Our Newest Same-Sex winner is:
I wanted him to have me completely and totally. I couldn't believe I was feeling like this as I sat in the passenger seat of his car. His cock felt so large in my hands. I.... well I guess I'd better explain who “I” am.
My name is Robin, I'm transgendered. I guess I've known it since was six years old. I used to pray each night as a small boy that when I woke up I would be a girl. Around the age of eleven or twelve I used to sneak into my sisters room when no one was home and dress up in her clothes and an old wig she had laying around. I was very small for my gender and age. I also had very girlish features. Just having the clothes and wig on made a tremendous transformation in the mirror before me and also got me very excited, although I didn't know what masturbation was yet or how to relieve the sexy feeling I got by dressing up as a girl. By the time I was sixteen I was sneaking into my mom's clothes and hooked for life.
After graduating from high school I put dressing up behind me for a while as I never had a chance to be alone in college and the army. I also didn't have access to a easy supply of women's clothes. But any time I was home for weekends and by myself at the house I would start going through the closets looking for stuff to try on.
It wasn't until after my divorce from my wife that I discovered by reading magazines and seeing it on talk shows that there were other people just like me who had the exact same feelings. This finding out that that I was not alone was the best thing that could have ever happened to me. The door to exploring my female side had finally been cracked open.
I started getting some clothes of my own together and played dress up anytime I was alone at the house. One time while dressed, some girls I knew stopped by to see me. I had left the door to the house unlocked and they had just walked right in. I hurriedly removed my clothes and slipped on a T-shirt and jeans. Casually I walked out of the bedroom and started chatting with them. I thought I had pulled it off till one of them asked me why was I wearing panty hose. I looked down and blushed as I realized that I had forgotten to put some socks on to cover up the hose I had left on from being in such a hurry to change.
I thought about coming up with some kind of excuse and they even provided some plausible ones for me but after some thought about it I decided that telling the truth was the best thing to do. So I took a deep breath and told them to wait just a bit. I went back to the bedroom and dressed again and walked out. I expected them to burst out laughing at me and start calling me a sissy or get disgusted and leave and tell the whole small town I lived in what a pervert I was.
But much to my surprise they thought what I was doing was very cool. They took me back to the bedroom and started fixing my hair and showing my how to apply makeup. The next day they showed up with shopping bags full of makeup and clothes that were extras or slightly worn. The following week was heaven as my two new girlfriends and me shopped and played dress up almost every night.
After a couple of weeks had passed I felt confident to actually go to a gay bar that also had a drag show. It was about 90 miles from home. My town and county was dry and boring. This meant I had to drive all the way there and back in drag. Just getting out the door that first time while dressed up was terrifying.
I soon arrived at the bar and almost immediately some drag queens felt sorry for me and took me under their wing and by the time I walked out I had gotten a full transformation by people who knew the secrets of making a boy into a girl. I walked out of there feeling and looking like a million bucks and it sure was depressing to finally have to take the make up off late Sunday evening. I hadn't even slept after getting home Saturday night, I was so happy with how I looked.
Going to the drag bars in nearby towns became the normal weekend routine for me when I could get away. I even would get a hotel sometimes and spend the weekend and go shopping at the mall while dressed. I would even go grocery shopping in my home town and go buy makeup and clothes at the local discount store. You could say I wasn't afraid to walk out my door anymore.
About this time I decided to move away from the small town I was living in and head to a larger city where I could meet other people who felt as I did and dress up as often as possible. One of the more fun things I liked to do was to go to the adult video stores and just browse while dressed in very tight short skirts. I loved bending over a lot to look at stuff on the lower shelves while near guys just to get them excited. Almost every time one guy would casually follow me out and try to pick me up. I was pretty picky and the clientele at these places usually left a lot to be desired but it was a great ego boost to be chased after.
