Winning A Bet And Gaining A FWB

by Kolos

What’s your gender? Man
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Columbus
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Accountant
What’s your current relationship status? In a serious relationship (open)
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)? Well over 100
How many hookup stories have you here posted before? 0

Winning A Bet And Gaining A FWB

How long ago did this hookup happen? 1 year

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 1 to 3 years

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? We’ll call my partner Andromeda. Andromeda is in her early 30’s, with long brown hair and brown eyes. She’s a little on the chubby side, but not by much. We’d worked with each other at a campground for over a year, and had become pretty good friends. We regularly shared our sexual experiences with each other and were rather close, even though we had never been intimate before. Andromeda is bisexual, and had been with several men and women in the last year, and I am heterosexual in a relationship with a cuckquean, and have been with several different women in that same time. Our Friday night shifts usually devolved into discussions of our sex lives, with our cowokerer Madeline and my girlfriend Kim sometimes thrown into the discussion.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Andromeda had a camper on one of the campsites that weekend, and after our shift, she, our coworker Madeline, my girlfriend Kim, and I had gathered inside her RV and were sharing a few beers. We’d all managed to get Saturday and Sunday off, and were planning to party in the camper all weekend now that our Friday shift was over. We’d been drinking a few beers, not enough to get drunk, but we were all tipsy, and discussing our sex lives. Andromeda was talking about how she’d gotten a new large dildo, and loved how full it made her feel. Madeline asked her how big the biggest real man she’d ever had was, and she said it was a little bigger than six inches. Kim laughed at her and told her that I was over 9 inches. Andromeda thought she was lying and called her out on it.
Kim told her she wasn’t lying, and that if Andromeda had a ruler she’d prove it. She bet Andromeda that if I were under 9″ that she’d spend the rest of the night eating Andromeda out, but if it were over 9″ that I got to use her however I wanted to the rest of the night. Andromeda said that it was a deal and that she’d enjoy having a tiny Asian fucktoy for the night.
Kim told her to get the ruler, and that she would get me hard. She sat down on my lap and shoved her tongue into my mouth. Her little ass rubbing on me got me going right away. Kim kissed me one last time and got off of me and I stood up in front of Andromeda.

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? Andromeda unbuckled my belt and slid my pants and boxers down to my knees, exposing me to her. The look of shock on her face told me she’d never seen one as big as mine. She rubbed her right hand up and down it a few times, then put a ruler up to it. 9 1/8 inches. Just enough to win the bet. Andromeda is a woman of her word and asked what I wanted to start with.
I told her to take off her shirt, that I’ve wanted to feel her tits around my cock since the day I met her. I sat back onto one of the beds in the camper, and she pulled off her shirt and removed her bra. Her big creamy tits sagged just a bit, and she had rather small nipples for the size of her tits. She got on her knees in front of me and wrapped her breasts around my cock. This was something I’ve always loved doing with well-endowed women, but unfortunately, my girlfriend just did not have the ability to do it. Her smooth skin on my cock quickly brought me to the end of my rope, and I came all over her breasts and her face.
When I came down from the clouds, I noticed that Kim and Madeline had stripped naked and were sitting on the other bed masturbating, and had apparently found Andromeda’s sex toys. I was used to my girlfriend’s antics, but was rather surprised that Madeline was willing to expose herself in front of me. I had better things to do though and pulled Andromeda into a kiss where I could taste my cum on her lips.
We both stripped naked, and I took a second to look at her soft ass and the hair covered pussy my dick would be calling home for the night. Andromeda got on her hands and knees on the bed, her large breasts hanging down. I crawled in after her, and positioned myself at her pussy. I didn’t waste any time, and shoved my entire length inside her in one push. We fucked like this for quite a while, and she was a very active partner. She ground against my thrusts better than anyone I’d ever been with. Her pussy was amazing, and I knew if I didn’t stop it would be over.
I pulled out of her, and told her that I wanted her to ride me. I laid down on my back, and she mounted me and leaned over, her breasts hanging in my face. While she began rocking back and forth, I searched for her clit with one hand, and used the other to play with her tits. It wasn’t long after I’d found her nub that she came. During her orgasm, she stopped moving and threw her head back and moaned. I was close, so I rolled her over onto her back, and re-entered her in missionary position. It couldn’t have been more than I minute later that I came inside her pussy.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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 made out for a few minutes, but fell asleep soon after we’d finished. The next morning, everyone got showered and we went on with our original planned activities. We discussed what had happened the night before that afternoon, and agreed that it would be alright to try it again. Over the last year we’ve gotten a campsite at least once every two months, and sometimes more when it’s warm. Andromeda and I are still friends, but nothing more than that. We have sex, but there is no emotional attachment aside from that of close friends.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s)

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? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

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

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

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

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

To whom did you talk about the hookup? How did they react? Our coworkers, and they were generally shocked we went though with it.

How would you best summarize people’s reactions about this hookup? Mixed (Some positive, some negative)

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? Sleeping with Andromeda fulfilled one of my biggest fantasies.

What was the WORST thing about this hookup? The only downside about this hookup was that Kim and Madeline did not participate in it.

All things considered, how POSITIVE was this experience? Very 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? Casual sex has always been a part of my life. I lost my virginity to casual sex, and over 80 percent off all sex I’ve had has been casual.

What do you think about the Casual Sex Project? I think this is a great thing, and will do wonders in gathering information about casual sex that is not geared towards college students.

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