What’s your gender? Man
How old are you? late 30s
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Canada
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Business Executive
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? enough to know what I am doing
How many hookup stories have you here posted before? 0
Sex with an Athlete.
How long ago did this hookup happen? 5 years
What was your relationship status at the time? Same as current status
How would you best classify this hookup? Fuck-buddies / Booty call
How long did you know the person before this hookup? For 1 to 3 years
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? She was about 25. Her name was Anita. We worked in the same office but we didn’t have that much contact with each other. I knew she was recently married – a couple of years – and did not have any children yet. I found her attractive enough but there was not any real sexual tension between us that I remember. In fact, other than being married I knew little else about her. She had a smallish but athletic build. She dressed semi conservatively so one never noticed how in shape she was.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The company we worked for had been recently been taken over. The acquiring company’s head office was in another province some 1000 miles away. Some of us, myself included, were being moved to positions in that head office. At the time of this story, I had already moved my wife and four children to a new house in the new province, sold our old house and was back in town signing papers and finalizing everything necessary to make the move complete.
I was making the rounds of the office saying my goodbyes when I was approached by Anita who asked, “where are you staying now that your house has been sold?” I told her the Westin in midtown, to which she responded, “I could meet you there this evening and we could have a last drink together”. I found this a bit strange since we had never had a drink together before, in fact had never attended the same social events. Nevertheless I went with the flow saying I had made arrangements to have dinner with some old neighbours and would be back to the hotel about eight that evening. She smiled and said, simply, “see you then.”
As it turned out dinner went longer than I expected and I didn’t get back to the hotel until 8:30. When I entered the hotel lobby I didn’t really expect her to be there, or still there – either she didn’t show or didn’t wait for me. Nevertheless, when I walked in she suddenly appeared from the shadows of the lobby somewhere and immediately gave me a big hug. I apologized profusely for being late and said, “there is a mini bar in my room, do you want to check out what is in it?” She nodded or otherwise gave agreement and we headed to the elevators. Now remember, I still don’t really know why she is there does she just want a drink, does she want to talk about something serious, or, as she says, “just say good bye.”
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end?
We shared an uneventful elevator ride to my floor, opened the door to the rented hotel space, at which time I immediately excused myself, saying, “check out the mini bar. I have to use the loo and get rid of my earlier beers”
I did my business and upon returning to the room saw Anita stark naked sitting on the windowsill looking our over the city. With her message was getting a little more specific I started taking of my cloths while she proceeded to the bed and started pulling back the comforter on the small but adequate hotel type queen sized bed.
Once down to the sheets she lay back on her elbows with her feet on the floor looking straight into my eyes but saying nothing as I remember. At this point I got my first surprises. Her clitoris was massive, or at least the skin part of it was huge. For a fleeting moment I wondered how I was going to find her “pleasure button” amongst all that skin. Undaunted, I got down on my knees and as I got close to her vagina got my second surprise. She had sprayed, or otherwise applied, perfume on her cunt. It was now crystal clear to me – I always was a slow learner – she was there for one reason and that was to be fucked. What was more she wanted or expected that the fucking might involve being eaten out and she wanted to make it as pleasurable for me as possible.. Totally unnecessary for me, since I have always enjoyed using my tongue on my partners. Especially the ones that pull me under my armpit when I go down on them. I always assume those are the women that needed it the most, have never had good tongue and need the experience at least once.
As it ended up, finding her clit was no trouble at all. Once down on her I separated her skin and began massaging her clit with my tongue and flicking it with the end of my tongue. By her involuntary hip movement and soft sighs it appeared my actions were being well received so I added two fingers and massaged her G spot as I flicked her clit with my tongue.
Now I don’t remember how long it took but it didn’t seem long until she had her first orgasm and as I learned later, her most powerful orgasm. It started as a slight quiver in her thighs beside my head. As it built she locked her ankles behind my head, grabbed tufts of my hair forcing my face into her vagina making it hard to breath, but not scary hard to breath. At that point I just rode it out as her body convulsed. As soon it subsided a bit and her vice grip on my head released a bit, I continued flicking with my tongue until I felt my hair being grabbed again the convulsions reoccurring.
Finally she relaxed, released my head from, the leg grip she had me in. I rose at this point and looked down on her. I am sure with cum juice all over my face and before I could ask “how did you enjoy that?” or some other equally stupid statement she looked me straight in the eyes and said “fuck me. I have been looking forward to this all afternoon. I soiled a set of underwear and skirt already this afternoon thinking about this. Now fuck me!”
As I went to mount her, she rolled over on her side and said, “No, I want to ride you”
Complying with her request I lay on my back on the bed while she mounted me and began to rub her wet cunt back and forth on my erection. After a short period of stimulation in this position she laid prone on top of me possibly kissed me slid back taking my penis into her vagina and then locked her feet around my legs. I had never experienced this move before but immediately recognized that it provided her with a lot of leverage as she ground her clit into my pubic area. Our bodies in effect became one. When either of us moved the movement was magnified by the fact that our bodies were so tightly bound.
Now I have had “cowgirls” jumping up and down on me before, but this locked, prone position was so much more pleasurable and intimate. As she ground her clit on my pubis I could sense she was experiencing continuous small orgasms. As she sped up her motion I could sense I was not going to last much longer. Whether it was my breathing or my sighs it was obvious she could sense it too. With that she reached between our hips; grabbed my balls and started to squeeze and massage me into one of the most powerful ejaculations I have ever had. As I came inside her, she cooed, “yes, yes; give me your babies; give me your babies.” Now this statement stopped me dead in my tracks. Give me your babies!? Had she come to get inseminated or was this just sexual excitement and meaningless vocalization. I quickly assumed the later and just lay back and enjoyed as her powerful vaginal muscles squeezed ever last drop of cum out of me.
