Roommate’s Helping Hand 2

Part 2

Hi there, it’s Tommy again. After discovering me in self bondage my roommate had offered to help me if I wanted him to. Some time went by before the subject came up again. He asked me once and I said I was still thinking about it. In addition at least one of our other roommates was in the house as well most of the time making the whole thing impossible. Then both of them left on Friday afternoon for the winter holidays giving my roommate and me a “free” night before I was going to leave on Saturday.

We talked about it and I agreed to let him jerk me off. Turns out jerking guys off turns him on and playing with the sperm afterwards really helps him get off. As being tied up is what gets me going I didn’t really think I was the one to judge. We also laid down the rules and the conditions. I would decide how I wanted to be dressed and would talk him through the process of tying me up. He would then gag me and leave me in a strict hogtie for half an hour before untying the hogtie again, rolling me on my back and playing with my dick as long as he wanted before making me cum. That was the part I wasn’t going to have any influence over. He would only touch my penis with his hands and no other sexual acts would take place. He would then leave me tied up and go to his room to have his fun. He would then return after no more than an hour to untie me. He also asked me if he could watch me dress up. Considering what was going to happen afterwards I didn’t really mind.

I then set out to prepare for the night. First I printed a few pictures of girls tied up the way I wanted to be. I numbered them and added notes about the correct order of applying the ropes. Also the heating system in our apartment always valiantly tried to keep the place comfortable but wasn’t completely up to the challenge in the middle of winter. I therefore decided to put on more clothes than usual as I was going to spend a long period lying still.

But first I put in my butt plug. This was the one thing I didn’t want to do in front of an audience so I went to the bathroom, bit down on a towel and worked in the plug. After getting back to my room I started by putting on a pair of black wool tights. These had a small opening cut in the crotch panel that I could stick my penis through. Growing up in the snow belt I had learned how to get my kicks in relative comfort. Next came a thin, black, ribbed cotton turtleneck sweater and then I pulled my black, shoulder length opera gloves over the sleeves. My roommate then commented that I only needed a balaclava to complete the full body catsuit look.

This sounded like a very good idea and after a little searching in my closet I found two black wool balaclavas. Again, living in the snow belt had thought me that frostbite wasn’t something to joke about. I pulled one balaclava over my head and threw the other on the chair before walking over to my mirror to admire myself. Only my eyes, mouth and cock weren’t covered in black fabric. I really liked what I saw. My roommate then warned me not to play with myself. That was his job.

I quickly continued the dressing up. Now I pulled on a pair of white cotton socks that reach to just over my knees. This caused me to have a very big erection. Seeing a girl in knee socks or wearing them myself gets me rock hard in seconds. Next I put on a pleated red skirt that reached to just below my ass cheeks. The tent pole in the front gave a very nice effect. To complete the costume I put on a white, short sleeve blouse.

For a few moments I admired myself in the mirror. It looked stunning! White lower legs, black thighs, red skirt, white blouse and black arms and head. In profile my erection looked very satisfying. I turned to my roommate and asked him if after tying my arms behind my back and gagging me, he would let me look at myself in the mirror before putting me in the hogtie. He said he would be happy to as I would no longer be able to play with myself then.

I turned my back to him and put my arms behind my back as close as I could get them. He picked up a piece of rope and looped it around my arms, just above my elbows. After he had pulled the rope tight and cinched it between my arms I could just feel my elbows touching. He then tied and cinched another rope around and between my wrists and another one halfway my upper arms. I quickly admired his work in the mirror and the white rope on the black gloves looked awesome.

After this I explained to him how to tie one end of a piece of rope to the rope between my elbows, pull it under my left armpit, over my chest and back over my right shoulder before tying the other end to the rope between my elbows again. He then repeated the process on the other side. As these ropes were black it gave a very interesting effect on top of my white blouse.

Having seen my reaction to my knee socks my roommate suggested using another sock in my bondage. This really got my attention. He picked up a long, very stretchy white tube sock and started pulling it up around my bound arms. This was very tight and reached to the rope around my elbows. It looked and felt staggeringly awesome! I couldn’t use my fingers anymore and it looked just like a monoglove. After that my roommate looped and tied a long piece of rope around my upper arms and chest and then another around my lower arms and waist. These were black and looked magnificent on top of the white blouse and white monoglove sock.

