by Do I really gotta?

Gender: Male
Age: 42
Race/ethnicity: White
Current location: TX
Highest education received: College degree (eg., BA, BS)
Occupation: Engineer
Relationship status: Married
Religious affiliation: Unitarian?
How religious are you? Somewhat
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Try-sexual
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 1

My Cherry, Mildly Traumatized

How long ago did this hookup happen? 27 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…)? Losing My Virginity to a 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? She was somewhere around my age, 14 I think, but she told me she was 20.
I had never met her before, even though we went to the same school. My best friend brought her over, wanting to play with my model train. This wasn’t unusual, I took it for code that he wanted a place to make out with the girl.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A bit unusual, he went and actually started tooling around with my train layout in the back room and left her sitting in my living room.
My mom was at work, and I was bored – so I had dipped into her vodka before they arrived. I certainly didn’t plan on company, much less sex.
She started flirting with me from the chair while I was in the hallway. She flashed me a boob in a black bra. Being 15, I immediately had a hard on.

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? Not to have her feeling “abandoned” in the living room, I invited her back to my room to listen to some music. We talked for a bit, perused the record collection, found something she liked, and started to make out. French kissing, feeling each other up through our clothes. Innocent enough, but very hot stuff for horny teenagers. haha
As clothes started to come off, I shut the bedroom door and turned off the light. I took her clothes off, except for her panties and she stripped me naked. We continued to french kiss and I began to finger her. She was wet.
I had a condom, but she wouldn’t let me use it. This wasn’t a problem in the moment. I pulled her panties to the side and stuck it in. It felt way better than I imagined, certainly better than my hand ever did. We kept it to missionary, I was a repressed Catholic boy and didn’t know of any other way.
About halfway through, my friend walked in on us and I yelled at him to go away and turn off the light. He congratulated me and obliged, awkward.
Afterward, we got dressed and went outside in the cold to smoke a cigarette, my first one in over a year (it took me 26 years to quit smoking again after that).

Did you have an orgasm? Did your partner(s)? She was counting her orgasms and made me stop after 10. I figured out later that I came 3 times without ever going limp. All were inside her.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No discussion of STIs, we were too young for it to really be much concern. I tried to use a condom, but she said it was a deal breaker so we didn’t use it.

What were your REASONS for having this hookup? 15 and desperate to lose my virginity. I think she found me cute and decided to go for it.

Were alcohol or drugs involved? If so, how much? I had perhaps a shot or tow of vodka before they got there.

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 talked on the phone for the next couple weeks. She told me she was “late”. I freaked out, later she claimed it wasn’t mine. That didn’t help. Eventually, I quit talking to her. I went for years thinking there was a mini me out there that I had no contact with.
We met up again at a funeral about 10 years later when she confessed there was no pregnancy, she just wanted to see my reaction.
We rekindled the friendship on facebook a few years ago, and it has been strictly platonic.

To whom did you talk about the hookup? How did they react? I didn’t talk to anyone about it except my friend, who had first hand knowledge anyway, and later my priest. I was too ashamed and embarrassed to tell anyone else, she wasn’t my type. And I was foolishly worried about my keeping up my “rep” at school, not my best behavior.
She told anyone in school who would listen about us hooking up, but at least it was “positive”.

Was this a consensual and/or wanted experience for you? For your partner? Of course, otherwise it would be rape.

Do you regret this hookup? If so, why? I regretted it more at the time than I do now. There was no love in this hookup, just lust. Now I realize I could have done worse for my first time.

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? Best: Surprise sex, and good sex at that. She had a really nice pussy.
Worst: Her panties chaffed me pretty badly, and she played with my emotions about being a deadbeat father for more than a decade.
This hookup lowered my inhibitions around sex and showed me it was ok to enjoy the act. But also brought home the possible consequences and the need to take precautions.

All things considered, how POSITIVE was this experience? Somewhat positive

All things considered, how NEGATIVE was this experience? Fairly negative

Anything else you want to add about this hookup or anything else? She is now living life as a man and I am very confused about how to handle this.
I never know if I should call her by the name I know her as, or do I call him by the name he gave himself?
I don’t think I turned her gay, sure of it in fact. But it is still weird to think that my first is now a man.

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