Hotel Wrestling in Chicago
Barfly6363@aol.com


I traveled to Chicago for work and decided to spend the weekend to do some shopping before returning home. I looked through the personal ads all week hoping to hook up for a wrestling match and found no ads until Thursday when I checked at lunch. My heart skipped a beat thinking this may work out after all.

I responded on Thursday night and received an e-mail Friday morning. We exchanged information about each other, including our wrestling styles, ages, height and weight, and agreed to meet in front of the Water Tower on Michigan Ave that evening. I could barely concentrate on the late afternoon seminar that I was in, thinking about our meet up. I left the seminar as soon as it was over, rushed to my hotel, showered and arrived at the Water Tower about 15 minutes early, just to be safe and check things out. I was in a big city by myself and wanted to be cautious. Jan told me what she would be wearing and I spotted her walking up Michigan Ave a half block away, through the maze of people, and she was walking alone. I began to walk toward her, she spotted me and we both smiled at the same time. She looked exactly like she described herself in her e-mail. Early 20's, 5'6, 170ish, the same size as me, although I was a few years older. We hugged and then began to talk as we strolled down the street. We ended up in front of Victoria's Secret and we both laughed about that, and then she agreed to come to my hotel room at 10:00 the next morning to wrestle. We hugged again and then she turned to walk away as I turned to go inside VS to purchase my new wrestling attire.

I was on almost no sleep when I woke up Saturday morning, took a shower, put on my new red thong set and pink bathrobe and waited for Jan to arrive. I paced nervously as 10:00 came near and was disappointed when I didn't hear a knock on the door. I continued pacing until I heard the elevator doors open about 2 minutes later and then heard a light knock on my door. Jan was smiling when I opened the door and we hugged as she stepped inside. I closed and locked the door behind her. Jan was just as excited as me and asked to change immediately and went to the bathroom to do so. I untied my robe and let it fall open in front while I waited for her to come out.

She came out wearing a very cute white, see through bikini set while I dropped my robe to show her what I was wearing. I admit, we were both on the chubby side, especially from the tummy through the thighs, but we weren't modeling, we were wrestling, and we were both happy with what the other was wearing. To say I stole glances at her bikini is an understatement. I stood there smiling with my eyes traveling from her breasts on down.

We dropped to our knees on the comforters that I had put out, started giggling, and began to wrestle. We were going to wrestle a friendly match and that's what it was. Jan got me in a headlock and held it, not hard, while I wrapped my arm around her tummy and rolled out of it and on top of her. She pushed me off and came after me. We allowed ourselves to be put in some holds and dodged others. We were both proficient with the scissors and Jan tried several attempts to get hers on me, including her headscissors. We were perspiring in no time and our nipples were visibly hard. Jan came real close to wrestling me into a headscissors and I think she would have gotten it if I wouldn't have been struggling so much to keep my head from between her thighs. She basically let me go, so I let her get a body scissors on me, kind of as a reward. Turns out I let myself get wrestled into the first submission. We were both laughing as she wrapped me up from behind in her body scissors and then wrapped her arms around my head and pulled me tight against her. I could feel her hard nipples pinned against my upper back. We were sitting on our butts in front of the window with the morning sun shining in and we were both giggling as Jan maintained control by going to her back and pulling me on top of her. She had me in kind of a sleeper hold with her arms around my head but wasn't holding on real tight and I pushed her arms off my head with my hands. Her scissors were another story. Every time I tried to lift up to reach for her ankles, she would wrap her arm around my head again, or put on a nelson and pull me back down against her. Her thighs were wrapped around my tummy holding me well but her calf's were on my hips and as we struggled, her calf's ended up pulling the waistband of my thong down on both hips. I don't know if she was doing this on purpose or not. I broke free at one point and sat up quickly to try to grab her ankles and saw that my thong was down in front showing my tiny mound that I had cut into a square during my morning shower. My escape was short lived though, because she pulled me back down and this time she cupped my chin with her hands. I've been in this same hold twice before in matches and submitted both times. Its a scary hold to be trapped in. If your opponent pulls your head back in just the right way, your breathing is restricted. Luckily Jan didn't do that to me, but she had her hands secured under my chin and I couldn't do anything about it. My back was flat against her with her legs wrapped around my tummy and her hands under my chin. I was pretty sure my nipples were exposed by now, but I couldn't see them from my position to be sure. My arms were flailing on my sides as I struggled on top of Jan and I could hear the maid running the vacuum cleaner in the hall outside when she must have tapped my door with it. I arched my neck back and Jan did too to make sure nobody was opening the door and then Jan started laughing and asked for my submission. I gave it to her, she had me and I couldn't escape.

