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Category: TS / CD

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An Unexpected Encounter in the Backwoods

I got on sniffies tonight, lots of flakes per the usual . It was getting late and someone sent me a message. They were 27 (I'm 43) 6ft 4in and 400+lbs with a 6.5" cock. We went through the

Posted by a TS / CD

By GannetShard4708

4

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An Unexpected Massage Encounter with a New Friend

Met a Feminine Fat Top on CL. He invited me to massage him. Powerful neck and back kept me busy as he moaned from my aggressive unrelenting servitude. Big ass to rub. Powerful thigs in my hands to

Posted by a TS / CD

5

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A Late Night Visit Changes Everything

I had always been a straight cross dresser. One night changed that. I was home one night, dressed up and ready for bed. I’m laying on my stomach reading, with my earbuds on. Wearing a teddy,

Posted by a TS / CD

28

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A Journey of Trust and Exploration Together

I have been happily married for many years but, as I have gotten older, I have started enjoying crossdressing when I have the opportunity. Fortunately, I have a very understanding wife who not only

Posted by a TS / CD

19

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Exploring Connections with Local and Out-of-Town Daddies

I have been out prancing n wiggling my lil sissy ass off for men for the past 8 years. Before that, I acted n pretended to be straight. I didn't have a gay bone in my body. Now, I have straight

Posted by a TS / CD

By sissyjamie4daddys

7

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Unexpected Encounter in the Grocery Lot

So I got stood up the other night. Had emailed, texted, n exchanged pics n vids with a potential daddy mans for a few days. Daddy mans wanted to meet so bad. Told me he wanted to give me a good

Posted by a TS / CD

By sissyjamie4daddys

10

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An Unexpected Visit to Daddy Man's Home

I'm a total n complete bottom prissy sissy who LOVES pleasing top daddy mens with my mouth n my lil sissy cunt. I am strictly dickly but .. last night i got invited to a daddy mans house. When I

Posted by a TS / CD

By sissyjamie4daddys

5

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An Unexpected Night with Friends

The line forms in my rear is what I told the 4 daddy mens as I lay in bed n offered them my lil sissy cunt. One by one, each daddy mens took a turn sliding their yummy cocks into my sissy cunt. I was

Posted by a TS / CD

By sissyjamie4daddys

9

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A Romantic Drive After Dinner

Met up with one of my local daddy mens at a restaurant. After we ate, we took a nice lil drive. As my daddy mans drove, I reached over n we started kissing. I reached into his pants n pulled out his

Posted by a TS / CD

By sissyjamie4daddys

5

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Embracing Identity and Finding Connection

I have been called all sorts of names: gay, queer, fairy. Faggot, any derogatory name you can think of. But I know what I am. Do the names bother me? Fuck no! Why should it? I'm a sissy, n adult

Posted by a TS / CD

By sissyjamie4daddys

7

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A Disguised Inspector's Unexpected Surprise Visit

This happened last fall. I met a qt top daddy who was into role playing. Now. I'm a prissy sissy bottom, who dresses fully from head to toe in fem clothes. Daddy told me that he wanted me to

Posted by a TS / CD

By sissyjamie4daddys

4

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An Unexpected Visit to Daddy's House

I got invited to a local daddy mens house for some sucky fucky time. Daddy mans told me to be there by 1 pm. When I got there daddy mans was already primed, locked n loaded. He met me at the front

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Company During a Winter Storm

We got hit with like a major blizzard of snow n ice n below Zero temps. Most my area got like 7+ inches of snow, bout 1/4 inch of ice since like Friday. So I have been on lock down since Friday.

Posted by a TS / CD

By sissyjamie4daddys

10

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An Unexpected Visit from Friends Leads to Fun

A few of my daddy mens came over yesterday to get their cocks wet. One of my daddy mens brought his lil twink with him. What a qt pie! Twink is 21, nice tight lil bod, hairless, n a great kisser.

Posted by a TS / CD

By sissyjamie4daddys

11

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A Chance Meeting at the Local Diner

Stopped to get a quick bite to eat at this lil diner by my house. Noticed a very attractive older man sitting by himself eating. Daddy was in his mid 60s+, very handsome silver haired fox. I sat a

Posted by a TS / CD

By sissyjamie4daddys

13

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A Night of Surprises at the Casino Suite

I met this muscular, big cocked daddy mans last night at the casino. Let me tell you something gurlfriend he was a packing! He was like 6ft 6, 250 pounds of solid muscle football player, n a very

Posted by a TS / CD

By sissyjamie4daddys

7

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Exploring the Dynamics of a Sugar Baby Relationship

I have a fetish for OLDER white daddy mens, 60 years n older. I had a daddy mans that took REALLY good care of me introducing me to man love several years ago. I was 24/25 when I met him. He was 73.

Posted by a TS / CD

By sissyjamie4daddys

6

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An Unexpected Encounter in the Shed

Early today I was dressed up still e I am a cross dresser , and I keep hearing g this noise in my metal shed out back , now I live alone, so I walk out there still dress mind you I mean in thongs,

Posted by a TS / CD

14

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An Unexpected Encounter with a Delivery Driver

Sitting at the house riding a nice 9" cock substitute, a dildo, squeezing n pinching n licking my tittys wishing I had a real mans cock in my sissy ass. Woke up feeling raunchy n horny. I'm

Posted by a TS / CD

By sissyjamie4daddys

9

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An Unexpected Encounter in the Office

I'm a crossdressing lil sissy who wears her clothes under her man clothes n I HATE it! God I would love to be able to wear my fem clothes but the world ain't ready for that. I am very Very

Posted by a TS / CD

By sissyjamie4daddys

11

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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

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” S sissyemilymatt “Night walk”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Couple	The fast and furious	59.8k	840	4.4k	↗
#2	Tiffanyheels Couple Straight Trans	Girlfriend turned bi and craves females	132.7k	2.0k	3.9k	↗
#3	kimorafoxxsexycd Gay Trans Couple	Swallowed my bfs meal at lunch	127.6k	1.4k	3.5k	↗
#4	KestrelElbow9092 Straight Gay Couple	Picnic Fun	48.5k	517	3.3k	↗
#5	cnysub Gay Trans Straight	Part 1 Nude Performer	75.1k	694	3.3k	↗
#6	sissyjamie4daddys Trans Couple Straight	I love water	71.4k	487	2.0k	↗
#7	wally4u Couple Trans Gay	Got Wife Off Flying To Cabo!	67.0k	309	1.9k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	53.6k	644	1.7k	↗
#9	butchmax Couple Gay Straight	I Guess We Asked for it	83.2k	616	1.7k	↘
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	82.7k	668	1.7k	↘

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