Guilt Sex?

by Ryan

Gender: Male
Age: 28
Race/ethnicity: White
Current location: New York
Highest education received: Some college (not currently in college)
Occupation: Government
Relationship status: In a relationship
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Polyamorous
How many sexual partners have you had in your life (including oral sex)? 15-20?
How many hookup stories have you here posted before? None

Guilt sex?

How long ago did this hookup happen? 4-5yrs 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…)? One-nighter

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? She was a short and extremely curvy brunette. Huge soft tits (with star tattoos on them, visible from shirt cleavage), big ass. And she had the softest lips…
We originally started talking on OKCupid. I thought she was really cute and we seemed to be hitting it off, so we decided to meet up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had planned on going to a bar that my friend DJ’ed at, so I invited her out. I met her at a mall about a half hour away and she left her car. We went to a Friendly’s for dinner because we were both feeling ice cream. Then we went to the bar. She proceeded to rack up quite a tab for the drinks she wanted. I had a few myself, but I was in-check. 
Her? She was flirting with other guys in the bar, including the DJ and 6 other friends of mine, all of which pulled me aside and told me to leave her ass at the bar or take her home because she was making out with some guy outside. Sure enough, I walk out the door and there she is, sucking face with some random tool who looked like a heroin user. I told her she was more than welcome to stay and have him drive her home, but I was leaving and she needed to get her purse out of my car. I had already closed my tab, and she said I could drive her home, but she needed to use the bathroom. 10 minutes later, I walk in and she’s making out with the same guy. I tap her on the shoulder and tell her to find her bag on the curb and I walk out. She comes racing out and gets in my passenger seat, apologizing profusely. So I go to the gas station down the street and grab myself more cigarettes and get her a water and some snacks to keep her occupied (and sober her up before she gets to her car). 
So now we’re on our way. I’m driving down a long road with woods on both sides when she says she needs me to stop because she’s gonna piss herself. So I stop and she gets out to pee in the woods. She gets back in the car, but is now kneeling on the passenger seat. She’s apologizing about how she acted and wanted to make it up to me because I was such a nice guy. Then without warning, her hand is on the crotch of my pants and she’s kissing my neck. I tell her she doesn’t owe me anything, but I don’t stop her when she goes for my zipper. She pulls out my cock and is face-down on it. So, I reach back and slip my hands in her yoga-pants and she is drenched… the wettest, warmest pussy I’ve ever felt. After about 2 or 3 minutes, she comes up and says she wants to fuck my brains out. Now, we’re not fitting in my car, so we go to my firehouse. She’s fingering herself and sucking her fingers the entire ride there.

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? So we get there, and I walk her into the bathroom, because she’s still drunk. As she’s peeing, she asks me to whip out my cock so she can keep sucking it. I oblige. Then we go to the social room with the couches, where anyone whose fucked in that place goes to.
She lays back on a couch and I pull her pants off. I pull her tits through the cleavage in her shirt and suck on them briefly while fingering her. I move to licking/fingering her pussy and she is going nuts, dripping all over the couch. She wants to ride me… NOW, so she gets up and I sit on the couch and recline back, my ass at the edge and my feet on the floor. I tell her I’m clean and don’t have a condom, so I leave it up to her. She says it’s ok, just pull out (stupid me). So she puts her feet on the edge, and squats down on my cock. She rides me like mad, we’re kissing and I’m rubbing her tits. She’s yammering on about how great my cock feels and how we’re perfect together (overly romantic stuff). So I’m about to cum and I tell her, she doesn’t stop. So I reach down and grab ahold of my cock and squeeze it. I can feel it pulsing, and she stops. I tell her to get off, that I’m holding it back and she says don’t worry about it, she’s on birth control (story-change?). I still ask her to get off and she takes her hand from rubbing her clit and puts it on mine, and slides herself all the way down. I can’t hold on so I let it all go in her. It felt so amazing. She keeps riding me for another minute, until I’m drained out. 
I get up to wipe my cock/balls/everything off because she was just dripping all over me (her juices, not mine). She takes her original spot and gives me a look… Beckons me to come over and finger her like I did before. So I lock lips with her, and start fingering her, aiming for the g-spot. I lick 2 fingers from my other hand, and I insert them into her ass, and pump away on her ass while hitting her g-spot. Within a minute, she is squirting all over the place, shaking like she’s having a seizure…Then she passes out!  Scared the shit out of me. I can’t shake her awake, so I give her a solid slap in the face and she comes to. She takes a good 30sec to remember where she is and what happened, then asked me to fuck her ass. I really wish I could have, but I was drained, so I gave her another 2 orgasms from fingering (without passing out) and then I took her the 30min drive back to her car.
She was an amazing fuck.

Did you have an orgasm? Did your partner(s)? I had one, she had like 5 or 6.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We both stated we were clean. She wanted me to pull out, but then later stated she was on birth control.

What were your REASONS for having this hookup? She was persistent, I was horny and thought she was cute and a great kisser.
And I have a thing for really slutty chicks.

Were alcohol or drugs involved? If so, how much? Alcohol. I have no idea how much she had, but with me having 3 drinks, the bar tab was over $120.

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 fine. I hoped I could have a repeat with her because she could suck and ride a dick very well.
I still feel it was one of my best fucks so far.

To whom did you talk about the hookup? How did they react? I eventually told my current girlfriend, who was just a friend with benefits at the time. She didn’t care, just felt I coulda done better.

Was this a consensual and/or wanted experience for you? For your partner? I felt like it was a little bit forced on me because I was in a bad mood, but I wanted it anyways. She was all for it.

Do you regret this hookup? If so, why? Nope.

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 thing was how good it was, and I twice got to have fun with her in a 3-way, with my girlfriend. 
Worst was how she called me a few days later to ask me if we used a condom because she didn’t remember and her period was late. She informed me a few days later she was not pregnant.
It hasn’t really changed my outlook on casual sex, but I plan on being a little more thorough on the “protection” aspect in the future.

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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