Sissy Boyfriend Stories

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Orientation
Length
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Infinite Scroll

Tunnel of Love

by Jack T. Ladd on Sep 1, 2017
Group Sex

The warmth of her body next to mine was sublime. I could not sleep. I softly stroked her silky skin as my mind constantly replayed the exquisite sexuality of what we had just shared. I knew I would not forget this night. Never. I had never dreamed of such extraordinary things happening to me. Or of how abandoned and wanton I would become. Before I was… Wel...

Someone Older and Wiser

by aznsunbeam on Sep 16, 2017
Mature

I rolled onto my stomach and looked into Jeff's blue eyes. Jeff is my boyfriend of almost a year. I know every girl says they have the best boyfriend in the world, but I really do. Let me explain: Jeff and I have been dating for almost a year and I'm still a virgin. Sure, we've done other things, but he hasn't scored that homerun yet. It's not that I don't w...

Homecoming Ch. 01

by Karenkay on Sep 16, 2017
Interracial Love

I'm David. Been up driving all night on my trip back to Michigan from where I was staying in Florida. I'll give you all the details in a nut shell. Been living and working just outside Tampa for the past three years. Got divorced from my high school sweetheart Brook three years ago after seven years of marriage. Things have been tough for me the past severa...

Helen Pt. 02

by brynhild84 on Sep 16, 2017
Interracial Love

Please do not copy this story without my written consent. For this story to make sense please read the first part: Helen Part 1. The Morning After 早上以后 'God! What have I done!!' was all that went through my head after Helen and I got back to the school. If she had just wanted to be boyfriend and girlfriend I probably wouldn't...

Like a Virgin

by DenverYo on Sep 15, 2017
Interracial Love

Sure, I had had sex before but my boyfriend of almost five years had always insisted on using a condom when we made love. He was very quick to put one on and I had hardly ever seen his bare dick. And, of course, I had never felt one in my pussy. Not one drop of cum had ever made its way into my body. So, at twenty-three years of age, I felt that I was still...

Molly, Won't You Join Us?

by johnnieblue44 on Aug 30, 2017
Group Sex

Readers often e-mail me after enjoying one of my autobiographical stories and ask, "Are your stories true?" Sure, of course they are, every word. Well, mostly. Sometimes, maybe. At least, as far as I remember things. Ah, fuck it, let's not over-analyze, just enjoy! Cheryl Morgan had, shall we say, a very healthy attitude when it came to sexual exploratio...

The Visit - A True Student Story

by BigVic77 on Sep 12, 2017
Group Sex

Shelly had gone out with a good friend of mine for over a year, and their break-up was sudden and dramatic. To cut a long story short, they were both at a student party where Shelly – brunette, sex-kitten, and always a party girl – had ended up fucking a guy she had just met. It wasn't as though she tried to be discreet about it either; one minute, she was...

Giving Nikki Away Pt. 02

by samson801 on Sep 26, 2017
Loving Wives

Part 2: The First Time Watching My Sweet Wife For several weeks after Nikki's confession, I experienced a vast range of emotions: Fear, anxiety, nausea. But mostly I experienced jealousy and arousal. Nikki and I talked on occasion, mostly by email. I often fantasized about what they were doing, but Nikki didn't go into detail about her excursions with Matt...

Jenny Cheats Ch. 03

by cicithepumpkineater on Sep 13, 2017
Erotic Couplings

Jen set down the bowl and looked at her handiwork. The table was almost full of chips, dips and general noshes for the party. Football wasn't exactly her thing but from what she understood of it, Chris's team was the underdog and in the Superbowl so they were hosting a party because they had the largest television. She heard the doorbell and bounced out...

Gina Loses Her Virginity

by Mysteria27 on Sep 25, 2017
First Time

I've been babysitting for the longest time. Every weekend, I have a job and have made enough money to buy a car. I've been babysitting for the Jackson's for about two years now. They hired me overnight and will be paying me three hundred dollars. I'm so excited to go over there tonight. The best part of babysitting over there, is their gorgeous son named Jac...