by Lenny



Gender: Male
Age: 44/14 Then
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? Eight


My First


How long ago did this hookup happen? 30 Years

How would you best classify this hookup? First Time

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? Terra was a brunette, tall with long legs and a nice chest.  She was an older woman (16) and I thought she was really pretty.  We had grown up on the same block and had lived across from each other since we were kids.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Some background first.  I was an unplanned pregnancy of two college students, and my parents were not well liked.  Many of my neighbors growing up were racist and didn’t care for the white man with the Mexican wife.  Some of it was directed towards me including a bit from Terra’s parent’s.  It was a far different time in the eighties.

Now I had only really grown into puberty a few months before this, my voice was lower and I had hair down there and it was early that summer that I really started to notice girls.  Terra lived across the street and seemed to like to parade around in tank tops and tight shorts or in a swimsuit.  I had been watching her all summer.
Now it was one afternoon a few weeks before school resumed a group of us were at her patent’s using the pool.  Terra and I had always been friendly and for some reason or another we ended up in her bedroom.  She ended up kissing me and I kissed her back, I had never even kissed a girl before.  Kissing led to making out and I remember she was really jamming her tongue down my throat.

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? Things kind of just flowed and clothes eventually came off, I can remember getting quite a thrill when Terra took her bra off and I saw breasts for the first time.  There was a lot of touching and feeling each other, she played with my cock and I her breasts and felt her pussy.  It was also Terra’s first time with a boy.
She had condoms and we stopped to put one on.  I penetrated her and rode her for about ten minutes but it was quite painful for her and there was some bleeding so we stopped.  She then asked me to leave.

Did you have an orgasm? Did your partner(s)? Neither of us had an orgasm, I don’t think Terra or I even knew what an orgasm  was then

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used a condom but since neither of us had any sexual history STIs did not come up.

What were your REASONS for having this hookup? I had been admiring Terra for a while, was horny, and wanted to be with someone for the first time

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

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? Now Terra and I did not hookup again for many years, close to twenty actually.  Mostly right after Terra pretended like it never happened and once high school started I quickly hooked up with another student.  I did however look back on my first time as a formative experience.
A chance encounter on my visit home in my thirties reconnected me with Terra.  Without going into a lot of details I fell in love with her and she was wife number two, and we even had a kid together.  We were married six years. As she is the mother of one my children I will always  care about her but she is probably the most hostile towards me of my children’s mother’s. We split due to my infidelity.

To whom did you talk about the hookup? How did they react? Most of my friends were really impressed and quite jealous, I was the first one in my group to have sex

Was this a consensual and/or wanted experience for you? For your partner? Yes for us 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? Having sex for the first time, it was a big moment in my life.  Worst part was how painful the whole experience was for Terra.  As for casual sex and sexuality and myself, as I said this was my first sexual experience and opened me up to that world.  Since then I have had many partners, been married three times, have five children, three with wives and two outside of marriage.  As I said, this was a huge and formative moment in my life.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else? Thought I would share the story of my first time since this is the last post I will be doing for a while.

You have a hookup story to share? Submit it here!