Tricked By Friend's Sister

Postby Unknown » Sat Sep 02, 2017 9:43 pm

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
Last edited by Unknown on Sat Sep 16, 2017 5:40 pm, edited 1 time in total.

Re: Tricked By Friend's Sister

Postby barefoot99 » Fri Sep 15, 2017 12:48 pm

nice more plz. i wish i was part off this fun
BAREFOOT AND CUFFED, THAT'S THE ONLY WAY TO GO!!!!!!!!!!!!!!

Re: Tricked By Friend's Sister

Postby CHillDice » Fri Sep 15, 2017 4:25 pm

Nice story, please continue!!
You got to ro ooo ooll me, and call me THE TUMBLING DICE!!!

Re: Tricked By Friend's Sister

Postby Unknown » Mon Sep 25, 2017 12:11 pm

After breakfast those socks and nylon footies were stuffed back in our mouths and we were gagged with tape. They made us take the pantyhose off and sit down so they could get to our toes. They painted them pink to match our fingernails. When they dried we put the pantyhose back on.

We mumbled into our gags to ask them what now.
"Hey you guys don't sound too excited. You should probably get used to this seeing as how we'll be doing it more often." That remark made us mumble and grunt into our gags even more.

They took us to Ben's room where they taped our hands and used pantyhose to tie our knees and ankles again. "The pantyhose and duct tape are only temporary. Nicole and I are going to get some rope for next weekend."

We thought they were going to tickle us again. But instead they pulled up chairs on both sides of the bed. They took their shoes off and rest their bare feet in our faces. I can't say I ever saw a foot that close up before. And I never really wanted to. But it wasn't like we had a choice.

Jenna wiggled her toes in my face to taunt me while I heard Nicole taunting Ben. Jenna was a pretty girl and she kept clean but her feet always smelled no matter what. That made her socks the worst for gagging material.

"Trick or treat smell my feet" Jenna taunted me. I mumbled a few curses into my gag and tried to move my head but she kept moving her feet closer and closer. We spent the rest of the day tied up, gagged, being tickled and forced to smell their feet and inside of their shoes.

The next day I was supposed to go home but they had their mom call my mom and ask if I could stay for one more night. They let us eat breakfast and they changed our gags. They used some of Jenna's dirty socks from the laundry basket. Then they made us change our clothes. We were given new bras and underwear, clean skirts and blouses, and black pantyhose.

We were still getting used to the new clothes so Jenna had to explain to us how to put the pantyhose on. It was the most embarasing experience of my life up to that point. Our gags made it even more degrading because we couldn't speak up or defend ourselves. We had to do everything they said. And Jenna seemed to agree.
"Is there anything more humiliating than make a guy dress up as a girl?" she asked.
"I can't think of anything else" Nicole said.

We spent the rest of the day with our hands taped and our ankles tied with pantyhose. They made us lie on the living room floor and smell their feet while they watched TV. Even their mom took a turn to punish us for destroying her vase.

"Don't think this is over" Jenna told us at the end of the night. "You have next weekend to look forward to."

Re: Tricked By Friend's Sister

Postby Unknown » Mon Oct 02, 2017 11:11 am

Ms. G called my mom and asked if I could stay over next weekend. I walked over with Ben on Friday after school. Jenna and her friend Nicole said they were going to get some real ropes to tie us and they had gone with Ms. G to pick some up from the hardware store. It was cotton or nylon. Whatever it was it was soft but it still kept us from escaping.

They painted our nails first. They used pink nail polish like the last time. Then they showed us our new clothes. Trainer bras that used to belong to Jenna, white panties, skirts, blouses, and pantyhose. Mine were black and Ben's were brown.

"Do we really have to wear these?" we asked them. "Didn't you punish us enough last week?"
"Mom doesn't seem to think so since you broke a priceless vase. And it's really funny seeing my brother and his friend dressed up like girls. So you'll do as we say from now on. I have a feeling Jake will be spending every weekend here from now on."

We dressed and they tie us up in Ben's room. Our hands were tied in front and or ankles were tied. They used more rope to join our hands and feet together in a reverse hogtie. For our gags Jenna used her worn socks on her brother. Nicole gagged me with her tan nylon footies. They were like those nylon socks they give in shoe stores. They barely went up to her ankles. They took pieces of tape and put it over our lips.

