Becumming Lisa

I have always known deep down that I am a transgender person, born a guy but never felt happy in my body and because of this I knew something was not right, this is my story of how I have got to the stage of my life.

This is all true and edited for Literotica's readers, I pull no punches at all and have experienced a interesting life so far.

I hope you enjoy reading this and leave me some feedback, if you like I will write more soon...x

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I have dated women as a man and it never has worked, my last attempt being little over 5 years ago I met someone online and she replied after a lot of chatting with a response to one of my mails shocking me to my core when I opened the mail and read

"I thought you were gay or a cross dresser"

I had always tried to keep my secret life as a transgender person secret from the outside world but it seems someone out there had leaked my secret to the world and now I knew it was time, time to face the world and say yes I am gay and yes I do cross dress.

By the time I was 18 or 19 I was rooting through my parents drawers, I knew my mother secretly hid her sexier side and finding a silky tight fitting white satin basque, panties and white lace top stockings I slid the items onto my torso and then found a pair of 4 inch heels that did not quite fit but felt amazingly sexy.

Knowing I was doing wrong I instantly removed all the items and put them back making the drawers look as though they had never been moved as so many cross dressers start out.

I dressed for several years in secret and one day as I approached my early twenties I had a mate coming round for a few beers before we went out and as he sat I found myself thinking how I would love to suck his cock and maybe have him fuck me in my tight virgin bum.

Not able to control what my brain was doing I found myself locked in the bathroom sliding into a very tight black lace and satin corset with black lace topped stockings and panties, not thinking this was wrong as I slid on a pair of 5 inch heels and wanked myself to orgasm so I would not get hard in front of him.

My mother was out at work so no problems there and as my parents had separated I knew my father would not be around so as I went to go to my room to get my wig from its hiding place there was a knock on the bathroom door, stammering I answered yeah all right what's up?

My mates voice boomed back what you doing in there I need the toilet mate.

Telling him to wait a minute as I had a bad stomach he said fine I will wait downstairs yeah. My nerves had now kicked in and my legs felt fragile and shaky but I was adamant I was going to go through with this.

Wobbling my way in my heels to my room I shouted down to my mate that the bathroom was free as I slid into my room and fixed my basic makeup and wig into place, moments later I heard the bathroom door open again and footsteps heading towards my room.

As usual my mate Paul didn't wait or knock on my bedroom door and as he walked in I was fully dressed like a little slut waiting for his prick, thinking he would be impressed he just stood there and said what the fucking hell are you doing you pervert, standing and walking to him I just said now you know I am a tranny and I really want to suck you off and have you fuck me if you would like to?

I should have expected the answer I received as he turned and said I am fucking leaving.

As he made the front door I had kicked off my heels and chased him down the stairs and managed to lock the bolt on the front door as he tried to open it.

Begging him to stay he relaxed and I said im sorry mate but this is who I am and maybe I got our friendship a bit wrong, his answer somewhat shocked me though as we were to go bowling that evening and he said you can go dressed if you want to but there is no way we are having sex together as I just don't fancy guys.

Thinking better of it I went back upstairs and got undressed then chucked back on a somewhat boring pair of jeans and a jumper, secretly though I kept on my hold up stockings and panties and hoped in some way I may pull either a guy or maybe a girl who would be turned on by me wearing sexy lingerie under my masculine clothes.

That night surprisingly I didn't pull....In fact I went home alone and drunk...

The biggest shock was as I decided to go to bed my mother walked into the room with my corset in her hands and said I knew you were dressing, its disgusting and you will stop this adding how do you expect to ever find a girl friend and settle down when you are doing this.

Screaming at her for obviously going into my room in the first place she said.

You know I always clean both you're and your brothers room when I get in as you two are too lazy to do it for yourselves and by the way we are moving

With that she left slamming my bedroom door behind me and worst of all she had taken all my feminine clothing away.

From then on my dressing stopped and I tried to be straight, now for those of you who know and accept you sexuality you will know how difficult it is to be someone you most certainly are not and after a relationship that failed badly I knew my mother accepted that I was probably gay but no word has ever been spoken about it.

As life moved on I was forced to move out of home and find my feet, I suppose as I was in my mid twenties my mother did me a favour by asking me to move out, however she did not realise was what I would become.

Now I know you are probably thinking so now you became the transvestite you have secretly hidden all those years but no, I became a drug addict instead as I continued to hide behind a life of drugs and alcohol to take away the feelings I had inside.

Some of my friends I think realised, one evening though with my best friend and his girl friend I decided to come out and told them both I was bisexual.

My mates girl friend said she kind of knew anyway as she was also bisexual herself and had read the signs.

I spent over 10 years as a drug user and addict and finally when I moved into a shared house with people I did not know my urge to dress suddenly reappeared and after one evening of watching football in my bed sit with another guy from the house I admitted openly to him about my sexuality as I was sure he was gay and I was right too.

