My first time with Joe – by CD-Davina20

True gay story: My first time with Joe by CD-Davina20. 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 😉

True gay story: My first time with Joe – Chapter 1A

by CD-Davina20

Genres: True Story, Gay, Hardcore, Oral Sex, Transvestite

My first time as a true Transvestite

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.


“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”

Also in this series:


Leave a Reply