My (F)irst 3some. Fucked in the Ass and Double Penetration.

Sat, 08/10/2013 - 21:13 -- aryaisthebest

In my freshman year in college I was dating this guy, Paul (not his real name), for quite a while. He was my first serious boyfriend and things were going very well. I was young, inexperienced in relationships and in love. A very stupid combination that can only lead to trouble. Paul really wanted a threesome with me and another girl. His justification is that he loved me so much, and he knew that he would always be with me, but he felt like he would be missing out on experiencing certain things in life. Like a threesome with 2 girls. That’s why he really wanted to have a threesome with me and another girl, so that I can be a part of that experience.

Stupid naive me thought it would make him happy, so I finally agreed. Paul immediately suggested we do it with Megan, my best friend. His reasoning was that we both knew her, so no worrying about STDs, and we would all be comfortable around each other since we were already friends. It sounded like logical reasoning, so I finally agreed, mostly because I figured Megan would never agree.

Paul lived off-campus in an apartment building with a pool and a hot tub. One night Paul, Megan and I happened to be in the hot tub when the discussion drifted toward sexual fantasies. By drifted I mean Paul asked Megan what her sexual fantasies were. One thing led to another and Paul asked Megan if she would be up for a threesome. Megan asked if I was ok with it and I reluctantly said that I was. She then surprisingly said that she was up to it as well and she and Paul quickly decided that this would be the perfect opportunity to do it (at his apartment, not the hot tub). At this point I realized the situation was quickly spiraling out of control and jumped in and said that I have a few caveats. I told them that I was ok with having the threesome, as long as they don’t have sex. They were very disappointed, but I stood my ground.

We got out of the hot tub and headed up to Paul’s apartment. His roommate was not home and Paul suggested that the three of us take a shower together to get started. We were all wearing bathing suits (Megan and I had bikinis on) and showering after the hot tub seemed a good idea. Having Megan strip naked infront of Paul sent a pang of jealousy through my heart. She didn’t seem to mind at all and he was ogling her body. He didn’t even notice when I got naked. When he stripped off his swimsuit his penis was completely erect. Paul turned on the water and we all got into the tub (it was one of those combination tub with a showerhead). Paul immediately grabbed some soap and started lathering up Megan’s body. He didn’t waste any time before he started massaging her boobs and playing with her nipples. I stood to the side, cold and away from the water. Megan poured some soap into her hands and started playing with Paul’s penis. They were clearly enjoying each other’s bodies while I was left to the side. I managed to get my hands on the soap and started soaping myself up. I was about to put the soap back when Megan switched places with Paul, so she would be closer to the water. She turned with her back to him and placed her hands on the wall tiles. I figured she was going to ask him to soap her back or something, but instead she spread her legs, and before I could say anything he slipped his penis inside her and started fucking her right then and there.

I was so shocked I didn’t even say anything. Not only had they completely ignored me the entire time, they completely disregarded my request not to have sex. Not to mention that they didn’t even bother getting a condom. Usually Paul can go for quite a while, but I guess the excitement of getting to fuck Megan was too much for him and he suddenly grunted while she moaned, and I realize he just came inside her. He pulled out and they both cleaned themselves up. They asked if I was done, and I just nodded. So they turned off the water, toweled off and headed to the bedroom. By the time I got there they were already going at it in the 69 position. Megan was trying to get him up again while he was clearly enjoying her pussy. I tried to decide how best to get in there, and since I wasn’t as interested in Megan’s pussy I grabbed Paul’s penis and tried to help Megan get him erect. Soon he was up and ready to go, but instead of pleasuring me he pushed Megan off of him and onto her back, and slipped inside her for the second time, again without a condom. I was left with nothing to do but watch them. They completely ignored me.

Afterwards I was very upset. I didn’t say anything, but after a few days I exploded at him. How could he fuck Megan like that? He was completely flabbergasted and blamed me completely. He had no idea why I was so upset: So what if they had sex? It was a threesome. Oh I felt out of place? Obviously it was my fault for not joining in. Etc...

