Weirdest Cuck Bachelor Party
My College roommate freshman year was a nice guy, but he always seemed a bit strange and quiet. We were only roommates freshman year. I thought he didn't like me because one morning he had left for class and his girlfriend had spent the night. She got out from his bed bare naked and said "Gerry is gonna be gone for awhile, can I come to your bed?" I was a hyper horny college freshman, I felt bad but I did more thinking with my dick than my brain back then and didn't hesitate. We fucked a good handful of times after he would leave for his 8 AM. We got new roommates the next year, he never confronted me about it so I figured he didn't know. We kept in distant touch after college occasionally texting. He was not the kind of guy to make many friends.
Fast forward 9 years, I had seen him maybe 3 times in that span, but he texted me asking if I wanted to go to his bachelor party. I felt bad for him that I made the short list, but also wasn't so surprised because he was not good at meeting new people. He wanted to go golfing, then to some bars near his house and offered his apartment as a place to crash after. The bachelor party was just the groom, myself, and 1 other guy I had never met. It was actually a pretty fun day, and we did a lot of drinking starting in the morning on the course. While we were at the bars, he told me that he knew I had banged his college girlfriend and my heart sank. I was wondering if he brought me along a some kind of setup or revenge, but he told me that he actually put her up to it, and he was into having his girl fuck other guys. I asked if he does that kind of thing with his fiancé and the other guy at the bachelor party had apparently already fucked his fiancé a few times. Then he said that if we wanted, he wanted to watch us tag team his wife to be.
I am married now, one of the few times I saw this guy was at my wedding. So I told him that I couldn't join, but I'd watch with him. He understood but also a few more times before we headed back tried to tempt me. One of the things he said was "She's also almost 2 months pregnant, so you can cum in her." My memory of some of the convo is hazy at this point, but that one stood out to me. I held strong that I wouldn't be able to join though.
We got back to his apartment and I met his Fiancé for the first time and she was shockingly better looking than I imagined. She was a short Hispanic, she was a tad thick but far from fat and the thickness showed in the right spots. The super stunning part of this was that she was only 21, I and the groom were 29 when this was happening (last summer) and I don't know how old the other groomsman was.
We settled into their family room and chatted for a bit and then she asked "So do you guys want to have some fun?" I told her my situation and that I would also be watching, and maybe I was just drunk but she seemed so cheery and charming and said "Aww even for a bachelor party?" I still held my ground though. Gerry and I sat on separate individual chairs, while Chris and Alexandra got onto the couch and she started to blow him. I was hard as a rock, I had never watched other people have sex in person and for a moment understood maybe why Gerry did this.
She got naked and had a really nice rack. She had carmel brown skin with darker brown nipples Gerry had taken his dick out started to stroke in his chair and having seen both guys dicks now I knew mine was bigger than both and I remember part of the thought going through my head when I pulled mine out was showing off. I was starting to waver in my commitment when you are masturbating to a girl in the same room, who has offered herself to you, it is not the best position to remain faithful.
Gerry suggested I let Alexandra help me, I started to break, but still tried to hold a barrier and said "Ok but just a hand." She came over and bent over in front of me, Chris followed to hit it in standing doggy and her warm hand gripped my cock and started to stroke it. I sat back in the chair and guilt quickly gave way to pleasure. Now all that was running through my mind was I had a willing mouth, maybe a foot above my exposed, hard cock and I wanted more. I put my hand on head and guided it down. She got the message and didn't hesitate. Her warm wet mouth felt amazing, and her gentle moans were muffled by my rock hard cock. Feeling the moment I said "I'm gonna cum down your fiancé's throat." I tried to cum, and it felt amazing, but I was a bit too drunk. After a few minutes I knew I wasn't going to be able to cum with a blowjob and the best feeling in the world is cumming in a vagina raw.
I told Chris it was my turn, I told her to sit on the couch and threw her legs up over my shoulders. Chris stood next her off the end of the couch and took her mouth. Her moans, her wet pussy, her perfect tits bouncing, seeing a cock in her mouth, and a few minutes of hammering away, I thrust deep and dumped a warm load into her flowing like the Mississippi.
