The Feminized Cuckold - Michael to Michelle

I was fortunate in my last relationship with a couple (Carol and her sissy paula) to walk into a situation where the roles were clearly established.  In a nutshell, Carol wore the pants and paula wore the panties.  Paula was in panties 24/7/365 and was expected to dress like a woman when at home and even sometimes in public.  Carol taking on an Alpha lover (Me) was in her words "the next step in the maturation of their lifestyle."

In my previous relationship, the feminization of the cuckold was a collaborative effort between me and Pam.  Pam's husband Michael had submissive tendencies and had admitted to her that he had often fantasized about wearing her panties.  This admission had taken place before we even met but after few months together she shared it with me.  We decided to introduce it into the relationship and see where it went.

It took a couple of weeks to decide how we would introduce the idea.  Michael's sharing his fantasy with Pam had been a secret she'd kept up until now.  I had a good thing going and didn't want this breach of confidence to ruin in, much less affect their marriage.  We decided that it would be Pam who broached the subject with Michael, telling him she'd been thinking about his admission and that it excited her.  She would tell him that she would like to explore it in the context of the three of us.

Not surprisingly, Michael was not just hesitant but actually frightened about my finding out but, after some coaxing from Pam, agreed to start wearing panties under his male clothing.  It would be their secret she told him.  Though Pam was deceptive, it set the stage for introducing me to the "secret" I already knew.  Michael wore panties every day, even to work, and both Pam and I were patient to let him get comfortable with this small step.  All the while, Michael became more submissive to both Pam and me whenever I was around. 

The big moment didn't come until more than a month later when Pam got Michael to agree to let me in on the secret.  One Friday evening shortly after I arrived at their place, Pam told me that she and Michael had something to share with me.  "It's a surprise of sorts" she said and asked that we make our way to the living room where Michael would serve us some drinks.

After bringing in the drinks Pam had Michael stand before us.  She got up, stood behind him and began to undo the belt on his shorts.  She then undid the front of his shorts, told him to put his hands on his head and tugged his shorts so they fell to the floor.  Michael stood there in a pair of Pam's panties.  They were white with lace on them.  Michael was red with shame and avoided eye contact with me.

"We wanted to surprise you.  Michael's always wanted to wear my panties" Pam said.  "We thought you should know right Michael?"

"Yes Pam" Michael answered.

"Well I'm happy you did" I said.  I looked at Michael's crotch and I could tell he felt my stare. His cock was getting a bit bigger.  Maybe enjoying the attention or the embarrassment I surmised.  Instinctively, I put my hand on his little bulge.

"The look cute on you Michael" I said and after taking my hand of his panties added "And it's nice to know there's only one real man in this house now."

Michael stood there obediently until Pam told him to pull his shorts up and join us for drink.

Evetually, Michael became Michelle, an obedient feminized cuckold.

Karl