Halloween Story

This is a true story. I changed the names and filled in the conversation much as I remember it from thirty years ago. I hope you enjoy it as much as I did.

When I was much younger I passed as a girl much easier than I do now. My earliest memories of crossdressing were when I was 7 but a girl I had dated when I was 17 used to dress me up and we would go out together. By the time I was 19 we had broken up but the damage had been done and I was hooked and I used to go out dressed on my own.
I have a condition called gynecomastia where a male grows female like breasts I got large B or small C cup breasts when I was 16 or 17. I was horrified at the time but eventually realized how lucky I was being a crossdresser. I had also grown my hair out to almost shoulder length. Being the late 70’s this was in style at the time. I lived in a small one room apartment by myself.
It was early September and I was thinking what to do on Halloween. One of the drag clubs I frequented in Boston always had quite a party.
I had always been intrigued by the catholic school girl uniforms and decided this was a good opportunity to wear one. When I was younger a couple of my friends went to a Catholic school and I remember going with them one time shopping for school uniforms.
The little store was still there. When I walked in the owner, a little gray haired lady gave me an evil stare and didn’t initially want to sell me anything. I sweet talked her saying it was for a party where the boys had to come dressed as girls and the girls had to come dressed as boys eventually she gave in and smiled when I asked her if she thought I would make a pretty girl. She produced some larger sized garments from the back. At her suggestion I bought a green plaid pleated skirt, a white Peter pan collared blouse, a cross tie that matched the skirt, some knee socks and she even found a pair of maryjane shoes in my size in an old discolored shoe box. I could tell she was getting into it, before I left she had me try everything on and insisted I get a black headband with a bow on it.
Having spent way too much money I made it home with my treasures (I still have the outfit but could never fit into it now)
On Halloween Night I closely shaved every hair on my body except the ones on my head. At the time my hair was kind of a reddish dirty blond color that I combed straight out and curled the ends under a little using a curling Iron, some very light makeup, a little eye liner, with pink blush on my cheeks and light pink lipstick. After putting on some white cotton panties and a plain white bra I dressed in the uniform. One of the best parts of crossdressing for me is the actual dressing and this was a fantasy come true. The lady in the store had made sure everything fit perfectly. I buttoned up the blouse and my breasts were just poking out enough to strain the buttons a little. It was a thrill to pull up the skirt and tuck the blouse in. I had never worn knee socks before. (I am more of a stockings garter belt type girl.) The maryjane shoes were very cute and fit perfect and were very comfortable and easy to walk in with only a one inch heel. (Why she had a pair of size 12 in the store I will never know.) I finished the effect with the cross tie and then arranged the hair band and bow in my hair.
When I was done and looked in the mirror I could not believe how good I looked. Even though I am close to six foot tall. I looked like a sweet innocent school girl. Not one of those slutty made up caricature school girls in a ridiculously short skirt, but a real teenage school girl in a just above the knee pleated skirt. I had also bought this little lunchbox looking purse that I put a little makeup my wallet and a brush in. With one last look in the mirror I made my way to the car. My neighbor across the hall was going in as I was coming out. I could see him fumbling with his key as he tried to look at me. I thought he was going to pass out when I asked him if he liked my costume. He said he would have hit on me if didn’t know I was a guy and if he was in the habit of hitting on under age girls.
I finally made it into Jacques Drag bar. I must have been hit on at least 100 times, by guys, girls, other crossdressers, gay men, lesbians. Apparently school girls are on everyone’s menu. I don’t think any of them except for a few crossdresser friends knew I was a boy. I was loving all the attention and the place was hopping. Eventually a bunch of crossdressers that I hung out with wanted to go over to a disco near Fenway Park called the Metro. Halloween night is a night when a crossdresser can go almost anywhere relatively safely. I agreed and found myself in a packed nightclub at midnight. The drinking age at the time was 18 and the bouncer who checked my ID did a double take but let me in.
Now I was being hit on by straight men and I was getting a little nervous. This one rather cute guy dressed as a baseball player kept flirting with me and buying me drinks even though I kept my distance. The other girls kept pushing me to dance with him. Finally I gave in and danced. After a couple of dances and drinks I was feeling a little giddy and drunk when he maneuvered me to a less crowded area. I almost had a heart attack when he moved in close. I could feel his erection press against me and he kissed me.
