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Transgender Sex Stories – Real Encounters & Passionate Experiences

Welcome to DoubleList’s collection for trans sex stories, where our users share their real, salacious experiences. Your secret encounters are always safe with us because your identity will be 100% anonymous. So, come on in and add your steamy trans erotic stories; we can’t wait to hear them.

Category: TS / CD

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A Surprising Encounter at the Rest Area

I need more 3 I had only been to the rest area by the boat ramp once but it had been such a hot experience I wanted to go back, but I was not sure what to do when I got there. I was wearing some

Posted by a TS / CD

2

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An Unexpected Encounter at the Park

I need more part 2 As I knealt and sucked my breastfeeding friend he started to moan and his cock got harder and swelled. I ran my lips up and down it length and ran my tongue around its head and

Posted by a TS / CD

0

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An Unexpected Connection at the Trans Club

I had stopped at my local trans club a few nights ago for a lil drinky pooh. It was not really packed, maybe 30-35 peeps. I sat at a table n ordered my drinky pooh. The lil twink server brought me

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Encounter in a Truck

Part 2 of my first time. I walked out of the booth. My ass just got fucked for the first time. I was looking forward to getting fucked hard again. I got in another booth and right away this guy came

Posted by a TS / CD

0

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A Journey of Self-Discovery and Expression

I was married to my wife for seven years. I used to take some of her sexy clothes and lingerie and high heels and makeup. My wife went to a party with her family. I was sick with a fever and a cold.

Posted by a TS / CD

0

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A Night of Fun at Daddy's Party

I just got home from pulling an all nighter with 7 young studs. Cum is still leaking out of my sissy cunt n my jaws are sore. But I loved every second of every minute of every hour. I can still taste

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Encounter at the Boat Ramp

I had met a guy on DL and corresponded with him for a while. He wanted pictures of me and I had sent some and it turned out he had a breast thing and I have nice breasts (38 C or 40B) so I sent him

Posted by a TS / CD

0

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A Weekend Getaway with My Sugar Daddy

So last week one of my sugar daddy mens invited me to his house. His lil wifey-pooh was going to visit fam for a few weeks n daddy mans needed my company. Daddy mans lives in NC n he gave me a nice

Posted by a TS / CD

By sissyjamie4daddys

0

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A Playful Encounter in the Bathroom

I'll start by saying that me and my partner who i met on here are close and have a very strong understanding of each other and that our kink play is both safe and consensual. Im 25 trans pre

Posted by a TS / CD

0

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A Chance Meeting at Starbucks During a Wait

I had to take my car in to the shop for an oil change. There were a few peeps a head of me n the car guy told me it would be bout 1.5-2 hour wait see before they could get my car in. Thank goodness

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Reunion with My Old Teacher

I was cruising the ads on a few diff sites n replied to a few that were posted by older daddy mens. I have a major fetish for older daddy mens. They make me weak in the knees n I will do anything for

Posted by a TS / CD

By sissyjamie4daddys

0

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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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Top Authors

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

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Mouth4You “First time sucking penis” S samwhycantwe “Intentional intimacy” C caniuseu “First time shed intimacy”

John Lee Erwin I am He-Man “Chick with appendage picks me to lick her appendage.”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.6k	631	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	77.4k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.6k	354	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	47.2k	526	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	73.7k	1.1k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.8k	457	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	51.7k	273	1.8k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	48.9k	605	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.1k	358	1.2k	↘
#10	powers8 Straight Gay Straight for Gay	Back with Michelle and Lisa	32.8k	319	1.1k	↘

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