Caught in selfbondage at College

Well if you read my previous story, im gonna start numbering these so you know what order they go in, then you will probably be surprised to hear I graduated highschool a sissy virgin. A quick conclusion to the blackmail story is that the month passed by with lots of phone play and us meeting a couple more times. He had made mention of taking my virginity but I begged him not to. I wasn't ready for that and he agreed that if I promised to do what I was told then he would let me decide who to give it to. That story will come later but I still didn't really get to decide. After the month had passed we decided to stop seeing one another mainly because I was getting so busy with school and he had to refocus on work since he had spent the last month completely focused on me.

Ive decided to write my stories in order from oldest to newest working through all the times my hubris or my horniness got me in trouble. Some people may read these and think, how in the world could one sissy, no matter how horny she is, get into so much trouble but what im not writing in these stories is all the times things went off without a hitch. The times I met up with someone, played, and then left and nothing in my life changed. The stories im writing are only the times that things went wrong...or right depending on what gets you off.

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I was a freshman in college, my second semester and my roommate and I did not get along. He was a home body, if he wasn't in class or getting food, then he was in the room on his computer. This unfortunately had the effect of making it impossible to have any fun, personal or interpersonal. I couldn't dress up, tie myself up, or even masturbate as a guy or as a sissy. I couldn't even bring girls back to my room, the one time I had tried, I thought he would maybe leave and give me some privacy but he just sat in his bed on his computer and I barely got to second base.

I had made friends with a few people who liked to hang out front of the dorm rooms at a little patio table, talk and smoke cigarettes for hours at a time. We had been doing this for months, having met almost as soon as the semester started. One of the girls name was Rachel, she was kinda infamous around campus for only sleeping with black guys.

We all became good friends often hanging out away from the table and then just before spring break my roommate and I got into a huge fight. Admittedly I used to be a bit of a slob and he was tired of having to ask me to clean my side of the room. It got blown out of proportion and I stormed out. I went to Rachels room and was telling her about it all while she packed to leave for the break. She had plans with her family, they were going to go skiing and she wouldn't be back till the Sunday before classes started back up. I was staying on campus because my family couldn't afford to fly me home for the break and unfortunately so was my roommate. Then I had a crazy idea, what if I stayed in Rachels room while she was gone. Rach had gotten lucky and her roommate had moved out after the first semester and they didn't put anyone in her room for the second. She had the room to herself and if I could convince her to let me stay then I would have it to myself.

I helped her finish packing her things and even helped carry them downstairs to her car. After all of this I thought I might have a chance so I asked her if she would possibly consider letting me crash in her room while she was gone. It would make the next week without all my friends much more bearable if I didn't have to spend it with my roommate. She said shed think about it.

It was the last Friday before spring break, after finishing all my classes for the day I headed over to our table to see my friends one last time before they headed off. One by one they left until it was just Rachel and me at the table. She reached in her pocket and handed me a key. "don't mess up my stuff. And I expect you to wash my sheets and blankets before I get back." She said. "of course." I said, "thank you so much" and I gave her a big hug and then she headed for the parking lot.

I couldn't believe my luck, she had actually gone for it. I went up to my room and grabbed all the stuff I would need, including the small footlocker that had been padlocked closed and under my bed the whole school year. I practically sprinted all the way to her room, sliding the key in the door my heart was racing, I couldn't wait to get dressed up. Once I was inside I started to strip immediately, throwing my boy clothes into the corner where I knew they would stay for the next week. I unlocked my foot locker and opened it up, the smell of lube and silicone filled the air.

