His First After 18 Years of Monogamy…



What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your current relationship status? Dating casually
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Polyamorous
How many sexual partners have you had in your life (including oral sex)? 6
How many hookup stories have you here posted before? 4

His First After 18 Years of Monogamy…

How long ago did this hookup happen? 1 day

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For less than a month

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? He introduced himself on a forum where people come to talk about polyamory. I could tell that a) he was handsome, and b) he was new to this world. So I was instantly interested and offered to exchange experiences with him, told him I had recently been in the same position he’s in now. He agreed to chat privately and we hit it off immediately. All the while, I was aiming to get more out of it. When we met each other face to face about a month ago, again to ‘exchange experiences’, he told me how pretty I was and how he hadn’t had such a good time in ages.

He’s ex-military, which you can definitely tell by the way he’s built, his haircut, his scars, his tattoos.. I thought that was really exciting about him as well.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The second time we met, he took me out to dinner. After that, we went back to my place for drinks. We were having a good time, but I wasn’t sure if I wanted to have sex. Then, the decision was made for us (literally…) because the weather got real bad and his wife told him it wasn’t safe for him to drive home. She had been encouring him to pursue a sexual relationship with me, and she told him to stay with me or to get a hotel to spend the night, which kind of pressured me into deciding right there and then if I would let him stay with me… I decided I would. We started making out passionately on my couch and it got real steamy real quick, until he stopped so he could first let his wife know he would drive back the next morning.

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? After he let his wife know he wouldn’t be back until the next morning, I got on his lap and we started kissing again. He was touching me all over my body, putting his hands under my dress. It didn’t take long before he got me out of my clothes and started kissing and sucking on my nipples. I took his clothes off as well and slowly dry-humped him a little to get him real excited.

He then asked me if I was on the pill, “before I lose control and put it inside of you right now”. I told him I’d get a condom so he could lose control. He asked me if I wanted to finish there on the couch, or go upstairs to my bed. I told him I was OK with the couch and we could repeat it in the bed. This was obviously the best answer I could have given… He didn’t wait until I got the condom but he put me in the corner of the couch and got on the floor in front of me, on his knees. He then started kissing my breasts, my stomach, and worked his way down. He was licking and kissing me just the way it should be done, and I’ve had a few of these moments with other men but I’m usually disappointed or unable to enjoy it, not with this guy though… He kept getting me extremely close to orgasm again and again, driving me crazy and making it impossible for me to get distracted. He seemed to enjoy it a lot himself, and he didn’t stop once, I didn’t once feel like I should hurry up, so I could enjoy it to the fullest. When I finally did cum, it was the most intense orgasm a man had given me in years, and he just kept licking me until it started to hurt a little and I had to push him away.. God, it was good…

Then we went upstairs, where he just started licking me again, until he got so excited he finally grabbed that condom and put it on, pinned my legs up and started to fuck me. He took control, put me in different positions, which I absolutely like in a man. I got on top of him for a minute but it didn’t go very smoothly so he got back on top of me. Then after a while he turned me around, on my knees, and started doing me doggystyle. It went so deep and fast… At some point he stopped and made me do the work, obviously enjoying it and moaning. Then he continued and I could tell he was close to orgasm… I told him to look in the mirror, which he told me he wouldn’t do because it would make him cum immediately and he wanted to make it last longer.. so he did… When he finally did cum, he pulled me up so he could hold me close to him, which made me experience it with him – GREAT.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? We brushed our teeth and got back in bed together, where we went to sleep. The next morning I woke up as he was getting ready to leave. He kissed me a few times and then let me get back to sleep.
Later that day, we sent each other some messages, we were both still on an ‘after-sex-high’ and we told each other we wanted to do it again soon. I’m excited, he’s a stable person and I’m sure that he won’t change his mind about it, so this could be the friends-with-benefits situation I’ve been looking for… I have other friends-with-benefits but these men are unreliable – sometimes I don’t see them for a month…

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, It was easy / convenient

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

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

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? I can’t choose, one of these:
– New dick
– Great orgasm
– Great sex

What was the WORST thing about this hookup? N/A

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Not really but I’ve recently had some mixed experiences with casual sex and this once again proved that it can be AMAZING

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!