Sorry but I try to be this writer that I am not, so please understand this what I dream of when I take long drives while traveling for work. I am a cross dresser like most of you most likely are but just can not take the next step. When I work away from home I dress fully and chat on-line like a women but I am up front first off of what I am. If at this point in life if I could have I would love to have lived these fantasies.
It was Halloween my friend Al was giving his yearly party and I needed to get a costume. I never told him about my cross dressing until about a month before the party.
I have known him for about four years now and yes Al is a gay man. No matter how many times he tried to drop hints about us or me getting to together I could not begin to think I wanted another man. I had tried to look at men in a sexual way but it never turned me on. What I did not tell him was I fantasized about cocks when I dressed as a woman. See no matter how hard I tried I could not find myself with just a man but dressed as a woman I was turned on by having a cock inside me. I used dildo many times on myself and loved it and wanted to be feminized by a women to only be used as a cum receptacle. About this time in my life I found out about transsexuals and would have slept with them if I could have found one.
Al and I had a few drinks and were talking about when he knew he was gay. He said knew when he was around 12 or 13 that he like boys more than girls. This led me into telling him how when I was 8 I started wearing my mother's nylons. I told him about when I was in the third grade I was fascinated by my teacher's stocking clad legs. I would get a hard on thinking about them. Then one day my mother left some of her knee highs out, so I took them to my room and tried them on. I was hooked ever since; I told him that I could pull them up to my thighs like thigh high stockings at that age. I explained to him over the years I would get into my mother's and sister's pantyhose and stocking and would have fantastic orgasms wearing them. I told him I would love to be fully dressed as a women in public but was always afraid of being found out. At this point he said why don't you come to this year's party dressed as a women, with all of his friend nobody would seem to care. Besides he knew plenty of drag queens and it did not bother him.
After a couple of weeks and us going back and forth on the subject I said I would do it but I would need some help. So with the help of our mutual friend from the fitness club I was ready to go through with it. Liz was an over weight girl that was infatuated with Al.
She would help him get ready for the party every year, so this year Al asked her if she would help me with my costume. We told her that I wanted to go to the party dressed as a women. Boy was she ever willing to help. We started out by shopping; since I was nervous about purchasing thing for myself she would go with me to purchase item for myself .
Since I wanted to dress sexy we started out shopping for panties and stockings. We went to Carson's Department Store and got me a matching set of bra, panties and garter belt set. The set was black lace trim paddled bra, the panties were shear back with lace front bikini style, and the garter belt was all lace with six straps. I was shaking while I pick them out and my hands were so sweaty I kept rubbing them on my pants. Next we had to find some shoes. She had me get my foot measured and pretended to try on men shoes as she would go around and point to women's shoes that she thought I might like. My cock was rock hard thinking about me being able to try on all those women's shoes but I was to afraid. After looking at many pairs I decided on some four inch stiletto strappy sandals. Needless to say I excused myself to a secluded restroom stall and jerked off. After I had regained my composer we continued shopping. We looked at many dresses and I finally pick out a black cotton dress with long sleeves, choker collar with pearls inset in the collar, and with slit up both thighs. We took it to the men's dressing room wear I could try it on. Thank god I had just jerked off other wise I could have stained the dress while I was trying it on. It was perfect it fell about two inches above the knee and the slits stopped about mid thigh. As I was admiring myself in the mirror the salesman asked if needed any help, I almost had a heart attack, I fumbled around trying to get out of the dress as fast as I could but he said please take your time and don't be embarrass he was going to direct people other away. I quickly put my own clothes back on and hide the dress under the pants I had brought in. He kept his back to me and asked if everything fit ok and wanted to know if I was ready to check out. Mean while Liz hurried toward me and took the pants and dress and said sorry she accidently had handed me the dress by mistake. The young salesmen said yes he understood and said he was still willing to ring them up if that's what we wanted. Liz looked at me I nodded yes so he took them to the counter and rang us up. Before he handed us the receipt he wrote something down on it. He made sure he looked me in the eye and said if I ever needed anything else please feel free to call. Later I found out it was his number.
When Liz and I stopped for lunch we laughed about how I was just picked up by the guy from Carson's, she wanted to know if I was gay and what I thought of him. I told her I was not gay but it did turn me on that I was almost found out. She said I should still call him and invite him to the party. I said I would think about it. I did think about it I was wonder what it would have been like to have been in that dress and on my knees sucking his cock in the dressing room. Liz then broke that though and said we will have to get me some stockings and make-up. So after lunch we went and pick up some stockings. She wanted to know if I would be shaving I said shaving yes as I rubbed my face, she said no silly your legs. I told her I did not think of that but yes I was as I always want to slip on stocking while I had smooth shaved legs. We went back and picked up a pair of black shear stockings and many more, as I do love being in them. Our trip was done after we got my make-up and nail polish.