A few days later I was back at Paul’s apartment and his friend Ryan was there as well. I still hadn’t forgiven him but I still loved him and desperately was trying to think of a way of making him understand how I felt. Ryan was very interested in the threesome and kept asking questions about it. I don’t know whether he didn’t realize that I was upset, or if he was purposefully trying to make the situation awkward for his own amusement. He kept agreeing with Paul and in general was pushing my buttons. Finally I had enough and asked Paul how he would feel if I had a threesome with him and Ryan. I was unhappy and jealous because he fucked my best friend, maybe the best way to make him feel the same is to fuck HIS best friend. I always thought Paul was a bit of a homophobe, so I never expected he would be ok with being sexual next to another naked man. To my surprise they both agreed immediately.

They started taking their clothes off and I wasn’t really sure what to do. They had called my bluff, but I was angry enough to go along with it to see how far they would be willing to take it. I figured Paul would be jealous of Ryan seeing me naked, so I started taking my clothes off as well. Soon we were all naked. I covered my breasts with one hand and my pussy with the other. Neither Paul nor Ryan was erect, but Ryan was definitely checking out my naked body. They both stood there, trying to see how far I would take it, so I dropped my hands and let them look at me. Paul didn’t seem to mind, and Ryan had the biggest grin on his face. I knew I had to do something to make Paul jealous, because being naked in front of Ryan was clearly not enough. Ryan’s penis started growing, so before I could back out I got down on my knees, grabbed it in my hands and started giving him a blow job.

My head was spinning. I couldn’t believe that I was blowing my boyfriends best friend in front of him. I looked over to see what Paul was doing. I was hoping to catch his face to see if he was jealous. To my surprise he walked behind me, grabbed my hips, and pulled my ass up. Then I suddenly felt his hand slide between my legs and he started playing with my pussy. Once I was went enough he pulled his hand away and I felt the head of his penis press against my pussy lips. I wanted to tell him to stop, I was supposed to be fucking Ryan to make him jealous, instead it seemed like he was fulfilling some fantasy of fucking me while I blow some guy. Despite myself I was already very wet down there, and he easily pushed himself in. I suddenly found myself stuck between them. Ryan started fucking my face while Paul was fucking my pussy from behind. I had nowhere to go and just tried to keep up as best as I could. They fucked me like that for at least a few minutes before Ryan grunted and started cumming. I had nowhere to go and he blow load after load into my mouth. There was nothing I could do, and as Ryan continued thrusting his penis in and out of my mouth, I had no option but to swallow. Paul, realizing that Ryan was cumming, picked up the pace and a few moments later I felt him cumming deep inside my pussy. Then they both slowed down and pulled out.

They both lay down exhausted on the bed. I wanted to lie down and rest too, but there was still some cum in my mouth and I could feel the cum from my pussy leaking out. I crawled to the edge of the bed, managed to stand up and hobbled to the bathroom. I didn’t even check if his roommate was home as I crossed the hallway. I cleaned myself up as best as I could and rinsed my mouth with mouthwash. I was annoyed that Paul seemed completely fine with what happened. Plus I didn’t get a chance to fuck Ryan, which was the whole idea. So, still naked, I went back to Paul’s room. Him and Ryan were just starting to put their clothes on, so I told them that we weren’t done yet and walked over to Ryan. I told him to lie on his back, then grabbed the lube that Paul kept in his drawer and poured some on my hands. I started massaging Ryan’s penis and as soon as he was erect, I got on top of him and lowered myself down.

