Sissy Lauren

Pandemic Truth or Dare, Part 2 - Settling In

Jonah was wearing a pink tank top and black miniskirt as he cooked dinner for him and Kelly. The pandemic still raged on, and the couple continued to do their dares from the Truth or Dare game a few weeks back. It took a while for Jonah to get used to his new wardrobe, especially the bras, but he was feeling more comfortable in it with every day that passed.

Pandemic Truth or Dare, Part 1 - A New Game

Due to the global pandemic, everyone is forced to stay at home until things have died down. This was great news for Jonah and Kelly, because their jobs continued to pay them, even though they can’t work from home. The couple decided to spend more time together, and they were loving it.

Dare Poker - Part 4: The Fight for Freedom

Miles had to be up early again to get ready for classes. He showered as normal and got dressed, again putting on one of the pairs of panties. He went downstairs to get breakfast and talked a little with the girls, who were of course ready at this time of day. After he had finished eating, he headed off to class.

Bro to Sis in Minutes

Hailey was tired of her twin brother. Howard was always that one brother who you couldn’t seem to bond with. He’s a great guy, but he always kept to himself, and Hailey rarely got to spend time with him. She’d try to take him out with some friends, or even just watch a movie with him, but to no avail. She had always wanted a sister, someone else to have by her side, but their parents stopped with just the two of them.

New Nails

I can’t believe that I was doing this. I had (stupidly) competed with my girlfriend, Carrie, over the Oscars. Initially starting as playful fun, we made a bet with each other that, whoever had the most correct Oscar winners, got to choose something for the loser to do as “punishment”. After careful decision-making, I had decided that, if I won, then Carrie would have to mow the lawn in her bikini, once a week, for the entire summer. Having heard my choice, Carrie made hers similar to mine.

A Bet Gone with the Man

Allen and Jodie both stepped foot into the Transformation Salon. They went up to the reception desk and checked themselves in. They had an appointment, but they were a little early, so they went into the waiting area and sat down. While they waited, Jodie scrolled on her phone, casually talking about what they might do later. But Allen wasn’t really paying attention to what she was saying. No, he was thinking about how he got here. How any of this was even happening to him. He reflected back on how it all started…

Dare Poker - Part 3: Primed and Polished

Liz whispered something to Felicia, then said aloud, “Felicia is the one who will do your nails. She has the biggest nail polish collection out of all of us, which is why I figured that it was best for her to do it. She knows the colors I picked out, so you can go with her to her room to get started.” Miles did as told and walked with Felicia to her room.

Dare Poker - Part 2: The Panty Trap

“This can’t be happening,” Miles thought. “I have to wear women’s underwear for a whole week? There’s no way this is real life.”

Liz had Miles follow her upstairs and led him into her room. She went into her closet to search for something, and as she did, Miles looked around the room. It was practically the same as his, except she had a frilly pink bed and a big mirror on top of her desk, which had an array of makeup in front of it. After looking through her closet for a little while, Liz popped out with an unopened pack of panties.

Dare Poker - Part 1: Moving In

Miles lugged his suitcase through the streets as he headed towards his new residence. He didn’t pack much, but having to walk a mile carrying his luggage was excruciating. If only he had his car, except it was unable to start and is in need of maintenance. The bus had to do for now, where the closest stop was off-campus and very inconvenient.

Summer Explorations 3: Locked Up

I left off the story with me exploring my femininity with my girlfriend, Anna. We had gone to the mall, and Anna had bought a little something special for me…

Day 7

As I woke up, I noticed that Anna was lying awake in my arms. I kissed her and told her good morning, and she did the same. The combination of her closeness and the feeling of my new nightgown was exhilarating. This was definitely the life.

Summer Explorations 2: An Accepting Girlfriend

Last summer was the best experience I had ever had, but it had to end some time. Mom and Jenny surprisingly didn’t catch on to anything that had happened, at least nothing that they mentioned to me. I had decided to go to a college that was close to home, but I wanted to live in the dorms as it was more convenient for me. It was definitely hard being fully on my own, but I was able to get through it.

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