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Category: TS / CD

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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

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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

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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

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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

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By sissyjamie4daddys

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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

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By Deleted User

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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

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By sissyjamie4daddys

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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

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By sissyjamie4daddys

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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

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By sissyjamie4daddys

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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

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By sissyjamie4daddys

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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

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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

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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

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By sissyjamie4daddys

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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

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By Deleted User

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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

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Unexpected Guests During Wife's Absence

When my wife isn't home I like to dress up in her clothes and prance around the house in a skirt or a dress. I'm a closeted CD and bisexual. I have been with a few men when I get the

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By sissyjamie4daddys

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Unexpected Encounter: A Trucker's Surprise Meeting

I am an over the g egg pad trucker and a closet crossdresser and was straight until the night I’m fixing to tell you about ! I had gotten to where I was to unload the next morning early the day

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An Unexpected Encounter at the Toy Show

Its my own fault because i ran a post for a daddy to do whatever. I am a sissy so i offered to do a toy show for him in person. He def took me up on it because this is what happened. I was a dolled

Posted by a TS / CD

By rachelbottomcd

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A Unique Encounter in a Parking Lot

So the other day I was meeting up with this guy at a nearby porn shop. It was a good place to go have fun. So I love wearing sexy mini dresses and sexy lingerie. Be we went in I wanted to meet up in

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An Unexpected Visitor While She Was Away

One of my wife's bulls stopped by the other day while she wasn't home. He was not happy. "I got a 5 day load backup. Now someone is going to take it, and since she isn't here,

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By sissyjamie4daddys

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A Sugar Daddy's Visit After a Rough Flight

One of my sugar daddy mens texted me earlier in the week telling me I would be def earning my allowance. My response to his text: bring it on sugar daddy. N he did! My sugar daddy mans showed up at

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By sissyjamie4daddys

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Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
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#6	Dedavis Straight for Gay Straight	Massage studio part three	113.8k	761	2.1k
#7	wally4u Gay Couple Trans	Drunk Abs Experience I'll Never 4Get!	75.1k	331	2.0k
#8	sissyjamie4daddys Trans Couple Straight	I love water	87.9k	498	2.0k
#9	Steve Straight Straight for Gay Gay	Vacation with my Aunt part 1	59.9k	692	1.8k
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	88.6k	678	1.7k

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