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sissyjamie4u

17 stories  ·  0 listens

All (17) TS / CD (13) Straight (2) Gay (1) Straight for Gay (1)
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An Unexpected All-Male Baby Shower Gathering
I got invited to an all male baby shower, aka bukkake party, last weekend. I was the center of attention as 7 daddys surrounded me, each with their hard cocks out n jacking their cocks. I begged each

Posted by a TS / CD

By sissyjamie4u

A Chance Encounter at the Coffee Shop
I have a thing, a fetish, a preference, whatever you eant to call it, for older top men. The older, the better. I'm a 51 year old crossdressing bottom sissy. My 1st sexual encounter with a man

Posted by a couple

By sissyjamie4u

Regular Visits to a Unique Friend
For the past 8 months I have been visiting this sweet little crossdressing sissy who knows how to take a pounding. She sucks my dick like a hoover. And her ass is even better. I stop by her house 2x

Posted by a straight man

By sissyjamie4u

A Journey of Transformation in a Unique Marriage
I am so proud of my sissy husband. I have turned him into a confident, proud little gurl, who craves men as much as I do. We have been married for 6 years now and he is now a she. When we first

Posted by a straight woman

By sissyjamie4u

A Surprise Visit to a Young Stud's Place
I decided to pamper myself last Saturday. Took a bath, shaved my legs, and the rest of my body, then to the nail salon for a manipedi, then shopping for a new outfit, and new shoes. I get a text from

Posted by a TS / CD

By sissyjamie4u

An Unexpected Encounter on the Couch
I hooked up with a young stud last week. We exchanged pics, and texts. He had what I wanted; a nice thicky thick cock that looked delish. I gave him my addy, and he was at our house in 30 minutes.

Posted by a TS / CD

By sissyjamie4u

Embracing My True Self: A Personal Journey
Where to begin? Hmm let's see. All those years wasted on being a straight white male, marrying a woman, having 2 children, and yet, not happy. Then, becoming the fem I am today. Why did I wait

Posted by a TS / CD

By sissyjamie4u

An Unexpected Encounter at the Hotel
I am a sissy, bottom crossdresser, who loves worshipping alpha top men. I live my life as a fem 24-7-365. I do what the wife or girlfriend won't do. Last week, I met a small group of men, 4

Posted by a TS / CD

By sissyjamie4u

A Surprise Cabin Getaway with Friends
So I get a text from a young stud that I have hooked up with several times. He is 26 years old, nice bod, great cock with lots of stamina, and is a multiple heavy cummer. He has a 4 day lil vacay, as

Posted by a TS / CD

By sissyjamie4u

A Night of Unexpected Connections at a Party
I am a full time crossdresser. 24/7/365 I can be found wearing fem clothes. Dresses, mini skirts, blouses, heels, stockings, make up, wigs, the entire ensemble. I am ALL fem, a sissy, a total bottom.

Posted by a TS / CD

By sissyjamie4u

A Unique Encounter Between Two Lonely Hearts
The ad read: 73 year old lonely widower seeks 1st time with a crossdresser. Me, being a bottom crossdresser who loves older men, responded to his post. After a few emails, and texts, he invited me

Posted by a TS / CD

By sissyjamie4u

A Crossdresser's Journey to Find Pleasure
What is it that men don't understand? I'm very specific in my posts. I am a crossdresser, who bottoms ONLY! I do not top. I don't want my lil pp clit licked, kissed, touched or in your

Posted by a TS / CD

By sissyjamie4u

Exploring Life with an Older Partner
I used to date a much older daddy that loved sharing me with his friends. Daddy turned me into a cock crazy cock loving sissy. Daddy was the 1st man I had ever been with. I lived with daddy for a lil

Posted by a TS / CD

By sissyjamie4u