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My first and only (so far..) foursome
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My first and only (so far..) foursome This happened years ago when in was college… of course a bit of alcohol was involved... youth and alcohol made for an amazingly crazy combination. With alcohol having been involved some of the details are a bit hazy but they are accurate to the best of my recollection as I had put much of it down in my journal/blog that week not wanting to forget that night. It was in my 3rd year of college and I was seeing a guy for a few months. His name was Val and he was one of the first guys I had been with at the time when I started actually enjoying guys for more than just anal sex… something about him just made me want more than just being fucked, he actually made me feel like a girl. I had actually wanted to kiss him and in fact he was the first guy I had ever kissed. This was well before ever starting my transition and he only was only interested in me as a girl though, so the only time we ever met up was when I was putting my best foot (and pair of heels) forward! He was bi and this was the time when I really started to come to the realization that I was bi as well because I was finding a few guys that I found attractive, and not just wanted to use as sexual means-to-an-end. I had always been more traditional when I thought of my sexual relationships and so I never really liked being with anyone sexually unless there was a rapport established, even with the guys I would hook up with, (I never felt too comfortable with random or anonymous sex) and so I generally practiced monogamy when there is any sort of a relationship established, unless it's entered explicitly with the open understanding by both to start that it wouldn't be exclusive/monogamous. From the beginning he said he didn’t want monogamy, which I understood but I didn’t care to see anyone else. I told him I was okay with that, and I was, but my only stipulation was for him to be open and honest about who he was going to be with and I would join if they were interested. I thought it was a simple request to ask to know who else my sexual partner was planning to be with, and I even told him that I would join if they ever wanted. I had never had an experience with more than 1 sexual partner at a time but was open to the idea. He lived with three other guys, two of which were also bi/bi-curious (I say bi-curious because he had not been with a guy, but said he was open to guys and trans girls), and 1 of which was straight. His best friend, the straight roommate, was Ryan and was always very nice. He actually seemed like he might be into me as he flirted frequently, but considering he identified as straight, I didn’t think he was interested and might have been doing that as a way to make the situation more comfortable when around each other. It was all innocent enough, he was very cute and attractive – tall… taller than me and clearly hit the gym frequently - and it was fun, but it certainly never came close to anything more than harmless flirting. Val and I weren’t exclusive after all and so it shouldn’t have been an issue anyway. After about two months of “dating” him, I heard through a friend of a friend that he had been seen “hooking up” with a number of girls recently as well as a couple (guy and girl), but he never mentioned anything to me and so I tried not to give it much credence beyond hearsay and chalked it up to people just no quite knowing our agreement with our relationship. I mean, come on, all I asked was that he tell me when he is going to or after he hooks up with anyone, a very small thing to ask right? I can’t say I wanted to know more than just for the reason that if I ever met up with or ran into any of those people it would be good to know. Well one night out with him and some of his friends, it came up when we were talking to a couple with which he apparently participated in a threesome. I was surprised as I couldn’t recalled him saying anything to me. A threesome is one of those things that would have certainly stood out. It bothered me a bit, but said that he thought he had told me about it and thought maybe he did and I just didn’t hear him clearly at the time. Later that night I was talking to his friend, Ryan, and he mentions a few other instances of which I had never heard about my ex being with girls, and couples and all in the last few weeks. It seemed that he wanted to know why I didn’t join them or if I was just not interested in anything outside of Val. Well it was clear that he thought I knew because of the way he was asking me and it seems all instances were very recent and different from the one we were talking about earlier. Well, that bothered me a good bit more. Of course I was probably a bit inebriated that night, but it upset me nonetheless and I know I was bothered when I heard the rumors previously. Later that night I asked Val directly about it and he actually denied all of it up until the point he realizes that Ryan had unwittingly told me. When he finally acknowledged it to me, he said that it was none of my business who he was with because we were exclusive. I ended it the next day on the simple grounds that I felt he had no respect for me as he pretty much just wanted to fuck around and have me as a backup plan in case he didnt get lucky... I wasn’t really looking to be a backup plan and I was clear up front that I simply just wanted to know who it was. Mostly I think I just wanted to know so if I had heard anything