This story is a work of fiction and contains descriptions of explicit sexual acts. Some of the parts are real but will leave that up to the reader to decide. If this type of content offends you or you are under the age of 18 do not read it.
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Characters Main Character Patrick - Patty, Friend John, online friend not named.
This is one of the crazy things that just happens, I am a 17-year-old guy named Patrick who just happens to like to cross dress. I am on the small side, on tip toes maybe 5'5" and very much on the thin side, with one exception, my hips I seem to have a shape more like a young girl then a guy. I should add I have a cute face but being honest also more like a young girl than a guy. I been that way ever since I was born if my parents did not dress me in clothing that was boy's collars, I was always mistaken as a girl. Even when I was a teenager the other boys would give me a hard time and tell me I looked like a girl. I had an older sister, and not sure why I tried this one day, but when alone in the house and she was away at school, I went into her room and had this urge to try on some of her clothes. At first it was just some of her panties and bras, my sister was also on the thin side and she did not have much in the breast department so she did have a few padded bras. After I did that, I find myself jerking off looking at myself in the mirror. After a while I found myself trying on more of her clothes and I liked how it felt. I then decided I would let my hair grow, so after a while my hair looked like a short girl's hair style, which I have to say, looked good on me. I could almost pass as a young tomboy, sort of girl next door.
I went further and even started looking at tips for using makeup and came across this one guy on line who demonstrated how to use makeup, and even though he was a guy, he looked and acted very fem. I have to admit he had a huge following and looking at the profiles of his followers quite a few were boys like myself that just liked dressing. After a while I got pretty good at the make-up and with the right outfit I could almost pass as a teenage girl.
One day I figured I would try something different and contacted one of the guys following this makeup video and started emailing with another guy who was my age and also was into the same thing I was. After a few times, the boy sent me some pictures of him all dressed up, and I have to say, really looked cute. I sent him some of mine and we were really into emailing back and forth. After a while the boy whose name was Patty, yes, his real name was Pete, instead of emailing me, he called me using face time, since we both had apple devices both the I phone and an apple computer. I also had another good friend of mine named John, who also had an apple phone but we never face time. With the friend who also likes to dress up, we would set up a time when we were home alone. He would get all dressed up and so would I. Then we would make contact over face time. After talking back and forth a while, we always seem to slide our panties off and take hold of our cocks and stroke off, while talking about our desires to be pretty little sluts. This one time we were into it hot and heavy, I was all dressed up nice and cute and I was at the stage where I had my panties off. I was wearing a pink baby doll outfit that looked so cute on me and I had been fully made up with eye liner lipstick the whole works, I have to say, if it was not for my hard cock, I would be a hot cute girl.
This session, I was on my apple computer and we were having problems with the connection, so a few times during the session the connection went down, and we would have to start the connection again. So here I was on my bed all dressed up and had my ass to the camera and my hand on my cock stroking it. I had moved the wireless keyboard to my bed so I could hit the enter key to accept the call when he got it going again. We were in the middle of a conversation and were talking about being a little slut and having some big boy shoving his hard cock into our man pussy. The connection went down again and I just assumed that the guy I was face timing would be calling me back to finish our little session. I never bothered to look back at the screen and clicked on the accept button when I heard the sound of an incoming call. I was still looking away and was telling the guy at the other end how I wanted to be fucked and how good it would feel to have a hard-long cock in my boy pussy. All the time while doing this I was playing with my cock and showing my ass to the camera. I was really into what I was doing and never realized that guy who I was face timing with was not saying anything.
I kept it up for a while, then I heard the voice of my other friend, saying I never realized you were a cock sucker but being honest you are turning me on looking at you begging for cock dressed like you are. My head shot back to my computer screen and sure enough it was John. He said he was calling me but hit the face time option instead of the normal call button. To say the least I was very upset by the mistake I made, the last thing I wanted to get out was my desire to be a girl, and a slutty one at that. I was about to hang up when John said please stay on, not sure why I did but I left the connection up. John said he knew some of the boys had said I looked like a fem but John never felt it was that way but he said "after seeing you now if I did not know better, I would be happy to have sex with you." Then he added "not sure if that's true because you still have a cock but your ass does look good and with the lipstick on so does your mouth." I begged him not to say anything to any of our friends, he waited a few minutes and I saw a sly smile on his face and he said "I will not. But under one condition..."
