A Day I Crossdressed For My Best Friend

I remember the day I crossdressed for my best friend and gave him his first blow-job and ****** his best friend in his boy ***** in which the excitement that two good friends who found love with each other’s company. I was about 15 or 16 old and at the time was pretty much into crossdressing and being a sissy boy with the fun in mind, you know a little wanking to ****, but mostly it was in private and even my family knew. It was summer time and no school so I when over to my friend Jamie’s house to see if he wanted to play or something, at the time I didn’t know what was entailed for me and my best friend Jamie. When I arrived at his house I could hear his mother saying something to him, but it was hard to hear through the front door, I when a head and rang the doorbell and herd footsteps coming to the door. When the door opened it was Jamie’s mother and she asked me what I wanted, I ask her if Jamie could play, but she look at me and said “sure, right after he cleans up his room” in a stern voice. So Jamie’s mother ask me if I would like to come in and wait for Jamie to finish cleaning his room, I answered back by saying “sure, maybe I could go and help Jamie clean up his room”, his mother had the look of dismay and said it was ok to go help Jamie clean his room. I when to Jamie’s’ room and found it totally in disarray and everything was out of his closet, I did not notice that was a mix of clothing on the floor and other stuff. I said hi to Jamie when I came through his door, but he had a look of shock when he saw me, and with a surprising voice he said to me “What are you doing here and who let you in my house?”, well I answered him back by saying his mother said it would be a good idea for me to help you clean your room up. He just looked at me and started back sorting the clothes on the floor and throwing others things into a pile in the corner of his room, I asked him what the clothes in the corner were there and why he was throwing them. He just look at me and said “I am sorting them because they are my sister’s stuff and she throw most of them in my closet yesterday and now my mom is pissed off that they were just thrown in my closet and not put in boxes or hung up”. I told Jamie that I would help and not worry about it, so we went through all the stuff and finally had all of his sister’s clothes and other stuff in one big pile, and we are talking about everything from panties to shoes and dress to separates, even something that would be underwear, but we had it in one big pile. A few minutes later I heard his mother coming , she poke her head in through the door and told Jamie to box it all up and to sort it too. Jamie just looks at her and had that fronds look on his face and I just stood there wondering what she meant by that. Jamie told me to follow him to the garage to get some boxes, so we returned back to his room and set out to sort his sister’s junk on the floor again, as I started to sort I was feeling some of the stuff and wow what a rush feeling I was getting. A lot of her clothing was really nice and soft to the touch and when I found a pair of light pink panties that were made of see thru nylon, my little heart was pounding with so much excitement as I held them. I did not know if Jamie saw me or not with the look of excitement as I help sorted the clothes. We ended up with about four boxes of clothing and shoes, I ask Jamie what was going to happen to the boxes of stuff, he just look at me and said “I don’t know, but I think my mother is going to take it somewhere. I did not want to arise any suspicions on me, but I would love to have tried on some of the clothing, so I nudge Jamie of having a little fun and surprise his mother by both of us dressing up in his sister’s clothing and see what would happen. Jamie looked at me and said, “Sure but I think you should be the one to dress up and then we can surprise my mother”, all I could do was just say yes to it and get my wish of dressing up in his sister’s clothes. I told Jamie “if we were to do this right, I would have to totally dress fully as a girl and I think we are going to need some other things from your sister’s room to make it complete”. He just looked at me and smiled and with an devilish grin, then he told me to help pick out what I was going to wear, so I picked a nice soft and silky panty and bra set and also found a slip too that match the under ware set, Jamie was looking through another box for the dress I was going to wear, with a surprising sound he said, “I found it and you are going to love it”, It was a floral design dress that came just below the knees with a really nice neck line to it, he throw the dress at me then ran off to his sister’s room, he came back a few minutes later with several shoes and boots and a pair of panty hose. He had that look on his face that made me smile too and I was very surprise everything match up so well. Jamie looked at me and said, “*****, and put on her clothes now”, I was surprised and felt a little strange wither or not I wanted to go through with this, but I was too excited and wow I was going to put on girl clothing in front of my best friend. I started to pull off my shirt and then next my pants went down, and then down went my underwear, before long I was standing naked and starting to get a hard-on from the sight of the clothing in front of me. I could see Jamie staring at