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I met Jonathan on  Ashley Madison dating app.   He was tall, slim and ruggedly good looking, in his mid 30’s.  Jonathan was very well spok...

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Ts Party - Ashley Madison

I met Jonathan
on  Ashley Madison dating app.
He was tall, slim and ruggedly good looking, in his mid 30’s. 

Jonathan was very well spoken and had quite a posh accent, you could just tell he was very well educated, maybe even from Oxford or Cambridge and came from a high class family.

He was quite wealthy, a lonely man who lived on his own in a very well to do area of London.

At the time we met, he was drinking heavily partly due to a divorce he was right in the middle of.

He spoke of it very little, but I could see the strain at times etched on his handsome face.

We became good friends and I used to hangout at his home during weekends.

Sometimes we went out for lunch or dinner, sometimes the cinema or walking around at the local mall.

It took some time for him to really open up to me, to show me his real self. 

The more I spent time with him, the more he started to reveal his other side.

Through our time together, I got to know that he really loved transgender women; he had a real thing for them.

He said that he dated a trans girl for sometime and also had many trans friends who he invited to his house from time to time. He showed me some pictures of them, saved on his phone.
One day out of the blue I received a text from Jonathan asking me to accompany him to a transgender party.

I had never been to one before and was curious to say the least so I agreed to go with him.

This party was around an hour’s drive from his house, so at 10pm I arrived at his and we drove.

When we arrived, I was surprised to find an old fashioned scruffy looking building, I’m not really sure what I’d expected to find but this certainly wasn’t it!

I walked behind Jonathan as we entered the building, I really didn’t know what I’d find beyond the front door. Surprisingly despite the derelict outside it was very modern looking inside.

Within the place contained a wild and wonderful assortment of different people, standing just by the door of the living room were several very glamorous looking trans women. 

I tried not to stare at them for fear of appearing rude, and making someone angry in the process, but they were absolutely gorgeous.
As we approached they smiled at us and hugged Jonathan, he was friends with many of them and attended their parties often. They greeted each other warmly.

“Hello darling, how are you?” said one of the girls to Jonathan as they embraced.

“Ladies, let me introduce you to my friend, this is Amber….”

I stepped forward as a pretty young girl called Jackie grabbed me and kissed me passionately on both cheeks in what has to be described as the most incredible welcome I’d ever received! 

We all small talked for a while whilst propping ourselves up against various pieces of magnificent and expensive looking furniture.

We eventually moved over to the sofa to continue our cosy conversations, as we slowly got to know each other. 

It was such a nice chilled out vibe at this party and everybody was so friendly and relaxed, pretty soon I felt completely at ease.

I was offered drinks. The small coffee table in front of us was literally covered in just about every type of drink you could imagine! I was drawn to the big bottle of Malibu.

I sat back fully into the sofa with my glass of Malibu, as comfortable as I’ve ever felt. I was already starting to buzz!

Pretty soon there was a big group of us together chatting, laughing and drinking, it was so much fun! In the background, music was playing, subconsciously my body motions and actions started moving in time to the beat.

As we were talking, just to the end of the sofa was a girl called Amy, I couldn’t take my eyes off of her, she was so attractive. 

She looked just like a pristine Barbie doll with magnificent make up; as I watched her chatting to Jonathan I couldn’t believe how beautiful she was. 

She was also so graceful the way she carried herself, as she spoke her whole face lit up, what an amazing smile I thought to myself! 

Suddenly she looked up and noticed me staring at her, it was as if she could feel my eyes transfixed on her, like razor sharp laser beams penetrating through her. 

She walked over to me and smiled, “Hey, I’m Amy,” she said as she held out her hand in front of me, her nails were painted red and manicured to perfection.

“Amber” I answered as my hand met hers. She gently sat down next to me; we were so close to each other, as others on the sofa moved up and made room for her. 

She wore a yellow bikini, her boobs were bulging out deliciously from her bra, they were so big and perfectly shaped, I remember thinking that they looked so real and were definitely much better looking than mine!

“Your boobs are amazing” I said as I sat and admired them.

“Thank You” said Amy, as she looked down and touched them playfully with a smile.

