[Group] Regretting the Swap!

At the end of my first semester in Nursing school, I hooked up with two fellow nursing students who were room mates, Connie and Christy. Connie and I had been flirting back and forth the entire semester. The week before finals, and in the middle of an Artic snow storm, Connie and I hooked up and decided to become Fuck Buddies. We spent a great four days together during the snow storm. We both realized that we were very compatible when it comes to sex. So, I invited her to my Fraternity formal the following February. It was out of town at an All Inclusive Resort. Connie said she had the perfect Little Black Dress for the formal.

I picked Connie up the Friday after class and we drove up to the resort. I had reserved our room for two nights. Figured we would have some out of town fun together. On the way up to the resort, the topic of our sexual past came up in order to pass the time. Connie went first and it was your typical high school sexual history. Boyfriends, experimenting with girls, the usual high school stuff. Connie had a couple threesomes with her roommate, Christy; one of which was with me. But, nothing wild and crazy. So, once she was done, I was my turn. I started from the beginning. Figured I had nothing to loose since we were not dating. Went into how I lost my virginity to the older daughter of a family my parents knew. Then, went thru the junior high and high school girlfriends. When I told her about fucking the mom of a high school girlfriend, she really started to get hot. While I told her about a one night stand I had last year, Connie was openly masturbating. In fact, she had her feet up on the dash, leggins and panties down around her knees and was rubbing her pussy and tits. It was very hard to concentrate while driving with Connie rubbing one out right next to me.

Once Connie had made herself cum, she decided that it was only fair that I got to cum as well. So, she leaned over the center console, pulled my cock out the leg of my shorts and proceeded to suck my cock like she had done so many times already. Connie knew exactly what I liked and just how to set me off with running her tongue along the underside of my cock. After about three or four minutes of this, I shot my load into her waiting mouth. The great part about Connie’s blowjobs were that they did not end once I had cum. No sir. She continued to bob her mouth and hand real slow so as to milk every last drop of cum out. Then, after she swallowed my load, she would go back and clean me completely off. She sure was going to make a wonderful wife to someone one day.

Once we got up to the resort and checked into our suite, we went and had dinner. There were several of my fraternity brothers and their dates up at the resort also. We ended up having dinner with Alan and his long time girlfriend, Becky. The girls hit it off right away. Becky was beautiful. Could have been Valerie Bertinelli’s 20 year old body double. Anyway, after dinner, we all went back to our suite to drink and talk. The girls matched Alan and I drink for drink. Within an hour, we were all feeling rather good and horney as hell. The topic of Connie and I not being in a relationship came up. Becky was rather interested in the Fuck Buddies part. Becky and Alan had been dating since their Freshman year in high school. Neither one of them had fucked anyone else. Becky wanted to hear all about us, and Connie gave her the long version. And, you could tell it was having quite the effect on Becky and Alan. Apparently, they had been talking about having a partner swap. But, they didn’t know how to go about it. Becky flat out asked Connie if she would be ok fucking Alan in front of me and asked her if she would be ok with her fucking me in front of her? Connie said, “Of course.”

With a few more drinks, I think all of Becky’s inhibitions were gone. Connie and I had been making out on one of the couches. Connie whispered into my ear, “Do you want to fuck Becky?” I replied, “Fuck yes I do.” Connie went down to her knees and unzipped my pants, pulled out my cock and started to give me a blow job with Alan and Becky sitting across from us. I could see Becky and Alan talking. After a few minutes, Becky got up and walked over to us and kneeled down besides Connie. Connie stopped sucking my cock and asked, “Do you want a turn?” All Becky could do was nod her head yes. So, Connie got up and walked over to Alan as Becky took my cock into her mouth. She was very hesitant at first. But, after a few tries, she got into a good rhythm using both her mouth and hand. Meanwhile, Connie had crawled into Alan lap and taken off her shirt. Alan was feasting on her breasts.

Connie asked if we all wanted to take this party to the bedroom. We had a king size bed and there would be plenty of room for all four of us. Both us guys got undressed while the girls helped each other out of their clothes. Once Becky was completely devoid of clothes, Connie and Becky came over to the bed. Becky laid down on the bed and I immediately spread her legs and started to eat her pussy. Becky’s pussy was not completely bare. She had trimmed her pubic hair down to a “Landing Strip” right above her pussy. I began to lick and suck all along both her inner and outer lips of her pussy. I glanced over at Alan and Connie and they were in a 69 position with Connie on top. I was about to warn Alan that Connie squirts sometimes when she cums; but I was too late. She drenched his face. As much as I could see, it appeared he loved it.

After making Becky cum several times with my tongue and fingers, I got in between her legs and started to inch my cock up her pussy. Alan’s cock was only about 5 inches fully erect. So, unless Becky was into large dildos, she was going to be very tight. And, I was not wrong. Becky was extremely tight. It took a full five minutes for her to get used to my size enough to get only three quarters of my cock inside her. Once she was ready, I started to pull out and push in with nice slow strokes. Meanwhile, Connie was going to town riding Alan’s cock. She had been on top of him only two minutes before he grunted and blew his load inside her pussy. I could tell she hadn’t even gotten cum yet. Alan apologized several times before Connie climbed off and tried to suck him back to life.

