sexstories.com
Transgendered
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Becoming Charlotte - Part 15: Oh! We're going to Ibiza! by bigdaddyoh
«Charlotte goes to Ibiza with her work friends, having a holiday romance and discovering a troubling secret about the guy she's with, then life takes an interesting, if slightly disturbing turn.»
Rated 81.1%, Read 1329 times, Posted Mon 3rd of August 2026
Fantasy , Blowjob, Consensual Sex, Exhibitionism, Male/Female, Masturbation, Toys, Transgendered -
How did things end up like this? : Prologue by HannahBigBanana
«Blake, a somewhat shy, unaccomplished guy, gets paired with the hottest girl at school for a group project. As they begin growing closer, he becomes more optimistic of the future. His twin sister Rachael may throw a wrench in his plans.»
Rated 86.4%, Read 4038 times, Posted Mon 20th of July 2026
Fiction , Cuckold, Extreme, Female Domination, Transgendered -
Trading Places With My Cousin - Part 1 by justaguy999
«I've never believed in magic or the supernatural, but a visit to see my uncle and cousin in Louisiana changed all of that.»
Rated 91.7%, Read 119202 times, Posted Sun 31st of May 2026
Fantasy , Blowjob, Oral Sex, Teen, Transgendered -
Becoming Charlotte: Part 14 - A wedding and an asshole by bigdaddyoh
«Shortly after returning from Amsterdam, Sally calls Charlotte with some amazing news, she's getting married. Everything goes swimmingly until it's nearly ruined by the best man»
Rated 85.8%, Read 8925 times, Posted Fri 10th of July 2026
Fantasy , Authoritarian, Blowjob, Bondage and restriction, Transgendered -
Doll House - Aspen, Scott (pt 8) - The Switch by Wanderwolf
«Slick was in charge until he was not.»
Rated 62.5%, Read 1641 times, Posted Sat 4th of July 2026
Fantasy , Ass to mouth, Blowjob, Bondage and restriction, Cheating, Cock & ball torture, Consensual Sex, Female Domination, Hardcore, Male Domination, Masturbation, Mind Control, Oral Sex, Toys, Transgendered -
Doll House - Detective Nolms story by Wanderwolf
«Mother teachers the good detective that he is only a toy for her to order about.»
Rated 71.4%, Read 2124 times, Posted Sat 4th of July 2026
Fantasy , Anal, Ass to mouth, Bi-sexual, Blackmail, Bondage and restriction, Cheating, Cock & ball torture, Coercion, Cum Swallowing, Female Domination, First Time, Gothic, Hardcore, Humiliation, Latina, Oral Sex, Reluctance, Transgendered -
Wartime Comfort House Diary - Day 10 Birthday Celebration by rojac29
«Comfort House Administrator Miss Yamaha organized my personal comfort team to hold a very unique Birthday Party for me.»
Rated 87.5%, Read 12504 times, Posted Fri 12th of June 2026
Fiction , Anal, Asian, Authoritarian, Bi-sexual, Blowjob, Cum Swallowing, Domination/submission, Foot or shoe fetish, Hardcore, Interracial, Lactation, Male / Females, massage, Oral Sex, Threesome, Transgendered, Transsexual -
Becoming Charlotte - Part 13: Sexual Reawakening, an Amsterdam Story by bigdaddyoh
«Charlotte and the girls explore Amsterdam and two sexual encounters help her to finally move on»
Rated 86%, Read 9822 times, Posted Mon 29th of June 2026
Fantasy , Blowjob, Consensual Sex, Cum Swallowing, Exhibitionism, Group Sex, Lesbian, Transgendered -
Becoming Charlotte - Part 12: The next 18 months. by bigdaddyoh
«Charlotte recovers from losing Andy and finds a job to help relieve her move on with her life. Her behaviour on certain nights out make her question a rule she set for herself shortly after her transformation. This chapter is mostly non-erotic with only brief de***********ions of sexual acts.»
Rated 86.4%, Read 4446 times, Posted Sun 21st of June 2026
Fantasy , Non-Erotic, Transgendered -
Becoming Charlotte - Part 11: Pleasure is always followed by pain by bigdaddyoh
«Charlotte and Andy enjoy their holiday, Andy bonds with Mae, Charlotte shows andy a special toy and then the unthinkable happens.»
