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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Category: TS / CD

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Exciting Encounters at a Scenic Vista Point

Does anybody else get excited at the thought of having sex at a rest stop or Vista point off of the highway? Down in Santa Cruz County there is a really hot vista point that is always full of action.

Posted by a TS / CD

By Deleted User

14

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An Unexpected Night with Friends

I met up with a daddy mans n his friend last night for fine double fucking n sucking. Daddy mans has a nice thick cock, bout 6 inches. Daddy mans friend has a very nice 8 inch cock, but not thicky

Posted by a TS / CD

By sissyjamie4daddys

3

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A Journey into Unexpected Power Dynamics

Ok I’ll start from the beginning where my first mistake or my first success was when I told the power top exceptionally well endowed bbc that was my biggest fantasy of all time that I had no

Posted by a TS / CD

10

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A Surprising Change in Living Arrangements

So after about a mouth he said move in be what I said and I said what house wife or wife or fucking maid He, nooo not like that at all days you off just pickup around house ok so working 3days week

Posted by a TS / CD

2

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A Surprising Turn in Their Living Situation

So after about a mouth he said move in be what I said and I said what house wife or wife or fucking maid He, nooo not like that at all days you off just pickup around house ok so working 3days week

Posted by a TS / CD

1

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An Unexpected Night Out with My Boss

(Wifey for boss) I been crossdresseing scent I was 13 been sucking on & fucking just as long.i was working this small caft as kitchen work 3/4days parttime I know the boss was gay i seen him

Posted by a TS / CD

6

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Curvy Crossdresser Seeks Strong Man for Adventure

Slutty CD Bottom – Big Fat Ass Needs Dominant Top Body: Hey dominant tops 😈 I’m a smooth, curvy crossdresser who’s 100% slutty bottom and obsessed with pleasing a strong man. My

Posted by a TS / CD

By xxxxxxdrew96

6

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A Crossdressing Encounter at His Home

I'm a early 30s CD. I'm single so whenever not at work, I'm always cross dressing. Some time I even leave my house to go to the store while dressed. I'm 100% passable when

Posted by a TS / CD

By funmidwestern

16

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An Unexpected Visit from My Sister's Boyfriend

I’m a discrete cross dresser. No one knows except my sister. One day I’m dressed up and she comes home with her boyfriend. I panic a bit. She says don’t worry he won’t say

Posted by a TS / CD

By Deleted User

19

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A Late Night Visit to Daddy's House

A new daddy mans told me to stop by his place after I left nother daddy mans house. It was like 1-130 in the morning. I knocked on his door n he let me in. He was standing there naked n we kissed as

Posted by a TS / CD

By sissyjamie4daddys

6

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An Evening of Fantasy and Intrigue at Home

It all started one evening I was sitting alone at the house had this horny mood coming on so I took a shower but all dressed up my heart and sexy I was laying on my bed watching some CD porn and

Posted by a TS / CD

4

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Exploring Identity and Self-Acceptance

I have been a bottom sissy slut for 8 years. I love n enjoy sucking cocks, guzzling up that sweet yummy cum, n riding a nice hard thick cock. I have NO idea why I wasted 40 plus years chasing pussy.

Posted by a TS / CD

By sissyjamie4daddys

4

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A Night Out: Dancing and New Connections

So I met up with some gurlgriends last night for a drinky pooh. These girls are looking to find that one special man to love them, blah blah blah. They all dress classy n sophisticated. Me? I'm

Posted by a TS / CD

By sissyjamie4daddys

3

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An Unexpected Connection Over Drinks

It started as one of those nights where I wasn’t expecting anything special. I had just gotten home, changed into something comfortable, and decided to scroll through messages. One message

Posted by a TS / CD

3

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Unexpected Encounters at a Motel After Reunion

hi josie here again with a unexpected story that happened just last night. i was on my way home from a family reunion and stopped at a motel to rest not dressed or anything just plan me. as i was

Posted by a TS / CD

6

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A Memorable Birthday Celebration at the Theater

I used to dress and go to an adult theater, in my late 50's I had health issues and stopped going. I only have sex with a married fwb when he can get away from his wife. It's my 70th

Posted by a TS / CD

6

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An Unexpected First Date Revelation

Not sure where to put this. I am intersex. It’s rare to be intersex and it’s even more rare to have both a penis and a vagina. I look like a female. I am very good looking. I have many

Posted by a TS / CD

By Deleted User

18

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An Unexpected Invitation to a Party

I was always feminine, you could say, very gay 5'4" 120 lbs. Started dressing after high school after I moved into my own place. my landlord's are a gay couple and they told me they

Posted by a TS / CD

13

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An Unexpected Encounter in the Parking Lot

So this just happened today n like I was totally into it. I was out running some errands n shopping. I parked my car n started heading into the store then I saw something out the corner of my eye.

Posted by a TS / CD

By sissyjamie4daddys

12

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A Close Call in Cancun: Escaping Danger

How I belive i escape sex trafficers/ cartel in cancun last July i book vacation 21day fly in check in nice hotel in nice area. Get to my room off with my fuck man cloths steart fixing my self up and

Posted by a TS / CD

5

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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 “Give it to me buddy”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	33.9k	625	4.1k	↗
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	76.3k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.2k	352	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	45.8k	520	2.9k	↗
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	70.6k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	43.6k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	From Zorbas To His Hotel Room	50.1k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	47.8k	600	1.7k	↗
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	9.9k	357	1.2k	↘
#10	Dedavis Straight for Gay Straight	House hunting pt 1	37.9k	276	1.1k	↗

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

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