My roommate now held up my black ballgag. He pushed it through the opening in the balaclava and into my mouth and he thoroughly tightened the straps behind my head and under my chin. He then told me I had two minutes to look in the mirror. It looked awesome! My shoulders were being pulled back and my arms were pulled tightly together. The black balaclava with the black leather straps over it and the black rubber ball visible through the opening looked just as beautiful as the white tube sock monoglove. Looking at myself in profile really blew my mind. My arms and shoulders were being pulled back as far as possible and my cock was sticking forward at full attention.

My roommate then helped by pulling my skirt up in the front and pushing it under the rope around my waist. This made the perfect picture. In the back the red skirt hung down with my white bound hands pulled down on top of it and in front my throbbing penis was sticking out from my black tights in full view. I turned around a few times in front of the mirror to admire myself. Now my roommate surprised me again. While I was looking over my shoulder to have a good look at my bound arms in the mirror, he firmly grabbed my cock with his right hand and pulled me towards the bed. Still holding on to my dick he steered me around until the back of my legs touched the bed and then pushed me on the bed while maintaining his grip. We hadn’t talked about this but I wasn’t going to complain.

He now got down on his knees and looped a piece of rope around my legs, halfway up my thighs. After tightening and cinching it between my legs he tied another rope just above my knees, one just below my knees, one halfway my lower legs and one around my ankles. It felt even better than it looked in the picture I had printed.

Now he helped me lie down on my side before rolling me on my front. He then tied a piece of rope to the one around my ankles and pulled my feet up to my butt. He fed the rope through the ropes going from my elbows over my shoulders and pulled the end back to my ankles again. He pulled the slack out of it and asked if it was tight enough. I shook my head very hard and he pulled it tighter. When this still wasn’t enough for me he pulled it as far as he could and then tied it off to my ankles. My knees and shoulders were now pulled up from the bed and all I was capable of doing was breathing, blinking my eyes and wiggling my toes. In other words, for the first time in my life I was tied up the way I wanted to be. Total perfection achieved! I then heard my roommate say he would be back in thirty minutes and half-jokingly warning me not to go anywhere.

Testing my bonds and really enjoying my inability to move I completely lost track of time and my roommate scared the crap out of me when he cleared his throat to let me know he was back. First he removed the ropes between my elbows and ankles. He pushed my feet back down on the bed and then rolled me on my back to get access to my penis. He bunched up the duvet I was lying on and pushed it under the sides of my torso and under my shoulders. This way I could lie on my back without my full weight pressing down on my arms. He also put my pillow under my head and a cushion under my knees. Considering I was bound, gagged and butt plugged I still felt very comfortable.

I noticed my roommate had once again dressed up for the occasion. He was wearing black high heel shoes with straps over his feet and around his ankles on top of a pair of flaming red thick cotton socks that reached to halfway his thighs. In addition he was wearing a very short grey skirt, a white blouse and a small black cardigan. He wasn’t wearing any underwear. With him standing next to the bed I could see his dick was pushing up his skirt too. When he turned around and bent over to pick something up I noticed a black knob sticking out of his ass. He had butt plugged himself as well.

When he turned around again he was holding a pair of white tube socks in his hands. He then informed me that having seen my response to socks he was going to use these to make it even more enjoyable for me and then pulled one sock over each hand. My cock didn’t spring to attention but definitely firmed up a little. Grinning at me he sat down next to me and started rubbing, massaging and teasing my cock. Within minutes I had a quivering, throbbing and rock hard erection.

Naturally I would not be allowed to get off easily and he continued his work for what felt like hours keeping me fully erect but nowhere close to an orgasm. When he briefly let go I noticed on my alarm clock that only fifteen minutes had passed. I then saw him pick something else up from beside the bed. It was a pair of grey wool gloves. Very rough, very itchy, very scratchy grey wool gloves. I had always enjoyed the feeling of fabric on my dick. wearing socks over my hands while playing with myself or putting my penis in a tube sock while jerking off. These gloves looked much more intense!

