Current location: New York City
Highest education received: College degree (eg., BA, BS)
Occupation: Financial Analyst
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 26
How many hookup stories have you here posted before? 0
Colleague Wanted To Please Me
How long ago did this hookup happen? 6 years ago
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? One night stand
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? 5’5″ 22 year old woman with dirty blonde hair and good physique.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went out drinking with co-workers on a Friday night, and at the end of the night 2 of them, a guy and a girl, came to my place and crashed. They lived in the suburbs and I lived in the city — they wanted to just wake up and drive home sober in the morning. I explained that I had a spare bedroom/bed, and a couch, and the guy went to bed really drunk and closed the door. I had no intentions of hitting on the girl — I was a few years older and was training her at work — she was hot but I wanted to maintain a level of professionalism. When I gave her a blanket for the couch, she said she didn’t want to sleep on the couch, and asked if I had a t-shirt and shorts for her, and if I minded if she bunked up with me. I agreed, but still somehow thought she was one of these weird girls who would actually just go to sleep or maybe cuddle, but that it was strictly platonic. I threw her clothes, got in my bed and turned off the light, and she said “don’t even act like you’re going to sleep”, and stripped down to her bra and panties…
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? After she said “don’t even act like you’re going to sleep” while taking off her clothes, I sat up on the edge of the bed, and she put her hand on my chest and knee between my legs. I could make out her figure in the dark, and it looked like she was staring at me seductively wearing just bra and panties. I didn’t want to make a move, but the sexual aura was obviously thick at this point, and I was drunk — I thought about resisting and telling her to just go to sleep — but I just couldn’t help myself. I put my hand on her hip, and pulled her close. She grazed her lips against mine, but wouldn’t let me kiss her. She bit my lip, pressed up against me, then stuck her tongue in my ear. She told me I was “so hot” and panted in my ear a couple times. I slowly raised my right leg in between her legs, and as my thigh pressed up against her pussy area she let out a light moan and her body tensed up. She leaned in and kissed me sensually, straddling me and taking off my shirt. My cock was rock hard and even though I was good in bed and had stamina, I felt like I was about to come in my pants. I took some deep breaths, and slowly began kissing her and took off her bra. Her nipples were hard, and her breasts were so perky and beautiful. I flipped her on her back, and the foreplay began. I began slowly rubbing her clit through her underwear while kissing her — sometimes pressing my tongue hard against the side of her neck. It seemed like she was suddenly maybe sobering up and was torn between stopping at this point, or completely unleashing. I could feel her get wet through her panties, and her body was tense. She was closing her legs and trying to slow things down — almost as if she her body language was saying “wait a second, what have I gotten myself into here” — but she was moaning and moving her hips slowly while on her back. I couldn’t believe how quickly things had progressed — we were both hot messes. I leaned back, on my knees, shirtless but with my dress pants still on. My cock was bulging through my pants — with some pre-come seeping through — and she began grazing it with her hand — almost like she was pretending that she didn’t know what her hand was doing. I felt like my cock was pulsating, dying to be let free — and she knew it. She grabbed my hand and began sucking on my finger — as if she was giving my finger a slow blowjob, which sent me into a frenzy. I assume we were both just moaning uncontrollably at this point but was in such a daze while in the throws of such an intense and unexpected sexual encounter to really know. I couldn’t believe this was the same girl I had been training and working with during the day who seemed so innocent. While on her back she kept sucking my finger, and I was dying to know what it would be like if that was actually my cock in her mouth instead. She was teasing my cock through my pants with more intent at this point. I contemplated just whipping it out, but really wanted her to go for it although it seemed like she was torn and resisting. Eventually, it was as if the flood gates opened and she couldn’t take it anymore either. Her light grazes made my cock grow more than I thought it could, and she frantically began unbuckling my belt. When she pulled my pants down, eagerly wanting my cock, the tip of it got caught with the pants, then sprung up, bursting through the opening in my boxers and exposing itself before I think either of us expected. I don’t think my cock had ever grown so big — I looked like a porn star. She immediately leaned up, entranced. She began stroking me and touching her lips on my cock while lying on her side, topless with panties on — and I was still on my knees. She would have made me come immediately had I not been drunk. My heart began pacing out of control and I was moaning uncontrollably. She was now sucking me, and I had to change something before I exploded all over her too soon. I pulled her panties to the side and began fingering her, going back and forth between putting my two fingers inside her and moving them in a “come hither” motion, and rubbing her clit. Her reaction was as if no one had touched her before. She began moaning so much she couldn’t keep sucking me. Seeing her squirm and moan drove me crazy — I quickly positioned myself to fuck her brains out — dying to feel her wet, tight pussy wrapped around my throbbing shaft. But she put her hand on my stomach to stop me and said she didn’t want to sleep with me on the first hook-up. I pulled her panties to the side again and was rubbing her clit. She was shaking and moaning — I laid down and she kept her head close to my cock. I began trying to pull her legs up to me, and lift one leg over so I could taste her soaking wet pussy. She kind of resisted, but