They tickled our feet and taunted us. "Tickle, tickle, tickle. Tickle, tickle, tickle. Tickle, tickle, tickle." We mumbled and grunted into our gags. I hated being tickled but the hose made it even worse. They weren't like socks where they kind of protected your feet. We could feel their fingers scratching our soles and the nylon material rubbing against our feet.

They tickled us from head to toe for two hours. They gave us a little break afterwards and untied us so we could use the bathroom before bed. "You're going to sleep with your gags on tonight" Jenna said.
"MMMPH!"
"Silence. Your gags are there for a reason you know? You'll just have to deal with the taste our socks until the morning."

They tied us up again. It was very hard to sleep with the gags on and the nasty taste of their socks and nylon footies. But we fell asleep after a few hours of struggling and mmphing.

The next day they let us eat breakfast and shower, use the bathroom. Then they decided it was time to play dress up. They had us try on various dresses and outfits that used to fit Jenna when she was our age. It was so humiliating. It was even more humiliating that they had changed our gags so we couldn't even speak up or protest. A pair of worn socks was used on Ben and a pair of their moms pantyhose was stuffed in my mouth before they gagged us with duct tape.

They made us try on all different kinds of stockings, tights, and pantyhose with her clothing. They even made us try on some old Halloween costumes. I tried on a white nurse costume with white stockings and a pink princess costume with pink tights. Ben had to try on a French maid outfit with black fishnets and an orange inmate costume that was just an orange dress with a fake prison number on it, and a pair of bright orange tights that looked ridiculous. They were really having a laugh at our expense.

"I can't wait to do this every weekend" Jenna said.
"Summer is a few months away" Nicole said. "We could do this all summer."
We screamed through our gags at her idea. But they both seemed to like the thought.
"I'll run it by my mom and see what she thinks."

I did not want to spend the entire summer tied up and dressed as a freaking girl. No way. But Jenna and Nicole were in control thanks to those pictures they were using to blackmail us. And their mom had no interest in helping us after we destroyed her vase. We spent the weekend playing dress up, being tickled, and forced to smell their stinky shoes.

I came over every weekend after. That's how it went for two months. Until my mom got curious and decided to come over one weekend...

Re: Tricked By Friend's Sister

Postby PiggyBoy » Mon Oct 02, 2017 2:13 pm

Keep it up! Always love your stories!
PM me if you ever want to hear stories or ask me questions! Oink oink! :8)

Re: Tricked By Friend's Sister

Postby Brashiel » Wed Oct 04, 2017 4:39 pm

Always love your stories. This one has been great so far.

Re: Tricked By Friend's Sister

Postby Unknown » Mon Oct 16, 2017 1:11 am

My mom walked in on Ben and me tied up on the bed and gagged with duct tape. We had skirts and blouses and pantyhose on. Our toes and fingers were painted pink and the girls had even covered us in makeup.
"So that's what you've been up to every weekend huh Jake?"
I mmmphed and begged her to untie us.
Ms. G explained to my mom about the vase and how Jenna and her friend came up with this as a punishment. My mom apologized and offered to pay for the vase but it could not be replaced since it was an heirloom.

Ms. G then suggested that our punishment should continue for the entire summer. My mom didn't seem too crazy about the idea of her son being tied up at the neighbors house all summer. But she thought about it.
"Well they do need to be punished for what they did. And this really isn't hurting them or anyone else. And Jake has been on his best behavior lately. Maybe this has something to do with it."
We mmmphed and shook our heads no.
"Okay but first a few rules. No more of this wearing Ben's sisters clothes. We'll put some money together and get some clothes that fit them right. And I'd like Ben and Jake to stay over at my house a few nights now and then so I can keep an eye on Jake. And I'd like to be able to come over here anytime I want to see him."
Ms. G agreed and just like that it was decided. We had no say. We were gagged and helpless. We couldn't protest or speak up. Jenna and Nicole were so happy when they heard the news.
"This is going to be the best summer ever" she taunted us.

When they untied us so we could eat we begged them to let us enjoy the summer.
"You can't do this to us" I said. "It's not fair. We're going to miss the whole summer."
"Yeah please don't" Ben said. "We learned our lesson. We're sorry. Please you can't do this. You can't tie us up all summer."
"Yes we can" Jenna said. "Our mom and Jake's mom agree you deserve to be punished. And if they change their minds I'll just break something else and say you guys did it again." My friends sister was truly evil. She was actually enjoying our humiliation.



