Oral Servicing

Debra got up and went into her bag and brought out a pair of black pumps, about 3" high heels, and a pair of nylons. Nude, thigh highs. "Put these on," she told me. I must have had a dumbfounded look on my face. "Don't give me that look. You're a Sissy. No normal real man would do what you do for me. Wearing diapers and panties. Licking my ass. You don't fuck. No tits for you. Jacking-off in front of me. Small dick. Sucking on my panties and eating your own cum. How does it feel to be a Pussyboy, Sissy to a fat, hairy lesbian cunt? Put them on!"

I could only put my head down and blush listening to her piercing, humiliating, but true words. I sat on the edge of the bed and slowly began to roll the silky stockings up my legs. The elastic bands held the stockings tight around my thighs. She laid her black heeled pumps down in front of me and pointed to them. I slipped my feet into them.

"Stand up," she said. I did so but felt a little wobbly standing in the heels. "You'll get used to wearing them and walking in them," she stated firmly. "Put your arms out in front of you." Again, I complied. She brought a pink, lacey bra from her bag and slipped it over my outstretched arms and went around behind me to clasp it in back. She took her phone and snapped several pictures of me! "This is my insurance and for my amusement," she told me. She then took my phone and copied my contact list! "Don't worry, I'm sure I won't ever need to use this," she attempted to reassure me. She put her bra and top on but remained naked from the waist down.

My cock was stiff in my panties. They tented, even against the pad, pushing my panties out in front. "See how excited you are?," Debra queried. "Only a Sissy would get so hard dressing up so girly."

I hung my head and tried to cover myself with my hands. Debra went to her bag again taking out a jar of Vaseline. She said, "Pull your panties down, and take out your pad." and handed me the jar. I took the jar from her, took the pad out, and my panties fell around my ankles. I felt foolish and ashamed. Debra took a few more pics of me and then took a seat in a chair facing me. She spread her legs wide, but her top covered her pussy, but I knew she was naked underneath. I had hoped Debra might touch me, but she nonchalantly just said, "Use the Vaseline and start your masturbating. Sissies just use two fingers. Your thumb and index finger. Start wearing panties and pantyhose under your clothes at home and work. I want you to do two-finger masturbating daily in front of a mirror with your panties pulled down. Just before you spurt, I want you to let go of your penis, pull your panties up and cum in them. Use my panties and smell them while you jack-off. You're my Sissy now."

Debra went to her bag again. She took out a dildo. It must have been 8" of thick fleshy rubber with big balls on the end. She sat down and slid the dildo under her top hanging down and I watched it disappearing between her legs. I was getting really hot and flustered. Debra knew it. She asked, "Do you wish this was you?," as the dildo slid in and out of her pussy. She was fucking herself, holding the rubber phallus by the balls, nearly taking it all, while she watched me masturbate wearing sissy clothes.

"Pull up your panties and cum in them," she shouted at me. I did. She did too.

This was the start of something I never expected.