Sissy Lauren

From Straight to Sissy

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During a game of “Truth or Dare”, my friends dared me to dress up in my girlfriend’s clothes and ride her dildo. Now, you would think that this would be a little too extreme, but not for our friend group. Every game we played had something that most people would never do, especially with their friends. Anyways, since I wasn’t a coward, I accepted the dare.



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This story is 68 words long.

Brothers Think Alike 1 - Becoming Sissy Sisters

The Friedlander family was not your average family. Consisting of a mom and dad, twin daughters (Samantha and Sandra), and twin sons (Brian and Blake), they lived a somewhat-lavish lifestyle. Both parents were trust fund babies, but the children rarely ever saw that wealth, so they never felt like they were rich.



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This story is 52 words long.

Discovery of a Sissy

After a man’s wife leaves him, he falls down the path of sissyhood.



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This story is 14 words long.

Pandemic Truth or Dare, Part 3 - Changing Hands (and Feet)

Another week had passed, and Jonah and Kelly were still playing their little game as the pandemic continued. Jonah was wearing a cute red sundress that day, while Kelly wore some cargo shorts and a flannel shirt. Jonah’s body was still hairless from the waxing, and Kelly made sure that he lotioned himself everyday to keep his skin soft.



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This story is 60 words long.

Fantasy Becomes Reality

A man goes through a transformation after his wife discovers a fantasy of his.



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This story is 14 words long.

Pandemic Truth or Dare, Part 2 - Settling In

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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.



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This story is 70 words long.

Pandemic Truth or Dare, Part 1 - A New Game

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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.



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This story is 53 words long.

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.



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This story is 61 words long.

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.



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This story is 86 words long.

New Nails

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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.



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This story is 89 words long.

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…



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This story is 95 words long.

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.



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This story is 73 words long.

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.



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This story is 107 words long.

Dare Poker

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A boy decides to share a house with four girls while they all are going to college. They play a game called “Dare Poker” every Friday night, but how extreme will things get when the dares start rolling out?



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This story is 39 words long.

A Very Girly Day

A college girl enjoys a weekend to herself while everyone in the house is away on vacation, doing things that she would never do with her family around.



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This story is 28 words long.

Dare Poker - Part 1: Moving In

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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.



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This story is 64 words long.

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.



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This story is 77 words long.

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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This story is 83 words long.

Summer Explorations

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Summer Explorations

A boy discovers his feminine side while his mom and sister are on their annual girl’s trip.



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This story is 20 words long.

Summer Explorations 1: The Beginning

A boy discovers his feminine side while his mom and sister go on a trip during the summer.



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This story is 18 words long.
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