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Introduction:

My first time as a true Transvestite

Hey everyone this is the same true story I wrote a few years back on a previous account (BisexualCockWhore) but in much greater detail for all you viewers ;)

If you want to read the shorter version I wrote on a previous account go to the link below:
http://stories.xnxx.com/story/28858/My_first_time_with_Joe


By the time I was 21, I had moved out of my old house and into a flat just outside of Birmingham City Centre, it wasn't much but for me, it was home. A place to call my own. A place where I could cross-dress freely without fear of getting caught out with a dildo in my ass. For the first week or so I didn't venture out much, unless I paying rent upfront or getting food and drinks from the corner shop. I would stay indoors, walking around either in the nude or any of my slutty outfits that I wanted to, playing with myself whilst developing a much curvier, womanly body.

Such freedom was a turn on for me, thankfully I had ordered a numerous amount of sex toys and lingerie from the Ann Summers website. That's the beauty of the internet, it allows cross-dressers like me to remain incognito to the public eye until they see fit to reveal themselves. One day, after pleasuring myself for so long in the shower, I decided that I would take the risk of going out in public dressed as a woman, but I would dress up in a pubic toilet stall in order to prevent any suspicion. So I packed my outfit for the day into a decent sized bag. Nothing slutty this time 'round, just a simple pair of blue denim jeans with a white tank top and high heels.

Feeling the sexual pleasures of attempting to cross-dress outside of my flat made me slip on a white lace thong with matching bra underneath my “male” clothes. I then headed out the door towards the city centre, where I would begin my public life as a full-time cross-dresser.
Whilst walking through town, I made sure to keep my head down in case anyone saw me, but I couldn't shake the feeling out of my head that someone was trying to get my attention.

“Hey!” I heard from a fair distance away, the volume in which it was shouted caused me to turn my head, thinking someone was calling me. But I didn't see anyone so I continued walking.
“Hey! David!” the person shouted again, once again I turned around but didn't see anyone. I picked up the pace to get away from the person but eventually they caught up with me as they turned me around by the shoulder. I was about to run until I saw who the person calling me was.

It was Joseph, my mums good friend and the man who had bagged me my first job. Granted that job was to look after his 13 year old son whilst he and his wife were at work. But it was a job nonetheless. Joseph had the been the man of my fantasies from the moment I first laid eyes on him. Whenever I saw him I'd just melt away into the erotic thoughts and today was no different.

“How've you been mate!” He asked joyfully as he hugged me. I had to resist my urges whilst returning the good gesture.
“I've been alright, just moved into my own flat up the street”
“Oh that's great!” He replied “Man it really is great to see you again, how about you come down mine for a drink?

My mind thought back to my original intent of cross-dressing in public, but since was a such kind-hearted man I couldn't refuse, so I put my task on hold for one hunk of man.
“Sure, why not?” I replied “I didn't have much planned today anyway”
“Super! Let's go then”
On the way back to his, we talked about things that had happened to us over the years since we had last seen each other. The whole time he was talking I just couldn't take my eyes off of him, although we was only 40 years old, he had the body of a god. Muscular, well-toned and a fine bulge in his jeans which left no stretch to the imagination.

Eventually we reached his house and he invited me in. When I walked through the familiar hallway once again it felt as if I had only been there yesterday as it looked exactly the same.
“Coke?” Asked Joseph as he got 2 glasses out of the cupboard.
“Please” I replied politely, noticing that the house seemed rather empty. As Joseph handed my glass I decided to ask him about it.

“Thank you Joe, Uh. I was just wondering, why does the house seem so quiet and...empty?”
As soon as I had asked the question, Joseph's eyes grew heavy and he slumped onto the old arm chair close by.
“I should've told you on the way here.” He said with sorrow in his voice.
“Told me what?” I asked, moving slightly closer to him.
“Me and Sandra, we divorced a few weeks ago”
“What?!” I said, nearly dropping my glass, only just catching it time. “Why?!”
“It was my doing” He replied, this time sounding a little more cheerful “She caught me in bed with a cross-dresser and -

