Sissy Stepbrother

Chapter 2

Madison knew that her sixth can was enough yet she still opened another.

He was also getting hazy and was sure that all the girls had tied him up somewhere? So when he saw them walking away all he did was pass out.

***

Waking up in the morning he found he was tied up inside the girls closet and the brunette girl opened it. "Hey, Maddie... Sorry about that, the other girls tied you up when you started getting... Experimental?"

Tom took a while to remember yesterday and only just remembered his Madison voice, to find a ball gag was in his mouth, "whhh eerrr ohhh uh?"

"Oh, c'mon." She easily picked him up and carried him over on to the bed.

Still in the t-shirt, nylon underwear, white stockings, and he saw his microskirt and heels in a pile with the other girls. The four other girls were doing eachothers makeup and as he lay there, still tied up, the brunette began putting a new layer of makeup on and painting his nails a shiny black.

While she did this she recapped last night and introduced everyone, "I'm Piper... And the blonde doing you're stepsister's makeup is my cousin Harriet. The black haired girl is Nicole and the one doing her makeup, Rachel..." Piper spoke to her like an old friend and removed her ball gag to put on some lipstick and do the foundation around his mouth. But promptly returned it after. "Last night we all drank... A lot... Jesus, I've never been so hungover! Well after a while we started to do some dares, which ended when you excepted the dare to go on a double date with Michelle... Which starts in... Two hours." She then skipped to the closet and got some of the bags Michelle had bought.

Piper untied her and let her pick out some clothes, Madison grabbed a lacy pair of black lingerie with matching stockings. She was very happy to see the long sleeved, cropped top she happily grabbed it and some skinny jeans. In one of the bags had a dozen shoe boxes, he found some pink and white trainers so strutting into the ensuite bathroom and changed.

Madison was too hungover to care when Piper asked if she wanted her to shave her legs as they had a few short hairs, but didn't wait for answer and shaved all his body hair off.

Madison's double date with Michelle would start in half an hour and as Michelle met her outside they got in a taxi and talked very vaguely. "I'm sorry about this, I know I said this thing would only be yesterday but... And the girls insisted so..."

"That's fine." She muttered, leaning against the window to calm her head.

"Great!" Michelle gave her a hug and in ten minutes they reached a café, bigger than they one they went to yesterday.

Madison struggled to walk in the trainers and the pair waited outside for their dates. "Who are we going to be on this date with?" Tom asked, after checking no one was in hearing range.

"Probably these two guys from the basketball team: Harry and David." Michelle answered looking the boy up and down.

"Cool... Can't I just run away!" He asked.

"I dunno know?" Michelle thought, "... But I do have those photos of you?"

Tom gulped and pulled his top out from the crack under his breasts, he realised he was sweating and asked if he could use the bathroom. Michelle asked him a follow up question, "which, boy's or girls'?"

Tom frowned slightly, he couldn't just walk into the boys bathroom, "I'll use the girls, I was always curious about that place and what girls do when they go there together... I hope it's make out!" He then popped his hip and strut into the girls' bathroom. Michelle giggled at the memory of how boyish he'd been just two days ago.

***

Toms first thought of the girls'bathroom was that there was more pee on the seats than he'd like. But as he could stand it didn't bother him, locking a stall he realised he couldn't use the toilet as he was wearing the pad! So he decided he would have to either sit on it and see what happens, or he could use the ointment (that he kept between his breasts now) and remove the pad. When he heard the door open and two about eighteen year old girls walked in, "I can't believe you dragged me into this!" The first one told the second.

To which the second chuckled, "because what... You still wanna be with me." Her voice started off in s joking tone which soon became lustful and soft.

"W-Well... Yes, I do..."

"Say what you used to say."

The first's voice went quite and seductive, "no more talking." And with that they joined together and started making out, which was when he sneezed, causing the two to quickly act like they did t even know eachother, cleaning themselves using the mirror. Tom walked between the blushing girls and washed his hands. Drying them he listened for a short while where he clearly heard them return to making out.

He skipped over to Michelle, "guess what just happened!" She told her about the girls.

Michelle simply replied, "that's not what always happens!"

***

Madison noticed that she was shaking from fear, her first date, he had hoped it would've been with a hot girl (like Nicole, who was in his opinion the hottest girls he'd ever seen (not including Lillian)). He also hoped he would be 'Tom', in a shirt and pants, but as he stood there in female lingerie (and stockings) and skinny jeans she changed her mind. She knew that she was much more comfortable in the tight clothes, Tom had had a very small frame and almost no muscles so her curves were free to be flaunted.

Madison was using a little mirror to check her makeup when the boys arrived, but not who Michelle said, it was two people he knew very well, the boys who had called him Sissy and looked up his skirt yesterday. The two black haired boys with big build's shoved eachother to try and get Tom.

Eventually the one who was wearing a hoodie and jeans had won and escorted her to a seat and sat next to her. His gaze continuously went to her rack and he put his hand on her knee while the other grabbed the menu. She had to bend over him to read it and his hand moved from her knee to her exposed skin on his back. Madison gave him a warning look and laughed before taking the hand of and stroking a few strands of her hair.

Tom looked across the table and saw the exact same thing was happening. The boys then sighed, "I'm Corey." Said the one next to Michelle.

"Michelle." She muttered.

"And I'm Adrian." The one currently touching Tom's arm introduced.

"I-I'm Madison." He stuttered back.