Sam

My mom was a single parent and her job required her to travel every weekend. She would hire a babysitter when I was a kid but as I got a little older she let me stay home alone. She would leave money for food or anything I might need. And I was allowed to have friends stay over.

When I was 14 I had my next door neighbor and friend stay over one weekend. John had stayed over plenty of times before but this weekend was going to be very different. John was acting a bit strange but he was always a bit of a weirdo so I thought nothing of it.

We hung out a bit, ordered pizza, played video games for a couple of hours. Then he said he was bored and suggested a game of truth or dare. I thought that was really odd because he had never suggested it before. But I figured okay why not.

I picked truth the first couple of times and he asked me the basic questions like who do you have a crush on, etc. He was just waiting for me to pick dare and when I did he immediately said "I dare you to wear your moms clothes." He didn't even think about it. It was like he had this planned it before he even came over.

I didn't want to do it but anyone who knows me will tell you I don't back out on a bet or a dare. We went upstairs to my moms room and I was just going to throw one of her dresses on over my clothes and be done with it. But John kept egging me on and calling me chicken and saying that it wasn't the dare and that I had to go through with it. I sighed and we went through her drawers.

I picked out a bra and matching pair of panties. Then a dress. John pulled out a pair of pantyhose from my moms drawer and threw it on top of the pile of clothes. "To complete the look" he said.

This kept getting weirder and weirder. Like I said John was always a weirdo but this was weird even for him. Did he want to see me dressed like a woman? Did he want other people to see me like this? Was he going to tell our friends at school or snap a picture of me when I wasn't looking? Why did he want me to do this? The dare was so specific. I should have known better but I went into the bathroom to put everything on and get this over with.

I had a little trouble with the bra and the pantyhose. The hose were black and they had Cuban heels with the seam running down the back of the legs. I had even more trouble zipping up the black dress I had picked. But I managed to get everything on right and it fit surprisingly well. I came out of the bathroom and John was gone.
"John? John? Where did you go?" Hahahaha very funny. My first thought was it must be a prank. I checked my room and my moms room. Then I went to go downstairs but before I reached the steps someone covered their hand over my mouth and dragged me into my room.
"Mmmph! Mmmph! Mmmph!"

They threw me onto the bed with one hand still covering my mouth. A ziptie was used to bind my wrists. They had to remove their hand from my mouth to do that. They did it fast and as soon as I started screaming for help they grabbed a dirty sock from my floor and stuffed it in my mouth.

They turned me around and of course it was John. I should have known. "Don't spit that out" he said.
He went through my drawers and found a roll of tape and used it to gag me before I even had a chance to spit the sock out. Then another zip tie was used to bind my ankles. The zipties were tight and they cut right into your skin.
"Don't worry the zipties are temporary" he said.
"Whff thm hmph?" I tried to say what the hell but it didn't sound like it.
He left the room and came back with his overnight bag. There was rope inside the bag, a ton of it. I groaned into my gag as soon as I saw it.

He used rope to tie my ankles first and then he cut off the ziptie. More rope was used to tie my knees. Then my wrists were tied tightly behind my back and the other ziptie was cut off my hands.
"Struggle if you want but you're not going to get out. I used to be in the boy scouts. I know my knots."
I mumbled a few curse words through my gag. He laughed and reached down with one hand to tickle my feet. I kicked my feet around and begged for him to stop but with the gag it was no use. And he was right. I couldn't escape.

He sat down to get in closer to my feet and tickled me for an hour straight. Well he did give me breaks in between so I could catch my breath but he kept this up for an hour and then he gave it a rest. He watched the tv in my room and played video games by himself. I was on my side at one point with my back turned to him and I felt him touch me. I thought he was going to tickle me again but he didn't really tickle me. He just traced the seam of the Cuban heel stockings up and down with his finger. I didn't move or make any noise through my gag. I thought it was very strange but I told you this kid was weird. And it got a little weirder after that. Nothing sexual at all I just want to be very clear about that. But you will see what I mean.

You still awake?"
"Mmhm" I grunted through my gag.
"It's late. I'm going to turn out the lights. See you in the morning. Your moms bed looks pretty comfy so I think I'll sleep in the master bedroom. Goodnight."
Then before he went to bed he gave me two soft pecks on each of my soles. He kissed my feet. This weirdo actually kissed my feet goodnight.


I woke the next morning up to John tickling my nylon feet.
"Cootchie cootchie coo" he taunted me. I groaned through my gag.
"You must be hating that gag by now huh?"
"MMHM" I grunted loudly.
"Well I'll see what I can do for you in a little while."
"Mmmfff! Mmmmfff! Mmmmmff!" I was screaming through my gag because I was tied up all night and I really needed to use the bathroom.