I was already hairless, I took time each week to use nair on my body to keep myself hairless. Most people thought I was weird for not having any body hair but a lot of girls actually thought It was sexy and I told them that I did it cause I have always disliked body hair, even my own. I took out my chastity cage and locked my clit up. The key to this lock was in my dorm room, on a keychain in my desk. I started to get dressed putting on my stockings, panties, bra, breastforms, collar, and wig. The feeling of the stocking sliding up my legs sent shivers coursing through my body. It had been months since I had dressed up and I was going to enjoy this thoroughly. As the panties nestled into place I thought I might cum, just from that simple act, I really was pathetic. After I finished putting on my underwear I pulled out a tight fitting dress that was barely long enough to cover my ass and a pair of 3" heels, the same pair that the man who blackmailed me bought me. I put them on and then went to work on my make up. I wasn't the best at makeup but I had gotten good enough to at least do a light layer that made me look a little more feminine. Then I put the wig in place and I was all dressed and ready to go.

I got out my laptop and ran an hdmi cord to the tv and put on some sissy hypno videos I liked to watch. Then I got out some rope and went to work.

So im almost positive I can pinpoint why I am a sissy. At least the steps that led me here. When I was younger I was obsessed with superhero's, hero's always save the damsel in distress, I wanted to play superhero's but I didn't have a damsel to be in distress, so I made myself the damsel and would tie myself up. Eventually this turned into dressing as the damsel when I would tie myself up and then I just wanted to be dressed up and tied up cause I enjoyed it. So over the course of many years I had gotten really good at tying myself up. I could tie myself into inescapable bondage with out help from anyone...I still can. The trick is to have a way to release yourself, like a pair of scissors or a key to a pair of cuffs. I started by putting a ball gag in my mouth and tossing the keys to my favorite pair of handcuffs across the room. Then I tied my ankles together, and then my knees, I tied a rope to my knees wrapped it around the back of my neck and pulled till my knees were almost touching my chin, then I tied the other end of back to my knees. I put my hands together under my knees after a deep breath clicked shut the cuffs around my wrists. The ratchet sound of the handcuffs sealing my fate till I could get back the key.

The feeling of being in bondage and unable to escape until I get the key was a feeling I had missed immensely. I almost came right then, it had been days since I last came. The last time I had gotten to even touch myself was in the bathroom a few days earlier but people had come in so I hadn't even been able to finish. I rolled around on the ground just enjoying the feeling for a bit. After awhile I scooted across the room and fetched my key and unlocked myself. I wanted to cum so bad but had told myself I wasn't going to let myself cum until at least Wednesday, it was Friday now. I didn't know if I could hold out that long but I knew if I could the release would be tremendous.

The next couple of days were more of the same. Only leaving the dorm room to go and get food. By some miracle I had made it to Wednesday without allowing myself to cum. I was practically vibrating I was so horny. I had devised a plan for today that would be a long and difficult scene for myself. First, I of course got dressed. I was wearing the same thing as the days before, unfortunately I did not have a wide variety of sissy clothes at this point. After getting dressed I moved a chair into the middle of the room, I stood on it and attached two pieces of paracord to a pipe inside the tile ceiling dangling in front of the chair and a third piece tied to dangle behind the chair, at the end of one ropes was a spring, attached to the spring was a pair of nipple clamps, not the nice ones with rubber covers but the more intense gator jaw looking ones. Then on the seat of the chair I put my biggest suction cup dildo which was about 9" long. I added a few ropes to make sure it would stay in place. Then to the other paracord I tied my body wand vibrator dangling from the ceiling it was corded so I plugged it into the wall as well. I then got one more piece of paracord and attached a 2.5 pound weight to the end of it. All the pieces were set I just had to get one more thing. I went to the freezer and pulled out a small plastic bowl full of ice that had a string coming out of the surface and if you looked closely in the ice you could see a handcuff key. I tied the block of ice to the paracord dangling behind the chair making sure it was at the right height.

With all of that done I lubed up my dildo and sat myself down on it. I had been working my way up to this size dildo for the past could of days and so I was able to get it in without much difficulties. Once I was fully seated I tied my ankles to the legs of the chairs, I also took the time to tie my calves to the legs as well. Then I raised myself up off the dildo until just an inch or so was left in me. I grabbed the cord with the weight and made sure that while at this height the weight was just barely lifted off the ground and marked the rope. Then retied the nipple clamps to make sure they were just high enough that at full height the spring would be fully decompressed. While at this height I also tied a rope around one thigh, under the chair and too the other thigh. This was to prevent me from standing up high enough that the dildo would come out of me. I lowered myself about halfway down the dildo and retied the vibrator to where the head would be right on top of the head of my cage. Then I reached my hands behind the back of the chair where they would be cuffed and made sure I could reach the block of ice. It was at the perfect height. All the measurements made I was ready to get started.

