Sissy Bitch Stories

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Sissy Bitch Stories
You have found my stimulating collection of sissy stories! All have been submitted by real people wanting to share their stories with the lovely people who read my blog. So whether you’re a sissy yourself, curious about the fetish, or you want to try being a sissy out these stories will not just give you a great idea about what goes on behind these sissies closed doors but also they will turn you on like never before.
A man with a BBC wants to choose one of his favorite sissies and cum deep inside of her and try and get her ‘pregnant’. In this submission you can read all about how and who he chooses and what their alluring meeting is like and let me just tell you this, it’s seriously hot.
A wife and her husband are training him up to become the ultimate sissy. He has a long way to go but in this story, we get to learn all about how he is getting used to male cum and what he and his wife do to get him prepared for taking his first-ever real load.
An eager anal virgin sissy wants our protagonist to be her first. We get to feast our eyes upon their first meeting and the first time she gets her ass penetrated. It’s exciting to read and a real thrill between the legs.
A husband and wife duo decides it’s time for her husband to be transformed into the sissy he has always wanted to be. You can read through their transformation, the sexual journey they took, and maybe even get some tips for yourself.
Love BBC stories? Well, this one has a bit of a twist. We get to ride along with this well-endowed hunk as he takes us on a journey of breaking his sissy partners in with his large member. It makes you crave being a fly on the wall at one of his meetings.

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Favorited by sissy2control , ltpulk2 , Red10Dog and 8 others
Neighborly Love But Blackmailed! Better remember what your wearing when you leave home.
Hubby's Sissy Training Day!! Told my wife about my fantasy's and I woke up dressed!
A Slut is Born Young man forced to be a woman
Straight Crossdresser Guy dresses as a girl on Halloween & ends up performing as one.
I Love my "My Cum Slut" Dressing up for my Daddy is fun!!
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This is a story from the sissy's wife. Telling you a story that happen a few weeks ago and it was orgasmic!
So late one Saturday night I put my sissy bitch in a teddy, nylons, cock cage and a jeweled anal plug under his pants and shirt and headed out to the casino.
I am not ready dress him out in public yet, but I am getting close.
I decide to slut myself up too. I wore my high heel black boots with a tight black miniskirt and white blouse and done my makeup very sexual.
I never dress slutty out in public like never, but I was just feeling daring.
I put a pink dog collar on him with a pink leash and went to the casino. It was after midnight and they packed the place.
Everyone was taking the sight of me dressed up and walking my sissy bitch by his leash through the building.
As we were putting coins in the slots. An older guy walked and chuckled, touching the leash.
He asked me if I was showing of my bitch? I laughed and said "Yep I sure am!"
Then he asked me if he could abuse my bitch for a while.
My lips got dry and my mouth fell open and suddenly I said "Yes you can!"
He grabs my bitch's leash and told us to follow him.
When we got to his room, he told us he was from Louisville and up for business and that he just turned 60 a few days ago.
He asked me to sit in the chair politely so I did. He turned to my bitch and commanded him to get undress.
My bitch took his shirt off when the older gentleman saw him wearing a teddy. He says to him "Keep your sissy clothes on!"
My bitch was standing there dressed as a sissy in front of this man scared. The older guy gets naked. I look at his crotch and noticed his cock was an average size but very hard.
I unzipped my boot when he stops me and said. "Please don't get undressed! I will get very rough. I need to get very rough and you're an exquisite and polite young woman I don't want to abuse you please!"
Me being confused and horny, but I did as he asked.
He laughed seeing my bitch's caged cock and jeweled anal plug. He yanked my bitch to his knees and abused his mouth so fucking hard. His actions and watching this live porn in front of me mad my panties wet.
I reached down and felt my panties. I soaked them watching him fuck his face hard.
Tears rolling down my bitch's face combined with his slobber covered his face. The sight of watching this I had to finger myself.