It was Saturday morning of the party I got in the shower and began to shave my entire body; it was one of the most arousing sensations. After my shower a polished my toes with bright red nail polish, my legs and feet were now looking more fem then I could imagine. I then had to my finger nails for the last few weeks I let them get long and shaped them as Liz showed me. My transformation was going well it was turning me on I never would have thought what this was going to get me into later. I then put on the panties, garter belt, bra and stocking soon after my nails dried. I looked in the mirror and was aroused by what I saw. It was only ten in the morning and still had hours before I would go to Al's to have Liz help finish my transformation. I hung around my apartment just in my lingerie and could not help myself from wanting to clean everything in site dressed as I was. Time flew by and it was time to get with Liz at Al's house so I put my genes and tee shirt on over my women's garments. I gathered the rest of my attire for the party and slip on my gym shoes for the drive over. I could not help myself when I got into the car I pulled of my gym shoe and replaced them with the strappy sandals for the drive over.
I pulled into Al's driveway then got out of the car; I love the look of my stocking clad feet in genes and heels as I strode to Al's door. I rang the door bell and Al met me at the door, he saw that I had on the heels and said what a slut I must be for showing up at his door in such heels as that. I walked in and Liz was waiting for me, she was just as excited as I was to finish my full transformation. She said she wished she always had a sister that she could play dress up with and this was going to be the most fun we both would have. She was amazed how well I had done with my nail polish and wanted to see the rest of my underwear. So we used the spare bed room to finish changing into my grille outfit. I was getting more aroused by being help and complimented by another women on how I looked. She then proceeded to help me with my make up and hair. My final transformation was amazing we showed Al and he said I was going to make a lot of girls at the party jealous.
I was now fully a women for the party that was to start in about an hour. I now had an ubiquitous erection and needed to excuse myself from helping set up the party for a few minutes. I went to the bathroom to jerk myself off. While I stood in front of the bathroom mirror looking at this new me Al barged in and asked if I needed any help. I was dumb founded with my dress hike up and panties pulled to one side and my hard on exposed, Al step behind me and grabbed my cock for a reach around. I gave into his advances as would a horny women would. I put both hand on the sink counter an slightly bent over. I closed my eyes and stood up ever so slightly in my four inch heels letting this man stroke my cock or as I imagined my clitty to an new orgasm I never had before. I never new how much another man could make me feel this way. He knew how to grab my clitty and stroke it better than and girlfriend I had ever had. I was aroused how he stepped in and forced me to submit to his control. He stroked me off till I came on the sink counter then by pushing my head to the seed I just left on the counter I proceeded to lick up every drop. I was now lost in thought I was this women who would submit to any man and do as he pleased so I could orgasm as he got me fully aroused. Without a word Al let me as I straighten my outfit and awaited the guess arrival.
People started showing up in numbers and dressed in there Halloween costumes. Through out the night I was complimented on my looked and people wanted to know how long I was doing this; me dressing as women. They were amazed that this was my first time dressing up. Through out the night I was complemented by the woman and groped by the men. In fact I do not know why I slow danced with a guy dressed as a gangster, he held me tight with his hands on my ass and pulled me tight till our hadrons touched. I told him I was spoken for and thanked him for the dance. I was now fully aroused again and had to sit down. I was hit on many more times by guys and guys with girl friend as the party wore on. It was late when I noticed the guy from Carson's had showed up at the party.
Liz came over and sat next to me and told me she had called him and invited him to the party, she then proceeded to tell me I should go talk to him since he did not know anyone else here. I protested but it was to late she got up and invited him to sit down next to me. He introduced himself as Kevin and Liz jumped in and told him I Natalie. I gave her a dirty look then shook hands with Kevin. I did not know what to say so I asked him what he wanted to drink, thinking this was an accuse for me to get away. He said sure he would take a beer, so I got up to go fetch him one but he got up and followed. On our way to get a beer he said how hot I had turned out. I turned to him to complain but said thank you. He told me he was sorry he tried to hit on me by giving me his number at the store and explained that Liz had told him the whole story on what I was doing trying on the dress. I said it was o.k. and I understood how it might have looked. We got him the beer and were hitting it off quite well man to man.
We went back to the couch and I opened up to him explaining that I started wearing my mother's and sister's nylons and that this was something Al and Liz had talked me into doing for Halloween. He then told me about how he was bi-sexual and when he had his first experience while he was 12 with boy how was 16. We talked for about an hour and noticed many people had started to leave since it was getting late. He said he should be going soon since he had worked all night till closing at the store and that was why he got to the party so late.
