I have cross dressed since a young age. I am currently involved with a woman I want to marry. She however is content at how things are now. I encouraged her to take on other male lovers and she did without any hesitation on her part. She helps with my cross dressing and my makeup. I am always cross dressed except during the work week. I have even gone out in public cross dressed as a female.
She has many lovers during the three years we have been together. I am okay with her finding real men to have sex with. I really enjoy watching her being pleasured with a cock bigger than mine. I am allowed to jack off if I wish as she is being bread by a big cock. Sometimes I am allowed to put my cocklit into her used pussy and hump it until I cum. This in only after a real man has pleasured her and filled her with his dominant cum. She can not feel my small cock so she just lays there until I finish which takes only minutes. I love it when she lets me have her used pussy after a man has used it. That is the only time I ever get to have my small cocklit in her and then only if she allows it. This is more for her amusement than it is for me to have sex with her. She enjoys seeing how excited I become and how hard I try to penetrate her.
One night when out looking for cock for her we met a black man. I never cross dressed when looking for cock for her. She had never had a black guy before. I asked if she want him since I knew she could have him if she wanted to. I encouraged her and when I said they are known to have big cocks she was all for it. He came back with drinks for all of us and I asked if he wanted to come back to our room for a few and maybe she would let him fuck her. He smiled as he looked at her and she smiled back asking him if he was interested? Sure he said and when we finished the drinks we were off.
I told him to ride with us knowing that he would have to stay over night and she would be in his bed all night. When we entered the room she dropped her close to the floor and stood naked. She told him to strip and told me to make them a drink so I did. Returning with the drinks she was on her knees licking the biggest cock I have ever seen. I told her she could have sex bare back since his cock was so big. Smiling she stood up and pulled him to the bed saying to me I could take pictures if I wanted.
He laid on his back and she fed his cock slowly as she lowered on to it. She told him not to rip her pussy and he assured her he would be genital. Her pussy was stretched as big as it had ever been stretched, once she had it all the way in she sat still on it letting her pussy adjust to it. I asked how she felt with such a big cock in her. It feels great she said, she loved the stretched feeling and so full of cock. She started slowly humping his cock as he played with her tits. I now had my pants odd and he pointed out my small cock and they both laughed at me. My cock grew stiffer as they laughed at it.
Soon she had her chest down to his as they kissed passionately she was soon humping his cock. What a sight from her rear, a big cock going in and out of her now well lubed pussy. You could see her white cum on his cock from her many orgasms she had reached now. She was slamming her cunt down on it with all she had riding it until she collapsed on top of him shaking from her many orgasms. Laying with his cock still penetrating her stretched cunt. Not saying a word she lay there content. I asked if I could have my turn and she laughs saying she would never even feel my little thing.
When she finally found strength to remove herself from his cock I saw his cum run out of her hole. It stayed hanging open just like I always wanted to see it. She asked if I was happy spreading her legs showing me her gaping hole. Oh baby that looks so nice I told her. I begged to have my turn and she agreed with discuss on her face. She was correct I could not feel her at all and shot my wad in less than a minute. She asked if I ejaculated? I told her no but really I did and did not want her to know how fast I squirted. I told her she was to stretched for me to feel anything.
That night she slept in his bed and he fucked her once more before I fell asleep and once more in the morning as I packed up and took out our luggage to put it in the car. Returning she still had his cock inside her pussy. laying on top of him she said her pussy would never go back after being stretched so much. I told her I was ok with that, I still had her ass to fuck. Smiling she sat up on his shaft telling him she did not want to leave. He told her she could stay with him if she wished. I interrupted and told her she was not staying with him. I would be ok with her going and staying over night with him from time to time. I told her to go clean up and we had to get going. She did as I asked and we took him back to his place. We exchanged phone numbers and took his address down before leaving.
On the way home she told me she was still leaking from her stretched pussy. I also found out he had his cock inside her almost all night. I knew she was stretched and possibly would never go back in shape. I asked if she wanted to see him again? She hesitated a bit but I knew she did but did not want to admit it. I said I think you had a good time and liked his big cock. You should make it a habit of seeing this guy regularly. She never said a word so I asked if she was alright? Yes she said. Well don’t you think you should make this a regular thing I asked again. She replied saying, I do not know if it should be a regular thing but once in a while would be alright. I knew right then she would become a gaper and my release would be using her ass only. I was alright with this because I always wanted a slut with a gaping used pussy. This was my trophy wife I wanted to marry.
Three weeks went by and I was not going to bring it up again waiting for her to say something. By the end of the third week she said she had been talking to her black stud and he wanted her to come and spend the weekend with him. I asked if she was going to go and she wanted to know if it was ok if she did. I told her these words “Only if you come back with a gaping pussy”. She looked at me and said, it will be. I told her to only wear what she goes up wearing and do not take any other close. I asked if I could pick out her outfit which she told me ok. I picked out black short shorts the ones where her butt cheek almost hangs out. Knee high boots with a white pushup bra and a white shear blouse. I told her to remember she would be leaking once he had finished with her so she took a towel for the car set. This was a Friday evening and she gave me a kiss and off she went.
Returning the following Monday I was already at work. When I came home I asked to see her pussy and it was indeed gaping some. I was as happy as could be and she was pouting telling me she did nor want to have a gaping pussy. I assured her I was alright with it but other man may not be. I told her if she married me I wanted her to continue seeing her black stud. She said nothing and went to bed. I knew she was not going to let me have any of her pussy tonight. The next day when I came home from work she told me to put on the sissy outfit she laid out for me. I did as she told me to and she did my makeup as I talked to her about how she enjoyed his cock.
She told me I had to dress all the time when at home and not just weekends. I said I was alright with that. When we sat down and talked she told me she preferred me cross dressed rather than trying to be the guy I wasn’t. She continued to say this is what she wanted. I was to be her sissy maid. She wanted to continue seeing her stud but I would no longer have any intercourse with her, no anal or pussy. I would be allowed to masturbate when she allowed it. The other thing she wanted me to agree to was, I had to wear a chastity cage. I asked if I did not agree to these terms what was she going to do? She hesitated then said, leave you. I asked how long did I have until she needed an answer? By this weekend before I go back to see my stud. I was at a total loss for words sitting dressed as a girl and being given a choice such as what she gave me.
I cross dressed all week when at home and when Thursday night came and I was all dolled up she asked if I had made a decision yet? I told her I had not and said I had another day to make up my mind. She told me she would be gone when I came home from work. I told her that was ok and I will be here when she comes back. We continue our relationship and I did concede to her demands. Her stud now lives with us and she has become his property. I sleep in a separate room with the door removed. I am their sissy maid who takes care of their house chores. I still work a full time job as does her lover. We have been this way for the last year and I am let out of my chastity just as she promised. I get to watch her fuck his enormous cock as I masturbate. She tells me one of these days she will let me lick her gaping pussy.
“SM” Sissy Maker