A Sissy's Mother Has a Plan -- Part 1

Billy had been seated at his mother's vanity for the past two hours while she did his hair and his make-up, ensuring that Billy looked like a sweet and sexy young lady.  Heavy gold earrings hung from his recently pierced ears.  His eyebrows had been plucked into gentle arches.  His recent strict dieting had succeeded in making him very skinny and delicate looking.

He wore nothing but a darling little bra and panty outfit in the softest pink. Mother had padded the bra cups to give the appearance that Billy had little breasts.  The bra was festooned with a a large bow and long ribbon. It was a very seductive outfit.

The doorbell rang and mother exclaimed, "Oh good!  He's here!  Now don't forget ANYTHING I told you about what you are going to do tonight. Do you understand?"

Billy turned on the little vanity stool on which he had been perched.  He looked at his mother who was wearing the identical pink bra and panty set.  His anxiety was mounting by the minute.  He pleaded, "But mother, do I really have to do this? Please don't make me. Please!"

Mother was not going to tolerate even a hint of insubordination.  She needed Billy's complete and enthusiastic cooperation.  Mother stormed over to where Billy sat on the vanity stool and pointed her long, manicured finger directly in his face.  "Do NOT let me down tonight or you will regret it! I think we should both consider ourselves very fortunate that Mr. Robbins has taken such a keen interest in us.  With just a little more effort, I think he might ask me to marry him and then all our problems will be solved.  We are completely broke and things have been very hard for me ever since your lousy father ran out on us."

"But mother, please!" Billy said as tears welled up in his eyes.  "I've been good.  I let you dress me up like a girl and go out with both of you on your dates.  I even let Mr. Robbins touch me and hug me. But this is completely different. Dressed like this he is going to expect only one thing.  Sex!"

"No shit, genius," Mother harshly replied.

"And besides," Billy said through his tears. "Mr. Robbins is a bad man.  Everyone knows he's part of the mob."

That comment enraged Mother.  She slapped her sissy son hard across the face. "You take that back! Mr. Robbins is rich because of his perfectly legimate waste disposal business. Now wipe those tears away and pull yourself together." 

Mother went downstairs and let Mr. Robbins.  When she led him into the bedroom, he saw that both Mother and her sissy son were dressed in the exact same sexy outfit.  A big smile crossed his face.  "Well," Mr. Robbins said. "This is going to be an interesting evening.  Let's see what this sissy can do.  Get over here and get on your knees, sissy."

Sissy Billy did as he was ordered.  He unzipped Mr. Robbins pants and outsprang an enormous cock.  "Don't just stare at it, sissy!  Suck it!  NOW!"

Reluctantly, Billy did what Mr. Robbins wanted.  He closed his eyes and put the stiffening dick in his mouth.  Mr. Robbins firmly held the back of Sissy Billy's head as he began pumping in and out of Billy's virgin mouth.