by ivorybill

: Male
Age: 46
Race/ethnicity: White
Current location: United States
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Legal
Relationship status: Single (then)
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Romantic interest in women; some bi-curiosity with men
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Saw Our Chance & Took It

How long ago did this hookup happen? 10 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? S was 30 year old woman working for a UN agency in a Middle Eastern country. I got to know her because we both worked on the same project for about a year. She is from a religious family in a culture where dating isn’t allowed, and marriages are normally arranged. She was under a lot of pressure from her parents to marry, but had always refused and insisted on making her own choice. She is very smart, with dry sense of humor, an expressive face and a nice laugh. She is of average height and weight, and although dressed modestly, you could tell she had a nice body. Her family was of Persian origin, and she had glossy straight black hair (usually hidden by her scarf) and pale skin. I definitely had a bit of a crush on her, but I would never think of trying to start anything with her because in her culture a romance with any guy, let alone a foreign non-Muslim, would cause her family to disown her, or force her to marry and leave her job.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We both went to a meeting in Europe at a UN agency. Her family unexpectedly gave her permission to make the trip. I arrived from the US and she arrived from the Middle East. We stayed at the same hotel. That evening, we went to dinner together, and then walked through the city.  I felt a mutual attraction, but I was too shy to make a move and it had always felt wrong. It was winter in Europe, and cold, so couples were walking with their arms around each other. She made some comment about how nice that was, that nobody cared. We get back to the hotel, and get into a tiny hotel lift to go up to our rooms. She’s cold and leans against me for a moment as the lift starts, and I put my arm around her.  She doesn’t resist but she doesn’t look up at me or lean in for a hug. The lift stops. I impulsively say “I’m in room 605… if you want” as I exit the lift.  Our eyes meet. She looks shocked. I feel like a jerk. I go to my room and lay down on the bed clothed. It was such a pleasant evening and I wanted to fantasize about her, but I couldn’t relax because I was worried that I’d stepped over the line.

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? I heard a knock on the door about half an hour later.  I opened the door and before she came in she said “OK, I want to play around, but I am a virgin and you cannot go inside me. You have to promise.”  I promised, and said something like “You decide what we do.” We agreed that nobody would ever know.  We kissed, and it felt electric. She said something like “I need this, you have no idea”.  We sat down on the couch and kissed. She was a great kisser. I felt her breasts through her clothes, and after a while, she says “let’s get undressed”.  As we undress it becomes clear that she has a woman’s body, with nice symmetrical medium-sized breasts and wide hips and a dark fertile triangle of a bush.  I’m sexually attracted to women, not little girls, and was glad to see she was unshaven.  I’ve also lost my clothes, and my penis could not possibly get more erect. She stares. “Have you never seen one of these before?”  She says “Just on little boys” and laughs.  I’m 6”, average length and quite thick. “Can I touch?” She touches me and says “The skin is so soft! It’s so strange!” We kiss again and hug, and the skin-to-skin contact feels so good.  My penis is pushing against her stomach, and her lovely breasts are pushing against me. I slide my hand across her stomach and then down into the gap between her legs. She draws in her breath. She was very wet. “They didn’t cut you?”  “No, my parents refused, thank God.”  I suggest that she let me use my mouth on her, and she admits that she’s heard of this but wonders whether I actually like to do that.  I assure her that I do and she says OK. I lead her to the bed, and she lay back. I kissed and licked her nipples, and then along the midline of her belly, gradually working my way down.  She spread her legs to give me full access; the time for modesty was past.  I kiss the inside of her thigh and then flick my tongue on her labia. She jolted.  I use my whole mouth and tongue on her, varying the pressure.  She began to giggle and then shiver and moan and toss her head back and forth on the pillow, and push her pelvis against my face.  After a few minutes, she got louder, had an orgasm, squirmed and laughed. After she recovered a bit, she sat up and touched my penis, and said “So what do I do with this?” “You could take it in your mouth.”  “If I take it in my mouth can you control yourself?  I’m not ready for you to squirt in my mouth!”  She moved her face closer to my penis, and squeezed it gently.  A drop of pre-cum appeared.  This kind of grossed her out and she said  “I don’t think I can do this yet!” I laughed. “Maybe you can just use your hand.”  I got a little hotel lotion bottle, erect penis jiggling as I walked.  I squirted some lotion in her hand and lay on my back, and guided her hand on my penis, showing her how to stroke it up and down.  She was leaning over me stroking me and I reached up and felt her breasts, with their symmetrical dark nipples. She said “I like doing this!”  I felt the fullness and slight pain in my testicles from being erect since she came into the room, and had saved up for a few days, so I knew that I would have a big load. “OK, now just pump the shaft, not the tip.  The tip gets more sensitive as I get close.  OK, a little more…” I felt the tightness increase until it was just unbearable. I ejaculated four or five ribbons of semen onto my chest and belly.  She yelled with surprise and laughed.  We snuggled together naked, and before long she felt me getting hard again against her body and said “What I really want is your penis rubbing against me, without going inside.  I want to feel our bodies together. I want to get as close as possible without you entering me.”  I went down on her again for a while, and then lay back with my erect penis lay flat against my stomach.  She straddled me and moved her wet pussy back and forth over my shaft, slowly, and then faster.  I wanted to enter her more than I can say, and she would probably have agreed because we were both so horny.  But this is her night and I don’t want to give her any cause for regret. I especially don’t want to hurt her and suspect that the first time must be painful. Also, if I entered her the temptation to finish inside her might be too much, and we had no birth control. The problem is soon solved: she has another orgasm and the sight of her in ecstasy is more than I can handle.  I ejaculate hard, and leave white drops clinging to her dark bush.