me and seeing my penis getting hard, so I tried to turn so he would not see it, then he came up to me and said, “You getting hard aren’t you”, I started to turn red in the cheeks and just looked at him and nodded a yes while starting to put on the pink silky panties I selected, they were so soft and silky as I sled them up my legs and when they got to my crotch area I had a full hard-on and a little pre-*** was started to flow out. Jamie saw this reach out to me and started to touch the pre-*** stain that was forming in front of the panties, “wow, that’s cool, and it’s slippery too”, he kept rubbing in small circular motion and I could feel his fingertips pressing against my penis. I told him to stop but I really I didn’t want him to stop, the next thing is he brought his other hand around to my chest and placed it against my nipple and gently creasing it, this was really making me so excited and I was almost at a state of full arousal and shortly about ready to ********* my *** out. He told me that he was also a crossdresser like me and dress up in his mother’s & sister’s clothes all the time and the same thing happen to him, all I could do was smile at him, I told him I need to put on the rest of the clothing on for him and I would be his girlfriend to have fun with. It was hard to put the rest of the clothing on and my state of excitement was growing so passionately, but I quickly put on the pink silky bra and ask Jamie about what I am going to do for breast, I did not have any, He told me to stay put and he left his room and return shortly with a box. I ask him what was in the box, he just smiled at me and said, “I found you ******* for you and you are going to be my hot girlfriend with big breasts”. As he open the box there were two fairly large and beautiful breast forms, all full shape and even with nipples on them. I pull one out and could feel the weight and the softness of them and put one in my right side then my left, they made my chest looks so big and full like a woman, the bra was a tad bit small but forms filled it to the brim and gave me such a wonderful shape. I was getting really excited and could hardly put the slip on, but after a few calming breaths I got it on and wow that it did for me, I had the clean figure like a woman and it felt so good as I smooth it out, the whole time my friend Jamie was watching me get dress and I notice he was rubbing his penis through his pants. I put on the dress which I would say was very pretty and sat on the edge of his bed to put on the pantyhose and then the shoes, when I was finish dressing Jamie said, “wow you look like a girl too and I have another surprise for you”, ok that’s what I didn’t want to hear and what was this surprise I was getting. I sat on the bed and waited for him, a few moments later he came in with a box filled with make-up and other women things like perfumes and lotions, I ask him what I was supposed to do with these things, he just looked at me and said,” You need to be totally convincing to my mother and she will never know it’s you, so you see you need make-up and I think some pretty smell too”. All I could do was to say yes and try to be a convincing girl, I started with the make-up and was doing fine and Jamie helped here and there and he was telling what was needed to be put on next, I think he has done this before by the instructions he was giving me, I finally got to the red lipstick that Jamie pick out for me and was putting it on when I felt someone staring at me, yes it was Jamie and boy did he have a look on his face, that **** eating grin of guys who look a girls in **** magazines. He handed me some perfume and told me to douse myself good so that I smell like a sexy hot girl, so I did what he said and was brush my hair into a pretty good girlish style, I did have fairly long hair that summer and long behold on what I saw in the mirror was a lovely girl starring back at me and my friend Jamie behind me smiling at me too. I stood up and walked around his room to get a feel for the shoes, but the way the clothing was brushing up and against me I was really getting hard again and the feeling of excitement growing, I think Jamie knew I was getting excited and grabbed my hands and started to dance with me by humming a tune as he pull me closer to him. We were looking into each other’s eyes and with the gentle swaying back and forth against each other bodies he reach over to my face and kiss me fully on the lips, I didn’t know what to do or should I scream, I just return the kiss back and could feel his gentle caress on my body. He stopped and said, “wow, I didn’t think kissing another guy would be so bad, it kind of felt nice and you smell so pretty I didn’t notice you were a guy just a beautiful girl in front of me”, I just smiled back and said, “Let’s try your mother next and see if she could tell the difference”, as I smiled at him. Jamie wipe the lipstick off his lips and was think of what to say to his mother and what type of reply she would say back. I was a bit nervous and had to composes myself as a girl and the mannerism’s I would have to use to be convincing to her, so we started to the living room where Jamie’s mother was, she was sitting on the couch reading a magazine as we entered the room. Jamie cough to catch his mother’s attention, as she look up and saw us she said, “so when did she get here and where’s Billy, did he go home already, who