Once Becky got used to my size, I started to pick up speed fucking Becky. I had almost every inch inside her pussy before her first orgasm hit. When Becky came, she no longer held back. She started talking like a porn star. “Holy shit. Fuck that pussy. Make that pussy yours. Make me your whore. I want to feel you cum inside me. I want to feel every inch of your cock slide inside me.” It was so bad that I heard Alan tell Connie he had never heard her talk like that before. Connie replied to him, “She has never been fucked by a cock that big either I bet.” I could tell that hurt him a little. Connie grabbed his face and kissed him as she got back on his cock and started to fuck him again. With Becky’s tight pussy and verbal onslaught, coupled with Connie fucking Alan not three feet away, my balls could not take anymore. I gave one last push and let go with a load that made Becky scream and cum at the same time. Just then, Connie’s first orgasm hit and it was one of her all over orgasms with her body going stiff and shaking.

I don’t know if the alcohol was wearing off, but Becky wanted Alan to take her back to their room. So, after they got dressed and left, Connie and I hopped into the shower to clean off and then head to bed for round two and sleep. The next day, we took full advantage of the indoor pool and hot tub. In fact, since we were the only ones in the hot tub, Connie clawed into my lap, pulled my cock free of my bathing suit, pulled the crotch of her suit to one side and fucked me nice and slow in the hot tub. Connie got to cum twice before we had to stop due to other people coming into the pool area. Connie felt bad that I didn’t get to cum, so she pulled me into the sauna, dropped her suit bottoms and bent over the bench with her ass in the air. I was still rock hard from the hot tub. After getting plenty of her pussy juice on my cock, I fucked her hard and fast. Maybe it was because I was so turned on or maybe because we could get caught at any moment, but I came in record time. I came so hard that it triggered Connie’s orgasm as well.

A few hours later, we were dressed for the formal. Connie was turning heads from most of my Frat brothers. While their dates wore high school prom dresses, Connie had a sleek, little black dress and it barely covered her ass. And the cherry on top, she was going commando. No panties or bra. Needless to say, I spent most of the formal hard as a rock. Connie’s outfit definitely got plenty of attention; including from Alan and Becky. Becky asked if she could steal Connie for a few minutes. The girls headed out of the ball room to talk. “My God David. She is stunning in that dress.” I just smiled and said, “Yes she is. And, as an added benefit, she is not wearing any panties or bra.” Holy shit I thought he was going to cum right then and there. The girls came back and Connie grabbed my arm and lead me to the bar. “Becky wants to swap partners again. However, this time, she wants separate rooms.” I almost choked on my drink. “Why does she want separate rooms?” Connie smiled and said, “Because she said that Alan felt too awkward with her right beside him.” I thought about it a moment and said, “I’m game if you are.” Connie just smiled, kissed me and giggled like a school girl.

So, Becky and I went back to their room and Connie and Alan went to our room. As we got into the room, I asked Becky if she had a good time last night. Becky got very red and shy. “Yes I did. But, I really don’t want to have sex.” I was very confused. “I thought this was your idea?” Becky started to cry. “Alan said it wasn’t fair that I got to fuck like that when he came so quickly. He said he wanted another chance with Connie; but, he wanted to be alone.” Becky really started to cry then. “Becky, you need to tell Alan how you are feeling. Or, it will be the the wedge that comes in between you both.” Becky just curled up on their bed and didn’t want to talk any more.

So, I left and went back to the bar at the party. Connie found me about an hour later. “Why the hell are you down here?” I told her what happened. “I decided that I wasn’t going to interrupt you and Alan.” Connie blew a big raspberry at me. “Mr. Minuteman came before he even got his dick inside me. He spent most of the time giving me oral. We tried fucking again. I sucked his cock to get it all wet before he fucked me, and he blew his second load in my mouth. I was done after that.” I made the mistake of taking a drink as she told her story. I laughed so hard, I got choked up on my Bourbon. Connie grabbed my hand and took me back to our room. As soon as we got into the room, she stepped out of her dress and sashayed her ass towards the bedroom. Connie looked over her shoulder at me and said, “I want you to fuck me like you bought me!” By the time we were done fucking, we were both sore, happy and fucked completely out.

The next morning at breakfast, we both saw Alan; but, Becky was no where to be seen. He looked like hell; like he hadn’t slept at all. One of my Frat brothers came over to me and said, “Do you hear about Alan and Becky?” Connie and I both played dumb. “Becky left him last night. She packed up her shit and left. Rumor is that he cheated on her. Someone overheard her yell that they were finished. He is going back to the frat house with Roger.” So, she didn’t follow my advice. She laid in her room until Alan came back and lowered the boom. Connie looked directly at me and said, “See, that is why I don’t want in a relationship right now.” I just shook my head. I kind of agreed with her at the moment. However, I wondered if I would still feel that way if we continue to be Fuck Buddies.

Source: reddit.com/r/gonewildstories/comments/josca8/group_regretting_the_swap