REGINA

I am Regina. I am a Transvestite, and have been dressing for the past twenty odd years. I thought I would tell you all how I got started in my world of cross-dressing and TV sex. It is a life I have come to love, and if I could change it I would not.

I started dressing when I was nine years old at least that is my first real memory of dressing. My cousin, a girl, would dress me up to play house. She always told me how pretty I looked, and that I should al- ways dress as a girl. She would dress me in her things, and we would have a great time.

As we grew older we came to realize that me dressing as a girl was not acceptable to most people, and we had to hide our fun. She would often dress me up in my teenage years, and we have would sex as two girls. She would take me orally, and then put the cum in my mouth with her tongue. I really liked the taste of cum.

When her parents were not at home for a while she would fix me up so pretty, and we would go for walks in the park, or things like that. We always had boys following us, but we politely told them no. Sharon, my cousin, told me I ought to try sex with a boy sometime. I told her I did want to try it, but was afraid of getting beat up. She said that she would arrange it some time with someone she knew who would be very nice. I laughed, and I thought she was joking. She just smiled.

She never mentioned it again, and I thought she was only kidding with me. Until one day in October she told me she was having a Halloween Party, and was inviting a very special boy for me. I did not know what to say, but I was definitely interested. She said his name was Terry. He was a closet Bisexual, and had told her of boys who dress like girls. He said that he would love to meet one some time. I asked her if she told him of me, and she said no. I was to be a surprise for him.

Sharon's parents were gone for the weekend, and she started getting me ready early in the afternoon. She drew me a hot bubble bath, and added some scented oil to it. I felt so feminine as I slid beneath the bubbles, and started to bath in the scented water. Sharon came in with a razor, and told me stand up, so she could help me shave. She applied lather to my legs first, and shaved them clean. Then she had me turn around, and lathered my rear saying that a smooth ass was important to a sexy look. I did nothing to disagree with her as she seemed to know what she was doing.

Soon I was smooth from chin to toe, and quite excited from the feeling.

Sharon took care of me with a quick blow-job, depositing some of my own cum back in my mouth. I smiled at her, and thanked her for helping me out. I got out of the tub, dried off, and pulled on a satin dressing gown. Sharon told me to come to her room for my makeup and clothes.

As I walked in I was stunned by what she had laid out for me to wear. There on the bed laid some of the sexiest clothes I had ever seen let alone put on. She had me remove the gown, and started by handing me a pair of sexy black lace panties. I pulled the up my legs, and tucked my cock and balls well back between my legs.

Then she gave me a black corset to put on. It was very tight. Sharon laced it up the back, and pulled it in even tighter. She got a tape, and measured my waist. It was twenty-four inches. I could not believe it. It was very tight around my chest, and squeezed my breasts inward, so that they nearly filled the cups naturally. She added some padding, and when she was done it looked like I had real tits.

Next came a black garter-belt, and a pair of the sexiest black stockings I had ever seen. I put them on, and Sharon made sure the seams were straight.

She then handed me the skirt I was to wear. It was a short black leather mini, and I mean it was short! I put it on, and it barely covered the tops of my stockings. When I sat down it exposed me nearly to my crotch! Sharon smiled at me, and said that I should attract a lot of attention at the party.

Last I put on the red sweater Sharon had for me. It had a very deep v-neck, and showed my fake cleavage nicely. I looked at myself in the mirror, and was very happy with what I saw. Sharon had me put the gown back on so she could put on my makeup without messing up my outfit.

She started with a dark beige foundation, smoothing it out, and then began applying the eye makeup. WOW! Was it ever sexy! She accented my eyes with dark purple shadow, black liner, and mascara. She did my lips and nails in high gloss red.

Next she put a blond curly wig on me, and pulled it into place after she combed it out, surrouning my face in curls that fell to my shoulders. I put on a pair of red four inch heeled pumps, and stood up to look in the mirror. I looked stunning! I was a girl that any guy would cum in his pants over.

Sharon sat back in her chair, pulled down her panties, and started fingering herself. She was obviously turned on by all this. I walked over, and inserted one of my painted fingers into her. I gave her a kiss, and thanked her for what she had done for me. I sat back, and watched her ready herself for the party. She put on an equally sexy outfit, except her's was a dress, and not quite as short as mine.

The party was to start at seven o'clock, and people started to arrive early. Sharon introduced me as Regina, her cousin from New York City. The guys were really eyeing me up, and their girlfriends were really jealous of what they saw. I sat there as coyly as possible with my legs and crotch exposed as they were.

Sharon pointed out Terry to me. He was one of the guys who was constantly staring at my legs. I made eye contact with him, and smiled. He smiled back, and blushed a little. Sharon motioned for him to come over, and introduced us. I almost died when she told him that I was the sexy Transvestite she had promised him. His eyes lit up when he heard that, and he said he was glad I was not a girl because he really liked the way I looked, but he was not comfortable around girls.

He then asked me to dance. I got up to dance with him. Every guy in the place watched as we walked to the dance floor, and Terry took me in his arms.

As we danced, he was breathing in my ear, and I felt so feminine that I laid my head on his shoulder. He was continually telling me how great I looked, rubbing my back, and moving his hands to my ass. I did nothing to stop him.

As he rubbed my ass I felt the hem of my short skirt raising up. I am sure that every one there got a good peek at my pretty panties from the looks I was getting.

