Sissy Pegging Stories

Sissy Pegging Stories
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Meeting old friend in San Fran, Jeri's dad is a cuckhold.
Beth is hypnotized, Miranda delivers.
Mistress punishes and pegs Her slave over morning coffee.
Rory goes to College, and finds help in an usual way.
Our first weekend together continues with a friend.
or, "How my dildo-whore got his name"
I got caught in a compromising position at the local clinic.
Tom endures more torment, but is offered a way out.
Wife fucks crossdressing hubby with squirty dildoes.
A sub wakes up her dom with a blow job.
Nick is a selfish lover, however, he didn't realize...
A woman impetuously succumbs to a younger man's attentions.
Our online lovers meet for the first time for kinky fun.
The week gets off to a good start for Jack and Phoebe.
Initiation Rites and the Theory of Pleasure.
More hypnosis! The sorority gals love their fucktoy.
A young woman develops with 'a little help from her friend.'
Mistress Kristy's second session with Vic.
Straight guy is lead unexpectedly into his first experience.
Ashley's plans for Dolly are interrupted by Rose's return.
Erotic Bedtime story for all the good girls and boys.
Markus pursues Shireen. Darius fully embraces sissy slavery.
A widowed business woman finds comfort with an employee.
Ray comes through on his promise to Nate about Kerri.
Domme helps male sub find the release he needed.
A young employee is invited to a very special dinner.
Can a small penis dude make it as a porn star?
Continues the adventures of the Bubblegum Princess Inc.
Hubby's busty old flame returns for an encore.
My first experience with a Domme and her neighbors.
Analisa continues her sexual awakening.
Because, after all, what's mine is.
The bet between the siblings comes to an end...
# when good neighbours become good "friends"#
Danny picks the wrong place to cheat.
Paying the Price. Mistress Eliza shows me my new role.
Taboo relations lead to Mindy telling all to her diary.
Tom hurt Jenny's feelings, and now someone's playing games.
Queer lust. Punk rock. A study in contrasts.
A ranger finds a young lady with a secret in the woods.
Ann and Jamie meet Herman’s surprise guest.
Tony has a threesome and is punished.
Brick's ex comes to help Laura and Phillip.
To succubi, fantasies are invitations.
My long-time crush has a big surprise for me!
A subscription box delivers a sensation-sharing cream...
My best friend adviced me to strapon fuck my boyfriend.
A strange creature washes up during a tropical storm.
My first introduction to getting pegged and becoming a bttm.
They believe he's the devil. He's about to prove them right.
The goddesses take turns & the slave suffers manifold (1/2).
Aaron and Sophie reach new heights with co-parenting.
I get some Pegging practice in for my mommydomme...
Mistress and her assistants reward Stephen with release.
The Gamma girls continue molding Dolly to their will.
She wondered, before he fucked her ass, could she do his?
Yet more spanking, paddling, and pegging of the bad boys.
Femdom dominates and plays with cute boy.
Mommy degrades, uses, and then builds up her submissive boy.
Couple takes a chance with their swinger neighbor.
A quick story about some kinky fun at the end of the night.
Wife fulfils husbands sissy fantasy..and some!
More fun with Megan and Bonnie in our MFF.
Learning to serve an experienced Mistress.
Cherry uses her skills to help our wounded warriors.
She gets a golden shower after she pegs him.
Ron becomes Roxette and serves as a plaything.
Sean ventures deeper in the domain of Femdom decadence.
Can Andy finally find Kate at the Halloween Sex Party?
Found myself taking the pharmacist's strapon.
*Wishing = When I Spank Her I'm Never Gentle.
A new sissy's first time with the fit MILF next door.
Aiden fantasizes about a classmate.
Dolly goes to Girliness Bootcamp, and meets an old enemy...
Life of an Earthling being raised in an Amazonian planet.
Zoe adds to her collection of slaves.
Lou and Molly head west and meet new friends.
The Inquisitor must face a demon from his past.
Nicole gets in and out of trouble; Kate helps out.
Joseph tries to be helpful, but gets pegged instead.
Hally invites a friend over to help her humiliate Madison.
John's first trip to Monika's student abode.
The couple dabbles in some Non-Traditional relationship.
Cis male switch gets surprised by hot girlfriend.
Natasha's cousin and their friends have some fun and leave.
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Now normally, I would continue on with my story about rough lesbian sex at formal with my sister, but I think I should take some time to introduce my love of pegging. Now technically, what I was about to do with my sister was not pegging. But pegging sissy boys – oh, how I love it. I first started pegging sissy boys as a favor to my boyfriend at the time.
