My Beginning Pt. 01

Story Info
A young man's journey into womanhood.
1.1k words
4.32
18.7k
11

Part 1 of the 4 part series

Updated 06/10/2023
Created 07/20/2021
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
101again
101again
23 Followers

I had always been curious about men. By fifteen I had been with my first girl but I didn't enjoy it, perhaps it was the fact we were both young and inexperienced but I didn't find myself attracted to her.

The summer I turned eighteen, I had been perusing craigslist awhile but finally decided to post a M4M ad. It was intended to just chat and see how I felt about men, even though I had been sexually curious for a long time.

An older gentlemen, 54, messaged me. His name was Charles. He was very sweet, unmarried, just looking for someone to talk to. I had a suspicion that he wanted more but I was young and lonely, and incredibly curious.

Everyday for the next two weeks we messaged one another. He kept an odd schedule as I did, so after work I would send him a message on AOL (I feel old now!) We would stay up until two or three in the morning getting to know one another.

I'm a fairly old soul so the two of us really clicked. Then, one night, we started talking about sex. He asked what I wanted to try, what my boundaries were. I told him I wanted to try bottoming and topping, oral, kissing, most normal things. I wasn't too experienced with kinks yet. We talked about this until daylight. He was gay all his life, which was difficult growing up in the small communities we both lived in. I asked him if he would be willing to teach me a few things. He responded with caution, the age difference. Talk was one thing, actually doing it was another thing entirely.

The next couple days were back to our normal chats; talking about life, politics, our communities. Then he asked if I still wanted to come over. I was shocked! I said that I would adore that!

We planned for Thursday night, it was a Sunday night we talked (I believe). I asked if I need to bring anything, a change of clothes if I want to stay the night.

Fortunately he lived close by. A small town to the north about forty miles. That night I was shaking the entire drove up there. What if he didn't like how I looked? (We never exchanged photos, only stats and vague descriptions.) What if I don't find him attractive? Being the first man I will meet as an intimate interest. I can't do this! I froze and drove all the way to his place. I couldn't bring myself to turn around.

I pulled up to his address. It was a cute home in the country. The Blue Bonnets on his front porch were large and well taken care of. I walked up the steps and he was already at the front door to greet me.

I was taken aback. He stood in the doorway with a large, genuine smile and a kind face. Standing at 6'3", he was just a few inches taller then I was. His barrel chest and arms out stretched were so inviting, I instantly went in for the hug he offered. He asked how my drive went. "Good." I replied shakily.

At the time, I played football and wrestled. I was thin but muscular and hairy. I was self conscious about the hair.

He invited me in and we sat in the kitchen, talking most of the night. The entire time I took in the figure before me. He was incredibly handsome to me. A kind face with a rugged build. I was attracted to this man. He said multiple times that I was far cuter then he had envisioned. (That made me have butterflies!)

Finally, I asked if he wanted to do anything. He said, "Certainly! Only if you are comfortable though." I nervously shook my head yes. What will I do!? Do I make the move, or does he!? I had no idea.

We went into the living room, he put on some music and sat on the couch. I sat next to him and he told me if I wanted to, I can sit closer to him. Of course I moved closer, my hip resting on his. I thought of how my girlfriend used to sit with me, so I went with that. At some point, I had decided that it was his home, he makes the first move. I was too nervous to do so anyway.

There is something about a man, putting his arm around you that makes you feel safe, only that moment matters. His arm was over my shoulder and I was looking at him. He was looking at me, eyes moving up and down my face and body. "You're quite beautiful." He said with gentle smile. Beautiful! I've never been called beautiful before! The feelings were overwhelming! I blushed and said, "You are quite handsome!"

He leaned in, I followed. Our lips met... the feeling was... was amazing! I had no words! I could feel his salt and pepper stubble on my clean shaven face! I adored the feeling!

That kiss lasted for what felt like a lifetime! I put my hand on his chest and the other on his neck. He pulled me close with his arm around my shoulder and his other hand lifted me but my hip and bottom. I was so aroused I couldn't sense anything else but his touch, his lips, the musky smell of his cologne, the increasing tightness of my pants, the growing bulge in his!

My hands were a dizzying mess as I explored his figure. He pulled me into his lap and I could feel his erection through my jeans and his! He feels... he feels amazing!

I got up and startled him. His hands groping my ass while mine cupped his face! I had never felt more attracted and more attractive in my life!

I felt one of his hands go for the buttons on my jeans, the pressure behind then was finally released a little! Then he reached into my pants, under my boxers. I felt his rough, incredibly strong hands grip my firm ass! Then, I felt another new sensation. My cock was oozing, I could feel the slickness of my boxers. Did I cum!? I had never experienced precum before. I stopped him to look, I was embarrassed. He smiled and said, "It's natural baby, your excited. I am too!" I felt a little better but was still unsure.

He asked if I wanted to go to the bedroom. I shook my head yes as I started to get up. Then his strong hands and legs lifted me from the couch with me still in his lap! I was light headed from the list I was experiencing. As we went to his bedroom I found my self thinking, I must have him!

101again
101again
23 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
88girfriend88girfriendover 1 year ago

Good beginning. I like the detail and development. I can't wait to see where you take this.

JgsexyJgsexyalmost 3 years ago

Very nice start. I feel as though I am in this man’s arms on my way to his bed.

101again101againalmost 3 years agoAuthor

Part 2 has been submitted, just waiting now.

MrUnkn0wn13MrUnkn0wn13almost 3 years ago

Just where the story gets interessting

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Popping His Cherry She finally makes him her woman.in Transgender & Crossdressers
The Babysitter Babysitter guy becomes babysitter girl.in Transgender & Crossdressers
A Slut is Born Young man forced to be a womanin Transgender & Crossdressers
The Offer A crossdresser accepts an offer to be a housewife.in Transgender & Crossdressers
Bully's Mom Tricked Me Ch. 01 But she is making me a mindless sissy bitch instead.in Transgender & Crossdressers
More Stories