The Outing of Lisa

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Lisa finally shows off herself to some unsuspecting friends.
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Over the years as a Out bisexual guy I have always tried to keep Lisa my far more feminine side hidden away. I spent many years dressing and loved it but decided when I had to move to a new house share it was time for Lisa to go permanently.

Unfortunately as many other cross dressers and transvestites know that is far easier than first thought to destroy a side of yourself that gives so much pleasure.

And as for me I found myself in different ways by meeting many trans girls for no strings sex whenever I could, loving having a sexy trans girl to pleasure and be taken by in some cases.

Finally I settled by occasionally dating one sexy cross dressing guy from my hometown who enjoyed being treated like a woman. I loved our times together having hard dirty unprotected sex together and sharing ourselves with others as well at fetish clubs and swinging websites.

I had been asked several times by others if I dressed as well and on the odd occasion I would slip on a pair of stockings and stilettos for sex games but unknowingly this awoke my other persona Lisa the transvestite cock loving slut that I had tried to get rid of and this is where the story starts.

I found myself on online auction sites purchasing heels, corsets and short tight dresses to show off my tight body. By this time I was 32 and needed a full corset to give me the look of a convincing girl.

I managed on a budget to find a lovely black and purple satin corset, hold up seemed stockings, full brunette wig and 5 inch satin peep toe heels all covered by a gorgeous figure hugging satin mini dress that suited my new look perfectly. I now felt like a girl again and all though I did not have the confidence to be seen outside as yet so dressed in my room.

I so loved feeling like a convincing girl and when I was dressed in my male mode I just did not feel right anymore, I felt I had to confess to my addiction, my secret life.

I chose my best mate to do so as I knew he was bisexual as well, first off I showed him a picture I had taken of me dressed which I had on a profile on a transvestite dating website. He simply asked who she was and if I could set him up with her for some fun as he knew I was well established on the local swinging scene as a hung bi lad.

I agreed I could, but told him she was a trans girl and was well endowed as well. This really did not bother him. He did say he had never had sex with a trans girl but fancied her and wanted to fuck her, little did he know that girl was me, his best mate in drag.

I agreed to set him up on a date and told him she would meet him at a pub in town I knew was trans friendly. Fortunately he decided he had to leave after a one or so to go get ready for his date, the date that would change our friendship forever.

As soon as he had left I showered and started to apply my makeup and shape wear, squeezing my body into a tightly laced corset, stockings, stiletto heels and dress. By now I felt great but so nervous I near poked my eyes out more than once on my mascara brush due to my hands shaking.

After about two hours Lisa was finally ready to go and face the world for the very first time, I picked up my mobile a second number I kept for sex meets and text my friend to say I hope he has still up for taking me not only out on a date but deeply from behind later on. He soon text back saying he was definitely up for taking me out and maybe giving me what I wanted.

I knew he would be there for 8pm on the dot so I ordered the taxi for just before eight as I wanted to be late just like any girl. One thing I forgot about stiletto heels is unless you are used to the them then stairs are a nightmare as I soon found out trying to get downstairs to my taxi.

I slid onto the back seat trying to look glamorous and sexy and could see the taxi driver having a good look on the way. We soon arrived at my pub of choice in the towns gay district, a classy gay bar that did not mind trans girls using it to pick up guys. With that I passed the taxi driver his fare and a tip and with that he wished me a good night and said if you don't get lucky give us a call and ask for mark. He was quite cute, in his late 20's and well built but blatantly gay. I just smiled sweetly at him as now I knew I had been clocked as a trans girl by him.

I made my way through the crowds of hot gay guys and girls with a few trans girls on the pull to the bar area where I had told my friend he would meet Lisa. I wiggled my way over to him and placed a hand on his knee to which he turned to look and met my gaze.

I introduced myself as Lisa and he followed suit but offered me a drink which I was more than happy to accept. As I stood by his side on my 5 inch heels I felt his hand slip round my waist, I just adored being touched when im fully dressed and turned to face him inviting him to kiss me. As I thought he did not waste any time in kissing me full on the lips.

I took his hand in mine standing him up and we walked across the bar to where there is a collection of leather sofas for people to sit and chat amongst other things if you were discreet.

He followed making sure any of the other guys in the bar did not try to touch me up on my way, in fact one did but I did not respond I just kept walking and trying to wiggle my bum just enough to keep him interested in my tight backside.

When we reached the sofas it was very busy and I decided to ask him to sit so I could sit on his lap. He did not refuse and seemed to enjoy having me there, we just sat and chatted for a while exchanging the occasional light kiss. I knew what he wanted from me and he knew I wanted it to as I felt his cock stiffening in his jeans and prodding my tight bum as I turned to sit facing him in a me on top position. He moved his hands to my waist and complemented me on how sexy I was before asking can we leave as I really like you girl and I really want to satisfy your need for cock.

I knew this was coming and knew he was going to ask me to have sex with him but then the nerves kicked in. I replied yes lets go and grab something for me to suck on.

We left the bar and jumped into a cab outside and headed to my place, the minute I gave the address to the taxi driver I saw a look of confusion on my friends face but I sat with him saying nothing.

Within minutes we were back at my place and he said to me a mate of mine lives here, I think you know him. I agreed I did and had agreed to use his place tonight as he was out with another girl in town or in bed by now. This seemed to work for a few minutes til I opened the bedroom door and he saw my makeup and case I kept my dressing bits in and recognized it from all the times he had been round to visit me as a guy, his best mate.

