Roommate’s Helping Hand 6: Paying the debt

Part 6: Paying the debt

I was in for a big one. Halfway through our third year in college I lost a bet to my roommate. It was a pretty big bet. And I had been absolutely certain I would win. In fact, I had been so sure that I had agreed to his victory demand without even blinking. And then I lost.

My roommate was very magnanimous. And smug. He told me not to worry about anything. He would choose the clothing, taking my preferences into account, of course. He would come up with the bondage position, taking both of our preferences into account. And then I would have to perform my duty, to provide what he desired most.

The opportunity to perform the deed presented itself very quickly. We both had a free afternoon the next Thursday and we knew that both our other roommates would be having classes until late that evening. That would give us about five hours. Even if we allowed for an hour of preparation and one to clean up, it would mean three hours of bondage.

As soon as I arrived home I found that my roommate already had everything laid out and ready to get the show on the road. He had even come up with a storyline that he would be my babysitter for the afternoon and that he was there to make sure that I would do my “assigned homework” and absolutely nothing else. He had even dressed up already for his role. Seeing him standing in the living room when I walked in stopped me cold in my tracks.

On his feet he had a pair of black leather knee-high boots with three inch heels. In addition he was wearing a pair of grey cotton wool tights that I recognized as coming from my own collection because of the small opening in the front that his penis was sticking through. On top of this he wore a very skimpy purple and black tartan skirt. Traditionally girls wear this with the split and the safety pin holding it together at the side on their hip. He had the split in the front to allow his erection to “split the curtain”, so to say.

On his upper body he was wearing a tight fitting black cotton turtleneck sweater and a short sleeve white blouse on top of it. With his shoulder length hair hanging down loose I thought this guy could be very dangerous at a party with bad lighting and a lot of booze. I asked him how he would have explained his look if one of our other roommates had walked in. He just shrugged and answered that one of the others had already seen him like this once. I was very interested to hear this story but he told me to get to work upholding my end of the bargain.

My roommate told me to go to my room, take off my regular clothes, and put on the stuff he had laid out for me. He also told me to insert my buttplug and he advised me to put in earplugs. I went to my room, got naked, retrieved my plug from my toy box, lubed it and after biting down on a pair of balled up socks I shoved it in my ass. After screwing a pair of yellow foam rubber plugs in my ears, I turned to the stack of clothes lying on my desk.

On top was a pair of red cotton tights. I put them on and pushed my penis through the opening in the crotch panel. Next came my black shoulder length opera gloves and my green wool balaclava. Over this I pulled on a tight fitting grey cotton turtleneck. This has thumb openings at the ends of the sleeves to prevent them from going up. This also very effectively locks the gloves in place. The turtleneck means the balaclava can’t come off easily.

Next I slipped into my black tights with the attached tank top. After pushing my rapidly firming dick through its dedicated opening I pulled the tights up around my upper body until I could slip the wide straps over my shoulders. As a final touch I put on a pair of very thick and soft white cotton tube socks that easily reached to my hips. These are among my most prized sex toys. Because they are heavily ribbed from ankle to hip, walking around with these feels awesome rubbing against my penis.

Having put on all the clothes that had been laid out and sporting a hefty erection I went back to the living room to find out what my roommate had in store for me. He was sitting on the couch slowly stroking his throbbing hard-on. Jumping up he quickly handed me a pair of light brown wool mittens. These put my fingers together in a single pouch and left just my thumbs freedom of movement. The cuffs reached to about halfway my lower arms and the itchy wool felt amazing on my cock.

I was quickly told off by my “nanny” and ordered to put on my black wool turtleneck sweater. This would keep me warm during my long hours of bondage in the chilly apartment. My roommate now pulled a thick white cotton sock over each of my arms up to my shoulders. The many layers meant that my fingers were now completely useless. As a finishing touch I was fitted with a white wool balaclava that went on top of the turtleneck and flared out over my shoulders.