Rated 86.3%, Read 5520 times, Posted Tue 16th of June 2026
Fantasy , Anal, Consensual Sex, Exhibitionism, Toys, Transgendered -
Becoming Charlotte - Part 10: The first week of Andy’s leave by bigdaddyoh
«Charlotte and Andy spend time with various friends, even learning something new about some of her oldest friends and Andy has a surprise for her.»
Rated 85.7%, Read 3324 times, Posted Mon 1st of June 2026
Fantasy , Consensual Sex, Exhibitionism, Group Sex, Transgendered -
Becoming Charlotte - Part 9: Role play and Experimentation by bigdaddyoh
«Charlotte fulfils Andy’s request and his welcome home party leads to a new experience with two of their best friends»
Rated 86.5%, Read 2994 times, Posted Sat 23rd of May 2026
Fiction , Anal, Cosplay, Group Sex, Role-playing, Transgendered -
Clementina, Chapter 5 – Citadel & Interlude [re-post] by JackDRipper
«The ancients and the spirits have many dirty little secrets, and they do not yield them easily...»
Rated 58.3%, Read 2181 times, Posted Fri 22nd of May 2026
Diary , Extreme, Monster, Transgendered -
Becoming Charlotte - Part 8: A very interesting day by bigdaddyoh
«Charlotte and Andy enjoy the first day of their reunion.»
Rated 85.7%, Read 2607 times, Posted Tue 19th of May 2026
Fiction , Exhibitionism, Transgendered -
Becoming Charlotte: Part 7 - Making new old friends by bigdaddyoh
«As Leon’s funeral looms, Charlotte prepares to regain old friends and a surprise reunion occurs.»
Rated 85.7%, Read 2649 times, Posted Thu 7th of May 2026
Fantasy , Consensual Sex, Toys, Transgendered -
The twins by FantasiasTrans
«Two identical twins seduce, dominate and prostitute the boyfriend of one of them»
Rated 53.3%, Read 5937 times, Posted Fri 20th of March 2026
Fiction , Female Domination, Humiliation, Prostitution, Transgendered -
Daddy's Dilemma..Part1 by C.dotsa
«A dad and his daughter explore her cock»
Rated 83.9%, Read 22182 times, Posted Sat 21st of March 2026
Fantasy , Blowjob, Cheating, Oral Sex, Teen, Transgendered, Transsexual, Transvestite -
I learned my mother is trans by Jim2066
«I came home for spring break and learned my mother is trans.»
Rated 85%, Read 12666 times, Posted Fri 20th of March 2026
True Story , Bi-sexual, Cum Swallowing, Transgendered -
Daddy's Dilemma by C.dotsa
«A dad and his daughter explore her cock.»
Rated 78%, Read 12558 times, Posted Sun 22nd of March 2026
Fantasy , Blowjob, Oral Sex, Transgendered, Transsexual, Transvestite -
The Loop - part 25 by Wanderwolf
«Alex is taken in for an interview at S.L.U.T. Corp»
Rated 70%, Read 2790 times, Posted Mon 23rd of February 2026
Fantasy , Anal, Ass to mouth, Authoritarian, Blowjob, Domination/submission, Hardcore, Humiliation, Job/Place-of-work, Oral Sex, Transgendered -
She-Hulk SMASHED by AnalLover42069
«She-Hulk pays stripper Rikki Ryder with intense anal sex for vital client information.»
Rated 62.5%, Read 4113 times, Posted Mon 5th of January 2026
Fiction , Anal, Consensual Sex, Fan fiction, Female Domination, Oral Sex, Transgendered, Transvestite -
The Opposite Gender by SailorVibe
«Female about to undergo sex reassignment surgery let's me enjoy her micro-penis and lets me fuck her pussy.»
Rated 75.4%, Read 9057 times, Posted Fri 14th of November 2025
Fantasy , Bi-sexual, Body modification, Consensual Sex, Male/Female, Older Male / Female, Oral Sex, Transgendered, Transsexual, Transvestite -
Bambi by SailorVibe
«I meet a hot chick at the bar. Take her home. She turns out to be a he!»
