Cross%20dressing Stories

43,513 results
Orientation
Length
Source
Infinite Scroll

Summertime Cross Dresser Confession

by andtheend on Sep 14, 2017
Transsexuals & Crossdressers

After a long time coming, a lifetime of suffering, the first day of summer is when an aging cross dresser finally gives into the life he's always wanted to live. As if a new beginning, as if being born again, Donald looked to his transformation from man to woman, as his emergence from moth to butterfly. He couldn't wait to fly away to start his life anew. P...

The Debut Continues

by MayhemLass on Sep 15, 2017
BDSM

This is the next chapter following my story, The Debutante The crowd parted as Lydia led the now leashed S. through their ranks. Her great eyes met no-one's but turned inward as S. hugged to herself D.'s parting kiss, his unspoken promise which she believed with every fibre of her being. Unconsciously, she straightened her strong shoulders, the small breast...

Beg to Please Me

by Mistress_Athena on Jul 27, 2020
BDSM

Restraining you the first time was a mistake, Slave. Now it's all I can think about. I want us to scene in the dungeon; I want to watch onlookers' enraptured looks in the mirror as I show you off. You mark so beautifully; you whimper so prettily. You are breathtaking. I want to see you on the St. Andrew's Cross, facing me and restrained by the same heavy...

DEV© - St Andrew's Cross℗

by smotp on Sep 17, 2017
Text With Audio

Bondage, restraint, forced orgasm, sensual pain and discipline as well as some intense sex and release are at the core of the St Andrew’s Cross audio experience. Not so much shades of Grey, more into the Darkness. Tread carefully. Directed Erotic Visualisation© or DEV© is an audio technique that works on the part of your brain where your sense of pleasure a...

Cuckold Ch. 08

by Sammi_the_Seal on Apr 21, 2020
Loving Wives

Melissa I threw my suitcase down on one of the chairs in the fairly empty hotel room. Even though it seemed like we only met up in hotels, Patrick never seemed to bring anything with him. The area itself was always so clean. "Come here, little one," Patrick said as he slowly came up behind me. His hot breath on my neck made my skin tingle with excitement....

A Practicum in Sensual Awareness Ch. 05

by vmystere on Sep 13, 2017
BDSM

Diana tried her best to think of something: anything, that would take her mind off what was happening — it did not work. As soon as she started trying to rationalize her predicament, the tawse fell on her backside and she tried to quicken her pace. If it wasn't the incessant whipping she was receiving, it was the constant brutal motion of the phallus within...

The Office Ch. 07

by EasilyConfused on Sep 14, 2020
Transgender & Crossdressers

The instructions had been concise, anything more detailed and it was highly likely that they would have been forgotten or led to unnecessary confusion. "Do you understand?" "Yes Ms Smyth," they each chimed. Not completely in unison but the solidarity was sufficient for Tracey to be satisfied that each understood their role. Tonight the trio were to be esc...

A Mage's Tale Ch. 04

by NeoShade on Oct 30, 2017
Sci-Fi & Fantasy

Yeah I know some of you are miffed I didn't make a play for a soapy hot elf chick. Yet your relieved I didn't try to diddle the halfling. I tell you now, if those kinda hang-ups get to you. Stop reading! I'm a healthy male mage in my prime, and as you will soon see, not prone to turning down pleasurable company of any kind. Long as it's of consenting age and...

Maryland My Maryland

by carvohi on Sep 14, 2017
Non-Erotic

Maryland's Heritage Introduction: This is being written in response to something an anonymous commenter included regarding my story titled "Wife Gets What She wants'. He said he had friends who all referred to Maryland as a 'Yankee State'. I wanted to address that remark. Well I am a Yankee in the 'American' sense, but I'm not precisely a Yankee, and nei...

Halloween Cross-Dressing Bash Ch. 08

by BOSTONFICTIONWRITER on Sep 16, 2017
Transsexuals & Crossdressers

She looked down and saw that he had an erection. "All you guys are the same," she said shooting him a cold stare. "Here I am pouring out my heart to you about what my ex-husband did to me and you have an erection." "Sorry." "Do you realize how humiliated I am to find out that I blew every man in my community? Then, to find out that I blew my husband's fo...