I put on some sissy hypno audio and had it playing in the room loud enough I could hear it but not crazy loud. I reached down and pulled a ballgag out of my bag and put it on as tight as I could and I put a blindfold on my head but not covering my eyes yet. I looked around one last time to make sure I hadn't forgotten anything. I reached up and turned the vibrator on full blast, I tied the weight off around the base of my cage pulling even tighter on my clit and sissy balls, as I lifted myself up I realized I had tied it a little shorter then I had measured but the insane horniness pent up in me made me keep going without hesitation. As I got up high enough the vibrator hit my cage I almost came on the spot. So many sensations were running through me I had to fight them back so I could get my scene going before I messed up and ruined everything. I reached up and clipped the clamps to both my nipples, wincing as each one bit into my tender flesh. As I lowered myself back down I realized I had underestimated how strong the spring was, once again I ignored everything and pushed on. The only thing on my mind was the need to finish, I lowered the blindfold over my eyes and I reached behind my back and cuffed the handcuffs on my wrists. As the second one locked into place I felt a profound feeling of accomplishment. I had actually done it. I couldn't believe it. In my excitement I had started pressing my cage into the vibrator and was getting very close to cumming. I wanted to stay there and let myself cum but I knew it was much to soon for me to cum. If I came now I would be stuck in the position for at least an hour till the ice melted.

I lowered myself down hard, shoving the dildo into me moaning as it slammed inside of me and crying out as the clamps yanked on my nipples. In reaction to this pain, I jumped up yanking the weight off the ground, my cage being pulled violently and bouncing into the vibrator. I was on a knifes edge, the pain keeping me from cumming and the pleasure pushing further towards the edge. I lowered myself down till the vibrator was resting on my cage and I pushed myself closer to that edge, when I felt I was about to tip over id slam myself down, shoving the dildo inside of me and yanking on my nipples again. I did this over and over, each time getting closer and closer to the tipping point. Then I stopped as I heard a key sliding into the door.

I started to panic. Who the hell was coming into the room Rachel was supposed to be in another state for another 4 days. I tried to be as quite as possible, maybe it hadn't been the door to this room I had heard. The sound of the vibrator and the hypno porn I had playing sounded like it was playing over a PA speaker to me. My breathing had already been ragged from everything I had been doing was coming even more ragged as I fought off a panic attack. The door to the bedroom opened and I heard a female voice say "I hope your decent cause im coming in." followed by silence.

The door swung closed and slammed as the person who had walked in didn't arrest the speed of the door as it did so. I felt like I was about to pass out. I had recognized the voice but it hadn't been Rachel's, "who else would have a key to this room" I thought to myself. Then I heard them start to walk around me. They walked around a few times until they finally said "[real name] is that you" I nodded my head. "did you do this to yourself" I nodded my head again. They reached out and pulled on the nipple clamps which shot a jolt of pain through me and also brought my body back to reality and the pains shooting through me, the pleasures were temporarily gone from shock and embarrassment.

She started to giggle. "Rachel gave me a key to her room and asked me to check in and make sure you weren't destroying the place while she was gone, she also said to make sure you weren't using as a sex lair. I don't think she had this in mind but she is gonna freak when she hears about this."

Hearing her say that I started to struggle and beg though my gag "please dont tell. Please please" of course I was gagged so everything came out as pwweas.

She giggled again "hmm I don't know, I should probably tell her. I mean if I had a sexy little sissy tying herself up in my room id want someone to tell me" when she called me sexy a shiver went up my spine and I started leaking again almost immediately.