He got up and said he needed to know where the guy running this party had put his coat. I said I knew where the his coat should be and would help him get it. Without knowing it I held his hand as I lead him to the spare bedroom where Al had put the guest coats. As we went down the hall he said I did make an amazing looking women I turned and looked him in the eye as in the store and thanked him. When I lead him into the bedroom I noticed there were only a couple of coats left. When I turned on looked to ask him what coat was his he surprised me by standing almost on top of me.
I was startled by how close he was standing next to me. Again we made eye contact but this time it was different I could not look away. He reached down and lightly grabbed my hand and held it in his. He said again how wonderful I looked as I put a hand on his shoulder and said thank you. I was being to have thoughts of what it would be like to kiss him at that point he lend in and we touched lips. Now I felt his other hand on the small of my back and with a little pressure from him he pulled me closer. With natural reflex I put both of my arms up over his shoulders and kissed him fully. He put both arms around my waist and pulled me up closer at the same time. We kissed deeply neither of us wanting to stop. He lend into me forcing me onto the bed. He followed me down as we sat side by side kissing hungrily as he put a hand on my knee and slowly moved up my inner thigh to the top of my stocking leg. I began to regain composer and pulled away. He said what was wrong. I told him flat out I was a guy and what was he doing. We stared into each others eyes and he said he wanted me ever since he was peaking in the dressing room watching try on the dress I was wearing. I was taking aback but what he said and could not believe that he did that. I could believe what came out of my mouth, I told him about what I had thought of doing to him when he came to the dressing room door. I said I wished to have gotten on my knees and sucked him off. He than grabbed the back of my head and kissed me again.
After we released from our kiss he whispered in my ear and such a naughty girl having thoughts like that should taken over a knee a spanked. My god I almost came in my panties when I heard that. Again with what he said I could not believe what I did next. I stood up and bowed my head clasping both hands in front I then said yes sir I need to be spanked. He positioned himself on the bed so his lap was straight out in front. I then told me to bend over his knees. I slowly lowered myself over his lap placing both hands on the floor and crossed my ankles. He ran his hands up and down my nylon clad leg loving the feel of them. He put one hand up my dress and felt my panty incased ass. Then he told me little girls should not have dirty thoughts like that and when they say such thing they need to be punished. When I did not answer he swatted my ass hard and said did you hear me. I jump and said yes sir. He then proceeded to spank me hard ten more times. He asked if I was sorry for having such thoughts and I said yes but be said he did believe me. Then I was told that I was going to have my dress raise and spanked some more. I was a harder than I have ever been at this point. I felt my dress go up and got many more swats on my pantyed ass.
During the spanking we had a small audience; it was Al and two of his friends. Al asked what did she do. Kevin then told him about what I said when I was in the dressing room. Al the told him about what he and I did in the bathroom before the party in front of Kevin and the two other guys. I was taken back on what was just said while still over Kevin's lap. Kevin then asked me if that was true, all I could do was say yes. Kevin told me to stand up; I stood up in front of everyone with my dress hiked up. He then told me to bend over and grab my ankles. I looked at him and looked over at everyone else then he said young lady better do as I told you. I then bent over grabbing my ankle near the ankle straps of my sexy shoes; I was almost turned on by looking at my painted toes in black stocking in my sandals as was what was going to happen next.
As I was bent over admiring my feet I could here a belt buckle being released and the whoosh of it being pulled from Kevin's pants. Kevin then pushed my dress up higher and told everyone look a this slut she has he panties on the outside over her garter belt, and he asked me hey whore were you expecting to get fucked tonight. With that he grad the waist band of my shear ass and lacy panties and pulled them down my thighs. Kevin asked the other guys how many strokes should she get, then someone said it should twenty but Al said it should be twenty three that how old she is. I then felt Kevin's hand placed on the small of my back and the first strike came. I jerked and he waited for me to settle then another and another each time waiting for me to get set for the next one. On about ten I reach up to rub my ass only for it to be slapped and told to hold that position or we would start over again. My face scrunched with the next 7 or 8 hits with belt. Al said hold on and give her a break until he came back. When he came back I peak over at him coming through the door with Liz and a wooden paddle. Kevin said that I would need only to take five more. I braced when he put his hand back on my back a gave my the hardest swats I have ever had.
When he was done I stood up as I was told and show everyone his work. He ran his hand over my fire redden ass and bent over and kissed it. At this time Liz said look at what that girl did she has put a run in her stocking. She told everyone that no girl would ever be caught with a run in her stockings and when she was younger her mom would get mad and discipline her for ruining hers. Kevin ask how her mother disciplined her so Liz proceeded to tell everyone that her mother measured it and spanked her for every inch. Al then went back out of the room and got a dress makers measuring tape. I was told to take off my heels and lay face first on the bed. Liz came over and measured the run. She proclaimed it ran 12 inches from mid foot up the back of my leg. I was told to get up on my knees on the bed and face down. With that Kevin again swatted 12 more times.
