Close but No Cherry

by DJ

Gender: Male
Age: 31
Race/ethnicity: White
Current location: Connecticut
Highest education received: Some college (not currently in college)
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best?: Bisexual, recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? Too many to count

Close but No Cherry

How long ago did this hookup happen? Three months 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…)? Short fling

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? “K” was a girl I had met online. We had a noticeable connection right away and a great rapport. After talking on the phone for a while she found out that I was married but still wanted to talk to me, which was surprising because she was a very “good girl” and a virgin. She was a beautiful black girl with curves in all the right places and a great smile.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had started to shift conversations in very sexual directions. She had texted me a few incredibly erotic fantasies she wanted to do with me and had made it clear that she definitely wanted me to take her virginity, though she was still nervous and unsure. I didn’t want her to feel pressured so I said whatever happens happens and we made plans to see each other one night when I had the house to myself. She came over and we sat and talked for a while. After not too long, it began.

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? I kissed her and we started making out immediately. I love that release of tension when you need to kiss someone and be with them physically and you just can’t wait any longer. The release when you give into those urges is amazing. We kissed and made out for a while with clothes on but then we started to disrobe each other as our passion began to get the better of us. She was a great kisser despite her seeming lack of experience. I started to suck on her nipples and bite them gently and she seemed to love this. I then removed all of her clothes and my shirt and then began to make my way down to her pussy. I began fingering her pussy and rubbing her clit which was incredibly wet. She was dripping all over my couch but I didn’t care. I kissed every inch of her down from her lips to her thighs. I teased her thighs and she got nervous and self-conscious. She hesitated and said, “What if I smell or taste bad?” And I said, “I can already tell that you don’t.” I then began to lick up and down her clit and massage her pussy lips with my tongue. She was freshly waxed and very smooth which I found surprising for a virgin but damn was it sexy. After I brought her to orgasm, she said she wanted to repay the favor and began to undress me with a seductive stare the entire time. She was amazing. We kissed some more; we couldn’t seem to get enough of that. Then she began to suck my cock and it felt fantastic. Again, she was surprisingly good. I was so turned on that I couldn’t help it and I told her I was about to cum. We had talked about her fetish for facials so I came all over her face. We then moved to the bed after a brief intermission. We spent the next couple of hours rolling around in bed naked, cuddling, talking, and making out. Eventually I got incredibly hard and felt a burning need to be inside her so I had her straddle me and she rubbed up and down my cock without letting it go inside her. It was such a tease. I tried putting it in but she wouldn’t let me. I then decided to take control and threw her onto her back beside me. I got on top of her and kissed her furiously while my cico teased her pussy. I continued this way until I began to slide it in. She was unbelievably tight and I knew it was going to hurt so we both ended up hesitating. I could tell she was conflicted and though I know she wanted it, I didn’t want her to look back on our night together with regret. So we ended up not having intercourse. I pulled off and started to lick her again. She came and then gave me a hand job until I exploded again. The night ended after that and she drove home.

Did you have an orgasm? Did your partner(s)? Yes and yes.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None. I had just been tested and she hadn’t had sex so we were confident in our status.

What were your REASONS for having this hookup? We were horny and both had feelings for each other.

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? Afterwards we stopped talking for a while. A few weeks later I messaged her out of the blue and we both said how much we missed each other. She told me she regretted not having sex with me that night and wanted another chance. We got together one more time but it wasn’t the same. It was rushed and wasn’t what she wanted so we didn’t have intercourse that time either. She’s since moved across the country so the dream of taking her virginity is going to have to stay a dream. But damn if it wasn’t fun.

To whom did you talk about the hookup? How did they react? Nobody at all.

Was this a consensual and/or wanted experience for you? For your partner? Yes.

Do you regret this hookup? If so, why? No.

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? Best was how skilled she was and how willing she was.

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

All things considered, how NEGATIVE was this experience? A little negative

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