by
SissyHubbyD
on Aug 7, 2019
Transgender & Crossdressers
His alarm goes off at 6 AM that Saturday. On any other Saturday he would ignore the alarm and sleep in until 10 or 11, but not today.
Today is Service Day, and he couldn't be happier about it.
He gets out of bed quietly, careful not to wake his wife as he does so, and tiptoes out of the room and down the hall to the empty guest room. His outfit for the day...
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- 3 Comments
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by
SissyStoryTime
on Nov 20, 2018
Transgender & Crossdressers
This is Part 1 of an update on the sissy Sophie and her cruel but loving Mommy, Amanda from the story Meeting Mommy (https://www.literotica.com/s/meeting-mommy)
It contains numerous perverse and offensive themes that I'm sure you'll all eat right up.
This story includes the following: Femdom, strap-on, implied forced-bi and cucking, enemas, butt plugs and...
- 47,227 Views
- 42 Favorites
- 4 Comments
- 5,620 Words
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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...
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- 64 Favorites
- 5 Comments
- 11,380 Words
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by
lockedupslut
on Sep 13, 2017
Transsexuals & Crossdressers
(This story is a work of fiction. If you don't like erotic stories that contain cross dressing, heavy gay themes and water sports please just don't read it. Thank you.)
*
I was determined. This weekend it would happen. I would loose my gay virginity and complete manhood. The hard way. Tonight would change everything.
Until now I've never had sex with a ma...
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- 11 Comments
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by
madetoobey
on Jul 10, 2019
Transgender & Crossdressers
Reprise: I'd been caught wearing my Sister-in-law's underwear and jerking off to shemale porn by wife (Ruth), Sister-in-law (Esther) and their mother (Donna). Ruth, as a part of my punishment, was setting me tasks until Esther (who'd taken my laptop and mobile phone) could verify I'd never visited such sites before. I'd been forced into a chastity cage and m...
- 9,897 Views
- 5 Favorites
- 2 Comments
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by
kendra13
on Feb 13, 2018
Fetish
I am a blue collar manager type and live a pretty work a day life during the day, but at night, I have a rather interesting sideline. I am a sissy trainer. You see, many sissies are married and end up coming out to their wives. To most couples, this just creates a fun little fantasy for play during sex, but for some, it becomes more. For these couples, at so...
- 27,332 Views
- 15 Favorites
- 6 Comments
- 990 Words
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by
pantywriter
on Oct 9, 2018
Transgender & Crossdressers Stories
The transition from sleep to wake came rather early for Larry the following Monday morning. He rolled over and sat up, and winced as a blinding flash of pain hit him. "Owwwww fuck me," he moaned as he quickly adjusted his sitting position. When he stood it was slowly and carefully, and it wasn't until he had walked through his apartment getting ready for Mon...
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- 29 Favorites
- 2 Comments
- 6,047 Words
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by
LindseyAntoinette
on Nov 26, 2019
Transgender & Crossdressers
"Ugh, I messed it up again," I groaned as I tried, once again, to apply a bright shade of red to my lips. My manicured hands had been shaking all night as I got myself ready. I finished off my cherry red lips with a layer of gloss and took a step back from the mirror to review my handiwork. My grey smoky eyes and red lips shone against my pale freshly shaven...
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- 44 Favorites
- 3 Comments
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Transgender & Crossdressers
Chapter 15
Only 10 minutes had passed since they left from the homeless shelter and they were already pulling up in front of CC's. Mark had had no time to process the humiliation he just experienced yet while he was already getting confronted by a whole new sense of dread creeping up to him. He knew Lisa meant well, but he was also sure she would get corrup...
- 17,750 Views
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- 9 Comments
- 6,624 Words
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by
NancyPan
on Sep 14, 2017
Fetish
This story will likely be most enjoyable if it is read after reading The Domme Club and one or two other stories in the series (for background of Tom and Monica's relationship and how Tom has previously been humiliated in front of the Domme Club.) Respectful comments are appreciated.
*****
Mistress Monica left Tom the standard list of chores to do while s...
- 19,227 Views
- 16 Favorites
- 1 Comments
- 3,102 Words
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