I could be up front and honest about knowing and being okay with it. Someone telling me and me not knowing felt like it would be embarrassing. Regardless, I have much more self-respect than to be with someone who clearly lacked respect for me, but I harbored no malice towards him other than the utter confusion on why it happened. Probably the dumbest reason to stop seeing someone you could ever think up, but it was just a dumb situation. Few weeks later when I was out with some of my friends who had dragged me out because they were pushing me to find someone new to distract me from school and pull me out of my disinterest in sex of late. So they made sure to help me look my best that night. I was in a red dress, hair down, heels and was looking pretty good. We get to the second bar that night and while heading to the bar to get some drinks, I see Ryan (Val’s best friend), who used to flirt and hit on me. I was with my friends and Ryan was with some of his friends and his roommates but Val wasn’t there with them. I was pretty sure he didn’t see me, but wasn’t sure if I should go over and say hi in case it would put him in an awkward spot. After about 15 minutes hanging out with my friends, I get a tap on a shoulder asking me if they could buy me a drink. Of course when I turned around I saw it was him. He said that he wasn’t sure if he should come over because he wasn’t sure if I wanted anything to do with him after all that happened with his friend, but then said he didn’t want the chance to at least say hi. I smiled and jumped up to hug him as I had been a while since I had seen him. Thinking he wasn’t actually interested in me made it easier for me to be friends with him when had flirted with me because it seemed to keep me from being nervous about it and not overthink it. Of course I was happy to see him though especially considering he did nothing wrong and was always so nice and I had thought of him as a friend when we used to all hang out together. Some of my friends were looking to leave and head to another bar, I told them that I would catch up with him in a bit and would text/call to meet back up with them later. We talked for a while. He told me that he was sorry he even said anything back then and if he knew that saying anything meant that I was going to end it and I would not be around to see them anymore that he would have kicked himself in the face. He told me he thought I knew about it all because he couldn’t understand why my ex wouldn’t have told me considering how “open and understanding…not to mention how “awesome and sexy” I always was. He was nice and continued his flirting like he used to, and I didn’t think much of it because it was always the norm and just his way of being friendly. Over more drinks though, the flirting became more physical and he was flirting a lot more than he used to (well more aggressively at least!). His other two roommates joined our convo at some point and after a few shots, I was getting my ass grabbed, pinched, and all 3 of them were having their flirting become more physical and I was playing right into it, I had never had anything like that before. At some point my friends called me and told me that if I wanted to go back to campus with them, that I should meet them now. I was having a lot of fun but I felt bad that I abandoned my friends and told them I’d meet up with them in a few minutes. Being the good friends they were, they told me that I was being dumb and I should stay because I was doing exactly what they wanted me to do - Later I found out that they had actually run into Ryan a few days prior and he asked about me, they told him I was going to be out that night and that they would let him know when we got to the bar where he was that night - When the guys heard I said I was going to leave to head back home, they all proceeded to give me a hard time and told me they would all drive me home whenever I wanted to leave later. I let my friends know not to worry about me and that I would see them later tonight. We continued to drink (there were at least 3 shots involved) and have a good time. At one point I started to say (well more like confess) a bit more than I would have otherwise. I admitted to Ryan that I always thought he was cute and that if I had met him first I would have tried to flirt with him. I even also mentioned that I had had an erotic dream about him catching Val and I having sex and joined in. I also told him that if he wasn’t only interested in girls (not yet coming to terms identifying myself as a girl at that point) that I would have tried to date him. It was that statement that I got a bit more of a reaction than I expected. He seemed surprised by my statement and I can remember all three of them laughing and telling me that none of them had ever thought of me as anything but a girl. It does make sense now because I was always dressed as a girl when I saw them and they had not likely ever seen what I looked like other than when I was dressed as a girl. It seemed that they never said anything or tried anything out of respect for Val because he apparently told them to stay away from me. This is a significant point in my mind as it was this identifiable point when I started to actually really think of myself as a girl and not just a boy who wore girl’s clothes or a boy who was born in the wrong body, regardless of what my genetics said about me. More time passed and it got to the point where he and his friends asked if I wanted to join them for food and drinks back at their place around the corner (I did of course