Caught By A Friend
  • Author - crazymike
  • Rating -   
  • Site Rank - 541 of 2955
  • Story Codes - F-m, m-self, consensual, analplay, caught, cross-dressing, self-bondage, teen, toys
  • Post Date - 7/5/2012

Author's Note: I'm not gay, I just have a lot of fantasies, so here is my second story. Let me know if you like it or not by leaving constructive comments.

[Editor's Note: I attempted to edit this story without destroying crazymike's style of writting or use of language. The text differs only slightly from the original posted on 7/5/12, but has been formatted and edited for your reading enjoyment. -mrhungry ]


Chapter One

It was Saturday night and I was at my best friend, Kori's, brother's house because she had just graduated high school. Kori and I are both 19 years old, and have been friends forever. We'd been drinking quite a bit that night, and since I lived about a mile and a half from the party I decided to leave my '87 Jeep Wrangler and walk home. I was not going to get a DUI on this night, so I told her to bring it to my house when she got up since she lives right next to me.

It took about forty-five minutes to stagger home, and when I got there I found my way into the shower, drunk, swaying back and forth under the spray. God, it sucked being drunk like I was!

After sobering up a little, I dried off and went to my bedroom and grabbed my 'special box' from the closet that was full of the bondage gear that my ex-girlfriend had left behind when we broke up a year ago. She was into all that, but I wasn't really into it that much at the time.

In the box was a bra, a pair of silicon boobs with realistic nipples, 6 pair of her panties that I had kept, a mini skirt, and a pair of knee high boots that were a men's size 12. My ex had bought those boots for me to wear but I never did, so they still looked brand new. There were also several varieties of gags and butt plugs, vibrators, several pairs of handcuffs, and some rope.

Looking through the box brought back memories of me and my ex playing around with bondage and some of the kinky sex we had. I was rambling round in the box when I found a smaller box with my name written on top. When I opened it I found a letter addressed to me from my ex, it said. "I know that you liked to wear my clothes when I was not around, so I bought these items for you. I hope you like them." I opened the box and found a pair of stockings and a long, blonde haired, wig.

Still being somewhat drunk, I decided to wear some of the clothes. So I pulled on the bra and inserted the silicone boobs into the cups. Just doing that made my dick hard real quick, so I slipped on all the panties I had so it wouldn't look like I had a dick at all.

Kind of excited now, I stepped into the stockings and wiggled them up my legs. I have to admit the nylons against my flesh felt terrific and I couldn't help but to run my hands over them for awhile. I put on the mini skirt and then the wig. It took awhile to get it to look right, because I'd never worn a wig before and it was pretty weird.

It's hard to describe the feelings that were going through me, but I started to rub my dick through the nylons and all those layers of panties. It felt so damn good, but I had to stop myself or I was going to cum. I went to the mirror to look at myself and fixed the bra so that the fake boobs looked better. My fake boobs looked pretty good, but I needed a shirt to get the full effect, so pulled one out of my drawer and put it on.

By this time it was about 12:00am Sunday morning, and even though I was finding this really exciting, I was dead tired and wanted to get some sleep. I grabbed one of the butt plugs that vibrated and worked it into my asshole. That took some doing, but I finally got it seated correctly. The vibrations sure felt strange, but...good in a weird way, too.

Remembering how my ex used to like to do things, I took the handcuffs and put them on either side of the bed, and did the same with the ankle cuffs at the foot of the bed. I grabbed a random gag from the box and pulled out a 4 inch penis gag. I put that in my mouth and strapped it as tight as possible and then slipped a small lock through the buckle in back.

I lay down on my bed and locked my ankles into the cuffs. Then I locked the cuff around my left hand and took the key and attached it to the middle of the cuff. I took the other cuff and put it on my right wrist. It took a little effort, but I finally managed to hook the other end of the handcuff over a hook my ex had put on the headboard.

It wasn't like I was really helpless, but it would take some time to get that cuff off the hook. I struggled for a little while, pretending I was some chick caught by a sex fiend and about to get raped, but I think the booze finally caught up with me and I dozed off.


It was about 8:00 the next morning when I heard my Jeep pulling in my driveway. I went to get up and get dressed, but found myself cuffed to my bed. What the hell? I looked down and saw the fake boobs under the shirt, and the skirt, and the stockings, and the boots, and what I had done the previous evening began to filter through my hung-over brain.

Shit! I remembered asking Kori to drive my Jeep over when she got up, and now I had to get myself out of the cuffs, and out of the clothes, before she started pounding on the door!

I struggled to get the right cuff off the hook, and was relieved that it didn't take as much effort as I had thought it would. I started to unlock my left cuff when I heard the spare key in the door. I heard Kori yell up to me, but she never heard me and she started up the stairs. I heard a knock at my bedroom door then the knob turned.