Jan released my chin and the scissors and I rolled off her and to my back. My nipples and bush were exposed but I was too tired to cover up at this point. Besides, Jan didn't care. I know because I saw her stealing glances my way. I complemented Jan on her submission and then rolled to face her. She was still on her back, looking up at the ceiling talking to me as I gazed up and down her body. She was trimmed down below like me and when I looked up, she was gazing down at me with a smile on her face.

We took a short break and then moved to our knees again to begin the second fall. We were laughing again and I liked the way the match was turning out. Nothing too serious here. We moved into a long bearhug on each other that had our bodies pressing as we each went for the takedown on the other. I got it by falling backwards and pulling her with me. As I went down, I spread my legs and wrapped them around her waist. I was now on my back with Jan right on top of me, holding her in a body scissors. I wasn't squeezing hard, I more or less had my legs wrapped around her and my ankles locked behind her back. (The last time I had been in this position was a year ago with an old boyfriend) We lost our bearhugs as we went down and Jan grabbed my wrists and then pinned them above my head. This hold wasn't working out like I had planned. I tried to turn us using my legs, but with Jan's weight over me, she prevented the turn. She was using her weight to pin me down and the body scissors I had on her wasn't having any affect. Whatever advantage I had when I brought her down was now gone because I couldn't get the leverage on my scissors to squeeze her very tight, so I unlocked my ankles and let them drop down. Big mistake as she was waiting for that. She got my left ankle with her right ankle first and I immediately raised my other ankle up in the air to avoid capture. She was after it though as we wrestled with our legs and thighs in a battle of keep away. Jan layed down against me, kept my wrists pinned above my head and controlled my left ankle as she looked back to see where my free leg was. Within in seconds, she captured it and locked on the grapevine. We were both laughing, although she was giggling more than me at this point. Could you blame her? She was controlling the match. She didn't have me spread wide, but as hard as I tried, I couldn't break my ankles free. Jan slowly lifted her upper body off me and I got my first look at how hard her nipples could get. They were dark and had slipped out of the top of her bra. I, however, had no room to talk because my bra had slipped down during the struggle and my full breasts were exposed. Jan looked down and smiled before laying over me again, gently. She stretched my arms out further above my head and pinned her now exposed breasts against mine. She held me like this for a couple of minutes while I struggled under her and then she slowly started to spread my legs in the vine.

We were both grunting lightly as we wrestled against each other and I could hear people talking as they passed by in the hall. I thought to myself, if they only knew what we were doing behind the door they were walking by! She released my wrists and then wrapped her arms around my head, holding me secure and then dropped her head down on my shoulder. Her mouth was near my ear and I could feel her warm breath on my neck as she continued to grunt lightly while holding me pinned. She wasn't submitting me from this position, yet, but more or less had me in an unbreakable pin. And then her submission move came into play. She slowly started to spread my legs in her vine and as she did that, the intensity of the match picked up and we both started grunting louder. I could hear knocks on the door across from ours and laughter, it sounded like friends were gathering in the hall getting ready to go somewhere together. Jan shifted position on top of me slightly and then started to slowly force me to bridge using her legs to pull on mine and straddling me with her body. I accidentally grunted loud when she bridged me and suddenly I could hear the people in the hall quiet down and start shushing each other. Jan was riding me in the grapevine and still had her head on my shoulder when she whispered “I think they heard you and they are trying to listen in, I can hear them leaning against the door” and then she let out a loud grunt of her own, started giggling and whispered “I've got you, do you want to submit?” I was spent. I had been grapevined in other matches, sometimes I could escape, sometimes I could free an ankle, but I couldn't do anything to escape this one. Jan was riding me like I've never been ridden before in a wrestling match, or lovemaking for that matter, because that was the position she was in on top of me. I let out one more grunt/scream, louder than I should have and tried to turn us in an escape attempt, to no avail. With my back arching and Jan laying on top of me, I told her “You got me, I submit” and the second fall was hers.