I purposefully didn’t use a condom because Paul didn’t use one when he fucked Megan. Ryan’s penis felt great inside of me. He was just as big as Paul and the lube made it feel nice and warm. I was sitting on top of him, cowgirl position while he played with my nipples. I was just getting into a rhythm when I felt Paul’s hands on my back, pushing me down onto Ryan. I wasn’t sure what he was trying to do, but decided to go with it and pressed my breasts against Ryan’s chest. I remember he smelled really good. I kept rocking back and forth, letting his penis slide in and out of my pussy, when I suddenly felt Paul’s hands on my buttocks. He spread my butt cheeks and was pouring lube down my crack. Then with his finger, he started massaging it into my butt hole. I wasn’t sure what to do. Paul knew that I liked some anal stimulation while having sex. In fact that is the easiest way to make me orgasm. He regularly fingered me back there when we had sex, and occasionally we even did anal. I figured he was just trying to help me have an orgasm. Soon he had one finger in, and once he was able to easily slide it in and out of my ass he pushed in another. I was just starting to feel my orgasm building when, with a wet plopping sound, Paul pulled his fingers out of my ass.

Then Paul climbed onto the bed and got on top of me. I was wedged between him and Ryan, who was still fucking my pussy. I wasn’t sure what was going on, but then I felt the tip of Paul’s penis against my ass. I said “wait!”, just as he pushed the tip inside. He stopped, the tip of his penis pushing against my ass pucker. I held my breath, not sure what to do. I guess he took that as an approval because he went back to slowly pushing it in. Ryan stopped thrusting and with his penis buried deep inside my pussy, waited until Paul was all the way in. I breathed quickly, everything down there felt “full”. I didn’t think I would be able to take them both, but Paul kept pushing as far as he could, then pulling out, applying more lube, and pushing in again.

When he was all the way in I was finally able to breath semi normally again. Then they both started slowly thrusting, in and out, in rhythm. I can’t even describe what I was feeling. I thought I was going to faint from the over stimulation. When Ryan went into my pussy Paul pulled out of my ass, and when Ryan pulled out of my pussy Paul pushed back into my ass. They started going faster and faster and I could feel my orgasm building. I couldn’t speak or say anything. Just breathing was difficult as my orgasm built and built. It’s hard to explain, but I never felt anything like it before. It was like my orgasm was building and building and like it would just grow forever. I couldn’t even think, I could just feel them thrusting in and out of both holes and my whole body felt like it was going to explode. At some point I realised that I was moaning, just this continuous moan that went up and down with their thrusts. I could feel my ass and pussy contracting like crazy from the orgasm. Just when I thought that I couldn’t handle it anymore, I felt Paul shooting his load deep inside my ass, immediately followed by Ryan blowing his load deep inside my pussy. It was the greatest orgasm I ever had and I screamed so loud I lost my voice for a week.

They both stayed inside for a few minutes, long enough for me to feel their seed spilling out of my pussy and ass. Then Paul pulled out and got off of me. Ryan rolled me off of him and got up. I rolled back onto my stomach and just lay there, my whole body shaking. I knew that there was no way I could get up. I lay there for a long time, their cum slowly leaking from me while they both got dressed. I was happy to see that Paul’s penis was clean, as the situation was embarrassing enough as it is. Then they both left the room and went to the living room. I don’t know how long I lay there on Paul’s bed. Finally I got up and went to the bathroom. His roommate was home by then and all three of them were sitting on the couch. I didn’t even care as I walked naked to the bathroom. I took a shower, went back to Paul’s room and got dressed, then went home. They asked if I was ok and I just nodded.

Afterwards, Paul was completely fine with what happened. He was not jealous at all. I was still upset, except now Paul was able to hold the threesome with Ryan over me and said I had no reason to be upset about anything. We ended up breaking up soon after that and Paul immediately started fucking Megan regularly. He also told everyone about what happened, and to my surprise that made me VERY popular with the boys.

aryaisthebest's picture
Arya

Toward the end of my Sophomore year in college, I dated this guy for a bit. We were really into each other and it felt like things were getting serious quickly. Over the summer he invited me to go on vacation with his family. I want to share my experience here.