My girlfriend and one of her good friends Carol have been pushing for a four way for some time. You can read my previous posts about our threesome experiences with each other. They have had 2 play sessions together before Carol started dating Jason. Carol is 26 about 5’5″ with shoulder length dyed blonde hair with brown roots, she has a thin frame with small A breasts and no ass and looks much younger than her age. Emily, my girlfriend is 5’1″ with long wavy hair brown hair, she is curvy with almost DD breasts. I am 5’8″ with a beer belly that formed after college, but not awfully big. My dick is right around average at just under 6″ but I like to say 6″ to feel good. Jason is very well built at about 6′ and played college baseball. They came over on Friday night for dinner and to drink, play catan, or other board games; typical late 20’s couples date. I was AWARE that Carol and Emily wanted it to happen but I thought the issue was shelved.
After dinner and some board games we were all outside around our backyard firepit drinking. I was waiting for them to call an uber and go home as I was tired and drunk. Emily and Carol are next to each other giggling about lord knows what and they disappear into the house without notice. Fine. I am chit chatting with Jason about football and the sad raiders. He is a nice enough guy. After another beer a piece he asks where the girls are at. My first thought was that they were mixing some cocktails as beer was not their drink of choice that evening. But shortly after coming inside, it was very clear what they were up too. Jason was still outside so I went upstairs to access the situation. The moans from both ladies was growing as I climbed the stairs. The door was open and before I reached the top step, I could see Carol in the full throws of an orgasm. She was sitting on top of Emily’s face towards the wall and bucking on our headboard. I let her finish and entered the room. I wasn’t exactly sure how to feel, I knew they have been wanting to fool around again and to involve myself and Jason.
Carol turned towards me, kinda surprised but just smiled and slid off my girlfriend. Emily sits up against the headboard, face covered in Carol’s juices, smiles and jokes “What took you so long?” I wasn’t sure how to respond but said that I didn’t think this was going to happen this weekend. They both smiled and said it wasn’t planned but “Carol couldn’t keep her hands off these puppies,” Emily said while grabbing her large breasts. I gave her the laugh she wanted then proceeded to ask them both what they wanted to do, especially because Jason was outside and I had no idea how much he knew. Long story short, we agreed to let it happen assuming Jason was on board.
Carol doesn’t put on her clothes but grabs her jacket and goes to the backdoor to motion Jason to come inside. I am not sure what she told him but he came upstairs very confused at his nearly naked girlfriend and as a group we discussed the situation. He clearly was not super pleased that I have had sex with his girlfriend, and I didn’t exactly want him to have sex with mine but after a group talk, that seemed to be the only thing that was going to move the night forward and I felt I was the only thing holding it back. Emily and I had discussed this at length and I was more OK with a stranger being the new partner if one was to happen rather than a friend, but she didn’t mind so it was easier to give in. After talking, taking shots, a bit of grooming etc we all moved back the to bedroom. The first 5 minutes were possibly the most awkward in my life but Carol and Emily broke the tension by making out.
The girls were clearly OK enjoying themselves and were getting very into it. Jason and I stood near the bed watching the girls kiss and assessing each others package. He was about an inch longer and had much more girth, I was a bit more jealous now but to late to turn back. The girls moved their way towards us and each kneeled down off the bed and started to give blowjobs, Emily with me and Carol with Jason. I was surprised to hear Jason ask to switch, and gave me a look to test my reaction but I didn’t protest. The girls switch but I suggested Carol tag team Jason and make him more comfortable. I wasn’t the biggest fan of Carol’s blowjobs but a double blowjob is pretty great and Jason was enjoying it and it seemed to remove some of the tension. Carol stood up and layed her back on the bed and motioned for Jason to enter her. Emily guided his cock into Carol and was massaging his balls. Jason gave a few pumps but came very quickly, and I couldn’t blame the guy. We assured him it was OK and Carol did a great job of cleaning him off.
