Birth of a Slut Pt. 01

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My start at becoming a cross dressing slut.
840 words
4.21
36k
20

Part 1 of the 6 part series

Updated 06/10/2023
Created 08/21/2020
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Recently I decided to share my story of how I became a cross dressing slut. While always turned on by stockings and heels my first real chance came after I turned 18 and went to my first adult costume party. A little more about myself. At 18 I was 5'11", 175. I had long hair which was the style of the day cut in a shag. My cock is small, 5 inches but I have been told my legs are fabulous! My grandmother had passed away on my birthday and she had two adult adapted children living with her, Denny and Eileen. They were brother and sister of two alcoholic parents and alcoholics themselves. Denny was 26 and Eileen 24.

After my grandmother passed they moved in with us. Denny drove a taxi and Eileen worked at a dress making company. The typical routine was Denny worked and come home Friday and Saturday nights drunk, go upstairs and pass out. Eileen was shy. She was tall, 5'9" and skinny. She was flat chested but had great legs. She also had her hair in a shag. At 18 I was confused because as much as I was turned on by women, I wanted to suck a cock like I saw in a porno movie.

After a month of them living there I noticed a routine. My family owned a restaurant and bar. From Friday morning till Sunday night the house was empty as my parents slept in an apartment in the bar. Denny would get home around 8, drunk. Eileen would already be home, working on a six pack. Denny would stumble up the stairs and a few minutes later Eileen would announce she was changing for bed. We had three bedrooms upstairs, one for each of us. One Friday night I came home early and fell asleep. Me and my friends had been drinking and I crashed.

I heard a noise and I saw Eileen in the hallway. She was dressed in a nightie top, granny panties, and pantyhose. But she was going into Denny's room. She was stumbling as she was drunk and she didn't fully close the door. Being curious I waited to see if she came out and when she didn't I heard moans from Denny! I peaked in and she was sucking his cock while playing with herself! She knew what she was doing and soon pulled her head back as Denny shot a big load. I could see her cumming as her hand moved furiously in her panties.

As she started to get up I went back into my room and jerked off. I then went down stairs and Eileen was on the couch, watching tv. She saw me look funny at her and I told her she had snot or something on her face...it was cum. She wiped it up and turned red. For the next few weeks I realized this was her fun. Then she found a girlfriend who she hung out with on the weekends. Denny would come home and crash but Eileen came home much later, around 11 or so. At this point I wanted to be Eileen.

I used to swim and got a friend to help me use Nair on my entire body so I was hairless as most swimmers were. Then Friday night before Denny got home I borrowed Eileen's nightie, pantyhose, and panties. I dressed, had a few beers for courage, and after Denny went to bed, I waited a good 20 minutes till I heard him snoring. I then went into his room. He was out cold in a drunken stupor, naked, his cock thick and juicy looking. Scared But horny I slowly knelt on the bed and started to lick his cock. Since I had only practiced on a banana before I was surprised how thick and long his cock got as I worked it.

His cock hard was 8 inches long and thick. I had it in my mouth when I felt his hands on my head and he started to hold me as he fucked my mouth. Scared of what he might do to me if he realized I wasn't Eileen I used my tongue and tried not to gag. After a good fifteen minutes he came, shooting a thick, slimy load of cum down my throat. He then released my head and passed out. I crept out of the room and into mine to change. I had shot a load without being touched! I hid the panties and pantyhose and put her nightie back. About an hour later she came home and did her routine.

I went upstairs and waited till she sneaked into his room. She was drunker than usual and the door was half open. She was working on his cock but it stayed limp. Denny awoke and said something and then Eileen left and went into her room. Again the door was partially open and she rubbed her cunt hard till she came and passed out.

End part 1

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7 Comments
AnonymousAnonymousabout 1 year ago
New Sissy

I dont know how or why i started to cross dress.But here i am now with a womans body complete with size 36d breast.I find my self fully made up and dressed full time I feel so sexy and hot when dressed.I found a park were cross dressers and men and women go for sex of all kinds.I feel right at home here with a hard cock in my ass and mouth at the same time.But i fully in joy my new found love of big black cocks.They fill my ass and mouth with their size.And to add to that all the loads of sweet cum they fill me with.

Microskirt69Microskirt69over 3 years ago
Im Sorry

I apologize for criticizing, but ive had some borderline abusive relationships involving Excessive drug and alcohol use.

So forgive me please!

I look forward to your stories where you can be your girly self with a sexy man who:

A) knows who he is fucking and

B) appreciates you for YOU

Alison

NjcdslutginaNjcdslutginaover 3 years agoAuthor
To Micro

Sorry if this story bothers you. It is a true story and the truth is not always a happy tale.

Microskirt69Microskirt69over 3 years ago
A very sad scene

About Denny:

‘ i waited until he was snoring...he was passed out in a drunken stupor and naked’ And ‘he released my head and passed out’

About eileen :

‘She was stumbling because she was drunk’ and ‘i told her she had snot or something on her face’

This is sad - everything in this story describes completely dysfunctional relationships and suggests severe alcoholism for all characters.

Sexy? Not at all!

So Hot!? No way!

A cute story? Are you kidding?

I hope this sissy gets help because life can be WAY BETTER !

Claudia69Claudia69over 3 years ago
Cute Story!!

Great way to get started....

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