Roommate’s Helping Hand 5: Playing the odds

Part 5: Playing the odds

I was in for a big one. At the end of our third year in college my three roommates and I decided to go to Vegas for a weekend. In the run-up to the weekend some dealing had taken place. My roommate and I had made a bet about something unimportant. He had been so sure that he would win that he told me I could name whatever I wanted because he wouldn’t have to do it anyway. Except that he lost. I decided that I wanted to spend a full night in strict bondage at the next possible opportunity.

My other roommates had each approached me separately about the rooming arrangements. They were a little unsure about rooming with the choirboy. After Oscar winning acting performances on my part each of them paid me $100 to “volunteer” as his roommate. Off course I didn’t tell him this. I merely informed him that after complicated negotiations I had been able to give him the chance to pay his debt.

Since we would be driving there I could pack my bag with all the goodies I wanted to bring. Had we been flying I would never have dared to put it through the security checks. We arrived at the hotel just after one in the afternoon. While the others took care of the checking in, I parked the car. When I got to the reception area I was informed that there had been a small mix-up. We had been given two rooms on different floors, in different wings. Excellent! We wouldn’t be disturbed. And one room was a twin and the other a double. I began to see the point. After our friends gave each of us $100, the choirboy and I agreed to take the double.

During the afternoon I did some sightseeing and after dinner my roommate went to see a show and I went to the casino with the others. We hit the slot machines first and then went to the blackjack tables. Pretty much everything we tried paid off. We were on a roll. At about ten they wanted to join the poker games. I didn’t. My roommate and I had agreed to meet back at the room at eleven. I watched the game for about half an hour before heading back up.

When I arrived about ten minutes early, my roommate wasn’t there yet. Deciding not to waste any time, I took off all my clothes and started preparing for my big night in Vegas. After picking up my buttplug out of my suitcase, I went to the bathroom, lubed it up, and biting down on a small towel I worked the five inch toy into my rectum. As the wider part slipped through my sphincter muscles I heard my roommate come into the room. After I heard him close the door, I stepped out of the bathroom and informed him he was just in time to enjoy the show. He quickly sat down on the couch and told me to get to it.

From the suitcase I pulled a stack of clothes and threw it on the bed. First, I put on my army green, wool balaclava and then pulled on my white opera gloves. On top of these I put on a tight fitting, cotton turtleneck sweater that reached to just above my now firming up penis. Next I put on a condom and after this I slipped into a pair of white cotton tights. After pushing my cock through the opening in the crotch panel I pulled the tights all the way up to my ribcage, on top of the sweater. In the mirror over the desk I admired my white body and limbs, green head and pink erection. The condom would prevent any accidents during the night from ruining my outfit.

On top of this I pulled a very stretchy, purple leotard. After stepping into the neck opening I pulled it up around my legs and body and put my arms in the short sleeves. It had a reasonably conservative cut to the crotch panel. My cock would not accidentally slip out during the night. I took great care to position my penis so that it pointed straight up over my stomach.

At this point my roommate had a hand down the front of his pants and a very red face. He probably regretted wearing tight jeans that night.

From the bed I picked up my karada rope that I had prepared at home. I put my head through the loop at the top and let the rest hang down my front. There were four evenly spaced knots in it with the top one just above the height of my nipples and the lowest one just above my bellybutton. From this two long loose ends dangled down. I fed the loose ends back between my legs making sure that one was positioned on either side of my cock and both were over my buttplug in between my ass cheeks. Pulling them up my back I fed both ends through the loop around my neck and let them dangle down to the ground.

After that I pulled one end down through my left armpit and the other through my right. Pulling them around to my front I fed each through the ropes between the top two knots and then out and around my back again. Here I crossed the ropes, led one around each side to the front again, fed them through the pieces of rope between the middle knots, back out again and crossing them behind my back again before pulling them around my front and feeding them through the ropes between the two lowest knots. One final time I pulled the ends around my back again where I tied them off to the ropes that went up from between my legs to the noose around my neck.

Admiring my work in the mirror I was very pleased with myself. My upper body was crisscrossed with brown rope and the rope on either side of my cock pulled the fabric of my leotard really tight over it. Now my cock really wouldn’t slip out during the night. As a final touch I looped a piece of rope around my waist a few times and tied it off to the karada rope going down my back. I repeated this with another piece of rope around the bottom of my ribcage. These didn’t restrict me in any way. It just looked awesome and fit in nicely with my plan to have as much rope as possible encircling my body and adding to my feeling of being tied up.

I just needed a few more items to complete my outfit. From my suitcase I took my thick, black wool, thigh high socks and pulled them on my legs. My erection really strained against the material holding it in position. It proved to be a very good test because it couldn’t slip out. Next I picked up a pair of thick black cotton knee socks and pulled one over each arm all the way up to my shoulders. The tight fabric meant that my hands were automatically balled into fists. From now on, I had no more use for my fingers.

