I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.
So after a lot of planning over several months, the day had finally come.
I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any woman would and off to the bedroom.
I sat on the edge of the bed. Dropped the towel and picked up my false breasts, a lovely C-cup size. I applied a little adhesive and they were soon attached to my chest the weight felt comforting. Next on was an emerald green satin bra and knicker set. I loved the way the satin felt on my skin. Then a waist clincher to help with my curves, after all I was middle aged.
I wanted to wear stockings but the dress I had chosen for the evening would have shown off the tops and I didn’t want to look trashy. So I slid the black sheer tights up my legs, the material against my legs sent thrills through my body. I adjusted myself in my knickers and put on a panty liner to deal with the excitement that was leaking from me.
I stepped into my 3inch high black suede knee high boots and zipped them up. Then into my dress a lovely forest green skater dress that came to above my knees.
I stood up and checked myself in the mirror and was very pleased with the reflection. The way the skirt flowed around my hips and legs.The glimpse of sheer tights on my thighs as the skirts swished as I moved. The way the top half was filled out by my breasts.
Now the complicated part. Over to the mirror on the table and time for make-up, I had been practicing over the months and felt I was reasonable good at apply everything.
After what felt like ages I had the smoky effect eyeshadow applied, eye liner done, eye brows done, foundation done, light blusher done and red lipstick on my concession to the femme fatale look I wished I could pull off. Next on went my wig a shoulder length auburn with blonde highlights and finally my French manicure false nails.
I went downstairs and sat on the sofa to give the nail glue a chance to dry an hour later I was the ready, I checked my watch 8.20pm, I finished my look a silver necklace three silver rings on my hands and silver bracelets. I picked up my handbag already filled with the essentials. My coat and car keys.
I stepped out the front door and went to the car. I got in the driving seat and smoothed my skirt It felt great and the way the seatbelt crossed over me falling between my breasts amazing. I pulled off the driveway and headed to my destination,
I had researched on the internet and found that Nottingham had lots of LGBT friendly bars that I could go to and it was only 50 minutes from where I lived. The drive was great. The feelings from every swish and rub and cling from the clothes just made me feel more feminine than I could have hoped.
My Sat-Nav got me there and to a car pack not far from the area I was heading for in no time. I locked the car and dropped the keys in my handbag. I googled the bar I had picked and got directions and headed off.
I came to my first group of people in the street, my heart was pounding with fear, expecting to hear “Perv,” and “Sicko,” or any other manner of insults. But nothing was said they barely gave me a second glance. With new found confidence I continued to the bar.
I got to the entrance and paused considering whether to turn around and go home. But admonished myself for even thinking of backing out and stepped through the door.
Once inside the bar did not go quiet and everyone did not look at me. It finally hit me nobody cared I was not born Jessica. I was just another human being on planet earth living my life.
I went to the bar and ordered a drink and I found a seat just enjoying the atmosphere and revelling in being there as I was. I watched the people. I noticed that every now and again someone would look in my direction but that was it.
I had been there about forty minutes and my drink was almost out when a woman came over, she extended her hand and said, “Hi Hun I’m Wendy me and the girls thought you looked lost and wondered if you would like to join us?”
I replied, “Jessica It’s my first time,” then added “here.”
“Thought so,” Wendy said with a chuckle. “Come over and join us, we’ll show you round.”
I picked up my handbag and coat and followed Wendy over to her friends. I ordered another drink and started chatting to the group. I learnt that Wendy was a crossdresser and so were a few of the group and the rest were born women. We discussed our looks and was so pleased with the comments that I looked passable as I had sensibly picked an outfit that was suitable for my age.
One of the group called Gemma bought me a cocktail and demanded I drink it, I looked at it and wasn’t sure about the cream on top and the milky colour but played alongmas I drank it down Gemma was giggling like a school girl. Its taste wasn’t too bad afterwards Gemma could barely contain herself and said
“Well Jessica that’s your first time swallowing a blow job,” those around started laughing and I laughed too.
That was the start of a game for them I was handed several cocktails and told to drink, by the last drink I had had a ‘Hard Dick’, ‘Red Headed Slut’, ‘Sex on my Face’, ‘Anus Burner’, ‘Suck, Bang, Blow’, ‘The Leg Spreader’ and “Slow Comfortable Screw Up against the Wall”. All a first for me.
When they suggested a club I agreed as I was having such a great time.
In the club I stuck to water as I didn’t want to be sick. But joined in with the dancing and conversation. In the club it was my first time going to the ladies and as per the girls code I went with Gemma and Wendy.
