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Category: TS / CD

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An Unexpected Visitor and a Surprising Encounter
I posted an ad on double list under the guys for guys that redi I will do what she wontor can't. And then all of a sudden I began to get several emails it was one after the other so I started

Posted by a TS / CD

By Slut puppy randi

Unexpected Connections at the Local Club
I stopped at a local club last night to see if anything was going on. There was maybe 20-25 peeps in the club, mostly daddy mens n a few twinks. I pranced my way to the bar n got a drinkypooh. An

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from a Charming Daddy
I was on AFF a few nights ago looking for a top daddy who needed some sucky fucky time. An older daddy replied, and we exchanged pics and info. Dam, daddy had a nice looking cock, thick, and delish

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter at the Bar
I'm a CD totally passable went to a bar and within 30 mins a black guy walk up said hey ma'am how are you tonight. I. Continued to talk to him and after while told him I was a CD he said

Posted by a TS / CD

By beachbottom74

A Weekend Escape with My Sugar Daddy
One of my local sugar daddy mens invited me to spend the weekend with him at his house. His wifey pooh was going out of town to visit her fam. I told my sugar daddy mans that I would love to spend

Posted by a TS / CD

By sissyjamie4daddys

A Disappointing Visit from a Young Stud
Why the fuck do daddy mens waste my mother fucking time? Tired of the game players, the lying ass men that want a guaranteed piece of ass, an easy piece of ass, then show up n they look nothing like

Posted by a TS / CD

By sissyjamie4daddys

A Cozy Night at the Local Bar
I stopped at a lil bar last night to have a drinky pooh with a nice daddy mans who is a regular of mine. The bar was not that busy, maybe 12-15 peeps there. We got cozy at a lil booth, kissing n

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Roommate Encounter During Training
I have been a closeted cross dresser for a long time. This past week I was out of town for a training event. I took a little outfit thinking I would be in a home alone. I get checked in and go up to

Posted by a TS / CD

By dmieck

Preparing for a Night Out in a Hotel Room
So this just happened this week. I travel from city to city for work. So my company would put me up in nice places. We had just got off work. I was closing the office and driving back to my room. It

Posted by a TS / CD

By Miniho

An Unexpected Connection with the Pizza Delivery Guy
Earlier today I was sitting on my couch painting my toes to go out tonight. I was wearing a red nightie, just chillin. The doorbell rang. I wasn't expecting anyone so I got up to answer the

Posted by a TS / CD

By sissyjamie4daddys

An Evening Swim Turns Into a Surprise Encounter
A coworker of mine invited to her place to go swimming (she knows I'm a crossdresser and in the stages of transition) she told me to come over to her place in the evening she has an indoor

Posted by a TS / CD

By Deleted User

A Surprise Visit to Daddy Man's House
Last night I stopped by a daddy mans house for a lil sucky fucky time. This daddy mans has a very nice n sweet cock. When I got to his house, daddy mans was sitting in a chair stroking that beautiful

Posted by a TS / CD

By sissyjamie4daddys

A Fun Surprise Party with New Friends
I was invited to daddy mans place last weekend. Daddy mans had a surprise for me, a lil party n he needed a party favor. When I got to daddy mans place, there were 3 other daddy mens, n a lil twinky

Posted by a TS / CD

By sissyjamie4daddys

Exploring Connections with Older Partners Online
I have been on this site plus a few others always posting bout what I am looking for. I'm honest n up front with potential fuck partners. Why lie bout who I am, what I love to do with daddy

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Morning Call from My Sugar Daddy
One of my local sugar daddy mens called me this morning. He needed me to come over ASAP as he has a problem that only I could take care of. I got dressed n went over to his house. He was standing

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter with Friends
josie adventure part 2.... these guys were very determined too. so i wasted no more time because this is what i was wanting for so long i lick each head and started suck dick and getting my head push

Posted by a TS / CD

By greatime00

A Night of Unexpected Encounters
hi this is josie and i want to tell you what i did and will do again omg it was great. a year of fantasizing about the only 2 big black cocks i have had sex with by the way only 1 at the time i

Posted by a TS / CD

By greatime00

An Unexpected Visit to a Secured Complex
Yesterday I stopped at a daddy mans place for some sucky fucky time. This daddy mans lives in a secured apartment complex where you have to sign in n out of when you visit, n have to give a reason

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Meeting with an Older Man
So I have a rare few days alone and decided immediately I would lock my clitty up and be a complete slutty mess and try and find a Dom older daddy to service. Made a post and got a message from a

Posted by a TS / CD

By Deleted User

A Chance Meeting Under the Bridge
so i been a crossdresser sissy my whole life im very petite and fem i lived with my parents up till may 2023 im mid 20s and I finally saved enough for an apartment and all the utilities and

Posted by a TS / CD

By ababycd

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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