The Mis-Adventures of a Sissy Slut

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For several months I had been in contact with “Bob” (not his real name). We shared countless hours talking on the phone and emailing back and forth. There was something about him that was different then most submissive men that contact me. Although he is an alpha male in his day to day, he had a true desire to fully relinquish control to one mistress. It wasn’t just about his kinky sex fantasies but a welling desire to fully submit. The challenge is that he is married.

Bob has been married to the same woman for 25 years! Although they have a wonderful family and home life he has lived a secret life for most of it. When he was in his 20′s he began to experiment with dressing. He started with panties and bra. Being feminine put him in touch with his sexy side and the humiliation really turned him on. But like most he purged dozens of times and went back and forth for years. He never shared any of this with his wife. She once found his “pretty things” in a bag hidden in the attic. When confronted he told her he only used them to masturbate. Since that day sex took a new turn and she almost seemed disgusted with him. The cum stained panties just painted an image she couldn’t get out of her head. So for the next 10 years Bob kept his girlie things at the office and his dressing for out of town business trips.

When we first started talking there was one point where he literally broke down and cried. It wasn’t about being feminine or being a girl. He didn’t want to be a girl. He felt frustrated having to hide his sexual fantasies and felt like he was going crazy! He visited a few professional dominatrices and had bad experiences. When we talked we talked for hours really get into each others head. I understood where he was coming from and the need he had to express himself.

Public Humiliation Sessions

We started with a few assignments and dominant phone sex sessions. At first I wasn’t sure if he was serious or not so I made him jump through a few hoops to prove it. If he was going to be MY sissy slut then he would soon learn that although I can about his needs, its all about me! I sent him to Macy’s to purchase panties and to ask for help. I sent him to Walgreen’s to buy lipstick and put it on right there in the store. I sent him to a lady’s salon for a mani and pedi. Every single task that he performed he had to take a picture of his items or provide some type of proof. I even sent him to an adult bookstore wearing a ladies blouse, red lipstick and carrying a ladies handbag. He was so nervous and I was on the phone with him the whole time. I teased him about going into the booths and sucking some cock. Although he had never done this I knew he would have done it for me. But I didn’t want to push him to hard on such an intense public humiliation outing.

We had a great time doing public humiliation sessions. I really saw Bob coming out of his shell and there were times where we both laughed until we peed our panties. As time went on it was clear it was time to take it to the next level. I had been going back and forth between New York and South Florida for a few years and decided I wanted to meet Sissy Slut. I thought Sissy Slut was going to jump out of his skin when I asked him to meet me in South Florida and grab a drink at a local gay club.

Meeting a Dominant Mistress

Although Sissy Slut had been to a few professionals he had never actually met a lifestyle Mistress face to face. I instructed him to wear full bottom pink sissy panties and a pink sissy camisole under a white button down shirt. He was also instructed to have a bag in his rental car with high heels, wig, stockings, basically an entire outfit.

When I arrived he was already sitting at a table waiting. He was so nervous and literally shook when he spoke. He had a drink waiting for me. Immediately I told him to take off his white button down shirt revealing his pretty pink sissy cami. People in the bar looked and smiled but it wasn’t as if we shocked them. I then had him walk out to the car, in his cami and put on his pretty high heels and come back to the table. I watched him walk back in and strut across the room in his 5 inch hooker heels! I reached into my bag, pulled out lipstick and put it on him. By now we had a small collection of people watching us, pointing and smiling. We danced and had a great time. A gay male friend of mine was there and I asked him to slow dance with Sissy Slut. It was an amazing experience.

The Full Sissy Make Over

The next day I had Sissy Slut meet me at a salon where he had a full make over. This included mani and pedi, professional make-up and his legs & private parts waxed. Afterwards he changed into a dress, stockings and heels. We fixed his wig and touched up his make-up. This was the very first time Sissy Slut had ever been completely made over, as a woman and taken into the public. Of course Bob didn’t fully pass as a girl but that’s why it was SO much fun! I took Bob shopping, out to dinner and more dancing. Afterwards we went back to my suite for some kinky play. I ad been training the slut to take a 9 inch dildo in his girl hole but this was the first time he would be penetrated while it was strapped to my hips in a harness!

Sissy Slut gets Used by Strap-on Dildo

Fist I made the slut strip down to panties, stockings, garters and heels. Then on his knees to suck my big 9 inch strap-on dildo. I then made the horny little sissy lick my ass before I threw him down on the bed and fucked him like a girl!

Are you jealous?

We have some great adventures planned. What do you think Sissy Slut should do next? Tell us your ideas in the comment section below. If I use your idea I just might give you an assignment of your own. If you subscribe to my blog (see a place for your email on the left) you’ll get an email when I post a new story.

 

 

 

 



Recent Comments

6 Comments

raven On February 1, 2013 | Reply

What a great story! Yes. i am jealous. i would love to see pics of him stripped down and being fucked by your strapon. I think the next step is for him to suck a real cock.

    Natalie On February 1, 2013 | Reply

    I think you are right Raven. Although its on his list of limits I get the feeling that he really wants to be forced to suck cock but I promised to respect those limits. IT doesn’t mean I won’t expand or try. At some point the naughty little sissy slut will be begging for that man meat!

raven On February 2, 2013 | Reply

He must have been thrilled to be able to meet you in person and have you make him over and take him out in public. He must know that at some point he will have to suck cock.

daz On September 9, 2013 | Reply

i think you should take him to a salon and he has acrylic nails so they stay on for days so when he wakes up he realizes that he is still a sissy and also take him shopping to try on heels and womens clothes, i would love a mistress who i can do all that with

    Natalie On September 12, 2013 | Reply

    That’s a good one but I’m not sure realistic. Most of my sissies are married. But I do love having fun while they are out of town. When they are home sissy assignments have to be kept to be more discreet.

Jim On September 11, 2014 | Reply

I think you should go all the way and make him completely dress up in full fem attire with wig heels breast forms the works and go to the mall while you film it. That’s what I would like to be made to do for a dom mistress then taken to a glory hole to suck cock and told what a slut I am.

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