tagTranssexuals & CrossdressersHe Brought Me Panties

He Brought Me Panties

byCute Little Thing©

Ok, here's a quick story and true at that. I was away on business one night and surfing for sex on Craigslist. The title of my post was "If I'm so strait then why do I want to get fucked like a girl?" It was a popular post and I got a bunch of replies, and a bunch of men wanted to fuck me. This made sense and I wasn't that surprised. I'm on the small side, 5'6, 135 lbs, young (28), and considered pretty good looking. I'd just broken up with a girlfriend and I'd decided I'd finally give in to my urges and try the sissy faggot thing for a few months.

After many advances, I ended up going with someone a little older and little less hot than the others because he had the ingenuity to ask what my fantasy was and actually asked me what I wanted to do that night. There was another guy in the running but he had this obsession with sticking a big dildo up my ass. No matter what we emailed about he kept working back to that.

Anyway, I told him this man my fantasy was to actually be the girl, and I was hoping he could help me with it. That was about all the information I gave him. He was into it, and said he'd stop by the drug store on the way over and by me a pair of panties. He also promised to only call me by my girl name Veronica.

About 1/2 hour later he showed up at my hotel. I opened the door and he came in. He was taller than me which was nice (but not toweringly so) and probably around 45, not particularly good looking but not ugly either. Mostly, and this was important, he was masculine and virile and seemed to want to take control. It was a little awkward for a second but then I thought "fuck it", and just pulled off my shirt and bit my lip. I guess I was nervous that he wouldn't find me attractive enough.

Instead he smiled broadly and said 'Veronica'. That gave me a sudden thrill that I hadn't expected. He pulled out a pair of pink, boy-short, panties from his pocket. They were cute if a little cheap looking. The kind of thing a college girl would wear. Slutty, but still a little girly and innocent. I was glad they didn't have any lace on them. Actually I was delighted to finally be getting a chance to do this.

I dropped my pants. I was wearing a jockstrap since that was going to be my "panties" if he hadn't come through with. In another second I took those off too and just stood there for a second. I was completely naked and he was fully clothed. He even had cowboy boots. My dick felt really small and girly and I liked that about it. I felt vulnerable, and girly, and naked, and exposed, and I like the way it felt.

In a second I had wriggled into the panties. How crazy. There I was, a total sissy faggot in girly panties my man had just bought for me. My little dick was getting hard and I wanted to turn him on too.

I sat on the bed and wrapped my legs around his waist. Sitting there I could look up at him and feel submissive. I could feel his dick getting bigger beneath his jeans and I wanted to feel more of it. I unbuttoned him revealing his tight cotton briefs, his big cock about half hard making a shape in the fabric. I pressed my lips to it and ran my mouth up and down his shaft through the fabric. This was good, but I wanted to feel girlier so I turned around and climbed onto the bed sticking my cute little ass in the air.

He took the hint and started to squeeze my ass cheeks, running his hands between my legs to stroke my little clit through the fabric. He pulled the waistband of my panties down so that my bare ass was exposed and slapped me a few times. I heard him say

"That's a pretty little cunt baby." And I replied that I wanted to feel his dick against me. He pressed his hard cock against my asshole, my boy pussy and I could feel him dry fucking me through the fabric of his underwear. I knew what I wanted. I felt like a little bitch and he was treating me that way, and I liked it.

In a minute or so I dropped to my knees. I noticed how hot I felt to be there, practically naked, with only a pair of pink girl's panties on, and with my ass exposed at that, and him, this strange man standing there fully dressed with the exception that his fly was undone. What a power dynamic. I had ceded all my masculinity to him and now I wanted to make him cum.

I looked up at him with my sweet pretty eyes and asked permission to pull his underwear down. I took out his big cock and looked at it, meaty and full, shaved, big, powerful, manly. I kissed it. How about that? I guess I waited too long, I was too much of a tease because I felt his hand grab my blond hair and pull my head back. My neck stretched and my mouth opened and he shoved his big mushroom head into my mouth.

I looked up into his eyes with that dick in my mouth, suddenly all girl, suddenly full Veronica, and he started fucking my mouth until I gagged. He stopped and pulled out and asked if I was ok, but I just smiled and asked for more. He pressed his big ball sack against my mouth and told me to lick. I liked him like a little cunt. Like a little sorority girl who wanted to please the college quarterback. All the time he jacked his big cock.

"Suck my balls you little cunt bitch" he said "suck them you fucking faggot." And I licked. I was getting really hot now and started jacking off. "Yeah, you like playing with your little pussy, don't you girl. Tell me you like it."

I didn't answer, just pressed my face into the crack between his legs and licked his asshole while he jacked off.

"Yeah girl, yeah sissy, I'm gonna cum." He yelled as he jacked his big cock inches from me face. "Cum with me you little cunt." He pulled my head back away from him with one hand and jacked his huge cock just inches from my face with the other. I was playing with myself furiously now and didn't know how long I was going to last.

"Here I cum bitch, here I cum." He yelled and shot huge fucking ropes of cum all over my face soaking me like one of those sluts from a porno movie. I loved it, and as his cum hit my face I felt myself shooting my little boy clit all over the carpet.

Five minutes later it was all over. I'd swallowed whatever cum had landed in my mouth and wiped up and eaten the rest with my finger. I sucked him clean and got him dressed. He spanked me on the bottom like a good girl and left. On his way out he said "you can keep the panties."

I guess they're my souvenir.

I like getting email and feedback, so please write if you have half the inclination.

Report Story

byCute Little Thing© 11 comments/ 104343 views/ 14 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartfrind, purpletie22 and 12 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

There are no recent comments (11 older comments) - Click here to add a comment to this story or Show more comments or Read All User Comments (11)

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: