Roommate’s Helping Hand

I’m Tommy. This is a story of how I once was discovered playing with myself. It was during my third year of college. I was living in an off-campus four-bedroom apartment with three other guys. The parties were great and the privacy of our own rooms was ruthlessly enforced. Quality alone time was a big part of my entertainment and stress relief.

One Sunday morning I awoke with the urge. I had abstained of masturbating and bondage for eleven days. Two of my roommates were gone to see their family and the third had just left for his choir practice. I had some breakfast, took a quick shower and was ready to go. Still naked from my shower I walked back to my room and pulled all the stuff I wanted to use out off their hiding places.

I have two fetishes: bondage and schoolgirl uniforms. I was going to dress up before I would tie myself up. I started with a pair of white tube socks that reached to halfway my thighs. This alone was enough to give me a massive erection. Next I slipped on a very short, pleated pink skirt. It doesn’t even completely cover my ass cheeks. After this I pulled on a pair of rough cotton, black opera gloves. Jerking off with these afterwards was going to feel awesome. Next I put on my white, long sleeve blouse. I finished off the outfit with a thin, knitted black V-neck sweater, making sure that the collar and the sleeves off the blouse were sticking out from underneath it just the right way.

Admiring myself in the mirror I could barely control myself so I quickly got on with the bondage. I started with my black rubber ballgag, working it in and pulling the straps tight behind my head. Next I picked up my butt plug. It’s a five inch long, one inch wide shaft followed by a narrower part and ends in a flared out knob. This means it can’t go all the way in or be pushed out. The pressure on my sphincter and the feeling on my prostate is brilliant.

Now I set up my release. I always hang a pair of scissors on a piece rope from my desk. This way they hang just above the ground within easy reach. As soon as I get there first of course. I also have a knife on the bottom of the waste paper basket next to the door.

Now came the proper bondage. I started with a piece of rope I have spliced into one big loop. I pulled this around my upper body like a hoolahoop, pulling it tight against my back with the loose end hanging down the front. I crossed the ropes coming along each side off my chest in front of me and pulled the resulting loop over my head, shoulders and arms again. I now crossed the ropes going behind my back again, making another loop and put my arms through it so it looked like I was wearing a backpack. The rope went from the crossing behind my back, under one armpit, over my shoulder and around the back of my neck over the other shoulder, down through the armpit and back to the crossing again. Getting the size of the big loop right had taken several weeks of testing.

Next I sat down on my bed and looped a piece of rope several times around my legs above my knees before cinching it off between my legs. I did the same below my knees and around my ankles. To the cinch rope between my ankles I tied another piece of rope with a cinch noose at the end of it. Now I stood up again and picked up a long leather belt. It’s about one inch wide and it’s one of several I found in a big travelling trunk in my grandmothers house. I wrapped it twice around my waist and buckled it so it was reasonably tight around my waist.

Still standing I reached behind my back for the rope where it crossed behind my back. I pulled the rope that went under my left armpit until there was a loop big enough to put my right arm through it. With my left hand I pulled all the slack out off the rope going under my right armpit (and the loops around my chest and other arm) until there was a loop big enough to put my left arm through. This is the trickiest part of my bondage. With my arms through the loops my elbows are kept close together behind my back and with a little movement of my shoulders the little slack that’s still in the rope is evenly distributed. The only way to get out of this is by pulling the rope over my shoulders down. I always do this by catching it behind a doorknob.

But right now I was going to complete my bondage. I slowly sat down on my bed and rolled on my front. I pushed my arms between the belt around my waist and my back until my hands were through. I then bent my legs until my feet were as close to my butt as I could get them. I had to swing them around a little until I managed to catch the rope hanging from my ankles. I did a quick check of my escape methods and then I pushed my hands through the cinch noose and pulled the slack out of it.

It was magnificent! I was strictly tied up, dressed like a schoolgirl and rolling on my side and looking in the mirror next to the door I could see my throbbing erection poke out from underneath my skirt. I rolled back on my stomach and slowly started humping on the bed. Tied up like this I am unable to make myself come but it just adds to the excitement.

About fifteen minutes later I heard the front door open and my roommate yelling he was back early because practise had been cancelled. I then heard him walking nearer to my room and asking me if I wanted to watch a movie with him. While he was saying this he banged on the door three times. On the second knock the door burst open. The lock had been dodgy ever since I moved in but it had never gotten me into trouble before.