I had once been kissed by a guy before and fantasized about it but had never had sex with another guy before. I pushed him to arms length and said,” I need to let you know that I am not really a girl.” His eye’s got really big and he looked me up and down and said,” You have got to be joking, I just thought you were a tall girl.” Then he said,” You had to have know that if you came in here looking like that you would get hit on by guys.” Sensing his discomfort but not any negativity I moved a little closer smiled and replied,” What makes you think I don’t want to be hit on by guy’s?” I could see he was nervous but I also noticed there was now a noticeably larger bulge in his pants. He replied,” You look exactly like a girl I knew when I was in school who attended the local Catholic School. I had the biggest crush on her. When I saw you I thought you were her. I used to have fantasies about her all the time.” Smiling I moved closer my hand came to rest on the bulge in his pants as I asked,” What did you do in those fantasies, anything I could help you with?”
I could tell he was still nervous as he moved his hand up onto my back and slid it down coming to rest on my butt turning he kissed me again said,” Yes, I think you may be able to help me with a couple of those things and maybe with a few I didn’t know I had.”
He turned me so his front was against my back and pulled me closer. I could feel his cock pushing my skirt between my legs. He reached around placing both hands on my midriff and ran his hands up until he was cupping my breasts. I was definitely turned on by this time and was afraid I would start to tent out my skirt. Not really expecting any action tonight and having a flared skirt I had not done any tucking.
He leaned forward and kissed my neck and whispered in my ear,” These are real breasts I think you are kidding me.” I turned my head and kissed him and said,” There is only one way to find out if you are man enough.” Slowly he slid his hands down and did a sharp intake of his breath as found my stiff cock. Moving back up to my breasts he said,” This is going to be interesting.” As he started to gyrate his stiff cock against my backside.
Just then the call went out for last call. I rotated in his hands to face him. My flared skirt hid my erect cock but there was no mistaking it as we embraced and kissed and our cocks rubbed together.
Breathlessly he said,” My roommate is out of town for the weekend. I could sneak you into my dorm just up the street at Boston College.” I reached down and cupped both hands around his cock and said,” There is nothing I would like better.”
We headed for the door, A couple of my less passable crossdresser friends called out and made some rude comments as we passed them on the way out.
It seemed like moments latter we entered his dorm room. It was a disaster clothes strewn about. He made a couple of rum and cokes from what he called his hidden stash. I walked about and looked at the piles of stuff when I turned to him I noticed he was staring as he said,” Do you know how pretty you are? For someone with a thing for school girls you are an absolute wet dream. I have always fantasized about girls in those uniforms” I smiled and did a pirouette for him and thrilled at way my skirt ballooned out. I walked over to him and said,” Thank you, I’ve always fantasized about these outfits as well, and the difference is you always fantasized about the girl in the uniform. I always fantasized about being the girl in the uniform.” Tonight is just as much a fantasy for me as you.” Pulling him close we kissed and ran our hands down each others backs.
When the kiss ended he said,” I’ve never done anything like this before.” I smiled and said,” Don’t worry just pretend I’m a girl.” Reaching down I undid his belt and pants followed by his jockey shorts letting them drop around his ankles. He reached up and fondled my breasts and said,” That won’t be to difficult.” I maneuvered him back as he stepped out of his pants and sat on the bed. Standing in front of him I unbuttoned and removed my blouse then dropped to my knees in front of him. Looking up he kissed me as I fondled his cock and balls.
Moving back a little I bent and licked the drop of pre cum that had beaded on the tip of his cock and then slowly sucked half of his cock into my mouth. I heard a sharp intake of breath as he said,” Oh god this is hot.” I slowly started to bob my head as I stroked the base of his cock and fondled his balls. He surprised me as he suddenly started to spasm and said,” Oh god.” And spewed into my mouth after only lasting about 60 seconds. I hung on and sucked him for all he had to give which was quite a bit. Finally when he was done I stroked him from the base to the tip getting one last drop and licked that off.