I closed my eyes and started playing with my clit. The sounds of my bitch gagging sent me over the edge as I cum.
This older gentleman was not kidding when he had a lot of aggression.
Then this guy turned around and told me to shove my bitch's face in his ass and make him lick it.
So I got up and pushed my bitch's face between his ass. I had to laugh, my bitch was loving it and so did this old guy.
After all the moaning from these two. The gentleman asked me to sit back down. He put my bitch on his hands and knees facing me. He made my bitch look into my eyes telling me to watch his masculinity leave his body.
He had me put my bitch's head between my legs and under my skirt. The guy told me I had to leave my panties on he wanted this bitch to smell my pussy not be able to lick it.
I watch him take the plug out of his ass and ram his cock deep into his asshole.
I sat and watched his cock out of my bitch's ass, while he kept saying his masculinity is leaving with every stroke.
I felt my bitch's warm moans on my pussy. It sent me over the edge as I cum without even touching myself!
The gentleman reached up and squeezed my tit very hard once and then went back pounding my bitch's ass hard. Pushing my bitch's face into my pussy.
I could tell this old guy was getting close to cum. As he stood up stroking his cock, he grabbed my bitches collar and shoved his cock deep into my bitch's mouth.
I watch his balls tighten up as he grunted. I could not see his cock throbbing cause he pushed his cock as far as he could down my bitch's mouth, but the balls looked tight and that made my pussy juices flow from my pussy again.
Holy shit, the sight of watching my bitch get abused was more enjoy watching a live porn, and it was better than sex.
But I was horny too. He pulled out his cock and shot one load on my bitch's forehead and smeared it around.
He told my bitch to kiss his feet. I watch my bitch crawl over to him and kissed his feet, thanking him. He told my bitch to get dress, and it was time to leave. I felt so empty and I wanted fucked too!
My bitch asked if he could use the bathroom and he was told no and we had to leave right now. So I told my bitch to hold his clothes, because he didn't need them no more.
I held my bitch's leash when the older guy gave me a passionate kiss on my lips thanking me.
I made my bitch walk in front of me wearing nothing more than a teddy and nylons and his cock caged. I carried my bitch's anal plug in my hand.
I told my bitch to enjoy the walk of shame and be proud. I watched peoples jaws drop and laugh at him as we walk down the hallway to the elevator.
We got in the elevator I shoved my bitch up against the door as we headed to main lobby. I kissed his neck and moved his panties to the side and shoved his jeweled plug up his ass.
The door opens and 6 people standing waiting to get on the elevator jaws dropped and laughed as we walked out. I had him walking outside on the frozen road wearing nothing but nylons on his feet.
As we started the car, I realized we left not knowing his name or exchanged no number with each other, nothing.
I got my bitch home and unlocked his cock and told him to fuck me hard cause I needed cock.
His panties soaked as well from his pre-cum all night long. His cock was so hard and ready but with only two fucking strokes he came.
I was so fucking mad I beat him with my whip. That bitches ass was so read what seemed like a hundred swats. Then I made him lick his cum off me.
Then I put my strap on and attached it to his fucking face as I rode his face so fucking hard and came 5 times over and over cover his face with my cum. My pussy was sore for days from riding that fake cock. I made him worship my pussy every day.
Next time we go out, he is fucking watching as I get to enjoy cock! Damn him!
Seeing live sex in front of me was the most exciting thing I ever seen, it was just as good as sex seeing my bitch get used!
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GayDemon's Stories: On this page you can find erotic fiction where you can read about men dressed and made into girls and sissification listed by date.
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The Rest Stop Digest . This is one of many stories I have written through out the years.
Most of these stories are real experiences. Some of these stories are
about different people, but they are based on real event and told as close to a
Accurate as possible. This is a true story but the names have been changed ..
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Although this is ch 4 , it is the 2nd part of the Jill Jordan story.
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White boy thinks he's gonna get lucky with hot black woman.
