I received an e-mail awhile back asking my opinion on cross dressing? This started an e-mail relationship with who we will call J. I told him I/we do not practice it except for me having my husband wear panties sometimes, so am not versed in this activity. I did tell him I would post something for him if he sent me what he wanted to say. Here it is.

He was hoping for feedback and comments, so please do if you are interested.

Though I did not know it at the time my first teenage sexual fantasy were as a submissive male. As a young teen I worked as golf caddie and masturbated to thoughts of me being nude while woman whose clubs I was carrying were clothed, as they golfed they would fondle my cock/ balls , at end of the round if I was good caddie I would get to orally serve them.  A second fantasy began when I would pick up my girlfriend for dates, her Mother would tell me to take off my clothes than train me to orally satisfy her daughter.  With marriage my wife of 40 years and I began an enjoyable sex life starting with vanila sex, use of sex toys, watching porn, Strap-ons, Femdom, together visiting a ProDom, Swinging and now to my surprise Cross dressing.  We are not an FLR/WLM marriage. My wife has gently assisted my femme interest by buying me panties, bra, nylons, dresses, wigs and how to apply make-up. Once a week I clean the house dressed as a woman and we have had fun.  I enjoy the feeling of woman’s clothes and have become a slut for my wife’s finger up my ass as she sucks my tits. The further I have gone down this rabbit hole of cross dressing the further I want to go.  I am not attracted to men, I am straight but strangely enough to me CD/TV porn I find very arousing. I told my wife I want to suck a cock for her but she is not ready to see her man do that. She is ok with me further exploring my femme side with others.  I do not feel like a woman, no hormones, no gender change etc. Been a successfully competitive man in my career and athletically.  I have read submissive males love woman so much they want to become the woman. Perhaps this is just a natural evolution of a sexual submissive male and at 60+ years old I am now comfortable expanding my sexuality.


J in his beautiful attire

14 thoughts on “Cross Dressing

  1. J i too started my decent into femdom in my early child hood years. I too always wished to orally satisfy girls that i went to school with. It all came to a head when i was 15, and i came under the spell of a woman who was 39 years old, and her 32 year old sister. With them i came to know just how many ways a dominant woman would/could use a submissive male. I learned how to orally satisfy a woman, how to drink pee and enjoy it, how to care for a woman’s intimate garments and also wear such garments, in short how to dress like a sissy, act like a sissy, and how to satisfy a man with my mouth, this too i enjoyed. My time with these sisters lasted until i joined the Army when i was 18.
    I married a most wonderful woman and gradually introduced her to the femdom life, served her orally multiple times many days, and happily drank her golden pee almost every day. But she unlike your wife, took to the idea of me giving a man blow jobs while she watched and i even enjoyed drinking their pee too. We continued in this way until 3 years ago, when i had a stroke on Feb.16,2016. We stopped all the drinking activity, much to my sadness, but i still serve her orally 3 or 4 times a week. I am 82 and closer to 83 than 82, and i no longer dress sissy but i still wear panties and a bra, and pantyhose, in fact i was wearing the same when i was taken to the hospital when i had my stroke.
    Hopefully your wife will come around and try having you give a man oral service while she watches. It is wonderfully thrilling and even humiliating to kneel before a man and get him hard and then take him into your mouth and bring him to ejaculation and then swallow it and then when he has gone soft take him again into your mouth and let him empty his bladder into your mouth and drink it without spilling a drop.

    Liked by 2 people

    1. I am sorry Ma’am, i did not mean to be anon, but i got distracted and ended my note before i meant to, and also used the wrong email address.
      I meant to tell J, that i and my Wonderful Mistress Wife have learned thro the years, that man “Straight” men would never consent to have a man give them a blow job, the same men would jump at the chance to get a blow job from a sissy . I always was fully dressed and made up when i had to give a man a blow job, and i will tell you that there is always a deep thrill and Humiliation when doing so. These straight men dearly loved to face suck deeply and sometimes brutally during the blow job. I have even had men ask my Mistress if they could spank me, and i was spanked and belt whipped a number of times by them.
      Slave Kendra

      Liked by 1 person

      1. Hi SK:
        Thank you for your reply:
        I know its different for a man but It is such a wonderful feeling to bring a man off with my lips and tongue. I love to feel him swell at the moment of release and feel the hot spurts in my throat. I have never had my husband suck man off but he has cum in his own mouth many many times.

        Liked by 1 person

  2. Cross-dressing and sissyfication are not my cups of tea. The concept of feminization does not appeal to me. Not something I would ask for. I like to be perceived as manly in every aspect except that my maleness can be easily tamed, controloed and dominated by the right Woman, by Her very Feminine nature. I am not ashamed to be and like being pussy-whipped. And as such I think I would get on my knees to suck my Wife’s bull’s large cock if She had one and asked me to do it or to be taken anally by him or to even lick his creampie from Her well-satisfied pussy. Drinking pee – Her yes, gladly, his no way, unless She physically forced me to. But I am safe in this regard, She would never do this to me.

