by J

Gender: Male
Age: 34
Race/ethnicity: Latin
Current location: Costa Rica
Highest education received: College degree (eg., BA, BS)
Occupation: Psychologist
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)? 7
How many hookup stories have you here posted before? 0

Sex With a Virgin Who Has a Crush On You

How long ago did this hookup happen? About a month 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…)? Fuck-buddies

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’s this cute and shy 24 year old girl I know from work. We became good friends but with time it became evident that she had a big crush on me (This was later confirmed to me by another co-worker who’s a mutual friend). I was in a stormy relationship at the time so I didn’t act on it because I didn’t want to complicate things in my life even more. But then my company sent me to another country for 6 months which eventually led to the end of my relationship. When I returned to my home country I noticed her crush was even more intense and that her hints towards me became a bit more spicy despite her shyness. We have similar tastes in books and music so we always have things to talk about and that was a good excuse for us to innocently tease each other. During this time I also learned that she was a virgin and this discovery caused some sort of morbid fascination on me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After heavy drinking during the office’s christmas party we ended up fooling around in her apartment. I was unsure about making a move because it’s always akward when you have an affair at work and also I was told sex with a virgin is not always a pleasant experience. But after that night we talked a lot and she told me she wanted me to be her first sexual companion, that she had decided she was ready and willing. So we planned the first night very carefully, I wanted her to be comfortable about every single detail and she was very excited about choosing her wardrobe, the lingerie, the wine, etc. She’s 10 years younger than me so we started and innocent game in which I was to be her teacher in these sexual endevours, which is exciting for me.

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 had dinner and some wine at her appartment. I could tell she was very nervous but soon we started making out and and getting rid of our clothes. At this point she was really aroused and so was I, so I went down on her. She was certainly enjoying these new sensations (she told me she never had an orgasm before), she was moaning and her legs were shaking. Then she went down on me, and even though she was unexperienced I was still able to enjoy it as she was making her best effort and had an incredibly attitude the whole time. After I came we took a shower together and then moved things over to her bedroom. I knew intercourse was going to be difficult the first times because of her being a virgin, so I made sure I show her a lot a patience and understanding (For instance, I gradually introduced my fingers and then the tip of my penis in her vagina in order to make the whole experience less painful). We used a lot a luv until I was able to penetrate her fully, which was really exciting, and even though she still experienced a bit of pain and there was some blood involved, she was anyways able to enjoy it and wanted even more the morning after.

Did you have an orgasm? Did your partner(s)? Yes, we both did. Multiple times.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We discussed STI history and also used condoms all the time.

What were your REASONS for having this hookup? Overall I guess it was really exciting to hook up with a girl who’s ten years younger and still on her 20’s, not to mention the fact that I get to teach her and she’s willing to follow my lead. Also my previous relationship was a real pain in the ass so I felt I needed some sort of relief.

Were alcohol or drugs involved? If so, how much? We had a bottle of wine that night.

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? We keep seeing each other at work but have kept everything between us (she’s very discrete). We talked before anything happen and agreed to keep this as a fuck-buddies type of relationship, as I was not looking for anything serious. She stated the same but I feel she might want more on the future so my plan is to end things before she gets too involved, emotionally speaking. We recently had another encounter which we both enjoyed a great deal.

To whom did you talk about the hookup? How did they react? Just a couple of friends and our mutual friend from work. They were really interested an curious about the whole story.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both.

Do you regret this hookup? If so, why? Not at all.

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 so far there’s no strings attached and also that despite her inexperience she has proven to be a woman who really enjoys sex with great attitude and is willing to try new things.

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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