Before he could finish his sentence, he was interrupted by the sound of my glass smashing on the living room floor. I had lost all control as I heard his words echoing through my mind. Did he really just admit that he had sex with a Transvestite?
“A-but-I-I Thought you and Sandra were happy” I stuttered, still unable to process his words properly.
“We were, but I just got tired. She would nag and bitch at me for no reason.”
“But why cheat?” I asked. Appalled but at the same time, intrigued.
“She just wouldn't have sex with me any more” He replied with more annoyance than sorrow
“I know it wasn't the right thing to do, but I enjoyed it. The man looked so convincing, even I forgot for a minute that I was fucking a Cross-dresser... Truth be told David.” He said, looking right into my eyes. As if trying to figure something out.
“Truth be told, I don't regret doing it, neither do I regret being caught”

“So, wh-what happened?” I asked, finally able to gather some of my senses again.
“We argued for weeks, until she just filed the papers and forced me to sign them. My son chose to go with her to Florida, I haven't heard from them since.”
“I'm...I'm sorry”
“Don't be” He replied with a sense of confidence “It opened my eyes to what I truly enjoy, I don't know why but I love to have sex with Transvestites, the thought of it just turns me on”

I could barely hold in my lust for him as he continued to preach about his love for cross-dressers, it was only then I realised the mess I had made a few minutes earlier.
“Oh god!” I exclaimed, looking at the mess “I'm so sorry!”
“Huh? Oh, it's no worries David, I’m sorry I shocked you so much.”

I said nothing as I went to get the dustpan and brush, in the place it always was. I immediately fell to my knees and started sweeping up the shards of glass, leaving the coke for the time being.

“David?” I heard Joe ask from behind me.
“What is it?” I replied, still sweeping up the glass.
“Is that a Thong I see?”

Within seconds of those words leaving his mouth, it clicked in my head. I had completely forgotten that I had decided to wear a bra and thong underneath before slipping everything else on. I immediately stood up and without saying a word and made my way towards the door.
“David!?” Joseph cried after me “Where're you going?”
“Home!” I replied, holding back tears of shame.
“Why?”
“Because I didn't do this for you!”
“Do what? The Thong?”
I nodded. “Joe...There's something you haven't known about me”

“I get the feeling I know where this is going” He said, ushering my back over to the chair.
“I'm...a cross-dresser. I have been since I was 15 and It didn't stop after I met you, rather...It got better. I’ve only just mustered the courage to wear the thong and bra today.”
“I see.” Was all he said.
“I've fantasised about you Joseph, for years now. But that's not why I came here today. I had no idea of what happened with your wife until today...I just...I want you.”

“So...” He said, standing up “All this time you've been pleasuring yourself over me? Dressing up like a woman?”
I nodded again, thinking he was angry at me until he lifted my face up to meet his eyes. Which showed care and lust.
“Well might I say I had a lovely view of you when you were bent over.” He said, giving me a reassuring wink that everything was okay.

With that wink, every feeling I had of running out of the door disappeared and were replaced with years upon years of lustful thoughts. I wanted him more than ever now, because I knew that he wanted me.

“W-would you like to see that view again?” I asked, still nervous despite my new sense of belonging.
“Would I ever!” I replied, ushering me to stand up.
Within moments I was bending over the arm chair, pulling down my jeans ever so slightly in order to give him the full view.
“Oh wow” he said as he marvelled at the sight of my clean, shaven, feminine body. “Sexy is only one way to put it”
“You like it then Baby?” I asked in a seductive tone as I bent further forward, arching my ass into the air in order to give him an even better view.
“Oh I love it!” He replied “Could you take everything off except your bra and thong for me?”
“Y-you want me to strip for you?” I asked, nerves creeping up my spine again.
“Yes, but don't turn around, not yet”

With that, I slowly took off my trousers along with my shoes and top, leaving me in just my lacy whit bra and thong, I even adjusted my hair in order to make it slightly more feminine.
“Incredible figure” I heard Joe say “You've definitely been at it for a while”
“6 years and counting baby” I replied.
“You can turn around now” He said and I did just that. I almost doubled back at the sight I witnessed.

There he stood, my hunk of a man naked as the day he was born, holding his rock hard cock with his left hand. I felt my own cock begin to stiffen at the sight of his beautiful monster of a cock.

