Cross Dressing Lifestyle Pt. 01

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Couple Discover a Love for Cross Dressing.
1.1k words
4.52
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Part 1 of the 2 part series

Updated 06/11/2023
Created 09/17/2022
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damkkr
damkkr
23 Followers

Back in the 90s (when I was a teen) I remember we were given an assignment in French class to learn words for clothing items. Our teacher gave us magazines (Elle, Red Book, etc.) to look through and cut out images in order to associate the French words.

One of these magazines had a "Sex Help" column. I remember reading that column and being so excited that it was about a couple crossdressing, for which I also had desires.

I've recreated this letter below. I've then written the story from the mans perspective, I hope to add a story from the woman's perspective as well.

Enjoy!

Dear Ms.X,

I am writing with questions about my marriage. Some things have changed between me and my husband in the past few months and I am not sure what they mean or how I should feel about them.

Three months ago my friend invited us to a fundraising event that involved a fashion show where men volunteered to dress in drag and walk the catwalk. My friend convinced my husband to volunteer as a model.

The day of the event my friend helped my husband get ready/change outfits while I watched the show from the audience. After the show I met my friend and husband backstage. While it was a little strange to see my husband wearing a dress, heels, makeup and a wig, I must admit that I felt myself flush. I love my husband, he is a very attractive man--but seeing him dressed was a turn on I did not expect.

As we prepared to leave my husband decided he wanted to stay dressed for the drive home. Before we left my friend pulled me aside and told me that he was very enthusiastic about the entire show--and, while she didn't say anything to him, it was obvious that he was "excited" about getting dressed up.

By the time we got home I couldn't help myself. We had sex with him still dressed as a woman--and it was perhaps the best sex of our relationship. I've never felt him so hard and yet he was attentive to me in ways that he had not been before. When we were through we fell asleep with him cuddling in my arms.

Between work and home lives the next few days were fairly normal. About midway through the week, however, my husband came home from work and, like usual, went upstairs to change. However, when he came down he wasn't wearing his normal comfy clothes--he was wearing one of my skirts and one of my blouses. He made eye contact, but neither of us said anything. Again, I felt a certain flush. We had dinner and watched some TV--but I noticed that he not was not only more affectionate but he was more deferential. That night we again made love, which was again amazing. However, I found myself taking more control, asking for what I wanted and telling him what to do. The more I asked of him the more turned on he became.

This continued for the next few weeks. Each night my husband came home and changed into my clothes--skirts, dresses, panties and bras, even nylons. While we did not have sex every night, our frequency and intensity did increase signficantly. That first weekend I helped him shave his legs. By the second week he would not only change into my clothes but he would put on his wig and I would help him with make up--until, after helping him he got to the point of doing his own make up.

On the weekends we would run any errands first thing in the morning, then he would dress for the afternoon as we did things around the house. When dressed he became more helpful than ever, helping with cooking, cleaning, and laundry. In the bedroom I was in charge and experiencing more pleasure than I ever had in my life.

After a few weeks we decided to try going out with my husband dressed. I made a reservation at a restaurant the next town over, I bought him a nice dress, and I drove us to our dinner. We were both quite nervous--what if we were pulled over, what if the waiter or waitress realized he was a man dressed as a woman? Regardless, we had a wonderful dinner and I drove us home. When we arrived home I couldn't wait any longer. After passionate kissing I beckoned for him to follow me into the basement. In our basement I asked him to sit in one of our arm chairs. I had ropes with which I tied his hands and feet to the arms and legs of the chair. Stepping back I looked at my husband. Seeing him there, helpless, hands and feet tied, his made up face looking back up at me I felt a wave of convulsions course through my body. My knees went weak and,standing there, fully clothed, not touching myself, I had a powerful orgasm. When I finally regained my composure I expressed my desire to continue with this lifestyle we've discovered.

This is the most sexual thrill that I have ever experienced. I don't want it to stop. But I worry--is there something wrong with us? Why am I so turned on by my husband in my clothes? Is my husband gay? Am I a lesbian? I am not attracted to other women. Is this ok?

Sincerely,

xxxxx

Dear xxxxx,

I will start by saying no--there is nothing wrong with you or your husband. From what you have described you have discovered that your husband is a crossdresser and possibly a submissive, you are a dominant. This does not mean that your husband is gay--in fact, studies have showing that of the 5-10% of men who crossdress the vast majority are straight and many of these men are married. Many crossdressers simply dress to relax, although some men also find this to be erotic. I think your husband falls in between the two.

Nor does this mean that you are a lesbian. You are attracted to your husband and his male-parts, even if they are dressed in womens clothing. As far as your being dominant and being aroused by being in the lead in your relationship--it seems that this comes naturally to you. Your husband seems to be open and accepting, so by all means continue!

If I have any concerns with what is happening in your relationship it is that you have not really discussed how you are feeling. I would encourage you to sit down and have a conversation. Talk about how you feel, ask your husband about how he feels. Be open, honest, and non-judgemental. It seems that you are both already on the same page--communicate and continue to enjoy one another and these things that you have discovered!

Sincerely,

Ms.X

damkkr
damkkr
23 Followers
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5 Comments
4Leather4Leather10 months ago

See myself in this store starting out. Boy the memories came back.

AnonymousAnonymousover 1 year ago

Is this a story or a discussion?

SissyCrissy6245SissyCrissy6245over 1 year ago

This thread takes me back decades to an issue of the Penthouse Letters magazine. Three, maybe four tales of gender bending Fun. These erotic "letters" had Me "tenting" my nylon Bikini panties.....xoxoxo

AnonymousAnonymousover 1 year ago

Good start. Please continue it.

AnonymousAnonymousover 1 year ago

She needs to go the opposite way - dress in man clothes during their sexual times. Underneath her pants and boxer shorts will be her strap-on; ready to fuck her sissy bitch.

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