My roommate put on the gloves and very lightly rubbed them over my cock. Even that light touch made me so hard it hurt. He then held me only between the thumb and index finger of his left hand and very, very slowly pulled back my foreskin. As the head of my penis became visible he started rubbing the tip of the thumb of his right hand over it. If the wool felt rough on the outer skin of my penis it was nothing compared to the feeling of it on my most sensitive body part. I literally felt electric shocks go down my spine. My whole body was spasming and I squealed and groaned in my gag.

While that all happened my roommate kept very slowly but steadily pulling back my foreskin until it slipped off the head of my cock with an audible snap. And he kept rubbing the fingertips of his right hand over my soaking wet tip. He now had my cock firmly gripped with his left hand and ran the fingers of his right hand around the rim, over the opening of my urine tube and the bottom of my head just above the foreskin while still wearing those scratchy wool gloves. I was nowhere near an orgasm but I was still spasming and groaning without control.

Long after I thought I had lost control, he continued massaging and rubbing my tip with his right hand and now started stroking and jerking my shaft with his left hand. Turns out there was another level to my loosing control. I was getting close to having an orgasm now though. But every time it happened he would simply let go of me. And being tied up the way I was I couldn’t even convincingly hump the air.

I had now reached the point where I was groaning and spasming even if he wasn’t playing with my cock. He had once again let go of my dick without letting me cum and got up from the bed. I saw him walk over to the chair and pick up the other balaclava. He turned to me and told me he was going to borrow the balaclava from me and use it to catch all my sperm. If I would be allowed to come I couldn’t care less what he wanted to use. After walking back to the bed he rolled me on my side and pulled me as close to the edge as possible. While standing next to the bed he then spent several minutes rubbing, teasing and massaging my tip and jerking and stroking my dick wearing those excruciatingly awesome gloves until I was once again spasming and groaning.

When he pulled his hands away to once more prevent me from coming he picked up the balaclava again and showed me what he was going to do. He put both his hands in it through the neck opening with the openings for the eyes and mouth facing up. Then he pushed the balaclava up around my cock letting it stick through the mouth opening. Once again he started rubbing, teasing and stroking me. I was rock hard in seconds. And moaning continuously. After a few more minutes he started rhythmically pumping and jerking my cock. Finally I was allowed to come. It burst out of me. I was convinced I had shot straight through the balaclava. He kept pumping and massaging my dick for several more minutes trying to get every last drop out of it. For me it felt extremely satisfying.

After he was convinced he had gotten everything he very carefully pulled the balaclava off my now limp penis and asked if I was okay. I nodded a little shaky but felt awesome. He wanted to know if I wanted to remain tied up as agreed before. I nodded once more. Then he sped out of my room cradling the balaclava in his hands. I heard his door close and every now and then I thought I heard something but had no idea what was going on. I later found out he had simply pulled the cum soaked balaclava over his head and gone nuts in his own bed.

After the agreed hour my roommate returned. His hair was on end, his cheeks were flushed and he had a huge grin on his face. After he asked if I wanted to be untied I quickly nodded my head. I had spent more than two and a half hours in strict bondage with my elbows touching and I was very sore. He untied my arms and then asked me if I wouldn’t mind doing the rest myself. I shook my head and then he asked me if he could keep the balaclava for a few more days. I nodded again and he shot out of my room. I heard the door to his room slam shut before I had even managed to push myself up on my elbows. I didn’t see him again until after the holidays. After untying and undressing myself I took a long shower. When I walked back to my room I still heard some indistinct noises coming from my roommates bedroom. I slept extremely well that night. The next day I left to pick up my sister from the train station and we then drove on to our parents for the holidays.

After the holidays my roommate gave me a brand new army green balaclava. Apparently he had so much enjoyed himself with my previous one it was now beyond repair. In addition he gave me those scratchy grey wool gloves and a pair of hip high socks with wide pink and purple horizontal bands. I’m not the most fashion conscious person in the world but even I thought that combination clashed horribly. Didn’t stop me from putting all that stuff on that night and jerking off in front off the mirror though.

02.04.10