Story by Desertbiguy
2 Nov 2021 3511 Readers comments 4 Min Read
I decided to dress up as a girl for halloween. There was a big party going on for us jr high kids. And looked good. Maybe to good. Mark was a good looking guy. Something happened at party. He became attracted to me.
Topics: Anal Sex, Crossdressing, Sissy, Halloween
Story by Dickguy4U2
31 Oct 2021 6241 Readers comments 23 Min Read
While well over the legal age of sexual consent, my looks represented a much different picture. Broght up by a single parent overbearing mother, my being raised was far from the normal channels of a lone single male son.With mom making dresses and me the perfect slender size to model her creations, I guess you could say that the soft silk and lace never failed to stimulate me in a secret sexy way
Topics: Crossdressing, Voyeurism, Sissy, Oral & Blowjobs
Story by satyrDaddy
22 Oct 2021 1176 Readers comments 3 Min Read
Bunny webcams with Daddy...and more
Topics: Masturbation, Daddy, Sissy, Verbal, Webcam
Story by BillyBoy
19 Oct 2021 2554 Readers comments 4 Min Read
I meet a cute sissy out for prom night. But he needs a date.
Topics: Crossdressing, First Time, Sissy
Story by satyrDaddy
17 Oct 2021 2866 Readers comments 4 Min Read
Bunny can't wait to cam with Daddy
Topics: Masturbation, Daddy, Sissy, Oral & Blowjobs, Submission, Webcam
Story by BillyBoy
17 Oct 2021 5119 Readers comments 8 Min Read
The title says it all
Topics: Rough Sex, Bondage, Drugs, Sissy, Co-worker, Boss, Throat Fucking
Story by kewlie
9 Oct 2021 6431 Readers comments 11 Min Read
Being used like a queer is a turn on, but being treated like a girl is too!
Topics: Anal Sex, Neighbour, Outdoor, Sissy, Oral & Blowjobs, Fucking, Love
Story by Alleykat
9 Oct 2021 4260 Readers comments 8 Min Read
Seduced at a funeral home by older strangers
Topics: Daddy, Sissy, Verbal, Boypussy, Seduction, Stranger
Story by BillyBoy
6 Oct 2021 3914 Readers comments 10 Min Read
Wife catches me the first time. Very embarassing. But not at all as bad as when she turns me over to the kinky gay guy she works with.
Topics: Crossdressing, Humiliation, Sissy, Oral & Blowjobs, Tricked
Story by Scott Sauce
25 Sep 2021 12418 Readers comments 16 Min Read
Cole is 19. He's short, skinny, and looks young for his age. He's so far in the closet that he doesn't know the way out. He fantasises alone about older men dominating him. Little does Cole know that his step-mom's older brother, Jack, wants Cole. And Jack gets what he wants.
Topics: Anal Sex, Uncle, Enema, Daddy, Sissy, Domination, Submission
Story by Alleykat
24 Sep 2021 12762 Readers comments 4 Min Read
I was blackmailed to be a sissy faggot for old men
Topics: Group Sex, Daddy, Sissy, Blackmail
Story by popperboi
16 Sep 2021 12285 Readers comments 4 Min Read
My first visit to a bathhouse, where I learn about poppers and BBC
Topics: Black Men, Anal Sex, Poppers, Interracial, Sissy, Bathhouse & Saunas, Gangbang
Story by Badman
15 Sep 2021 58832 Readers comments 17 Min Read
Interracial story. A sissy boy meets a cruel mature black man and dresses as a pigtailed girl for him. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties before spanking and raping him. The theme and story line runs parallel to "Sissy Boy Loses Panties To Perverts"
Topics: Black Men, Crossdressing, Rough Sex, Spanking, Daddy, Interracial, Sissy, BBC, Rape, Pig, Panties, Mature Men
Story by BillyBoy
7 Sep 2021 4342 Readers comments 8 Min Read
discovered by my boss and then he makes me his sissy bitch
Topics: Sissy, Hotels, Travel, Boss
Story by Alleykat
7 Sep 2021 4488 Readers comments 4 Min Read
Young pretty sexy hot n horny love public sex
Topics: Daddy, Sissy, Age Difference
Story by BillyBoy
6 Sep 2021 2453 Readers comments 6 Min Read
I remember like it was yeasterday. Girls underwear, being tied up, halpless. I guess I loved it
Topics: Crossdressing, Bondage, Sissy, Lingerie, Panties
Story by BillyBoy
4 Sep 2021 6147 Readers comments 7 Min Read
Well, I fianlly had enough and gave it to him. The little sissy fag
Topics: Crossdressing, Bondage, Sissy, Roommate, Sex
Story by BillyBoy
2 Sep 2021 3140 Readers comments 4 Min Read
I posted some pics of me in my sister's panties and bra. I guess I should have expected to be used like a girl slut
Topics: Crossdressing, Bondage, Sissy
Story by BillyBoy
1 Sep 2021 3771 Readers comments 3 Min Read
She got me hot, he took over from there
Topics: Crossdressing, Sissy, Cuckold, Tricked
Story by Desertbiguy
23 Aug 2021 2612 Readers comments 4 Min Read
I just had my second gay sex encounter. I had sex in a bar parking lot. And met a guy at a fraternity. I was always fascinated with gay street walkers. Getting paid to have sex with gay or straight men. I found a such a street in my college town. I wanted to check it out if i could do it.
