Shoulda
  • Author - Captain Howdy
  • Rating -   
  • Site Rank - 1156 of 2955
  • Story Codes - F-m, consensual, bondage, chastity, enema, humiliation, latex, toys
  • Post Date - 9/17/2010

Author's Note: Here is an old story I found the other day. I don't really have plans to continue the story, but if someone wants to make a continuation of the story feel free. Takes place in 2005 and yes it was written in 2005....


Part 1

I have been into bondage for a long time, but never had the gumption to ask anyone to participate. I did some self-bondage a few times when was a teen and it was very intense for me and I had feelings like never before when I engaged in those acts. The internet came out and I found there was a ton of people into bondage, I thought I was the only one, but still never had the balls to ask any girlfriend.

Well it's now year 2005 and I have a few favorite bondage sites I go to, and I usually go to them when my girlfriend goes to bed as she doesn't know my secret desires. Well all of that was going to change on one dreadful or happy day, whatever way you want to look at it, night. She went to bed at 10:00 like she always did while I stayed up and watched some TV. 11:00 rolled around, my TV show ended that I was watching and my girlfriend had to of been fast asleep by now.

Well I hopped onto my computer and jumped online. I first checked my e-mail and went to a few music sites to see what my favorite bands were up to. After all that was done I went directly to my favorite bondage sites. I was then on a website call "The Sub Shop" and was looking at all these neat things I wanted but couldn't buy as I didn't have anyone to share them with. Little did I know my girlfriend was standing behind me the whole time. She watched as I looked at a bunch of Bondage equipment and rubbed myself the whole time. My girlfriend quietly went back to the bedroom as she planned something evil.

We both awoke and she said she had to go to work an hour early and left. I waited until I had to open my store and then I left as well to work all day again for a few bucks. Well my girl called me later that day and said she had won a one week vacation and told me to place a sign on my door saying I'd be closed for a week for being on vacation. I thought sweet finally a vacation so I can rest and not worry about my store.

I got home and she already had a suitcase ready and everything. She was also dressed in her sexy clothes and I knew what that meant, she wanted some! She ordered me to undress and I replied instantly. She told me to get on the bed; I found this strange because she always wanted to be on bottom. She then produced a roll of duck tape. She then told me to close my eyes, so I did. She then placed a piece of duck tape over my eyes, she told me to close my mouth, I complied and a couple pieces went over my mouth. What came next was a total surprise. She told me she was going to put some special underwear on me; however Jr. has to be limp please. I thought of Rosanne and I went limp instantly. She then proceeded to put these pants on me; they were snug and felt thick. She the told me she was putting something else on me and it might feel strange, while pulling this garment up my legs it felt as if it was leg warmers, strange she'd put leg warmers on me I thought. She then told me to put my arms out and I did as my arms went through this thing whatever it was, I was then told to roll over onto my stomach. She took a zipper and zipped it up to my neck. I thought oh my god I know what this is it's a leotard of some sort. I then felt some liquid on my neck and she laughed most evilly.

I was told to roll over again and the tape was taken off of my mouth and off of my eyes. I could finally see what she had done. She put me in a pull-up diaper and she also did put me in a leotard. She then told me it'd be useless to try and get free as the zipper had been super-glued! She then told me about how she found out that I liked bondage. She told me she thought I liked it but wasn't for sure until she caught me on the bondage sites. She also said she had ordered a bunch of stuff from my Sub-Shop that I was on, and ordered stuff I looked at! I was then told that there was no vacation and the whole next week would be bondage slave week for me. She then took me down into the basement where she had a bucket swing, a slightly larger version of the toddler swings you see at the park. I was told to get in it and I complied. The swing was then attached to two chains hanging from the ceiling. I was told to put out my fists and she proceeded to tape them up so I couldn't use my hands to get myself free. I was told this is where and how I'd sleep for the night, she told me to use the diaper if I had to pee or poop! She walked away leaving me hanging there in the swing, then the lights turn out and I am there in a leotard, in a diaper, hands bound and in a swing that I can't escape. This was almost great for me as I hadn't really done any self bondage in a few years. I could only imagine what lay ahead for this week.

