by Lenny

 

Gender: Male
Age: 44/17 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? Two

My First Blow Job

How long ago did this hookup happen? 27 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…)? One Night Stand/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? I’ll call her Alex, someone who will always be special to me.  In high school she was tall with long black hair and soft skin, and had quite an impressive pair of breasts on her even then.  She was a cheerleader and I played football.  I met her when we were freshmen but nothing happened between us until junior year.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was at a party at an abandoned campground which was a popular teen party spot until the police blocked the area off and started patrolling it heavily a year later.  We were only a few months into school but Alex and I had become friendly.  I played football but was an offensive tackle and Alex was a cheerleader but not the head cheerleader so we were popular but not the stars.  
I was at the party and had started talking to Alex.  I am a lot of things but never had been a heavy drinker and had only had one beer.  Alex and I had started making out and went off by ourselves, the campground was quite large.

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? Alex and were making out and I was really feeling her up and even was squeezing her breasts a bit.  I thought things were headed in the direction of sex.  Neither of us were virgins, as I said in my previous post I had been sexually active since fourteen and already had several partners under my belt.
Alex asked me to trust her and said I would like this.  She unbuttoned my pants and pulled them down and then began to suck my cock.  I had never had a girl stick it in her mouth before and it felt amazing.  She pleasured me until I came and I finished in her mouth.  She smiled a bit and was pretty proud of herself and used mouthwash to rinse her mouth out.
We did go again about an hour later.  We had put a tent up and were cuddling a bit and clothes came off.  Her breasts were huge and I licked and sucked on them a bit and I mounted her and fucked her.  We went our separate ways early in the morning.

Did you have an orgasm? Did your partner(s)? I did both times and Alex did when I penetrated her.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used a condom during the penetration.

What were your REASONS for having this hookup? I was young and Alex was someone I wanted to see naked

Were alcohol or drugs involved? If so, how much? I think a 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? Alex and I hooked up a few more times during high school.  In college my freshman year Alex and I lived in the same dorm, and we regularly hooked up.  We had a booty call type arrangement and would say looking back now we were in a casual relationship for a few months.  However early in my spring term I met the woman who would be my first wife so I ended things with Alex.
Now Alex and I did not end there, and there will always be a place in my heart for her and a lot of fun memories.  Alex and I hooked up at our ten year reunion and were not careful and I did knock her up.  She told me shortly after but moved away with my son a year later.  We also hooked up at my twenty year reunion even though she was married at the time.

To whom did you talk about the hookup? How did they react? Bragged to my friends who were impressed and I think a bit jealous.   Alex was considered really hot in high school.

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? My first blow job which was quite a formative memory and sex with a gorgeous girl I really wanted to be with.  I wouldn’t say there was a bad part.  Not sure this changed anything about how I feel about casual sex but I did discover I enjoy receiving oral sex.

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

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

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