At the end of the song he pulled me to him, and gave me a little kiss. It felt like an electric shock went through me. I had never been kissed by a boy before, and felt like I was going to melt. Terry obviously sensed my condition, and held me tight, kissing me again, this time with much more passion. His tongue forced its way into my mouth, and for the first time I was getting kissed like I had always fantasized.

We walked over to a big overstuffed chair, and Terry sat down, pulling me onto his lap. I could feel his hard cock pushing against my rear, and was really getting turned on. Sitting there it was hard to keep my stocking tops covered, and was constantly trying to pull my skirt down to cover them. Terry told me not to bother because it turned him on immensely to know that all eyes were on me. I kind of enjoyed too!

Soon Terry suggested that we go into town for a soda at the malt shop. I asked him if he was sure, and he said he would be proud to be seen with me. I got up, and Terry put his hand under my skirt, rubbing my ass a for a second. I jumped, and he laughed, giving me a kiss. told Sharon that we were leaving. She giggled, and said that I should be careful not to get pregnant.

I got in the car, and slid over next to Terry. My skirt was bunched up around my waist, but Terry said to leave it that way, so I did.

As we drove to town he was rubbing my legs, telling me how great I looked, and how much he liked being with me. I was getting so turned on I could not stand it. I reached over, and put my hand on his crotch. I felt his cock jump when I touched it. I gently rubbed his cock, and laid my head on his shoulders until we arrived at the malt shop.

When we walked in, every eye in the place was on me. I felt like a model on a runway. Terry took my hand, and walked me to a booth in the back. Then he went to get us something to drink. He came back with two large glasses of cola. He reached into his coat, pulled out a small flask, and added some of the contents to my drink. He said it was rum, and that it would make me feel more relaxed.

I took a drink of my cola, and the warm feeling of the rum, and the movement of Terry's hand on my leg made me feel great. I finished my drink, and moved even closer to Terry. He took me in his arms, gave me a kiss, and said we should leave before it got too late.

Back in the car, I sat next to him, and started to rub his crotch
again. By the look in his face, and the hardness of his cock, I knew I was doing the right moves. We went to his house, and stopped in front.

He said that his parents were going to be out very late, and that we would have some time alone before he took me back to my cousin's.

As soon as we closed the door he took me to him, and kissed me passionately. I melted as I felt his cock pressing against me. I kissed him back as hard as I could, and reached down to his cock again. It was so hard, and I could feel the heat through his pants.

Terry looked me in the eyes as he lowered his zipper, and pulled out his cock. I looked down at it, and took it in my hand. He asked me if I had ever touched a man's cock before, and I told him only in my dreams. I could feel him pressing down on my shoulders, and I knew what he wanted me to do. I got down on my knees, and started to stroke his beautiful cock.

He pulled my head toward his crotch, and I opened my mouth to receive his tool. I kissed the tip, and then slowly took it into my mouth. I had always dreamed of doing this, and it was better than I had ever imagined. He pushed his cock into my throat, and it caused me to gag a little. He apologized, and told me to do it at my own pace. I stared to suck him off.

I could feel his cock get even bigger in my mouth. I was sucking likemad now, and Terry was moaning, telling me how good I was doing. SoonI felt him tense up, and grab the back of my head, pulling it down hard on his cock. He stared spurting cum into my throat, and I was swallowing as fast I could. Some of his juice leaked out of my mouth, and was running down my chin. Terry scooped it up, held my head back, and poured it into my mouth. I had never felt this way before in all my life, and I knew I had to have more.

He pulled me up to him, and kissed me hard on the lips, sucking some of his own cum into his mouth. He smiled at me, picked me up, and carried me to the sofa. He laid me down, and started to slowly and sensuously undress me. I was stroking his cock the whole time.

When he got he down to my bra and panties he stopped, and told me he wanted to leave them on to preserve the illusion. I said I preferred it that way too. He rolled me over, and began to massage my shoulders and back.

Soon he was rubbing my ass, and sliding his fingers up and down the crack. I was laying there playing with his dick. It got hard, so I started to suck him off again. Terry worked some lube into my rear, and inserted a finger. Oh, what a feeling! It hurt a little, but I just continued blowing my stud's cock. He eventually got his middle finger all the way up in me, and was massaging my prostate when he started to cum again. I was cumming too, and spurting she-male juice all over the sofa.

He came in my mouth, and pulled my head down hard on his cock. He then rolled me over, and licked all my cum off my belly as I licked him clean. He went to the kitchen, and came out with two more sodas.

After that, we lay there in each other's arms for a while. Then I
started to get dressed, and he went to get something to clean the sofa.

We left his place, and he drove me back to my cousin's house. He kissed me goodbye at the door, and left. I could see my cousin at the wondow, watching us kissing.

I went inside, and Sharon asked me if I had fun. Then she said I looked like a satisfied girl, but I assured her I was not. We changed into our nighties, and went to bed. When I told her all about my night out, she got so hot that we ended up in a beautiful Sixty-Nine position, and she sucked my "clit" until I came.

After that night I have been hooked on guys, and thoroughly enjoy giving a man a blow-job. I have been dressing as a girl as often as I can since that wonderful night with Terry, and he and I still see each other once in a while. Eventually, he screwed my rear, and filled me up with his cum, but that is another story.

wish my first time was like that