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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Night of Surprises at the Gender Swap Party

The woman I was dating wanted to switch genders for a party promised wild sex. I would go as female her as male. So I go to a neighbor who did make up in Hollywood. She made me as feminine as she

Posted by a TS / CD

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A Special Reunion in a Hotel Room

I'm an older CD. I'm in my 70's now. I have dressed for many years. I love sucking cocks and bottom for hard one. I was doing one of my nights in a hotel room. I usually post an ad

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By OlderMaleguy

0

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An Unexpected Night with Roommates and Friends

Well I decided to get a room and invite guys over to fuck me I got all dressed up looking good then this guy shows up and he gets undressed and I begin sucking his cock when someone knocks on the

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A Journey of Self-Discovery and Acceptance

I am a crotch goblin, a cock gobbler, a cum guzzler. I love sitting on daddy mens laps n bouncing up n down on their cock, wiggling n shaking my moneymaker, cock buried balls deep in my sissy cunt. I

Posted by a TS / CD

By sissyjamie4daddys

0

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Flirty Encounter at the Nail Salon

I had a nail appointment yesterday to get my monthly mani pedi at a local nail salon. There was 3 other women, n a younger stud getting their nails done. Young stud started hitting me up. He was good

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By sissyjamie4daddys

0

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An Unexpected Visit Turns Into a Surprise

so im bi and my wife knows and always said just be safe and that she didn't want to know but about any of it but the other day i was off work and happen to have one of my local big dick older

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A Night Out in the City: Unexpected Encounters

When I meet with a top daddy, or go to a sex shop that has booths n theater, or to the club to hook up, I ALWAYS dress like the true slut I am. Short, lil mini skirt, no pantys, that shows off my ass

Posted by a TS / CD

By sissyjamie4daddys

0

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A Night to Remember at the Housewarming Party

My body is hurting this morn. My mouth n jaws are sore, my hair is sore, my tittys hurt like hell n they have bite marks all over them, n my sissy pussy is raw n sore. Last night is kinda a blur, a

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Visit from the Neighbor

Today I woke up thinking I had to go to work. I got up and jumped in the shower. When I was in the shower I told myself that I had to clean my house and wash clothes. I was in my room getting ready.

Posted by a TS / CD

2

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A Night of Unexpected Encounters at the Theater

Short story, I'm a mature sissy cd bottom and recently took a chance and went to a xxx/adult theater place in town. I wore a tank top and mini skirt to drive there and enter. Once inside and I

Posted by a TS / CD

0

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Unexpected Meeting During a Shopping Trip

I was out shopping yesterday n met a very nice, well built black daddy mans. OMG, he was fine as fuck! Muscular, big wide chest n shoulders, nice ass, I just wanted to lick n eat him up. I was

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By sissyjamie4daddys

0

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An Unexpected Meeting in a Dark Hallway

It was in a dark pasageway between two xxxmovie video rooms in an adultXXXtheater in my town where I accidentally got fucked. I was wearing only a nightie and thigh highs. I was the only cross

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An Unexpected Encounter at a Party

So I walked out to the kitchen and then to the back yard. I was so loving the cool air hitting my ass. I turned around when I noticed my ex wife's sister in law at this party. I was so afraid

Posted by a TS / CD

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A Transformative Evening of Makeup and Friendship

I told you about this past weekend. I went over to my friend's daughter's house this past Tuesday evening. We were going to hang out this evening. I took my bag of sexy clothes and

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An Unexpected Visit to a Friend's House

So last weekend I went over to my friend's house for some fun. It was a beautiful morning. We were having a great time in his back patio. His daughter showed up and caught us having fun. She

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0

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Unexpected Encounters at the Motel

I decide to get a motel room in a city about 50 miles from where I live. I post semi-passable sub bottom 50's looking for tops, I don't put any age size or shape just be a top. I get the

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A Night of Intimacy and Connection

Daddy Tom held me close n started kissing me as he groped my tittys. He buried his face in my tittys n licked them all over. "God dayummm I love a big titted gurl" he told me. "Tig ol

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Meeting at the Adult Bookstore

I love to be spit roasted, love n enjoy being double stuffed in my sissy cunt or having my mouth pumped by 2 cocks. The more the merrier is my motto. N bigger is ALWAYS better. Yesterday I stopped

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By sissyjamie4daddys

0

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An Unexpected Gathering at the Baby Shower

I was invited to a baby shower Saturday at a daddy mans house. Daddy mans told me that he has 4 friends that would be there, n to wear something slutty. Sweetie: that describes every piece of

Posted by a TS / CD

By sissyjamie4daddys

0

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An Evening of Surprises at a Friend's House

Story part 2. I was talking my friend's dildo. She kept going deeper and deeper that I was moaning and crying. I didn't want her to stop. She tells me that she wants to see me come from my

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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

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	77.3k	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	525	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	73.6k	1.1k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.7k	457	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	51.6k	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	32.6k	319	1.1k	↘

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

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