Out of Character

by Dandm

What’s your gender? Woman
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? New York
Highest education received: Post-graduate degree (currently pursuing)
What’s your occupation? Financial analyst
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 0

Out of Character

How long ago did this hookup happen? Last summer

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

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 was much older but sexy and cocky and confident

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? My fiancé and I were at one of those trendy restaurants/bars on the water that you can dock your boat at. My fiancé and I discussed previously how turned on he would be watching me flirt with and seduce an older man but it was always one of those things we fantasized about but felt safe talking about because we didn’t think either of us would go through with it. That night there were lots of guys there with their fancy boats and flashing their money etc. my fiancé and I were there with a couple different groups of friends etc. my fiancé actually struck up a convo with the guy about sports and I kept blushing the way he kept looking at me and I was kind of turned on that I could tell he was only being nice to my fiancé because he wanted an excuse to keep looking at me. I stepped out on the deck to smoke a cigarette and he followed me out there when my fiancé stepped away for the bathroom. We flirted and he bought me a drink, and complimented me and told me I look just like that actress Neve Campbell. He was sexy for a guy old enough to be my father but his confidence turned me on that he had no qualms about continuing to flirt with me right in front of my fiancé. I could see my fiancé was turned on but also nervous because all our fantasy talk could become reality. He asked us if we would want to take a ride on his boat and we agreed, my fiancé and I talked briefly while the guy was driving the boat and we both agreed that we would let something happen if the guy made a move.

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? To make a long story short, we went a distance out and he dropped the anchor and told us to make ourselves comfortable as he made small talk about the businesses he owned and the boat and then to break the ice he mentioned to my fiancé how lucky he was to be with such a beautiful girl, my fiancé was game and played right into it and told the guy that he should show me where the cabin is and he would wait upstairs. My fiancé and I both gave each other the most excited look and the guy took my hand and led me down to his cabin. He started kissing me right away and I confessed that my fiancé and I talked about his fantasy of me fucking an older man. He wasted no time and ripped off my romper and put his hand in my panties and he could feel how wet I was as he fingered me and kissed me. He stopped to ask me if I wanted to invite my fiancé down to watch and I told him no because it would be awkward, we continued to kiss some more and then he ate me out while I was standing and I orgasmed really hard and made a point to scream really loud so I could be heard above. He then laid me down on the bed and even though it was a big boat the cabin is still cramped so he immediately got on top of me, he was down to his underwear so it was a crazy tease feeling his cock rub against my bare pussy through his underwear, we made out intensely and I had no idea when his underwear came off but I suddenly felt him enter me and I let out a short moan, I asked him if he had a condom even though he was already inside of me and he said no and stupidly I didn’t make him stop because it felt so good and I was on the pill anyway. We fucked missionary for a few minutes and then we tried doggy style but it was too cramped to pull this off so we went back to missionary. He was being Rough, kissing me hard and licking my breasts and going in and out of me and I told him he has to pull out since he had nothing on, we fucked for another five minutes and I wasn’t quiet either I felt him tense up and he didn’t pull out and I felt him explode inside of me, I was a little annoyed that he finished inside of me but he apologized. He laid on top of me and inside of me while kissing me and I felt him get hard again, we fucked very slowly and kissed and he came again in me very quickly. He got off of me and got dressed, I laid there for a few minutes trying to process what had just happened. The guy then opened the door and told my fiancé to come in, my fiancé was able to watch the whole thing through a window and without any words quickly took off his pants and got on top of me and within three minutes came inside of me. It was an awkwardly quiet boat ride back to the bar, my fiancé and the guy shook hands and the guy gave me a kiss on the cheek goodbye.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

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? My fiancé and I discussed this and even though he was immensely turned on he confessed he was also mad and it wasn’t what he thought it would be, he said reality hit him when he watched another man fuck me and that’s why he felt compelled to have sex with me immediately after to claim his property. Our relationship became a lot stronger because of it and we both agreed to be completely monogamous but don’t regret testing the limits and trying out a fantasy, I am very mad at myself for not using protection and my fiancé was furious that I let the other guy finish inside of me. We both got tested after and were fine.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant, Discussed STI testing history

What were your motives for this hookup? Learning new things, experimenting, Thought it was an important experience to have, Intoxication

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

How wanted was this hookup for you at the time? I don’t know / I’m not sure

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? My fiancé afterwards. He had unexpected jealousy even though it was his fantasy but it also made our relationship stronger and made him realize his insecurities about himself and our relationship.

How would you best summarize people’s reactions about this hookup? Relatively positive

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The sex was so spontaneous and forbidden which gave it a different intensity level and the fact that it was a long time fantasy coming true without any planning.

What was the WORST thing about this hookup? Being careless about safe sex and letting him finish inside of me, even though it was physically more pleasurable the regret after was not worth it and the fear of STD’s.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have had one or two casual sex encounters before I met my fiancé but always preferred monogamy, it did help our relationship by taking away the curiosity of wanting an open relationship or living out the fantasy again, overall we got it out of our system and even though we wouldn’t repeat it it made me realize that casual sex has many benefits.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I think couples and singles need to experience beyond the societal norm and risk a little bit while Learning new ways to communicate with their partner and themselves and be introspective.

What do you think about the Casual Sex Project? I think this is fantastic, I found this completely by accident and it is a good way to get off your chest things you can’t tell anyone else in person but want to share to benefit others. It also makes you realize not to be ashamed because there are others with experiences similar to yourself and sex is an important part of everyday life.

You have a hookup story to share? Submit it here!