know where it was). Having fun and clearly quite turned on at that time from all the groping, I headed out with them in the hopes that maybe something could happen. We stopped by a place around the corner and picked up food to head back to their place. After we got back to their place I was still feeling quite good and so decided to move away from alcohol, then after food, a few non-alcoholic drinks, and some dancing (with a heavy bit of grinding) on coffee tables, Ryan starts really laying it on thick and finally at one point he turned to me and said, "I<b> love </font></b>him like a brother, but Val is a huge idiot!... if I had a chance with a girl like you, I'd never look at another person…" due to still being quite buzzed and turned on I grabbed him and start making out with him. I know that may have been him just wanting to get in my pants, but it didn’t really matter. This was the first time I had ever done anything like that with a guy because it was always the guys who were forward and made the first moves (although it was about 50/50 for me when I was with girls). I actually got really embarrassed as I could feel my face get flushed and pushed him away apologizing for doing that. I even turned away and said I was going to leave when he grabbed my hips, turned me towards him and kissed me. It was a deep kiss and very exciting. It also seemed that it was exciting the other two guys as much as it was the two of us, because they didn’t seem to want to be left out as they started touching me and kissing the back of my neck (…getting all around “handsy”). Although they were bi, they had never really showed any obvious interest (before tonight) in me like Ryan did so I didn’t really think they were interested. All of it was quite the surprise, but I was getting so caught up in it that I clearly didn’t care. I was still very turned on and of course started also touching them as I made out with Ryan. He and I continued to make out for a while and it was becoming quite obvious that I was certainly making all three of the guys excited… I never did kiss the other two guys though, but they weren’t my type. They pulled off my dress at one point and I was only in my bra, thong and heels. I didn’t have my boobs yet since I didn’t start on hormones till years later but my body was clearly feminine and they all seemed very appreciative of my thin figure, soft skin and long legs. It was all so crazy, I was standing semi-naked in the living room of the house of a guy I had dated (who wasn’t even there), making out with his best friend and becoming sexually physical with his other two roommates, and up to that point I had never felt as sexy as I did right then. I eventually got all three of them to take their shirts and pants off too and it was at that point when I realized that I might actually be doing more than just touching and kissing with them tonight. After some more dancing and a little more making out, Ryan grabbed one of my hands and placed it on his boxers. It was then very clear he was very ready for more than just kissing. I broke away from kissing him and leaned down to slide his boxers down as if opening a present to see exactly what he was working with. What I found was a very pleasing gift beneath. He was 8 inches long and one of the biggest ones I had ever seen firsthand. It was definitely more than a handful (more than two actually) and thicker than anything I had touched previously. I smiled at him as I bent over to give it a kiss. After I did, his other two roommates, upon seeing this (and my ass as I bent over I suspect), dropped their boxers as well and walked over to surround me. I proceeded to then kneel down as I wanted to please Ryan so much right then, when he grabbed me by my hips, lifted me up and threw me over his shoulder. He was clearly quite strong. It was one of the sexiest moments I can remember and I was screaming and giggling as I was lifted in the air and bent over with my ass facing out, feeling somewhat embarrassed with being so exposed and vulnerable. That feeling of embarrassment didn’t last long and quickly melted from surprise to elation and finally, to extreme excitement as he carried me through the house to his room in the back. I looked up to see his other two roommates only a few steps behind seeming just as eager for what was coming next as I was. When we got to his room, he tossed me from his shoulder onto his bed and went over to his computer to turn on some music. I crawled off the bed and kneeled with my back to the bed as all three of them approached me with their excitements pointing directly at me. Ryan was in the middle and so I took him into my mouth and placed each of my hands on the other two standing before me. I moved between all three of them pleasing each of them orally but focusing most of my attention to Ryan. He was the only one I really wanted, the other two were just icing on the cake. After quite a few minutes of going down on each of them, I looked up at Ryan and asked if he wanted more than this. He didn’t bother to answer and just reached is hand down to help me up. He climbed on the bed and laid on his back. I took this as a queue to climb on top of him and proceeded to make out with him, it looked like he hesitated for a moment (probably because of having just gone down on him and both of his other roommates) but seemed to just shake it off and proceed to kiss me deeply. I felt his hands grab my ass and start guiding it back till I felt him pressing against my entrance. I was really very nervous and told him that I wasn’t sure