Jan released the pressure and slowly lifted her upper body off me, supporting herself on her hands but kept her straddle over my hips. As she lifted up, her exposed breasts bounced over me. We giggled as we heard the whispering outside our door and then Jan rolled off me and to her back, taking a break. We were laying next to each other, catching our breath and perspiring when Jan reached out and touched my shoulder. She complemented me on how well I was wrestling. I laughed and said I didn't think I was wrestling very well because she kept winning. I sat up first and looked over at her as she wiping perspiration from her forehead. I glanced down quickly and noticed her pubic hair was cut into a little tight square and as I shot my eyes back up to her breasts, noticed that Jan was watching me. I had only taken a quick peak and she was wearing a see through bikini anyway, but it was embarrassing to get caught like that. Jan broke the silence and asked if I was ready to wrestle again.

We rolled to our knees and made adjustments to our outfits in front of each other. Jan tugged the front of her bikini bottom down showing off her very well trimmed mound though she didn't make eye contact when she did it. She knew I was watching.

We crawled toward each other on our hands and knees but instead locking up in a bearhug, Jan reached out quickly, grabbed my wrist and pulled me off balance. I fell to my tummy as she turned around and gained a straddle on my back. I tucked my arms tight against my sides to avoid a full nelson attempt but she didn't try it. She didn't even lay down against my back. Instead she held her straddle on my butt and then slid up slowly, gripping my sides with her thighs as she moved up to keep me in place. When she slid up to my middle back I bucked up hard to try to throw her off, but that only caused her to slide higher, to my shoulder blades. When her right leg slid over my right shoulder next to my head, I knew what she was doing. She was going for the rear headscissors. We had talked about the headscissors during our phone conversation and when we first met during our walk down Michigan Ave. It was our favorite hold and we were both good at applying it. I even told her something that I've never told anybody in my life. That I found the headscissors erotic at times when wrestling. When I said this to her, she grabbed my wrist excitedly with a big smile on her face and said I wasn't the only one and she had never told anybody either. Jan said she liked the domination factor she gained with her headscissors, knowing she was in control once she got her thighs wrapped around her opponent's head or neck and got her ankles locked. I quickly agreed with her and went on to say that I found the whole sequence exciting, from wrestling my opponent into headscissors position to wrapping my thighs around their head, crossing my ankles and then laying back to enjoy the struggle. We were still on Michigan Ave at the time and Jan turned to face me and whispered that she had 3 orgasms in a 15 minute headscissors and her opponent never knew. She said they were wrestling in a hotel and the more her opponent struggled, the more excited Jan got especially with her opponent's head pinned against her crotch like it was. I told Jan my record headscissors was just over 10 minutes with 2 orgasms. We had so much in common that it was easy to talk to each other about intimate details of our matches.

But this wasn't a stroll down Michigan Ave any longer, this was a real match and Jan was in the process of headscissoring me. The pace of the match picked up now and this was the fastest and hardest we had wrestled. I was conceding the right side of my head to her, there was nothing I could do about it now, her inner thigh was pressed against my cheek. I had to block her left thigh from coming over the top! I quickly reached my left arm up for the block and when I did Jan grabbed my wrist and pulled my arm to the side, dropping her left thigh over my left shoulder. I tried to duck my head down and out of the way, but Jan was too quick with her thighs and pinned her inner thighs against my face to secure my head. I was on all fours in this position with Jan's crotch pinned against the back of my neck and her thighs holding my head. She dropped her hands down over my head and then pulled us down to our sides using her thighs and we rolled right into a lamp that hit the door and broke. The crash was loud and we both froze, not knowing if anybody else heard the noise. My head was still locked between her thighs and I was staring at the bottom of the door, watching and listening, when there was a knock on the door followed about 5 seconds later by a call to the hotel room's phone.

Our wrestling match was over, for the time being.