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An Unexpected Experience During a Doctor's Visit

Some years ago my PCP wanted me to see a urologist so they could check my prostate. Now, I like having my prostate probed/massaged so that did not sound bad to me so I went. I needed a late

Posted by a TS / CD

2

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An Unexpected Connection on the Couch

I usually don't lety daddy mens lick my lil ppclit. My lil tiny shriveled up ppclit does not function like a real daddy mens cocks does. It's only there to serve 2 purposes: to tinkle n

Posted by a TS / CD

By sissyjamie4daddys

0

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A Surprising Hospital Visit in Feminine Clothes

I'm a semi passable crossdresser who wears my fem clothes under my manly clothes. I guess you can say I'm a closeted crossdresser. I am a total bottom sissy, who is very feminine with top

Posted by a TS / CD

By sissyjamie4daddys

0

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A Surprise Lunch Date After Shopping

Met this daddy while shopping. Daddy is an older daddy. Daddy asked me if I wanted to go to lunch with him. "Of course I will daddy" I told him. We walked arm in arm out of the store n into

Posted by a TS / CD

By sissyjamie4daddys

0

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A Surprising Morning with Two New Friends

There is nothing better than waking up with 2 daddy mens laying next to you, one burying his cock in my sissy cunt, while the other daddy mans is face fucking my mouth. I LOVE that. So yesterday I

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Night with Friends

Last night was my first-time with 2 guys! I had no idea it was going to happen, but it was planned by the guy I had hooked up with. This guy and I have been hooking up off and on recently. Messaging

Posted by a TS / CD

0

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A Night Out at the Adult Arcade

I have been with my daddy for 7 years. Daddy has taught me and trained me on how to be a big time whore. Daddy buys me my outfits, my shoes, my makeup, my jewlery, anything that his lil gurl needs or

Posted by a TS / CD

By sissyjamie4daddys

0

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A Morning Encounter at Daddy's Place

I got invited to a daddy mans house this morn for breakfast. Daddy mans told me he was looking for a handy. He told me he woke up with a massive boner n needed some relief. He told me his wifey pooh

Posted by a TS / CD

By sissyjamie4daddys

0

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A Surprising Meeting on a Park Bench

I love me daddy mens that are truly packing. The bigger the better that meat stick is the more I enjoy it. Especially if daddy mens can last a nice long time. Yesterday I met a good looking daddy

Posted by a TS / CD

By sissyjamie4daddys

0

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A Night of Unexpected Encounters in the Garage

I pulled into the open garage door as instructed Turned my car off as the door closed slowly behind Mr I was scared This is the first time I had ventured out dressed I had placed an ad on Craigslist

Posted by a TS / CD

By averageguy2021

0

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A Fun Evening of Poker and Surprises

Last night I went to my buddies house to play poker. My friend said to come early to help him set up. He asked me to dress up in something sexy. I got a new blue dress that was a little short. I also

Posted by a TS / CD

0

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A Unique Birthday Surprise with Friends

My wife and me had been married about 5 years when she found out I love crossdressing and it turned her on so she bought a strap on and used it all the time on me and seeing how I loved it she for my

Posted by a TS / CD

By Deleted User

0

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An Unexpected Encounter at the Bookstore

So last night I stopped at a local adult bookstore bout 8ish. I was all dressed n ready to get down on a cock or 2 or 7. As I parked my car I noticed 2 daddy mens walking out the store. I walked past

Posted by a TS / CD

By sissyjamie4daddys

0

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A Day of Luxury with My Sugar Daddy

One of my sugar daddy mens is in town til Sunday. He has treated me like a queen since he got here late Monday night, n I have treated him like a king. Yesterday, my sugar daddy mans took me on a

Posted by a TS / CD

By sissyjamie4daddys

0

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A Surprising Adventure in a Van

The first time i dressed up was when i was 18 and right out of high school. In those days i had a very slim body and a nice bubble ass. I would go to the adult store and check out the booths and one

Posted by a TS / CD

By QuailIris8603

0

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A Journey Through a Unique Toy Collection

It started off with my now ex wife's toy collection. Yeah, you read that right. My lil sissy gay ass was married to a woman at one time. Get over it, cause I sure the fuck did. Anywho, she had a

Posted by a TS / CD

By sissyjamie4daddys

0

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A Weekend of Fun and Friendship at the Party

Another memorial day weekend is on the books, n this gurl needs some sleep. I have been on the go since Friday morning with no to very lil sleep. But I wouldn't trade it for anything. I drove to

Posted by a TS / CD

By sissyjamie4daddys

0

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A Journey of Self-Discovery in a Hotel Room

young latina crossdresser sissy id like to share one of my first experiences on here. (background) 5’6 130lbs big ass thick thighs & small waist, long hair, i dated a bbc slut & she

Posted by a TS / CD

By portlandpartier

0

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Rediscovering Myself After a Tough Breakup

bbc latina sissy with anxiety. i was triggered into becoming a trap sissy when my ex girlfriend was a bbc size queen cheating slut, i became addicted to watching & cleaning her messes when she

Posted by a TS / CD

By portlandpartier

0

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An Unexpected Evening with Daddy Friends

I invited one of my daddy mens over tonight for some sucky fucky time. We were sitting on the couch kissing n making out, groping each other's bods. Daddy mans had his delish cock out n I was

Posted by a TS / CD

By sissyjamie4daddys

0

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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

H hung4powerbttms “Them boys.” D dombdsm247 “Dominant parent” T trigsex “Mindstretch / Mouth Exercise” D delbert1966g “Cousins on sofa”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Couple Gay Straight for Gay	Letting her desires take over	81.7k	1.0k	4.7k
#2	Tiffanyheels Couple Straight Trans	Excited wife self-pleasure	181.6k	2.5k	4.4k
#3	kimorafoxxsexycd Trans Gay Couple	Fun at the store and with ex friends baby daddy	165.1k	1.7k	3.9k
#4	KestrelElbow9092 Gay Straight Couple	Need to be feminine.	83.9k	722	3.6k
#5	butchmax Gay Straight Straight for Gay	I guess I am what I am	127.5k	850	2.2k
#6	Dedavis Straight for Gay Straight	Hot tub connection, part two	107.8k	733	2.0k
#7	wally4u Gay Couple Trans	Drunk Abs Experience I'll Never 4Get!	74.9k	331	2.0k
#8	sissyjamie4daddys Trans Couple Straight	I love water	87.1k	498	2.0k
#9	Steve Straight Straight for Gay Gay	Vacation with my Aunt part 1	59.5k	689	1.8k
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	88.4k	678	1.7k

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

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