I looked up and smiled. He was embarrassed and said,” I’m sorry I had hopped that wouldn’t happen.” Moving up beside him I said,” don’t be sorry, that was fun.” Moving in I kissed him. He was a little reluctant at first but gave in. Turning I asked,” Could you unclip my bra?” I felt his hands come around and first fondle my breasts though the bra and then after a bit of a struggle with the clasp fondle them without the bra pinching my nipples.
When I turned back I noticed he was already almost erect again and I lay back on the bed. My cock was putting up quite a tent in my skirt. He moved around until he was straddling me and leaned down and nibbled on first one nipple and then the other and asked in an oddly innocent way,” If you are really a guy how come you have such nice tits?” I giggled and said,” It’s a condition called gynecomastia. When I was 16 I just grew them. I think I have one to many female chromosomes. Most guys get a lower voice and big muscles I got tits.”
He kissed me again and said,” I have always had the problem of Cuming to soon. The girls always made fun of me so I’ve been embarrassed to try again. I thought it might be different with you.” I pushed him over and grabbed his now fully erect cock again and started stroking as I said,” I think it’s cute and I bet you last much longer the second time.” As I once again started sucking his cock.
I felt him start to reach up under my skirt and hopped he liked what he found there. I felt him tentatively wrap his hand around my over excited cock as I sucked most of his not overly large cock into my mouth. Slowly he started to stroke me through the cotton panties. I stopped sucking his cock and stood up in front of him and went to remove my skirt he stopped me and slowly pulled it down himself as it dropped about my ankles he fondled my cock through the cotton panties for a moment and then slowly removed them as well. He sat here and looked at me while he unbuttoned and removed his baseball shirt and then placed his hand over my cock and said,” You are still the prettiest girl I have ever seen. I had thought that the illusion of girl would go away with the clothes but you keep getting better”
Moving back onto the bed in a more or less 69 position I once again started sucking his cock. I felt his hand as he started to stroke my cock that was only inches from his mouth. I sucked as much of his cock in my mouth as possible and stroked the part that I could not. I just about came on the spot when I felt his tongue lick the tip of my cock. I really started to go to town as I felt him suck the tip of my cock into his mouth.
I could feel myself building as his cock seemed to stiffen within my mouth. I wanted us both to climax at the same time. Some how I managed to hold myself off until I felt his cock jerk within my mouth. I let myself go at the same time. While I kept his cock in my mouth and sucked him for every thing I could get he pulled mine out and milked me with his hand. He must have pumped at least a gallon down my throat. The feelings emanating from my cock were so intense it was hard to concentrate on pleasuring him.
Finally we both finished and lay backing in an exhausted state. I looked down to see I had shot all over his face and chest. I got up and pulled a towel from the mess and wiped him clean.
He looked at me and with an amusing smile said,” I like your outfit.” Looking down I realized I only had on knee socks and my Maryjanes. Smiling I climbed back in bed with him.
He said,” That was incredible.” Reaching over he started to fondle my breasts and tweak my nipples. I reached down and found to my amazement he was already starting to get hard again. I started to fondle him as I said,” You want more already? That thing has a fast reset time.” Smiling he said,” I’ve only been with a few girls and each time they only wanted the missionary position. I would get off almost immediately they would be disappointed and that would be it.” I smiled and replied,” I am far from disappointed.”
I must have fallen asleep then because the next thing I knew it was morning and someone was caressing my breasts. Waking up I looked down and noticed that someone had a very hard cock. I reached down to caress it as I started stroking him I asked,” Excuse me but I don’t think you ever told me your name?” smiling he said,” Kyle” and extended his hand to me I stopped stroking him long enough to shake his hand and he asked,” And yours?” I said,” Karen”
We both started laughing. Turning I kissed him and asked,” Would you do me a favor?” he replied,” sure within reason.” I smiled and said,” Would you stick this wonderful thing in my butt?” I leaned over and took the head of his cock in my mouth as he said,” It would be my pleasure.” Getting up he strolled over to his dresser and produced an ancient tub of KY. I smiled as I got up on all fours and wiggled my butt at him. He knelt on the bed behind me. I turned to watch as he lubed his cock and applied a generous dollop right onto my butt hole. I felt as he pushed his cock up against my sphincter and he placed his hands on my sides and slowly slide them back until he was gripping my hips.