We were probably equally surprised. I instinctively rolled on my side and tried to make myself as small as possible. As he slowly walked into the room I realised that this had completely exposed my penis sticking out from underneath my skirt, although my erection went down pretty quickly. As I tried to roll back on my front I heard my roommate ask if I had done this myself. I grunted something and nodded my head. I then heard him say that this was really impressive which kind of took me by surprise.

He then got down on his knees beside my bed so his head was about level with mine. He then asked me if he could, Please, jerk me off. I was totally amazed by this question. In response to my bewildered expression he explained he didn’t want to have sex with me, I would not have to perform any sexual act for him and the only part of my body he wanted to touch was my dick. Not being in a very strong bargaining position I briefly thought about it and decided to agree. Who knew what he would do if I didn’t?

After my short nod he jumped up and said he would dress up appropriately for the occasion and would be back in a few minutes. After he left I rolled back on my stomach and briefly thought about making an attempt to reach the scissors. But tied up the way I was getting down from the bed and over to my desk was probably going to take a good fifteen to twenty minutes.

After about five minutes he walked back in the room wearing a pair of black high heeled shoes, blue knee socks, a short red white and black tartan skirt, a white blouse, a black tie and a grey cardigan. If I hadn’t been gagged I would still have been dumbfounded. He then sat down on the bed next to my thighs and told me to roll on my back. Reluctantly I rolled on my side but because my feet were pulled up against my ass I couldn’t roll any further.

When he saw this he told me to roll back on my stomach again and that he would untie the rope between my feet and wrists. I saw a tiny chance of escape but before untying the rope he picked up another piece of rope out of the shoebox standing on my desk and looped and cinched it around my wrists. He then untied the cinch noose around my wrists allowing me to stretch my legs. That was when he spotted my butt plug. While he was admiring my ass I noticed that he wasn’t wearing panties either.

He then told me to roll on my back again. I rolled over as far as I could without lying on my arms. Next he pushed my skirt up and grabbed my penis with his left hand. My erection had by now completely gone down and didn’t spring back at once. He smiled and muttered something about performance anxiety and making me feel more comfortable.

From the stuff on the floor he pulled a pair of soft, fluffy and baby blue cheerleader legwarmers. He pulled them over his hands and arms and muffled my penis with these mittens. Slowly he started massaging and rubbing my cock and despite my apprehension I was rock hard within minutes. After a while he grabbed my shaft with his left hand and kept rhythmically stroking it. He also pushed the open end of the sleeve of his right arm over my erection so he could massage and rub the tip with his right hand.

Every time I was on the verge of having an orgasm he would quickly pull away his hands so I was just humping the air and moaning in my gag. I desperately wanted to come. My cock was so hard it hurt.

After at least an hour he sat down next to my bed, directly facing my throbbing penis. Staring down the barrel of the gun so to speak. He teased me for a few more minutes before firmly grabbing my cock with both his hands and started to properly jerk me off with short, firm strokes. After about a minute I had an absolutely mind-blowing orgasm.

Cum exploded out of my tip and hit him full in the face. The second load landed on his chest and lap. Methodically he massaged every last drop out of my dick with one hand and catching everything with his other. When I had given everything I could he stood up and told me he would be back. Lying on the bed and looking up I could see his erection completely tenting up his skirt.

He quickly left the room and still trembling from the release I just laid back on the bed and tried to relax, marvelling at what had just happened.

After about half an hour my roommate walked back into my room wearing nothing but the high heeled shoes and the blue socks. He asked me if I wanted him to untie me and I nodded my head. First he untied the ropes around my legs before helping me first to sit up and then to stand up. Next he undid the straps of my ballgag and took the ball from my mouth. He then asked me if I was planning to beat him up. Working my jaw and regaining control of my voice I assured him I wouldn’t hurt him. After that he undid the belt around my waist and untied the rope around my wrists. Then he helped me get out of the ropes around my chest and elbows.

As we were standing there he asked me if had enjoyed myself. I felt ridiculous! I had a dildo up my ass and I was wearing a schoolgirl uniform. And now I was having a conversation with a guy who was naked from the knees up and who had just jerked me off. Carefully choosing my words I told him that this was far different from anything in my wildest dreams. He then asked me if there was any chance of doing this again. The surprises just kept on coming! I told him I would think about it and then that I really wanted to go to the toilet and afterwards take a shower. He said he would await and accept any answer I gave.

We then went about our own business and later that night our other roommates came home. They never found out anything happened. I did have the lock of my room replaced that week.

09.01.10