Exploring My Feelings Ch. 01

Story Info
My first time exploring my feelings about men.
860 words
3.96
12.4k
4

Part 1 of the 3 part series

Updated 06/09/2023
Created 06/16/2018
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

I was in my second year of college when I first realized that I was curious about men. Ok, so let me go back a bit. I have always been a man's man, and played sports in High School, including football, baseball, etc. But one night when I was in 12th grade (18 yo) and I was staying overnight at a friends house. They had me stay in his sisters room. She was a year older than us and extremely cute. So there I am in this girly room, with frilly sheets and all the pretty things that a girl would have. So I realized that they felt nice and comfy. So I got this thought in my head and was curious about his sister's bra size. So I slowly got up and went to her chest of drawers and pulled them open to find a bra. The night light gave plenty of light. I found a very nice lace bra and she was 34B. So I noticed that she had panties in that drawer also. So I picked them up and realized that they were purple thong panties. Ok, so this was quite exciting. I then wondered what it felt like to wear a thong, as I had no idea but thought that they were very sexy. So I put on the panties. I of course had a big bulge and then realized that I should tuck my cock between my legs. I looked at myself in the mirror with the glow from the night light and WOW I got turned on to see the way that the thong looked on me. Of course I had a huge bush of pubic hair (way before manscaping).

I started to rub myself in the panties and realized that I was going to cum and could not cum in her panties as I might be found out. So I took off the thong and put it back in the drawer with the bra. I made my way to the bathroom that was attached to her bedroom and decided that I would quietly master-bate on the toilet so that I could have some relief. So I sat down and leaned back and got some toilet paper for my load. I started stroking and realized that she had a clothing hamper in the bathroom. So I stuck my hand down in there and pulled out some clothes, until I found a pair of black lace panties. I was so excited. I put on the panties and started stroking. My theory was that I could cum on/in these and throw them back in the laundry and no one would be the wiser. So I started to stroke myself through the panties and in about 30 seconds I shot a huge load all in the panties and all over myself. I still had to use toilet paper to clean up. When I had finished I put the panties back in the hamper, at the bottom, put on my boxers and got back in bed.

I was a bit excited and shocked that I had done what I did, but that was when I realized I kind of like panties, and lingerie.

So fast forward back to my second year of college. I had a gym class that was in the late morning. I was always in a hurry to get showered and to the next class. However, I was running very late one day, and was not in a hurry because my next class was cancelled. So I got to the locker room late and to the showers late.

So I go to the showers and there is another student in the showers still, a black guy I recognized from the class. I said hello and started to shower, I kind of thought he would be out of the shower before too long because he was soaped up when I walked in. But he just kept showering, and staring at me. After awhile I realized that he was stroking himself slowly and had a semi hard cock, which was quite large. my head started to race and I was trying to understand what was going on. It finally hit me that this was a gay guy and he was liking what he saw. I got embarrassed, and I felt a tingle in my cock as well, which shocked me. I was standing with my back to the wall, he was on the other wall, and as I rinsed off I could see him stroking his big cock. I started to get an erection myself, which really freaked me out. I quickly finished showering, got dressed and left.

I was not sure why I had these feelings. I still liked to wear panties when I could get away with it, but had never thought about being with a guy. That all changed that day as I realized that wearing panties and lingerie was my desire to be the femme in the relationship and give myself to a man. I didn't fully understand this yet, but this was "that" moment where I had to start dealing with it.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
3 Comments
AnonymousAnonymousabout 3 years ago
About Time

After cross dressing and playing with my self it was time to out my self.I knew sex with a strange man or men would not be easy.I have never had sex with a man before.So i went on line and met a man who said he would to met me.He told met wear he lived and to dress and come over.I did my hair make up black corset thong stockings heels tight dress.I was met at the door by a older black man not bad looking .We talked and had a drink or two.He grabbed my head with his hands and kissed me on my red lips.He started to feel me up and pulled out his cock.It was a monster eight inch hard shinny cock.He pushed my head down on his cock.It filled my mouth hit the back of my throat and down it went After sucking he layed me on my belly and filled my ass with his cock.

AnonymousAnonymousalmost 6 years ago
It happened to me

Liked the story. The best part of it was when he go's in the bedroom and finds the girls lingerie and can't stop himself from trying it on

This is what happened to me when I was in my early teens and I went into my sisters room while I was home alone and found her petticoats hanging in her closet.

I remember that there was 3 of them

One was pink one was sky blue and the last one was yellow.

I took them out of her closet and went into the bathroom where I removed my clothes and put all three petticoats on in sequence .

I couldn't believe how pretty and feminine that I felt as I looked at myself in the bathroom mirror and my penis was extremely hard and I couldn't stop myself from jerking off looking at myself dressed up as a girl

It was the day that I became a crossdresser and I've been one ever since.

Of course I've got my own feminine clothes now and I dress en.femme as often as I can but I still remember the thrill of wearing my sisters petticoats and making me want to crossdress from that time on

DeborahAnneDeborahAnnealmost 6 years ago
Wearing feminine articles

As I am reading this I have on Nylons thigh highs, pink panties, and a Jane Seymoure dress in white with an attached slip, a bra, and a duster I just bought from Pink Lily, I feel so pretty the only thing I miss now is having a man here to give pleasure too.I love reading the stories on here and lick the pre cum off my cock. da.cd@frontier.com

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Tonisshy gets Southern Hospitality Toni meets a real southern gentleman.in Transgender & Crossdressers
Mike A gentle, but unloved husband, is discovered by Mike.in Transgender & Crossdressers
Dream Girl Pt. 01 Get the girl... or become a girl for BBC.in Transgender & Crossdressers
The Live-in Landlord Pt. 01 Charlie finds himself changing for his Landlord.in Transgender & Crossdressers
The Agency Mike finds a job, which may be much more than he expected.in Transgender & Crossdressers
More Stories