Chapter 1

Her name was Margot. She was introduced to me at a party of a mutual friend. She was gorgeous and my first thought was, I was absolutely thrilled to be introduced to her, but her conversation starter was, “You look kind of wimpy.”

I’m not a big muscular guy, but I’m relatively fit and I get occasional compliments on how I look. I’m pretty confident in my physical abilities. I played football and wrestled in high school. I won nearly all of my wrestling matches. Sure, that was fifteen years ago, but I’m still in pretty good shape. I work out three or four times a week and I run a little.

“You don’t work out much, do you?” She asked. “In fact, do you exercise at all? You look pretty out of shape but I bet you think you look great.” Then she says, “I bet even I could take you.” She eyeballed me from head to toe with this snarky smile on her face when she said, “I bet if we wrestled, I’d win.”

What a snotty, arrogant little bitch, I thought. I didn’t know how to respond at first. She must be crazy to suggest she could stand a chance of beating me in a wrestling match. “Really ... and the stakes for this bet?,” I asked.

“Sexual domination,” she said confidently. “If I win, I get to do anything I want to you. If you win, you get to do anything you want to me.” Then she said, “Don’t worry. I won’t hurt you. This isn’t about pain. I’ll just defeat you, restrain you, strip you naked so I can get a good look at your wimpy body, and then humiliate you sexually. I love humiliating cocky little boys like you.”

I was a little pissed off. I’m not cocky. I do my best to be humble and polite. I wasn’t sure I wanted to continue any further conversation with her ... but she was so hot, I found her hard to resist.

She was suggesting she might actually be able to beat me in a wrestling match. That’s absurd. Was this a come-on? Her offer seemed too good to be true. I had always fantasized about wrestling a hot chick, tying her up and having my way with her. She certainly filled the bill in the looks department, and while she appeared physically fit, I knew she wouldn’t stand a chance against me. It was obvious to me, she wanted me to do to her exactly what she claimed she would do to me - to be dominated and humiliated.

That’s the full extent of the thought I gave to her proposition before accepting her challenge. My dick was doing all my thinking for me. I was getting hard thinking about it. All too often, I think my dick is very smart.

She told me she belongs to a gym with a boxing ring. She would reserve the ring for a private session. She said she’d call with the address of the gym and tell me what time I should meet her there.

I must admit, I found it a little discomforting that she belonged to a gym with a boxing ring. I wondered, who is this woman? Still, I’m 6’ 2” and I weigh 180 lbs. She was maybe 5’ 4” and 130lbs - give or take.

I went home and for the next few days, I couldn’t stop thinking about what was to come. Two and a half weeks went by and I began thinking she wouldn’t call until finally, 19 days later, the phone rang and it was Margot.

“I reserved the gym for one week from today at 8:45pm sharp,” she said. She told me the address of the gym and that the normal closing time is 8:00 so everyone will have left. “Knock three times so I’ll know it’s you ... unless you’re afraid.” Then she laughed and said, “You can still back out. It’s not too late”

“Right,” I said. “I’ll be there.”

I was surprised at myself for accepting her challenge. It almost seemed like it had to be some sort of setup but she was hot and acted so sexy, I had to find out for sure. I asked a couple of friends who were at the party about her, but no one could tell me much more than I already knew.

I couldn’t stop fantasizing about it. I couldn’t wait to see her naked, helpless, and under my control. All the different ways I would manipulate her - what will she wear? ... should I bring rope?

Finally, the day arrived. I made sure I was there at exactly 8:45p.m. I wore a black thong under my clothes. I brought straps - the kind of straps with the soft Velcro ends that can be secured around the wrists or ankles, and the other end can be secured to an anchor point. I was going to strap her to the ring and make her the sex toy I always fantasized about.

I walked to the side door of the gym and knocked three times like she told me. I heard the deadbolt turn and when she opened the door I was taken by the amazing outfit she was wearing. She had on black silk boxers that slit up the sides to the waist. I noticed they were attached by Velcro at the waist so they would come off easily. I’d seen shorts like these in catalogs and had often thought, they’d be perfect if someone were tied up. They’d come off easily without interference from the restraints. She had on a tiny, black string bikini top. Once I tied her up, I would have no problem removing her clothes. Her breasts were medium sized but full and pert. She was stunning. It was obvious she was excited too, as her nipples, perfectly placed as if they were looking straight at me were standing at attention. My heart began to pound as my anticipation grew. I walked in and she locked the door behind me.