this?”, all Jamie could said was, “this is Valorie and she got here a little while ago, she saw us in the garage getting boxes and I invited her in”. His mother asked “so where is Billy”?, and she look right at me and all I could do is smile and hope she didn’t recognize me, I was starting sweat a little and I think I turn red in the face, sure did feel warm in the room there. Jamie spoke and told his mother we were going to the TV room to play some video games or watch a movie, she really did not notice and did not show any expression about me being dressed up as a girl so we left the room when back to Jamie’s room. When Jamie was sure his mother didn’t recognize me as a girl and that she thought it was someone else altogether, he smiled at me and said, “well you did it and you are now a girl and I was wonder if you like to be my girlfriend for a while, I looked at him and said yes by taking his hand and brought him to his bed, we sat and he started to touch and fondle my chest area by giving the false **** a gentle squeeze and rub. I looked into his eyes again and soon we were kissing again and his touching went lower to my crotch area, I could feel his hand gently rub my penis that was getting hard again thru the dress I had on and as I spread my legs apart I could feel his hand go underneath my dress & slip and stated to rub and squeeze my hardening penis through the silky soft panties and could feel myself pre-******* again. The kissing got more passionate and we started to use our tongues and tasting each other while kissing, I don’t know who had the idea for me to get on my knees, but I just did and Jamie stood up and I started to rubbing front of his pants and could feel him getting hard too, I undid his pants and lower them down to the floor and was continuing to rub his penis thru his under ware, it was getting so hard and I could feel the throbbing of it. I looked up at Jamie’s face and could see him smiling at me and he said to me,” You want me don’t you and you want what I have in my under ware don’t you”, I just looked up at him and smiled and started to pull down his under ware which flop out this big hard penis in front of my face, I grabbed it with my hand and could feel the warmth of it and the pre-*** that was starting to come out. I moved forward and gently kiss his penis and use the tip of my tongue to taste it, it had a sweet and salty taste to it and yet it made me tingle a little, so I took the big plunge and stuff the big hard **** into my mouth, wow what a sensation and I could feel it throbbing in my mouth, I started to suck on it and pulling it in and out of my mouth, the sweet and salty taste was driving crazy and all I could think about was I wanted more and more. I was working his big **** and his hand was caressing the back of my head and helped pushing my face more and more onto his ****, this when on for a while and I could hear his moaning and it felt like Jamie was face ******* me with his ****. All his passionate feelings were growing and I found out real quick that his **** was about to explode and when it did, my mouth was filled up real quick and the taste of *** was incredible so salty and thick and with a little bit of sweetness to it, I just took a glop of it and swallow it, yet it seem to not end just coming out and filling my mouth. When Jamie finished he lay back onto his bed and moaned with a satisfaction sound. I was still on my knees and wiping my outside of my mouth and had a smile from ear to ear, I stood up and sat next to Jamie as he was smiling at me and I lean over him and gave him a full mouth kiss and let him taste what I had from our love making adventure. I asked him if he like it and what he thought of when he cummed in my mouth, Jamie replied that he had a wonderful girlfriend who gave him love and would love to please me also. I reach with my hand and gently rubbed his **** and he started to smile at me, then he told me, “OK, it’s your turn my sexy friend”, and with that he rolled over me and was on top on me, I could feel his **** harden again and was pressing hard against my crotch area and I could feel my **** get hard with the rubbing of his against mine. He moved down and his face was at my crotch area and I could feel his lips against my **** with the feeling of him kiss thru my dress which was driving me crazy with pleasure. The next thing was Jamie pulled up the dress and slip to expose the panties and sure enough there was pre-*** showing thru, he quickly started to kiss and lick the wet spot which was growing with every kiss and lick of his tongue, all I could do is squirm and make passionate moans. He did that for a few minutes and the without notice or warning he pulled off my panties and out sprung my hard **** which he grabbed and started to stroke it with his hand, it wasn’t long before he started to suck my harden **** using his tongue to lap it and lick the sides. All I could hear was the slurping sounds and his moaning as he work my **** up and down, I was filling with joy and pleasure form my friend giving me wonderful love and wonderful *******. A few moments later all hell broke as I cummed in Jamie’s mouth and could feel each trust of *** coming out and into his mouth, he to swallowed all of it and when I finished he came up to me and kiss me fully on the mouth and the taste of my own *** was slightly different than his. I wrapped my arms around him and pulled Jamie