Topics: Anal Sex, Straight Men, College, Sissy, Married
Story by satyrDaddy
20 Aug 2021 1400 Readers comments 19 Min Read
Brad becomes Pink and finds his Daddy
Topics: Crossdressing, Daddy, Sissy
Story by Desertbiguy
18 Aug 2021 4694 Readers comments 5 Min Read
I finished up high school. I was accepted into CSU. I had used the bus and dressed up as a sissy to be fucked by men. I got my drivers license. And I was on my way to college. I did not expect to see any dick in my ass during this period of my life.
Topics: Anal Sex, College, Sissy, Bareback, Twink
Story by Desertbiguy
17 Aug 2021 4198 Readers comments 4 Min Read
I started off as a young teen being introduced to gay sex. I had a sexual impulse to act out on them. Having sex in public bathrooms full filed my desire to be an anal slut to men. Then I was curious in becoming a dressed up sissy. And found it more exciting to tease men. My next encounter was with 2 black guys. Enjoy!!
Topics: Anal Sex, Crossdressing, Interracial, Sissy, Twink
Story by Desertbiguy
15 Aug 2021 2149 Readers comments 5 Min Read
Well Juan and crew fucked me outside of town in a grassy meadow. Each took their time to fuck my arching butt standing doggy style. Each pumping their seed deep into my anal vault.
Topics: Anal Sex, Crossdressing, Daddy, Sissy, Twink
Story by Andrew Packs
14 Aug 2021 2017 Readers comments 7 Min Read
My new found love for being fucked by older stranger leads me to an online hook up
Topics: Anal Sex, Daddy, Sissy, Bear, Age Difference, Hookups & Dates
Story by LovebeingJoanne
14 Aug 2021 2483 Readers comments 5 Min Read
I love dressing as a girl, I just can't help myself, every time I would dress up, I would go a little further with my appearance, until the day I realized that I had taken it a little too far.
Topics: Crossdressing, Sissy
Story by Heather_xd
10 Aug 2021 1934 Readers comments 4 Min Read
This is the story of Heather and her life story
Topics: Crossdressing, Sissy, Submission
Story by Desertbiguy
9 Aug 2021 3248 Readers comments 7 Min Read
My life changed after 3 years of being a cumdump for older men. I changed my life to be a sissy gurl. Dressed up to serve horny men. It was a phase In my life that I loved so much.
Topics: Anal Sex, Crossdressing, Group Sex, Daddy, Sissy
Story by bootlicker
9 Aug 2021 3944 Readers comments 30 Min Read
An eighteen year old is sold into slavery by his foster father and trained as a sissy-slut for an older married couple
Topics: Anal Sex, Bondage, Sissy, Master & Slave, Age Difference, Domination, Fucking
Story by Alexlionxxx
18 Jul 2021 5429 Readers comments 26 Min Read
The start of my love affair with cock and in particular, older cock!
Topics: Anal Sex, Rimming, First Time, Daddy, Cum, Sissy, Oral & Blowjobs, Age Difference