Bachelor Party

by Brian

What’s your gender? Man
How old are you? 29
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, New York
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Broker
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)? 3
How many hookup stories have you here posted before? 0

Bachelor Party

How long ago did this hookup happen? 2 years

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

How would you best classify this hookup? Group sex

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? Stacy was a girl I’d worked with for two years and had admittedly lusted after. She’s about 5’6″, long haired brunette with the most amazing body I’ve ever seen in real life. Which is a big reason I lusted after her for so long (and unfortunately still do). That and her huge tits.

Maddy is Stacy’s friend and someone I’d met a few times before this night. About the same height as Stacy, dark hair to her shoulders, crazy bright green eyes. She’s a bit curvier but still looks good naked. Her tits were a good handful but her pussy was totally waxed which drove me crazy since my fiancée, now wife, didn’t even trim.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had a joint bachelorette/bachelor party in Miami in May of 2014. Our entire group spent the first day and night together but the second night we split up for dinner and shenanigans as my fiancée called it. We met our first day of college and had been together ever since so our group was comprised of all mutual friends. It was tame but fun. On the second night my boys took me to a dance club down there. At first it was normal; drinking, dancing, being stupid but then Stacy, from my job in NYC was standing there in the middle of the group. It took me a minute to wrap my head around it because I couldn’t figure out what the hell she was doing there but my best man, who happens to be my older brother, nudged me and asked her to join us. That’s when she pulled in Maddy. They played it up as this big coincidence but even drunk I knew there was no way she was in that club, on that night, in that outfit by chance. I was right.

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 was kind of a dick to both of the girls because some of the guys were friends with my fiancée and I didn’t want them to know I knew these girls. By the time we left it was about 2am and nobody seemed any wiser that I knew them so I felt like I was in the clear. Got to my room, said good night to the guys and checked in with my fiancée who was already in her room at another hotel. She was wasted according to her friend and truth be told, I was looking to come over and have sex but that was off the table as she was throwing up.

Knock on my door, it’s my brother who is well aware of my fascination with Stacy. He walks in with the two girls and despite my protests, which I swear were valid at the time, convinces me to chill out and get in the hot tub. Against my better judgement, I did it, with my boxers on. My brother did the same, the girls got in in just panties since they hadn’t worn bras and it was in that moment, when I saw Stacy’s tits for the first time that I knew there was no way I was passing up an offer from her. My fiancée is pretty small and frankly, after only having sex with her and knowing she was it for the rest of my life, I wanted to get my hands and mouth on those girls.

My brother gave me a few quiet pep talks about how I’ve been wanting this, how this would never happen again, how nobody would ever find out, how he’d vouch that he was with me etc and after a short time he left and there we were alone. My heart was beating out of my chest when Maddy asked if I’d be ok if they kissed each other a little. I said nothing because I literally couldn’t speak. They were inches from me, kissing and sucking each other’s nipples. This girl, whom I have jerked off to, whom I have fantasized about while having sex with my fiancée, is getting her huge tits sucked by another woman inches from my face. So when she moved closer I didn’t think about it, I just latched onto her other breast and let it all happen. Under the water Maddy took my hand and slid it into her underwear and then asked me to finger her which I did. Stacy pulled her up, laid Maddy on the side of the tub, spread her wide and told me to finger fuck her while she sucked on her clit. She came in less than a minute and before I could even process what was happening they’d stood me up, had my boxers off and were both sliding their mouths along each side of my dick. I held on for a minute but then Stacy looked up and told me to cum in her mouth and that she’d been wanting to suck my dick for years. I came pretty much then and there. I couldn’t help it.

They rinsed off and got on the bed, wet hair and all and immediately started to 69. I sat there, guilt creeping in along with another erection. Maddy went to her bag, tossed a condom at me and told me to fuck them. I really did feel guilty and I didn’t react right away so she got on her knees, put the condom on and told me to lie back. I was about to protest but Stacy straddled me and it was so much like the millions of fantasies I’d had of her that it was surreal. She fucked me by herself for a few minutes and then told Maddy to sit on my face which she did. I came when Stacy moaned that she was loved my cock and that she was coming and then promptly fell asleep, condom still on.

Woke about two hours later to them both sucking me again, giggling about the taste of my cum and the rubber and the guilt disappeared when Maddy got on all fours and begged me, literally begged me to fuck her. I did even though from behind she reminded me of my fiancée and we didn’t have another rubber. I almost lost my wood because of it but Stacy slid underneath and spread her legs so that Maddy could go down on her. Seeing her face down where I was fucking was too much but when she lifted her head and licked my shaft and balls I couldn’t help myself. I came, pulling out just in time to stick my dick in Stacy’s mouth.

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? The guilt was swift and crushing. The sun was coming up and I panicked that my fiancée would wake up and come over even though it was barely 7am. The girls took quick showers and then left, promising to never say a word and to act like they’d been in Miami for work if my fiancée ever asked about it. I drained the hot tub, got rid of the condoms, wrappers and the bottle of Fireball they’d left behind and then I showered. I’m not going to lie, I cried in the shower. Sobbed. It was like porn star sex but at the time it felt gross instead of hot.

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

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

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

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 didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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 brother. He had flown them down and had kept them as a secret between us. He’s married and miserable so in some way this was his own escape I guess. I was pretty pissed and also pretty grateful. Honestly the emotions and the mixture of guilt, satisfaction, pride etc was too much for me to handle and I took it out on him. In a way, what he set up and I partook in affected our relationship and not for the better.

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? Very

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

Do you regret this hookup? Very much

Why do you regret this hookup? I’m conflicted in regards to regret because it was amazing and at the time, perfect. I fulfilled a number of fantasies that night but in doing so, I cheated on someone I love. It has forced me to evaluate myself in a way I didn’t think I had to and I’ve come to the sad conclusion that I’m not the man I prided myself on being. I don’t ever want to cheat but I know now that I’m capable of it. I feel like shit regularly but still masturbate to the memory. It’s been a total mind fuck.

What was the BEST thing about this hookup? Fulfilling my fantasy of the girl I’ve wanted for years. Having a threesome, cumming three times in one night (that had never happened before).

What was the WORST thing about this hookup? The crushing guilt that will not go away no matter how much time has passed. My fiancée states regularly how happy she is that we’ve only ever been with each other and how safe that makes her feel and every time she says it my stomach churns.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? If this had been done without me being in a monogamous relationship it would have been unbelievable. So no, it hasn’t changed my view on casual sex in general but it has changed my view of myself and casual sex.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup? Nobody ever knew anything happened and to this day I debate telling my wife. I still work with Stacy everyday and I’ve seen Maddy a handful of times. They’ve both never brought it up but at the Christmas party last year I almost had a panic attack when I saw Stacy and my wife talking. Talk about feeling like an even bigger shit. Two months ago I became a father and when I hold my little girl all I can think about is someone doing this to her one day. A week ago Stacy and I worked late along with another guy who left for a coffee run. The mood changed and I know she was hoping to start something up. I want to fuck her again so badly, she truly is the most stunning woman I know but I’m pretty sure adding more guilt on would give me a heart attack.

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? Sow your oats before you tie yourself down because the guilt is not worth it.

What do you think about the Casual Sex Project? I’m going to read through it more. A friend told me about it a few weeks ago and I thought this would be the only safe place for me to get this out. Hoping that helps the anxiety and guilt that I’m pretty sure are slowly killing me.

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