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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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A Surprise Visit from a Contractor

I was working at a big box store part-time a few years ago. One of the black contractors seemed to take a liking to me and being as I am Bi, I encouraged him. One weekend my wife went out of town to

Posted by a TS / CD

By Deleted User

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A Surprise Meeting at the Store

Part 2. He was in his underwear sitting down. I got between his legs and was giving him a blow job. I got out a condom and with my mouth I slid it on him. I took off my g string panties and lifted my

Posted by a TS / CD

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Getting Ready for a Night Out with Friends

The other night I was chatting with one of my transgender friends. She was going out with one of her guy friends to dinner. I didn't have any plans to go out. It was still early and the sun was

Posted by a TS / CD

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Unexpected Encounters at a Rest Area

I love sucking dick in public. In a car, a park, a parking lot, a public bathroom. It's such a high for me. There's a rest area bout 30 minutes from my house on a busy hiway. I'll go

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Encounter in the Neighborhood

I got a txt from an Blk man who is a real prick who lives around the block saying I gotta serve 2. He slapped me last time because I couldn't swallow all his nutt because there was a lot. But

Posted by a TS / CD

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A Late Night Encounter at the Motel

I was high as fuck and lonely. My body was swollen and horny in a motel on LA Cienega. I put out the word on kik that I needed a Big veiny Black Cock: "5/22 - Any blk men bored or horny tonight,

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Unexpected Late Night Visit from Neighbors

Shemales First 3Some Now I've done it. OMFG! First time with TWO men! Feel Nasty, gross and my ass is numb & hurts at the same time. Surprised that my body and mouth could get two men SO

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Exploring Connections at the Adult Bookstores

I'm a trans whore. My legs are ALWAYS open n spread for any daddy that needs a place to put his dick. Old men, young men, delish Black Men, n white men are my faves. I love getting on all 4s,

Posted by a TS / CD

By sissyjamie4daddys

1

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A Weekend Adventure at the Hotel Next Door

Last weekend I rented a room at this hotel next door to this adult book and video store. It wasn't a big name hotel. In back of the store was a lot of prostitution going on. I got dressed up in

Posted by a TS / CD

1

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A Playful Encounter on Laundry Day

I was doing laundry and house cleaning. I was wearing a French Maid outfit with black stockings and a garter belt. I had these black 10 inch steleto high heels on. I started in my bedroom and

Posted by a TS / CD

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An Unexpected Encounter with a New Daddy

I just had an encounter with a new daddy mans nrt me tell y'all something. This daddy mans spent bout 30 minutes eating my sissy cunt, kissing it, licking it, n sucking it. I had a sissygasm or

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Thursday Night Date Surprise

I started chatting with a nice guy one weekend. We shared a lot of likes and interests. After chatting for a bit, we decided on a first date at my house. I was so excited about our upcoming Friday

Posted by a TS / CD

By Anonymous

0

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An Unexpected Visit from Daddy Mans

I was just laying round the house chilling on the couch. I got a text from one of my daddy mens telling me he was in the area n needed to see me. I told daddy mans to stop on by. Bout 10 minutes

Posted by a TS / CD

By sissyjamie4daddys

0

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An Afternoon at the Motel Theater

I dress every couple times a year. Like to have motel room in afternoons, I would love to have a small group of guys over 50 or so, but been ghosted last couple times. Soo, I decided to get dressed

Posted by a TS / CD

By RacoonQuest8289

0

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An Unexpected Double Date Experience

I love being double n triple stuffed. Taking a cock in my ass n a cock in my mouth at the same time is fantabulous. Sucking 2 cocks n getting my ass fucked, or sucking a cock n getting my ass pounded

Posted by a TS / CD

By sissyjamie4daddys

0

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A Brave Hotel Encounter with New Friends

hi guys joise here again wanting to share my time at the hotel 6 check in and not like the last time i was ready and brave. so wasting no time i changed cloths and placing my blinking light butt plug

Posted by a TS / CD

1

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Exploring Connections with Sugar Daddies Online

Hey y'all. So like I'm on several diff gay hookup sites, n dating sites. I have met a lot, n I mean a lot of daddy mens that love a gurl like me. I have met most of my sugar daddy mens, my

Posted by a TS / CD

By sissyjamie4daddys

1

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A Night of Fantasy Under the Stars

1 night I posted a add I was going camping and wanted to dress as a bride wanted to feel like I was getting married. So I dressed in black lace panties and bra and a wedding dress. Was sitting out

Posted by a TS / CD

2

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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

Posted by a TS / CD

By OlderMaleguy

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

C caniuseu “First time shed intimacy”

John Lee Erwin I am He-Man “Chick with appendage picks me to lick her appendage.” F Freshfresh “Available for connection” A almitaaa “They found my clothes”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.5k	630	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	47.1k	525	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	73.5k	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	An absolutely amazing 3 friends	32.6k	319	1.1k	↘

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

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