Rated 82.2%, Read 18135 times, Posted Sun 19th of October 2025
Fantasy , Anal, Ass to mouth, Blowjob, Body modification, Cum Swallowing, Oral Sex, Transgendered, Transsexual -
Rocky Revisited - A Halloween Story by The_Technician
«A 50th anniversary Rocky Halloween Party.»
Rated 82.1%, Read 5958 times, Posted Wed 15th of October 2025
Fantasy , Alien, Anal, Blowjob, Cosplay, Erotica, Exhibitionism, Female/Female, Group Sex, Male / Females, Transgendered, Transsexual -
Babalon's Curse 8 by M_K_Babalon
«A woman who worships the Goddess Babalon helps her with a new curse to turn men into werewhores.»
Rated 66.7%, Read 5421 times, Posted Mon 25th of August 2025
Fantasy , Consensual Sex, Oral Sex, Transgendered -
Saturday night trans fever by Foryourpleasure1980
«This is the story of my one and only encounter with a transgender girl»
Rated 83.1%, Read 14466 times, Posted Tue 19th of August 2025
True Story , Anal, Bi-sexual, First Time, Masturbation, Oral Sex, Transgendered -
The Corruption of a Straight Boy, part 1 by alopex69
«Tom and Jen have been trying new things, Tom didn't expect a third person would get involved.»
Rated 94.4%, Read 69207 times, Posted Sun 6th of July 2025
Fantasy , Anal, Bondage and restriction, Drug, Male/Female, Pegging, Transgendered -
The Corruption of a Straight Boy, part 2 by alopex69
«Tommy gets more than he bargained for when he goes to a bar with Lexi and Jen.»
Rated 95.6%, Read 31941 times, Posted Tue 8th of July 2025
Fantasy , Anal, Cum Swallowing, Drug, Male / Females, Transgendered -
The Corruption of a Straight Boy, part 3 by alopex69
«Lexi and Jen leave Tommy stranded at a glory hole. Then they arrange for him to get another gangbang.»
Rated 95.6%, Read 32472 times, Posted Tue 8th of July 2025
Fantasy , Anal, Cum Swallowing, Drug, Male / Females, Transgendered -
Hard Evidence by AnalLover42069
«Femboy stripper Rikki Ryder gets interrogated by Officer Maxine Steele, who fucks her in the ass.»
Rated 86.8%, Read 9030 times, Posted Fri 20th of June 2025
Fiction , Anal, Blowjob, Consensual Sex, Job/Place-of-work, Transgendered, Transsexual, Transvestite -
The Boy in the Cream Blouse by satinshirt
«A Soft Fiction of Friendship, Light, and Becoming...»
Rated 72%, Read 5976 times, Posted Tue 24th of June 2025
Fantasy , Transgendered, Transvestite -
Becoming Charlotte - Part 6: Coping and Preparing by bigdaddyoh
«Charlotte deals with missing Andy, using imagination and toys to cope with her desires with surprising results and finally steps into her new life outside the institute.»
Rated 85.7%, Read 5442 times, Posted Wed 28th of May 2025
Fantasy , Female solo, Hardcore, Masturbation, Toys, Transgendered -
Becoming Charlotte - Part 4: Making the most of it 1 of 2 by bigdaddyoh
«As Charlotte and Andy come to terms with him leaving for basic training, they discover a secret and decide to do a little matchmaking.»
Rated 85.7%, Read 5319 times, Posted Thu 15th of May 2025
Fantasy , Blowjob, Consensual Sex, Hardcore, Oral Sex, Transgendered -
Becoming Charlotte - Part 5: Making the most of it 2 of 2 by bigdaddyoh
«Charlotte and Andy put their matchmaking plan into action and Charlotte gives him a special going away present.»
Rated 85.7%, Read 5235 times, Posted Thu 15th of May 2025
Fantasy , Anal, Consensual Sex, Hardcore, Oral Sex, Transgendered, Virginity -
Becoming Charlotte - Part 3: Love, love, love (doo doo de doo) by bigdaddyoh
«Charlotte deals with being in love as a woman, rumours and Inquisitions from friends as she and Andrew start the relationship together»
Rated 85.7%, Read 5220 times, Posted Sat 3rd of May 2025
Fantasy , Blowjob, Consensual Sex, Male/Female, Oral Sex, Transgendered -
More than before.. part 1 by C.dotsa
«A boyfriend... accepts his girlfriends cock.»
