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Transgender Sex Stories – Real Encounters & Passionate Experiences

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A Night of Unexpected Encounters in Iowa

Once upon a time I was in Cedar Rapids iowa. I put out a personals for a sissy gangbang. Now bear in mind desert Country Corn fed Boys and I wasn't ready for that. I was in a motel and within

Posted by a TS / CD

By Deleted User

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An Unexpected Meeting at the Bookstore

I met a daddy at a local adult bookstore. We walked into a booth n he took out his delish thicky thick cock. I love me some thicky thick goodness. I started sucking his cock as he lifted up my lil

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Hotel Meeting with Older Men

I have been a dirty cock sucking fagott since I was 18. I am now 30 years old and have sucked a lot of cock the last 12 years. I mostly suck older cocks men that are 50 and older. Doesn't matter

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By sissyjamie4daddys

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Inspiring Stories from the Community

As I read some of the stories posted here, I cant help but rub my lil ppclit hoping to cum. I read them, them make a post or 2 in hoping to find some daddy cocks to swallow n bend over for n get my

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By sissyjamie4daddys

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An Unexpected Visit with a Friend

I’m a cross dresser I’m 47 been cross dresser since I was 13 a few weeks ago a friend told me to take care of boy 18 while he was out of town just to drop by and see if he needed anything

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An Unexpected Visit and a Weekend Surprise

I remember the 1st time I put mother's stockings on. Part 3. Whoops mistake number 2. I broke character. I still have a long way to go b4 I'm a woman. Went through my mind. Mr. Thomas said.

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An Unexpected Night at the Arcade

I had the best time last night. I went to an arcade and just took 4 random cocks. I sat and played with my clit until someone approached me. I was fingered and eaten....but I really enjoyed the

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By Deleted User

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Unexpected Connections at Guys Night In

A friend of mine invited me over to his place for a guys night in. Now he knows I'm a sissy bottom n he is really cool with that. I have sucked his cock a few times n he has pounded my lil ass

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By sissyjamie4daddys

0

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An Unexpected Connection with a Trans Woman

Part two of how I became a pleasure slave for black transgender women. As she pulled me towards her and pushed my head lower while she tilted my head back as far as my neck would allow. Her

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A Chance Encounter at the Tattoo Shop

Part 1 of how I became a pleasure slave for black transgender women. I hope that this story will be posted in the transsexual stories? I am a 90% straight white masculine alpha male type. That had

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Exploring New Connections with a Young TS

I am a bi guy. I am happily married but love to sock cock and wear lingerie - my guy panties, but also women's panties and lace stockings. I practice sucking dick and getting pegged with my

Posted by a TS / CD

By cormier69fun

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An Unexpected Encounter in a Luxury Apartment

Wearing black bra and panties with thigh high and black garters-under a polka dot dress and long wool jacket I went to meet my double list hookup , an invite to his luxury apt on the 11th floor with

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An Unexpected Encounter at Daddy's Party

Part 2. With a mouthful of daddys cock, I looked over at twink. His balls were swelled up like a grapefruit. Daddy had slipped on a zip tie to twinks balls. Daddy then told me that twink was there

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By sissyjamie4daddys

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A Surprise Visit with Daddy and Friends

I am a very passionate bottom sissy..I love n enjoy making out, kissing, groping, rubbing, body licks n nibbles, KISSING, snuggles n body contact. When daddys kiss or nibble my ear or neck, OMG I

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By sissyjamie4daddys

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Unexpected Connection in Florida with a Crossdresser

I was living in florida at this time and one day searching ads of fem guys or crossdressers, I found an add for an Indonesian fem crossdresser looking for older white guy. I answered the ad and he

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A Couple's Unique Day Off Adventure

Well here goes, this was a few years ago and I had answered a CL ad from a couple looking for a guy to play with. It was like 7 am and I was cruising the ads looking to hook up with someone for the

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Exploring New Connections at the Club

Another day, another visit to the club. There were bout 35 peeps in the club. A nice mix of gay men, young, old, white n black daddys. There were a few sisters of the LGBTQ that were there, which I

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Encounter with a Pizza Delivery

Part 2. of cum in my mouth and said swallow ever drop faggot and i did he put his clothes back on left the room got his pizza bag and thatll be 21 something and a 10 dollar tip hurry up bitch i

Posted by a TS / CD

By hotkimcd4cum

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An Unexpected Encounter with a Pizza Delivery

Part 1. I ordered pizza one time after over a year of only being pegged by ex wife and she was at conference out of state. I was so nervous i dressed like a slut ordered pizza i had decided no matter

Posted by a TS / CD

By hotkimcd4cum

0

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A Surprising Encounter with a Dominant Partner

I went to meet a guy who agreed to provide oral for me. I was greeted by a tall & large and fully dressed CD who told me to go change in the bedroom. I walked in to discover slutty lingerie laid

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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

L luciecar “Don’t want it to be a boring night” R roosterrogers “Young eager for hours” J jabby69 “It took 20 years.....” S submit2one “Too Many Tops Think Anal and Intimate Technique is One in the Same”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Couple	The fast and furious	60.8k	858	4.4k	↘
#2	Tiffanyheels Gay Couple Straight	I guess I am getting to be gay	138.4k	2.0k	4.0k	↘
#3	kimorafoxxsexycd Gay Trans Couple	Swallowed my bfs meal at lunch	129.6k	1.4k	3.5k	↘
#4	cnysub Gay Trans Straight	Part 1 Nude Performer	76.5k	703	3.3k	↗
#5	KestrelElbow9092 Straight Gay Couple	Picnic Fun	49.0k	520	3.3k	↘
#6	sissyjamie4daddys Trans Couple Straight	I love water	72.1k	488	2.0k	↗
#7	wally4u Couple Trans Gay	Got Wife Off Flying To Cabo!	67.4k	309	1.9k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	53.7k	644	1.7k	↗
#9	butchmax Couple Gay Straight	Marriage did it	87.4k	628	1.7k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	83.4k	670	1.7k	↘

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

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