I also hung out at the gay bars downtown and met a lot of really nice people. I had been hanging at this one bar downtown and dancing with friends. They had all left for the evening but I just hung around for a bit, not feeling like heading home just yet. Later I was sure was glad I had.
I was walking across the balcony when I saw him. He saw me as well and asked me to dance. He was tall, real tall. I'm six foot tall myself and he made me feel like a giggling schoolgirl. I accepted his invitation and it was heaven being in his arms during a slow dance. He couldn't stop telling me how cute I was. I know I was blushing. After our dance he led me outside to an enclosed patio. Hardly anyone was around as it was getting pretty late. He walked me to a dark corner and pulled me to him. I wrapped my arms around him and put my head on his shoulders. I didn't realize he had unzipped his pants till he took my hand and guided it to his hard prick that pressed between us. It was huge, well formed and not even hard. I tried to fix the not hard part as I stroked it up and down. He ran his hands up and down my back and clutched my tight firm ass and squeezed it. I put my head near his ear and whispered, “Would you like to come home with me?”. He nodded and pulled me close to him. I kissed him and we turned to leave.
His car was close to the bar and he offered to give me a ride to mine which was a few blocks away. As his car pulled behind mine I couldn't get out of his car without actually seeing that wonderful prick that I had held in my hands but never set eyes on. I asked him to pull it out and let me suck on it a bit before we headed to my place. He eagerly agreed. It was truly the most beautiful cock I have ever had the pleasure of touching. It was almost 11 inches long and so big around that I wondered if I really could fit it in my tight ass or not. But for now all I wanted to do was to lick and suck on it and see how big it really got when hard. I bent over and wrapped my hands around it and slipped it between my lips. I licked and sucked as much of it as I could into my mouth and there was still a lot of it left over to stroke with my hands. I even had him slide his pants down so I could play with and such his balls as well. You should have heard him moan when I slipped his balls into my hot mouth and rolled them around gently while I kept stroking his now soaking wet cock.
By this time I was getting very excited myself. I also knew if I kept it up much longer he would cum and probably not want to follow me home after that. So reluctantly I got back up and let him try to slide that monster into his pants. I asked him if he was ready to follow me to my house. The look in his eyes was all the answer I needed.
In a short while we arrived at my apartment. In the parking lot I walked over to his car as he was getting out. We kissed and held each other close as we walked to my door. Once inside, I made him a drink and told him to make himself comfortable while I slipped into something more comfortable. As soon as I was in my bedroom off came the blouse, skirt, and panty hose. I pulled out my favorite black lace garter and matching bra and panties along with a pair of black lace top stockings. On top of that I put on a sheer black silk robe tied loosely at the waist. I checked myself in the mirror touching up my makeup and spraying some sexy hot perfume on those hot spots. I messed my hair into a slightly wild and teased look. I was ready.
I walked into the living room and posed like a model in a magazine. “Well gorgeous, How do I look?” I asked. He stared at me with total lust in his eyes and I swear I could hear his breathing deepen. Patting his hand beside him on the sofa was my invitation to have a seat beside him. I wasted no time. Snuggling up to him on the couch I felt his strong hand running from one end of my body to the other. My hands however only wanted to be in one place and we both knew where. His pants were already unzipped and I fished that hardening piece of man meat out of his trousers. I slowly stroked it till it became a heated iron bar in my hands. His tongue was trying to see how far it could get into my mouth. I felt my own small cock start to stir and realized just how turned on I was by this man. I had been with other men but they had never excited me this way. I loved to suck cocks and feel that hot wet cum shoot in my mouth, down my throat and sometimes even just splash all over my face. I also loved the feel of a man cumming in or on my ass. But I rarely ever got an erection myself from any of that. I would usually get off later to the thoughts of how much like a woman the experience had been or just by looking at myself in the mirror. Seeing the tiny hard and shaved cock surrounded by sexy women's clothes totally turned me on. Tonight however I was totally excited and turned on by this guy I was with.