Rated 89.3%, Read 29979 times, Posted Sat 3rd of May 2025
Fantasy , Blowjob, Cum Swallowing, Humiliation, Transgendered, Transsexual, Transvestite -
Becoming Charlotte, Chapter 2: Death and Rebirth by bigdaddyoh
«Charlotte, a 25yo redhead biological female who used to be a biological male comes to terms with being raped and has to face her former self, all whilst preparing to start her new life in the outside world.»
Rated 87.5%, Read 6036 times, Posted Sun 27th of April 2025
Fantasy , Consensual Sex, Death, Masturbation, Transgendered -
The Principal's Turn - Sam's Fall by rimaday
«With Principal's Turner's seduction complete, Taisha finds a way to Deal with her husband Sam»
Rated 94.2%, Read 20175 times, Posted Sun 30th of March 2025
Fantasy , Ass to mouth, Black, Blowjob, Cum Swallowing, Domination/submission, Gay, Reluctance, Transgendered -
TRANNY AT THE SWINGERS RESORT by CecilBCK
«My man and I are seeking new sexual experiences at a swingers resort.»
Rated 79.3%, Read 15750 times, Posted Tue 24th of October 2023
True Story , Ass to mouth, Bi-sexual, Blowjob, Body modification, Consensual Sex, Erotica, Exhibitionism, Female exhibitionist, Hardcore, Oral Sex, Transgendered, Written by women -
One Night With Stacy by JJStories
«Stacy was my best friend. I trusted her. Look what she did.»
Rated 87.4%, Read 20610 times, Posted Wed 20th of November 2024
Fiction , First Time, Lesbian, Pregnant, Transgendered, Transsexual -
ANOTHER COCKTAIL PARTY by CecilBCK
«Another cocktail party for another new product launch, this time for a range of adult toys and accessories. This one much more entertaining than many others. My lady Sarah and I do enjoy them though and treat them as an opportunity to meet new sexual partners.»
Rated 73.1%, Read 17844 times, Posted Sat 12th of August 2023
True Story , Ass to mouth, Bi-sexual, Blowjob, Body modification, Boy / Boy, Consensual Sex, Cosplay, Cuckold, Erotica, Exhibitionism, Extreme, Female exhibitionist, First Time, Gay, Group Sex, Hardcore, Male / Older Female, Males / Female, Older Female / Males, Oral Sex, Role-playing, Threesome, Transgendered, Voyeurism -
Travels Through The Multi-Sheverse by AnalLover42069
«An anthology series about different erotic worlds about a crossdresser stripper named “Rïkkï Rÿdër” who gets her ass fucked by different girls with all kinds of girl-cocks»
Rated 50%, Read 21549 times, Posted Sun 20th of October 2024
Fantasy , Alien, Anal, Female Domination, Monster, Pegging, Transgendered, Transsexual, Transvestite -
Morgan Switches Teams by BigDaddyDG
«The back story of how Morgan became a she.»
Rated 77.8%, Read 9681 times, Posted Tue 15th of October 2024
Fiction , Transgendered -
My Evolving Transition – Ch. 08 by Luvagobfull
«The ongoing adventure of a young man, transitioning into a new adventure.»
Rated 50%, Read 69885 times, Posted Fri 28th of June 2024
Fiction , Anal, Consensual Sex, Transgendered -
One night to suck a dick by robdcruz
«A man's attempts to explore his sexuality take an unexpected turn»
Rated 94.8%, Read 113382 times, Posted Wed 5th of June 2024
Fiction , Gay, Transgendered -
Anniversary Surprise - Part 1 of 2 by storiesforyou
«A neglected wife sends a surprise to her husband's hotel room since he's out of town for their anniversary»
Rated 88.4%, Read 15831 times, Posted Mon 13th of May 2024
Fiction , Blackmail, Blowjob, Cheating, Cum Swallowing, Female Domination, Male / Females, Oral Sex, Transgendered, Transsexual -
Babalon's Curse 3&4 by M_K_Babalon
«The curse is laid and the suffering begins.»
