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A Night of Firsts

Tags: oral, anal, club
Jessica goes out for her first time and finds herself and a lot of fun

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. It suddenly dawned on me, from the moment I had come out of the toilets from Gemma’s talk. I hadn’t thought about myself as anything other than female and I had felt and desired as if I was a woman.

Gemma explained Mark is a friend of Mitch. He knew about Mitch and Wendy and he told Mitch a while ago that the thought that he might be attracted too crossdressers. But Mark didn’t want to hook up with any of our friends.

"So when you turned up at the bar, Jessica and we saw you and you were clearly alone. We decided to see if you were game for some fun that’s why we did the cocktails you didn’t get offended. Sso we realised you might be what Mark needed and once we talked with you Mark might be what you needed. We sent him a photo of you and he liked you so he came down to the club."

At first I was upset by this revelation but then I realised none of my behaviour had been because of this. It had been because I had wanted to behave like this and actually realised I should be flattered Mark had made an effort based on my picture only.

“Thanks for telling me the truth, Gemma,”

“What does he expect from me?” I said.

“Honestly, Jessica I don’t think Mark knows what he expects or wants from you,"

"He may just like the idea of crossdressers, besides it’s your decision what happens not his,” responded Gemma and handed me my handbag.

“I best get back out to my date,” I said without thinking Gemma just smiled knowingly.

Mark was waiting with the group when Gemma and I came out. Gemma and the others said their goodbyes and left. I sat on Marks lap again and whispered in his ear, "Shall we go for a coffee?" I thought it best clear to our heads a little.

He collected my coat from the cloakroom and helped me put it on such a gentleman. I rewarded him with taking his hand as we walked out of the club. He said there was a coffee place five minutes walk away. So we set off as we walked we talked.

We got to the coffee place and I was in shock it was a 24hr McDonald’s. Mark just held my hand and led me straight in. He ordered our coffees and we sat out of the way.

It took thirty minutes for the coffee’s to cool enough to drink. So we talked some more and Mark caressed my thigh under the table which I didn’t stop. He said various compliments that I was beautiful and looked great. I didn’t believe him but blushed all the same from the compliments and the caress of his hand.

I was feeling better and better so I rested my hand on his thigh and lent forward and kissed him on the lips. His hand moved to my inner thigh under the skirt of my dress.

“Not here,” I said and he moved his hand back.

"Shall we walk?" I suggested and he agreed.

We walked out hand in hand.

We walked talked and kissed until we finished our coffees. Out in the night air our kissing got more passionate,. His hands cupped my bum again and he pulled me in clos. His erection evident in his trousers as it pressed my hip. I was sucking on his tongue as we kissed he ground his erection into me and I pressed myself into him to feel it more.

My mind swirled and finally I accepted the next first of the night. I pulled Mark into an alley away from the street and my hands rubbed his erection. I found his zipper and lowered it my hand went inside his trousers and inside his boxers and my fingers wrapped around the first man’s cock I had ever touched in my life. I eased his cock into the night air and started masturbating him.

His kissing slowed as his focus went to what was happening to his cock. I broke our kiss and slid to my knees in front of him. I honestly believed at that moment I wanted to suck his cock more than he want me to suck his cock. I guided his cock to my lips and stuck my tongue out and licked the head and the wetness dripping from his slit.

I thought it tasted great and licked more and soon my tongue was going all over the head of his cock. My hand held the base of his cock and my lips slowly engulfed his cock. The warmth in my mouth was wonderful. I wanted this so much I realised. I just swallowed as much as I could and soon my mouth was bobbing back and forth on his cock as I gave my first blow job.

I cupped his balls and sucked for all I was worth relishing the position I was in. I felt him tense and he mumbled I’m going to cum. I had made my decision already and just continued sucking moments later his spunk was in my mouth and without pausing I swallowed. I held his cock in my mouth until he started softening and licked the last drop of cum of the tip of his cock.

As I stood up I noticed my knickers were soaking with my own juices though I had not orgasmed myself. I was immensely aroused. I returned his cock to inside his trouser and zipped him up.

He thanked me my pleasure I responded and I meant it and we kissed. His hands cupping my bum instantly. Mark took me further into the alley and pushed me against a wall kissing me as his hands moved up my skirt rubbing my inner thighs. His hands slipped inside my tights and knickers and he held me.

“I like you clit Jessica,” he said and to me it felt right for him to say that.

His hand caressed me and I naturally spread my legs to give him greater access. He kissed me a moment longer then went on his knees he pulled my tights and knickers to my knees and gentle spread my legs a little more. He started to kiss and lick me and it felt amazing his hands cupped my bum as he licked and kiss me.

