Destiny Fulfilled

I had secretly cross-dressed since I was 6 or 7 years old. The compulsion never goes away and had stayed with me throughout my life. My marriage eventually broke up 5 years ago. Not because of sexual issues but because we wanted different things from life. It was not long before I started a new relationship with another beautiful woman. The sex was great however the desire to cross-dress remains strong. Wearing female attire was not enough. I wanted to discover whether I could be attractive to a man.

Having collected together a small wardrobe of female clothes I planned to visit a nearby sex club that once a month holds a night for cross-dressers and their admirers.

Concluding that less was more I prepared for my evening out. Wearing white nylon and lace panties under smoky black tights I put on slim-line jeans and black patent medium heel shoes. I tucked a short wine colored swing dress into the top of the jeans, put on a string pearl necklace and a shoulder length brown wig. Applying lip stick and eye shadow I looked at myself in the floor length mirror. Not bad!

Into my newly acquired patent leather handbag I put in a white slip, spare panties and tights, make-up, a brush, lube and condoms. With heart racing it was time to go.

An hour later I drew up at the club and found a space in the nearby car park.

So this was it: out of the closet for the first time in my life.

Having paid the entrance fee and obtained club membership. A lady, Lesley, offered to show me round. We were about to set off when a man came across and suggested to Lesley that he would be happy to take over. With a knowing smile she agreed. He introduced himself as Simon. I told him my alter-ego name of Jessica.

As we walked through the busy public area of the club I learned that ne was a TV admirer and a frequent visitor to the club. On the right we came to a room with showers and lockers. He asked whether I wanted to change. I found an empty locker and took off my jeans. In a nearby mirror I smoothed out my dress and adjusted my tights. I saw through the bodice of the dress that my nipples were standing proud. Perhaps I should have worn a bra.

Exiting the locker room Simon was patiently waiting. I felt his eyes run over me. He smiled and complimented me on how nice I looked.

We continued the tour of the club passing a crowded dance floor.

A flight of stairs down took us to an area that had playrooms. Both private and public. A couple were on a double bed. "She" on all fours while he was actively engaged in penetration.

With others we watched. I felt Simon's hand slip into mine. We looked at each other. He came closer and whispered "you are a lovely lady". We kissed. I felt his tongue in my mouth. Underneath my dress his hand caressed the back of my leg and stroked my buttocks. Standing close to me I felt something hard push against me.

I asked whether we could see a private playroom. Passing the couple on the bed we continued along the corridor and entered a playroom. Simon locked the door and switched on the light. He drew me to him and putting my arms around his neck we passionately kissed. He guided me towards a double bed and began taking off his shirt. I put my bag down and my fingers unbuttoned his trouser waist band and I eagerly explored inside. Here was any girl's desire: 8 inches of erect penis wet with precum. Removing his trousers Simon lay back. Having taken off my dress he gently played with my nipples. I took his member into my mouth. My tongue danced back and forth enjoying the salty taste of the pre-cum. More massage and without warning the moment of ejaculation arrived. White sticky semen covered my mouth and Simon's stomach.

Licking my lips I removed my shoes, tights and panties. Sitting astride Simon I leaned forward and nibbling his ear I whispered whether he would like to fuck me. He smiled. Nervously I confided that this would be my first time. He told me not to worry and relax. I felt his middle finger covered in cum push deep into me. Then two fingers. From my bag I took out lube and applying it to three fingers he pushed deep inside me. He caressed my breasts kissing my nipples. His penis was once again standing proud.

Placing a pillow on the middle of the bed I covered it with a towel. Lying across the bed with my buttocks raised by the pillow I opened wide my legs. Simon stood between them and reassuring me promised that he would be gentle. His penis was covered with the lube.

I felt the helmet of the penis gently enter me. He applied pressure and I felt it slide further into me. More pressure and his balls were now hard against me. I thought my bottom was going to explode. He slowly rocked back and forth. His penis tight in my hole it was hurting, I bit my lip. The rocking became faster and soon he was thrusting. The pain lessened. I closed my eyes enjoying the feeling of deep penetration and feeling joy at having at last lost my virginity.

I felt his penis pulse. He kissed me and exhausted we both lay on the bed in each others arms. He withdrew his penis. Warm semen trickled down my leg.

Time to get up we showered together and dressed.