With a white body, purple leotard, black arms and legs, a green head and lots of brown rope encircling me, my roommate informed me I was a fashion disaster. I told him that what was inside counted the most. Staring at the lump pointing up towards my bellybutton he had to agree with that.

It was now time for my roommate to start tying me up for the night. I folded my arms behind my back so I had my hands on the opposite elbow and my upper arms were against the side of my body. My roommate then took a long piece of rope, looped it around my arms and my upper body, just above my nipples, many times and then tied the ends  to the rope behind my back. Then he cinched the rope between my arm and my torso on each side. He repeated this with another rope just below my ”boobs”.

With my upper arms immobilized he turned his attention to my lower arms. He pushed both my hands up until my wrists were crossed between my shoulder blades. Then he took a piece of rope and looped and cinched it around my wrists and the karada behind my back. He then finished it off with a rope tied to my wrists and looped around my upper arms and chest.

As a finishing touch my roommate tied one end of a piece of rope around my left arm, just above my elbow. He then fed the other end between my back and forearms and tied it off just above the elbow of my right arm. This pulled my elbows slightly in to my body and behind my back but was not too tight. The idea, off course, was to create very restrictive bondage that I would be able to endure all night.

After this I admired myself from all angles in the mirror. I was very pleased with the way I looked and felt. Perfection achieved! After I expressed my satisfaction, I walked over to my side of the bed and sat down. My roommate then looped a piece of rope around my thighs and cinched it off between them just below my balls. He then tied one just above my knees and for good measure another one halfway in between them. Next he looped and cinched a rope around my legs just below my knees and one around my ankles. Then he added another three in between them at regular intervals.

To my surprise he then added even more rope to my bondage. He looped and cinched a rope around my feet, just forward of my heels and another one just behind my toes. Very thoughtfully he tied ropes from the ties around my feet to the rope around my ankles to make sure they wouldn’t slip off during the night. I was really impressed.

My roommate now undid the zip of his jeans and pulled out his erection. After I asked him what he intended to do with that he explained to me that after he had finished tying me up he was going to jerk off while looking at me squirming around on the bed. That was fine with me.

Now came the time to add the final pieces of my bondage and the newest additions to my collection of feel-good items. The first was a thick and stretchy black band that fit snug around my head from just above my mouth to well above my eyebrows. In the front of it was a hole that fitted around my nose. Truly the best blindfold I had ever seen or experienced.

And last but not least, my gag. I had only recently taken delivery of this big, red ballgag with a full headharness. My roommate pushed it through the opening in my balaclava and into my mouth. It just fit perfectly. I couldn’t move my tongue and my mouth was pushed open as far as I could take it without getting muscle cramp. My roommate pulled the main strap around my head and buckled it tight. He then did the strap under my chin before pulling the top strap over my face and blindfold, over the top of my head and then led both ends down on either side of my head where he buckled them to the main strap around my head.

My roommate then helped me lay down on the bed and asked if I was comfortable. I just nodded and started exploring the limits of my restriction. Lying on my back, I just felt too much pressure on my arms and would be unable to sleep. I could roll on my stomach but rolling over again was very difficult. Lying on my side I was reasonably comfortable and after a while I started dozing off. Uninterrupted sleep was not possible. It was pretty much like it is on an airplane. You fall asleep for a short time and then wake up very aware of your surroundings. Except I had never woken up on a plane in strict bondage, with a gag in my mouth and a dildo up my ass. All kinds of crazy fantasies kept flashing through my mind.

After a fitful sleep I woke up once more because my roommate was moving around on the bed. I had the distinct impression that he was humping his pillow. Feeling and hearing him play with himself was a bizarre experience. I would be the first to admit that our relationship was nowhere near what would be considered normal in any way, but this took the cake.

That’s when I decided to take another gamble. With some effort I managed to roll on my stomach and I started slowly humping and grinding the mattress. With my dick pointing upwards over my lower belly I immediately got hard. I also knew that I would never be able to make myself come this way. Then I noticed that my roommate had stopped playing with himself. After that I felt him pulling the sheets off the bed.

Pretending not to notice anything I continued rubbing my erection on the bed. I figured I had a fifty percent chance that my roommate would not be able to control himself and would jerk me off. I had deliberately left this out of the scenario just to see what would happen. Soon after, he put a hand on my shoulder and I was informed that it was just after 6:30 AM. I had spent the night bound, gagged and plugged.

My roommate rolled me over on my back and said he wanted to ask something from me. He was very sorry. He knew it wasn’t part of the deal but he really, really wanted my sperm. He promised he would tie me up again for another night to make up for it. That was even better than I had hoped! As I appeared to think it over he started rubbing and stroking my penis, running his finger along the length of my shaft and over and around the tip. This made me really hard.

Grabbing hold of my erection with one hand through the fabric covering it my roommate repeated the question. After I nodded my consent he informed me the normal rules would apply. He would play with me for an hour before allowing me to shoot my load. Then he would play with himself for half an hour before untying me. This wouldn’t be as easy as I had hoped it would be.

