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Category: TS / CD

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My first Big Black

It all started innocently enough as previously stated i began exploring with older men and they were and still are a fetish to me the old man that i gave to oral first one day bought me a dildo ,

Posted by a TS / CD

10

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Look back at me...

Very very nervous kind of guy that likes to dress in my girls sexy things. Put an ad up and finally had someone i likes that wanted to meet. My post was simple but, hoping for more. "MASSAGE ME

Posted by a TS / CD

16

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Crossdresser with attractive girlfriend

I had been a crossdresser years before meeting my girlfriend. She was sexy, hot and tasty. I ate her sweet pussy daily and slid my cock Into her daily and in many outdoor locations, in the car,

Posted by a TS / CD

By Tiffanyheels

13

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I was straight and didn't know

Hi.\nEverybody, I just want to share my story.I was 18 years old, and I was in the navy down in San Diego and my friend, and I went to this adult bookstore, I think it was F.Street book store

Posted by a TS / CD

6

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Going to the Movie Theater

I've been dressing for about 3 years now. Started after I moved into my own place at 22. I'm small, 5 ft. 4 in. 132 lbs , long hair usually in a ponytail. I've never been out in public

Posted by a TS / CD

20

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My first experience

My First Experience Up until that point, I’d been satisfying my exhibitionist side online—mostly through cam sites, where I’d show off my body and send slutty pics to horny men.

Posted by a TS / CD

13

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Walking Into The Unexpected

So Me And My Wife Has Really Been Studying The Swinger Lifestyle So We Been Subscribing To Apps Connecting With Other Couples And Basically Getting Broke Into The System, I Was Chatting With This

Posted by a TS / CD

By Deleted User

6

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Oh no he didn't!!

So my gf and I picked up a bi male and had the come to our hotel for a little fun. It was the first time I had ever done or was going to do anything with another guy. We said out introductions and

Posted by a TS / CD

16

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Daily self-pleasure

I have dressed as a slut for years. Starting with taking my sister’s panties and bras and masturbating. Then I found my mother’s girdle with stockings and put those on that was a

Posted by a TS / CD

By Tiffanyheels

20

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Wonderful Black Woman

I placed an ad on dl to find a woman that wanted ate. I received a reply a couple days later and we exchanged a few messages back and forth. She told me she would be passing thru in a couple weeks.

Posted by a TS / CD

12

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Sissy Story Drugs & Clothing

In 2016 my fiance and I had gotten back together but we were looking to spice up the bedroom so we looked to using drugs together. Our love life was ok; nothing that was adventurous or really work

Posted by a TS / CD

16

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only if i was born female

if i had been born female i would not have spent the last 3 years getting surgeries done to become the perfect trans girl i am today i have always been small petite and started growing my hair out

Posted by a TS / CD

13

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I Didn't Know She Had A Body Part!

I had gone to Rosarita Beach Look'n to cleat my head after breaking up from a short relationship. My timeshare was amazing with it's beach view & private spa. I noticed a Stunning

Posted by a TS / CD

36

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Sucking appendage in the club

When I was broke in some 8 years ago, my daddy used to take me out on date night to a club bout 45 minutes from our place. My daddy loved watching other daddys flirt with me n he would always tell me

Posted by a TS / CD

By sissyjamie4daddys

15

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Fun in the motorhome while wife was sleeping inside

I'm a 60 year old sissy faggot crossdresser cumslut that NEEDS MULTIPLE CREAMPIES and to be used HARD. I had a Alpha dom top meet with me in the motorhome outside the house last night and damn

Posted by a TS / CD

By Deleted User

14

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Fun in the motorhome while wife was sleeping inside

I'm a 60 year old sissy faggot crossdresser cumslut that NEEDS MULTIPLE CREAMPIES and to be used HARD. I had a Alpha dom top meet with me in the motorhome outside the house last night and damn

Posted by a TS / CD

By Deleted User

5

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Role Playing

As a non passable cross dresser I was looking around at some Ads and was hoping to find something different. A ad caught my eye looking for a CD to "Role Play" in his home. I responded to

Posted by a TS / CD

14

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My first Big Black

As a non passable cross dresser I have had a few good times with a few good men. Flipping through ads and I became obsessed with wanting to experienc a bbc. I bought some bigger black dildo's

Posted by a TS / CD

6

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Restroom oral activity

It was a week night when I went to a local theater. I walked into the men’s room and there was guy in a stall clearly standing on a toilet jerking his cock. He was looking above the stall wall

Posted by a TS / CD

By Tiffanyheels

23

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Makayla's first.

Well to start this happened about 9 years ago my first time being with a man being a transgender woman. Omg I met him on Craig's list mmm was so much fun we chatted a bit first exchanged numbers

Posted by a TS / CD

21

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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	33.8k	624	4.1k	↗
#2	Tiffanyheels Trans Couple Straight	Crossdressing intimacy in office	76.1k	1.4k	3.2k	↘
#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	23.0k	352	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	45.4k	518	2.9k	↗
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	69.5k	1.0k	2.7k	↗
#6	sissyjamie4daddys Trans Couple Straight	Sucking appendage in the club	43.4k	456	1.9k	↘
#7	wally4u Gay Trans Straight for Gay	From Zorbas To His Hotel Room	50.0k	272	1.8k	↘
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	47.4k	593	1.7k	↗
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	9.8k	356	1.2k	↗
#10	Dedavis Straight for Gay Straight	House hunting pt 1	37.8k	276	1.1k	↗

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