Sissy Schoolgirl Stories

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Sissy Boy Secretary Ch. 02

by Hotenuf4u on Sep 19, 2017
Fetish

I got into the office 15 minutes early this morning, her panties cleaned and put on under my clothes, as instructed to do. The satiny lace felt good against my cock as I moved around the room. Just when the finishing details for the Scottsdale account were complete, she entered. She looked so sexy walking into the office, her ass swaying so nice. It looked l...

Further Training as Sissy Lesbian

by maturesubmale_for_F on Apr 22, 2020
Transgender & Crossdressers

Dear readers, This is a continuation of my story 'Miss Johnstone's Lesbian Sissy Slut' and I sincerely recommend reading that story first as it provides background for this one. Enjoy and please take time to give me some feedback! Theo 3. Intermission: Further training Following the loss of my sissy virginity just after I had turned eighteen years old,...

Samantha Meets a Dom Master

by SamanthaSatine on Sep 16, 2017
Transsexuals & Crossdressers

A true story - I am the main character and all the various activities described were undertaken with my consent...no harm came to me in any way... ***** The date was fixed. The room was booked – neither of the willing parties could accommodate, a not unusual event in the world these two inhabited from time to time. The morning of their meet had now arriv...

Sissy Jessica Kinky Office Shagging Ch. 02

by Sissy Adele Howells on Aug 18, 2017
Fetish

Hi again this is Sissy Jessica Howells , the kinky 0lchfa schoolgirl with an excited cock inside her navy, blue panties. At this moment my cock is inside Georgina Harris's mouth. Georgina, my 23 year old ginger girlfriend, has her head between my legs, giving me a fantastic blow job. Just feeling her long, red hair against my balls, gives me a weird sensatio...

Chronicles of Heather Maureen Ch. 09

by HeatherMaureen on Sep 16, 2017
Transsexuals & Crossdressers

Final Exam While I was waiting in bed last night for George to join me he had gathered up my clothes and purse then locked them in my car to make sure I'd spend the day with him. His clothes would fit me like a tent and his wife's merely like a pup tent so they were no help. I resigned myself to staying here and inside for the day. He made breakfast for...

Kinky Dentist Sian And Sissy Rachel Ch. 02

by Sissy Adele Howells on Dec 12, 2018
Fetish

I awoke at 5am on a cold, Saturday morning. Dreaming of my sexy dentist all night made me feel so kinky. The thought of shagging Sian Harris made my cock have a permanent erection. I was surprised to hear the bell on my front door so early. I decided to open the door wearing my pretty, pink dressing gown. It was my cousin Susan Beynon aged 37. Her flaming, r...

Miss Johnstone's Lesbian Sissy Slut

by maturesubmale_for_F on Apr 20, 2020
Transgender & Crossdressers

1. Becoming a lesbian sissy slut I was eighteen years old when I became a girl. Or rather: When I was turned into a submissive lesbian sissy slut by my High School teacher, Miss Johnstone. She was an imposing woman, in her late fifties, tall and with short cropped grey hair. She had piercing green eyes and a well-trained body that she kept in shape by regul...

A Natural Sissy Ch. 05

by harv069 on Sep 15, 2017
Transsexuals & Crossdressers

Author's note: This is a story about a woman turning a man into a compliant, sissified plaything. If that idea doesn't appeal to you, don't read the story. If you like the idea, read on, and don't forget to vote and leave a comment. More will be added if comments from readers justify it. Ch. 05 Stacy's Interlude "Hi, guys. I'm Stacy, and I guess you know...

Chronicles of Heather Maureen Ch. 08

by HeatherMaureen on Sep 14, 2017
Transsexuals & Crossdressers

Schoolgirl Nights My paranoia about being seen or recognised going home was needless worry as I made it into my place without notice. Would anyone have cared even if they had seen me? Friends or family maybe but who else, my neighbors? I smiled ruefully as the thought crossed my mind that for the first time I'd just suffered thru the 'walk of shame'! I rus...

A sissy visits the Headmistress

by maturesubmale_for_F on May 12, 2020
Transgender & Crossdressers

1. Miss Stern delivers both punishment and pleasure I knocked timidly on the heavy door and heard Miss Stern's voice from within, commanding me to enter. I slowly opened the door and walked into the presence of my Headmistress. She was in her mid-fifties and sat behind her massive oaken desk as I came in, studying a heavy file. I stood still just inside the...