Chris was your average teenage boy. He liked girls, sports, and hanging out with his buddies. Chris was a bit short, around 5'6", and weighed no more than 130 lbs. He had a nice, flat stomach and lanky arms from soccer, with longer brown hair and nothing but peach fuzz on his face.
Despite younger features and a hairless body, Chris had developed nice legs and a bubble butt from all the soccer. His cock was a little below average, only about 5 inches long. Being an only child and a hormonally raging teenage boy, he loved porn. One night, he stumbled across some shemale porn, and man did it turn him on.
He was hooked, the only thing that turned him on now was these beautiful women with cocks bigger than his. His attractions changed. He became obsessed with bras and panties. He loved the thought of putting on makeup, doing his hair and nails, and being a full fledged woman. "Its not fair," he thought, "why can't I just be like those girls in the videos." Across the street from Chris lived his friend Jason, two years younger than he.
Jason had an older sister named Danielle, and lived with their divorced mother Christine. Danielle, two years older than Chris, was a popular cheerleader at the local high school and had great tits, a 36c, and an ass that would make any boy hard. With her long, dirty blonde hair, she constantly paraded around in nothing more than short shorts and a sports bra. But it was clear she got her looks from her mother. Christine, no older than 40, was a matured goddess.
Beautiful brunette hair, a wonderful set of 36d breasts, and killer abs. Her and Danielle were known to go on long jogs through the neighborhood, much to the joy of its male inhabitants. Jason was often teased about his hot mother and sister. Chris, who attended the local catholic school, devised a plan. He had gotten done early for a Christmas break, and was going to break into his neighbors house to see what Christine and Danielle had in their lingerie drawers.
He knew Christine always forgot to lock their back door, so around noon he entered the house. First, he went to Christine's room. It was exactly what he had imagined. His heart racing, he opened the drawers to find delicately laced bras, panties and stockings.
He also found a few corsets and garters, and to his delite, he found Christine's 10 inch, thick, veiny purple dildo.
After carefully selecting an outfit, he put on a laced black bra with pink bows, a black laced thong, complete with a matching garter, stockings, and black high heels. He then went into the bathroom with a brunette wig he had found at home, and applied some of Christine's makeup.
Black eyeliner, foundation, all complete with bright pink lipstick. He then put some tissue paper in the bra to fill out his figure.
"Damn. I look hot." He returned to the bedroom and pulled out Christine's purple dildo. It was time for him to become a full woman, a full fledged sissy boy. He laid on the bed, and spit on his fingers, as he prepared his tight hole for what was about to happen. Precum oozing from his semi-hard cock, he slowly entered one finger into his little hole.
It felt so good, so right. Two fingers, three. He was ready for the dildo. He slowly let the purple, veiny toy penetrate him. He could feel his hole stretching, finally welcoming in the object. He started to thrust harder, his hole welcoming in more of the dildo. He started to stroke his cock, and the pleasure was amazing. The deeper the dildo went, the harder he stroked. It was sheer ectasy. He was about to cum, and felt warm loads of his own juice shooting all over his stomach.
As he laid there catching his breathe, all Chris could think about was how he wanted more. "Im going to go to Danielle's room. Its time for me to be a cheerleading slut." He put the lingerie back in the drawer, and took the dildo to Danielle's room. Her panty drawer was full of Victoria's secret PINK thongs and g-strings.
He found a nice matching neon yellow g-string with a bra top. The way his ass looked in the g-string turned him on so much. He found a pink bow to match his lipstick, placed it in his hair. He found some cheerleading sneakers and some pom-poms lying around and looked in the mirror.
"Tranny sluts, we want it in the butt. Tranny sluts, come and lick our nuts. GOOO TRANNYS!" Chris cheered in the most feminine voice he could muster. He took the dildo and put it on Danielle's bed, facing the mirror. His hole was ready this time. He moved the g-string over, and sat on the dildo. He was finally riding cock like a real woman, a real sissy boy slut.
It felt so good in his ass. Now he was throbbing harder and harder on the dildo. He bent forward on all fours, and took all 10 inches of the dildo, holding it deep in him.
All of a sudden the door to the room opened, and he came face to face with Danielle. "Oh my god&hellip.Mom come here now." She yelled. Chris could hear his friends mother running up the stairs. Christine and Danielle stood in the doorway staring at him for a moment. Then they both burst out in laughter.
"Chris what the hell are you doing?," asked Christine.
As they walked towards him, Chris could only muster a simple response. "I wanted to feel like a woman. I don't know it turns me on. " They sat down on the bed next to him "Well," Danielle replied, "you don't look bad as a girl.
Pretty cute actually." "Yea and I'm impressed you could take this entire thing.," added Christine, now noticing Chris had her dildo stuffed fully in his ass.
"Your lucky Jason is at basketball now. Tell you what, Danielle and I are having a little get together with some friends this weekend, a Christmas Party. If you come over this Saturday and be our little sissy boy waitress, we wont tell Jason, plus he'll be away all weekend at a tournament.
Now Danielle, what do we name Chris?" As Christine finished talking, she grabbed the dildo still stuffed in Chris's ass and started fucking him. "I don't know mom, how about Chloe. Yea Chloe the sissy boy." Danielle now started stroking Chris's cock. "C'mon now Chloe, get that sissy clit nice and hard." Chris couldn't take it, he was so aroused. He shot his load all over Danielle's hand.
They both burst out laughing. "Oh wow, look at that little bit of cum. The girls will have a fun time with this mom." Said Danielle. "Well now, the party starts at 8 o clock, be here at 4 on Saturday, don't be late.
You don't want us to tell Jason now do you? And take my panties off, you sissy slut.
See you Saturday." Chris stripped naked, causing laughter from both Danielle and Christine, found his clothes and left. He was so confused, so embarrassed. But he loved it, and couldn't wait for Saturday to see what they had planned for him.