I have never met a man or woman as confident as the young woman who took my anal virginity. She was not dominating, or arrogant, just very confident in herself and her judgments of people. How she knew a guy like me would give her what she wanted, and what I learned to want, I still do not know.
We met when I was doing a work survey of a local university to add some decorative pieces to the administration areas and the student union’s offices.
I had started up a specialty business to do singular pieces of metalwork when I was 25. I later added decretive woodworking for fireplaces, exteriors of buildings, and eventually general interiors. I am 5’9″, now 42 years old, and in very good shape for my age.
One Tuesday night around 1 am, I was at the university to do measurements for the bids I was preparing when I decided to get a snack from a vending machine. I turned a corner near the student union’s relaxation area and met Robin by almost literally walking through her. My first impression of her was that she was Asian, cute, my height and her chest was nice and soft when compressed against mine before she went flying onto her rear.
“Sorry, I didn’t mean to run into you!” was what blurted from my mouth immediately as I stood staring at her. I was mesmerized for a small eternity before I was able to hold out a hand to help her up.
I tried to frame a real apology while my mind ate up the details about her. That she seemed to be about my height, perhaps 5’8″. Lush, dark, shoulder length hair framed her cute Asian features. My eyes dropped unconsciously downwards. Her breasts were C cups, and appeared large for her thin frame.
A short black skirt of some light blend swayed and flowed with her movements, as she rose. It had covered the upper parts of her thighs so far, but left the rest of her firm, stocking covered legs exposed. The absence of shoes helped explain why I had not heard her come up the cross corridor. Her age was a bit uncertain but my best guess was around 23, almost 20 years my junior.
I won’t bore you with my conversation with her that night, my side of it was very inane and, I have no clue to this day why she did not just walk away from my dumb-stricken face. It wasn’t until a half hour after the unexpected conversation broke up that I was able to sort out some of what she had said to me.
Her name was Robin, she was actually 22 and was born locally to parents that had moved from Japan about 25 years ago. She was the secretary of the student union, in her 3rd year of university studying mathematics. Her intelligence, confidence, and humor about the situation shone through my confused memories like a beam of sunlight through a cloudy winter sky. She told me, she was working late on both homework and some of the student union work. She mentioned she would be there most nights this week.
I had told her about what I was doing, a bit of my background, and that I would also be there also several times over the next few nights. From that came an invitation to stop by at the student union the next night and spend a bit of time with her. Reviewing in my mind what I remembered she said, I was sure that she knew how instantly physically attracted to her I was, and how charmed I was by her personality by the time we said goodbye that night. I wondered just what would happen the next night.
Wednesday went by extremely slowly, it took until around 10:30pm to do paperwork that normally be done by 4pm. I had never been so interested by a woman, and the more I went over the memories of the previous night the more I was sure it was not just her body that captivated me. I went home to shower, shave again and get dressed in something nice but casual. I did not want to spook her by overdressing for a casual chat. I thought it was likely scary enough for her to realize a 42-year-old man was enchanted by her. I was about to find out that I would be the scared one.
I know its not the acceptable thing for an older man like myself to be interested in anyone that young, and I would never have looked for someone like her, its just that lust and love does strange things to the heart.
When I got to the university around midnight I barely remembered to get the pack with my measuring tools and notebooks out of the car. I headed immediately up to the floor the student union was on.
The front of the exterior office was a series of floor to ceiling windows with a door and several columns set to divide them. The office looked out onto the floor of the largest of the student recreation areas scattered across the campus. I could see part of the front room was dark as I walked towards it from the east corridor and my disappointment was acute.
But when I reached the windows near the door I was able to see the light in one of the interior offices. I knocked on the door and she came out to unlock it for me. With the light from the recreation area shining past me I could see the long, dark blue, cotton dress that she was wearing, and how wonderfully she filled it.
She waved me in after unlocking the door, and said “Hello, come in! How are you?”
“Hi Robin, I am fine, how are you tonight?”
“Tonight is going great, I managed to get ahead on both school work and a list I have been making up for the student union.”
She left the door unlocked and started back to her office, I followed a bit slowly, distracted by the sway of her hips in the low lighting. I did not know the layout of the office and had to follow her path to avoid tripping while my eyes adjusted a bit more. When we reached her office she stood beside her desk with its soft lighting lamp, while I stopped beside a chair facing her and let my pack rest on the floor.
She then stunned me by asking one of the most unexpected questions I have ever had from an almost total stranger. “Do you want me?” she said.
All I could do was gape at her at first. Before I could even think of dissimulating that no I just wanted to talk, my head jerked up and down in a quick nod.
Robin asked, “What would you do to have me? I don’t just give myself to anyone. You will have to prove to me that you want me.”
There was no doubt in my mind what the answer would be, “Yes” I said.
“Strip down.” was her reply.
I took off my shirt slowly, a bit stunned at what I was doing. The shoes and socks were a bit awkward, but my pants flew off. I hesitated with my hands in the waistbands of my boxers, but in a moment they join the rest in a pile to the side. My penis was just starting to fill with blood. I might have been uncertain but it was more than willing.
I was standing naked in the bright office light with a clear view through the exterior office to the hallway as she approached me. She kissed me lightly a few brief moments. And then lightly lead me by the arm to a chair beside the desk where she had me sit down.
I sat back the way she wanted me to, with my butt at the front and my shoulders touching the back and my head tilted back. I heard a bit of movement of the desk drawers while she slowly rubbed one hand up and down my cock. The slightest touch had it hardening. When she started rubbing it things went swiftly to solid thickness and I felt slightly dizzy on how fast this had happened.
