What came first you being a cuckold or you being a sissy? If you were a cuckold first did your wife make you a sissy or did her Bull suggest it. How did you start>
Sissy
- Thread starter Biggdaddy412
- Start date
Sissy first for me. Probably started at age 14 or 15. The cuck thing interested me later. After I got married. (Hard to be cucked with no wife, amirite?)
The good news is my wife actually indulges me with my sissy behavior most of the time. So that’s nice. The bad news is she has ABSOLUTELY no interest in me being a cuckold in the modern sexual connotation. She’s outright refused any of that. Although she does have boyfriends, it’s never when I’m around. She never talks about them and she asked that I don’t ask about them.
The good news is my wife actually indulges me with my sissy behavior most of the time. So that’s nice. The bad news is she has ABSOLUTELY no interest in me being a cuckold in the modern sexual connotation. She’s outright refused any of that. Although she does have boyfriends, it’s never when I’m around. She never talks about them and she asked that I don’t ask about them.
Sissy first for me too. Repressed for years due to parental shaming/scorn. It wasn't something I indulged in when Ms and I first got together. Over the years pandoras box was opened.
Unfortunately she prefers manly men, once she'd seen me feminised I lost some physical appeal to her. That started a self reinforcing cycle where sex was often rebuffed and I'd dress/play either on my own or in her presence. Eventually there were indiscretions on her part and finally an affair which I was largely oblivious too until I was informed. We got through that, but a seed was planted.
I worked out that on many a night when she'd been undressing for her lover. I was at home dressed up and having fun of my own. After a while this was a go to fantasy whenever I felt horny. Some time later, once I'd worked up the courage I asked her to do it again. That began a very fun, but all too brief, time in life...
Unfortunately she prefers manly men, once she'd seen me feminised I lost some physical appeal to her. That started a self reinforcing cycle where sex was often rebuffed and I'd dress/play either on my own or in her presence. Eventually there were indiscretions on her part and finally an affair which I was largely oblivious too until I was informed. We got through that, but a seed was planted.
I worked out that on many a night when she'd been undressing for her lover. I was at home dressed up and having fun of my own. After a while this was a go to fantasy whenever I felt horny. Some time later, once I'd worked up the courage I asked her to do it again. That began a very fun, but all too brief, time in life...
The sissy side is what I first discovered. I took advantage of moms closet being so organized that it resembled store displays. All shoes in their boxes and dresses perfectly aligned. That was partially what drew me to her girl things. She would leave to run errands and I just had to try on some things. Before I knew what I was doing I was wearing hose heels and dresses every chance I got. It was a sad day when I realized I could no longer borrow her things because I outgrew them.
TSJenny2021
Male
jess4bbc131
Male
sissy first ever since i was 12 i wanted to be a sissy for bbc since i first discovered porn
TSJenny2021
Male
and some people think that is a bad thing
Attachments
She has boyfriends its pastime you get to dress up and have boyfriends she does it when you're not around you do it when she's not around if she catches you tell her you don't want to talk about it.
churchladyhubs
Couple
Crossdressing for my best friend in high school
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