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Category: TS / CD

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A Surprise Encounter During a Business Trip

During the day I act as straight as I can. When I'm at home, I am as fem as I can be: dresses, skirts, blouses, makeup, wigs, etc. I have left my house a few times dressed when I have had dates

Posted by a TS / CD

By Deleted User

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An Unexpected Connection at Home

I have always enjoyed dressing up and playing the part of a woman. I was married and had children but I loved being in the arms of a man that treated me like a woman. My best lover was a man I met

Posted by a TS / CD

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Unexpected Meeting at the Adult Bookstore

I am a middle aged, under-the-radar CD who has taken limited opportunities to let my gurl self out. One Saturday mid-day I took myself off to and adult bookstore/video booth establishment to see

Posted by a TS / CD

By Deleted User

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An Unexpected Surprise Visit from New Friends

Daddys surprise cont.... Daddy told me both were in their early 40s, with huge cocks. Daddy told them all about me being cheap n easy, i was a gurl, and how I love cock n cum. Daddy told them I would

Posted by a TS / CD

By Deleted User

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Unexpected Meeting at the Indy Motel

I posted an ad in Indy, saying I was a sissy cd looking to give oral. I invited two guys over to the motel. The first guy arrives, muscular black man. I got on my knees and he slapped my lips with

Posted by a TS / CD

By oralcdbottom

0

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Navigating Life with a Supportive Roommate

I am a passable fem lifelong pantyhose crossdresser. At 54 I still have my slim body and my great legs and bummy. I am a lucky gurl. I am addicted to sheer to waist pantyhose, I wear them 360 days a

Posted by a TS / CD

By lisajonesxoxo

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An Unexpected Date at the Football Game

I got invited to a football game the other night by an older top daddy. His grandson is the football star for his team. Daddy asked me to wear a dress, and of course, no panties. Btw, I never wear

Posted by a TS / CD

By Deleted User

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Exploring Hidden Desires and Secret Encounters

Having a tiny cock, never had the action with woman other have. At 9 some older boys taught me to suck cock and love doing it. They told me I should have been a girl, but if I swallowed lots of cum

Posted by a TS / CD

By Grandpa needs it

0

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A Surprise Visit from Daddy: A Unique Encounter

I'm a sissy CD but live my life straight. With a wife that knows I like to dress in panties and have a feminine side, she doesn't know the lengths that I've gone. My experiences with

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An Unexpected Visit from a Young Couple

I am a semi passable crossdresser, meaning from the neck down. I don't wear wigs, but I do wear makeup, and feminine clothes. I am very feminine when dressed, which is usually at home, in the

Posted by a TS / CD

By Deleted User

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A Crossdresser's Unexpected Toy Play Encounter

I have been cross dressing for about 10 years now and can't seem to get enough cock to satisfy my love for it. After a night of getting my pussy stuffed and swallowing as many loads as I can, I

Posted by a TS / CD

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A Journey of Confidence: Dressing in Public for the First Time

As a traveling business man, I have a lot of spare time in hotel rooms. Being a closet sissy CD. Only a couple of times did I post an add, for company. Mostly I would dress up fully in my room

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A Journey of Self-Discovery in Public

As a traveling business man, I have a lot of spare time in hotel rooms. Being a closet sissy CD. Only a couple of times did I post an add, for company. Mostly I would dress up fully in my room

Posted by a TS / CD

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A Journey of Self-Discovery and Acceptance

Hi, my name is Serena. I'm a TS. I'm 23, Blonde about 5'6 around 125 and a 32-22-34. I have small what I call a small clity, it's about 3 inches now. My story began when I was

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Unexpected Encounter in the Confessional Booth

I thought I knew how to please a man: continued: it had been a little over a month since my mom and I had our hot first visit to the booths at the local abs. My mom had become a great cock sucker

Posted by a TS / CD

By OspreyGrove7318

0

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An Unexpected Connection at a Resort Bar

As promised here is a good one from one of my trips in Malaysia, Penang to be specific. We would layover in this great resort hotel on the Straits of Malacca which is part of the Indian Ocean, about

Posted by a TS / CD

By LionAlloy5346

0

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An Unexpected Meeting at the Coffee Shop

I met a very handsome top daddy a few weeks ago at a coffee place that hubs and I stopped at. Very handsome daddy with a nice body, and muscular. We started chatting, and he invited me back to his

Posted by a TS / CD

By Deleted User

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A Daring Night in a Skirt and Heels

I am a straight guy, but I have always enjoyed dressing up in skirts, hose, panties, painted toenails and heels. I had only ever dressed at home for an occasional cam session. I really loved getting

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A Journey of Self-Discovery in a Hotel Room

I'm a closeted part time sissy crossdresser. Every few months, I treat myself to a nice hotel room. I love the luxury of having the time and space to shave myself smooth, put lotion on my

Posted by a TS / CD

By alexiscdslut

0

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Exploring Identity Through Online Connections

I was younger and realized I was more feminine than masculine and also had oral skills, But I truly loved sucking dick. I sat at my computer as I looked at porn and found tranny porn. I thought back

Posted by a TS / CD

By hypnodestiny

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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.

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C caniuseu “First time shed intimacy”

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Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	34.3k	629	4.1k	↘
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	77.0k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.5k	353	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	46.9k	523	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	73.0k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	44.3k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	My Birthday Suprise!	51.1k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	48.8k	605	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.0k	357	1.2k	↘
#10	powers8 Straight Gay Straight for Gay	An absolutely amazing 3 friends	32.5k	318	1.1k	↘

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

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