it was going to fit and he told me that I didn’t have to do anything I didn’t want to. Well clearly I wanted to, so I proceeded to press back and slowly start to move my hips up and down. I felt the pressure but it wasn’t going much inside of me. I raised myself off and tried to take a deep breath to try again, when I felt something behind me. One of the other guys was leaned over and began rimming me. I had only been rimmed a few times up to that point but knew it was one of the best ways to help relax me and give me a chance of fitting something inside me. I proceeded to make out to Ryan and I could feel my body become overwhelmed with warm pleasure and I knew I was relaxed enough to try again. So I leaned back and guided him inside of me. This time was almost completely different as about an inch and a half of him slid in me very quickly. He felt huge, but I was so turned on that the slight pain only felt more pleasurable. After about a minute of slow rocking I was able to get about half of him in me, but I was certainly not used to it yet. Finally I knew I wanted to get him all in me, so I arched my body and leaned back on him till I felt my ass resting on his thighs. I think if I wasn’t so turned on, I would have gone cross-eyed with pain at that point but it felt good the pleasure still outweighed the pain. I sat for a moment with him deep inside me and the other two guys approached us on the bed from either side. They were kneeling and so I proceeded to suck each of them off as I felt Ryan deep inside me. After about a minute I was relaxed enough that I started to slowly lift up and down on Ryan’s cock. It felt incredible and he was licking and kissing my body as I rode him while sucking on the other two guys. It wasn’t long before Ryan started to get in a good rhythm and proceeded to slowly fuck me more aggressively. A few minutes more of riding him till he told me to hop off of him and bend over. He knelt behind me and slowly entered me from behind. The other two guys repositioned themselves and laid on their backs on either side of me so I could continue to please them. Ryan fucked me harder and more passionately than any other guy had ever done up to that point. It was almost on a different level from anything I had experienced previously. I was certainly moaning with each thrust as he moved in and out of me from behind. A few times he would let go of my hips and slapped my ass lightly with each hand which only excited me even more and occasionally talked dirty to me asking me if I liked it and telling me how much better fucking me was than any other girl. I was in heaven and had more to play with than I knew what to do. Ryan was ready and groaned as he came. I could feel him pulse inside of me as he exploded. He collapsed, backed out of me and laid back on the bed. I felt empty at that moment and knew that I didn’t want to stop then. My arms were getting tired of holding my body up and so I laid on my back on the bed. One of the other two guys crawled up on the bed and positioned my body so that my legs were up in the air and he was between me. My head was nearly off the bed, so the other guy hopped up and placed himself at my lips so he could move in and out of my mouth while standing giving him good access and control. The other guy fucked me hard, wasn’t as big as Ryan, neither of them were, but they were both a decent size probably 7” and not as thick. By this time Ryan had gotten up and it looked like he headed for the bathroom. We continued to play for a few minutes when the other guy guys came. The guy who was fucking me came on my chest while the guy who was fucking my mouth came in my mouth. I was brutally exhausted, but more sexually pleased than I had ever thought possible. I had came twice, the first time when I was riding Ryan and the second time right was while the other guy fucked me. They each told me that they were tried and were going to get some water and head to their rooms, but asked if I wanted a ride home then. I asked if I could stay and they told me I could sleep anywhere I wanted. I wanted to sleep in Ryan’s room, but he wasn’t there and wasn’t sure if he would be okay with that. I finally realized he was in the shower as I heard the water running once it was quiet enough so I hopped out of bed. I knocked on the door and he told me to come in. I told him that I was thinking I might spend the night and he laughed and just said, “of course you are, you’re not getting away from me so easy. You want to sleep on the couch or with me?” I gave him the obvious answer and asked if I could get a shower when he was done. He responded, “Well I am about to get out, but why not just hop in here with me now, you can grab a towel from under the sink.” I was a bit taken aback as I had not showered with another guy before. I had showered with a number of girlfriends over the years, but never with a guy. I was crazy nervous as it meant I would be naked with him and probably wash off most of my makeup, but I figured he had seen and done so much already he knew what he was getting himself into and if he wasn’t as attracted to me when I wasn’t looking my girl-iest then it wasn’t really something that would work out anyway. I decided to just do it. It was so much fun. He was sweet and scrubbed my back and neck and even washed my hair for me. We made out a little bit, but it was quite obvious that for the night we were both quite tuckered out and so after we got out of the shower. I put my bra and panties back on and then climbed into his bed and passed out (I out them back