I've noticed that a lot of people on here seem to enjoy stories involving cross dressing or prolonged bondage. This new story is a work in progress but it involves both so if that's not your thing you might not enjoy this story. This story is purely fiction.
My mom was a single parent who used to travel a lot for work. Sometimes she would get a babysitter on weekends when she had to leave town. And sometimes she would let me stay next door with our neighbors.
The mother was also a single parent and had two kids. One of them was a boy that was my age. His name was Ben. He also had a sister named Jenna. Ben and I were 14 at the time and Jenna was 17.
One weekend my mom went out of town and I went to stay next door for a couple of days. Their mom (I'll call her Ms. G) greeted me at the door and told me she had to go out that night. She said Jenna was going to be in charge and for me and Ben to listen to everything she said.
That night Jenna invited her friend Nicole over (also 17 at the time). They left us alone most of the night and hung out in Jenna's room. It was late and we were bored and started playing ball in the house. Ben missed my throw and the ball knocked over a priceless vase on the living room table.
Jenna heard the crash and screamed "Jake! Ben! What was that?" She came out and saw the vase shattered to pieces.
"Oh you're going to get it now! Wait until mom finds out. That vase was an antique. It was priceless. She's going to be so pissed."
"Please don't tell her" we begged. "Just tell her it was an accident. That you didn't see what happened."
"But it wasn't an accident. You were playing ball in the house. And you know mom doesn't allow that."
"Please Jenna" Ben begged her. "I don't want to be grounded for a month."
"Okay, okay. Let me think for a minute." She whispered something to her friend and Nicole said "ohhh good idea."
"Ok Nicole and I have discussed it. Here's what we're going to do. I'll take the blame for the broken vase."
"You will?" we both said.
"Yes but you have to do something for me."
"Okay" we said without even asking what it was.
"Go in Ben's room and wait for us."
We did what she said and waited. She came in carrying a bunch of her old clothes from when she was about 12.
"I want you to go into the bathroom and put these on."
"Are you serious?" we asked.
"Hey it's better than getting in trouble. And it's only going to be for one night."
We looked at each other and thought about it for a minute. We were hesitant but the girls eventually persuaded us to go along. Jenna explained to us how to put the trainer bra and pantyhose on and told us to go into the bathroom to change seperately.
Ben went first and came out dressed in the white blouse, skirt, and tan pantyhose. I could tell he was embarassed. I went in next and came out all dressed up to find the girls painting Ben's fingernails pink. They told me I was next.
Jenna painted my fingernails pink while Ben's dried and Nicole applied makeup to both of us. Then Jenna found these blonde wigs she had bought when she was younger and put them on us. We looked at each other and almost didn't recognize ourselves.
Then Jenna pulled out a camera and started snapping pictures of us. Ben started freaking out but Jenna just laughed and said we fell for their trap. Now if we wanted the pictures back we would have to do exactly as they said. And we still needed her to cover for us with their mom.
"What do you want us to do?" Ben asked.
"First I want you to clean my room" Jenna said. "But I don't want to hear you making a fuss about it so I think I'm going to gag both of you first."
We protested but her mind was made up. She took her white socks right off her feet and balled them up. Nicole got a roll of duct tape and Jenna told Ben to open his mouth. He refused but she quickly reminded him of the pictures. He opened his mouth and she crammed one sock in. He made some muffled protests but she crammed the other one in and Nicole gagged him some pieces of duct tape.
"Give me your socks" Jenna said to Nicole.
"I'm not wearing socks" she said. "I'm wearing footies."
"Well since I don't have anymore dirty socks lying around those will have to do."
Nicole kicked off her sparkly flat shoes. She had these tan nylon footies that barely went up to her ankles. She rolled both of them into one nylon ball and shoved it into my mouth. Then they gagged me with tape and told us to get to work.
We dusted, vacuumed, cleaned the windows, the dresser, made her bed, picked up her dirty clothes. We had to keep our gags on the entire time. We were standing a few feet apart but we could barely make a sound minus the odd muffled grunt or groan. The footies that were balled up in my mouth were damp and moist from Nicole's sweaty feet. They tasted so bitter and foul. It tasted so salty because of her foot sweat. I could tell by the sour look on Ben's face that Jenna's socks didn't taste any better.
After we were done cleaning they ordered us to go into Ben's room and lay on his bed. We laid on our stomachs and they told us to cross our hands behind our back. We did and they duct taped our hands behind our back. They didn't want to duct tape our legs and ruin our pantyhose so they got more pantyhose and used it to tie our ankles and knees together. It doesn't sound that effective but pantyhose are extremely difficult to untie or get free from.
Once we were all tied up and gagged the girls laughed and told us to have fun. I could see their full plan coming into focus. They tricked us into dressing up like girls just so they could tie us up, humiliate us, and make us their slaves for the night. We moaned into our gags as we struggled to get free. We quickly gave up when we realized it wasn't going to happen. The girls left us alone a while to watch TV in the living room. Then they came back up and decided to tickle us.
They started with our feet. I couldn't see too well because we were on our stomachs, but I'm sure Jenna was tickling her brother and Nicole was tickling me. The pantyhose they made us put on made their tickle torture even worse.
"Tickle, tickle, tickle" they taunted us. "Tickle, tickle, tickle. Tickle, tickle, tickle." It was endless and made their torture more degrading. I grunted into my gag, begging them to stop.
"What's wrong Jake?" Nicole asked me. "Oh wait you can't answer me with that gag on can you?" She then went on to taunt me about how long she had been wearing those footies and how her feet tend to sweat more when she wears nylon.
Ms. G returned later and was surprised to say the least when she found us bound, gagged, and dressed up like girls. Jenna shrugged it off and explained that she was busy doing something and we were playing ball in the house and broke her vase. She told her mom that she made us dress like girls and tied us up to punish us for breaking her vase.
"If that's true then they deserve to be tied up" Ms. G said. We were furious at Jenna for lying to us and not covering for us. But we couldn't even speak up thanks to our gags. Jenna asked if she could keep us tied up all night.
"I don't see why not" Ms. G said. "Just make sure to take their gags off so they can breathe."
Jenna took our gags off before bed. I breathed a huge sigh of relief when I got to spit out Nicole's salty nylon footies. "Here's the deal" Jenna said. "You guys are going to sleep with the gags off but if you make a peep the gags are going to go back on as fast as they came off. And if you refuse to do anything I say, everyone will see those pictures."
We spent the night tied up. In the morning they untied us but we were immediately gagged again with the worn socks and nylon footies. They made us sit gagged at the kitchen table while Jenna cooked us breakfast. Their mom was already out and about and Jenna was in charge again.
We were only allowed to take our gags off when the food was on the table. "You're not going to let us take these ridiculous clothes off?" we asked.
"Nope. I'm going to take advantage of the situation and use those pictures as blackmail material. If you don't do everything I say, I'll show those pictures to all your friends."
"How long are you planning to do this to us?"
"Every weekend." I almost cried when she said that.
"Hey we forgot to paint their toenails" Nicole said.
"What an oversight" Jenna said. "We'll have to paint those right after breakfast."
To be continued