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Robert and I have sex for the first time.
Robert asked me out to a new year's party on Sunday night. When I say “asked” I mean he said I'm going with him and make sure I'm ready.
Robert is a guy I meet on Craigslist a couple weeks ago. He's 6’3” 198 lbs with blue eyes and brown hair. He's a personal trainer and does not use any drugs. He's 31 years old. He's quite successful and owns his own gym.
I'm Lisa, a trans woman. I completed my transition almost three years ago now. I'm 34 years old weigh 134 lbs. I'm 5’7” tall with a 36-25-37 figure I'm very proud of. I have blue green eyes and long natural red hair. The only surgery's I've ever had was a Tracheal shave and SRS surgery to get rid of my little cock, All the rest was through HRT, testosterone blockers and hard work.

I bought a new outfit just for the party. I'm pretty sluty when I want to be so.
I got a matching bright red lace push-up bra with white, yellow and blue flowers in the lace around the top of the low cut, pantie and garderbelt set. With shiny silk stockings. 7 inch bright red stiletto high heels with black bottoms. And the shortest low cut red mini dress I could find.
The day of the party I got up and felt extra sexy so I put a 4 inch jeweled butplug in my ass and a set of ben wa balls in my pussy. I turned them on the lowest setting. I could just barely feel them. I went and got a manicure and had my hair done, I showered, shaved my entire body. When I was finished dressing and my make-up and hair looked perfect, I was set for a night Robert would not forget, I hoped.
Robert called to tell me he has a flat tire and could I drive myself to the party. I asked him if I should take a cab instead as I'm sure we both might have a few drinks. Good idea, I'll see you soon he said. I called a friend who is a cabby knowing all the cabs would be busy as hell. Anthony told me he was driving by my place in a couple minutes and could I wait outside.
When he got there, he had a fair in the back seat already. I got in the front seat and agreed to split the fair.
Anthony could not keep his eyes off me which is weird because he knew me before the accident that eventually turn me into a woman.
I got to the party before Robert did so I went in and mingled. I didn't know very many people there so when I saw Robert staring at me I went up to him and grabbed his cock through his jeans and handed him the remote to the ben wa balls. His jaw was on the floor. He looked so cute. Hay baby I said to him as I looked up to his eyes. He was hardening up as I felt him up.
WOW was all he could say.
I've got plans for this tonight I told him as both hands were fondling his package. Poor guy looked like he was going to blow his load right there so I stopped and asked him for a drink.
Clearing his throat as he said in a few moments, I can't move right now ! I laughed and told him to relax, I'd get the drinks. Make mine a double please. Laughing at him I made sure to wiggle my ass as I made my way to the bar.
I was making my way back to our table and wondering when he would figure out what the remote was for when I felt the balls intensify. I almost dropped our drinks. I looked up to see the biggest smile I've ever seen on Roberts face.
Well I see you figured out what the remote is for !
I had no idea you were into this sort of thing he said.
I handed him his drink saying hunny, you have no idea what you're in for tonight do ya.
He just smiled and sipped his drink.
We had a blast dancing and grinding each other until around 11:30, then I noticed a bunch of people went out to the street to watch the fireworks. As it turns out Robert is a partner in the business and as such we went up to the roof with a bunch of other people. There was a pool with a hot tub up there and it was all inside a glass dome.
We were all handed a towel as we entered.
I was so hot for him. I pushed him against the wall and kissed him hard. His hand found my dripping wet pussy right away. My hands quickly fished out his huge cock as he fished out the balls from my pussy. He spun me around so my back was against the wall and slipped his cock head in my pussy. My short mini dress pulled up out of the way. My G-string panties got pushed to the side. Only a couple inches of his cock entered me but wow he's big I thought. I looked around to see we had some watchers. This turned me on even more.
Robert was not rough, he was firm in his actions but he was not giving me all his cock so I pushed him back and he stumbled and fell to the mat on the ground. I moved quickly to straddle him. I grabbed him and lowered myself rather quickly on his meat. This was a mistake as I suddenly realized he's a lot bigger than I thought. Intense pain ripped through my body. I froze in place and screaming out OH FUCK !!
He tried to move but I wouldn't let him.
Nerve endings all over my body were firing off all at once. At some point I realized I was almost all the way down to his balls. Pain slowly subsided and all I could think of was pleasure. I slowly rose up a couple inches and then slid back down again. Robert had a very worried look on his face so I guided his hands to my tits. I rode him for a few minutes then he slowly starting to raise up to meet me halfway. Before long I could feel his pubes on my very full pussy. He was giving me very long deep strokes and I forgot all about the other people watching.