She went on to tell me that she’d got them done in California the previous year by a renowned surgeon. She loved talking to me about her body. 

I complimented her many times and started to ask her more and more questions, I was fascinated by her. Not being able to contain myself any longer, I asked her, “Do you mind if I touch them?”

Amy smiled and said “Sweetie, of course you can!” She replied, moving her boobs closer to me. She removed one side of her bra to expose her whole breast, I looked at one of her bare nipples and touched it with my hand, I felt all around her boob moving and caressing my hand around, it felt so smooth and was incredible to touch. 

I felt much envy with how perfect they were to look at, especially right up close and personal!

As I touched her tenderly, our eyes met. I could see that she was enjoying it. She gave me a horny look as if she hadn’t been fulfilled and satisfied properly for a long time, my hand was still touching her body.

By this time I was so wasted that I had given up all reasonable thoughts and just went along with the flow. It certainly felt right to me in the moment.

I responded to the randy look she’d just given me. It made me so excited!

“Can I kiss you?” I asked.

With a cheeky smile she leaned in and planted a big wet kiss right on my lips. 

It felt so good as our mouths met, tongues touching until we both decided to go in deeper, tonguing the farthest reaches of each other’s mouths in circular motions as our lips smacked tightly together. 

It was one hell of a snog!

Suddenly Amy stopped and pulled away from me, she got up from the sofa and grabbed hold of my hand; I stood up and could immediately feel my head rushing as I got to my feet. Amy pointed to a nearby mattress that was lying vacant in the corner of the living room.

I glanced over at it and saw that it had nicely arranged pillows and white silk transparent curtains pulled to one side. Almost as if it had been waiting for someone to jump on and make good use of it! 

It looked so inviting.

Amy took me by the hand, and with a sexy smile of anticipation she walked me over to the mattress. She got on and pulled me by the hand to join her. 

We resumed our deep kissing on the mattress, only this time our hands were touching our bodies, exploring each other’s hot flesh to the fullest.


By now I could feel that Amy had a massive erect cock sticking out from her bikini bottoms. I touched it slowly whilst I was kissing her. 

Amy began to get more and more aroused and her next move was to try and remove my clothes, but I could feel all the eyes of the group burning into me as we played, watching us intently and with excitement from the sofa and all around the room.
It made me feel so self conscious in the moment and I stopped her from taking my clothes off. I already felt naked with all those eyes on me.

We continued to kiss and caress passionately, I couldn’t resist playing with her rock hard cock which was still standing to attention and waiting for orders! 

Suddenly she jumped on top of me, pinning my wrists playfully to the mattress.

“Take your pants off Amber” Amy asked. 

Despite feeling drunk I just hadn’t come prepared to have sex.

“I can’t, I’m sorry” I whispered to her gently. 

I could see right there and then just how much she really wanted me, which did feel nice to be desperately desired in this way.

Amy was so understanding, she smiled at me and released my wrists as she climbed back off me.

“It’s ok babe” She said as she gently stroked my face.

As I got up from the mattress, I looked over and saw Jonathan standing by the doorway holding a small glass of whiskey on the rocks; he’d been watching us all this time!

I tapped him on the shoulder as he smiled at me and handed over the glass of whiskey, placing it in my hand. “You had fun?” Jonathan asked as he put his arm around me. “Yes!” I nodded emphatically. We went back to sit on the sofa once more.

As I was very close to passing out, feeling dizzy high and largely at peace, I remember seeing Jonathan get on the mattress to join Amy as they began making out together.

I rested my head over the sofa and was gone! Lights out. 

The next thing I remember was Jonathan waking me, as I came to slowly in a heavy daze, it was time to leave. I looked around the room as I gathered myself and noticed that by now most people had left, including Amy. 

Saying our goodbyes we left and returned to his place, after falling asleep on the journey, I again crashed out straight away through exhaustion once we arrived back at Jonathan’s house!

The next afternoon when I eventually awoke, I sat up in bed and recounted my first time meeting with a trans girl and all the fun we had together!

Jonathan had this secretly hidden kinky side to him. There is another amazing story for me to tell you all about what happened at his place. I will reveal all to you another time.

Story by Amber

Share your story: stories@kinkyp.com 

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