She said, “Just so you fully understand, you and I are about to wrestle in the ring. Whoever wins will have the right to dominate the loser in any sexual manner the winner chooses - no pain, just sexual domination. Agreed?”

I said, “Isn’t that the bet we made at the party? Of course, I agree.”

She said, “I just wanted to make certain you understood the terms so there can be no confusion. Once we start, there will be no backing out. One more thing,” she said, “Our fight will be recorded.”

“Backing out? Why would I want to back out?” I asked. “You’ll be the one wanting to back out. You’re mine.”

I wondered ... why is she so confident and cocky? Wait, did she say recorded?

“Why will we be recorded?” I asked. “You’re not going to post this on the internet.”

“No, no,” she said, “but I want a copy for myself so I can get a laugh once in a while, and I’ll give you a copy so you’ll never forget the humiliation you’re about to experience.

She held out a pair of black silk boxers just like the ones she was wearing. She said, “You’re wearing these - that way it’ll be fair.”

I said, “I already have something on I think you’ll like.”

“No,” she said, “You’ll wear these.” She pointed to the men’s locker room and in a commanding tone said, “Change in there.”

I asked, “What do you mean, fair?” Then I made a rather pathetic claim, considering I’m much larger than she, “You have two items on and I’ll only have one. How is that fair?”

She laughed and said, “Picky, picky, picky. What’s the matter, are you afraid you’ll lose? You’re bigger than me. It’s a wash.”

I grabbed the boxers and headed to the locker room.

When I came back, she was waiting for me in the ring. She had turned off most of the lights except for a couple of spots along the end walls well away from the ring. Another two were pointed at the long wall and there were lights directly above the ring. It was a large room and outside of the spots, the room was dimly lit. Considering the “warehouse” setting, the ambiance was very sexy.

Margot looked magnificent. The tiny bikini top barely covered her nipples. Her shorts, slit to the waist, exposed her upper thighs as she walked around the ring.

Already, I was getting excited. I really didn’t want to get hard yet because these shorts were so loose and revealing, I was afraid I’d pop out. I was feeling a little insecure about that. I just didn’t want to give her the opportunity to make fun of me.

The ring was three ropes high. It was small - about 15 feet across and raised about 6 inches off the floor. I didn’t see any workout equipment. I figured there was probably another room for that. Obviously, this was “the fighting room.”

It was an old warehouse that had been renovated. The walls were cinder blocks, about 30 feet wide and 75 to 100 feet long with four steel support poles down the center the long way. The ceiling was high, 20 feet or so, similar to a high school gymnasium. Three of the block walls were exposed, the longest of which had a large painted mural of two fighters in a boxing ring. Other than the mural, the walls were painted a kind of dark steely blue as were the ceiling, the pipes and ductwork. The wall opposite the mural had an elegant, dark navy blue, velvet curtain covering it from end to end.

On closer inspection, the fighters in the mural were wearing boxing trunks, but each of them had hard-ons, creating large tents in the fronts of their trunks. The fighter throwing a punch had a mean, dominant expression on his face as he was punching the other guy in the gut. The fighter getting punched was doubled over with a pained, helpless expression. Additionally, the cheering crowd in the painting was comprised of all women. The painting told quite a story. It gave me a bit of a chill thinking about it.

“What are you waiting for?” Margot asked. “Are you having second thoughts?”

She startled me. I was trying to absorb everything in the room as I was looking around. I had never been in a real boxing ring before and this was nothing like what I had pictured in my mind.

I didn’t want her to know this was my first time in a ring so I pulled the top rope up like I knew what I was doing and climbed over the center rope into the ring.

I hadn’t even stood up straight when she attacked.

Fortunately, I was quick enough to grab her wrists to keep her at bay but she slammed her wrists together, pinching my thumbs in between.

I let go immediately and gasped in pain. Before I could complain, she quickly got behind me, wrapped her arms around my neck and climbed onto my back. She was quick.

Her quick moves were unexpected. She caught me off balance and I immediately dropped to the mat.

She kept her arms wrapped around my neck, choking me a little, but mostly hanging on for all she was worth. As soon as she had the chance, she wrapped each of her legs around mine with her feet together in my crotch.

She was stronger than I expected and no matter how I tried, I was unable to get loose. I managed to get to my hands and knees but she held on, still clinging to my back and not giving an inch. I struggled and struggled, trying to get her off of me but to no avail.

I could feel myself getting out of breath and tiring a little but finally, I was able to get back to my feet.