The night went by faster than I imagined, I had wet the diaper once and heard my girlfriend walking around upstairs. A knock at the door, it was the postman. She came down stairs with a few boxes, mocking me asking if I knew what they were. She opened all the boxes and laid the items on a table that was near me. She pulled out a couple different gags, some wrist and ankle cuffs, some latex pants and so much more. She must have spent a couple hundred on this stuff if not a thousand. I recognized some of the items that I have seen many times and a couple I didn't remember looking at. She told me she had to go to work and would be coming back home in a little over 5 hours. In the meantime I need you to be quiet. She grabs the gags she had purchased. She wanted me to choose what one to wear. She showed me a penis gag that looked like a trainer style gag, she then showed me a pony-bit gag that also was a trainer style gag, another trainer gag was produced in the form of a ball gag and she then showed me the last gag she had purchase and it was a pump style gag. I didn't want to choose and she said well I guess I'll choose for you. She put the pump gag aside and said that was for if I was a bad boy during the week. She then put the pony bit gag aside telling me that I would have animal time this week, I actually wanted to wear the bit gag because I was intrigued by pony girls n boys and the recent pony sites I have recently visited. Then held the ball gag and penis gag in her hands, threw the ball gag aside and proceeded to put the penis gag in my mouth, a penis was the last thing I wanted to have in my mouth gag or real. I tried my best not to let it go in my mouth but being helpless as I was it didn't take much effort for her to put the penis gag in my mouth. She proceeded to strap it onto my head and was finished. It was a breather gag as I could feel the hole at the head of the penis with my tongue. My girlfriend then pulled out a rubber hose that was small enough to fit in the breather hole in the front of the gag. She then put the other end of the tube in a 2-liter of Mountain Dew and told me if I was thirsty to just suck on my new friend and I'd get to drink some Mountain Dew, she knew I would get thirsty sometime in the next 5 hours. She then soon left for work.

I was there in the swing and having to pee again and I also had to take a shit. It was 3 hours into the ordeal and my bum felt gross from having soiling in the diaper she left me in. I was getting thirsty and I had no choice but to suck away on this gag. I sucked hard and barely got any in my mouth almost the same amount as a normal man ejaculates, this must have been her plan. Well I was damned thirsty and worked at getting more than a swallow at a time. Well my wok paid off and I drank about ½ of the 2 liter.

It was time she was getting home and I heard not one but two cars pull up and 3 car doors, gee its bad enough she is giving me what I kind of wanted for a long time but she was bringing friends too! She and her friends came downstairs and she showed off her masterpiece. She looked and saw that I had drunk ½ of the 2 liter and mentioned I was hell of a sucker. It made my face turn red. She released my from the swing and told me turn around, she put something on the zipper so she could remove the leotard she had enslaved me in. She then pulled out a plastic sheet for me to lie down on and she removed the diaper that was full as could be. She and her friends laughed at the shit in my pants. I was then walked up to the bathroom and told to get in the shower. An enema was pulled out from the bathroom closet. She gave me an enema and as she pulled the nozzle out she put a few tampons up my ass and the expanded instantly. I was then given a shower and was washed with this stuff that stung a little bit. She let the soap set in and then she started to wash all the soap off. I noticed some of my hair coming off of my body, as she laughed about me being nice n silky smooth. She grabbed the strings that were hanging from my ass and pulled, a strange feeling came over me as she pulled them out. I was then allowed to sit on the toilet to shit out the enema water. I was given 2 more enemas to ensure I was clean and empty of all poop. I was placed in the shower again for one last wash down. I was then walked down to the basement again. There her friends were standing with a bunch of stuff laid out for use on me. A chastity belt was produced by one of them and it was put on me fast and swiftly, I wonder if she had done that before. The chastity belt had two small locks on it and made it so that my cock wouldn't get any bigger than three inches. There were two straps one around the base of my cock and the other around my ball sack. It was a strange sensation that I think I liked but I couldn't get hard as it prevented me from doing so. Then the latex pants were shown. They were the ones with a built in dildo for ass play and my eyes opened and I didn't want that thing put on me. I started to protest but my girlfriend threatened the penis gag again. I started to plead that I didn't want a penis shaped anything in my ass, but my complaints fell on deaf ears. Not only was the penis gag put back on me in no time, the latex panties were forced on me. The dildo went straight up my ass and the panties feeling ever so snug on my encased cock. My heart was racing and I was enjoying myself. Latex Wrist cuffs were then placed on me and locked, and so were ankle restraints and they were locked as well. The large style toddler swing was replaced by a sex swing. I was ordered to get in the swing so I did as I really had no choice. The wrist and ankle cuffs were attached to these rings on the swing and now I had no way of escaping. Her other friend pulled a cat o 9 tails out of a small bag. The swing was adjusted so my behind was more available to them. I was lightly whipped to start with. My behind started to feel warm and warmer from each whipping. They started to whip my ass harder and the dildo panties I had on started to almost vibrate in a way. The whips would make me aware of the dildo pants and I would flinch at each whipping which made the dildo vibrate and it was one of the strangest feelings ever, I wondered if that's what being butt fucked was like.