“D'you like what you see?” He asked me “Because I certainly like what I’m seeing from my end”
On instinct I began to cover myself up as I had never cross-dressed in front of anyone except for myself in the mirror. I wasn't used to it.
“Don't cover yourself up David” He said as he moved closer towards me “Be proud of you gorgeous body...I only wish you had told me sooner, maybe it could've been you who got caught with me by Sandra.”

The thought of being fucked by Joe drove me to my knee's, directly in front of his bulging cock. I licked my lips in anticipation, but he stopped me before I could begin.
“I don't want to force you into this David” He said with sincerity in his voice “You don't have to do this if you don't want to”
“Joseph baby” I replied “I've been waiting for this day for over 6 years.

As soon as I finished my sentence I wasted no time in licking the head of his cock, causing it to twitch and slightly grow. I looked up at him with lust in my eyes and he returned the glance, granting me permission to at long last, suck his dick.

It felt amazing to finally be able to suck on my mans cock, I played with him a for while, licking the head of the cock or running my tongue up and down his shaft. I looked up to him as I took the first few inches of his cock into my mouth, flicking my tongue against it in order to drive him even wilder. I didn't stop at only a few inches, I kept taking more and more inside until all of his rock hard cock was at the back of my throat. I started to gag at first but then I calmed down and started a back and forth motion, savouring every last inch of my lovers cock.

“David! I'm-I'm gonna cum!” He shouted. But I didn't respond, Instead I grabbed his ass cheeks, using them as leverage in order for me to suck his cock even quicker. Whilst I continued to deep throat him, I slid a finger into his ass and within seconds I felt his cock twitch. Soon enough, shot after shot of his hot sticky cum was fired in my mouth and I swallowed as much as I could, but so much came that I had to come up for air and I was given a facial with his cum. Once he had finished I licked every last drop off of his cock and my face. He tasted so good.

“David...that was...that was” Joe said as he fell back onto the chair, unable to stand up after letting loose so much cum. It was obvious he hadn't had a blow-job in a long while.
“That was?” I asked, wiping off the last few bits of cum off of my face.
“Incredible...” Was all he cold say as he tilted his head back in pleasure, relaxing on the chair.

“oh no you don't” I thought to myself. I wasn't done with him yet, so I sat on his semi-hard cock and looked deeply into his eyes.
“You don't think that's all I ever thought about did you?” I playfully asked as I grinded up against him.
“Oh not by a long shot” He said “I think we should take this next part upstairs, don't you?”
“Baby you read my mind” I said as I got off of him to see that his cock had began to slowly grow again. I giggled with anticipation as he led me up the stairs, he then turned to me. But he looked concerned this time.

“Don't you feel bad about doing this?” He asked me.
“Why should I?” I replied with confidence. “Sandra's gone so there's nothing stopping me”
I grabbed his cock again, almost giving him another blow job there and then on the stairs, but he took me to the top floor and stopped at the first door on the left. He then carried on towards the end of the hall, leaving me at the first door.

“Aren't you coming in with me baby?” I said, playfully stroking my ass as I winked at him. I could see that he wanted to, but instead he carried on to the end of the hall.

“I want you to become the woman you want to be David. Inside that room is everything you need. I’ll be waiting for you in here my love.”
With that he walked into the room and closed the door, I moved towards the door in front of me and opened it slowly. What I saw within, blew my mind.

Inside was the treasure cover for any cross-dresser to come across, clothes of all forms were carefully laid out. Make-up on one table and a mirror on the other. I wasted no time in transforming myself into the woman that I’ve wanted to be since I was 15 years old. The process took no more than 10 minutes as I had experience with make-up and clothing before. I settled with a tight black and red corset with black fishnet suspenders. Combined with a pair of stiletto high heels. I styled my hair into a ponytail and applied a decent amount of make-up in order to make myself look completely feminine.

Before leaving, I took a look in the mirror, I didn't see a young man hiding from his nature any more. I saw a confident, young, sexy cross-dresser. I walked over to the woman in the mirror and started straight at it. Almost unable to believe that the woman in the mirror was me.