Rated 73.9%, Read 7173 times, Posted Sat 27th of April 2024
Fantasy , Anal, Coercion, Oral Sex, Reluctance, Transgendered -
Sexy BFFs Chapter 13 by Jenny Lane
«Jenny and Gracie are the only students left at the boarding school for the summer and they make a new sexy friend.»
Rated 59.1%, Read 4821 times, Posted Wed 17th of April 2024
Fiction , Transgendered -
Sexy Bff's Chapter 12 by Jenny Lane
«A flashback story to when Jenny and Gracie meet at boarding school and get into some wet, messy and muddy fun!»
Rated 55%, Read 5289 times, Posted Mon 1st of April 2024
Fantasy , Anal, Blowjob, Cum Swallowing, Interracial, School, Transgendered -
Tinder Tranny Hook Up by markerss
«This story took place many years ago after breaking up with a girlfriend of several years. I was feeling lost and felt I need to get out there. I started looking at porn online, and eventually searched the internet for dating site, and even casual sexual encounter sites.»
Rated 89.8%, Read 34410 times, Posted Mon 5th of February 2024
True Story , Anal, Blowjob, Consensual Sex, First Time, Mature, Teen, Transgendered, Transsexual, Transvestite, Young -
Taking over as massage therapist for two weeks - Part 2 by SensuousTurquoise
«I have my second massage appointment, this time with a beautiful, young trans woman. The massage turns even more sexual than last time.»
Rated 83.7%, Read 81309 times, Posted Tue 6th of February 2024
Diary , Bi-sexual, Blowjob, Consensual Sex, Female / Girl, First Time, massage, Masturbation, Transgendered, Written by women -
Christmas Eve with Gloryhole Glenda by Limnophile
«Man pays for anonymous blowjobs and gets several big surprises. CAUTION - If you hate smoking or trans / bi males please read something else.»
Rated 75.7%, Read 22590 times, Posted Fri 27th of October 2023
Fiction , Blowjob, Male/Teen Female, Prostitution, Romance, Transgendered -
2 she males 1 lucky male by Martyn1981
«2 she males 1 lucky male all alone»
Rated 82.6%, Read 23265 times, Posted Fri 3rd of November 2023
Fiction , Anal, Transgendered, Transsexual, Transvestite -
The Body Whisperer by fidgetwrites
«Amanda discovers a spiritual healer who can help her attain the extreme proportions her body was always supposed to have.»
Rated 80%, Read 9444 times, Posted Fri 6th of October 2023
Fiction , Body modification, Exhibitionism, Female/Female, Mind Control, Plumper, Transgendered -
Neighbors Part One by TheGentlemn4yu
«New neighbor surprise»
Rated 83.1%, Read 21573 times, Posted Fri 15th of September 2023
Fiction , Bi-sexual, Blowjob, Cum Swallowing, Oral Sex, Transgendered -
Privileges Revoked - Chapter 1 by ArielZark
«A young man goes in for an interview and receives a generous job offer. But can he satisfy his boss's demands?»
Rated 85%, Read 22158 times, Posted Tue 5th of September 2023
Fiction , Coercion, Female Domination, Humiliation, Job/Place-of-work, Male/Female, Reluctance, Slavery, Transgendered, Transsexual -
Sex at the theater by Jim2066
«Had lots of great sex at an adult theater, with a surprise»
Rated 90.7%, Read 40446 times, Posted Thu 7th of September 2023
True Story , Bi-sexual, Blowjob, Cum Swallowing, Exhibitionism, Group Sex, Oral Sex, Transgendered -
Cheat Day by BashfulScribe
«What starts out as a movie night turns into a night where Ethan discovers a lot more about himself.»
