literature

Don't Make a Bet you'll Regret

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((Bondage, Crossdress fic))

(Sorry for the hiatus, college finals are deadly to creativity. Here's an old story I rewrote to make up for it!)

My girlfriend wanted to hang out tonight, so we decided that she would come over tonight. She got to my house right at 6 o’clock, but I was still doing my homework. For some reason, I was just having a hard time with calc today. She told me she would help me with it, for a cost. I asked her what she wanted. She wanted to tie me up. Made sense. I made her a bet. After my homework, I would tie her up, and if she could get out in ten minutes, she could dress me up, give me a makeover as if I were a doll, and tie me up and keep me tied up for as long as long as she wanted. I also agreed to be her personal bondage slave every weekend for a year. If I won, I could tie her up 10 times a month for a year with as strict of bondage as I wanted. She hastily agreed.


I finished my homework quickly with her help, and within a couple of minutes, we were ready to begin our bet. I took off her shoes and tied her ankles together with our signature purple duct tape. Pretty much all of our restraints and bondage paraphernalia were purple or black, as purple was our favorite color. I wrapped around her ankles 5 times before moving on to her wrists. I crossed her wrists and rolled the tape around 5 times. Then I went over to her mouth and told her to open wide. I shoved a bandana deep into her mouth, then put 5 strips of duct tape over her lips so she couldn't spit out the cloth. She made a loud mfff in protest, but I ignored it. I counted down from 5 and the started the ten minute timer. She struggled in her bonds for a good 5 minutes before she got her legs free. If it took her that long to get her legs free, there was no way she would win. With two minutes left, she began to make progress on her wrists. I started to fear that she may escape in the time limit. With ten seconds left, she freed her wrists, ripped off her gag, and hit the timer. I hadn't expected her to escape, so I was scared of what she would do to me.


We went to her house, as most of our stuff was there, and she gave me a bag of clothes to put on. Inside was a corset, long, black gloves, dark purple high heels, nylon tights, and a bra. I reluctantly slipped them on, and she helped me with the corset, tightening it to the point where I could barely bend over, and the bra, stuffing it so it’d stay on. She then gave me a purple maid outfit with puffy shoulders, which she helped me put on as well. Once that was all set, she walked me to an armchair and used the purple duct tape to tie me down. She got out a roll of purple vet wrap, forced my hands into fists, and rolled the tape around until it appeared as if two purple balls were attached to my wrists. Then she took off her purple panties and shoved them deep into my mouth, and then she buckled a purple ball gag into place. She really was going all out. I knew what was next. She got her makeup kit out, and quickly applied eyeshadow, eyeliner, lipstick, and blush. Next, she grabbed a can of hairspray, multiple hairpins and hairties, and her curler. Then she took my hair, played around with it for a few minutes, tried a few different hairstyles and decided to put it into an updo after curling it. As she pulled and tied, i wondered how girls could deal with this every day. She asked me if I liked it, putting a mirror in front of me, but my gag wouldn't allow me to answer verbally. I shook my head no and she slapped me. She told me I should be thankful that I get to be her doll. She told me I looked adorable and pinched my cheeks. She took a picture of her next to me in the mirror. She wouldn’t share the pic though, those were always just for us.


Since the makeover was done, she unstrapped me from the chair but left my gag in, and led me to her bed. She set up her camera, then took some long pieces of rope and tightly knotted my legs together at my ankles and above and below my kneecaps. She then tied my wrists in the same knots, and then tied my arms at my elbows. Damn, it was strict! Then she used the purple duct tape again to reinforce the bonds, making them even tighter. There was no way I was getting out on my own. Over my arm ties, she used an armbinder to make arm movement impossible. She took pictures of her holding me in her arms, bridal-style, and others where I was on the ground and she was sitting or lying on me or had her foot on my chest or face and was doing a victory pose. She also took a couple of her licking or kissing me. She then set me on her bed. She passed a rope through my ankle ropes and the ring on my armbinder and pulled until there was no slack left. I was now hogtied, and I could do nothing about it. Then she tied a rope through the ring of my ball gag to my ankles and my head lurched up, with not even enough slack to turn my head. She started to tickle me, and I tried furiously to escape, but couldn't loosen the bonds at all. I was here until she decided I could go free. She tickled me for what felt like hours. She took a few more pictures before leaving for a few minutes. She came back in her pajamas. Her parents said I could stay over for the weekend, so she wasn't going to untie me. My first weekend of bondage was starting today. I tried to struggle in my bonds, but I couldn't move an inch. She said she was going to bed, so she kissed my cheek, got in bed and fell asleep with her feet rubbing on my face. I couldn't help but wonder what tomorrow would hold.


Hey guys! Sorry about a long wait, but hopefully it's worth it! This story features some serious bondage, crossdressing, gags, and a playful bet. I hope you all enjoy!

(I may expand upon this, but probably not)
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rubberjoyboi's avatar

i love this story