“You're no longer a man...You're a woman” I said to myself. Completely confident and for the first time in my life. Comfortable with who I was and what I was doing. I left the room and went down the hall, knocking on the door that I knew Joseph was behind.
“Come in” He said, so I turned the door knob and slowly opened the door.
The room was surprisingly empty, save for the double queen sized bed to the side of the room, Joe was standing with his back to me, still completely naked. He looked so beautiful, I fell in love.

“What d'you think lover?” I asked him, causing him to turn around. Within seconds of seeing me his eyes grew wide with amazement and his jaw almost dropped to the floor. I giggled and began to blush at his reaction, he was the first man to ever see me fully feminine and judging by his reaction, he really liked.

“You look...amazing” He said.
“Really?” I replied, blushing even more. “Better than Sandra?”
“A thousand times better than Sandra!” he exclaimed “David, you look so...beautiful”
“I'm not David” I replied with a stern tone “Not any more”
“Oh?” He asked with curiosity “So what do I call my lover now?” He said as we slowly walked towards each other, eventually holding each other in a romantic embrace. I looked into his eyes, glistening with love and lust and said;


“Call me, Davina my love” I said it with such confidence that a smile formed on my face “I'm your Davina”

We embraced in a passionate kiss for what seemed like forever. He then moved me over to the bed, still holding me in a lovers embrace, kissing the sides of my neck until we fell onto the bed. We lay there for a few minutes ravishing in each others pleasure, his hands ran all over my body; my curves, my ass until he eventually ran his hand over my rock hard cock. He looked at me with pure lust in his eyes and then slid me fully onto the bed, pulling my legs apart. He then reached over for the lube and covered his cock with it, sliding his lube covered hand over my ass-hole which made me giggle.

“Are you ready?” He asked, sliding his cock closer towards my ass-hole.
“Take me” I said, lifting my legs into the air “I'm yours”
Within seconds I felt the head of his cock pushing against my ass-hole. It resisted at first but Joe applied a little more forced and with a loud squelching sound, a good portion of his cock slid inside of me. The pleasure I felt from the first second of him being inside me was unforgettable.

He immediately began to thrust deeper inside of me, for a short while it was slightly painful but it soon turned into pure pleasure. The man of my dreams was fucking me, I was his lover now. I had replaced his wife. I was Joseph Janston's lover and the very thought of that made me moan in ecstatic joy as I moved in time with his thrusts, each one going deeper and deeper. I clung onto the bed sheets as my moaning grew louder and louder, I was in heaven, I had never experienced another mans cock inside of me before. It was beautiful, it was everything I dreamed it would be and more.

“Oh god...” I said as he continued to fuck me “Joe you're so...so...fucking good”
Joe didn't say anything as he lifted my legs further into the air, driving his cock deeper inside me. Which in turn made me scream with pleasure, I didn't care if anyone heard us! I wanted the world to know of the pleasures I was receiving.
“Joseph!” I screamed “Fuck me harder baby!”
“Are you sure?” He replied, still pounding away at me.
“Yes!” I exclaimed “Bend me over and fuck your lovers ass! I’m all yours now! Fuck me!”

Without a moments hesitation, he turned my body around and made me get on my hands and knees on the bed, I leant forward in order to stick my ass further into the air, Inviting him to take me.
“It's all yours baby!” I said “Take me”
He then grabbed my curves and drove his cock all the way inside me. I screamed into the pillows as I felt his giant cock thrust in and out of me, I lifted my head back up and looked into his eyes.

“D'you like it baby?” I said in-between gasps “D'you like my tight ass?”
“I...fucking...Love it!” He shouted as he pounded me harder and harder.
“Don't stop then!” I said as I grabbed hold of my cock and started to jack myself off. Adding to my already endless river of erotic pleasure.
“Davina!” He shouted, his thrusts getting faster and harder “I'm gonna...I'm gonna!”
“Don't tell me!” I said, moving my body in time with his “Just let it happen”

We both went silent for a few seconds before moaning in unison as he fucked me in the ass and I jerked myself off. As I felt my own cock begin to twitch I also felt his twitch inside me, I didn't want to waste any of it so I furiously pounded away at his cock, jacking myself off at the same time until I heard him scream from behind me and I began to feel his hot sticky load fill my ass-hole all the way. The sheer pleasure of his cum filling my ass-hole drove me over the edge. I let out the loudest scream possible as I came all over the bedsheets, even thought we were both cumming, Joseph continued to fuck me. I felt every morsel of cum flow out of my ass, leaking out onto his cock and eventually onto the bedsheets until we both collapsed in absolute exhaustion.