"Oh yes the bathroom. I'll untie you so you can go but you have to do exactly as I say. And you don't really have a choice. I hid all of your clothes while you were sleeping so this is all you have to wear. I also took some pictures of you while you were sleeping. So unless you want everyone in school to see you dressed up in your moms clothes you better do what I say. Got it?"
I grunted and nodded. He untied me and told me not to remove my gag. I used the bathroom and he made himself breakfast. He made something for me too and finally let me take the gag off when it was ready. I ripped the tape off and spit my nasty sock out.
"Why are you doing this to me?" I asked when we were eating.

"My older cousin used to do this to me. She would dress me up in her old clothes, tie me up, tickle me, put makeup on me, paint my nails. I  hated it at first but then I started liking it. She stopped doing it a few years ago and I always wanted to recreate the experience but be on the other side of things. And I knew I could probably trick you into putting on your moms clothes. But just go along with it alright? It's a lot better than everyone at school seeing those pictures. I mean you could tell them I made you do it and it was my idea but you still went through with it so it won't help you. And trust me you'll start to like it eventually."
Eventually? How long as he going to make me do this? Was he going to use those pics to make me do this again?

He wanted to tie me up again after breakfast. I went along with it and didn't fight him. My wrists were bound behind my back. Then he tied my ankles. More rope was tied above and below my knees. He saved the worst for last.
He found another dirty sock that belonged to me and balled it up. "Open wide" he grinned. He crammed that disgusting sock in my mouth and gagged me with duct tape.

"I won't tickle you now. I'll save that for later since I have until tomorrow night when your mom gets back."
"What are you going to do to me?" I tried to say but it came out as mumbles and grunts.
He seemed to understand. "We're going to play a game. I'm going to roll dice and you can pick a number. If you pick the right now I will untie a part of your bonds like your knees or ankles. If you get enough right numbers I may even let you go free."

I rolled onto my back so my bound wrists were showing.
"Pick a number" he said. I couldn't answer with the gag so I put out seven fingers. People say that seven is a lucky number. But not for me.
He rolled the dice. "Eight" he said. "So close."

I picked another number. This time I held out five fingers.
"Seven" he said. "You should have picked the same number." I groaned into my gag. I was already hating this stupid game.
I picked again. This time I picked seven again. "Ten" he said after he rolled the dice.
I picked seven one more time and the dice landed on nine. I decided to try another number. This time I stuck out four fingers.
He rolled the dice. "Snake eyes" he said. "Man what a bummer."

This continued for an hour before I finally got a number when I chose 7 again. He kept his word and untied the rope above my knees. But the rope below my knees was still tight and my hands and feet were still bound.
We kept playing this dumb game for another two hours. I couldn't even see the dice since I was on my stomach with my bound wrists out so I could hold up my fingers for him to see. So he could have been lying for all I know because I didn't get another #. He finally gave it a rest and I was worried he was going to tickle me next but instead he started untying me.

"Keep that gag on and go to your mom's room. I picked out some new clothes for you to try on."
I went to my moms bedroom and there was a new bra, clean panties, an orange dress, and suntan colored pantyhose. I changed my clothes and went back to my room where John had the ropes all ready. I mumbled into my gag and rubbed my sore wrists.
"I know the rope hurts. It hurt when my cousin used to tie me up. I will give you a break before I tie you up again but you have to keep your gag on. Ok?"
I grunted and nodded.
"Good now stay here. I'll be back."

I sat on my bed and didn't remove my tape gag. This whole ordeal was so bizarre and mystifying but I really didn't want another living soul to find out about it so I just played along. I couldn't believe it. I was a prisoner in my own house!
John came back when he found something else for me to do while I was untied. "Put this on" he said and handed me a frilly pink apron to put over my dress. "While you're taking a break from bondage you might as well spruce the place up for your mom."

He got a feather dust and had me dust around the house with the pink apron over the dress. So humiliating. I did laundry after I finished dusting but I noticed a few of my socks were missing. I had an idea why and I didn't like it one bit. While the clothes were washing and drying I vacuumed the upstairs and then the living room.
"I think that's enough" John said after a few hours and let me take my gag off to eat since it was getting late. I got to use the bathroom afterwards and then it was back up to my room.

I was bound hand and foot, my wrists, ankles, and knees tied tightly together. Then John took out the socks that were missing from the laundry.
"One sock seems to fit fine so let's try two." Before I could protest he stuffed the first sock in. "Make room for the second one" he laughed. He crammed the other sock all the way in. My mouth was completely full and my cheeks felt like they were going to burst. He gagged me with duct tape and went to the end of the bed.
"Cootchie cootchie coo" he taunted me as he ran his fingers up and down my nylon feet.

He dug in with his fingers, scratching at my soles and arches. I squealed through my gag and tried to beg him to stop. Two socks made a remarkably effective gag and my words were incomprehensible.
"Cootchie cootchie coo" he taunted me over and over. He switched it up with the "tickle, tickle, tickle" taunt. It drove me crazy. Being tickled is bad enough but being endlessly taunted made it ten times worse.