I thought, if I could get to a corner, I might be able to back up quickly and slam her into the post with hopes of exerting enough pressure against her to knock the wind out of her and force her to relinquish her grip.

She was desperately trying to bring me down again but I managed to get her back against the turnbuckle and began pressing against her as hard as I could to force her to let go. She didn’t.

I looked down and there were the straps I brought, already tied to the ropes, one on each side of the corner on the top rope and one on each side of the corner on the bottom rope. She must’ve secured the straps while I was changing. Was she right when she said she would win? Could I have so underestimated her?

When I saw my straps already secured in place, I lost my concentration for a second and I felt one of her arms tighten around my neck. Her hand locked onto her other arm that was now grabbing the top of my head. She exerted extreme pressure under my chin. She was choking off the blood flow to my head. I wanted to tell her I’d had enough but I couldn’t talk, I couldn’t swallow and I couldn’t breathe. I was losing consciousness.

When I came to, I was sitting in the corner of the ring, my wrists secured to the top rope with my straps, and Margot securing my right leg to the bottom rope. My left leg was already tied.

It was over almost as quickly as it began. I suffered a humiliating defeat at the hands of a small girl no less. What could she have in her plans? She knew from the beginning she would win, and she knew how she would win. She had everything perfectly planned from the start.

My god! How could I have been so stupid? My cock had made another bad choice.

I knew nothing about this woman or what she might be capable of. She is a black widow and now she has ensnared her helpless mate in her trap to do with as she pleases. As I sat bound in the corner of the ring and unable to do anything about my situation, I became apprehensive and afraid.

“Relax,” she said, “I won’t hurt you. I just love toying with little boys like you.” Then she laughed.

“You weren’t much of a threat to me,” she said. “I had you right from the start. You were so sure you would win. You thought, just because you’re a big, strong man, you could handle a little girl like me. Well surprise ... you can’t. It’s time for me to collect.” Then she leaned in front of my face and spoke in a soft voice, “I’m going to humiliate you beyond your wildest imaginings. You’re going to be my little sex toy. I like seeing a man helpless and nervous.”

My whole body was filled with fear and apprehension. I couldn’t deny the heightened level of anxiety caused by my situation, yet I was her slave and I found it sexually exhilarating. I sheepishly shook my head no as if I stood a chance of changing the situation.

She began telling me. “I have many surprises for you little boy - things you wouldn’t dream of in a million years. You look perfect, just like you did at the party. I picked you specifically because of your looks and your demeanor. That’s right, I like the way you look, contrary to what I said at the party. Why do you think I picked you? I certainly wasn’t going to pick some scrawny, homely guy.” Then she tells me, “I had so much fun toying with your manly pride. I knew you wouldn’t stand a chance and now I get my reward for victory. You are at my mercy. I plan on taking full advantage.”

She looked magnificent against that navy blue curtain as she strutted back and forth in front of me - taunting me - teasing me. She caressed herself slowly, rubbing her breasts, then her crotch, then back to her breasts. She was obviously excited over her victory. “I told you I could beat you,” she said. “I won just like I said I would and now I’m going to make you pay the humiliating price.”

She knew how much she turned me on. My fear turned to lust, then back to fear and back to lust again.

She knelt before me, still slowly rubbing herself. I could smell her excitement.

I wanted to resist but I couldn’t help becoming hard. Part of me didn’t want her to see how excited I was, but another part of me wanted her to know how much I desired her. I found my humiliating predicament taking over every fiber of my being and I craved to know what she had in store.

She reached over and lightly ran her hand up the inside of my thigh. I flinched with anticipation. She stopped just short of my balls and slowly slid her hand back down my leg. I felt a pause of disappointment. She continued to tease me.

She smiled and said, “You like this don’t you?”

I wanted to tell her, “No” but I sighed and said, “Yes.”

She looked at my cock and said, “I can see how much you like it.” She continued with her gentle touch on my thigh.

I became extremely hard, anticipating that first contact I knew would take my breath away. I think I was harder than I’ve ever been, almost to the point of being in pain and she hadn’t even touched anything beyond my thigh. I couldn’t believe how she was turning me on and how incredible it felt to be dominated and teased by her.

I began to squirm a little, actually trying to maneuver my cock into her hands when they were close. I felt a tremendous sense of frustration that she wasn’t touching me where I wanted to be touched.

Finally, she slowly slid her hand over my silk shorts, feeling my balls and up my cock. I gasped and then moaned with excitement. Again, she smiled. She said, “I want you turned on more than you’ve ever been - completely turned on and helpless.”