by Rock Climber Dude

Gender: Male
Age: 47
Race/ethnicity: White
Current location: Plattsburgh
Highest education received: College degree (eg., BA, BS)
Occupation: Engineering
Relationship status: Married
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)? 10+
How many hookup stories have you here posted before? 0

First Time

How long ago did this hookup happen? 25 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…)? Long term relationship

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? My girl friend of the time was a rhythmic gymnast who I met when she was 20 and I was 21.  Although she was 20 she still looked like she was 14 because of her gymnastics.  She was blonde with a pony tail, probably about 90 pounds, flat chest, very prominent hip bones, very tight abs and flat stomach and she had the most beautiful face.  She was incredibly flexible and she eventually went to work as a contortionist.
My parents were appalled when we first started going out.  They accused me of being a pedophile.  I had to point out to them that we met in university and she actually showed them her drivers license to prove her age.
Her looks were actually a problem for me.  We dated for almost a year before we started having a sexual relationship.  Her little girl look was difficult for me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Once we started having sex we made a point of having sex almost every day and often two or three times a day.  She was certainly the instigator.  She had a very high sex drive and I was actually very shy.
This particular time was at her parents home while they were away on vacation.

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? At this time we had been having a sexual relationship for almost a year.  Because she was so small and I was so big we had found that having vaginal sex was just not possible.  Mostly we enjoyed oral sex.  We both became very good at it.
Despite our size differences we tried having vaginal sex every day.  She would climb on top of me and see how far she could get me in her without it hurting.  Slowly month after month I could get more into her.
On this particular day we first started with oral sex and then after a while tried vaginal.   She was on top of me and going up and down and I was about 3/4 into her and all of a sudden I just popped all the way in!
She gave out a very surprised yelp and almost immediately had an orgasm.  I thought I had hurt her and started to withdraw but she clamped her arms and legs around me and said no.
“Oh my god, you’re all the way in me!”
We kept fucking and she had four more orgasms over the next two hours.  At this point she said “Cum in me!”
“I can’t, you could get pregnant.” I replied
“I just finished my period two days ago, it’s safe.  Cum in me!!!  I want to feel you cum!  This is your first time all the way in me and I NEED you to cum!”
For the last several months I had trained myself to keep calm and not ejaculate in her.  We didn’t use any condoms and she was not on the pill.  I also didn’t want to lose control and hurt her.  Now I was allowed to cum and I couldn’t.
We continued to have sex and over and over again I would watch her chest flush red and her come to climax.  She was desperate to make me cum.
Finally when she was coming her tenth time after about five hours of being in her she looked me in the eyes and kept on saying “Cum in me!  Cum in me!  Now, please oooooo…please…please…..cum in me!”  She was screaming and having another orgasm and clamping down on me hard.
I had the most incredible orgasm.
This was the first time I learned that there is a difference between orgasm and ejaculation.  Waves of sensation were pulsing through me.  I just kept on cumming and cumming into her.  It was fantastic.
Afterwards I stayed in her even after I lost my erection.  After a while I got hard again and came in her a second time.  This time it took a very long time and she had about ten orgasms over the next few hours.

Did you have an orgasm? Did your partner(s)? I had three orgasms and she had around 20.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.  We were both virgins when we met.

What were your REASONS for having this hookup? Long term relationship and we fully enjoyed each others bodies.

Were alcohol or drugs involved? If so, how much? Neither of us do drugs or drink.

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? It was very emotional for both of us.  Although we had been sexual for a very long time before this, it felt like she had just lost her virginity.  It was the first time she had a man all the way in her.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Yes, we both worked towards this for a very long time.

Do you regret this hookup? If so, why? Never. Although we eventually broke up we still meet for lunch and dinner once a year and we still have emotions for each other despite being married to other people.  She was my first and I was her first.
Over the years at times when we were both single we would meet and have sex.  Although we learned that we didn’t go well together as a couple, we always enjoyed each other in bed…or in the park….or in the subway….

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? After learning how not to let go, finally being able to just let myself experience her fully and let my body do what it wanted to do was incredible.
There were no negatives.
This gave me very high expectations for what sex should be like for the rest of my life.  It’s surprising how many women are actually really bad lovers!

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? I was very patient with my girlfriend and she was very patient with me.  Never was there ever any shame in what we did together.  It’s a good lesson for anyone.

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