Chapter 3

Jess and Anthony had another dare ahead of them. This one was unusual, they both had to undergo the dare together, but the details would vary. They both had to wear a chastity device for the whole week, starting on Monday, through to Sunday.

Starting off the week, they were both working from home. They had been locked up, and were ready to face the week. Anthony had Jess sitting with no underwear on, and a skirt, and every half an hour she had to run a feather up the inside of her thighs. By mid-morning her nipples were hard all the time, and she was having trouble concentrating. She sent Anthony a picture of this, so he replied saying now she had to play with her nipples every time she used the feather. Jess could feel her arousal growing all day.

In contrast, Anthony didn’t seem to suffer too much during the day. Jess had told him to stroke his thighs with his hands, but he was coping okay. In the spirit of fair play, Jess told Anthony he had to dress in his best female clothes under light trousers, and meet her at the store.

“We are going to walk around the store now, and whenever it looks like we are alone I’m going to slide down the front or back of your trousers and give it a little play” said Jess.

Anthony was forced to walk around slowly, and the first time it looked like they were alone, Jess stood in front of him and pulled down the front of his trousers, exposing the pink underwear, and started to massage his balls. Anthony moaned, and strained against the cage, but he couldn’t get hard. Jess let him go and walked on. The next time they seemed alone Jess stood at Anthony’s hip and pulled the back of his trousers down. If anyone was behind them in the aisle they would now see the pink thong, and Jess took a small butt plug from her purse, looked Anthony in the eye, and said “Suck”.

Anthony couldn’t do it, he looked back at Jess saying “Please, no. This is too public”. Jess simply replied by turning him through 45 degrees, so now he was facing the length of the aisle. Down the far end a couple were just starting to browse the shelves. “If you don’t suck this now, I’m going to turn you around and put this in dry” said Jess, in a louder voice. Anthony immediately complied, knowing that was so much worse. As Jess ran the plug over his tongue he just prayed the couple turned around. Once the plug was nice and wet, Jess took it out and held it behind Anthony’s back. She reached up, licked his ear, and said “I suggest you squat down and look at that bottom shelf quickly, we have company coming”.

Anthony turned to his left, squatted as Jess stepped to the right, putting herself between him and the couple. Jess reached down, and started to slide the plug into him, before pausing, and sliding it out again. She kept thrusting into him, holding him caught against the shelf, as the couple walked behind them. They both heard the guy say to his girl friend “That sissy takes it almost as well as you honey” as they walked on. Jess could feel her juices flowing over her belt, down her thighs under the skirt, and Anthony felt his heart almost stop, it was trying so hard to make his cock bust out of it’s cage.

The couple turned the corner, and Jess said to Anthony “Before you get up, clean that mess you’ve made with your tongue.” Jess stood, as Anthony ran his tongue up the inside of her thighs, tasting all her juices.

Neither of then could think of shopping anymore, and they quickly left the store. As they got to the car, Anthony had Jess sit, with her legs up on the dash, and took a vibrator from the console. He started to run it up and down her thighs, and leaned over and pulled her top down to suck on her nipples. He made sure to run the vibrator all the way up to her knees so it was visible each time.

“There is no way we are going to last a week if this is just the first day” they agreed, looking at each other, panting with need that would go unfulfilled.