I took myself over to the bed and sat upon the side patting the duvet down next to me trying to get him to come over. In the end he submitted and came over but suddenly would not touch me. He asked if I was who he thought I was and I just nodded.

I was so scared that I was going to lose a friend at that minute I started to cry and told him all about my dressing and my love of being a girl. I was shocked as he wrapped his arms round me and pulled me close telling me he still found me very sexy and would love to fuck me still if I wanted him to.

I went off to the bathroom to clean myself up and douche myself as I intended to take his hot spunky load deep in my man pussy. I so loved being fucked hard when I was dressed and played a totally submissive role to any guys who were lucky enough to get with me.

I went back to my room all clean inside and out and stood in front of him and unzipped my dress letting it fall to the floor and show off my lingerie. He got to his feet and removed his clothes and his briefs showing off his thick 7 inches of man meat. I could not hold back and pushed him onto the bed and dropping to my knees in front of him. I slowly slid my hands up his thighs eventually reaching his throbbing cock which I slid into my mouth and started sucking him deep and slow into my wet slutty mouth.

He laid there moaning with pleasure as my tongue darted round his impressive bell end, I could feel my own 8 inches was rock hard in my lace panties. I got to my feet and he sat up seeing me stood in my corset and lace panties with hold up stockings and a large 8 inch cock protruding from my panties, he wasted no time in sucking me while he slowly slid a finger round to my bum and massaged my man pussy.

Now I really needed cock badly and I slid my member from his mouth and got onto the bed along side of him, he turned to face me and started to kiss me. I was in fits of ecstasy feeling all my senses going wild for him. He soon asked me if he was going to have the pleasure of fucking my tight pussy and I simply smiled and moved onto the bed on my hands and knees begging him to rim my tight pussy.

Soon I felt his hot tongue lapping a my juicy man pussy and he reached through and slowly massaged my cock. I loved it and started to grind my pussy deep into his face as I adore being rimmed. He seemed to know what he was doing and I was aching for his cock in me, with that I pulled away from him and asked him to lay on his back for me.

He moved form his position behind me to flat on his back, his cock was rock hard and had a glaze of cum across its hood. I reached for the dressing table and grabbing a bottle of my favorite lube began to massage it into his cock and my pussy while slowly playing with my love hole trying to prepare it for his cock.

No longer could I wait for him to enter me as I climbed on top of him and slowly lowered my tight cock hungry pussy onto his cock inch by inch until I felt his balls deep in against my bum.

With that I began to slowly ride his meat in and out of my well stretched hole, he soon had his hands on my side encouraging me to ride him harder and harder til I was being bounced off his thighs and moaning with each deep push into my willing pussy.

Soon my thighs could take no more and I had to dismount his meat, but I needed more and I wanted his cum dumped deep in me. I moved onto my knees and held the headboard of the wrought iron bed frame. I instantly felt his large cock opening up my tight pussy again, he had the one of the nicest cocks I have ever had as Lisa and boy he knew how to use it.

Within minutes I felt like a complete slut again as I felt his full balls slapping against my bum as he drove his meat into me all the time calling me his little fuck slut.

I was loving being screwed so deep and hard but I felt his cock starting to throb inside me so I told him to pull out, he did and started to wank himself off thinking I wanted him to cum over me but I still wanted more so I stopped him and tied a stocking tight round the base of his cock telling him I needed more cock first.

I did not know how long he could last til I would have to release him so I pushed him back down onto the bed and mounted him again taking all 7 inches without hesitation. The look on his face said it all as he felt my anus clamped onto his hard throbbing cock. I knew what I wanted though and I began to bounce on his rock hard shaft harder and harder.

Within a minute or two he was begging me to let him cum so with one hand undid the stocking from round the base of his cock and slid all the way down his throbbing cock to his full balls. As I did I felt him spasm deep inside me flooding my anus with hot spunk, ream after ream of spunk shot up my pussy til it was running back out and all over his balls.

He collapsed onto his back on the bed and I slowly climbed off his now flaccid and cum soaked cock. As I did he thanked me adding wow thanks babe that was one hell of a good fuck. I had to agree but I was not finished yet as I had not cum.

I asked him to suck me again and he rolled to the side of the bed before sitting up and taking my cock in his mouth, expertly he sucked me deeply and slid a couple of fingers into my well fucked bum playing with my g spot and sending me into a huge orgasm and filling his mouth with my own spunk.

He tried to spit most of it out but I had bent down to kiss him and share my hot load from his tongue, we kissed for a while sharing my spunk and then both showered.

I thought I would just go back to male mode but he asked if he could stay overnight and take me again the next morning so I slipped into a silky teddy and panties and slid into the bed alongside him and fell asleep with his cock resting up against my anus and his arm tight round my waist.

I woke with him rock hard behind me and wasted no time in him sliding his meat into me again and fucking me senseless til he shot his hot load deep into me for a second time. After I got up from the bed and went to get washed and cleaned out.

Upon walking back in he was sat there looking shattered but told me he was glad we had done it as he told me he had always wanted to fuck me and me being Lisa was amazing as he fancied my alter ego as well.

That was not the last time he plundered my man pussy but that is another story for another time.

Lisa xxx

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