Emily said that it was time for Carol to return the favor and took the same position Carol had with her back on the bed and legs hanging off. Carol kneeled below her and began to lap Emily’s soaked vagina. I got on the bed and kissed Emily and played with her wonderful large breasts. She suggested I finish Carol off. Carol bent over to provide me access to her and still get between Emily. I start by licking her freshly waxed vagina and then put on a condom and begin to fuck Carol. I could see Jason was slightly uncomfortable but did not object. I was giving it to Carol for a few minutes and Emily was giving me the look that she was ready for some cock. I told Jason he should grab a condom from the bowl and show Emily a good time. He was very eager and entered Emily as soon as he had the condom on, she assumed the same position next to Carol bent over the bed. It was weird seeing my girlfriend fucking another man but fair is fair. Emily was enjoying herself so I was happy.
We both finished around the same time and thankfully it wasn’t to weird. Jason gave Emily a hug and then kissed Carol. He thanked me and we were both unsure what to do next. Carol knew exactly where the toys were and removed the strapon harness and our dildos. These clearly freaked Jason out and we explained pegging and Jason was definitely not onboard and I didn’t really want to with another guy there. Emily was all to happy to take it from Carol who was putting on the harness. Carol got on the bed and motioned for Emily to assume missionary. Carol began to fuck Emily and play with her breasts, largely ignoring us. The girls were pleasing each other for a few minutes. Emily motioned for Jason to come near her and began sucking his cock again. I watched this for a few minutes and in the meanwhile Emily got on all fours and let Jason get in front of her to continue sucking his dick. I took Jason’s place for a few minutes and Emily was telling Carol how fun it was. She took the strapon off and got on all fours. Jason got behind Carol and started to fuck her without a condom and I got in front but Carol just doesn’t have the same blowjob skills as Emily and it was hard to enjoy it. I told Jason we should switch and he seemed fine with it.
While I was fucking Carol, Emily put on the strap on and said it was her turn. I thought I was giving it to Carol pretty good but holy shit, Emily started to fuck her so damn hard I thought she was going to rupture something. Carol was unable to continue sucking Jason because she was moaning and cumming like girls in a porno. Both girls were moaning very loudly before Carol slid off the strapon and collapsed on the bed. Each of cuddled up with our respective ladies and chatted about the past hour. The girls tried very hard to convince one or both of us to try something anal but we resisted. Jason definitely wanted to cum again and wanted some with Emily. He started to kiss and rub her body and Carol put a condom on him with his back on the bed. Emily crawled on top of his cock which was larger than mine but took it without problem. She was bucking and cumming within only a few minutes. Carol started to give me a blowjob and I let her continue for a few minutes but suggested she crawl on Jason. Emily got off and wasn’t done and without asking crawled on top of Jason’s face. He was unprepared and later we learned had never had a girl sit on his face but he was giving it to Emily good while Carol was riding his cock. I used the time to play with both girls and their nipples but I wanted get some too.
Jason and I switched positions and Emily got on my dick and started to kiss me. Jason grabbed Carol and flipped her into doggy style right next to me. Jason came inside Carol who then tried to climb on my face with a pussy full of cum. I resisted but Emily crawled off and began to lap up the cum dripping from Carol without a word. Carol said she wanted me to add to it and told me it was fine to fuck her without a condom. Emily said it was fine and I finished in her after a few minutes. I was surprised to see Jason have no problem enjoying my cum. We relaxed for a bit and took turns as couples taking showers. Surprisingly it wasn’t as awkward as I thought the next morning.
Source: reddit.com/r/gonewildstories/comments/5mugci/first_fourwaygroup
This reads like a combinatorics exam.
Man this sounds so awkward. Like you didn’t really want it to happen and he didn’t really want it to happen, but you both let it happen because of the girls. This seems like one of those examples of how a man’s “masculinity” keeps him from truly enjoying himself and letting go sexually.