I was not sure what to say, here I was still dressed up like a little slut and my cock betrayed me and was as hard as pole. John asked how long will I still be alone, and I said I still have about three hours before anyone comes home. John told me to stay dressed the way, but put some panties on. Then he said "I will be over Patty it will just take me a few minutes." I did ask what he wanted, but he just said that I would find out when he arrived.
As soon as I hung up the other guy that I was on face time with earlier called back and said what happened, I was unable to get back to you. Since I only had a few minutes before John would show up, my cross-dressing buddy said "calm down this could be good that you got caught, there are a lot of so-called straight guys who enjoy guys like us". I just told him "I will tell you the whole story after John shows up." He wanted me to leave the connection up so he could see, but I could not figure out how to do that without the pictures showing at my end so I did not. In the back of my mind the idea of being watched as another boy used me was exciting, but I did not know how John was going to act with the discovery that his best friend is a cross dresser. I figured there was no reason to add anything else on the top of this.
John did tell me to stay in my room dressed the way I was but with panties on and he just would walk in the door. I took a slight trip from my room to open the front door so he could just walk in. I went back to my bedroom and waited. I was sort of mixed up on this whole situation, one way I was afraid of what was going to happen and at the same time my cock was hard with the anticipation that he may use me like the girl I want to be. I was thinking I may not really be a girl but I suspect my mouth will be just as good if not better, since in my mind I really had the desire to suck cock. Also, I did not have a pussy but I had a willing ass that in my mind is tighter than a girls pussy and also as an added benefit he can slide his cock in raw, one thing for sure is, I did not have to worry about getting knocked up.
It seemed like a long time before I heard the sound of John coming into my house but I suspect it was just time moving slow because of my anticipation of what was going to happen. I was sitting at my computer and while I was waiting, I had up some porn and it was what I always seemed to watch, some young transvestite all dressed and this one just so happens to be on her knees in front of another young guy. The guy was in my mind, a real stud he had a nice strong build and a cock that was like a rod. He was really hung and once he pulled it all the way out of the gurls mouth had to be a good eight inches long nice and fat and the ridge around the helmet just looked fantastic. He did not leave it out long and slid his cock back in while holding the gurl's head as he shoved his cock all the way in, His balls were bouncing off the gurl's chin, it was such a turn on. I was just looking at the screen, as John walked into my room, he came over and did not say anything at first, he was also looking at what I was.
John looked at me and asked me to stand up and spin around he wanted to see me dressed the way I was, he then said he always felt I looked very feminine but then said he had no idea I could look this good dressed like a girl. Then I was facing him and just stood there and when I looked down, I could see a bulge in his tight jeans. I looked up with a smile on my face, and since we were both watching the same video with the gurl taking his friends cock, it was easy to figure out what to do. I reached down to his pants and undid his belt and opened the clasp and slid down his zipper then slid his pants off. As I was sliding down his underwear John stepped out of his clothes. I was now looking at his cock and it was not as big as the guy in the video, but still looked hot. John pulled up his t-shirt and this displayed his flat belly. I have seen this before since we sometimes have played sports at school we played `shirts and skins' teams. I have to admit to me this did not go unnoticed. There were a few boys who, let's say were on a little bit on the hairy side and I would get a peek at some pubic hair that would be showing on their lower stomach and I could only imagine how much hair they had over their cock. A few times I had been able to peek when they took a shower, but in my school the showers were somewhat private and the last thing I wanted to do was get caught, since some of the guys already had the suspicion that I may like boys.