Soon enough I found I had locked my door and was on my knees servicing his cock with my virgin mouth, he was not the best looking of guys and in his early 50's when I was just in my mid to late 20's but his cock felt good in my mouth, as I lapped at his bell end he encouraged me whilst telling me how he believed I was straight until that evening.

As he asked me to stop before he was going to cum I pulled away and stripped off for him to suck me as I adore being sucked whether I am dressed or not but he had other ideas and as he saw my young tight body he said how about I fuck your bum for you.

Nervously I agreed and although I knew I had wanted this for years he really was not the guy I had imagined screwing me for the first time but as I felt his fat bell end opening me up I tried to relax but the pain was intense, soon I started to relax and as I had a bottle of poppers pushed under my nose and the feeling of losing control set in I became the slut I love to be for guys when I am being fucked.

Feeling his thick hot cock deep in my butt was amazing and as he did me doggy I could fantasize about who was fucking me, the only problem is he could not last long enough. As I felt him losing control the fear washed through me as I felt him cum inside me, the thoughts being infected with something took over and I told him to get out and never speak to me again.

The next time we saw each other was in the shared kitchen in the house the next morning and he apologized and said we should never have sex again as he thought I didn't enjoy it, pulling him aside I said you can fuck me anytime you like but next time you use protection and with that we stayed friends and had sex one more time a few weeks later as I was stoned and drunk again.

Staggering up the stairs to my room I found myself knocking on my friends door at 3am begging him to fuck me, alcohol always sets me off and makes me super horny. Waking up and answering his door I had got my cock out and as he stood there naked I felt repulsed by his older frame but knew he was the only gay guy I knew and I wanted to be fucked.

Dragging me into his room I stripped and knelt on the end of his bed with my bum in the air begging him to fill me with his cum again, I didn't have to ask twice as once again I felt his thick member opening me up and this time it didn't really hurt but I think I was that wasted that you could of stuffed a marrow into my arse and I would of loved it.

Feeling him banging me deep, his balls slapping against my arsehole as he grunted and told me what a little queer I was just made me beg him to do me harder and deeper and this time he just kept going. I don't know how long he was in me for but it felt like ages and eventually he pulled out, rolling over I said why have you stopped.

Looking over he was sat in his armchair breathing heavily and he just gasped; I am shattered but give me a moment.

Crawling over I took his man hood and began sucking him deeply making him moan softly as he ran his hands though my hair that I had been trying to grow enough to look slightly androgynous and girly.

As I lifted my head away from his prick once again he was rock hard and as I turned and cocked my hips in a very girly fashion he stood and without warning sunk his fat cock back inside me, filling me until I felt his balls smash against my arse hole.

Slamming me hard against the wall he pounded into me as he pulled my hair and started to become verbally dominant telling me that's what little sluts get when they wake him for a fuck, what he didn't expect was I was in heaven having my hair pulled and my boy pussy pounded full of cock which pleased him even more and sure enough as I began pushing back into him making sure I got all of his cock inside me.

Bucking like a trained porno slut I knew right then I was gay and I loved having my arse pounded deep full of cock and of course my friends spunk, soon he was saying he could take no more yet I needed it all night and told him to fuck me as hard as he could.

Sure enough he was not going to disappoint me and as he slammed into me again he soon was gripping my slim waist, feeling his grip tighten and his cock starting to throb hard I knew for sure I was about to become his cum bucket again and sure enough he shot 2 or 3 loads of spunk up my butt before he collapsed back onto his bed.

Not even thanking him I picked up my keys, phone and clothes and walked to my room butt naked with cum running down my thighs and got into bed only to wake up some 7 or 8 hours later sore and not 100% sure what I had done the night before.

A few weeks later my friend moved out, once again I found myself hunting for cock and in my search I moved home twice hoping to find a live in fuck buddy again, this time I was not so lucky and ended up in a bad way with serious addictions taking over my life and any prospect of work lasted a matter of days normally before I would get in a fight or just not bother getting up.

Sure enough I was in a bad state and after I was rescued by a friend who took me away for a month and when I returned I knew what to do, first I got clean then I moved house again to yet another house share taking out a big loan to pay the deposit and rent.

Things started to get better and suddenly without any control I found myself on a popular auction site ordering clothes, lingerie and loads of other girly bits like nails and makeup.

As soon as I had clicked the button to confirm my purchases I thought what have I done but as soon as I relaxed I knew Lisa was back and her need for cock was as ravenous as ever.

Need I say more, well a few days later my purchases arrived and as I got in I instantly closed the curtains and fully dressed behind closed doors and that has been where Lisa stayed for some time.

I have since had many sexual encounters and bar my work hours I live as a trans girl, I have lots of tales to tell about my experiences and would love to read your feedback.

Lisa xx