once we were in the 69 position, I slowly pulled her panties to the side again, and began kissing her dripping wet pussy. She was moving up and down and tensed up — she couldn’t focus enough on giving me a blow job anymore, which wasn’t a bad thing because I was about to come and wanted this to last. Her pristine, tight pussy was on fire and incredibly sensitive. I began licking all over, and then focused my tongue on her clit while fingering her. She pulled her head completely off my cock and underneath moans I could hear “oh my god, oh my god”, before she went into a full-out intense orgasm for maybe 20 seconds with my cock half in her mouth. She pulled my cock back in her mouth, and I pulled it out, flipped her over, and aggressively began rubbing my cock all over her perky breasts — periodically pulling it up to her mouth. It was like I had transformed into a wild sex beast, and it seemed like she didn’t know she could orgasm like that, and was almost in a state of shock but still very much aroused. After rubbing my cock all over her face and breasts for a bit, she pushed me on my back, and pressed her hand on my stomach to keep me down. She paused to put her hair up, still breathing heavily, and the silhouette of her pausing in that moment to put her hair up to prepare for the work required to finish me off is forever branded in my brain. She ran her tongue from the base of my cock to the tip, and back down again. She teased the head of my cock with her tongue. I thought my entire body was going to explode. She slowly began giving me an all-out blowjob, using her hand and creating a hot lather all over my cock. She was moaning, and worshipping my cock in a way that would make you think it held the cure for cancer. As I got closer to coming, she began emphasizing the act of pulling her head back while my cock was in her mouth — like she was trying to pull up everything inside it — rearing her head back in quick motions. I had never experienced that before, and after 4 or 5 motions, I couldn’t control myself anymore. In a crazy, passionate daze I unloaded several massive ropes of come all over her. I believe it went in her hair, all over her face, her breasts, stomach, and all over the bed. She was watching my pulsating cock intently, rubbing her lips against it. When I was done coming, she wrapped her lips around my shaft a couple more times, then rubbed my stomach and chest, and kissed my cock one last time before we both passed out.
I had a hard-on all night I think. When I woke up, she was rolling over me to get water off the nightstand, wearing panties only, and felt my hard-on but didn’t react at first. Then she kind of straddled me, and rubbed herself up and down my cock for maybe 3 seconds, but stopped. I tried to fuck her several times before we got up, but she wasn’t up for it. She got out of bed first to go wake up the other coworker and get her day started, and while in bed I quickly masturbated and blew another huge load into my already come-filled sheets. I feel like she probably knows that’s what happened.
I cooked her, my roommate and coworker who spent the night breakfast — and then they left. It was a bit awkward but not too bad. We had been in the dark all night, and I couldn’t believe in the morning light that this was the same girl I worked with.
Things were a little awkward at work after that — at least for me. She was pretty cool about it, but I was just in awe that this smart, educated, ambitious, 22 year old girl-next-door type was capable of such a night of frivolous sexual adventure or that she knew how to turn me on the way she did — and then act completely fine at work. We never spoke of it, but she would give me flirty grins sometimes. I was trying to be a responsible professional at the time, and thought it was a mistake, so tried to just pretend it didn’t happen. We never hooked up again, and I left the company 3 months later. I haven’t seen or talked to her since, but I have to admit that I masturbate to the memory of that night often. Apparently she’s a powerful lawyer now. That experience changed the way I looked at everyday women who come across as completely non-sexual — when I’m on the subway and bored sometimes I just look at women on the train and wonder if they’ve ever done anything like that before — of if they’d secretly like to.
Did you have an orgasm? Did your partner(s)? We both had orgasms. I’ve never come so much in my life.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Nothing was discussed before or after
What were your REASONS for having this hookup? It wasn’t something I pursued — but there was obvious mutual consent once she made a move. We were both single, fairly drunk, and having fun/exploring our sexuality.
Were alcohol or drugs involved? If so, how much? A fair amount of alcohol. I think we both took a shot or two and were playing drinking games with beer at a bar.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? It was awkward at work, for me — she was actually cool about it. She gave me some flirty grins around the office sometimes, but we never talked about it and never hooked up again. I left the company 3 months later and haven’t talked to her since. She’s now a powerful attorney.
To whom did you talk about the hookup? How did they react? I told one of my friends. He was amazed.
Was this a consensual and/or wanted experience for you? For your partner? Yes, for both
Do you regret this hookup? If so, why? Hell no
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best thing about this hookup was how unexpected and forbidden it was — that made it unbelievably hot. It was like something out of a movie, and she was spell-binding. The experience changed the way I looked at everyday women who come across as completely non-sexual — when I’m on the subway and bored sometimes I just look at women and wonder if they’ve ever done anything like that before — or if they’d secretly like to. I now feel like all women have a sexual cat woman hidden in them, and getting them to unleash it is the greatest experience. I gained a lot of confidence in talking to women and hooking up after this experience. Sometimes I want to find another forbidden, unexpected sexual encounter, which can lead to problems in my relationships.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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