"Did this little piggy go to market?" he joked as he tickled my toes. He ran his fingers back and forth over them and even tickled me in between my toes as best as he could with the nylons. He worked on my toes for ten minutes before he went back to my soles.

He gave me a break to catch my breath after the first 30 minutes of nonstop tickling.
"Grrmmmff mmmphhh hhmmmmppphhhh..." I quietly mumbled through my gag to beg him not to tickle me again. You can imagine how much good that did me. After a short break it was back to tickling my helpless feet.

I tried to curl my toes to dull the sensation a little but he caught on and excused himself. He came back with a ziptie and a few other items. He forced the ziptie in between my big toes even with the nylons on my feet and he tied it tightly. Now my big toes were bound together and I couldn't move my feet or curl my toes at all.
"Now where were we" he said and stroked one finger down my sole. I mumbled a few curse words through my gag.

He showed me the other items he had brought up. The feather duster I had used to dust the house, a plastic fork, and a hair brush. He used the feather duster first. Stroking it up and down my feet and back and forth across my toes. Then the plastic fork which kind of hurt more than it tickled. But it still tickled alot especially as it scraped against the nylon material of the stockings.

He saved the hair brush for last. It was sheer torture. All those pointy bristles scratching and poking at my soles and toes at once.
"Cootchie cootchie coo" he said. I let out a furious grunt through my gag. I hated that damn taunt. The tickling lasted another thirty minutes before he gave me another break. This went on for hours. Intense tickle torture for thirty minutes followed by a break, followed by more tickling.

I was so worn out by the end I couldn't struggle or moan or mumble. I just laid there in silence as I caught my breath. I smiled behind my gag because it was finally over. He cut the ziptie off my toes and I wiggled them around a bit.
"You need to go to the bathroom?"
"Mmm" I said and shook my head no.
"Good. It's late so lights out. I'll see you in the morning." And with that he gave the soles of my feet another soft peck like the night before. I shook my head. What a weirdo. He turned out the lights and rolled onto my side and tried to get comfortable. I reminded myself that my mom would be home tomorrow so I just had to put up with this for a little while longer and then I'd be free.

"Cootchie cootchie coo" I heard in the morning and felt him running his fingers up and down my helpless soles. I groaned into my gag but breathed a sigh of relief when I felt him untying my wrists, and then my knees and ankles. I rubbed my sore wrists and ankles and then ran for the bathroom. As soon as I came back to my room I pointed to my mouth and "mmphed" to ask him if I could remove my gag.
"No. Keep it on for now."

He made me keep it on until breakfast was ready and then I finally got to peel the tape and spit out those disgusting worn socks. After we ate I waited for him to tell me what was next. I assumed he was going to tie me up again and tickle me which I did not look forward to. But he had other plans. He gagged me with two more worn socks he put aside and tape and made me pick up where I left off the day before by cleaning my own house.

I didn't mind since it was a break from bondage and it guaranteed he wouldn't tickle me as long as I kept working. I made the beds, vacuumed again, dusted, and scrubbed. My mom came home earlier than I expected and walked in on me scrubbing the floors in her dress and hosiery.

"What on earth is this?" she shouted. I couldn't answer with the gag and before I could remove it John stepped in to offer an explanation.
"Hey Ms. G" he said. "Didn't think you would be back so soon. I can explain though. I caught Sam dressing up in your clothes and I promised I wouldn't tell anyone as long as he promised to be my slave for the weekend and do what I told him. And I figured since he was my slave I would take advantage and make him clean up around the house and make things nice for you when you got home. As far as the tape goes, he wasn't happy about having to clean the place up so I gagged him to keep him from complaining."

"Well I can't agree with your methods but the place does look amazing! And Sam has never been quieter! And he does look very cute in my dress too. Would you like to babysit next weekend when I go away? I'll pay you if you can make Sam clean like this for me and behave himself. He hardly listens to me and he never wants to do his chores."
"I would love to" John said.
"Mmmph! Mmmmph! Mmmmph!" I protested the idea through my gag, begging my mom not to be fooled by him.
"You know I'm starting to like the idea of that gag" my mom said. "I may have to try it sometime."

We went back up to my room and I ripped the tape off my lips and spit those nasty socks out.
"Don't tell your mom the truth unless you want everyone at school to find out your dressed up in your moms clothes. Just play along with what I said. See you next weekend."



My mom wasn't kidding. Not only did she pay my friend to "babysit" me but she laid out a set of clothes on her bed for me. Bra, panties, a white gown, and white pantyhose. She even left pads for me to fill the cups of the bra.

John showed up after school with his overnight bag that was filled with rope and tape. "Go  get dressed" he said. "Then the fun can begin."
"You can't be serious."
"Don't argue with your babysitter."
"I can't believe this" I said as I went to get dressed. When I was all dressed up he called me into my room.
"Just do me a favor. Please don't put any of my socks in my mouth."
"Your socks? No I'm going to use MY socks. I have been putting them aside all week for you. I'm going to start out with the socks I wore in gym class."