I was allowed a quick peek in the mirror at my black torso and all white appendages. And pink boner. While I was enjoying the view, my roommate moved behind me, pushed my elbows together and started looping a piece of brown rope around my upper arms, just above my elbows, before cinching it off between my arms. This made masturbating impossible and my cock even harder. Another rope was added just below my elbows and one around my wrists.

The babysitter now took a long piece of rope and looped it several times around my upper body and arms, just above my elbows and just below my nipples, before tying it off. Another rope was similarly tied around me but just above my nipples. Holding the middle of another long piece of rope, my roommate pulled this up between my arms and my back until it was right up against the rope that was tied around my body and arms.

On each side each loose end was now cinched once around the two ropes that were tied around my arms and upper body. The loose end on my right was now pulled over my chest and left shoulder and the one on my left went over my right shoulder. The ends were pulled through the ropes tied around my arms and pulled up over my shoulders again with one on each side of my neck. These were pulled around the rope that was above my nipples and were then pulled back over my shoulders where they were pulled very tight and tied off to the ropes around my upper arms. Moving my shoulders and upper arms was impossible now.

All the ropes going over my shoulders also very conveniently kept my white balaclava from coming off. However my roommate decided to take another piece of rope and looped it many times around my neck before carefully tying it off by cinching it at the back of my neck. It didn’t give me any trouble breathing but it made it much more difficult to move my head around. And it looked spectacular as a collar!

My roommate now took another long piece of rope and looped it several times around my waist and lower arms before cinching it off between my arms and my back. One end of another piece of rope was tied to the loops around my waist, to the left of the cinch rope between my wrists and back. The rope was then pulled down between my butt cheeks and then forward between my legs to the right of my testicles and penis. It was then pulled up over my stomach, fed around the ropes around my waist and down between my legs again on the left of my penis. The rope was pulled up between my butt cheeks again and tied off to the right of the cinch knot of my waist rope.

This procedure was repeated twice and gave a really awesome, continuous pressure on my buttplug and created a very conspicuous pouch for my balls. During all this my roommate made sure to touch my dick as often as possible. I had a throbbing erection and the veins really stood out.

After this I was ordered back into my own room so that I could admire myself in the mirror. I was more than happy to do this. My black body and white limbs were now crisscrossed by many lengths of brown rope and I only had very limited movement of my upper body. While I admired every angle I could get into view my roommate retrieved my ballgag with its attached harness from its hiding place. He shoved the big red ball through the opening in the balaclava and into my mouth before buckling the straps behind my head. After tightening the strap under my chin he pulled the remaining harness up over my head and buckled it to the straps already fastened around my head.

After quickly looking me over he muttered something about finishing touches and retrieved a short piece of rope from the living room. He tied one end of this to the bottom of the V of ropes on my chest and the other end to the middle of the rope just below my nipples. This actually made it look like I had boobs now. I definitely had a raging hard-on. Using this convenient handle my roommate pulled me towards his room.

When we got to his room I saw that he had removed the mattress from his bed and that he had placed the bed up on blocks so that it was about three feet above the floor. The bed was a simple metal frame with two inch wide wooden slats fitted from side to side to normally hold the mattress. Between the slats were two inch gaps. The mattress was on the floor underneath the bed.

However, before I would find out why this had all been set up, I would have to pay my debt. Losing meant that I had to give my roommate a hand-job. He informed me that tied up the way I was, I would be able to jerk him off while he was standing behind me. We would be doing this in front of his floor to ceiling mirror. That way he would be able to see everything that happened. To minimize the mess a white nurses apron was tied around my waist. Normally this would be worn on the front but now it covered my ass and the back of my legs. My roommate would shoot his load against this and I would be good for several more hours of fun and play. His erection was quivering from anticipation. Mine was flagging a little.

Grabbing hold of my penis my roommate maneuvered me in front of the mirror with my right side towards it.  Ensuring I was rock-hard again before he let go, he then stepped in line behind me, put his hands on my shoulders and pushed his boner between my hands. With the many layers of fabric over them it didn’t even remotely feel like I was holding another man’s cock in my  hands. Weirdly this really calmed my nerves and I started rubbing and pumping my hands. After a few moments I figured out a rhythm and I could hear my roommate start groaning. In the mirror beside me I could see him slowly pumping his hips in concert with my efforts.  Every now and then he would reach down in front of me and tease my penis back to full, raging hard attention again. Seeing me have an erection while jerking him off made him enjoy himself even more.

