SISSY CUCKOLD HISTORY 982.
The Cuckoldress wife knows that her feminized sissy cuckold will because of her heavy dating schedule be on its own for extended periods of time and this places undue stress and worry on her while she is out trying to have some fun!
Let’s be honest how can you expect your wife to fully let her hair down and fuck like a slut to get the orgasms she wants and to give the best of herself to the man or men she is with when at the back of her mind she is anxious that your alone at home fiddling with yourself, jamming things up your sissy pussy and generally doing all the nasty things feminized sissy cuckolds are prone to do when alone, as the saying goes “The devil makes work for idle hands!”
So, you can understand why nearly all Cuckoldress wives turn to things like restraint or chastity and by chastity I mean both types as if a sissy cuckold’s penis is capped off it will because of its nature resort to fucking its anus with any cock like object to get a sissygasm.
Thus, fully locked up the Cuckoldress wife can really go for it in the slut stakes whilst out.
But and there is a but, A growing number of Cuckoldress wives are not even satisfied with these methods and they have concluded that like some baby the feminized sissy cuckold needed sissycucksitting by a woman that she can totally trust.
And that woman invariably is the Cuckoldresses Mother because her mother is the one woman she trusts totally to be 100 percent reliable in her feelings towards her sissy cuckold son in law thus the sissycucksitting the Mother takes on for her dating daughter will always be a trial of sadistic brutality towards the sissy cuckold that involves nonstop emotional and physical torment and torture.
nacktsklave| Mar 26, 2026
I took them myself using the self-timer. But it would be much cooler if someone else took these photos, and even more daring ones.
"It seemed like age ago since the fat old guy next door had said "I'd love to fuck a sissy, but I doubt I'll ever get the chance", he will now our wives are out for the day."
"i love this kind of androgyn persons wher you still can see the beautiful male behind the adorable woman- although i also love less war paint. they are perfect if they are switch like me."