Crossdresser First Time Creampie Stories Stories

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The Retirement Party

by DrLuverotica on Sep 18, 2017
Transsexuals & Crossdressers

April 3 Jo had been singing it for days and it was driving me mad! "It's all about the bass, about the bass..." On and on she went until finally I screamed: "Enough already!" "Oh hubby. Do you not like my song?" "Well, I like the way you move to the song." Jo looked hot swinging her big sexy curvaceous ass in a short micro skirt and flicking it up occasi...

Crossdresser In Picnic Area

by Lovinhose on Sep 13, 2017
Transsexuals & Crossdressers

This is my first attempt at a fictional/fantasy story. All my stories thus far have been true, honest, and accurate, as much so as I can recall. But I kind of ran out of true stories that were worth sharing (for now, but I've got some 'irons in the fire' and hopefully I'll have another true story to share fairly soon). The story I will tell here is something...

Parking Area 2 Miles

by Lovinhose on Sep 15, 2017
Transsexuals & Crossdressers

Prior to writing this next installment in my awesome sex life as a bisexual crossdresser, I thought I had already written about all of my worth while, true life experiences, but I had actually forgotten about this one. It happened in, I believe, 2008, during the end of the summer. I was driving my truck. I am a truck driver by trade. Three hours and a co...

My Secret Revealed Ch. 06

by jealouscuck on Jun 19, 2018
Transsexuals & Crossdressers

I had crossed a line by myself. Here I was at Sally's apartment, not knowing who was there for sure and transformed completely into a passable woman. I had ventured out and found a crossdresser shop on my own. The sales "person", Tammy had not only helped me with shoes and clothing, she had me come back in for a complete makeover before I was to go to Sally'...

Homemade Pie

by DiggerDave on Sep 12, 2017
Fetish

Before I continue with my story I will introduce you to myself. My name is Alan and I am forty three years old. I have been married to Pam for twenty years now and we are both happy with each other. We have never had any children. This year Pam turned forty and still looks great. She has dark brown hair which she cuts short in a bob which curves in to the na...

Crossdresser Evolution Ch. 04

by pantyhigh on Aug 7, 2019
Transgender & Crossdressers

Recap - Crossdresser Evolution - Ch 01 - How I got started crossdressing I was becoming addicted to masturbating while wearing panties. I could feel the arousal but at the same time was ashamed that I was wearing my wife's panties knowing that I would soon be cumming in them. There was this part of me that was telling me, "I CAN'T like this," but there was...

Michele Nylons' True Stories

by MicheleNylons on Jul 14, 2020
Transgender & Crossdressers

Introduction For those of you who only read fiction I suggest that you go directly to my autobiographical sex stories contained later on in this essay; but what I thought I would like to do is to take a break form my usual 'physically forced' and 'caught with consequences' Transvestite sex stories and write some of my musings about Transvestism and share wi...

Sissy's Subservience to Wife Ch. 01

by JessicaSIssyGurl on Aug 1, 2018
Transsexuals & Crossdressers

Every Friday evening is my grooming ritual, shaving away every inch of body hair that has cropped up through the week, soaking myself in a bathtub to further soften my skin, red nail polish on my fingernails and toes and finally cocoa butter lathered all over before I sleep that is a thing I do every night though. But before sleeping I message my date for to...

Life and Time of Lady Vargos Ch. 01

by rik581 on Oct 3, 2018
Transsexuals & Crossdressers

I am in the process of reposting my stories. *** "The Life and Times of Lady Vargos" is the second book of the Martin Hastings adventures into a life of forced feminization. This story follows the feminization and marriage of a reluctant young man as he is forced to accept his fate as a male/bride, in a same sex marriage, arranged by his family. This stor...

Literotica Monthly Awards 2020: May

by Literotica on Jul 15, 2020
Romance

Manu and I would like to thank all the authors who submitted during the month, and all the other months for that matter! We've tallied the reader's votes, and are happy to announce the winners of May's Reader's Choice Awards. First Place ($150 Cash Prize Winner):'Twas The Night Before... Ch. 02 by BrokenSpokesSecond Place ($100 Cash Prize Winner):Succubus A...