After they were done having fun with me on the swing I was let down. My wrists were then pulled behind my back and then they were bound. The penis gag was taken off of me. I was allowed to take a breather. My girlfriend asked how I liked my bondage night. I replied that it was ok other than the dildo in the ass and penis gag, she grinned evilly almost as if that was the only gag she was going to use. A moment later a mask with attached panties was produced, I wondered what this thing was as I didn't remember seeing this item on the web. My girlfriend put a strap-on on and put the panties/hood on. I soon realized what this panty/hood thing was for. This thing was made so that a person was forced to give oral service to a man or in this case I was forced to give service to a strap-on worn by my girlfriend. I was made to crawl over to her on my knees, and then the hood was put on my head. The dildo from the strap-on was right there at my mouth so there was no way I could avoid having this new cock in my mouth. I felt two hands on my head and was forced to suck on this new toy of hers. The latex of the mask acted almost like a rubber band making the dildo going in and out of my mouth. I was told to suck on it as if I was her and she was me. I was taught the ways of sucking in a matter of minutes. It went in & out and there were moments she shoved the thing to the back of my throat. A few moments later one of her friends started to rub the dildo panties I still had on, making me aware of the dildo still in my ass. I started to almost cry but being muffled as I couldn't really speak as my mouth was full; they all thought I was making moans of enjoyment and ecstasy. This lasted about 20 minutes or so, about the length that she always sucked me off.

One of her friends went out to their car to grab something. As she was gone getting whatever it was, my girl took the penis panties off of me she pulled out another diaper and she also pulled out a butt-plug! The plug was put in my ass, with some effort she finally got in there. A tear or two came from my eyes as it popped in. She then told me she had to get me ready for the strap-on tomorrow. My eyes opened wide and I ask what she meant by that. The ball gag was brought out and put on my head. This gag was a locking style gag as it was locked onto my head. I was grateful that the penis gag wasn't put back on. She didn't like me talking I guess. I was then diapered again and the leotard put on me and the zipper was super glued again. This time the duck tape that was on my hands was taken off. No sooner after the tape was taken off her friend requested help at the top of the stairs. The other friend of hers that came over went up to help out. They were bringing down a cage that was folded up. They started to unfold the cage and then it dawned on me that it was meant for me! It was big enough to hold a fully grown German Sheppard or St Bernard! A collar was put on my neck; it was quit large and stiff. I barely could move my head with it on. This collar was also a locking style as the collar was locked on to my neck. I was then lead into the cage by the collar almost as if I were an animal in need of training and the cage door was shut behind me and then that also was locked! I was only allowed to move on my hands and knees. It was wild that 5 hours had already passed during this bondage session. My girlfriend told me that we would continue sometime tomorrow.

She and her two friends went upstairs and the light was turned off on me. I sat there in my new home, for the week only I had hoped, I could only wonder if my girlfriend was into bondage or got friends that were into it to teach her the ways of bondage. Either way I was bummed out that a chastity device was on my cock so I couldn't even rub myself to climax, that's about the only bad thing other than the butt-plug in my ass stretching my hole open for my girls new strap-on play toy.





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