    Liked by 2 people

  3. Crossdresser, sissy, transgender, transsexual, gender bending, gender fluid and even gender queer are all different aspects of gender identity disorder. Weather there is a disorder or not is greatly discussed.
    My husband cross-dresses and he is dammed good at it. He confessed this to me when we were dating. It seems his second wife enjoyed it and exploited it. It really doesn’t do anything for me but I allowed it and used it to bring excitement into our already exciting relationship. I turned him into my sissy and used the humiliation to advance his servitude to me. By incorporating chastity, tease and denial the boy is on pins and needles at all times and will “get busy down there” with just the snap of my fingers.
    We dress up and go out, I dance with men and suggest he do the same. He gets plenty of attention and men want to get to know him better. He serves as my maid at times and I have shown him off to my girlfriends and to some of the men I include as friends. We don’t do much dressing up anymore but feminine items are always included in the boys attire. He always carries a purse and wears women’s shoes and slacks or jeans. this adds to his humiliation and if the chastity device would allow it he would be hard. Keeping him at least partially feminized adds to his fear of being cuckolded and I use that to further keep him on edge


    Liked by 3 people

    1. Hi Janyne:
      Thank you for replying to this post. J is hoping for feedback.
      I get the idea email conversing with J that he a normal healthy male, I don’t believe his wife wants to have him suck off anyone. I think he just enjoys the feeling of woman’s clothing, the sexy panties, the bra’s etc.
      It sounded like his beautiful wife supports his desire to cross dress.
      I think what ever turns you on, you should do it.
      Thank you for all your feedback on my blog, many of the men really engage with you and would love you dominating them, You have a large following, thank you for participating.

      Liked by 2 people

  4. Dear J.,
    That is wonderful that you and your wife can express yourselves sexually so well. As Dorinda says, you should do whatever turns you on. Like you, I adore Women and Femininity so much that I want to be emulate Women and take the submissive ‘feminine’ role. And feminine clothing looks and feels so good. When I am wearing my girlie clothing, I am transformed both physically and psychologically. I am not at all attracted to men as such, but some feminine gurls are so very attractive to me. It must be their femininity, maybe I’m a lesbian after all!
    Tris Neill

    PS- You look great in that outfit!

    Liked by 1 person

    1. Hi Tris:
      Thankyou for reading my blog. I appreciate it very much.
      Thank you for your honesty and replying to J’s post.
      I am always very interested in FLR type of sexuality. This may not be related but J says he enjoys my blog.
      Asan older and wiser woman, I enjoy understanding topics I would have not understood when I was younger.
      Anything sexual, that is, that makes a man hard, or a woman wet. Even without contact, I believe it is all in our mind, I so love to stimulate my husbands mind with out touching his penis.

      Liked by 1 person

  5. I am not into feminization or being a sissy. But the idea of being forced to wear panties does excite me. My Queen doesn’t care for that so it won’t happen. However if it works for you J, then by all means enjoy it.


  6. I hope I didn’t sound judgemental in my first comment. Like I said, not my cup of tea, but all sexual activities between consenting adults are fine with me. Nothing wrong with cross dressing, or the wish to suck cock for your Wife as a straight man (a little bi-curious perhaps? I think I may be too) if that’s what excites you J, I think you should explore and enjoy it. It is great that you can share your sexual desires no matter what they are with your wife and that She supports you and you can enjoy it together. I agree with you that as we mature we become more accepting of our own or others’ sexuality. I am exactly like that.

    Liked by 1 person

  7. My wife requires I dress every day now since I work at home. I have a very full wardrobe with at least 22 dresses I wear with bra, panties, garter belt, lace top stockings, high heels and wigs. I dress to please her. I shave my body smooth and wear nice perfume.

    I wear panties and a bra all the time when I go out.

    I really enjoy being her Sissy Housewife Husband now.

    Liked by 1 person

  8. I am a Married Sissy Husband and very proud to keep my body shaved smooth and wear dresses and lingerie all the time at home. I only wear garter belts and lace Berkshire stockings. My high heels are at least 4″. I think I have 22+ dresses now too. I love dressing pretty for her

    I orally pleasure my wife all the time both pussy and ass. I am not allowed orgasms for up to 3 months at a time and when I am allowed I must ask politely on my knees and then let her use a Hitachi Wand to make me squirt onto a spoon which is immediately fed to me. I enjoy my sperm feeding. Sperm is to always be eaten fresh and warm.

    I am also given her pee in a very large wine glass. It holds her full bladder or a 750 ml bottle of wine. I must again ask politely for a glass of her “wine and then kneel and hold the glass as she fills it. I then drink it on my knees as she smiles and enjoys my service as her Pee Drinker. I love drinking her wine and I thin k I get the benefit of her hormones as well.

    As far as punishment my wife and I enjoy twice a day daily spanking to maintain my Obedience and Submission to her. These are hand spankings and they generally last about 5-10 minutes.

    Before work I report to her naked and must have an erection. The ED meds guarantee a very hard erection. In the afternoon I must be in position at the love seat in our front window leaning over with my panties pulled down to my knees and again with a very hard erection. She wears gloves and really likes to beat my ass and tell me how much of a Sissy I am and I always agree and ask for more.

    More serious punishment is always done spread eagle restrained and with her Spencer Paddle, Wooden Handled 2” Strap, Flogger or Cane (or all of them). I get my age with a serious punishment and I will be 60 soon. Serious punishment has helped me become a very devoted obedient and extremely submissive Sissy Housewife Husband.


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