He said,” From this angle you very much look all girl. You have an awesome figure, nice butt and very smooth skin.” Knowing it was going to hurt at first I pushed back against him. Taking the hint he pressed forward. Having only done this once before I felt the searing pain of being split in half as the tip of his cock entered. I did a sharp intake of breath and I know I had tears in my eyes. Kyle asked,” Are you ok?” I motioned for him to stop and he went to pull out as I said through clenched teeth,” Just stay where you are for a minute.” After a few moments the initial stab of pain subsided and I pushed back against him.
Slowly he started to push into me until I felt his balls touch mine. Leaning down on my back he caressed my breasts and pinched my nipples and slowly started to fuck his cock in and out of me. Sliding one hand back he started stroking my cock in time with his thrusts and it hurt sooo good. The feeling of having a mans cock sliding in and out of you is one of the great pleasures of life no matter who you are and worth all the pain.
He started to pick up speed and I dropped down onto my elbows as he pistoned in and out of me. Suddenly he slowed and I could feel his cock grow bigger and spasm inside of me the feeling of flooding warmth caused me to spasm in his hand as he continued to stroke me. I don’t know what felt better the warmth flooding inside of me or the massive convulsions emanating from my cock. I had never experienced a full body orgasm like this before. Kyle kept pumping into me as he said,” Oh god” over and over.
Finally he collapsed on top of me pushing me flat on the bed. I could feel his cock shrinking inside of me. Rolling off to the side I heard him say,” No one ever said something like that was possible.” Turning to face him I started to trace little designs on his chest and tickle his nipples. He said,” That was incredible.” I reached over and grabbed the towel and cleaned us both up as good as possible. We both laughed when he started to get hard again.
Looking at the clock he said,” My roommate will be back in another couple of hours.” I smiled and said,” I need to get back to the real world.” Kyle replied,” I hope you don’t take offence when I tell you that I don’t think I am ready to tell my roommate everything about you.” I smiled and said,” I am not going to tell most of my friends about you either.” We both gave each other knowing looks.
I got up and tracked down my clothes. Strangely enough I still had my shoes and socks on. Kyle helped me with my bra and I got dressed and used the little sink and mirror to clean up a little and apply my makeup. When I was done I once again looked the innocent if disheveled school girl. Kyle also dressed and his cock promptly sprang to attention when he saw me all dolled up again.
Nervously he asked,” Could I see you again?” Smiling I asked,” Are you asking me out on a date?” Stammering slightly he said,” Yes.” I replied,” Ok.” Grabbing a pencil and paper I wrote down my phone number. Kyle asked,” Do you have any other clothes? What I mean is…” I smiled and said,” Yes I can look like a real girl if I want to, I can pass as a girl completely.” Blushing Kyle replied,” That’s not what I meant, you look like a real girl now. What I meant is do you have anything more casual.” I responded,” How about a cute little denim skirt and a tight top? ” Then on a whim I said,” I know what you would like I could wear a cute little jumper and put my hair in pig tails.” Kyle blushed as he smiled and I knew I had got it right and he responded,” How about a dress or something casual so we could go to dinner and a movie without attracting too much attention.” Smiling I said,” I could do that.”
I went to the door and he said,” If you wait a moment I‘ll walk you to your car.” This time he wore some jeans and a tee shirt instead of the baseball uniform. I could still tell he was turned on by the school girl outfit by the bulge in his pants. At the door we kissed like lovers and then made our way out into the dorm. The way to the elevator was through the TV lounge and I was stared at and wolf whistled at by all twenty guys with a couple of way to go Kyle’s and a did you check her ID thrown in as Kyle protectively got between me and them. At the car we kissed again and I left with a promise that Kyle would call.
Kyle called me everyday that week and after our date on Friday we ended up dating exclusively for an exciting lust filled six months. It was surprisingly easy to fall into the roll of being someone’s girlfriend. He buy’s the drinks and opens the doors I look pretty and fetch beers. I meet him quite a few times at the door dressed as a school girl. We acted out many of his fantasies most of them involving outfits that would normally be worn by young girls. He never saw me as a guy except once in a bar with his friends but he did not recognize me and I didn’t approach him or say anything until latter. I meet his friends and no one knew I was anything other than a girl. In the end we drifted apart because we both wanted to date girls.