Sissy Boyfriend Stories

60,292 results
Orientation
Length
Source
Infinite Scroll

It Was Going to Happen

by dustt10 on Sep 12, 2017
Erotic Couplings

Heather and Matt headed down the aisle way towards the exit doors leading to the street; she thanked him again for helping her with this huge favor since her boyfriend Scott was at work and unable to help. She would not have been able to return that heavy chair to the store by herself. "Having such a big strong guy like yourself around sure comes in handy."...

With a Picture

by EmeraldKitten on Sep 14, 2017
Erotic Couplings

"Stupid idea." Keri stomped over to her camera and sighed disgustedly. She had the bright idea to take some sexy pictures for her boyfriend Rex for his birthday, but doing it herself was nearly impossible. Ever critical of herself, she hated something in every photo. That one, her nightie wasn't adjusted right. The next one, her face looked more awkward tha...

Second Chance

by mikoli5763 on Sep 14, 2017
Erotic Couplings

I met my second wife in the local supermarket on a Sunday afternoon when I saw a 6' tall, blonde, blue-eyed, busty, and very beautiful middle age woman walking toward me with an older man. When they passed me, I noticed in a glance neither of them were wearing rings on their left ring fingers. I decided I wanted to meet her and try to get her to go out to di...

High School Fun

by jazzyjeff98 on Sep 12, 2017
Erotic Couplings

As I sat in my 12th grade homeroom class, for what appeared to be another boring day, considering I had no homework to do as usual, it suddenly became more interesting. Crystal walked in about 10 minutes late, which was normal for her if she even showed up at all. Our teacher, Mr. Harrison, was very laid back and liberal and pretty much let us do as we pleas...

An Evening with Mr. White

by alexander930 on Sep 14, 2017
Erotic Couplings

We passed by each other in the hallway. I was on my way to a meeting and in a rush to get a seat. Frank, strolled, as he always did, down the opposite way of the corridor. "Yo,yo." He gleamed a small smile in my direction. His broad shoulders and chiseled chin betrayed any attempt he had to be subtle. I'm 5' nothing and he's 5' 10" with massive body compared...

Is That Who I Think It Is?

by dunnohowtosex on Sep 16, 2017
Exhibitionist & Voyeur

Based on a true story I love checking out those webcam sites where you can ogle hot chicks and pay them with tokens to do whatever you want. Only I never paid on principle. There were plenty of places to go for free porn and, if you waited long enough for someone else to tip, the girls usually showed their goods in the free chat. Yet, I eventually gave in...

Sophie's Summer Adventure Ch. 03

by laf199 on Sep 13, 2017
Erotic Couplings

Almost as soon as Brandon closed the door, Sophie drifted off into a peaceful sleep. The next thing she knew, it was morning. Surprisingly, she didn't have the guilt she suspected she would feel for what happened. 'It's not my fault that mother can't satisfy her man,' Sophie thought wickedly as she got out of bed and went to take a shower. As Sophie began...

A Christmas Gift from Irina & Woody

by 1mbibry on Sep 12, 2017
Group Sex

I'm Irina. My boyfriend Woody and I decided we wanted to do something special and different this Christmas. We wanted to give a unique gift that only the two of us could give together. You have to understand that Woody and I are pretty shallow individuals so rather than donating to a relief organization or a homeless shelter we decided to find one person who...

From Kendra to Kyle, with Love

by BrettJ on Sep 1, 2017
Group Sex

Author's Note: This one is a sequel to a story I wrote a few years back entitled "Kendra's Present". I hope you all enjoy this one just as much. * Kendra Christiansen had wandered the entire mall, trying to find the exact perfect present for her Kyle, her boyfriend-lover of the past 3 years. As money wasn't really an object, she'd even considered things l...

Swim Sex: A Coed Team

by mccrea on Sep 1, 2017
Group Sex

It's taken me a long time to actually bring myself to write this story… but I figured that some of you out there would enjoy it. It wasn't until just recently (within the last year) that I noticed myself discreetly checking out other guys in the locker-room, and having wild images flash through my mind. You see, I am on the Varsity Swim team at my universit...