Her lips slowly wrapped around the head of my cock. One hand firmly held my shaft while her other traced butterfly light patterns across my testicles. Soon her fingers ran down the path between my testicles and anus teasing the muscles there before doing small scratches and tickles at my rosebud. One finger felt moist and strange for some reason but despite my curiosity I kept my head tilted back to the ceiling, as she wanted. Only later did I learn she’d put a lubricated condom on one finger.
The one finger slowly started to press against the muscle keeping me closed. Surprisingly I trusted her and was comfortable, though still somewhat confused. The pleasure from my glans distracted me as the questing finger entered me. I’d heard of things like a finger in the ass during oral sex but never been with a woman who had liked it. Her finger slowly plunged in and out, maybe half an inch at a time. With the muscles relaxing and accepting, it started to go deeper, ever deeper. After a minute of this I all of a sudden trembled as her finger touched my prostate and caused a sensation to go through me. She must have worked her finger its full length into me.
Her finger slowly fucked my ass as her gorgeous lips were doing with my penis. She bobbed deep a moment engulfing me totally, and removed her hand from my shaft. She used her left hand to help get a second finger into the condom, her arms brushing my thighs as she adjusted it. Slowly she worked in the two fingers. Another minute and the third made a triangle penetrating me. All the while her she never let me out of her lips completely.
The constant bumping, touching and caressing of those fingers on my prostate while her lips and tongue caressed my cock was too much for me after a minute more of this. It wasn’t a violent orgasm but it felt so long and exquisitely drawn out of me that I felt like I was a puppet who’s strings had been cut, to lie limp in this chair. She waited a moment after I was done and then slowly eased me to the floor beside the desk with just quiet touches directing me.
I could barely look up when I heard the rustling of her dress falling but the beauty revealed drew my attention. She slowly took it all off, to reveal that she hadn’t chosen to wear underwear tonight. Maybe she was so sure of my reply that she’d taken it off earlier to relax and prepare. Her body was an exquisite masterpiece of silky smoothness and rounded curves.
She reached over and pulled something she’d placed on top of the desk while I was in the chair. It was a small, almost g-string harness with 2 dildo’s attached and a cord to the side. One small four-inch dildo faced inwards with a thick stem to it. A second seven-inch dildo stood out from the harness. She put that on while I watched. I wasn’t sure what my emotions were, they were rolling through me so fast it was hard to concentrate on anything but her slowly stuffing the four inches inside herself.
She grabbed what looked like another harness and dildo then walked over my supine body to a patch of bare carpet where she slowly laid herself down. She just looked at me and I started to crawl over to her. Her hands guided me to sit lightly on her stomach while pulling out a tube of KY from the bundle with the other harness. Slowly lubing up her strap-on’s dildo with one hand and rubbing jelly onto my semi hard penis took only a few moments.
A small push against my stomach had me slowly scooting back, easing her thin long dildo into me the pain and pleasure were mixed but the pleasurably stuffed feeling was winning out almost immediately. I must have backed four inches into me before slowing down. The head of her dildo tapped my prostate as it went by.
I still don’t know how I let myself be settled there to ride her cowgirl style, but I think it was that quiet confidence and her beauty.
She reached out to the other harness and dildo. It was smaller in some ways and much different when she unfolded it. It seemed to be a mask with a set of straps to hold it and a five-inch dildo projecting. When she slowly put it on over her mouth I understood how it was worn. She reached up with her hands and gently drew me to her.
My mouth slowly engulfed the dildo on her face. I felt like gagging a bit but it wasn’t much different from my old drinking contests of holding my mouth and throat open while friends poured liquor in. I felt utterly possessed by her. She was in my ass and mouth, holding me to her gently with a hand on my back. Her beautiful eyes locked mine to hers.
A small push and I was rocking forward and back on her dildos. The strap-on in my ass would penetrate me five to seven inches while the one in my mouth had its tip at my lips. Then I’d move forward and feel that pleasurable void as the one in my ass withdrew. She bounced her hips to fuck me harder and to make the dildo inside her move. The harness moved away from her a bit when I bounced away, drawn by my how tightly my ass held to her cock. It pressed against her when I plunged back onto my impalement.
Her small, gentle hands were busy. The left reached down to the harness to push and pull it and the dildo inside her. Her thumb flicked my testicles lightly every few strokes with a randomness that teased.
The right hand reached out and grabbed the cord attached to the harness. A small battery activated a light vibrator over her clitoris. She then reached down to my penis as it occasionally rubbed against her stomach depending how I arched myself. Holding the head of my penis away from my body and tight to her, she used my precum to break a trail across her soft and smooth stomach for it to follow.
I don’t know how long I rocked on her back and forth. I know she had several small orgasms at least from the way she tensed and bucked into me but time seemed meaningless as I concentrated on the sensations and her eyes. Soon, though it felt much too fast, I found myself building up to an orgasm. She seemed to approve and stoked harder into me with bucks of her waist and occasionally her head.
I felt my first spurt come forth onto her stomach. I tried in a frenzy to time my thrusts down onto the dildo in my ass, but the contractions inside me came too fast at first. With the pressure on my prostate and the way I continued to come for so long. A second peak of pleasure sent trembles through me, I felt a third smaller peak as through I’d had three orgasms during that long pleasurable moment.
We lay there connected together until we were able to recover, after minutes, from the experience. I took my mouth off her face dildo and pressed my cheek to hers as she held me. She took off the mask to kiss me gently on the lips. She started to nibble on my neck as she slowly eased her strap-on out of ass.
I don’t know if any passerby saw what happened that night but I know I never cared. I’m sure some have seen us on the deck of our pool on warm summer nights. We enjoy a wide variety of sex, but often we re-enact her taking of me with many variations on the theme. We’ve done it outdoors while camping, at my office, and more staid places like our living room floor many times in years we have lived together.