After about twenty minutes he grabbed on to my shoulders and told me to jerk as fast as I could. I could feel his body tensing up and just before I thought he was ready to go, I quickly let go. Groaning in frustration my roommate humped the air until he realized what had happened. After all the times he had left me desperate for relief after hours of teasing and tormenting, he now knew what it felt like. Trembling he told me to start pumping again. Very quickly he became hard again and very shortly after that he started bucking and squealing.

And then he had an orgasm. I actually felt something hit the apron stretched over my ass and I stepped forward to let go of my roommates cock. Reaching down, he grabbed hold of my hands and pushed them tight around his penis while still slowly pumping his hips. When every last drop had been pumped out he let go of my hands and removed the apron from around my waist. After quickly wiping of my hands with the soiled apron and telling me to behave myself, he dashed off to the bathroom.

Carefully avoiding the puddle on the floor I used my unsupervised time to admire myself in the mirror some more. I quickly got hard again but before I could find something to hump against my roommate returned. After allowing me to urinate he led me back to his room and told me to stand next to the bed.

He took a length of rope and looped it several times around my thighs, just below my hips before cinching it off between my legs and just below my balls. Again he made sure to accidentally rub and touch my aching erection as much as possible. He now let me sit down on the bed and tied another rope around my legs halfway my thighs, one just above my knees, one just below them, one halfway my lower legs and one around my ankles. He then helped me lay down on my side and put my legs up on the bed before rolling me on my stomach in the middle of the bed.

After very carefully positioning me so that my throbbing boner was sticking down between two of the wooden slats, my roommate grabbed a piece of rope, tied one end around a slat to the left of my waist, pulled it tight over my waist and tied the other end of to right. He tied similar ropes just below my hips, just above my knees and to the ropes around my elbows. These would all keep me securely in place and unable to even buck my hips. While he was playing with me I would not even be able to hump the air in frustration.

My roommate now tied one end of a piece of rope to the one around my wrists and fed the other end through the rope around my ankles. After pulling it very tight he tied it off to my wrists again. He tied another piece of rope around my feet, cinched it between them and pulled the ends through the ropes going from my elbows over my shoulders. Again he pulled them tight and tied them off. I was arched in the most incredible hogtie I had ever been in.

For a few moments he looked me over, admiring his work while stroking and massaging his own penis. I desperately wanted him to stop playing with himself and jerk me off instead. But it would not be that easy. Speaking very clearly, with his mouth close to my head because of the earplugs, my roommate now explained to me that he would spend the afternoon on the mattress under the bed, playing with himself and me.

For the first hour I would be allowed to enjoy my bondage. He would just tease me every now and then to keep my “attention focused” as he put it. The second hour he would play with me fulltime, keeping me as close to the edge as he possibly could. And when I would finally be allowed my big moment, gravity would help him get every last drop where he wanted it. During the third hour I could enjoy the afterglow of my performance while he would enjoy the spoils of his victory. That was the reason he told me to wear earplugs.

Before blindfolding me he laid out the tools he was going to use to insure my continuous and total arousal. These included my old friends, the itchy and scratchy grey wool gloves as well as a vacuum pump. Now he undid the top straps of my head harness and put a thick black wool hairband over my eyes and ears. This very effective blindfold also blocked out even more noise. After re-fastening the straps of the harness, my roommate tied one end of a piece of rope to the D-ring at the top of the harness and fed the other end through the ropes between my feet. After pulling the rope tight and my head up, he tied the rope off.

Now in the most rigorous hogtie I had ever been in, I was desperately horny and fully aware that it would be two hours before I would be allowed to come and another hour before I would be untied. This only made my dick even harder. All I was capable of doing was breathe through my nose. And slightly wiggle my toes. Everything else was kept under control by one or more pieces of rope. For someone whose main interest was sperm my roommate sure as hell knew how to keep his supplier happy.