While continuing to rub, tease and play with my cock through the fabric my roommate started slowly pulling the crotch panel of my leotard to one side. First he just pulled it off my balls. My shaft was still caught under the tight spandex but my balls were only covered by the cotton tights. Now he started slowly rubbing my balls and massaging the base of my cock. Holy shit!

With my dick still stuck underneath the leotard my roommate started slowly stroking my cock, moving further and further to the tip. While doing this he also kept peeling back the leotard to expose more and more of my throbbing boner. When only my tip was still held under the stretchy fabric he let go of me and then flicked the leotard off.

My raging hard-on was finally released and was pointing straight at the ceiling. I was desperate for an orgasm but I had the sneaking suspicion that less than five minutes had passed since my roommate had gotten started on me. He quickly peeled off my condom, grabbed my cock with both his hands and started slowly stroking my shaft. This would get me nowhere near an orgasm but would just make me harder and hornier.

For what felt like ages he continued rubbing, squeezing, jerking, teasing and stroking me. I was going nuts and spending a lot of time humping the air. Then with one swift movement he pulled my foreskin down. Pumping my cock with one hand he ran the fingertips of his other hand around the edge of my tip and the opening of my urine tube. Electric shocks were going through my body again. And then he simply let go.

While I thought I could feel him climb off the bed I continued bucking and thrusting my hips, but to no avail. I then felt something being draped over me and I realized my roommate had covered me with two sheets so that only my penis stuck out from between them. He climbed back on the bed, sat down on his knees on my right side, placed his left hand on my stomach and with his right hand very slowly started pumping my throbbing boner. With each stroke he moved his hand from the tip all the way down to the base of my shaft. And then all the way back up again. And then down again. He just kept repeating this motion over and over, driving me nuts.

Little by little, he kept upping the pace until he was properly jerking me off. And finally I was allowed to come. I groaned in my gag, my whole body was spasming. And I could feel my sperm shoot all the way through my cock and then explode out of the tip. My roommate later confirmed it flew higher than his head. He had been very impressed. Meanwhile, he kept pumping me and my remaining sperm just gushed down my penis and over his hand. Using one of the sheets my roommate wiped up all of my juice, toweled of my penis and stuck my now limp member back under my leotard.

As I slowly started getting back to my senses I could feel my roommate moving around on the bed as if he was climbing up on something. When he finally was in position I heard him start groaning. After a short while I felt the bed starting to move rhythmically in tune with his ragged breathing. And then I heard his cum squirting out while he squealed with delight.

He later told me had propped himself up against the wall with his ass and feet while laying on his back. He had then jerked off with the tip of his cock only inches away from his own face. And he had shot his load into his own mouth.

My roommate climbed off the bed and went to the bathroom. I just continued to luxuriate in my bondage. Not that I had much choice. I felt exactly like I did all night. Totally unable to move. And immensely satisfied, as well. After a while I felt a hand on my foot and then all the ropes around my legs were untied. I was helped up in a sitting position, my feet were guided to the floor and then I was made to stand up. I was very shaky and wobbly but with guidance I was able to make it into the bathroom.

Once there, my roommate slipped my penis out of my leotard again but instead of sitting me down on the toilet he said he had aimed me at the stand up urinal. He just thought I didn’t want to sit down with the plug still in my ass. Emptying my bladder felt so good, even though another guy was holding my cock. But, in fairness, I had never felt bad after he had my dick in his hands.

Having put my penis in the leotard again, my roommate moved behind me, where I could feel him untying the ropes around my wrists and arms. After they were untied, my arms just hung down my sides, completely limp. Feeling only returned slowly. My roommate then informed me that I would have to do the rest of my undressing myself. He told me to take my time and have a nice, long, hot shower afterwards. He would be in the room. Apparently he wanted to spend some more time with one of the sheets that was covered with my semen.

With difficulty I managed to peel the socks of my arms and then undo the harness around my head. After working the ballgag out of my mouth I took of my blindfold and stood blinking in the light. As soon as the purple elephants and green stars started fading to the background I drank a bottle of water and worked my jaw back in to motion. Afterwards I untied my karada and took off all the clothes. Next, I gingerly removed my buttplug, used the sit-down toilet and took a scalding hot shower, trying to work the muscle ache out of my shoulders, arms and back.

It had been one hell of a night. Later, when leaving the room to check out, I cast a look behind me and couldn’t help wondering what CSI would make from the bed. We met our other roommates in the lobby. They were hung-over and broke. As soon as I had left, they started losing. I informed them I had been drained dry too.

I just felt like the big winner for the weekend. I made $650 playing blackjack, I had gotten $80 out of a slot machine and my roommates had paid me $300 only to facilitate what I wanted to do anyway. But those were just details. The big prize was that I had spent more than eight hours very strictly tied up, gagged, blindfolded and buttplugged. I had been given a truly mind-blowing orgasm and I had an IOU for another session. And I had a lot of spending money for some new toys and clothes.

When one of my roommates said that this weekend had been the ultimate male-bonding experience I couldn’t help smiling.

18.02.12