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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

Posted by a TS / CD

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

Posted by a TS / CD

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

Posted by a TS / CD

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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

Posted by a TS / CD

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A Playful Challenge Leads to Unexpected Fun

I advertised for a sissy bottom needing filled. Got a response and went to his house. We chatted on the couch for a bit while I stroked him thru his sports. I was wearing boy clothes this time but

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By Deleted User

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A Unique Blindfolded Crawling Challenge

Crawling the gauntlet PART 2 Daddy put the blindfold on me, lifted my lil mini skirt, n told me to get on my hands n knees. I started crawling very slowly down the middle. I could feel leather n

Posted by a TS / CD

By sissyjamie4daddys

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An Evening at the Secluded Country House

There is an old phrase running the gauntlet. The meaning of this is that it is punishment for a person. That person must run down the middle as 2 lines form on each side of this person. It is for

Posted by a TS / CD

By sissyjamie4daddys

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An Unexpected Intimacy After the BBQ

Ray n Tom BBQ part II Tom n I locked into a 69, n Ray lined up behind me, guiding his cock into my asscunt. "That's it baby, take that dick" Ray said as he slid his cock in me. I was

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By sissyjamie4daddys

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A Chance Encounter at the Hotel Bar

I recently stayed at a nice hotel while on business. This is usually the only time I get to dress en femme. This particular time I had a few glasses of wine in my room and got up the courage to go to

Posted by a TS / CD

By Guitarpicker.mb61

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An Unexpected Encounter in a Parking Garage

My ad was simple n straight to the point: looking to suck cock in public. I got several responses n chose a young stud to meet at a downtown parking garage at 6am. I arrived a lil before 6, n hopped

Posted by a TS / CD

By sissyjamie4daddys

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Exploring Connections with Older Partners

I have ALWAYS been attracted to older men, older daddy's if you will. I have a major fetish when it cums to daddys that are 60-90 years of age. I will do anything, n I mean ANYTHING for them.

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By sissyjamie4daddys

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An Unexpected Visit from a Charming Daddy

I met a kinky daddy from here a few days ago. I invited him to my house. The minute daddy walked in, he was a horny dog. Daddy kissed me, grabbed my legs pulled me to him n started humping my legs

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By sissyjamie4daddys

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Memorable Connections Over Labor Day Weekend

Labor Day weekend part:2 Saturday night fell asleep with bbc still inside me.. woke up about 4:45am when he fell out of me.. i felt empty and hallow!! He stretch me out to accept his bbc and i

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A Fun Labor Day Weekend Pool Gathering

Labor day weekend part 1: My name is Sammie.. i am 28yo Asian and black decent.. about 70% Asian and 30% black.. 5’5” and 125-130lbs.. long long black hair that reaches my pussycrack..

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An Unexpected Visit in Bellingham

Good morning Bellingham I call a add on doublelist.com asexy trans wanted me to cum over so I did walked through the door omg she was hot with a long black cock I dropped to my knees and started

Posted by a TS / CD

By DingoKnot6608

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An Unexpected Encounter with Parents at Home

pt2 how my parents found out i was a sissy crossdresser. he started finger fucking me good and then he said open wide i thought he was jerking off and about to cum when all of a sudden he shoved his

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Unexpected Morning Visits from the Neighbor

Every day for the last 2-2.5 weeks, as soon as my neighbors wife leaves for work, her husband has been coming over to get his dick wet. He will come over for a few hours in the morning, get his dick

Posted by a TS / CD

By sissyjamie4daddys

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Adventures at the Local Store

There is an old saying that practice makes perfect. I guess I am now the perfect cock sucking sissy. I have been sucking cocks for 12+ years, and have been a cock sucker on a daily basis. I stop by

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By sissyjamie4daddys

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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 stumptroy “never knew how much i would like it” P pleasure_town “How I found a new taste” L luciecar “Don’t want it to be a boring night” R roosterrogers “Young eager for hours”

Rank	Author · Category	Latest Story	Views	Listens	Upvotes	Trend
#1	derake14 Gay Straight for Gay Couple	The fast and furious	61.9k	868	4.5k	↘
#2	Tiffanyheels Straight Couple Gay	Girlfriend and her attractive daughter	143.8k	2.1k	4.0k	↘
#3	kimorafoxxsexycd Trans Gay Couple	Tall answered my ad	131.6k	1.4k	3.6k	↘
#4	cnysub Gay Trans Straight	Adult Theater	79.1k	711	3.3k	↘
#5	KestrelElbow9092 Straight Gay Couple	Light on Dark	50.6k	522	3.3k	↘
#6	sissyjamie4daddys Trans Couple Straight	I love water	73.5k	488	2.0k	↘
#7	wally4u Gay Couple Trans	I Guess He Did Have To Go!	68.7k	311	2.0k	↘
#8	butchmax Straight for Gay Straight Gay	Well, I Try to BE STRAIGHT	91.3k	641	1.8k	↗
#9	Steve Straight Straight for Gay Gay	Visiting auntie	55.1k	656	1.7k	↗
#10	powers8 Gay Straight Straight for Gay	A fantasy come true	84.1k	671	1.7k	↘

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