Bending over and dropping my girlie knickers for anal sex in chastity

A sissy slut doesn’t deserve to get hard while a real man fucks his arsehole!

Cross-dressing sissy in tiny blue dress and white stilettos

Locked Sissy Transvestite

Being in lockdown has given me plenty of chance to think about some of the sexual fantasies I’m yet to fulfil. The last few months have seen me tick off lots of long-held sissy dreams, most notably coming out to my ex-wife and agreeing to let her have the key to my chastity cage. And that last one has set me thinking about another dream of mine. And that dream is to be shafted by a well-hung stranger with my cock remaining locked throughout.

I have always had a strange relationship with my penis and love seeing it locked in its silver cage. It deserves to be in prison because it’s far too small to please a woman; it never used to get hard for my ex wife; and I always had to use sex enhancement pills to have any hope of achieving an erection. Of course, my dream would be to have it replaced with a vagina, but caging it is the next best thing – and I love the thought of teasing it by getting fucked while it’s trapped in its cage. Because the only thing that ever seems to get it excited is when something big and hard penetrates my rear-end.

Sissy transvestite hitches up dress to expose black knickers through nude tights

Chastity Devices For Sissies

I have had anal toilet meets with studs in the past, but not since my ex wife has taken ownership of my chastity device. She keeps the key in her underwear drawer and only lets me release my cock if I beg for it and agree to tell her exactly why I need to be released. So if I do fancy masturbating next week, my wife will want to know what I will be wearing and what I will be thinking about, reading or watching – and pretty much every juicy detail of what I’m planning to do while released. I have to either put it all down in an email to her, or tell her over the phone.

It’s humiliating, of course, but I get a real submissive thrill from telling my ex wife all my forbidden sissy fantasies. I especially love telling her what outfits I enjoy wearing and discussing with her how those outfits make me long to suck cock and get fucked by real men. These were the kinds of things I would have loved to tell during all those years of marriage when I was failing to get hard and pleasure her. She deserved to know back that then she was married to a failed sissy slut, but at least she knows the truth now and is getting some payback. Because with the key to my clit in her underwear drawer, she definitely owns me now!

Live Sissy Phone Sex

Live sissy transvestite phone domination chatline