CHARLIE
Charlie came over to pick me up we were going out on the town to try and pick up some babes. It was the same thing we had been doing on Friday nights for the past three months. Sometimes we got lucky sometimes not. Charlie sat on the couch across from me I was in the arm chair. I asked him if he would like a beer before we went out. I came back with the beers and a shot of Jim Beam for each of us. I noticed that he had picked up last years Halloween photo album and was looking through it. I sat down next to him on the couch to narrate some of the pictures. He had the book open to a picture of me in my hookers outfit. Short black leather skirt, Leather halter top, Fishnet stockings and four inch heels. He looked at me and then looked at the picture and then at me and then at the picture again finally saying "Dennis, Is that you ?" I blushed slightly and said "Yes." He said "That is incredible you are absolutely gorgeous." I told him "I dress up as a girl every year for Halloween, Would you like to see the pictures." As I passed him the shot of JB. He downed it in one gulp and took a drink of his beer. I got up and got the well looked at photo album from the shelf and returned to sit next to him passing him the album which he laid on the coffee table opening to the first page where I was dressed as the Homecoming Queen when I was sixteen. There were many, The bridesmaid, The Bobby Soxer, Alice in Wonderland, The Hooters girl. After a few pages he turned to me saying "You are incredible." As he looked me up and down. For some reason I looked down noticing he had a raging hardon that was about to split his zipper wide open. I have never had sex with a man before but I suddenly wanted to wrap my lips around Charlie's cock, Pushing these thoughts aside I asked him which one he liked the best he turned back two pages to one I had done two years ago, The school girl. A lacy whit blouse and a plaid knee length skirt. I had liked that one too. I got a lot of male attention that night. Then I asked him "Have you ever dressed up as girl before ?" He replied "No, But I once wore an Ex girlfriends nighty for a few minutes before she tore it off me in a fit of passion besides how could I compete with this ?" Pointing to me in a cute little black and white sundress from three years ago. He said "Are you a crossdresser ?". I replied "Maybe but I only go out dressed like that on Halloween." He then asked "What are you going to wear this year ? Halloween is only a month away." He kept looking at the pictures and looking back at me. I said " I have a lovely little black Cocktail dress would you like to see it ?" He replied to Quickly "Of course I would love to." So I walked back into the bedroom and got the dress from my closet looking at all the dresses on the right side of my closet you could almost believe a girl lived here. I also grabbed the black pumps and garter belt and returned to the living room. Placing the garter belt and Pumps on the coffee table I held the dress up in front of myself posing I asked Charlie "What do you think ?" He picked up the garter belt feeling the silk and lace and replied "I think you will look awesome I can't wait to see you in it." I don't know what came over me as I looked at his bulging crotch and slowly moved up until I was looking him in the eye's and asked " Do you want me to put it on for you ?" He took a long drink off of his beer and reached down adjusting his cock in his pants. I heard a slight quiver in his voice as He replied "I would love for you to wear that dress for me, But I may not be responsible for what happens afterward." I took the garter from him and said this may take a few minutes. I went into the bed room and quickly undressed going into the bathroom and shaved all over I then pulled the rubber band from my pony tail and bent forward at the waist brushing out my hair I flipped it back and felt it fall tickling my shoulders reaching under the sink I pulled out some curlers wetting my hair a little I strategically rolled a few into my hair. Going to the dresser I selected and pulled on the tight and skimpy lacy black panty's tucking my now hard cock back between my legs. I turned looking at the mirror and got an idea. Gathering up the silky undergarments I stepped out into the living room Charlie looked up from the photo album caressing himself thru his pants his eye's growing wide as he looked at me. As skinny as I am I have very large tits for a man. I pulled the black lacy bra up clipping it in front turning it around adjusting the shoulder straps and arranging my tits. Charlie laid back to watch still fondling himself. Next I put on the garter belt pulling up a chair I sat down in font of him and rolled the sheer stockings up my legs passing the garter straps inside the panty's I clipped them on to the stockings. For added effect I ran my hands caressing my now very feminine legs. As I stood up I adjusted the garter straps I reached up cupping my breasts. I then picked up the silky black slip and pulled it over my head. The silky material sliding over my lace covered tits coming down to caresses my stocking covered thighs was just the feeling I had been looking for and the reason for doing this. The added thrill of Charlie's lust filled attention had me completely turned on. I asked Charlie if I could get him another beer. He nodded yes and I turned to walk into the kitchen. I could feel his eye's staring at my butt. I got his beer and peeked thru the opening in the wall to see him reach into his pants and stroke his confined hardon I reached down to stoke mine through the silken panty's. Returning to the living room just as Charlie finished pulling his hand from his pants. I gave him his beer telling him I would be back soon. He still could only nod. Back in the bedroom I pulled out the rest of my hair accessories and my makeup case proceeding to the bathroom using the curling iron and a little hair spray after removing the rollers I applied some eye liner shadow a little blush and some red lipstick. The effect was almost complete I unzipped the back of the dress and pulled it on zipping the back with some difficulty I straightened my slip and then the hem I got the pearl ear rings and necklace and my black pumps. Finally allowing myself to see the results in the full length mirror. The girl I saw looking back was gorgeous. Shoulder length reddish blond hair, Pretty blue eye's with long lashes, Long shapely legs, Nice Tits and a pretty face with full red lips, Wearing a very feminine Black velvet dress with a short flared skirt. I could not resist cupping my breasts again and running my hands down just to feel all the silky cloths inside and out, What an incredible turn on. The girl of my dreams. I had the feeling she was about to lose her virginity to Charlie. With practiced steps I sashayed into the living room. Charlie rose to his feet his mouth dropped open, I raised one hand and