Sissy Teen Stories

16,707 results
Orientation
Length
Source
Infinite Scroll

College is a Time to Explore Ch. 01

by ddogg44 on Sep 15, 2017
First Time

I didn't know what I was thinking. My hands were still shaking from the excitement. My heart raced as I finished verifying my craigslist account. My online ad, which garnished a picture of my plump bottom being spread wide to reveal my sweet hairless hole was titled "Teen ISO Daddy". I stated that I still had my anal cherry, in fact I had never even been wit...

Caught in Panties Ch. 01

by pantyperv on Sep 25, 2017
Fetish

I have a beautiful wife who I adore more than anything in this world. We’ve been married for about four years, but she is the only woman I have been with for the past ten years. She is six years my junior and I waited until I was in my thirties before I finally asked her to marry me. She is 5’8”, blonde hair, blue eyes, and has a smoking body. I catch other...

Being My Roommate's Sissy Pt. 02

by SubTessa on Sep 19, 2017
Transsexuals & Crossdressers

Waking up this morning was just a mix of feelings - shame, pleasure, defeat, embarrassment. Tanner's display of 'power' over me was three days ago, and in that time - according to his brags and occasional light-hearted messages he likes to show me - he has convinced Kara to come over to 'hangout' tonight. My mind was so confused, I told myself I would stand...

Bitch Maker Ch. 03

by YANKEE DAN on Sep 12, 2017
Transsexuals & Crossdressers

Author's Note: A lot of people have requested that I continue this series, and finally I have gotten around to it. Enjoy! * "Alex bring me some juice." Sammie said, rolling over in bed and hugging her pillow. "Yes mistress!" I replied, with enthusiasm. I crawled out of bed and walked down the hall, on the way past Tim's room I looked in on him. He lay t...

Becoming a Sissy Maid & Slut Vol. 10

by Sissy_Chantel on Sep 19, 2017
Transsexuals & Crossdressers

Chapter Seventeen: It's time that Chantel Earned Her Keep. Well it's the morning of a Saturday, to where by night time I will soon be doing some true sissy slut street walking and now truly begin to earn my keep and begin to earn some serious money for my Master. I awake like all other mornings at 7:30am and follow my morning routine, enema, shower, shave...

Sissy for a Day

by silkstockingslover on Oct 16, 2018
Fetish

Summary: With his wife's help and support, a man becomes a sissy for black cock. Note 1: This is a Halloween 2018 Contest Story. Be warned: this story involves sissy sex, obsession over black cock and a bukkake. If this isn't your thing, please don't read any further. Note 2: This is dedicated to the real Paul who requested this story. Note 3: Thanks to:...

Marcia Goes Back to School

by Belongs2Beth on Sep 12, 2017
Transsexuals & Crossdressers

Authors Note: This story continues the adventures of eighteen year old Marcia (nee Marcus) Cicero. The tale opens a week after the events related in "Carol's Gifts". Marcia has shown visible signs of blossoming in the wake of Mistress Carol's injection of powerful hormones and is anticipating returning to her school for the first time as a girl. To answer an...

Feminized by My Girlfriend Ch. 02

by Trinni69 on Sep 25, 2017
Transsexuals & Crossdressers

I followed Brook and Linda out of the spa onto the sidewalk and I looked around for the limo but it was no where to be found. As the girls started walking down the street and talking to each other, I asked where the limo was. Neither of them responded and just kept walking. I followed behind as closely as I could and hoped no one would notice me. Luckily it...

Truth or Dare Ch. 03: Take Me Tom

by RebeccaCherie on Sep 16, 2017
Transsexuals & Crossdressers

Cupping his balls in my left hand I move position to take my man in my mouth. My Mother always told my older sister that it is a woman's role, her duty to please her man, to be there for him as needed, when needed. I wonder if my sister is as compliant, as obliging with her Husband of 6 months as I wish to be for Tom. I could be a very obliging young lady in...

Neighbors Sissy Son

by newfield1981 on Sep 18, 2017
Transsexuals & Crossdressers

About two months ago a woman and her son moved into the vacant apartment next to mine. I noticed right away how effeminate the son was, even though he was dressed like any other 18yr old boy, he couldn't have weighed more than 115lbs and his facial features were soft and delicate! Having a thing for femboys (twinks) I set my sights on this one! Since I wor...