John looked at me and said "what are you waiting for?" and with that I slid down to my knees and lined the head of his cock with my mouth. I looked up and John was looking down on me and I could see the smile on his face. I then opened my mouth and used my tongue to reach out and run a circle around John's cock head. He was cut and also had a nice helmet with nice ridges. This was the first time I ever sucked on a cock, but after watching so many porn video's I knew what to do and I really wanted to do this. I had been waiting for so long and now was my time. After I licked his cock head, I opened my mouth and took him in. At first, I just had the head in and using my tongue, I was playing with the cock head and from the reaction John was showing he was enjoying what I was doing.
I was in no rush, his cock felt so natural in my mouth I just knew this what I was made for, to service other guys cocks and to give them pleasure. John was telling me how good my mouth felt and he was trying to push in deeper but I was sort of holding him back I knew I had more than enough time to play with him since I was enjoying it as much as he was. What I did not plan on was the fact that what I was doing to his cock felt so good to him that I felt his cock swell up and then he said "sorry I am cumming." I held him in me, I knew I wanted to taste his load; I just knew that is what I wanted. Since he was not in my mouth that far his seed landed on my tongue, I tasted it and it was different, but not bad, I swirled it around my mouth then swallowed it. I felt like I was being such a slut and loved the feeling.
John's cock had gone down and I did not want to release it, but it was too sensitive so I had to, when John pulled his limp dick out of my mouth. He looked down and said "that was the best blow job I have ever gotten." I knew he had been hanging out with one of the girls in our class that let's say was on the heavy side, but all the boys knew she was more than happy to suck cock. We stopped for a few minutes and talked, John asked how did I start cross dressing and I just told him not sure, I just seemed to enjoy doing it so I did. He did add that he had to admit, I looked hot dressed like I was and when I turned my back to him he said now in that position I really looked hot. I felt as he came over and leaned his body into mine and I could feel his chest on my back and he reached around and started playing with my tits. No, I do not have any, but the fact he was touching my little nipples and I felt like I was being treated like a girl, was hot. I was sort of moaning and pushing my bubble butt against his cock. I was getting the reaction I expected and felt his cock growing and getting nice and hard. John had me sort of bent over as he played with my tits taking the nipples and squeezing them between his fingers. In truth it hurt, but I was being turned on at the same time. I was pushing my ass back trying to line up my hole with his hard cock that was sticking straight out from his body. I had watched videos of guys taking a cock up their ass and just knew I wanted to try it. I reached back and slid my panties to the side and guided the head of his cock to my hole.
I guess nature took over and John was pushing his cock in at the same time I was pushing my ass back. I knew in my mind I just wanted to take him in me. Once lined up, he pushed some and it hurt like crazy, I wanted it in me but it hurt so much I had to stop him. I figured maybe I have to get his cock wet. So, I pulled back and went down and took his rock-hard cock deep into my mouth and tried to get it as wet as I could. Then I pulled out and we tried again but I was still too tight. I wanted it so much in me but it just hurt so much I could not do it. I saw many of videos where the guy would eat the boy's hole but when I suggested that to John, he said no way. I was so turned on and so was John, so since I knew he needed relief I went back down again and took him in my mouth and started sucking his cock. Yes, I knew I wanted him to fuck me and make me a real girl but that would have to wait. This time I took his cock in deeper and let him fuck my mouth, he was taking long strokes and it felt good feeling his shaft slide in and out.
I could feel he was enjoying it, so while he was having fun I reached down and rubbed my cock through my panties and we were both enjoying the action. Do not get me wrong being honest, I was also enjoying just servicing his need, but feeling my hand on my cock was an added benefit. I could tell he was getting close because of the increase in his pumping and also his cock seemed to swell some. I was tasting the start of some of his cum and that was a turn on, so when he finally erupted, I had done the same and my panties were wet from my load and my mouth was full of the seed that John had fed me. I did not get fucked like I wanted to but all in all it was fun.
Before we left, John said we will keep this our little secret, but also asked when we could do this again, not sure if it was a slip or not but he called me Patty.
One thing for sure before next time I will find some oil for my boy pussy and also I decided I would look around for something to slide in my hole so the next time we are together, John will be able to get in me and I would be able to let John fuck me like any slut should.
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