They took us shopping for clothes on the first day of summer. The store was owned by a friend of our moms and she opened it early so we could come in and try things on. The only problem was she brought her daughter to work with her. Her daughter was our age and she went to our school.
"Hey Jake, hey Ben" Kristen said. She was laughing. We were so embarassed.
"Hey boys" Kristen's mom said. "Oh what cute girls they're going to make. So what do you need for them?"
"We'll need bras" Ms. G said. "But real ones won't fit them so trainer bras. Underwear. Blouses, skirts, dresses."
"And pantyhose" my mom said. She was already warming up to the idea of having a daughter instead of a son for the whole summer.
"Oh yes tights and pantyhose and stockings too."
"We should get them shoes too" Jenna and Nicole said. Our moms brought us but of course Nicole and Jenna insisted on coming with them too.

They picked stuff out for us and made us try everything on. They called us to come out of the dressing room at some point. We didn't want Kristen or her mom to see us but they kept calling us until we came out. We came out wearing dresses and pantyhose. You could see right through the hose and Kristen saw our pink toenails.
"Nice nail polish" she laughed again.

They made us try on shoes. They bought us each a pair of flat shoes, a pair of pumps with long heels that were impossible for us to walk in, and a pair of wedges with open toes. They paid for our things and Kristen asked if she could stop by the house sometime. Ms. G and my mom both agreed.



The first week of summer was a nightmare. We spent most our time bound, gagged, and dressed as girls. The dresses, bras, panties, and hose made us sweat a lot and the first week of summer was very hot. They had untie us to shower at least twice a day and change our clothes. And there were plenty of clothes for us to wear so we never ran out. Every day it was dresses or skirts and blouses. And always stockings or pantyhose.

Jenna and Nicole used their socks for gags or sometimes their moms nylons. We hated every minute of it. And the ropes and gags made us feel helpless.

After the first week Ms. G had to go out of town for a few days and she took Ben and Jenna with her. That left me at the mercy of my own mom. To the best of my knowledge she had never tied anyone up before. But I guess there's a first time for everything.

Re: Tricked By Friend's Sister

Postby CHillDice » Mon Oct 16, 2017 3:17 pm

GULP!!!
You got to ro ooo ooll me, and call me THE TUMBLING DICE!!!

Re: Tricked By Friend's Sister

Postby Unknown » Fri Oct 20, 2017 8:57 pm

My mom made sure to take a bunch of my clothes and shoes from Ms. G's house. Ben was gone with his mom and sister for a couple of days. My mom didn't have to continue my punishment in their absence but she insisted on it. As I said she was warming up to the idea of having a daughter for the summer instead of a son.

My nails were worn out so she used nail polish remover to clean them and then she used some of her nail polish to paint them.
"I think we'll use red. I bet you're tired of the pink polish. How's that sound?"

I didn't say anything so she started painting. When my nails dried she gave me a trainer bra, underwear, a red dress, and flesh colored pantyhose to put on.
"Are you really going to make me do this?"
"Uh huh" she said.
"Mom please this is so humiliating. I'm sorry we broke Ms. G's vase. Can't you just ground me for the summer."
"You are grounded" she said. "But instead of taking your phone or computer away, we're grounding you this way. I know it seems strange but I think you will come away from this experience more well behaved and respectful to me and other women. I also think you will have a greater appreciation for what women go through to live up to mens standards. Painting our nails, wearing makeup, putting on the dresses and skirts and stockings and pantyhose. I think you'll appreciate your mom a lot more and understand how hard it is for women who live in a male dominated society."

I went to the bathroom to change. When I was dressed my mom had some rope she borrowed from Jenna and a roll of duct tape. She took me to my room and I lied on my stomach so she could tie my hands behind my back. For someone who'd never tied anyone up before she knew what she was doing. Maybe Jenna and Nicole showed her some tricks. She tied my ankles tightly after my wrists and then used more rope to tie my wrists and ankles together. My mom had hogtied me!

My mom travled a lot for work and wore a lot of pant suits since she was a business woman. And under her pant suits she usually wore stockings up to her knees. And that's what she used to gag me. Two knee high stockings stuffed in my mouth and then tape.
"Are you really going to stuff those in my mouth?" I asked right before she gagged.
"Mmhm" she said. She was grinning when she stuffed them in. Then a fiew pieces of duct tape over my mouth to shut me up.

She left me to struggle for two hours and then came back. "Wow the house is so quiet" she said. "I wish I would've gagged you a long long time ago." I grunted loudly.
"Tickle, tickle, tickle" she said and stroked my hogtied feet. I mmphed and curled my toes. She stopped after a minute. "I'll tickle you more later on. And maybe I'll have you give me a foot massage later too."

