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Transgender Sex Stories – Real Encounters & Passionate Experiences

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Navigating Generous Relationships and Allowances
I love me some generous daddy mens. I have 7 sugar daddy mens that I take care of by spending sucky fucky time with. In return for my time, I have allowances with each one. When I'm not with a

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Visit from an Old Friend
I was sitting on the couch, legs spread, riding a 10" dilly, when someone knocked on my front door. Perfect fucking timing! Way to interrupt my fun time. I started walking towards the door n I

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Hotel Encounter with Daddy
I responded to an ad on DL from a daddy who was staying at a hotel n was looking for a sissy gurl to stop by n play. Daddy gave me the hotel n room number n told me the door would be open. The hotel

Posted by a TS / CD

By sissyjamie4daddys

A Night Out: Dinner and Dancing Together
The first time I was turned out fully dressed in public was at a restaurant. I shaved my body completely smooth, was wearing a black dress that had a slit in the back, heels, stockings, panties,

Posted by a TS / CD

By sissyjamie4daddys

Exciting Bahamas Vacation with My Sugar Daddy
I got a call from one of my sugar daddy mens last night. Sugar daddy mans wants to take me on a lil vacay to the Bahamas, all expenses paid of course, for 2 weeks! I told him I would love to

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Gathering at Daddy Man's Place
I was invited to a group party this past Monday at a daddy mans place. Daddy mans told me there would be a few other daddy mens there n another sissy gurl. When I got to daddy mans place I was told

Posted by a TS / CD

By sissyjamie4daddys

A Business Traveler's Journey of Self-Discovery
Bi, white and married man in my 30's and I used to travel all over the US on business, being put up in nice hotels by my company. I would invite men to my room for sex and gave lots of blow

Posted by a TS / CD

By charleyandsnickers

An Unexpected Night at the Daddy Man's Party
Last week I went to a local group party that was at a daddy mans house. There was 4 other daddy mens there all sitting around with cocks out. I walked over to where they were sitting n got on my

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Meeting at the Bookstore
Another cold night out, but that didn't stop me from going out. I went to a local adult bookstore all dressed up with my ass cheeks hanging out, my tits out floppin, n looking for some cock. The

Posted by a TS / CD

By sissyjamie4daddys

Exploring Local Connections in the 314/618 Area
I love being a cock gobbler for men, n a cum guzzler. I don't waste it, I swallow n taste it. So many daddys have told me their wife or girlfriend don't like sucking cock n def don't

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounters Behind Closed Doors
I enjoy a really good dick down. You know, the kind of dick down where you grab on to the back of the couch, or the headboard n hold on for dear life. Where the daddy mans just pounds n pumps away

Posted by a TS / CD

By sissyjamie4daddys

A Nervous Encounter at the Hotel
My first time dressing as a gurl, I was in my mid 20s. I was to meet a daddy at his hotel. I was a lil nervous bout meeting him, but he promised me a really good time, n did he ever. When I got to

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Encounter with Daddy Mans
I met an older daddy mans thru DL last week. Daddy mans invited me to his place for some sucky fucky time. Daddy mans told me he was very vocal, n liked degrading a sissy like me. Daddy mans called

Posted by a TS / CD

By sissyjamie4daddys

An Unexpected Dinner Party Encounter
So last night I get invited to a daddy mans house. Daddy mans told me he had company that needed to meet me. He told me to dress sexy slutty n to be at his place by 600. It is cold AF so I wore a

Posted by a TS / CD

By sissyjamie4daddys

Unexpected Encounters During the Holiday Season
hi im a community sissy cum dump for my apartment complex i get many loads a day and love it and for Christmas i gave all my top men a Christmas present they came in one by one dumping there loads in

Posted by a TS / CD

By ababycd

A Transformative Night Out in Los Angeles
Hi, the name I go by now is. Joanie ! It was in June of this year 2024, I decided to go on a cross the country for two months and visit some hot fun spots. Where my story starts is in Los Angeles,

Posted by a TS / CD

By johnnie1966

An Unexpected Connection on the Couch
I sat next to daddy mans on the couch as we kissed. Daddy mans tongue working it's way in my mouth, n mine doing the same. Daddy mans hands cupped my titties, pinching n squeezing my nipples. I

Posted by a TS / CD

By sissyjamie4daddys

A Surprising Encounter While Shopping for a Wedding
SISSY HOT WIFE PART 2 My husband and I were invited to a wedding. He was to meet me at the mall for a few new outfits. Of course as usual he was running late. Our pastor from church saw me. As I

Posted by a TS / CD

By littlerockslut

A Journey of Self-Discovery and Acceptance
SISSY HOT WIFE PART 1 Back then loved cross dressing met my future husband we dated for several months. One day he walked in a smile on his face.. he kissed me saying go and take a bath then he

Posted by a TS / CD

By littlerockslut

Exploring Intimacy with New Connections
I met a very passable, shy CD who had reached the point in her transition that she wanted to be with a man for the 1st time. I corresponded with Tanya for a bit before she invited me over. It was

Posted by a TS / CD

By CondorCrest6382

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

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