We lay there in our own cum soaked bedsheets for ages. Occasionally kissing and fondling each other, it was pure heaven. And I had no intention of leaving it.
“That was...the best I’ve ever had Joe” I said softly, gazing into his eyes.
“The same goes for you sweetheart” He replied with a cheeky wink. I giggled in response and lay back down as he continued to kiss me.
“I'll get your bag from downstairs” He said “That way you can clean yourself up”
“Do you have to go?” I said, feeling sad for the first time in a while. I didn't want him to leave my side.

“Unfortunately yes” He replied “I have a friend from work coming down soon. I just wasn't expecting this to happen”
“Do you regret it?” I asked, the feeling of worry and doubt creeping up on me.
“No” he replied sternly “Not in the slightest. I’ll go get your bag sweetheart”
With that he kissed me one more time on the lips, then showed me to the shower. My mind raced with the many thoughts of the two of us fucking in the shower, but I knew he had other matters to attend to so I slipped out of my lingerie and cleaned myself up. About 5 minutes into my shower the door opened and my bag was placed just by the door, after I had finished my shower I picked up the bag and went back into the room filled with clothes and make-up.

After about 10 minutes I emerged from the room with the look that I had intended for originally. White tank top with blue denim jeans and high heels, I even had my white lace bra and thong on underneath to complete the outfit, along with some perfume and make-up.
I headed downstairs and heard Joe's voice along with another persons. I felt nervous again as I continued to go down the stairs, this time at a slower pace. Eventually I came face to face with the friend that Joe was talking about.

“Well well well” He said in a charismatic tone “This is the woman that's replaced Sandra?”
“The one and only” Joe replied “Brian, meet Davina. Davina, this is my friend Brian”
Brain jokingly bowed in front of me, I couldn't help but let out a small chuckle.
“Pleased to meet your acquaintance Ma'am” He said, causing me to blush and stutter. Before I could say anything he stood and said;
“Don't worry hun, you're secrets safe with me”
“Wh-what?” I replied. Shocked by what he said.
“I know you're a cross-dresser” he said flatly “I must say you did have me fooled for a minute, but nonetheless your secrets safe” He winked at me, making me blush again.
“Th-thank you, Brian” I managed to say. “Pleasure to meet you as well”

Brian chuckled, then looked over to Joe again.
“He's one hell of babe!” he said, slapping my ass which made me jump towards Joe.
“That he is” Joe replied softly, then looking to me “I'll see you tomorrow then sweetheart?”
He looked into my eyes as he said it, making me believe that I was more than just a horny fling. A huge smile grew on my face as I nuzzled in his chest whilst he held me.
“Yeah, I’ll see you tomorrow” I said, eventually tearing myself away from him and making my way to the door.

“Oh hey! Davina!” I heard Brian shout, as I turned around I barely caught my keys that he flung at me.
“Don't forget those!” He bellowed “Also, Joey-boy here forgot to mention that he snuck his own key onto your little set there.”
I looked at my key-chain and realised that Brain was right, one of Joe's bronze house keys was hanging along side mine. I smiled at the two of them and thanked them as I made my way out of the house. I walked down the street, finally feeling like myself. The person that I was meant to be, any previous doubt or concern about anyone picking me out as a man wearing womens clothing had boiled away to nothing.

On that day, I walked through the streets of Birmingham City Centre as a woman. No-one knew the wiser, I even saw some guys looking at my body, I could only imagine what sort of perverted thoughts were going through their heads at the time and they filled me with joy. I had succeeded in becoming the woman I was born to be and I had also bagged an amazing lover in the process and what happened a few months later made everything all the more perfect.

Part 2 will be coming soon xxxx

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