I stood up from the sofa and while holding his hand, led him to my bedroom. As soon as we were close to the bed I turned and started peeling his clothes off. He untied my robe and let it fall to the ground. It joined the growing pile of clothes there. I jumped into the bed and he turned and sat down, his hard cock jutting from his lap. I immediately wrapped my red lipsticked lips around his shaft and began to suck like I had never sucked a cock before. His hands roamed all over my body causing it to tingle from one end to the other. My panties were bulging quite noticeably by now. He reached down and pulled them to one side. My aching cock sprang free. He started gently stroking my cock in time to my sucking his. I had never met a man before who even wanted to know I had a cock much less touch it. Most guys just a tranny to get them off but don't want to return the favor. They seem to think that as long as they don't touch or suck a cock they are still straight. It almost makes me laugh. Any guy who has a transvestite between his legs sucking his cock or slams his cock up the ass of a tranny is slightly crooked, even if he never touches a cock himself. But not this guy, he was making me feel so good.
I moved over on the bed and got into a sixty-nine position with him. He wrapped his lips around my cock and started sucking me. God, he was good. I knew I wouldn't be able to take much of that without cumming. I didn't want to cum before he did. I moistened one finger, reached around and started rubbing his ass. That was all it took. I felt his cock stiffen and he rammed it as far down my mouth as it would go. His sweet warm cum shot endlessly into my mouth. I kept swallowing but couldn't keep up with the flow. A couple of drops fell from my mouth onto his hard smooth stomach. I greedily licked them up. His orgasm was all I needed to send me over the edge as well.
It was my first orgasm with a guy. I had never felt one so good before. After I came back to earth he pulled me to him and kissed me mixing our cum together inside our mouths, while we stroked each others cocks in the afterglow of orgasm. I hoped he had more than one bullet in his gun and was soon rewarded with the sensation of his cock again swelling up to its magnificent erect size. I knelt down and kissed the head and then slipped a rubber over it. I got on my hands and knees and he didn't need any words from me to know what I wanted him to do. He got behind me and put his strong hands on my butt and pulled my cheeks apart. I pointed out the lube on the nightstand to him and he liberally applied it to both his cock and my ass.
He started by slowly working a finger at a time into my ass till he had three of them inside me. Then he slowly started fucking me with his fingers and stretching me out at the same time till I was nice and ready for his giant tool. I reached back between my legs and guided it to my waiting hole and slowly eased it inside me. It still was almost more than I could take just to get him in, but I slowly got used to him and he started sliding his cock further and further inside me till he was resting against my ass with all eleven inches inside me. We both moaned and I felt my cock begin to get hard again as well. He slowly eased his cock back out till just the head was in me and again slid fully into me.
At this point I said, “Go ahead and fuck me baby. Fuck me hard!” He didn't need any further urging and started plunging his cock in and out of my ass at a furious pace. I stroked my now hard cock as I was pounded in the ass by his. He then pulled out of my ass and flipped me over on my back, pulled my legs over his shoulders and rammed his cock back into my ass almost in one smooth movement. I never stopped stroking my little smoothly shaved cock and I could tell it was turning him on to see me do it. I felt his cock inside me get harder and knew he was on the verge of cumming again. I was almost there again myself.
“Cum on my cock!", I cried. He pulled out of my ass and ripped the condom off it. Stroking himself with his hand he started spurting cum not only on my cock but all over my chest as well. Jet after jet of hot white cum flew from his cock onto me and I loved it. My own cock started to add to the mix as well and with my free hand I was scooping up cum and licking it off my fingers. Meanwhile he was keeling down and licking up the cum that was all over my cock. I had never had such good sex with anyone before in my life. I went and got some towels and cleaned us both up.
He laid back on the bed and I curled up beside him, with my head on his chest, my legs wrapped around him, and my hand wrapped lovingly around his cock. He was soon asleep and I was drifting there myself with thoughts in my head of becoming a woman and marrying this hot stud beside me.
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