Chapters tagged shy

by Syreno

Chapter 14

Tiffany and Linda arrive at the mall and they head straight for Carrie Khan. The store is busy with shoppers running back and forth grabbing whatever they see marked down. Tiffany feels dread thinking about having to enter that crowd. The last time she went shopping was with her...

by Syreno

Chapter 15

It’s Tuesday morning and Tiffany is at Linda’s place as they prepare for their beach outing with friends. Alone in Linda’s room Tiffany changes into her brand new swimsuit. She turns to the full body mirror and looks herself over. Her top fits comfortably and makes the size of he...

by Syreno

Chapter 16

The sun sits high and shines brightly. Its warm rays feel nice on Tiffany’s skin. The ocean breeze is cool and refreshing. The water is a pleasing light blue and warm gray. Everything is set for this to be a great beach day. But Tiff and Linda aren’t feeling too great right now....

by Syreno

Chapter 17

As Tiffany is about to free her throbbing cock, there is a knock on the door. “Tiff! Are you alright?” It’s Linda. “…No…” “What’s wrong? Can I help?” “Uh no! It’s nothing! I’m fine!” “…Tiff let me in.” “No! I’m fine! I’m‒I’m‒” “Let me in Tiff.” Tiff unlocks the door and L...

by Syreno

Chapter 2

Still a little nervous about actually going out in public and talking to strangers Tiffany decides that online dating would be a good start. The idea of rejection seems a lot less scary when neither party knows who the other is in real life. She can also be forward with her statu...

by Washotep

Chapter 4

While the thought of wearing a g-string out in public was mildly entertaining, Tiffany would not be caught dead wearing something so risque... She wanted to present herself as well adjusted before introducing her freakier side. Like clockwork, Tiffany hears a ping on her phone t...

by Washotep

Chapter 5

Every weekend Tiffany made time to see Lucy for the next two months. Tiffany could not wait to move out of her parent's house once she officially started her degree! The summer passed by at a snail's pace. Weekdays felt like an unnecessary intermission between Tiffany's dates wit...

by meow kitten

Chapter 4

Tiff pulls the g-string over her cock and balls, and then slides on her clothes and heads to the coffee shop. The walk there is comfortable, although her cock twitches a couple of times when the g-string rubs against her sensitive glans. The yoga teacher sits in a corner booth p...

by MegaMarshmallow

Chapter 5

Tiffany had little choice in the matter. Her objections did not even make it to her lips before she felt that deft hand hike up her sundress, push her G-string aside, and grasp her hard cock. The Yoga Teacher stroked her cock swiftly and roughly making Tiffany groan and wince. "A...

by Rabi

Chapter 3

Tiffany was surprised to immediately see someone from school that she recognized. It was John, an extremely shy and introverted boy that she occasionally made small talk with during breaks. She had always felt that they had some sort of kindred connection seeing as they were both...

by DenomZero

Chapter 3

It's the time Tiffany should make a decision, but she's not finding anyone to really send a message to. Tiff grunts frustrated at herself and keeps on scrolling until the results end and a sad emoji pops up with a text: "Refresh page". Tiff throws the phone away and collapses on...

by DenomZero

Chapter 4

Tiffany has to make a choice between revealing her penis to the internet or to maybe never get a special friend to share it with - she thinks about it and comes up with a work-around. She pulls her pants down and takes a picture of her erect cock in her panties - that is not exac...

by DenomZero

Chapter 5

Tiffany couldn't make a proper sentence as her tongue froze and throat dried. The woman was not only one of the most beautiful women Tiff had ever seen, but also the first person she has seen carrying such a massive penis. Actually, Tiff thought that she was the only one in the w...

by DenomZero

Chapter 6

Turning and getting wrapped up in the thin fabric that makes up the blanket, Tiffany rolls off the side of the bed and makes a big "THUMP" -sound as she lands on her cushioned butt. "Ouch... ah... shit..." Tiff moans and peeks up extremely sleepy, she must've slept well. Then she...

by DenomZero

Chapter 7

Tiffany was not exactly surprised but she did feel rather weird seeing the others. Much like Jack they were all boys dressed in less than boyish clothes, some looking prettier than her. "Hey..." Tiffany could muster as her eyes were pinned on what was going on at the other side o...

by DenomZero

Chapter 13

The hallway is one of those really tall Victorian era ones found in fancy palaces and whatnot. It has a few doorways. The one to the Velvet room, one at the end leading to the ballroom and one at the back leading to the bedrooms as well as a door leading to the dressing room. “He...