When she walked in I was still trying to unlock my left handcuff. She said to stop where I was, and ordered me to throw the key on the floor. I looked up at her like, what?...but did as she said. She came over to me and relocked my right cuff and then tightened my left cuff a tad. She left me there and made a phone call, telling someone that she wouldn't be back down. I assumed she was talking to her sister since she'd been hanging out with her. Once she was off the phone she went to the bathroom and then returned to look at me.

I had been bound like this a few times with my ex, but I had never been as horny as I was right then. This time I really felt helpless. This time I really felt embarrassed, and humiliated. This time I really felt I was at someone's mercy, and that someone was my best friend, Kori. To have her see me like this was so embarrassing, but at the same time my dick was so hard it hurt! I couldn't believe how turned on I was at Kori finding me like I was, and her reaction to it.

My friend walked over and picked up the key for my gag and unlocked it. She asked me what I was doing and I told her that I was only fooling around with my ex's old stuff but had fallen asleep. I woke up when I heard her pull into the driveway. To my surprise, she said needed to get something from her house and would be back in an hour or so. She relocked my gag and then left me, closing the door behind her.


When Kori came back to my house, and came into my bedroom, I saw that she had changed into a nice mini skirt, a belly shirt, and knee high boots. She also had two bags full of things.

In one of the bags she had rope, locks, and some retching straps. In the other bag she had more butt plugs, a strap-on dildo, and a vibrator for my tongue to play with her pussy.

She unlocked and removed my gag and then took the tongue vibrator and pulled it onto my tongue. She climbed on top of me and ordered me to lick her pussy. I hesitated, not that I didn't want to, but because it was Kori, my best friend. She told me if I wanted to ever be let go I had better start licking.

The vibrator felt weird on my tongue, but I did as she ordered, and began pressing my tongue against her pussy. After 20 minutes or so she started to tense up and soon she was cumming all over my face. It tasted great, and I just kept stroking her pussy with the little tongue vibrator as Kori cried out in pleasure above me. When she had finished climaxing, she took the vibrator off my tongue and I was forced to lick her clean. I say forced, but by then I was so horny I would've volunteered to do it.

I think she actually came again, because after I thought I had licked her clean there seemed to be more juices flowing out of her pussy. I guess she was satisfied with what I had done to her because she got off of the bed and went to her bag to get her 9" strap-on. After strapping it on, she climbed on top of me again and started to fuck my mouth with her cock.

Obviously, I had never had a cock in my mouth before, real or fake, and I gagged as she pushed it into my mouth. Kori must have still been horny as hell as she continued to force the hard cock down my throat.

Finally, she got off of me, unlocked the cuffs holding my ankles to the bed, and started to strip me from the waist down. I was surprised when she made her way up the bed between my legs and began to lick the pre-cum from my cock. She slid a condom over my cock then rode me really hard until we both came. I'm not sure who cried out the loudest as it seemed I would never stop cumming into the condom.

Kori dismounted me and started to slide the condom off of my cock. As she did, she pinched off my cum in the condom, not allowing any of it to spill out onto the bed. I thought that was pretty nice of her until she put the open end into my mouth and I realized what she was doing with it. She had gotten back on the bed and was sitting on my chest with her knees on either side of my head, holding me tightly. She released the end of the condom and allowed the cum to drain straight into my mouth.

With Kori holding my head between her knees I couldn't move away from her and was forced to swallow my own cum as she wrung every last drop out of the condom. She reached over and took the penis gag and reinserted it into my mouth, strapping it tighter than before and then locking it. Climbing off of me, she pulled the panties, nylons, and skirt back up and adjusted them so they were on me right.

I was exhausted by this time. Not only was I suffering from a monster hang-over, but I had just had mind-blowing sex with a woman I had secretly lusted after for many years. I wanted nothing more at this point than to drift off into a mind-numbing sleep, but Kori must have had other ideas.

She took some ankle cuffs with a chain in the middle from her bag and locked them onto my ankles, over the boots. Then she unlocked my wrists from the headboard and told me to sit up. She dug some nice leather wrist cuffs out of her bag and locked them on my wrists, bringing them behind my back and clipping them together.

Pulling me off the bed, she forced me to the floor, took the rope that she had, and ran it around the ankle cuff chain and up to my wrist cuff chain, tightening it as tight as she could. I could've fought againt her, but I was more interested to see where this was going! Before I knew it, I found myself in a tight hog tie. She said that she was going to leave me there for a couple of hours because she had to run to her house and then go to the store.

I put my head on the floor and watched her leave the room, the door closing with a loud slam as she left. My head sagged to the floor and it wasn't long before I passed out - with a smile on my face.





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