Pirouetted for him asking "What do you think ?" He said "Oh my god, You are beautiful." I walked around the coffee table to him. He said "I would give my left nut for a girl who looked like you." Walking up to him reaching down I grabbed him by the cock. For the first time I held another mans cock in my hand. I said "Its not your left nut I want its the whole cock. Pulling me close he kissed me full on the lips. I could feel his hands grab hold of my butt squeezing me. The feeling of his strong arms feeling me through the silken garments made me just about cum in my panty's. Breaking the kiss he looked me in the eye's and said "I have never kissed a guy before, Never mind my best friend. But you have me incredibly turned on." This he did not have to tell me, I was still holding his cock through his pants and started to slowly stroke him. He continued "I have always had a fantasy of having a gorgeous shemale. He reached up and cupped my breasts in his hands. I replied "I also have never been with another guy before, But have often thought of it but only when dressed as a girl and you look good enough to eat." As I undid his belt and fly allowing his pants to fall around his ankles. He pinched my nipples as I pulled his jockey shorts down and allowed them to fall on top of his pants. His cock which was a little bigger than mine was sticking straight out and pointing right at me. I reached down and cupped his balls in one hand as I grabbed his shaft with the other and slowly started stroking him grasping him about the base I slowly stroked him to his silky smooth head a little drop of clear fluid appeared at the tip. I dropped to my knees still holding his cock looking up I could see him looking down with glossy eye's. Pulling my gaze down I found myself face to face with my first cock leaning forward I licked the drop of cum off of the tip. Charlie gasped and I swear his cock grew an inch in all directions. Holding the shaft tightly I took the whole head into my mouth and sucked as I wrapped my tongue around it and started to bob up and down as I stroked the part I could not get into my mouth. Charlie moaned "Oh god that is incredible." I reached up and started caressing his balls. I could feel tiny spasms racing down his cock. I took as much of it in my mouth as I could. Charlie bucked his hips forward as he grabbed the back of my head suddenly I swallowed the entire cock. Charlie moaned "Yes suck that cock bitch take it all." I sucked back until I had only the head wrapping my tongue all around it still stroking when he made a grunting sound and bucked forward again. This time I let him fuck my face. On the out stroke I sucked as hard as I could and furiously stroked him with my hand. I knew I had him as I felt his cock grow even bigger as his nuts tightened. He swayed on his feet as he said threw clenched teeth "I cumming !!" He grabbed two handfuls of my hair as he erupted into my mouth with surprising force. I was expecting to spit it out but to my surprise I liked and swallowed every spurt and hung on for the ride I could feel his balls spurt with one hand his cock pulse with the other his cock head throb with my lips and tongue and his cum spurt off the back of my throat. I was so completely turned on I could not believe I was completely dressed as a beautiful girl on my knees with my best friends cock spurting in mouth and loving every spurt. I leaned forward and swallowed his entire cock until his pubic hair tickled my nostrils and wrapped my lips as tight as I could and sucked back. I thought he would blow out the back of my head. He moaned "Oh baby, You beautiful girl." My own cock tucked back between my legs was so hard trapped in the tight lacy panty's it hurt. I spread my legs a little and wiggled my butt and it sprung free of the panty's up into the silken softness of the slip. I thought I would cum myself. Charlie finished his last spurt so I held his cock and licked the head looking up into his eye's watching him squirm. Finally I grabbed his cock by the base and stroked it all the way to the tip getting a moan from Charlie and one last big drop of cum on the tip of his cock which I reached out for with my tongue and licked off . Charlie collapsed back on the couch. I moved forward between his legs and leaning my tits against his cock he leaned down and kissed me and said "That was incredible, Will you marry me ? Where did you learn to do that ?" I answered "Natural talent, That was my first from this end." I stood up feeling my throbbing cock bob up and down into the silky slip peeking out from under my dress. Charlie reached out grabbing hold of my cock pulling me closer he lifted my skirt and pulled down my panty's while stroking my cock. I was already on the verge of the biggest cum of my life. I looked down and he was already half erect again. Letting go of my cock he pulled me down sitting on his lap facing him and ran both hands up under my dress until he was cupping both of my tits pinching the nipples pulling the cup on the bra down he started to bite my nipple after a while he bite the other one I could feel our cocks rubbing together after a while. He stood me up again tickling down my sides stopping at my cock momentarily moving down to caress my stocking covered legs. I was threatening to cum at any moment. Finally he returned to my cock gently taking the weight of my balls in his hand he steered my cock to his waiting mouth with the other completely licking the head paying extra attention to the dab of clear cum at the slit. I knew he did not have long before a full scale eruption happened holding up my skirt to see what was doing I ran my other hand through his soft short hair and said "Lick that pussy Charlie." Wondering what a pussy would feel like now, Or better yet with Charlie's fat Cock in it. Charlie looked up at me suddenly taking most of my cock in his mouth while stroking back with his hand he pulled back furiously while stroking all the time. I felt as though I had stepped over a cliff. The sperm boiled forth, Charlie held on for the ride spurt after spurt, Charlie told me latter I screamed as I grabbed hand fulls of his hair and drove my cock all the way down his throat. He continued sucking and swallowed every drop. Waves of passion cascaded through me, My cock seemed to cum forever. Finally conscious thought returned Charlie had me by the legs and laid me back on the couch looking up I smiled and said "Where did you learn that? Will you marry me ? That was fantastic." Charlie said "I can take no credit for that." As he leaned down to lick the last drop from my cock head, Sending little electric charges through me. "That was all your doing. You are one hot little Babe, Dennis or should I say Denise. It suits you better." I sat up pulling him to me and kissed him stuffing my tongue down his throat. Breaking the kiss I said "This is going to be interesting, Best buddy, This is going to be interesting."