Rated 89%, Read 33153 times, Posted Wed 9th of August 2023
Fiction , Blowjob, Boy / Boy, Consensual Sex, Erotica, Exhibitionism, First Time, Gay, Group Sex, Male/Female, Oral Sex, Romance, Transgendered -
Wee Jock's last night stand before he transitions and loses his balls by abroadsword
«Wee Jock sees an opportunity to play major league Soccer for the girls team if he transitions to a trans woman»
Rated 52.3%, Read 7059 times, Posted Fri 21st of July 2023
Fiction , Body modification, Lesbian, Male / Females, Transgendered -
Michael to Michelle part 4 the work slut by SonicRush66
«As I go further and further into the sissy life, my workplace finds out»
Rated 91.4%, Read 21438 times, Posted Tue 18th of April 2023
Fantasy , Anal, Bi-sexual, Blackmail, Blowjob, Cum Swallowing, Domination/submission, Gay, Job/Place-of-work, Male Domination, Reluctance, Threesome, Transgendered, Transsexual, Transvestite -
Roberta Slut by Yankee Dan
«This is the story of how a virgin trans girl started to blossom and have come out, with the help of her slut mother and best friend.»
Rated 93.6%, Read 35748 times, Posted Sat 4th of March 2023
Fiction , Anal, Blowjob, Gay, Teen Male / Teen Male, Transgendered, Transsexual -
Cross dressing gay fantasy act 2 by Martyn1981
«Time to try something new»
Rated 73.6%, Read 14532 times, Posted Tue 28th of February 2023
Fiction , Anal, Boy / Boy, Consensual Sex, Gay, Transgendered -
Asian Massage Parlor by markerss
«I had just gotten back from a business trip and feeling i needed an adjustment, I reached out to my chiropractor to no a vale. However, i search for local massage parlors and ended u0 deciding on 9ne that was listed as an Asian massage place.»
Rated 89.7%, Read 62265 times, Posted Sun 19th of February 2023
True Story , Anal, Asian, Blowjob, Gay, massage, Reluctance, Transgendered, Transsexual, Virginity -
Cross dressing gay fantasy by Martyn1981
«I've often fantasized about being fucked with a strap on before realising that a real cock would feel so much nicer than a strap on. here is my fantasy -»
Rated 70.2%, Read 16659 times, Posted Thu 19th of January 2023
Fiction , Anal, Gay, Hardcore, Role-playing, Transgendered, Transsexual -
First time reverse Crab by Martyn1981
«Me and my bit on the side Dave try Reverse Crab for the first time xx»
Rated 84.5%, Read 12732 times, Posted Sat 21st of January 2023
Fiction , Anal, Boy / Boy, Consensual Sex, First Time, Gay, Transgendered, Transsexual -
KINKY ANNABELLE. by CecilBCK
«Ada has new assignment for me which might be a bit kinky.»
Rated 83%, Read 13716 times, Posted Mon 16th of January 2023
True Story , Authoritarian, Bi-sexual, Blowjob, Cheating, Cosplay, Cuckold, Cum Swallowing, Erotica, Exhibitionism, Gay, Group Sex, Hardcore, Male/Female, Oral Sex, Threesome, Transgendered, Voyeurism -
FTM Sexy Antics by TransManZest
«We are a horny couple and need sexual satisfaction as often as possible. I am never happier than when my large clit is being sucked and my sexy wife knows exactly how to pleasure me.»
Rated 80%, Read 9843 times, Posted Fri 6th of January 2023
True Story , BDSM, Domination/submission, Toys, Transgendered, Wife -
The Day My Best Friends Dad Made Me A Woman by BreePhillips
«It all started as what it would take to become a woman. A change I knew I needed in my life.»
Rated 89.9%, Read 58797 times, Posted Fri 9th of December 2022
True Story , Anal, Gay, Reluctance, Transgendered, Young -
Michael to Michelle 2- Glory hole revelation by SonicRush66
«After his experience at the sex shop, Michael starts the journey to femanize himself and have new sexual experiences»
Rated 93%, Read 36375 times, Posted Wed 30th of November 2022
Fantasy , Anal, Bi-sexual, Blowjob, Boy / Boy, Cheating, Cum Swallowing, Gay, Group Sex, Threesome, Transgendered, Transsexual, Transvestite -
Sexy BFF's Chapter 11 by Jenny Lane
«Five sissy sluts sex fest in the forest.»
Rated 48.1%, Read 6225 times, Posted Sat 3rd of December 2022
Fiction , Anal, Cum Swallowing, Group Sex, Transgendered