Sissy Boy Chuck Becomes Just Sissy

byKrazy35©

Missy said "Ellen, this is Jessica's kid sister Sissy. Sissy this is my friend from school, Ellen"

I reached out and gave her my best "girl" handshake.

Ellen shook my hand, and said "Pleasure to meet you. Sissy, is it?"

"Yes. I'm Sissy and it's nice to meet you." I replied.

"Ellen doesn't know too many people here." Missy said. "She's pretty new so I thought I'd introduce her to you two."

We all sat around Jessica's room and talked and talked and talked, just like girls will do. I had to keep telling myself to stop staring at her gigantic breasts, I didn't want Ellen to think Sissy was gay.

After while the conversation got around to why Ellen had moved to our little town. Seems her step dad was convinced she was having sex with every guy in town. So, he sent her to live with her aunt and attend catholic school.

"The funny thing is." she said "I'm not doing anybody. As a matter of fact, I'm still a virgin."

"A body like that and still a virgin???" I thought.

The other girls must have thought the same thing because they both said "Really?" at the same time.

Ellen assured us it was true, then went on to tell us "I want to. But I'm afraid I'll get pregnant." We had a long talk about birth control. I felt a little out of place as we discussed how the boys don't really care about such things, as birth control and whether or not us girls have an orgasm.

Then Missy said "If you really want to lose you're cherry, I'll bet Sissy could hook you up with one of her men. She spends a lot of time playing with the boys, if you know what I mean."

"Really?" Ellen gushed "Could you Sissy? I'd really owe you big time."

"I don't know?" I said, thinking how the hell would I manage to fix her up and keep my secret from her and whoever this guy is.

"Sure she can." said Jessica. Then glaring at me said "Won't you Sissy?"

"Sure." I said "I'll do my best."

Jessica checked her watch and said "Oh shit. It's ten to 6. My Mom will be home any minute. She doesn't like us having a bunch of guests. You girls better go. But don't worry Ellen. Sissy will hook you up with a great guy. Won't you Sissy?"

"Yeah." I said "A great guy."

Ellen and Missy got up to leave. Ellen hugged me close, pressing her massive jugs into my fake breasts then kissed me right on the lips. My cock strained against the tape but it held and kept me from getting hard and ruining my little secret.

"Thank you Sissy." Ellen said "I'll owe you forever."

Then her and Missy headed for the door. I headed for my room to get cleaned up and changed before Mom's arrival.

Samantha stopped me, but waited for the door downstairs to close before speaking. As soon as she heard the click she turned to me and said "I'm very happy, Sissy. You passed your first test. You convinced a complete stranger that you are indeed a girl."

"I did. Didn't I?" I said grinning from ear to ear.

"That means we can move on." Samantha said "Schools out this Thursday. Monday we start phase two and a whole new series of tests for pretty little Sissy."

"Phase two?" I questioned "What's phase two, and what tests?"

"Monday." Samantha laughed "You'll start finding out on Monday. And you better find a great guy for Ellen, or I may get angry." Then stepped back into her room and closed the door.

I stood in the hallway dumbfounded trying to think of what more could she want of me until I heard my mother opening the door. I ran into my room and started my cleanup thinking I guess I'll have to wait until Monday.

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byKrazy35© 10 comments/ 149259 views/ 12 favorites

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by Anonymous

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by Anonymous03/09/14

Who's Samantha?

You didn't say who she was anywhere in the story.

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