My punishment was not over yet but it really wasn't really all a punishment for me I was so turned on by the whole seen that I was willing to do anything Kevin demanded of me. I know had be come the submissive girl I always knew I wanted to be and this guy was going to take me there. I was told to get off the bed and strip out of my dress in front of all. So I kicked my panties the rest of the way off and pulled the dress up over my head. I was now just standing there in my bra, garter belt and stockings. My hard on was standing straight up for all to see my humiliation. This was not the last of it I was told by Kevin that I was to live out the fantasy I had that day in the dressing room. I looked at Liz I looked at Al and the other two guys, and then I dropped to my knees in front of Kevin. I looked again into his eyes and knew that this is want I wanted. I undid his pants and pulled them down I grabbed the waist band of his underwear and pulled them down also. I grab his cock in one hand and started stroking it, he moaned, I loved the feel of his erection so smooth and responsive to my touch. I guide to my lips and kissed its tip tasting the pre cum he must have gotten from spanking my ass that felt so painfully good. I lick his shaft from his balls to the tip then let it enter my mouth. As I let it slowly slid into my mouth I looked up again into his eyes as he slowly closed them. I began to bob my head let that smooth cock run back and forth over my lips and tongue. At this time I felt some climb onto the bed next to me. I glanced over and it was Liz lying down naked with one of the guys mounting her. I felt Kevin's hand grab my head to kept me in rhythm to his liking. I felt him pulsing in my mouth so I grab his shaft in one hand and stoked him while I kept my lips at the sensitive part of his cock. He began to know fuck my mouth as I felt two other people stand next to me. Each one grabbed each of my arms and lead my hands to there cocks. There I was a cock in each hand and one in my mouth. At this point Kevin moaned and shot his first stream down my throat. I felt my anus to my own shaft have a sensation like I never had before it was some kind of orgasm without me cumming. Again and again Kevin shot his seed into my mouth and I swallowed every drop not wanting to spill. As he pulled his know sensitive rod from my mouth a little stand of cum form from my mouth to his tip until it broke.
At this time Liz and the another guy were going at it hard she smiled at me and got right back to what she was doing. In them mean time the two cocks I was stroking pulled away as Al's hands went to my shoulders and positioned me on all fours. Al laid down in front of me and offered up his cock. Then I felt a cool liquid run down the crack of my ass. Then someone spread my ass cheeks with one hand as the other with one then two fingers spread it into my hole. Al grabbed my head and forced it onto his waiting shaft. As I start blowing my friend I had a wonderful sensation of the other guy entering me slowly and expertly from behind. I was fucked in both ends slowly at first then when I pushed back with my garter belt framed ass the guy from behind got the signal I was ready to take him full force. Al came fast in my already fucked mouth and this brought my to another suedo orgasm I felt deep in my ass. I was leaking cum from my own cock as the guy behind ran in so deep that he was hitting my prostrate. I was then reaching back for my own cock as Kevin pushed my hand away and got under to suck me off. As soon as Kevin put his warm mouth around my shaft I spilled cum into his mouth. My cumming had tighten my ass around the guy fucking me shaft that I could feel the stream of his jism enter my bowels. Kevin then put his hand under my chin and lifted my lips to kiss his as he had saved some of my own seed for me to taste. At that moment Liz came and the guy on top of her pulled out her jumped off the bed and grabbed my head and shoved his pussy slicked cock into my mouth. He fucked mouth with force making me gag but I wanted him to cum in me so badly I was will to take it. After five quick thrusts he came also.
I was spent and hoped this only the beginning off a knew life still for me. As we all spent the night at Al's house in the morning I had awoken with me in Kevin's arms. That morning we were still horny Kevin and I and he was so turned on by my stockings I put them back on for him. As I lay in bed he began to rub my feet. Then I proceeded to take my stocking feet a stroke his wonderful cock with them. He the turned me over and shot his load all over the bottom of my feet and up the back of my legs. I was then made to join the others for breakfast in cum cover stockings as more punishment for now getting him turned on. Liz then said I should have to clean the kitchen dressed as I was while all the others watched. I was so turned on my erection never went away. Until Al came up behind me with yet again another reach around that I had to clean up with my tongue while everyone watched. For the rest of the day I was put back in my dress and service and service everyone. I was now never going back to being a man. Kevin was going to see to that.
Hope you enjoyed the story some is true most is not. E-mail me if you please. Natalie