My first date with Karen. Who was born Ken.
Karen was beautiful. She was several years younger than me. She had a beautiful body. Her tits were amazing, and she always wore blouses or dresses showed a lot of cleavage. She was almost as tall as me.
We worked together at a real estate office. Karen was the receptionist, and I was a Realtor. I always flirted with her and she flirted back. I was surprised that no-one else seemed to be hitting on her. One day I decided to ask her on a date. She quickly said, “Sure, I would like that. You’re cute and I see you making a tent in your pants, when we flirt.” She had never before said anything that sexual, when we talked.
I found out about a party that Saturday night. I went to her and asked if she was available that night. “I would love it, Bruce. What time should I be ready?” I told her eight, and she gave me her address.
I picked her up at eight. She was really looking great. I held the car door open for her. She kissed me on the cheek and said, “My, My. You are such a gentleman.”
The party was about a 45-minute drive away. We chatted for a few minutes. Then Karen reached over and worked my cock out of my pants. I quickly hardened in her hand. Leaning over, she slid her lips down my shaft. “You have a really nice cock.” Karen bobbed up and down till I couldn’t hold out anymore and blew a load in her mouth. My orgasm affected me so strongly that I almost drove off the road. She swallowed every drop and said, “That was a lot of yummy cum. I’m glad I didn’t spill any, I didn’t want to get my nice dress messed up.”
We got to the party. I only knew a couple people there. None of them were from our work. I got us each a drink. “Let’s dance, Bruce.” With her three-inch heels, she was slightly taller than me. We danced three dances. The last one was a slow dance. She pressed her tits against my chest, and I gave her butt a squeeze and told her that I really liked her ass. When I did, she made a happy noise and thanked me.
After the dance, we were standing in the corner. Karen put her arms around my neck and kissed me hard. Her tongue went deep in my mouth. I returned the kiss, just as aggressively returned the kiss. I slid one hand up, from her waist to one of her breasts. “Damn, you have such firm tits.” Nancy giggled.
“Let’s get out of here. Let’s go to my apartment.” She gave my package a squeeze. I knew she was in the mood to fuck.
When we entered her place, she kicked off her shoes and shared another long sexual kiss. I also kissed neck and she moaned. Then she backed away. She reached under her dress and tossed away what looked like a strap. With a big smile, Karen lifted her dress. Out sprung a half hard cock, as big as mine.
She saw at the shocked look on my face. “Oh God, you didn’t know? I thought everybody knew. I’m a tranny.”
I stammered, “Your tits, and ….? No, I didn’t know. I should leave.”
“I bought my tits. Don’t you still like them?” She and stood there in front of me. “You are saying you should leave, but you’re getting hard. Your cock ….”
“Yes, I like being both a guy and a girl, so I left my guy parts alone, but I bought these girls.” She put her hands under them and bounced them up and down, then she pulled her dress fully off. He/she she was now fully erect. “I have two holes for you to fuck. I already sucked your nice cock and swallowed your cum. Didn’t you enjoy that?”
“Yes. It was great, but I thought you were a girl.”
“You have always known me as a girl. I like my pronouns to be she and her. Do you want to stay or go?” When I did not run to the door, Karen stepped forward and started unbuckling my pants. When they fell to the floor, Karen put her hand around my shaft and started stroking it. I wasn’t sure I wanted it to, but it was now rapidly hardening.
She dropped to her knees and took me in her mouth, for a second time. After getting me fully hard, she could tell that I was going to stay. Karen took me by the hand and lead me to the bed. It was a strange sight to see her tits hanging down under her chest, and at the same time see a cock and balls hanging down between her legs. I couldn’t keep from occasionally thinking of Karen in terms of he and him.
Karen reached on the nightstand, picked up a tube of lube, put some on two fingers and rubbed it around, and in, her asshole. “Fuck me, Bruce. Fuck me hard and deep with that nice big, hard cock.”
I had dated a couple biological females who liked anal sex, and I knew they both they, and I, enjoyed it. Their asses were tighter than their cunts, which was nice. Karen had learned to relax her anal ring mussels. Because of that and the lube, I slid in without much effort. It was nice and tight inside. After a couple minutes, I stopped thinking about how I was fucking a man’s ass. Now it was just a very sexy asshole for me to fuck. In a husky but feminine voice, Karen kept encouraging me to fuck her hard and fast, and to come in her.
I reached the point of no return. My cock swelled and I felt squirt after squirt of my cum, pushing down my cock shaft and into Karen’s ass. Karen squealed with delight. I pulled out and watched my cum drain out of her gapped asshole and down onto her balls. She spun around and sucked my slimy cock clean as it softened. Then she came up and kissed me. After a couple seconds, I started returning the kiss.
We called it a night and I was about to leave. I said to Karen, “I don’t know how to say this, but because everyone at the office knows you are trans, I want to keep things between us like they were before tonight when we are in the office.”
“Don’t worry. I understand and am OK with it. Are you going to want to be with me again?”
“I have to think about it. I still think you are a beautiful and sexy person.”
A couple days later, at the office, when no-one was around, I went to Karen, “Weekend after next I have a timeshare condo at the lake reserved for three nights. Would you like to go with me?”
Karen smiled and said, “I would love to.”
What I didn’t know then, was that Karen was planning to spend part of the weekend reversing the roles and getting me to let him fuck my ass and mouth with his/her male parts.
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724. PO469. If you want to see a full list of my other stories, click on my username link at the top of this story. Any photos with my stories are of people who are 18 or older. They were consensually taken and come from my friends or from a website that states that its purpose is sharing adult photos and gifs. Photo credit and thanks to imagefap.com. If you claim copyright to any of these, and want it removed or credited, let me know.
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