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Category: TS / CD

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A Special Birthday Surprise for a New Friend

Being very discrete playing around while cross dressed was good for me. I love the feel and eventually grew into wanting the real thing of a man to fuck me. I had played with dildos for years of

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A Crossdressing Encounter in a Hotel Room

Older man here now and I have been cross dressing for years. Mostly as I traveled for work out of town. Eventually that worked into going to book stores. I would get dressed in the booths and play

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A Surprising Late Night Massage Experience

I’m a reguar guy 90% of the time, but ever since I was a kid, I loved wearing pantyhose. By the time I was in high school, I had my own stash, which exists to this day with new pairs replacing

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A Chance Meeting at the Gas Station

So this just happened. I had to stop at the gas station a few blocks away from my house. I had just left the club n I was dressed wearing a hot lil red dress. This car pulled up next to me with a

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Visit to Daddy's Place

Talked to an older daddy who was looking for a gurl to come over n relieve him of a 4 day backup. We exchanged pics n daddy invited me to his place. I put on my hot lil pink mini skirt, a black

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By sissyjamie4daddys

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An Unexpected Invitation to a Couple's Home

I responded to a M/M couples post that was looking for a 3some with a bottom. After a few exchanges, they invited me over to their place. James is in his mid 50s n Mark in his late 30s. James is a

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By sissyjamie4daddys

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An Unexpected Connection at the Club

Saturday night I went on a cock hunting expedition at 1 of my local clubs. I have never been disappointed at this club. Usually I find some nice older daddys to suck off in the bathrooms. Saturday

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By sissyjamie4daddys

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An Unexpected Night at the Local Bar

So a couple days ago I was very very horny and needed sucky ducky time.. I got all gussied up in my shortest shorts and a very short belly shirt.. thigh high lace topped stockings lacy garter and

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A Surprise Visit from the Maintenance Man

My maintenance man saw me.... I left my side window blinds slightly open. I knew he was coming over so I got dressed in some sexy lingerie, I was looking great. Heard the blower going towards the

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Unexpected Flirtation at the Big Box Store

This happened a few years ago, I worked part time at one of the big box stores after I had retired. I am considered a pretty good looking guy and I get along with most people. We had this one regular

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An Unexpected Encounter at the Club

I met an older daddy last night at a club. I was wearing a very short revealing lil black mini skirt that showed off my ass pussy. Daddy asked me to follow him to the bathroom. When we got there,

Posted by a TS / CD

By sissyjamie4daddys

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A Nervous Visit to the Adult Store

So my story starts when I lived with my girlfriend. I used to take some of her clothes and lingerie. We had separated from each other. We got into a fight. She had gone to her parents house. I was

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Exploring Connections at Local Bookstores

I started sucking dick when I was a younger bi man. Now that I have come out fully dressed as a crossdressing sissy, I am sucking more dick daily, at least 2-4 a day. I love humming, slobbing,

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By sissyjamie4daddys

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A Rainy Night Hotel Adventure with a Friend

About 10 years ago I went to a football game with a friend out of town we left in a hurry and forgot the bags with our clothes . Didn't realize it till we got to the hotel and it was really no

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An Unexpected Visit from My Sugar Daddy

Last night, I got a call from a local sugar daddy who told me to be ready by 700pm that he was stopping by. Daddy told me he had something he needed to drop off. I got all dressed up, makeup, n

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By sissyjamie4daddys

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A Poker Game Leads to Unexpected Encounters

I am very sub and very sissy minded.. I am very very passable.. my daddy hubby is very voyeuristic.. he is so erotic and has the most magnificent cock that has ever stretched my pussy.. not only dose

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An Unexpected Meeting by the Water

Hi live in the SB area and went up to a place called Kenwood the other day looking for cock one guy motioned me to meet him down by the steam and so I followed him down and he leads me to this spot

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By Deleted User

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An Unexpected Visit from a Charming Daddy

Last night, I was cruising thru some sites looking for some older lonely daddy that could use some company. I got a hit on AFF from a good looking 60ish top daddy that was looking for a gurl like me

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By sissyjamie4daddys

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Journey of a Female Impersonator: Embracing Life

When I came out, I CAME OUT!! My fam freaked out big time. Some fam were shocked, same fam n friends were like it's bout time, sheesh. It went from if your father knew he would roll over in his

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By sissyjamie4daddys

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An Unexpected Ride in a New Town

Ounce when I was very young I was skipping school my first day at a new school while walking home I wasn't sure where I was a new town new school but while trying to find the road that led out

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By Deleted User

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Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

RISING AUTHORS ON DOUBLELIST See all

J Jody2u “Her husband- His partner” L leeise6969 “Guy I met off of here” C charles63 “Just had to try it” B bottomtray “Getting used at theater”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Straight for Gay Couple Straight	I couldnt refuse the temptation.	51.2k	748	4.3k	↘
#2	Tiffanyheels Straight Couple Trans	Finally had intimacy with ex mother in law	102.6k	1.7k	3.4k	↘
#3	KestrelElbow9092 Gay Couple Straight	A First for Me.	38.2k	447	3.2k	↗
#4	kimorafoxxsexycd Gay Couple Straight	Saucy playful fun	105.0k	1.3k	3.1k	↘
#5	cnysub Gay Trans Straight	Deep Kissing	65.0k	633	3.1k	↗
#6	sissyjamie4daddys Trans Couple Straight	I love water	62.2k	473	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Night At The Anvil... Part 1	58.4k	279	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	52.2k	632	1.7k	↘
#9	powers8 Straight for Gay Straight Gay	A great customer	56.1k	523	1.4k	↘
#10	butchmax Straight for Gay Couple Straight	What happened to BI	61.9k	487	1.3k	↘

Page 1 of 50 · Showing 1–10 of 500 authors

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