Being in my own little cocoon I had absolutely no sense of time. I didn’t know whether two minutes had passed or an hour. At completely random intervals my roommate would do something to give me a quivering erection before backing off again. Every time he did this I thought my first hour was up and that it would only be one more hour until I would be allowed to shoot my load. But then he would simply let go again. His favorite technique was ever so slightly rubbing a finger covered with scratchy wool over and around my cock. This light touch just drove me nuts but the only thing I could do was moan and groan in my gag. Maybe not letting him come when he wanted to hadn’t been such a good idea after all.

With all my senses muffled my only connection to the outside world was my penis. And then something was slipped over it. I couldn’t figure out what it was until it felt like my dick was actually being sucked further into it. My roommate had put the vacuum pump on me. And he just kept pumping. This was mind blowing. Nothing was touching me but I had a painfully hard boner. Without any chance of having an orgasm I could be kept like this for minutes on end.

All of a sudden the pump was removed and a pair of hands covered in itchy wool grabbed my cock and started massaging, rubbing, stroking and jerking me. Now I was going nuts because every part of my dick was being touched and teased. And still I wasn’t allowed to come. And then the pump was applied again. But then I was tormented with the gloves again. My roommate kept switching between these two methods. One moment my cock was literally in a vacuum feeling like it would explode and the next it was sensory overload with the rough wool on my most sensitive member.

During one of the itchy and scratchy sessions my roommate slowly pulled back my foreskin. I knew for certain that this was because he was about to let me come. But no, this was just so could rub those damn gloves over every little bit of my now exposed tip. Later that night my roommate told me just before he teased back my foreskin, I had started oozing pre-cum. He had never seen anyone do that before but he was very proud that he had made it happen.

When my tip had been fully exposed and fondled the pump was used again. I was pumped up until I as was quivering, throbbing and totally desperate again. My roommate later swore my dick was half an inch longer inside that pump. And that with practice I could get another half inch. He was of course more than willing to train me.

My roommate was now very slowly running two fingers up and down the entire length of my shaft. Then he also started rubbing one itchy wool finger over my exposed tip. Strictly hogtied, I was squealing like a piglet. Now that I was good and desperate he grabbed me with one hand and started slowly pumping me, very slowly building up the speed of his strokes.

This felt spectacularly good. I wasn’t allowed to come yet but I was getting into a rhythm. He kept jerking me faster and faster and gripping me tight. Finally I started feeling the pressure build up down in my groin. The sensation of feeling my sperm moving down my penis and squirting out the end was spectacular. I even blacked out a little.

Shuddering through my orgasm and the aftershocks I actually hoped I had given my roommate a black eye or something. Very carefully he pumped and stroked every last drop out of me. This felt just as good as the actual orgasm.

The next hour I just enjoyed the rigorous bondage and the orgasm afterglow. Life was good in my little cocoon. During this time I heard some vague noises that I assumed to be my roommate. My daydreaming was rudely interrupted when the ropes tying my to the bed were removed. I was rolled to the side of the bed, pushed up in a sitting position and my legs were untied. My roommate helped me get up and steered me to the bathroom. My legs were very wobbly.

In the bathroom I was sat down on the toilet and left there for a while. Because of the way my arms were tied up I found that the most comfortable way to sit was with my legs spread, my upper body leaning forward and my head tilted back. I just relaxed and peed. Later, after he had untied me, my roommate told me he had been very turned on by my pose and had seriously considered asking me to give him a blowjob. In the end he had decided not to jeopardize his regular supply of sperm.

After being untied I staggered over to my room to remove the many layers of my outfit. I desperately needed a shower. That evening I was sore all over but in a very good way. My roommate confessed himself very happy with the afternoons proceedings. I had jerked him off and then oozed pre-cum on him before splattering a full load of sperm directly in his face.

When did I want to go again?

03.08.13