We lay there, probably talked, but don’t know about what, as she squeezed my dick as I shrank, finally falling out of her pussy. At this point I explored her beautiful ass. While we were fucking I had grabbed it pulling her onto me and was impressed by how athletic it was. Rock hard with an indentation on the outer side of each cheek. Now I wanted to explore it so with my left had I started at the base of her vagina and lightly drew my fingers up through the crack of her ass. Each time, the tips of my finger would pass over her bald, smooth, warm anus, her body would quiver and she would squeeze her muscular cheeks together on my hand… This was obviously giving her great pleasure and excitement, so I continued. I soon realized it was exciting me as well, because within minutes I had another rock hard erection going for me, or should I say going for us. She obviously noticed too and in a voice that denoted surprise as well as anticipation she said, “I see you are ready to go again” – getting the feeling that she was only expecting one good round of fucking that evening.
I flipped her around, pulled her ass up, and placed a doubled up pillow beneath her stomach. Now I got to look at the beautiful ass that I was so in awe of. I immediately took my cock and entered her vagina, teasing and lubricating more than fucking her. Pulling it out I moved my cock up and down her ass applying a little added pressure each time I passed over her anus. Then I plunged deeply into her vagina. Although I got a bit of push back and a few gasps, I could sense this doggy style business was not her favorite.
I turned her over on the bed into a missionary ready position and went down on her once again with my tongue and fingers. At one point, coming up for I air, we made eye contact and she said in a somewhat forceful manner, “ I don’t’ want your fingers, I want you”, at which I pulled her legs up on my shoulders and began fucking as requested. However as soon as I started to enter her she placed her hands on my hips. This was seemed a protective reflex on her part. Now I am just your average 6 inch type dick, but she felt she needed the ability to push me away if she felt I was about to penetrate her too far.
Instead of deep penetration then I settled for somewhat more vanilla stuff. I lay down on top of her probably kissed her and began a conventional missionary fuck. But, as before, she locked her feet around my legs and we again became one. This time however, being on top, I appeared to be the one with the leverage. I took advantage of this and began osculating my hips and again rubbing her clit with my pubis producing small multiple orgasms for her.
As I indicated she was one for surprises and the next one took me totally by surprise. We had established a pretty good rhythm. As I mentioned before, in our “locked” position the slightest movement by either of us seamed be magnified. I would rise slightly and ram into her. On one of these up movements she flipped us over so I was on my back and she was on top. And what is more she did it without me so much as slipping out of her pussy. Now since I am 6’2” 220 lb. And she was some 5’4” and couldn’t have been more that 120lb. This was some feat. Sensing from her athletic body that she was heavily involved in sport, I thought maybe she is a female wrestler in her spare time.
It was obvious this was her preferred position so I worked with her to reestablish a smooth pleasurable fucking rhythm. I grabbed her beautiful ass cheeks and pulled her into me. I then moistened the middle finger on my fight hand. I placed it at the entrance to her anus and waited for a reaction. Immediately she pushed up to meet my penetrating finger. On each successive movement she would push toward my finger until it was in her ass past the second knuckle. At this point I realized why I was not a big fan of anal sex. My finger buried some 5 inches into her touched what was obviously shit stool. Nevertheless she was enjoying this and so I continued. Each time she came down on me and ground her clitoris into me she would squeeze my cock with her vagina and my finger with her sphincter muscle.
The cadence quickened, She moved faster and faster on top of me. I knew I couldn’t hold it and blew my load in her once again. With that, she let out a shout of “OH FUCK” and collapsed on top of me. Her vagina released its vice grip my cock. He sphincter muscle went limp. Her breath came fast and moist in my ear. I began to feel liquid all over my stomach, running down my balls and the crack of my ass, totally soaking the sheets. She continued to lie on me not saying a word and then slowly rolled off me onto the bed beside me with my finger still stuck up in her ass. At this point I slowly removed my finger noticing a slight sigh and twitch as it departed her ass hole.
And so ended our proposed evening of drinking and conversation with no drinks, little conversation but memorable sex. Did she want to go for round three? Did she want or expect some anal penetration? I’ll never know. She didn’t ask. I didn’t offer. She put on her clothes. We probably kissed. She left.
What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? Immediate questions of what did she tell her husband going out from the house earlier that evening and what did she say when she returned?
Did I leek out of her as she drove home soiling yet another set of panties and causing embarrassing, hard to explain, wet patches on her jeans?
Did she and her husband make love later that night?
What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None
How intoxicated were you? Not at all (no alcohol or drugs)
How intoxicated was your partner? Not at all (no alcohol or drugs)
How wanted was this hookup for you at the time? Somewhat
How wanted was this hookup for your partner at the time? Very
To whom did you talk about the hookup? How did they react? no one before recounting the evening on this site.
Did you get emotionally hurt as a result of this hookup? Not at all
Did your partner get emotionally hurt as a result of this hookup? Not at all
Do you regret this hookup? Not at all
What was the BEST thing about this hookup? The fact the room had two queen sized beds allowing me to get a good night’s sleep in a dry bed
What was the WORST thing about this hookup? Our limited time together and limited conversation
Anything else you want to add about this hookup? Years latter now, does she think fondly of the evening as I do and wish we could reconnect if for nothing other than the promised conversation that never seemed to materialize.
After the move, I left the company in question giving me no reason to be in contact with Anita.
I have never been back to the town I left. She seems not to be active on social media
One thing I did find strange that evening. She never once touched my penis
What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Good for sensitive people who take care not to hurt the feelings others either directly or indirectly.
What do you think about the Casual Sex Project? Looks like it can be monetized
You have a hookup story to share? Submit it here!