My name is Cassandra Jenner, thirty years old and from London. I have always been open-minded to try and experience new things and people, especially when it came to sex. I’m very experienced in the bedroom. Bondage, lesbian sex, straight sex, I’m up for it. Sex relaxes me, and makes me happy.
When I was eighteen, I was very much alone as my parents never had time for me in their own drama. So I would learn for myself what sex was by watching porn on the internet. I wanted to see what all the fuss was about. I was shocked and excited. Every day after that, I would watch porn and masturbate until orgasm. And boy, it made my miserable existence happy and relaxed.
One thing I haven’t tried in my very active sex life is doing it with a trans-gender. It’s not that I don’t like the idea; it’s just that the opportunity to experience sex with a trannie never came around. I’d seen she-male porn, girls with dicks and balls, and that made me desire it. I wanted to have sex with a tranny.
I went to a drag queen club one night in uptown London to see what all the fuss was about. The club was packed but I managed to find a space at the bar. I ordered a martini. I wore a gold shimmery mini dress and had my long dark hair down, and gold heels to match. I thanked the bartender.
The stage lights dimmed and then a stage light came on and a beautiful blonde tranny came out onstage in a lilac-coloured sequinned dress and began dancing. The way she moved gracefully across the stage moved me as I was captivated by her. When she was under the spotlight now and again, I could see the outline of her dick in her dress. I sipped my martini.
The tranny finished her dance by doing the splits with her arms out like a ballerina.
Everyone got to their feet and applauded and so did I.
She curtsied and smiled widely. Her eyes travelled around the crowded club and rested on me. She winked and then went off stage.
An hour or so went by before the blonde tranny finished work and walked over to me in a pair of jeans and a white low-cut top at the bar.
“Hi, I’m Wilma,” she said in a feminine voice, which surprised me as, for a tranny, I thought she would have a deep voice.
“Cassandra,” I replied, shaking her right hand.
Wilma sat on the stool in front of me and touched my right thigh. “Well, it’s a pleasure meeting you, honey. Would you like a drink?”
“Sure,” I replied with a smile. My eyes lingered down to her huge chest and I felt my pussy getting wet. They widened when I noticed a bulge in her pants.
“See anything you like, honey?” she asked.
I blushed as I quickly turned away.
Wilma laughed and handed me a martini. “Well, to new friends,” she said.
I clicked my glass against hers and we drank. “To new friends,” I said with a smile.
An hour later, the club was closing up and Wilma and I were busy laughing and talking and flirting with one another.
“Let’s get out of here, sugar, and have some real fun,” she suggested.
“Sounds great,” I replied.
Wilma paid and we walked together out of the club.
It was raining heavily. I followed her to her car in the car park and we got in.
She and I turned to each other, feeling the lust and passion between us. We kissed passionately and I climbed onto her lap, feeling the bulge in her jeans.
I unbuttoned her jeans and unzipped them, releasing the beast from its cage. And she was huge. I looked up at Wilma with a smile. “Wow, you’re big!” I said.
Wilma laughed. “Enjoy, sweetie,” she replied. She gasped pleasurably as my lips went around the tip of her hard, pulsating cock and moved my mouth up and down the shaft. Her hands pushed gently down on my head.
I had given her a blowjob for five minutes before slipping off my knickers and then slipping her cock inside me.
We both gasped in pleasure and began to make love, moaning loudly. I bumped my head a few times on the roof of the car as it rocked from side to side beneath us as our lovemaking intensified.
Wilma and I changed position five minutes later in the doggy-style position and she inserted her cock inside my ass. I cried out loudly with pleasure as it intensified. My pussy was throbby and completely wet; it was gagging for her cock back inside it.
“Put it back in my pussy!” I cried.
Wilma laughed and teased my pussy with her right hand and my body quivered beneath her touch. She inserted two to three fingers inside my pussy.
“How much do you want my dick inside you, honey?” she asked.
“So much!” I shouted.
“Your pussy is so wet and moist.” She tasted my pussy juices with her finger. “Wow, so sweet-tasting.” Wilma bent down and put her face in between my butt cheeks as her tongue began twirling around my pussy.
“Oh, God! Fuck me now!”
Wilma laughed again and exchanged her tongue with her hard pulsating cock and balls and thrust herself deep inside me.
Our lovemaking was gentle then became increasingly faster and harder as we got into it. We were now in the backseat of the car now with more space to fuck. The car squealed and rocked harder and faster as Wilma’s balls banged against my thighs like sandbags whacking against a table.
“I’m cumming! I’m cumming!” I cried loudly. My body quivered uncontrollably beneath her as I orgasmed just as she did deep inside me.
Wilma and I looked at each other, breathlessly. Each of us smiled happily. I knew it was one experience I would never forget.
My first time with a tranny was awesome!