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An Unexpected Gathering at a Baby Shower

I got invited to a baby shower Friday night. When I got to my daddy mans place, he had 5 other daddy mens there. When I got there, all 6 daddy mens we're already naked, waving their delish cocks

Posted by a TS / CD

By sissyjamie4daddys

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A Festive Night of Unexpected Connections

The Christmas Party. I posted here about a year ago. My first time in public dressed up as a woman. I went to Fantasy Fest in Key West. I then went out in Fort Lauderdale New Years Eve. I met a guy

Posted by a TS / CD

By privateer269

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A Wild Birthday Surprise with New Friends

I am a sissy, a complete submissive bottom for all top men to use as they seem fit to. I love to dress up as a sissy for all men. And I love getting beef injections in my cunt and mouth. I love

Posted by a TS / CD

By sissyjamie4daddys

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A Surprise Weekend Visit from Friends

OMG, what a way to start my weekend! I had 2 of my daddy mens stop by my house for some sucky fucky time. Both daddy mens got here bout 7ish, n didn't waste no time. We sat on the couch kissing,

Posted by a TS / CD

By sissyjamie4daddys

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A Scenic Drive Leads to Unexpected Connection

A daddy mans called me early this morn n wanted to go for a nice long drive. Daddy mans picked me up bout 930, n as soon as I got into his truck, he kissed me. I noticed his cock was out, n daddy

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Reunion at a Family Funeral

I was married to a real woman for a quick minute, but divorced after I came out. I started transitioning to fem shortly after, n moved a few states away. My ex wife has a big family, lots of cousins,

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Meeting on Sniffies

I was cruising on Sniffies just browsing and saw a guy with a 11inch beautiful pole. I decide to message him asking if I could make out with it (suck it sloppy) he replied “both” I was a

Posted by a TS / CD

By Bubblebottom1061

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Unexpected Encounter at the Mall Food Court

Home for the holidays. part 2. If you remember from part 1, I am a 19 year old sissy tranny transitioning to full time. I'm home from school for the holidays and ran into a guy at the mall that

Posted by a TS / CD

By Deleted User

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A Cozy Evening with Daddy John

Daddy John part 2 I bobbed up and down on his cock, taking as much of daddy John's cock in my throat as I could. Daddy John's cock grew to about 8", and was very tasty. I licked,

Posted by a TS / CD

By sissyjamie4daddys

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Discovering New Connections After Divorce

Up until 8 years ago, I lived a straight lifestyle. I was going thru a divorce when I had my 1st sexual encounter with an older man. I was very bi curious at the time, having watched my soon to be ex

Posted by a TS / CD

By sissyjamie4daddys

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A Surprise Gift from My Sugar Daddy

Today has been a fab day. I woke up all snuggled n cuddled next to one of my sugar daddy mens who is in town for 2 days before he has to go back to his fucking cunt of a wifey-pooh. At least I get to

Posted by a TS / CD

By sissyjamie4daddys

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A Day of Style and Surprises at the Cabin

Part 8 Hunting camp: After the hug she asked if he dresses me like this a lot. I said yes, she said do you like it? I said I really do, I said I love the way he looks at me, cannot keep his hands off

Posted by a TS / CD

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Celebrating at the Cabin: A Night to Remember

Part 7 Hunting camp: as we got back to the cabin, he told me, this evening we are going to a local bar for drinks to celebrate. I said. I am only 19, and cannot drink. He said, you will be fine,

Posted by a TS / CD

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A Secret Sleepover Connection Between Friends

Part / on a man’s shoulders and me almost screaming fuck me baby fuck me good yes oh fuck it feels good then suddenly without being touched I started cumming and strted humping him back yes yes

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A Surprising Discovery with My Roommate

After my wife and me divorced I let a friend move in with me and he knew nothing about me dressing up and I always kept my stuff locked up except for one day when I was in a hurry and left the house

Posted by a TS / CD

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A Weekend of Unexpected Encounters in Virginia Beach

Another true story. My first story was about cross-dressing in Pennsylvania in a motel across the street from a video store. This one is different. I was traveling again for my job and stopped in

Posted by a TS / CD

By RacoonQuest8289

0

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A Weekend Visit from My Sugar Daddy

So 1 of my sugar daddy mens called me the other day informing me he was in town for a few days n wanted to spend some time with his baby gurl. I agreed n invited my sugar daddy mans to stop by Friday

Posted by a TS / CD

By sissyjamie4daddys

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A Nervous Trip to the Lingerie Store

Part 5 hunting camp. As we sat in the truck he said to me “are you sure you want this to continue?”, I immediately said yes sir. “ this means that you must completly trust me and

Posted by a TS / CD

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Unexpected Adventures at the Cabin Camp

Part 3 Hunting camp. There I was still on my knees covered in cum. He then said it was time to go to bed, we had to get up early. He had a bedroom on the back side of the cabin, he had added it a few

Posted by a TS / CD

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A Surprising Reunion at the Mall

First a little about me. I am a 19 year old femboy, a sophomore in college in another state but home for the holidays. I have always been small and femme and was always teased and even laughed at

Posted by a TS / CD

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 loverlips699 “The love of dressing up like a playful little submissive crossdresser sissy boy” S sexydadbottom “So this just happened…” U uni4fun5 “Charming night calls” 2 2026lovingslut “Wife is out of town for 2 months”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Straight for Gay Couple Straight	I couldnt refuse the temptation.	49.1k	734	4.3k	↗
#2	Tiffanyheels Straight Couple Trans	Finally had intimacy with ex mother in law	99.7k	1.7k	3.4k	↘
#3	KestrelElbow9092 Straight Gay Straight for Gay	A chance meeting.	35.6k	427	3.2k	↘
#4	kimorafoxxsexycd Gay Straight Couple	Bf was a sweetheart today	101.0k	1.2k	3.1k	↗
#5	cnysub Trans Gay Straight	My boyfriend/ Master/partner	60.2k	606	3.0k	↗
#6	sissyjamie4daddys Trans Couple Straight	I love water	60.2k	468	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Night At The Anvil... Part 1	57.9k	279	1.8k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	51.8k	629	1.7k	↘
#9	powers8 Straight Straight for Gay Gay	My greatest vacation ever	51.1k	478	1.3k	↗
#10	butchmax Straight for Gay Couple Straight	My Wife Got Sick	59.0k	471	1.3k	↗

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