a boyfriend. She’s a few years older than me, etc, etc” Of course they all had plenty to say about what they’d do.

Donna didn’t exactly flirt. She was nice to all the people in the department, not just me. She was tough when needed and understanding if we had issues with work, or needed time off. I had nothing pressing outside of work so I put in extra time when available. Both for the extra money and to show how dependable I was. Donna was often working late too. One night a few months after she’d joined our department I was working at a terminal outside her office. I was having trouble making sense of what someone had entered, so I asked Donna if she could take a look at it. She came out and saw me sitting in the chair at the terminal.

She asked, “Where am I supposed to sit? On your lap?”

Now here’s where a snappy comeback would have worked. But…

“Oh um, sorry, sit here.” And I got up. She sat and concentrated on the screen. My concentration was split between looking over her shoulder at the screen, down her blouse and trying to read the tag on her bra through the sheer back of her blouse. All three were successful, confirmed 34C, very nice cleavage, oh and there’s the problem with the report.

“So Bill did you get a good look?”

“What, no, um, no” Donna smiled and went back to her office. Smooth Bill, smooth. This went on for awhile. Conferences in her office. Wondering if that open button was an accident. Trying my best to make appropriate eye contact. Not being caught watching her ass as she left my desk.

Then one evening I was working some OT when Donna called me into her office.

“Close the door Bill.”

“OK, is something wrong?”

“I want to talk to you. You’re a good worker, reliable. I think you could move into this seat if I get promoted. But you need to work out a few things.

“What?”

“Well this is going to be unprofessional, but I want to help you be more professional. You need to better control your eyes. Make eye contact. I can tell when they stray as you’re talking to me.”

“No really, I’m not…”

“Yes you are. You don’t even realize. So now you sit there. I’ll sit here. Look me in the eyes. Listen to me.” So I sat as instructed and looked Donna in the eyes. I could kind of see her hands come up. She unbuttoned her top button.

“So as I was saying Bill, you are doing good work. You’re a nice guy.”

Another button. My eyes are locked in place. I wonder how far she’ll go.”

“The other members of the department respect your opinion and appreciate your help working out problems that come up.”

Another button. If I could look down I’m sure I could see her bra, the tops of her breasts. I can feel sweat on my forehead.

“Keep looking up here. Don’t let your eyes move. At no time when talking to a woman in the office should your eyes stray.”

Now I can’t see what’s happening down there. She must have opened another. Her hands pull her blouse open. But I can’t quite..

“You may not know, but half the guys who work on this floor have hit on me. But you haven’t. That’s a plus. But I like you.”

Looking in her eyes, I can tell she’s shrugged the blouse off her shoulders. I now have a raging hardon even though I’m only looking Donna in the eyes.

“I like you. And you’re doing great. Lesson learned I think. Now the final test.”

Her hands coming up again. At the front of her bra. Movement at the bottom of my vision. I’m going to have to look because I think her breasts are now free.

“Excellent. Now you may look. What do you think?”

“Oh wow, perfect.” Yes they were, large, firm, nipples sitting up. Yes perfect. And then for one of the few times I took a chance. I stood and came around the desk. I think Donna thought I was going to feel her breasts. She sat forward.

“Donna, that was a tough test, but could you pass the same?”

“What do you mean?” I stood before her.

“Look up at me. Right in the eyes.”

“OK”

“Keep looking.” I unbuckled my belt. Opened the button on my pants. “Eyes up here.”

“What are you doing?”

“Hmm, I guess you’re not cheating.” I began slowly unzipping my pants. Then I let them fall. “Very good. Now the last test.”

I hooked my thumbs into my boxers. Slid them down. My hard 6 inch cock now pointed at Donna’s face.

“You may look.”

“Oh, nice. Very nice.” Donna reached out and took hold of my cock. Feeling it’s thickness, stroking its length. She leaned forward, wrapped her lips around the head. “MMM.” Bobbing her head on my cock, stroking the base, weighing my balls, she sucked about half my cock into her mouth, then pulled back, then again. Sucking, licking. I held my hands on each side of her head. More for balance, not forcing her. She could feel me tensing. Opened her mouth, aimed my cock and stroked hard. Willing me to cum. She waggled her tongue at me, licked under the head then held her tongue there as I shot two, three full spurts into her mouth. Then sucked on my cock to get the rest. She swallowed, then smiled. “MM, tasty.” She noticed that I was still hard. “Oh, may I sit on your lap?” She stood. Before taking her spot I finally had a chance to take her breasts in my hand. I felt their weight, I licked and sucked on her nipples. Donna let her skirt drop to the floor then slid her underwear down, showing me a dark trimmed bush. I sat on her chair, she sat on me facing away, slipping my still hard cock into her wet pussy. She sank down fully on me and leaned her head back on my shoulder. I held her breasts firmly, squeezing, pinching.

“That feels nice. You feel good inside me.” The leather chair allowed for rocking, and bouncing. I held on tight, thrusting as needed. Donna bounced and rocked. Leaning forward, then back. Rolling her hips so that I hit the right spot. I’d already cum, so I was just along for the ride as she took advantage of my stamina to satisfy her needs. “This is good Bill. I work so much I don’t have time for this.” She was making time now. I reached with my left hand and found her clit. She was already there, but let me share.

“Oh yes, right there. Oh. Oh OK, put your hand over my mouth.” I used my right hand and cupped it over her mouth, trying to silence as much as I could as she came and tried to let the world know she was cumming. While holding the sound in I encourage more as I rubbed around her clit while she bounced on my cock. Coming down she stood and leaned over her desk. “Now. Give it to me. Fill me with your cum.”

I stood behind Donna, her bountiful ass before me, her tits hanging over her desk. I took hold of her hips and slid my cock deep into her wet pussy. Then I rocked back and forward sliding easily. Feeling her tighten on my cock, pushing against her ass as our bodies slapped together with each thrust. When ready I held on tight against her and gave her my second of the night. Exhausted I say back in her chair. She sat back on my lap.

“Final lesson. Never do this with someone who works for you. Fortunately I was promoted today to another department. I recommended you for this supervisor’s position. MMM, seems I could recommend you for a few things now.”

“Thanks Donna, for all your lessons.”

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