close to me and we were in seventh heaven with passionate love for each other, I felt his **** touching mine and it was wonderful. Jamie reaches down and grasped both our ***** and gently squeezes them together, they were both hard and mine was slippery from just ******* earlier, he gently rubbed his **** against mine and I thought I was going crazy. Jamie stood up and went to his night stand and got something out of it, when he returned he had a condom package with also a lube bottle and had the evil look again, he then said,” I going to **** you now and you are going to be my sexy **** and take it all, now roll over and put you boy ***** up for me to ****. All I could do was his wishes and so I did what I was instructed to do, I felt something touching my boy ***** as he called it, and then there was a slippery feeling like something wet being placed there. Then all of a sudden there was this poking feeling as something was being pushed into my boy *****, it was slightly painful but it went away and a warm feeling of pleasure was growing and I could feel his **** fill me inside, it was wonderful as it when in and out of me and he had a steady rhythm of ******* me. Jamie was in ecstasy as he was ******* me and I could feel him touching me on the inside and my **** was really getting hard again, then he reach around me and started to stroke my **** by squeezing it and I was going crazy with feelings of pleasure and excitement and coming close to ******* again. Jamie started to **** me faster and really squeeze my **** as he stroked it and without warning, he cummed inside me and at the same time I cummed into his hand, Jamie slowed down and laid on my back, he was breathing hard and was sweaty too but I did not care, he was my lover. He stood up and gently pulled his **** out of me and stood with his legs shaking and his hand full of ***, I got off the bed and stood next to him and wow my *** was sore form all that ******* and it felt all stretch out, he looked at me and said, “You are truly my lover now and I think you need to clean up, you can use my bathroom”. As I went into his bathroom it was kind of hard to walk and I never felt anything like it before, I went in and got some tissue to clean my boy ***** and had to squat down to really clean it and it did hurt a bit. I got myself cleaned up and put back on my panties and redid the make-up, as I reentered Jamie’s room he was straighten up his room so that no one would have notice the love making that had been going on in there. Then Jamie when into the bathroom and got himself cleaned up and put back on his clothes he was wearing earlier, when he returned he asked me if I would like to get something to eat and drink, I replied back with a typical girl answer sure. We both when to the kitchen and he got some sodas and chips out for the both of us and we when to the TV room, I sat on the couch and Jamie sat in the recliner, as we watch TV his mother came in had a strange look on her face, she just keep staring at me and could not make up her mind if she had ever saw me before, the phone rang and she shuck her head and when to the kitchen to answer the phone. I heard Jamie’s mother on the phone with someone and shortly she came back into the room, with a sharp voice she said, “I know who you are!! You are Billy!! Aren’t you!! You two try to pull a fast one on me didn’t you two!!!”, and all I could say was, “Yes your right, I am Billy! Didn’t we fool you! Jamie said if I dressed up you wouldn’t recognize me as Billy”. Jamie’s mother just shook her head and returned to the kitchen, we started to laugh and giggle, and for rest of the afternoon we watch TV and I was really feeling like a girl as I was next to my best friend Jamie. The hard part was later when I had to go home, I had to decide if I was going home as Billy or Valorie, and I really like being Valorie very much, but I know I could not return home all dressed up as a girl and I know my family would no understand if I showed up as a girl, I know my mother would have flipped her wig over me being a little girl even thou I did look really passable as one. This was a first for me and Jamie, and we were best friend in the since love each other in a special way and this went on for a few years until I moved to Kansas to live with my grandmother in my senior year of high school. Every now and then I wonder how my best friend is doing and where he finally ended up living, one day I will go back and find him and see if he would like to me dress up and be his little sexy **** again, I know I would and he could do anything his little heart desired to do and I would be his little sexy **** too. I still to this day crossdress and I have had a few encounters with other like myself who crossdress and a few others who were straight and bisexual, but I cherish my time when I an Valorie, but time to time I always have the fond memories of the good times I had with my best friend Jamie.
ValorieFrances ValorieFrances
46-50, T
7 Responses Dec 10, 2012

Wow great story glad I wear diapers might of made a mess otherwise. I remember teenage years of experimenting nice

so lovely teenage wonderful story and memory

that is a beautiful story

i could never have that much nerve...good show!

What a wonderful story - thank you for sharing it with us.

what a fabulous story. very erotic indeed!!!

OMG.....Great Hot Story....Thank you so much for sharing it with us....