on because one, I didn’t have anything else, and two, they just helped me feel more feminine). I woke up pretty early the following morning and sat up really quick as I panicked a little waking up in a place that clearly wasn’t my room. The warm feeling in my ass quickly snapped me back and reminded me of what had happened that night. For a few moments I felt incredibly ashamed, I had never done anything like that before and I essentially slept with the best friend of an ex. My movement must have woken him up because he asked me if everything was okay. I told him what was on my mind. I pretty much always did because I was always so comfortable with him and he was always so up front and honest with me. He laughed and told me that I had nothing to worry about because I was in college and that’s the time to do the crazy things like that which oddly made sense. It was not long till he rolled over on his back and I noticed through the thin sheets that he woke up looking ready to have some more fun if I wanted it, I also noticed that he slept naked. I leaned over to rub him and ask if there was anything I could do to help him out with it. He smiled, stretched is arms and said that he would appreciate any offer I was willing to make. Seeing as he was already on his back and ready to go, I lifted the sheets off of him and climbed on top, ready to repeat last night. When I placed him at my entrance this time, I felt the heat from his very hard cock and it make my ass tingle as I was a bit sore from the activities of the night before. I wasn’t sure if I was going to be able to fit him in again without the same help I had previously but I decided to try. I remember that Val kept some lube in his bathroom upstairs so I told him that I needed to run and I would be back in a second. I headed up the stairs and saw that his other two roommates doors were open and passed out, I had just hoped that Val wasn’t there. It seems he had not come home that night because his door was open and room was empty. I darted to his bathroom and grabbed the lube and headed back down to Ryan’s room. He laughed as I walked in after seeing the lube and asked me what I was going to need that for. I put a dab on my finder and placed it at the entrance to my ass, it felt cool and very nice, I began getting much more excited. I put a bit more on the head of his very erect cock and smoothed it to cover him. I set it next to him on the bed and climbed back on him. He grabbed the bottle and put a little on his finger. He then proceeded to gently rub it around the rim of my ass pressing in me gently. It felt really nice, not as good as being rimmed the night before, but certainly helped relax me and get me ready. I felt I was ready and told him as I leaned back, prepared to have him enter me. This time it was only a few seconds before half of him was inside me and only a few more seconds till he was all the way inside me. I told him that I wanted to be in control and make him cum, he needed only to sit back and enjoy it. He seemed okay with it because he placed is hands behind his head and smiled at me. I rode him for about 10 minutes. All of my senses were so heightened and sensitive because of the night before. I could feel every bit of him as he moved in and out of me. I worked my ass as I had practiced so much before and I ended up cumming twice before he did. I collapsed and laid in bed with him for a few minutes when I realized that I should probably get up and head out. My phone vibrated and I saw I had a message from my friend I was out with last night asking if I was okay and if I needed a ride back to campus. Ryan offered to drive me home, but my roommate said she was going to heading to the area anyway and would pick me up if I needed. I took her up on her offer and proceeded to get rest because she was only a few minutes from campus. It felt like a bit of a walk of shame through the house, but to be honest I had no problems rationalizing those feelings away quickly because of how incredible of an experience it was. I had almost forgotten where I was until I walked out to hop in my friend’s car when I saw Val pulling into the driveway. He seemed very surprised and confused by my presence there based on the look on his face, and as embarrassing as it seemed, I couldn’t help but do anything but smile and give him a small wave goodbye. I actually saw Ryan for the remainder of that year, but he moved away because he got a job after he graduated that year. We stayed in touch a little over the years but he is married now. While it’s not something I'm proud of, it is a sexual experience that I can’t help but look back on with a smirk. I had not ever before, nor have I since then (as of January 2015 at least) been with more than 1 person at a time sexually. I am open to kink and getting wild if my partner wants, but am very satisfied with simple 1 on 1 passion.   |
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1 post 2/5/2015 10:28 pm |
Wow! That was incredibly erotic, but at the same time, so sweet and vulnerable. Honestly didn't expect something like that on this particular site. You didn't happen to be a lit major in college, did you?
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1/4/2015 9:27 am |
Wow... that turned me on!! Great story!
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Great read. Very informative experience of your college years. Thanks for sharing.
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WOWO what an exp ...pleasure reading it
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