Did you have an orgasm? Did your partner(s)? We both had two orgasms.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We did not discuss STIs.  She was a virgin, and I had not been involved with anyone for a while and have always been very careful. We engaged in low-risk practices.

What were your REASONS for having this hookup? I did this because she was beautiful, smart, and I had a big crush on her, and I was horny. She did this because she was 30, a virgin, and her culture restricted her from experiencing normal healthy sexuality. She said to me “I want to do this so badly, you have no idea”.  I think she also felt some emotional attachment to me.

Were alcohol or drugs involved? If so, how much? No drugs, no alcohol

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? She didn’t want to spend the whole night because she was worried if her parents would call and she would feel guilty talking to them with me beside her. Also, she did not want anyone to see her leaving my hotel room. We talked and we knew that this could not go anywhere.  We lived on different continents. If this were to have a future in any public way, it would have to lead to marriage, and we were not willing to make that commitment. She got up, dressed, and we kissed again, and I checked to see if anyone was in the hall before she left. We had breakfast together the next morning.  I checked in with her and she felt the same as I did – very glad that it happened, but bittersweet because we did have a pretty strong emotional attachment to each other, and we knew it could not become more than that.

To whom did you talk about the hookup? How did they react? I didn’t talk to anyone about this.  I doubt she did, given the risks she would face.

Was this a consensual and/or wanted experience for you? For your partner? Both of this wanted it to happen. We checked in during the whole time to make sure that each of us was comfortable with what the other was doing. Consent is everything – she would never have done this if she didn’t trust me. Honestly, I would have loved to have entered her, and I think she was tempted, but I was not going to try to convince her because she might have regretted in later. Also I wanted her first experience to be as pleasurable as possible and since she was a virgin, I wanted to be sure to do things that would not cause pain – physical or emotional. We stuck to our original agreement.

Do you regret this hookup? If so, why? I do not regret it at all. I remember it so vividly years later as it was one of the best sexual experiences of my life.

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 is that I was a little bit in love, which made the sex even more physically and emotionally satisfying. The worst thing about it was that I was a little bit in love and, in a more perfect world, I would have liked to see where it would lead with her.

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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