Latest Forum Posts:

Categories

My first boy experience

First time cross dresser ends up with well hung guy..
It was my friend, Karly's birthday. Her choice for going out to celebrate was a drag night at a club. It wasn't so much fixed on drag as it was on gender parodies and cross-dressing for fun. I had been a closet cross-dresser for a long time, although I had told a couple of girls I knew. Everyone was going to cross-dress and have fun, but I was going to revel in it. I had never been with a boy before, not even kissed one, but every time I was in women's clothing I wanted cock.

During the daytime, I hung out with Karly and my other girlfriends including Olivia and Sinead. I had always seemed to find it easier to get on with girls than guys. We chatted generally before they asked what I was planning on wearing. I laughed, slight uneasily saying I wasn't sure. They asked me how far I planned to take it and I said that I'd shaved my legs anyway because I didn't like body hair.

"Well we could help you get ready, see what looks good on you," said Karly.

We rummaged through Karly’s wardrobe, picking outfits for me to try on. They decided on a black sequin dress with a thin brown belt around my upper middle. Luckily, Karly and I were size seven, which meant I could borrow a pair on her heels.

"Are you going to paint your nails babe?” asked Sinead.

A couple of times they had caught me with painted toes and not said anything. I just don't think they thought much of it. I knew if I came out as pretty much a girl, they wouldn't treat me any differently. I was pretty much one of the girls anyway.

"I'll paint my toes. I don't think my finger nails are long enough."

It was true, every time I tried growing them out I'd give in to temptation and start biting them.

"I have fake nails for you babe, I can bring some stuff just to give you a bit more cleavage," said Olivia.

Olivia popped home whilst the rest of them started to get ready. They all had borrowed suits from boyfriends or other male friends. They applied fake facial hair with liquid eyeliner, and opened a bottle of wine.

Olivia returned, practically ready, wearing a shirt tucked into trousers and a denim jacket. She'd slicked her hair back. I offered to do her facial hair for her since she was applying my fake nails. I gave her a comical moustache, long and curled like Salvador Dali.

She sat me down at a small table so she could sit across from me and applied the fake nails for me. We chatted about tonight, how much money we were bringing out and who would be there. She finished applying the fake nails and asked what colour I wanted. I decided on a darker red, like a sexy. I tried to be nonchalant, as if I didn't really mind. I had done most of my own make up, borrowing bits and bobs from each of them. My eyelashes were curled, my eyeliner done and my lips red.

When I was finished I stood up and looked in the mirror. Wow, I looked like a woman. A female and I was horny.

"Wow don't you look great!" said Sinead. They each gave me compliments as they continued to get ready. More people began to come round to Karly's flat, ready and dressed. Everyone was laughing and having fun, it was a very relaxed atmosphere.

We called taxis as it was getting late and we all definitely wanted to get in. We arrived and walked into the club. People bought shots, exchanged hugs. The crowd was mixed with drags, queers, transgender folk, gender feud, cross dressers.

Karly and Olivia and I were standing at the balcony, enjoying our drinks.

"Seriously, I can't believe how convincing you look. You look 100% like a woman."

I closed my eyes, in a melancholy moment and a tear ran down my eye.

"Aw babe what’s up?!" They both put their arms around me.

I opened up and explained that I had been cross dressing for a long time and wanting to go out as a girl for a long time. They hugged me, telling me they didn't care what I wore.

"Well, I knew you were effeminate babe, painting your nails and shaving your legs. But you know you should've told us sooner, you can always be one of the girls."

I was so grateful and hugged them back and told them how much they meant to me.

The night passed and around twelve people went back to Karly's flat after the club had closed. A boy I knew called Sam had turned up just to Karly's as he'd been out for his cousin’s birthday in another club. Sam was mediocre looking but tall with a beard. His hair was longish and he always had it pushed back. Whenever I was around Sam and his male friends they always made jokes about his cock. They called him donkey dick, huge tool. It was all harmless and hadn't even really seemed to help him get more girls. I knew not all girls really wanted big cocks and muscles.

However, I had imagined his tool, fantasizing about it. I imagined how huge it was, how long and thick it was. I wanted it in my mouth. I wanted in my hands. However, I knew it would never happen.

People slowly started drifting away, either going home or finding a room to crash in. It was me, Karly and Sam left in one room. Karly leant her head on my shoulder and I leant mine on Sam’s, hoping he wouldn't mind too much. Karly's phone started to ring and she picked it up and went out the room to answer it. It was just me and Sam alone.

Liquid confidence told me to rub my head against him. I did so slowly moving my arms across his chest. He looked down and we began to kiss. His tongue was deep in mind. My hands explored his chest and he explored my legs. Did he know what I was? Did he care? I was leaking pre-cum anyway.

I don't care if it was going to be slutty, I had been dreaming of this for so long I was going to get what I wanted. I stood him up and kissed him, making my down. I undid his belt. The anticipation was killing me. I wanted his cock.

I pulled his boxers and his lovely long cock popped out. It barely erect, yet it was huge. I took my hand and started to slowly wank him off. I sucked the tip and his cock grew. I took my mouth out just to look at his cock. It must've been 8 inches long, at least. It was so thick my mouth ached. Yet it was delicious.

I began to suck it again, using two hands to wank him whilst sucking on his tip. I licked his balls, sucking on them. Sam groaned in ecstasy. I began to suck him off again. I knew this was slutty but it felt so good. I was sucking his huge cock. My mouth struggled to get half way down his length. I sucked my hardest, wanking him faster and faster with my two hands. His breathing got heavier and he grabbed the back of my hand and shot his load down the back of my throat. I came in my own pants. It had all been so sexually invigorating. He pulled his pants back up over his cock and bucked his trousers up.

"I need to go but can I get your number."

I wrote it down on Sam’s phone and he walked out, just as Karly walked back in. Karly looked around confused.

"What just happened?"

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

To link to this sex story from your site - please use the following code:

<a href="https://www.lushstories.com/stories/crossdressing/my-first-boy-experience.aspx">My first boy experience</a>

Comments (5)

Tell us why

Please tell us why you think this story should be removed.

Reason