"what should I do with you" she mused "should I tell or do I keep you for myself?"

I still couldn't place the voice. I knew I had heard it before but there were so many people as this school that it could have been anyone.

I started squirming again saying "keep me please keep me"

she laughed and walked behind me and took the ice off the string. "ill tell you what" she said "im going to come sit over here and play with myself as you keep doing what you were before I got here and if I cum from watching then ill keep you but if its boring and I don't cum then im going to send Rachel pics and leave you tied up till she tells me what to do. Sound like a fair deal?" she asked. I nodded my head once again in a situation where I couldn't say no.

I heard her lay down on the bed, the idea of having a woman watching me getting me excited again. I start to pump up and down on the dildo. The weight lifts and falls with each thrust pulling on my cage making me shake as it yanks on my sissy balls. Each time I go down my nipples are pulled hard. Im sure they are bleeding at this point. These two pains are fighting a slowly loosing battle with the sensation building from my ass and clit. The dildo and vibrator are driving me crazy, the pleasure renewed and even strengthened by the presence of this mystery woman. The fear of being outed also pushes me on as well as the embarrassment of being caught all of these feeling rushing through me pushing me further and further. Closer and closer to cumming, its been over a week since my last orgasm, ive been edging for the past 5 days. I cant hold on much longer.

I hear her moaning from the bed. Shes panting as im getting closer and closer. On reflex I start begging her to let me cum. She tells me not yet in a panting and breathy voice. I cant hold out any longer im so close to exploding. I beg her again and again before I hear her cry out as she cums loudly. She screams "cum for me" and my entire world comes crashing down.

Im trying my best to hold myself steady so the vibrator is right on my cage, the weight pulling down and the clamps pulling tight. I cant hold on as I hear her yell for me to cum. I let myself cum and my whole body seizes as wave after wave of pleasure rushes through me and out my clit. As im convulsing the vibrator keeps getting pushed away so I slam myself down on the dildo riding it up and down faster and faster as I convulse, cumming over and over, shooting jet after jet of cum into my cage. In my fervor I loose balance and the chair goes sideways. The nipple clamps rip loose of me and I land on my side still cumming with the dildo inside of me.

The fall knocked my blindfold off and I see Anna laying on the bed head thrown back in ecstasy as her orgasm is winding down. she hears the commotion and is snapped out of her trance. She jumps up "oh my god are you ok" she shouts as she rushes towards me. Anna was a friends of Rachels I had met a couple of times going out to do group things like bowling or the movies. We had not interacted with each other very much but I had instantly thought she was cute and had hoped I might get the chance to make a move someday...this is not how I thought that would go.

She asked if I was ok and I nodded. She reached up and took the ball gag out of my mouth. "thank you" I said.

"are you sure you are ok" she asked,

"ya I think so, are my nipples still attached" I reply.

"ya they are still there" she answers with a chuckle.

She starts to untie me and cant seem to get my knots loose. after breaking the ice on the ground to get the key out to unhandcuff me I untie myself.

We sat down in awkward silence not really sure how to proceed. "so do you do this kind of thing often"

"no" I lied she gives me a sideways look and I sigh " I haven't done it in awhile, having a roommate who never leaves makes things like this a little difficult"

She nods in understanding "so you saw Rachel leaving as your chance to be able to have some personal fun time" she says with a laugh

"well honestly not a first. At first it was just to get away from my roommate but once she told me I could my mind immediately realized the opportunity I had" I told her

"please don't tell Rachel about all of this" I beg anna "not only would she kill me but I don't think she'd wanna be my friend anymore."

Anna seemed to consider this then smiled at me "well a deal is a deal and I definitely came before you did, but in the future why don't you come to my room if you want to dress up. I can teach you how to do your makeup and you can teach me all about how to tie people up."

"id like that a lot" I said with a wide smile plastered on my face.

And that is the story of the time I got caught in self-bondage by my friend in college and how it turned into a friends with benefits situation till we both moved away at the end of the school year.