num_pages: 106
description: Shy wimpy little Bradley Aimes meets the sensually adventurous Caroline during his freshman year in college. He fantasizes about making love to the beautiful thirty-something woman who picks him up by telling him he has beautiful blonde hair. When she takes him back to her condo Caroline tells Bradley she wants to see what he would look like in her bra and heels. He admits he used to sneak into his mothers closet and wear her dresses and bras heels and panties. So Caroline begins dressing Bradley telling him he is an effeminate sissyboi and forcing him to face the gurl buried deep inside his psyche. It begins innocently but when Bradley asks to spend time with his seductive girlfriend simply as his male persona Caroline refuses. If he wants to be with her if he wants her to satisfy his young urgent sexual needs Caroline will only comply if Bradley wears heels and bra. After the first encounters his guilt and humiliation overcome Bradley and he breaks off his relationship with Caroline but she plays voice recordings of him admitting he is a sissyboi who enjoys dressing as a girl. When she threatens to send the recordings to his mother their relationship takes on another turn altogether Excerpt:Carolines sissyboi Bradley wants her to stroke my stiff little peenie beneath my skirt Shit! She recorded me!When you were shaving your legs I took down mommys number from your cell phone baby she said. Now you can either come into the salon with me or Ill send this off to mommy.I cannot believe youre doing this to me! I was enraged but what could I do? My hands were sweating and my heart was racing when we entered the lobby of The Mane Event. She leaned down and kissed me softly. Gloria is waiting for us! Lets get you styled! Caroline put her arm around me and led me to an office in the back. She closed the door then took out a black bra from her purse. It was much smaller than the other bras Id worn barely creating cups at all. You need to wear this for me today she said.Caroline! Were in public! You cant be serious!Im serious about having a frank discussion with mommy she said. Put it on baby.I felt like I wanted to cry as I took the bra from her red-nailed fingers and put it on beneath my red silk shirt. I felt like such a sissy!You look great she smiled then took my hand opened the office door and led me to a booth in the rear. A voluptuous redhead smiled as we approached.Gloria this is my special friend I told you about. Baby this is Gloria my best stylist.Gloria motioned for me to sit in the chair and I did cringing at the thought of what she was about to do to me. So youre Carolines new friend she said running her fingers through my hair. She said you were a pretty thing and she wasnt exaggerating. If things dont work out with her you need to give me a call sweetie. Youre a doll!Please dont give me an outrageous cut I pleaded as Gloria studied my hair dropping it around my cheeks then pulling it back. Im going to make you gorgeous dont you worry Gloria replied. I have strict orders from the boss.The boss?Yes the owner Caroline.Caroline? She owns the salon?I can see there are a lot of things Caroline hasnt told you Gloria giggled. Well all in due time sweetie.
language: English
title: The Reluctant sissyboi, Becoming Caroline's Gurl
publisher: None