Crossdressing Stories


Crossdresser in Paradise

Henry and Lisa have been married for many years. During that, time both of them made many little personal discoveries. Among them was Henry’s passion for cross-dressing. When it came out, Lisa was shocked, but understanding. She did not threaten to leave him. Instead, they talked about it objectively. Seeing him in his feminine clothing did not arouse her. She accepted that he needed this in his life and that she could not deny him this. So they agreed to a compromise.

One weekend a month, Henry could wear openly any and all feminine items of clothing that he wished. It started innocently enough, under dressing in just panties, and tights or pantyhose. Slowly over time, Henry began to explore the fullness of his desires.

Lisa while not turned on in the slightest, wanted her husband to enjoy his weekends, so she started coaching and helping him to be more feminine in appearance, and mannerisms while dressed. Soon, she began to feel comfortable thinking of Henry more as a woman. He became her girlfriend.

They mostly hung out around the house. She managed from time to time to get him out of the house in clothing that, except under scrutiny, looked masculine. She began calling him Marissa. So Marissa and Lisa became great girlfriends spend each of her weekends together. It wasn’t long after becoming Marissa, that they started to have conversations about many interesting topics, from anal, role-play, to lesbian and gay fantasies, as well as many straight fantasies involving other men.

For the next couple of months nothing changed. Then one weekend, Lisa took the Friday off from work and put a plan into place, providing Marissa a special night with new clothes and some hot make out session. Lisa revealed her desire to take Marissa with a strap on. Marissa knowing that this was part of both their fantasies to explore, eagerly accepted and soon Lisa was pounding Marissa roughly every month, and sometimes in between as Henry too.

This again seemed to reach a plateau where they were happy, everything was smooth they were enjoying many aspects of Henry’s desires and found a few new ones for Lisa. She never forgot the conversation about fantasies with Marissa and was determined to help her husband live them.

It was Henry’s weekend, and Lisa had made plans for them. Once Henry became Marissa, she would get her dressed to go out this time fully as Marissa. When Henry got home, Lisa had him take a shower and shave everything closely. When he got out, she helped to towel her dry and apply lotion all over her body. This caused some amorous tendencies that Lisa had to squash and keep them on track. She had Marissa put on a matching black silk and lace bra and bikini set. She produced some breast forms to fill out her bra. She had her put on a black garter belt and stockings to match the rest of her lingerie.

Once she was done with that, she sat her down and went to work on her makeup, taking time to accentuate her face in the right way so as to enhance the femininity. Once she was satisfied with the makeup she helped her into a floral print dress with a skater style skirt that fell just slightly above the knees.

Next came the 3 inch heels, and her purse which Lisa had put all of her ID and important needs during her shower. They were ready to go out on the town. Marissa was a nervous wreck shaking and looking all around as they left the house.

“What if someone sees us?” he wondered.

Lisa reassured her, “Anyone looking would see two women out on the town for the night and nothing more. However, we are going to a drag show so there shouldn’t be anyone there that we know. Even if we do they will not likely say anything because of where we are.”

They made it to the bar without Marissa fainting although he was almost hyperventilating. He was oblivious to the stares as they made their way into the bar and found a small table to sit at. Lisa ordered them some drinks. Marissa took the first drink and slammed it down his throat, causing first a small head rush and second a reapproach from Lisa on how to drink properly, by sipping through the straw. When the second drink arrived, Marissa sucked down about half before Lisa stopped her again. “Slowly” she chided again, “We have all night, just relax, and enjoy the show.”

Soon enough the floorshow started and drag queen after drag queen took the stage performing, and showing off their assets. Marissa had begun to relax, and enjoy the show, when a man suddenly walked up to the table and asked if he could join them. He looked horrified at Lisa who calmly said sure. He asked what they were drinking and ordered a round for the table.

As they sat sipping their drinks and generally chatting, Lisa told him that they were sisters and Marissa was single and she was married but they weren’t really looking for anything but a good time tonight. He graciously acknowledged the let down with a smooth comeback ” How about we just enjoy the evening as it comes with no expectations one way or the other?”

Smiling they agreed and after several more drinks they managed to get Marissa on the floor with Gary. They danced for several numbers Marissa losing quite a few inhibitions to the alcohol and to all the attention from Gary. When they returned the table she grabbed Lisa and went to the ladies room, after doing their business, he was frantically trying to get Lisa to get them home before Gary found out he was a man and hit him or something. Lisa calmed her down, knowing that some of it was the alcohol but also knowing that she had the server dilute his drinks so that Marissa was more in control than the alcohol. “Just let it happen, nothing will happen that you don’t want.” Lisa said.

Lisa led her back to the table, and she looked at Gary, “Gary, Marissa here wants to take you home with us, I told her as long as you were OK with it, that you and her could use our spare room for the night but I will not be joining you two. What do you think?”

Marissa’s mouth dropped open. Gary immediately said okay.

He paid their tab, put his arm around Marissa waist, and walked out to Lisa’s car. He opened the back door allowing Marissa to get in. She flashed her stockings as she slid in. Then he went around and slid in next to her. Lisa drove, as she drove she couldn’t help but watch in the mirror as Gary gently and loving made out with Marissa. At one point as he was kissing her neckline gently, he moaned and pushed him away, “I can’t do this, I’m… I’m… I’m a man.”

Gary looked him in the eyes, and said, “I know” and brought him in for a passionate kiss. Marissa was shocked and just couldn’t resist his kiss as they drove towards home. Marissa felt like a crossdresser in Paradise.

The End.

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  1. Wow very sexy story I wish my wife would do the same to me xxx

  2. I experienced a similar evening many years ago. It was probably the most nerve wracking night of my life!!!!!! I got through that first time and after that occasional repeats and it just got more fun every time!!!!!
    Good for Marissa and Lisa!!!!

  3. So sexy, imagining my wife dressing me up. Thanks for the story.

  4. I am half way there ,love the story and showed my other half who was happy withit

  5. No , that is to much, me and my wife we do same but never let some one , if she try i will leave becouse that is not true love, if i do same she will leave that she told me so no one need just me and her we need to be happy and join not some one else

  6. Wonderful story.
    I look forward to this someday, one can always fantasize.


  7. My name I use daily on “social media” is Daisey, and for the most part everything that was stated in the reading before has happened with me, except for the part the “wife” was OK with the CD. my situation, is she isn’t very accepting, well… she says she is, but her “style” and mine are WAY different. She doesn’t like being TOO girly, and I love it. I haven’t tried to “fully” dress up, from the comments she makes when we do go ut looking for newer styles for me to try on, she is usually in and out of the store, I want to stay a few hours to say the least. We also have been married for 8 years this 13th of july, and have been together for 10 years total. I picked up the CD thing at 15 or so, and it has progressed further since then, just SO much going on with this virus BS, that it is harder to get back to normal with everything going on. I would like to go to a “drag show” but don’t know how , and someone to go with would prove very useful verses with the wife. It’s almost very stressful just to keep hiding everything inside… I wanna do way more.

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