Life updates

Heey guys and gurls! Hope you're all good and well, i been trough a lot since divorce, lookin into myself to discover who i'm trully am. Started hrt in oct/2025, talked to family and close friend about being transgender and what to expect from the future, and for my surprise i have a lot of support until now. I also have experimented being bottom in a few opportunities with a transwoman, going out full femme, and every step in this way i was felling more like myself than anytime in my life, and i love it every second. Its just too difficult to support myself working in a regular job as a… Citește mai mult

Postat de Jackfap420 26 zile în urmă

Recently Divorced

Well, what some of all predicted my wife ask for divorce, she said that she lost the admiration for the man i used to be and even that she said the crossdressing wasn't the motivation for the divorce, it played a big role in her decision, it was hard in the first days and it still is but now with help I'm getting through. So now im available to go on and chase what i want and discover myself, I'm open to experience dick for the first time and go and try to live as a woman in some friendly places, not going full time but experience being a woman in day-to-day life and figure it out if I'm trans… Citește mai mult

Postat de Jackfap420 7 luni în urmă

Sissy Creed

Goddess Roberta, I'll follow your instructions as I said before, here is the lastest task you demanded! I’m a horny little sissy cum slut. I am being sissified and feminized on a regular basis. Locking my little penis up in chastity and admitting that it is a clitty is so exciting. It means that I have handed over a complete control and I am a submissive sissy slave. My little clitty is being shrunk because I know will forever be pussy free. Yes that’s right I accept that I will never have sex with women again. I admit that I am still sexually attracted to women but they are Superior to me an… Citește mai mult

Postat de Jackfap420 1 an în urmă

Sissygasm achievement

My asspussy is still sensitive writing this, 2 days ago i was alone at home and horny as fuck! While working I couldn't stop thinking about feminization (as almost everyday) and being fucked, so i went on and put my pink chastity cage (cb6000 small) and my vibrating butt plug, while watching some videos and reading some blogs here on xhamster i get that slutty feeling and went on to grab my 18cm black dildo for play, put on some Jessica Bloom videos (I love her content, her voice and the way she talk to the camera I feel like she's here with me, telling me to do slutty things) and started to s… Citește mai mult

Postat de Jackfap420 1 an în urmă

QUESTION FOR CROSSDRESSER/SISSY'S

Today something unusual happened and I wonder if someone have experienced something similar. As almost every home office days when I'm alone at home, i dress up in my wife's lingerie (lace black panties with dark-red lace bra), black shiny leggings, nude heels and a black blouse with some accessories but without a wig/makeup and went online reading some CD's blogs, crossdream.com and suddenly the urge to be more feminine hits me and then I realized that I can't twerk my hips like a proper woman! Soo I go online to find a good twerk tutorial! I find one, the teacher (beautiful black woman) is a… Citește mai mult

Postat de Jackfap420 1 an în urmă

Help me buy my Chastity Cage!

Hi everyone! I need some advice on buying a chastity cage, I need a smaller one but I'm in doubt on which one I'm buying, um thinking on the V5 steel model (nub size maybe) when flaccid I have a very small penis and I'm having trouble to find a good size, any comments or advice are very welcome (as always)… Citește mai mult

Postat de Jackfap420 1 an în urmă

Wife pegging my asspussy

I would never had imagined how great my wife would respond to my crossdressing/chastity sub side, I only regret that I didn't say it earlier in our relationship, but things happens in the way they should be, with only a month that I talked to her and open up about everything that I kept in secret she accepted all very well but at first she was reluctant, know she kept me locked up to 2 days (my cage slips out, I'm working on getting a smaller one for long term chastity) totally dom on the bedroom and today she took my asspussy virginity while in chastity, I didn't cum but that was the best thi… Citește mai mult

Postat de Jackfap420 1 an în urmă

Wife locked me!

Hi!! (Anyone interested) I took the guts to open up to my wife about crossdressing and chastity, everything went well! (Thank god!) The only thing that she didn't like it was the crossdressing but she didn't prohibited (as longs as she didn't see me wearing her things) but the cage and domination, she love it and with only two days she locked me, make me lick her whole, massage her and do everything with a promise that I would get free and fuck her and here Im locked she is sleeping and is enjoying that, as me too.… Citește mai mult

Postat de Jackfap420 1 an în urmă

HELP!How to introduce my chastity cage to my wife?

Hi everyone! I here in need of some advise! I'm about to present a chastity device to my wife (bought one a little bit larger than I needed, 11cm, but I'm a grower so it restrain some of my erection) and I need some advice on how to approach on that, I got a chastity cage, a butt plug and a 14cm black dildo (already try it and it feels awesome, my first dildo!) that I pretend to show to her with an excuse that it is to please her when im locked, I give her multiple orgasms while having sex (orally and penetrating) and our marriage is all good (and monogamous, as we prefer), I'm going to tell… Citește mai mult

Postat de Jackfap420 2 ani în urmă

Married Crossdresser tips

Hi everyone! I'm here asking for a friend ? who's is a married closet CD, how to be open to your wife about it, how to disclose something that are soo important to all of us (CD), any tips/comments are welcome!… Citește mai mult

Postat de Jackfap420 2 ani în urmă
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