I looked him in the eye and grunted to him to fill my cunt with cum at midnight. Sweat pouring off both of us, he just smiled. Robert fished my tits out and played with them as I heard everyone start the countdown. 10,9,8,7,6, I road Roberts cock even harder and faster as the countdown continued. 5,4,3,2, slamming my well used pussy down with every thrust he was giving me. He reached so far inside me I didn't care anymore, 1, HAPPY NEW YEAR. And Robert exploded in me so hard, I came instantly with him, it was so intense, nothing else mattered, my pussy contracted on his cock, milking him of his cum. it was like the two of us were the only two people on the planet. Robert grunted hard, I could hear myself screaming as he held his cock deep in my quivering pussy, I felt every spurt of his hot delicious cum hit my insides. I struggled to stay conscious as my vision started to fade away. I woke up a short while later, we both lay there quivering and shaking as if we had severe frostbite, We must have laid there at least 10 minutes while we both recovered. Roberts hot cock finally slipped out of my pussy along with a sizable amount of our mixed cum. I got up and looked around to see about 40 people staring at us. Everyone clapping and cheering. I just smiled and pulled my mini dress off over my head, I walked up to the pool,my legs week and my pussy throbbing as cum flooded out of my cunt and covered the insides of me thighs and jumped in. Most of the other people then stripped and jumped in to. Robert was still just laying there by the door with his flaccid cock sitting in a pool of cum.
A short while went by and Robert was still just laying there so I got out of the pool and went to him. I got on my hands and knees, I licked at his limp sizable cock. He was out cold. I continued to clean him up when I felt a set of hands on my hips. Roberts cock started to grow ever so slightly as he slept. I felt my butplug being pulled out. I didn't look to see who it was behind me. He pulled me back away from Roberts cock. He pushed my knees apart, he rubbed his cock at my wet pussy, I pulled away as I said no. That's Roberts only. He then he slid into my ass. Even though he was in my ass I could feel it in my pussy to. He fucked me easy and slow at first.
A young woman slid under my head and pushed her cunt to my face. I grabbed her hips and buried my tongue in her pussy. She's so sweet.
He started to pound me harder and harder as I lapped at the cunt in front of me. She told me to fist her so I slid four fingers in her and wiggled them, then I slowly slid my thumb in. I held my hand there as best I could as I was still taking a pounding. I pushed my fist in to my wrist. She cooed as I went deeper. I pulled my fist out part of the way. That's when I felt my ass getting filled with cum. I pushed my fist in half way up my forearm.
He pulled out of my ass and almost immediately after I felt hands on my hips again. His cock slipped in my ass easily. He had a slim but long cock. I pushed my fist in further and further until I was in all the way to my elbow. She squealed in pleasure. The guy in my ass cummed quickly and left.
Another guy stepped up to the girl I was fisting and put his dick in her mouth. She was a noisy cocksucker with loud slurps and choking sounds. This turned me on a bit. I continued to fist her hard as she sucked him.
Hands again were on my hips. This time the guy behind me wanted my pussy. I slid forward and said no as I looked back to see Robert with a raging hard-on.
I smiled and said hey stud. He slipped in all the way to the hilt. OH FUCK is he big. With nice easy slow but deep strokes, Robert made love to me. His balls slapping at my pussy as he slid in deep with each stroke.
Cum oozes out of my ass and coated Roberts long thick veiny cock.
I pulled my fist out and buried my face in her sopping wet pussy. Robert kept his pace going.
My tits suddenly fell free as Robert unhooked my bra. Next I felt something being pushed in my ass. Then a second thing was pushed in. The guy getting a blowjob cummed all over the girls face. I looked up to see her. What a sticky mess. She was flipped over on her back and her head was directly under my face. I licked at the cum on her face as another guy slid his dick in her cunt she squealed and cooed.
Robert really knew how to play the pussy. Even though he never picked up his pace, I started to cum. He just kept going. Suddenly I felt the ben wa balls in my ass. The intense vibration pushed me over the edge. Robert pushed in deep and with short jabbing strokes he fucked the orgasm out of me. I screamed out loud OH MY FUCK, DON'T STOP, DON'T STOP, PLEEEAASSEEE DDOOONNTT STTOOop. God please. I collapsed on the woman's chest, gasping for air. Robert still making love to me. My pussy felt so tight, I know it sounds wrong but after I cumed my cunt actually felt tighter.
I pushed myself up off the woman under me. She slid over a bit as she was getting fucked hard.
I felt Robert pulling at my hair. He was pulling my head up to the cock waiting for my mouth. I opened my mouth and a cock pushed in. I couldn't move my head as Robert pulled my hair but pushed down at my back. The guy started to push his cock further and further into my throat. I relaxed and let him in. He fucked my throat hard and deep. He was slim but long, just like the guy that filled my ass. He held my head steady as he slammed his hard cock in and out. I choked and gagged on him. I felt like the biggest slut in the world as I heard the same sounds coming from me as I heard from the young woman. Cum finally filled my throat and my pussy again.
Exhausted we made our way to the the shower by the hot tub. We cleaned each other up and then we started to look for my clothes. Here's your bra my dear, Robert handed it to me but my dress was nowhere to be found. I followed Robert to an office where he handed me a trench coat. I kissed him to say thank you then we made our way downstairs. The bar was packed, people dancing and partying all over. We found out way out to a car and Robert drove me back to my apartment building and got out to open the door for me. The doorman opened the doors as Robert kissed me goodnight. After we broke our kiss I took the trench coat off and handed it to him, then walked right past the doorman to the elevator saying thank you.
Your welcome mame was all i heard.

Please give me feedback good or bad. I'm trying to see if I can be a writer. I know I need to work at it.
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