At around midnight some of the group’s boyfriends turned up and joined us. Gemma and her boyfriend got on the dance floor. Wendy introduced me to her boyfriend and suggested we should have a dance I was reluctant and took some persuading but joined Mitch for a dance. Another first. One dance later I returned Mitch to Wendy with a smile on my face having to admit it was fun.
I went to the bar and when I returned Wendy and Gemma introduced me to Mark. Wendy winked at me as she said, "It's Marks first time here as well we thought you two could compare notes on your firsts."
Mark invited me over to a seat and started talking. I realised he spoke for about 15minutes about himself and I inwardly chuckled as I realised this is what every woman experiences. While he spoke I noticed Wendy lead Mitch by the hand off to the toilets. He finally asked me a question and seemed to listen and we chatted.
He said, "Shall we dance?" I thought why not. A couple of dances later we sat back down and Mark got some drinks we chatted some more.
Suddenly he took my hand and pulled me to the dance floor. I wasn’t prepared for that but followed, just as we got four or five dances moves into the song the DJ cut in and said, “This song goes out to Hayley and Frank Congrats,” and on came a slow song.
I just stood there and didn’t know what to do. Mark decided for me as he stepped in and put his hands on my hips what else could I do my arms went to his shoulders and we shuffle danced to the song. As the song played Mark got closer and closer to me. I wasn’t sure about how I felt. By the end of the song Marks arms were around my waist and on the small of my back my arms were around his neck and my head on his shoulder.
However what I wasn’t prepared for the most was Marks leg which was between mine and my leg was between his and I could easily feel his erection on my hip. He led me back to our seat by my hand and we sat down. I excused myself and went to powder my nose.
I stood at the sink and looked in the mirror my thoughts confused. Suddenly, Gemma was next to me and asked if everything was ok. I told her what had happened on the dance floor and tried to explain how I felt.
Gemma asked, “Did you enjoy the dance?”
"Yes," I admitted.
“Did you want to walk away?”
"No," I replied.
“Did you come out tonight to be Jessica?”
"Yes, of course."
“Did you not think some might like Jessica?"
"No it hadn’t occurred to me."
“Can you say NO?”
"Yes, of course I can!"
Then with a clear matter of fact tone to her voice Gemma said just go with it and if you feel uncomfortable say “STOP,” now get back out there and let Mark know he has not pissed you off.
“Okay,” I said.
When I returned Mark was sitting there looking concerned and maybe a little scared. My heart went out to the poor guy. I sat down and started talking to Mark he looked relieved. Our conversation seemed to be getting more personal as we swapped life stories. He enjoyed the cocktail story.
"Can we have a dance?" he asked I nodded and he stood up. I offered him my hand and he beamed a smile as he took my hand we strutted our stuff on the dance floor and a couple of songs later another slow dance came on. Without hesitation I moved in and put my arms around Marks neck and my head on his shoulder. His arms were around my waist in a flash and our bodies closed the gap between us.
As we danced I could feel Mark pressing his groin against my hip and his thigh pressing against my groin. The results of this were obvious and soon it was his erection pressing against my hip and I could feel my own arousal. Inwardly glad that I was only semi stiff and my knickers were able to hold me in place.
My thoughts were interrupted when Mark said my name. I turned to look at him and instantly as my head turned to him he kissed me. I was shocked but also amazed how gentle the kiss was. I didn’t stop him and I kissed him back. He took this as a signal and his hands moved and he was cupping my bum and pulling me closer and grinding his erection into me.
I found the pressure of his hands on my bum highly erotic due to the sensation of the satin and sheer tights material being rubbed against my skin.
I slightly parted my lips and the tip of my tongue played on his lips moments later his tongue slipped in to my mouth and I just sucked on it as our lips pressed together.
The song ended and our embrace broke Mark looked at me bewildered. I took his hand and guided him back to our seat. But this time when Mark sat down I took a seat on his lap my arm around his neck and his arm round my waist. I leaned in and kissed Mark, his free hand went to my thigh and he caressed me from knee to thigh. The feel of his hand on my tights and thigh was everything I had dreamt it felt like on the receiving side those times it had been my hand doing the caressing.
Our lips pressed and I resumed sucking on his tongue. I knew what this meant to me. We stopped kissing and both tried to speak at the same time after letting Mark speak first. He checked I was okay. Before I could answer Gemma and Wendy stepped over they were heading home and checked if I was okay. I told them yes.
Gemma said, "Pop to the loo with me." I did grabbing my handbag leaving Mark with Wendy, Mitch and Gemma’s boyfriend.
In the toilets Gemma suggested I fix my lipstick and said, “Mark knows.”
“Knows what?” I said.
That Jessica has something a little extra.