Sissy in Chastity

Read part one of this sissy story if you haven’t already. Now let’s proceed because we’re getting to the best part! I explained to sissy that if she wants to keep her girlfriend, she’ll have to make some adjustments. Obviously, her clit-stick is of no use. Hence why it’s in a chastity device! So, I had a surprise for sissy… She had NO IDEA what was going to happen next.

The front door rang and I had her go open it… Her girlfriend was standing there along with a man.

It wasn’t just any man, but a close friend of the girlfriend. He’s one of those masculine types. The kind that frequents the gym and just exudes masculinity. Oh, and he has a thick 8-inch cock. Completely the opposite of the sissy! I knew he would be perfect for what I wanted to do next.

Sissy had no idea that I was talking to her GF behind her back. She told me all the ways sissy would try to fuck her but it always led to frustration. The girlfriend was so deeply unsatisfied in the bedroom. Honestly, it didn’t take much to convince her that she should start having sex with other people. Of course, we all know how men are, and it doesn’t take much convincing for them to fool around.

So, with that being said, things quickly turned sexual. The girlfriend had never done something like this before. This was something totally new for everyone involved. But so exciting nonetheless!

I commanded sissy to get on her knees at the end of the bed.

She was in full view of her girlfriend and the Stud, who was slipping his tongue into her mouth. His hands traveled across her body and underneath her skirt. I watched sissy, seeing her eyes begin to water. So I walked over to her and whispered in her ear “it’s okay, this is for the best… You’re making your girlfriend so happy right now.”

Soon the Stud had his thick cock out and ready to stick it in. I could see the pleasure in the GF’s eyes as soon as he began stretching her pussy. It seemed intense by the moans she would make and the rough pumping he would do. I got down on my knees beside the sissy. Even though tears were in her eyes, you could still tell she was turned on. She was biting her lip, it almost looked as if she was hypnotized. Her eyes were locked on that fat cock drilling his girlfriend. Doing all the things to her that little sissy could NEVER do.

As the man finished inside that hot pussy I had the sissy clean up his girlfriend between her legs.

This was all so new for both involved but she quickly took charge of her feminized “boyfriend!” Making that bitch clean every drop of cum from her freshly fucked pussy. I could tell they both loved it. So I think this is a new chapter for the both of them. I love to help relationships flourish!

Get the audio here.

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