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A Day in the Life of a Sissy Gurl

Someone asked me what a typical day is like for a prissy sissy gurl like me. So I thought I would share that with y'all. I usually awake bout 630 in the morning. I have a few cups of coffee n

Posted by a TS / CD

By sissyjamie4daddys

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Awkward Moments in Dating Adventures

I'm a flamboyant lil sissy who simply LOVES pleasing top daddys with my mouth n ass. I have met 1000s of tops for some sucky fucky times. I have loved n enjoyed each cock but I have had my share of

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By sissyjamie4daddys

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A Chance Encounter at the Grocery Store

This happened to me earlier tonight n thought I would share. I was making din din n realized I didn't have enough cheese for my pasta dish, baked ziti. So I drove to my local grocery store to

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By sissyjamie4daddys

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A Chance Meeting at a Rest Stop in NY

It was a rest stop in upstate NY. I took my Girl Bag into the rest room and changed in the stall. Was wearing crotchless body stocking, heels, black lace top and black mini-skirt. I looked good and

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By JaguarCrest3235

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A Unique Bond: Exploring Family Dynamics

"You like that faggot ass, don't ya daddy" I asked daddy as he pounded his very nice 8" cock in n out of my my asscunt. "Come on daddy, fuck me. Slam those balls against my

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By sissyjamie4daddys

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A Flamboyant Crossdresser's Quest for Fun

Hello to all the top men n daddys out there in cyber world. My name is sissyjamie. I am a flamboyant prissy sissy bottom gurl that is a passable crossdresser. I am a 100% complete bottom, whose sole

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By sissyjamie4daddys

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Navigating a Unique Living Arrangement with a Sugar Daddy

I have a rather unique living situation. I am living with a sugar daddy who is married to a female. His wife works out of state 3 weeks per month, n is home 1 week a month. I spend the 3 weeks at his

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By sissyjamie4daddys

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A Weekend Visit with a Charming Couple

So I invited a m/m couple over to my house this weekend for some hot bedroom fun. They are a married couple, both in their early 60s. One is all top, while the other is verse. The last time we played

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By sissyjamie4daddys

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A Sweet Encounter at the Hotel Bar

Sunday night I had a play date with a potential new sugar daddy. He has posted on AFF that he was in town on bizness n was looking for some fun with a bottom sissy who was passable. I replied to his

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By sissyjamie4daddys

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A Flamboyant Journey of Self-Discovery

When I came out of the closet, I came out guns ablazing, n as flamboyant as I could be with bells on. I started crossdressing in 2017, n have not looked back. I started looking for men on Craigslist

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By sissyjamie4daddys

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A Visit to My Uncle at the Retirement Home

I am a attention seeking whore who seeks the comfort of older men. I love to flirt n show off for older men, shaking n wiggling my ass, putting on a lil show for them, n dancing for them.

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By sissyjamie4daddys

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A Chance Meeting at the Adult Bookstore

I go to adult bookstores on occasions when I'm feeling slutty, which is all the fucking time. I can't help myself, I love, LOVE men, their cocks, n their cum. I love swallowing cum. I am a

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By sissyjamie4daddys

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An Unexpected Surprise Visit from Daddy and His Friend

A local sugar daddy texted me n told me to be ready that he was stopping by in a few hours n he had a surprise for me. Well, my lil sissy ass got all dolled up for Daddy n waited with excitement for

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By sissyjamie4daddys

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Unexpected Meeting at the Local Bookstore

Stopped by my local adult bookstore last night to check out some new toys n to see if anybody needed or wanted some company. Ended up in a booth with a nice looking young stud. I pulled his pants

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By sissyjamie4daddys

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A Charming Dinner Date with My Sugar Daddy

So last night I had a date with 1 of my sugar daddys who is in town on bizniss. Daddy took me out to a very nice restaurant where we had din din n drinks. Now, I usually dress very provocative,

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Visitor in the Night

I went to bed bout 10 pm as I had a long day n I was extremely exhausted. Bout 130 in the morning I feel someone crawl in bed n bout freaked me out. I have given a few of my daddy's keys to my

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By sissyjamie4daddys

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An Unexpected Reunion at a Funeral

Up until 8 years ago I was a straight married male who had never been with another man sexually. But that all changed one weekend. I spent a weekend at a buddy's house, and he fucked my ass and

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By sissyjamie4daddys

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An Unexpected Morning Visit from a Friend

I got a text early this morning from a young stud. He told me he woke up with major morning wood n needed to stop by so I can relieve the pressure that was built up. I told him to come on by n I will

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By sissyjamie4daddys

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A Night Out at the Gay Bar: Unexpected Connections

I've been gay and feminine all my life, so at age 22 I decided to become the woman I am. It's been only two years and now I live full time as a woman, but a woman with penis, you may find

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A Dress Fitting Turns Into a Surprise Encounter

part 1 so i was looking for a cute dress for a date this weekend and my sister had got me on Facebook market place and i went looking and before i knew it I found the perfect dress i messed the

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Top Authors

Discover the most engaging creators on Doublelist — ranked by views, listens, and upvotes, with fresh voices breaking in every week.

RISING AUTHORS ON DOUBLELIST See all

S sexysexaddict23 “Made love to my mother in law” F freeusefunholes “Motel excitement on a whim”

akshay “One Message… One Unforgettable Night 🔥”

Obeymyorder “Intimacy in public”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	Tiffanyheels Trans Couple Straight	Crossdresser and girlfriend	78.9k	1.4k	3.2k	↘
#2	KestrelElbow9092 Straight for Gay Gay Straight	Beautiful and Black	24.6k	355	3.1k	↘
#3	cnysub Gay Trans Straight	Ads on DoubleList	48.6k	543	2.9k	↘
#4	kimorafoxxsexycd Gay Couple Trans	New life as a gay man	76.2k	1.1k	2.8k	↘
#5	sissyjamie4daddys Trans Couple Straight	I love water	47.1k	461	1.9k	↗
#6	wally4u Trans Gay Straight for Gay	Pre-Halloween CD Dress Up! Part 1	53.5k	276	1.8k	↗
#7	Steve Straight for Gay Straight Gay	Gym kiss pt.2	49.5k	614	1.7k	↘
#8	curiousladyd Straight Couple Straight for Gay	First really big appendage	10.4k	360	1.2k	↘
#9	powers8 Straight Gay Straight for Gay	Back with Michelle and Lisa	34.9k	354	1.1k	↗
#10	Dedavis Straight for Gay Straight	House hunting pt 1	38.3k	276	1.1k	↘

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