by Lenny

Gender: Male
Age: 44
Race/ethnicity: Mixed
Current location: Columbus, OH
Highest education received: College degree (eg., BA, BS)
Occupation: Personal Trainer/Own a Gym
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)? 100+
How many hookup stories have you here posted before? Five

Her First

How long ago did this hookup happen? 26 Years

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…)? First of More

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? “Ellie” was the younger sister of a football teammate.  I didn’t know her or her brother well but he and I had played on the same team for three years.  Ellie is almost four years younger than me.  A few weeks before school I was over my teammate’s house watching a movie when Ellie came in.  I hadn’t seen her in a while and she was wearing a tiny pair of shorts and a revealing tank top that showed a lot of cleavage and her belly button, I think it was a bit more than Ellie realized  I noticed she had developed hips and quite a large pair of breasts over the summer and now she had the attention of most of the guys there. I thought she was really hot and became determined to fuck her.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I am not sure why this sticks out as one of my most memorable sexual encounters from High School.  I had been sexually active since I was fourteen and by senior year I had already had ten different partners.  Ellie was hardly the first girl that had caught my attentions and interest.
Now I didn’t get with Ellie right away, it took a few months.  Her first day of school I was polite and helpful with her, and she was in one of my classes.  I was friendly and polite but Ellie also had the interest of several other guys.
In November I invited her to a party at a teammate’s house and as a freshman she was quite flattered.  She had also just turned 15 meaning I wouldn’t get into any sort of trouble.  She showed up in a short little black skirt and tight, revealing top.  At the party we drank a little, danced, and flirted. I kissed her and we left to get some privacy and went to my parent’s travel trailer.  They never used it and Ellie was neither the first nor last girl I brought here and I had a stash of condoms.

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 locked the door and we started making out. She said a few times she had never been with a boy before. She asked me to take my shirt off and I did and she removed hers and then her bra and I got my first look at her breasts.  I sat on a chair and Ellie straddled me and I buried my face in her breasts and licked and sucked them which we liked.
I did this for a bit, and then we got naked.  We stood there just looking at each other and she wanted to play with my cock.  She did a bit, not that I needed it since just looking at her got me hard. We finally ended up on the bed making out naked.
I sucked her breasts a little more, and then penetrated Ellie.  I rode her for a while and after a bit she got really sweaty and her skin was flushed and her eyes were rolling back in her  head and she started moaning loudly.  Ellie asked me what was happening and I told her she would like it, she was having an orgasm and didn’t realize.  Afterwards Ellie told me it was amazing.  I came a little after she did and we cuddled for a while after and talked a little, but we soon fell asleep.  In the morning she dressed and snuck home.

Did you have an orgasm? Did your partner(s)? Yes we both did.  I was quite proud of it, I had only had a girl experience an orgasm one other time when I was with her before this.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used a condom to be safe but was unconcerned as Ellie had never been with anyone.

What were your REASONS for having this hookup? I was a horny teenager and Ellie was someone I wanted to be with.  I also think part of me wanted to take her virginity.

Were alcohol or drugs involved? If so, how much? One Beer each

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? Ellie got in trouble and was grounded for a month for being out all night.  We hooked up a few more times during high school and during both my winter and spring breaks my first year of college.  We also hooked up both during and after my first marriage (infidelity was a big part of the reason for the divorce).  I lost contact with her for a few years after Ellie graduated college but we reconnected and I even dated her for about eight months between my second and third marriages, her job got in the way and we split up. I went from a guy she hooked up with a bunch over the years to an ex, and Ellie lost interest and I haven’t heard from her since, this was about eight or nine years ago now.  
I look back on my time with Ellie fondly and recently heard she was married, and honestly I am happy for her.

To whom did you talk about the hookup? How did they react? Bragged a bit to one of my teammates but never really told anyone other than him.  He was impressed

Was this a consensual and/or wanted experience for you? For your partner? Yes to 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? Finally being with someone I really wanted was the best part.  As for the worst part there was no bleeding and it wasn’t really painful for Ellie so I did wonder if she was actually a virgin.  She later told me she had torn her hymen years ago.  As for how this changes how I feel about casual sex or sexuality, I do wonder why of all my high school hookups Ellie is the one I remember clearest.  Maybe it was because we hooked up a bunch of times into adulthood.

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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