Butt Plug Bondage Stories

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Orientation
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AliExpress and Sissy Downfall

by His_fag_wife on Oct 15, 2017
Transsexuals & Crossdressers

It all started with a visit to a TV Mistress on a work trip, Charlie had been cross dressing in some way or another since he was a teenager. First just his Mums used panties, then a lodgers underwear and finally he'd started to buy the odd thing himself. As time went on, BDSM was added into the mix, Charlie realising he was submissive and when he found Siss...

Fun with a Cherry Popper

by Floydman1 on Jul 2, 2018
Transsexuals & Crossdressers

Quitting time couldn't come fast enough. As soon as I had seen the notification of delivery, I couldn't concentrate on anything but what was inside the box, waiting for me at home. Finally! I was legal as I drove home, but barely. I had just managed to duck a conversation that was guaranteed to take at least an extra fifteen minutes. While I didn't brazenly...

Connie Finds a Kinky Boyfriend

by cmorehead on Sep 16, 2017
Transsexuals & Crossdressers

Disclaimer: The following story is not intended for minors. If you are offended by sexually explicit material or it is not legal in your place of residence, please close the document now. If not, I hope you enjoy my attempt at entertaining you with stories of my adventures. For those of you who have read my other adventures, this story is will be told in a...

The Chair

by Fauna on Sep 17, 2017
BDSM

I watched your breathing change after I put the blindfold on you. Your arms were bound behind you. You looked so strong, yet so vulnerable as you sat there. The white ropes against your tanned skin seemed to glow. Each cable placed so carefully around your chest, binding you to the chair. You didn't struggle. You didn't move. You didn't even shift your bo...

My First All Male Rough Gangbang!

by MrJimJim on Sep 13, 2017
Group Sex

I was so... So nervous! I mean, after all, it's not every day you're going to have 19 of the biggest black cocks of all time over for a gangbang! So I leave work early. I stop at the liquor store for booze for mixed drinks. I stop at the porno store and buy a medium sized butt plug, all 4 of the 'size queen' DVD's, 3 12oz tubs of anal lube, a ring gag, som...

Club 35

by Gln1517 on Oct 13, 2017
BDSM

This story contains a number of different elements; BDSM, bisexuality, group sex, bondage, anal, lesbianism and homosexuality. If these topics upset you, go away! If they don't, enjoy. ***** Jennifer Lowe was a successful woman. She ran a medium sized advertising agency that a few years back was a very small advertising agency. She had a staff of 22 and t...

An Ever Changing Story

by Helenthemaid on Sep 16, 2017
Transsexuals & Crossdressers

Caught Out and Permanently Punished I was wearing a ultra short black leather mini skirt, a tight leopard print low cut top, which revealed my cleavage entrapped by my pink lacy bra (with matching panties). The straps of my 6 inch leopard stiletto heels were securely padlocked around my ankles. Recently I had been often going to the local park dressed in...

The Ad Pt. 03 - My Debut

by Sustainer on Oct 12, 2020
BDSM

Oh God my cunt. My delicious, delicious cunt. Someone was eating my cunt and it was divine. Beyond divine as their wet tongue gently lapped my inflamed and yearning clit. I think it was a girl, but I couldn't see because of this damned hood. But I felt long, soft hair on my thighs above my stockings. Only another girl can give oral pleasure like this, ca...

Michelle's Hotel Bondage Experience

by michellelakes69 on Sep 13, 2017
Transsexuals & Crossdressers

As a timid and closet cross-dresser, my biggest fantasy was to have a sordid meet in a hotel room, where I left what happened up to another person, with only major limits discussed and agreed first. After months of search and waiting for the right person to come along, I finally met 'Sylvia' online, and I had finally decided to take the plunge to meet up wit...

Marie's Perfect Breasts Ch. 07

by Tdisk on Sep 19, 2017
Fetish

Marie and Nancy had arranged to take several days off from work after being fitted with their corsets. This was to allow for Mary's suggested settling in period. Mary had said that wearing the new leather continuously for 36 hours would improve its long term fit. Marie suspected the real purpose was psychological. It was to play with the wearer's mind so she...