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Category: TS / CD

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An Unexpected Encounter in a Delivery Van

I started working for this place. One of my coworkers was also one of my ex wifes fuck buddys. So like one day him n I had to delivery some things bout 1.5 hour away. Now I always thought he was a

Posted by a TS / CD

By sissyjamie4daddys

17

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A Night Out at the Dance Club

There I was dressed in a very nice red dress. Short but looked good on me. I was thinner back then and could slide into a size 10 dress. This was a one piece and zipped up the back. I wore white

Posted by a TS / CD

11

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A Journey of Longing and Unexpected Encounters

1,2 maybe 3 really large black men come into my path for one thing, to fuck like that couldn't ever fuck again after this there final fuck I mean deep raw fucking, I way h born every day and

Posted by a TS / CD

By Deleted User

3

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Unexpected Hotel Fantasy Encounter

I was just traveling for my job it takes me to different places often. I always have been secretly dressing up like a total sissy completely submissive so I had planned to use my hotel as a perfect

Posted by a TS / CD

12

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An Unexpected Encounter at the Bookstore

I was at my local adult bookstore sucking cocks in a booth. Now I'm an older crossdresser who is strictly dickly, a total n complete bottom prissy sissy. I'm a cock gobbling, cum guzzling,

Posted by a TS / CD

By sissyjamie4daddys

6

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An Unexpected Encounter in the Backwoods

I got on sniffies tonight, lots of flakes per the usual . It was getting late and someone sent me a message. They were 27 (I'm 43) 6ft 4in and 400+lbs with a 6.5" cock. We went through the

Posted by a TS / CD

By GannetShard4708

4

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An Unexpected Massage Encounter with a New Friend

Met a Feminine Fat Top on CL. He invited me to massage him. Powerful neck and back kept me busy as he moaned from my aggressive unrelenting servitude. Big ass to rub. Powerful thigs in my hands to

Posted by a TS / CD

5

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A Late Night Visit Changes Everything

I had always been a straight cross dresser. One night changed that. I was home one night, dressed up and ready for bed. I’m laying on my stomach reading, with my earbuds on. Wearing a teddy,

Posted by a TS / CD

28

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A Journey of Trust and Exploration Together

I have been happily married for many years but, as I have gotten older, I have started enjoying crossdressing when I have the opportunity. Fortunately, I have a very understanding wife who not only

Posted by a TS / CD

19

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Exploring Connections with Local and Out-of-Town Daddies

I have been out prancing n wiggling my lil sissy ass off for men for the past 8 years. Before that, I acted n pretended to be straight. I didn't have a gay bone in my body. Now, I have straight

Posted by a TS / CD

By sissyjamie4daddys

7

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Unexpected Encounter in the Grocery Lot

So I got stood up the other night. Had emailed, texted, n exchanged pics n vids with a potential daddy mans for a few days. Daddy mans wanted to meet so bad. Told me he wanted to give me a good

Posted by a TS / CD

By sissyjamie4daddys

10

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An Unexpected Visit to Daddy Man's Home

I'm a total n complete bottom prissy sissy who LOVES pleasing top daddy mens with my mouth n my lil sissy cunt. I am strictly dickly but .. last night i got invited to a daddy mans house. When I

Posted by a TS / CD

By sissyjamie4daddys

5

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An Unexpected Night with Friends

The line forms in my rear is what I told the 4 daddy mens as I lay in bed n offered them my lil sissy cunt. One by one, each daddy mens took a turn sliding their yummy cocks into my sissy cunt. I was

Posted by a TS / CD

By sissyjamie4daddys

9

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A Romantic Drive After Dinner

Met up with one of my local daddy mens at a restaurant. After we ate, we took a nice lil drive. As my daddy mans drove, I reached over n we started kissing. I reached into his pants n pulled out his

Posted by a TS / CD

By sissyjamie4daddys

5

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Embracing Identity and Finding Connection

I have been called all sorts of names: gay, queer, fairy. Faggot, any derogatory name you can think of. But I know what I am. Do the names bother me? Fuck no! Why should it? I'm a sissy, n adult

Posted by a TS / CD

By sissyjamie4daddys

7

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A Disguised Inspector's Unexpected Surprise Visit

This happened last fall. I met a qt top daddy who was into role playing. Now. I'm a prissy sissy bottom, who dresses fully from head to toe in fem clothes. Daddy told me that he wanted me to

Posted by a TS / CD

By sissyjamie4daddys

4

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An Unexpected Visit to Daddy's House

I got invited to a local daddy mens house for some sucky fucky time. Daddy mans told me to be there by 1 pm. When I got there daddy mans was already primed, locked n loaded. He met me at the front

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Company During a Winter Storm

We got hit with like a major blizzard of snow n ice n below Zero temps. Most my area got like 7+ inches of snow, bout 1/4 inch of ice since like Friday. So I have been on lock down since Friday.

Posted by a TS / CD

By sissyjamie4daddys

10

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An Unexpected Visit from Friends Leads to Fun

A few of my daddy mens came over yesterday to get their cocks wet. One of my daddy mens brought his lil twink with him. What a qt pie! Twink is 21, nice tight lil bod, hairless, n a great kisser.

Posted by a TS / CD

By sissyjamie4daddys

11

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A Chance Meeting at the Local Diner

Stopped to get a quick bite to eat at this lil diner by my house. Noticed a very attractive older man sitting by himself eating. Daddy was in his mid 60s+, very handsome silver haired fox. I sat a

Posted by a TS / CD

By sissyjamie4daddys

13

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#8	Dedavis Straight for Gay Straight	Super Bowl group event part six	102.3k	705	2.0k	↗
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