I was leaking like a tap and he let some of my juices drip on to his fingers. He placed those fingers at my bum hole and applied some pressure. I didn’t resist and actually wanted to get the next first of the night. His finger popped in my bum he pushed it in further until eventually he was knuckle deep and I enjoyed it.

I just looked down to him and murmured “Don’t stop.” 

His finger slowly withdrew but before coming out he pushed back in and continued over and over again the sensation was amazing and I wanted it more. The feeling of his finger on my anal canal was wonderful and the invasion of my bum hole itself felt perfect. I didn’t want it to stop.

“Two?” he said and I knew what he meant instantly.

“Yes,” and on his next thrust a second finger entered me and I moaned with pleasure. He finger fucked me faster and faster and I could not believe the pleasure.

Without a word a third finger went up me and he fingered me more. I was getting so close to orgasm. We heard sirens and panicked, Mark stood up but still had a finger inside me but the special moment was gone. But I was gaging to orgasm so when Mark suggested going back to his place I didn’t hesitate.

I pulled my knickers and tights up and we walked to a Taxi rank. All the time we walked I felt empty in my bum hole and couldn’t believe how much I wanted Marks finger in my bum.

We got to Marks house and went inside and headed straight for the bedroom. I stripped first trying to be as erotic as possible soon my dress was on the floor and my boots lay next to them. I kept on my bra, knickers, waist clincher and tights.

I grabbed my handbag for my lipstick to reapply it that’s when I noticed a package. 

For Later – Love Gemma it read I quickly opened it and found sachet’s of lube and a condom. I threw the lube on the bed and did my lipstick.

I stepped over to Mark and undressed him. Paying special attention with my hands and mouth to his cock and he was soon hard and dripping wet. But that wasn’t why I had come back to his place.

I lay on the bed and spread my legs and ripped a hole in my tights over my bum hole and pulled my knickers aside. Mark got the message. He again used some of my juices on his fingers and started with one then two and finally three.

The advantage of laying on my back was he was between my legs and I could feel his body rub the sheer material of the tights against my inner thighs which was absolutely arousing and we could also kiss.

His fingers pumped my bum hole and I was in heaven. I could feel the orgasm building.

“On all fours Jessica, so I can get deeper,” even though I was perfectly enjoying being on my back I was wanton for the orgasm so flipped onto all fours.

Moments later Marks fingers were in me again and in this position he could find my g-spot. I started moaning and whimpering as he worked his magic my eyes closed in bliss my head buried in the covers.

"Just a second babe I need more lube." 

“Whatever,” I said “Just fuck me till I scream.”

I felt him apply lube to my bum hole and his finger at my bum hole he pushed against my bum hole. It took a moment before I realised this felt different I felt my bum hole expand and discomfort.

I lifted my head and looked behind me and could tell straight away it was Mark’s cock in my bum hole not a finger.

“No!” I said

This wasn’t a first for the night I was prepared for and started to wriggle free. But as I did Mark lost his balance and collapsed on me this drove his cock deep in my bum.

As Mark attempted to get up I stopped him. I hadn’t anticipated what it would feel like once the length of his cock was in me.

"Give me a second I’ll get a better balance to move."

“Just stop moving a second.” I said.

The discomfort and pain was gone now that he was fully in me and his cock filled me up and was touching my g-spot. I was enjoying it there.

“Mark you are forgiven but get a condom on,” I said.

“I have already,” he responded.

“Okay take it easy but fuck me," which Mark proceed to do.

Starting of slow and steady the feel of his cock spreading my anal canal with each thrust and the tip prodding my g-spot was amazing. My orgasm was building quick even the spreading of my bum hole was okay.

Mark’s pace quickened and I found myself pushing back on each of his thrust for a deeper feel and I was clearly enjoying being fucked as I moaned and whimpered.

Then it hit me an orgasm like I had never had before my legs went weak and my bum spasmed over Marks cock. I ejaculated into my knickers and it was the best orgasm I had ever had.

As I lay there shaking and moaning Mark pumped my bum with his cock and I just didn’t care. I actual felt good with his hardness inside me then Mark thrust deep inside my bum. I felt his cock spasm and loved it. I was the Jessica I had always meant to be.

We disentangled ourselves and lay next to each other. We kissed and said how great it had been. I could see Mark was getting drowsy so cuddled up to him in the bed. A few moments later Mark was asleep. I decided to leave and got dressed and made myself presentable. I picked up Marks phone and scanned for his number and put it in my mobile. I left a note and called a Taxi.

Back at my car I got put my handbag and coat on the passenger seat and got in. I used a mini breath test kit to check I was safe to drive. The drive back from Nottingham to home gave me time to think of the many firsts I had that night. My body felt strange it was missing the feeling of being filled. By the time I arrived home I had decided to see if Mark was interested in meeting again.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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