by Pilot2B

Gender: Male
Age: 55
Race/ethnicity: Caucasian
Current location: Louisiana, USA
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Retired Military Officer
Relationship status: Married
Religious affiliation: Agnostic
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Strong Sex Drive, Adore Women
How many sexual partners have you had in your life (including oral sex)? 51
How many hookup stories have you here posted before? None

Flight Training

How long ago did this hookup happen? 29 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…)? Fuck-Buddies

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 had just completed Officer Candidate School (OCS) and was living on base just starting ground school for flight training. Trying to stay in shape after OCS I would go running and while running I met a women who lived next door who was a nurse that also just finished OCS. She was about my age 26/27 at the time, she was divorced with two kids. She was in good shape from running and very thin with a boyish figure about 5’4″ tall.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My then wife and I just had our first child and had gone home to visit her family 2,000 miles away. While running I told this women that I had to study for ground school and she offered to help. I suggested that she come over to my apt since my wife was away. She came over about 6pm wearing a pair of light color jeans and a light pull over blouse. Looking back I was flirting but she was on the hunt.

She helped me to study by quizzing with questions from the flight manual that I was studying. After about an hour she asked me if I would like a back rub, she was a nurse so I figure that she knew how to give a good back rub and said yes. She asked me if I had any lotion, I said yes and retrieved it from the bathroom.  I took off my shirt I laid down face down on the rug in front of the sofa we were 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? She did a great job of rubbing my back and then asked me to turn over so she could massage my chest. As she reached down and started to massage my muscular chest I could see desire in her eyes. I reached up and pulled her blouse and her camisole over her head. We were now both topless. I pulled her to me on the floor and kissed her as our bodies joined. She had almost no breasts with medium sized nipples. After a few minutes without talking I unbuttoned her jeans and pulled them past her boyish hips along with her panties. Next I removed my pants and pulled her towards me with one leg over my hips. I was hard as a rock since I had not had sex in long time and slid deep inside her. We fucked on the floor for a few minutes without talking and I then suggested we go to a bed. I took her hand as we separated and led her to my bedroom. She laid down on the bed and I climbed on top of her and mounted her in the missionary position. She wrapped her slim legs around me as I stroked in and out of her. It was warm and humid and we were both soaked in perspiration, very sexy. After about 15 minutes I asked her if she was going to orgasm, she said that she was too nervous but that I could cum inside of her since she had her tubes tied. That was all I needed I told her that I was going to cum hard, I pushed deep inside of her and spewed a big load in her vagina as I had not had sex in a while.

I felt great afterwards but I think she felt a little guilty so she said that she had to go home. But we did agree get together the next day to go to the beach.

We met the next day and went to the beach. We did not speak much during the ride. We set up our blanket in a location without anyone else nearby and went for a swim. After the swim we laid down on the blanket and I pulled her towards me and kissed her. She reluctantly kissed me and said that she did not want to break up my marriage. I said that I understood and that I was just looking for a friend and not to worry as I would be moving after Flight School.
We went back to her apt after the beach. When we were in her apt I pulled her to me again and kissed her. She kissed me back and said that we could have sex again but she did not want me to think that I could just come over any time to have sex. I said that I understood, her kids would be coming back from visiting her folks and my wife would also be coming back. She led me to her bedroom, she removed her one piece bathing suit and I removed mine. We climbed onto the bed and continued kissing. This time I laid down on my back and pulled her on top of me. I took my hard cock in my hand and started teasing her by rubbing my bulbous head up and down her wet slit. This time she was less nervous and really getting into it. I kept rubbing her with my cock and teased her by not letting her slide all the way down. Just as I was about to remove my hand and slide all the way into her, she has a huge orgasm. During her orgasm I slid all the way up her vagina and started pumping. After a few minutes I shot a huge load up into her.

Did you have an orgasm? Did your partner(s)? I did first time, she didn’t she was too nervous. We both did the second time.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None, we were both in the military at the time and tested routinely for HIV. She had her tubes tied and could not get pregnant. It doesn’t get any better.

What were your REASONS for having this hookup? I was horny not having sex for months, my then wife was refusing me sex after the birth of our first child. This was after the doctor said that we could. I had/have a very high sex drive.

Were alcohol or drugs involved? If so, how much? None

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? I felt great, I needed it bad. My only expectations were that given the opportunity that we could hook up again. I knew that it would be more difficult when my wife returned and that I would also be transferred after flight training. We remained friends until I transferred, but were not able to hook up again.

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? Consensual for both.

Do you regret this hookup? If so, why? No, not as it was great. I needed the sex. My wife decided that after our first child that she was not interested in sex. I met someone who needed sex just as much as I did. Funny thing is that I think that she felt guilty and she was the one that started things by offering and then giving me a massage. My only regret was not being able to get together again as she was getting more comfortable having sex with me.

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? I love sex and I love women. With my sex drive there is no way that I could stay celibate in a sexless marriage. This was the first of a many hook ups before I eventually was happily divorced :-)! I actually hooked up with an old girlfriend on the way to my next duty station about two months later. After all these years I enjoy remembering the experience especially realizing after the fact that she was the aggressor. I love being able to have hot sweaty sex finishing inside a women. This being the first time that I successfully had sex outside my marriage without consequences, gave me confidence for  future opportunities.

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? Just to add while my marriage broke up, it was not directly due to my sexual relationships outside my marriage, there were other larger issues. I guess one could argue that we lost intimacy as the result of my infidelities. I would argue that I stepped out because there was no intimacy/sex in my then marriage. No regrets what so ever!

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