My boyfriend at the time (we’ll call him Chad) was the Pledge Master for his fraternity. He was in charge of their rewards and punishments. That wasn’t his main job, but it was an important one. He took this part of his job very seriously. He was pretty creative and he included me in both his rewards and his punishments. It was not uncommon for me to receive a text from Chad in the middle of the day in which he would tell me to report to the fraternity house closet.
The closet was the room of rewards. In this closet, pledges received their reward from me. Usually I’d suck them off. Sometimes if Chad said they’d been extra good, I’d let them fuck me. I didn’t mind this, but the punishments were what I most looked forward to. You see, Chad wanted to remind his pledges of their place, and if they misbehaved, their place was at the bottom. Or, being the bottom, I guess is a better way to put it.
The night it all started, Chad and I were on a date. He told me he had a present for me and I was so excited. When we got back in his car, he pulled out a strap-on dildo with a bright pink bow around the tip. I got confused. A week before this, I tried to finger Chad’s ass while I blew him, and he did NOT like it. I guess I thought he got me the strap-on so I’d play with my sisters in front of him?
Nope. He did hate me attempting to put a finger in his ass, and that gave him a great idea for a punishment. If he hated having a finger in his ass, he guessed most guys would hate it too. And if they hated a finger, then they would definitely hate a cock. His new punishment? I was going to peg the pledges who disobeyed him. To quote Chad: “If they’re gonna act like a little bitch, then they’re going to get fucked like a little bitch.”
The closet was the room of rewards, so the pegging sissy boys didn’t take place there. Instead, I pegged them in the basement. They knew the drill. Chad just had to tell them to report to the basement so when I arrived, they’d be on their hands and knees. Usually, they’d be fully clothed, because part of their punishment was stripping for me. Apparently, stripping before pegging is humiliating to them. Anyway, I’d come down into the basement and tell them to get naked. I’d watch this happen and usually cheer for them. Or I’d boo them – whichever seemed to embarrass them more.
Once they were naked, I’d use a squirt bottle to spray lube onto their assholes. They were responsible for reaching back and spreading their asscheeks. If they didn’t spread them wide enough, then I wouldn’t get the lube where they needed it. It only took one sissy boy messing up one time before they learned. I didn’t care if it hurts or not and Chad didn’t either. Pegging sissy boys wasn’t all about pain. It was also about humiliation. If it hurt, that was just an added bonus.
The first time I tried pegging sissy boys, I was very timid. Chad sat in the corner and cheered me on, but I was still nervous. I was used to being penetrated, not doing the penetrating. All in all, I was looking forward to it. I liked the idea of being dominant, and pegging sissy boys definitely let me do that!
The boy was on his hands and knees and had his ass up in the air. I was familiar with that position, so I sympathized with him. Your knees can really start to hurt. Anyway, we got him all lubed up and then I put a drop of lube on the dildo. I pushed just the tip in first. He moaned so loud that I think both of us were surprised! He liked it though, because he begged me to push more of the dildo in. I didn’t. This was a punishment after all.
Instead, I took the fraternity paddle Chad offered me and brought it down hard on his ass. He yelped and pushed back against the dildo. By pushing back, he took another three inches of the dildo up his ass. He moaned again like a little slut and begged me for more.
I’ll admit I enjoyed the power. I pushed the rest of my strap-on into his tight ass. He groaned and I watched him grab at his own hard cock. I knew then that I was pegging a sissy boy who got off on a cock up his ass. I fucked his ass so hard that my thighs were sore! He came all over his hand and while I didn’t come, I did enjoy myself. I do think Chad enjoyed watching me pegging sissy boys because his cock was rock-hard.
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by daddyslittlebitch
on Sep 14, 2017

by whiteboibbclicker
on Sep 16, 2017

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DISCLAIMER: This story is about Femdom, Cross Dressing and Cuckoldry. If these topics offend you please don't read it... Just move on. No need to vote or comment if this isn't your "thing". If these appeal to you, please enjoy.
*****
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