"Josie comes to meet me in a hotel, and we finally give each other what we need"
Over the next week, every single morning that I went into class, the only thing I could think about all day was getting home, locking my bedroom door, and video-calling Josie. Each night, she would show off a different outfit...
I woke with a sore ass and throat. I had a cup of hot coffee to ease one of my symptoms from the night before. Only time could alleviate the other one, but until then it would be a delicious...
"My new big sister teaches me stuff a sissy really needs to know"
Giving myself to a t-girl is a new kind of thrill for me, and one that Mistress thinks every sissy should experience. Being with a shemale, she says, can help a sissy understand why hormones are so essential to reaching...
"The next morning"
San Diego, May 1971The story so far: Roger (aka “Sugar”), who is relatively new to gay life, went out on the town in drag for the first time with other cross dressers (or “He-Shes” as they were known locally) and...
"Stacey’s sissy education continues under the watchful direction of Miss Katie."
I felt the wetness as he spit on my asshole and the head of his cock. He slid the head back and forth, spitting several more times.“Please, Miss Katie,” I pleaded, “I have lube in my bag.”“Hmmm. I don’t think...
"Kyle's adventured continue"
Over the course of the following weeks, Tyler's love for this new mode of self-pleasure became stronger, and it made him bolder. At first, he waited until bedtime to indulge himself. Soon that wasn't enough, so now whenever the mood...
"Stacey meets Katie the next day as ordered. What does the woman who holds her chastity keys have planned?"
“So glad you remembered, sissy-girl,” Katie said. “Also, so glad to see you enjoying my panties from last night. Stand up, I want to inspect your work.” I took one last sniff and tossed her panties over to my bag....
"Stacey meets Katie in the bathroom after work as ordered, dressed as her “complete sissy self.” What comes next?"
Katie’s first orgasm had come quickly and was followed by a second within minutes. Her third orgasm took me nearly ten minutes of licking and sucking to bring her off. When she came the third time she pulled my face...
"I learn a little more about Joe, and how far he is willing to follow Daddy's instructions."
That first night, after I’d watched Josie swallow my cum, we kissed as s(he) stroked my still-hard cock, until I told her Katie might wonder where I was if she woke up to find me gone. Josie looked up at...
"The custodian catches Stacey in the men’s room at work. Where will this new relationship lead?"
She wasn’t super-tall for a woman, but she stood slightly better than 5’6” in her sneakers. When I saw her, it was always at work because she was the building’s custodian. She was either a very light-skinned black woman or...