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15 Sep 2021 31504 Readers 2 comments 17 Min Read
Interracial rape story. A young sissy boy meets a cruel mature black man and dresses as a schoolgirl for him, he gets spanked and raped. The cruel man treats the little sissy rough, tearing off his clothes and ripping apart his favourite little white cotton school panties. He forcefully spanks him hard then rapes 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
7 Jul 2020 18758 Readers 1 comment 13 Min Read
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21 Dec 2019 24293 Readers 3 comments 28 Min Read
2 blonde bimbos help a little sissy faggot become the girl he always wanted to be and Introduce him to a man who knows just what to do with a special girl like this!
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7 May 2018 23191 Readers 7 comments 3 Min Read
After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.
Topics : Black Men, Crossdressing, Sissy, Drunk
9 May 2018 17922 Readers 2 comments 2 Min Read
After fighting with a drunk girlfriend, a boy is fed up with women. He decides to finally live out a fantasy he's had for years.
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The neighbor boy finds neighbor Daddy
25 Jul 2016 47059 Readers 3 comments 15 Min Read
Sissy boy loses the game, now he's going to lose his anal virginity.
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My first visit to a bathhouse, where I learn about poppers and BBC
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17 Apr 2022 4055 Readers 5 comments 36 Min Read
Continues the journeys of two brothers months after the events of Part One. Darren and Randy both find themselves beginning a new chapter of their lives with new and old friends.
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I go to an adult bookstore for my first time while dressed as a Gurl and get my first sex with men, lots of men. sissy, first time, spanked, DP.d, oral, anal, domination, sexy, slut
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31 Oct 2021 3996 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
9 Oct 2021 3822 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
15 May 2020 9185 Readers 3 comments 2 Min Read
Topics : Black Men, First Time, Sissy, BBC
9 Jan 2022 4455 Readers comments 20 Min Read
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28 Dec 2019 7826 Readers comments 10 Min Read
A gay sissy bottom receives a surprise birthday gift
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24 Sep 2021 6374 Readers comments 4 Min Read
I was blackmailed to be a sissy faggot for old men
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My gay lover left me but not before he turned me over to a gay Dom Master. I guess I should have been more careful of what I asked for.
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One of several kinky bondage games the boys like to play.
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Adam MacDonald secret life of crossdressing has always been both the escape and high of his life. A mysterious package with no sender address arrives one day, and inside it contains: a dress and more!
29 Nov 2018 23727 Readers 4 comments 22 Min Read
Charles has battled against his feminine features all his life. It takes a single experience with a dominant, alpha high school jock in the locker room to make him know his place in the world. ! ARCS Needed !
Topics : Anal Sex, Crossdressing, Public Sex, Locker Room, Transgender, Sissy, High School, Twinks, Oral & Blowjobs
29 May 2020 1939 Readers 2 comments 3 Min Read
Dear Rears I really struggled with the decision to allow the Pandemic to be an element in my story. But I am writing a story about a cute sissy that lives in Detroit which has been impacted heavily and so I included it.
Topics : Anal Sex, Crossdressing, Big Dick, Romance, Sissy
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Man is drugged, then dressed up and trained to be a slut.
Sissy watches as his son screws his wife.
Wife fullfills husbands desire to be a cuckold.
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A wife joins her husband as a slut for a teen BBC.
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Straight guy watches porn tapes that are not what they seem.
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I get turned into a sissy by my younger sister.
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Young man entranced by BBC, is pushed to be a sissy.
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A detailed feminization of a sissy.
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The slut in training falls deeper into the predicament.
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Ex discovers secret chastity fetish while dating new BF!
Tommy plays dress-up and gets caught by his neighbor.
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Nathan is unwillingly trained to become a sissy slave.
Sister seduces brother when he comes for a visit
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She dominates, sissifies & cuckolds her boyfriend.
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He's captured and mind-fucked into becoming gay.
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The Old Bull takes the husband by force.
They find out what I've been doing.
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