I gotta cut this short. I'll continue soon.

Re: Tricked By Friend's Sister

Postby PiggyBoy » Mon Oct 23, 2017 6:00 pm

Keep it up! Your stories are always my favorites!
PM me if you ever want to hear stories or ask me questions! Oink oink! :8)

Re: Tricked By Friend's Sister

Postby TapedTy » Wed Oct 25, 2017 4:26 pm

Really enjoying it, can't wait to hear more

Re: Tricked By Friend's Sister

Postby Unknown » Thu Nov 09, 2017 9:53 pm

She kept me tied up for another two hours before she freed me. I went to rip the tape off but she said "ah ah you don't need your mouth to use the bathroom."

I went to the bathroom and then met my mom in the living room. She was sitting on the couch and she had me get down on my knees and take off her slippers. She had tan stockings on that went up to her knees. "Massage my feet."

I rubbed one stockinged foot at a time. She curled and wiggled her toes to taunt me. This was my first time giving my mom a massage. She'd never asked for one before and now she wasn't even asking. She was telling me to do it. I don't know if she really wanted a massage or if she was doing it to remind me she was in charge.

"I need you to move in closer. I want you to get a good whiff." I groaned. That was all I could do with my gag on. I had no choice but to breathe through my nose and every time I breathed in I would catch a whiff of her sweaty feet. I did as she said and moved closer. Now my nose was inches away from her toes and the smell was much stronger.

I ate a few hours later and then I served her for the rest of the night was my gag on. I brought her food or drinks or rubbed her feet or cleaned up for her. Then it was time for bed.
"I won't tie you up again but I want you to sleep with your gag on. Only take it off if its an emergency."

I grunted but did what she said and slept with my gag on. In the morning I got to take it off and spit out her disgusting nylons. They tasted like a combination of salt and cheese. It was the worst thing I'd ever tasted. I went to the bathroom, showered, ate breakfast.

Then I changed and put on a fresh trainer bra, clean panties, a purple dress, and purple colored pantyhose.
"Open wide" my mom said and rolled up the nylons she was wearing when I gave her a massage. I reluctantly opened my mouth and she shoved them in and taped my mouth.
"I have to go out. You can stay here. I won't tie you up but I want you to keep that gag on. Don't get any bright ideas about removing it. I have a new job for you."

So mom left and I started my new job polishing her shoes. She took all the pairs out of her closet she wanted me to clean. I got a cloth and shoe polish and polished six pairs of heels and flats. I kept the gag on the whole time. Her stockings tasted so gross. I started worrying about the state of the nylons she was currently wearing and worried if she would use them to change my gag later on. I felt pathetic being dressed like a girl, gagged, and polishing my moms shoes. I wondered what the guys at school would say if they found out. They would taunt and redicule us endlessly. That's why we had to do this or Ben's sister and her friend would expose us.

Mom returned a few hours later and complimented me on a job well done. I used the bathroom and then it was back to my room where I was tied hand and foot.
"I'm going to keep your gag on for now but if the tickling becomes too intense and you can't breathe just signal me and I'll take it off."
Tickling? Oh no. My mom was going to tickle me while I was tied and helpless. She started with the "this little piggy goes to market" routine. Then she went crazy running her fingers up and down my nylon clad feet. I squealed into my gag and tried to curl my toes up to protect my feet just a tiny bit but it did no good.

I ate dinner later and used the bathroom again. Then it was time for a new gag. She took the stockings off she had worn all day and shoved them in my mouth. I noticed they were wet and then I realized why. It was her sweat! I gagged from the taste. She taped my mouth shut and it was lights out. She didn't tie me up again but I had to sleep with the gag on again.

This went on for one more day and then Ben and his family were back. My mom sent me back over to their house the day they got home. Jenna couldn't wait to get Ben's nails painted and back into his girls clothes again.

I was kind of happy when Ben came back because the focus wasn't just on me. We were bound and gagged in Ben's room when Jenna and Nicole came in with a surprise.
"We ordered pizza. You boys hungry?"
"Mmhm" we grunted and shook our heads.
"Ok one catch. You have to eat it while we're holding it between our toes! And you have to clean up any mess."

Got to cut this short. I will continue soon.

Re: Tricked By Friend's Sister

Postby randomboy18 » Fri Nov 10, 2017 12:55 pm

Nice part. Maybe add him licking his mom feet and the girls