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A Weekend Visit from My Sugar Daddy

One of my sugar daddys is in town til the weekend! I am a very happy gurl. I haven't seen this sugar daddy in a few months. But he is in town til Saturday morn, n I plan on making the best of

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Connections at a Budget Motel

I'm a 60 plus years old white man who loves ❤️ wearing dresses 👗 😍 and visiting cheap motels and place ads searching for eagerly hung black men. The first time I eagerly opened my

Posted by a TS / CD

By olderwhitemale

0

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An Unexpected Invitation to a Private Pool

So I work at my local grocery store that a sugar daddy owns. I have free roam to do what I want, as long as I'm professional bout it. The other night this m/m couple came in. I had the pleasure

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unforgettable Night at a Bi Party

Im a submissive Crossdresser for starters. I wanted to share one of my favourite experience that I wish i could do again. First off I love anonymous sex. There’s just something about it

Posted by a TS / CD

By sissysammiecd

0

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A Cozy Friday Night Visit with a Daddy

It's been a very lovely Cocktober so far. The weather has been simply fab, nice cool brisk mornings, warming in the afternoons, n chilly during the nights. Nice weather to snuggle n cuddle with

Posted by a TS / CD

By sissyjamie4daddys

0

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A Journey of Submission and Connection

I am a submissive prissy sissy whose responsibility is to please any man that needs to be pleased, via my mouth or my asspussy. It is my sole purpose in life, my honor n privilege to suck n fuck

Posted by a TS / CD

By sissyjamie4daddys

0

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A Transformative Night Out: Embracing Change

FINALLY I GOT LAID! Occasionally as a kid I'd play with my step sisters sexy panties. I chocked it up to normal prepuberty curiosity. Later in my 30's the urge returned to dress up like a

Posted by a TS / CD

By Deleted User

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Navigating a Life-Changing Proposal from a Sugar Daddy

I have a slight problem. I have several sugar daddys that I see on a consistent weekly to monthly basis. Most are married n live out of state, n I see them maybe once or twice a month. Well, one of

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Visit from the Pizza Delivery Guy

I was sitting on the couch curled up with a good book when the doorbell rang. I got up to see who it was. There was a young stud on the front porch holding a pizza box. I told him that he must have

Posted by a TS / CD

By sissyjamie4daddys

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A Charming Day of Sightseeing and Connection

Mr D part II When I got back to my hotel that night, I played with my 9" dilly, riding that motha fucker wishing it was Mr D's cock. The next day Mr D calls me n invites me to do a lil site

Posted by a TS / CD

By sissyjamie4daddys

0

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Reconnecting with a High School Crush

Back in high school, I used to have a crush on Mr. D. He was my us history teacher, n he was very sexy. I would sit in class n fantasize bout him a lot! I would have given anything to get under his

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Encounters in a Family Setting

when I was still living with my parents I would rush home from the bus stop go into there bed room look at my dads playboys n play with myself. one day I read an article about different male self

Posted by a TS / CD

By bisexpantyboy

0

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A Weekend at the Sugar Daddy's Party

I got a call from a sugar daddy that lives out of state, bout 4 hours from me. Since it is Cocktober, he invited me to a lil group party he was having at his place right outside Louisville KY. Daddy

Posted by a TS / CD

By sissyjamie4daddys

0

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Unexpected Connection During Office Lunch Break

So I work at an office where it's mostly men. There is this cute guy that has been there for a few weeks. I got the vibe that he might be gay but no evidence. That changed last week. Now I am a

Posted by a TS / CD

By sissyjamie4daddys

0

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Exploring Connections with Older Men

I have a soft spot on my heart for older men. Especially if they have a raging hardon. Hell, I have a soft spot for ANY n ALL men from 18 years of age to 80ish who have a bulge in their pants n know

Posted by a TS / CD

By sissyjamie4daddys

0

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An Unexpected Visit from My Sugar Daddy

One of my local sugar daddys stopped by bout 10ish Sunday night for a lil sucky fucky fun time. This sugar daddy has a very nice sweet tasty n delish cock. N he has some stamina! I greeted him at the

Posted by a TS / CD

By sissyjamie4daddys

0

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Preparing for a Memorable Encounter

A few years ago, I met a older daddy off Craigslist, back when they had the casual encounters section. He invited me over to his place. Now, I believe in cleanliness, having really good hygiene. I

Posted by a TS / CD

By sissyjamie4daddys

0

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A Unique Journey of Self-Discovery and Connection

I am a passable crossdresser. I love sexually pleasing top daddys n young virile studs. It don't matter to me if they are married or single, white, black, straight, bi or gay, if they are

Posted by a TS / CD

By sissyjamie4daddys

0

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A Blindfolded Encounter with Unexpected Guests

So I've recently got into wearing sexy panties and thigh highs for older men who want a sissy slut bottom. I'm 37, men in their 50s and 60s turn me on. I responded to a post looking for a

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A Night of Transformation and Connection

BOB TURNS INTO ROBERTA PART 2.....I started working my cock in and out and he told me I was making him feel so feminine, he said he loved to get fucked. I guess I lasted about 15 minutes before I

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#1	derake14 Gay Straight for Gay Straight	Parking lot kiss	35.1k	634	4.1k	↘
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#3	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	24.1k	355	3.1k	↘
#4	cnysub Gay Trans Straight	Ads on DoubleList	47.9k	530	2.9k	↘
#5	kimorafoxxsexycd Gay Couple Trans	Very kinky self care	74.6k	1.1k	2.7k	↘
#6	sissyjamie4daddys Trans Couple Straight	I love water	45.8k	461	1.9k	↘
#7	wally4u Trans Gay Straight for Gay	Pre-Halloween CD Dress Up! Part 1	52.7k	275	1.8k	↗
#8	Steve Straight for Gay Straight Gay	Gym kiss pt.2	49.2k	612	1.7k	↘
#9	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.3k	360	1.2k	↘
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