My friend (much older than I am and married –with children) visited me from Florida, and over a glass of wine we talked about some changes in her relationship with her cuckold husband.
They have always had an open relationship; she fucks anyone she wants to except him (he’s a very joyful and chaste cuckold), and often brings them home for him to watch or just play clean up. Sometimes they videotape the event (always with consent) so they can relive her getting pounded by a large cock, and him playing cocksucker to her stud. He’s never taken one up the man pussy, but he does love to take a large, glorious cock between his lips, and get it ready for her hot pussy or lick it clean after a hot guy fucks his slut wife. He’s always played cocksucking husband to her slut wife, and believe me — she is a slut! LOL!
They’ve been pretty happy with their arrangement, but it looks like her husband was keeping a secret from her. She came home early from work a few days ago and caught her husband crossdressing!
She admitted to me that, even with their current arrangement, she was shocked. He had never shown any interest or tendency to wear female clothing, and had never expressed an interest in sissification and cross dressing. Actually, he was quite a manly-man, except when he was on his knees slobbering over a big cock for her pleasure. Even then, she told me, he wasn’t sissyish. He sucked with the gusto and manliness she had always seen in him.
I know her husband very well. I honestly had no idea that he enjoyed the thrill of panties and lace. He’s a pretty large guy, and even though he is quite handsome, I cannot picture him in a thong and nightie, attempting to put a pair of her size 9 shoes on his much larger feet. She said the entire scene was quite funny, and even though she really has no problem with his crossdressing, it’s the fact that she didn’t “see” it coming, and I, given my “occupation”, did not see it either. Granted, they have been living in Florida for a while, so this may be a new development. I do intend to find out. 
She told me that she plans to explore this, and asked me for advice on his sissy transformation. Apparently they plan to include this in their cuckolding adventures, but she is really lost on where to begin. I could tell she was disappointed that he didn’t share his femme fantasies with her sooner, but as she left, armed with my advice, I could also tell she was excited. I’m looking forward to hearing about *more* of their wild ways — the stories have always been interesting, but I bet they get even better now! ~giggle~
Empress Samantha
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2 responses so far ↓
1 sissy bobbie // Aug 22, 2008 at 2:11 pm
Empress Samantha,
Reading about Your friend and her sissy husband made me think about how wonderful it would be to be Your cuckolded sissy. It would be such a high honor to be placed in my pink cock cage by one of Your studs before fluffing him in preparation to enter Your Divine Palace of Pleasure that is forbidden to craving sissies like me. i would do everything exactly the way You told me too and rejoice in the fact that You were getting the pleasure deserving of Your beauty and perfection. i get so excited by the thought of all this Empress because You are the world’s most wonderful being.
Submissively Yours,
– sissy bobbie
2 BlondeAngela // Aug 25, 2008 at 4:00 am
Dressing as a lady is wonderful for him, as he gradually developes to becoming a her, a femme ladyboy.
As he begins to dress and look more as a lady, and gets better at female impersonation,and consider himself more as a lady, he will only get better at pleasing handsome masculine men.
His wife/mistress might consider having him go on female hormones and start to transtion to being a lady.
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