I had the following wrestling match against Toby when we were 18 years old and seniors in high school. We were both about 5'8 and 130 pounds or so, definitely on the skinny side, and we met during swimming class.
Toby invited me to spend Friday night at his house where we were going to watch movies. Toby's parents were divorced and he lived with his Mom who was going out to dinner that night, which was an added benefit.
I arrived around 7:00 p.m. Just as Toby's Mom was leaving for the evening and we went down to Toby's basement where his bedroom was at. He had a really nice set up in his basement with carpet, a t.v. & vcr, exercise mats in the corner and mirrors on both corner walls.
Toby put a movie in the VCR and then went to the refrigerator that was nearby and pulled out a bottle of wine. He said he had gotten it earlier that day and snuck it inside before his Mom got home from work.
The party was on!
In no time we were both getting drunk and the movie was the farthest thing from our mind. Toby asked if I wanted to wrestle and I said sure. Toby hopped up, went into his bedroom and came out wearing a tiny white Speedo that was at least one size too small. I said no fair, I didn't bring anything to wrestle in and he came back out and tossed me a matching white Speedo that had seen better days that was also at least one size too small. I went into the bathroom and put the Speedo on. It was really tight fitting and almost see-through in the front because of all the washings it had been through.
When I came out, Toby was kneeling on the exercise mats waiting for me with the wine and our glasses nearby. I walked to the mats and dropped to my knees, nervously. We both took another swig of wine and the wrestling match was on.
We started from our knees and wrapped around each other, trying for the takedown. I was able to get Toby down but he immediately wrapped his legs around my waist in a body scissors and locked on tight. We struggled like this for several minutes with Toby letting out the occasional grunt. I was able to push Toby's arms off me but he was on me tight with his legs, which were secured around my waist with his ankles locked against my back. I was on my knees at this point with Toby on his back and when I looked down, I was shocked to see that Toby had a big boner in his Speedo. I say big because even though we were built the same, Toby had a huge cock for his age, which I had seen when showering after swim class. We continued struggling like this with Toby's crotch pressed against me when he got me down on the mats, off my knees and was able to position himself against my back, where he promptly locked on a tight full nelson. Toby was sitting behind me on his butt and I was on my butt, locked between his thighs with my arms straight up in the air in his nelson. We were in front of the mirror and I had a perfect view of the hold. I was also in perfect position for Toby to pin his erection against my lower back and I could feel him doing so, only it was skin on skin and I could tell that Toby's erection had slipped out of the top of his tiny Speedo. We stayed in this position for several minutes with Toby's boner pinned against my back while I tried to wrestle free but couldn't. I'm still not sure if it was feeling Toby's hard on against my back or wrestling in Speedo's, but the next thing I knew, I was aroused as well and had a nice tent going in the front of my Speedo.
Toby was grunting now and layed down on his back, pulling me on top of him still holding the full nelson with his thighs clamped around my waist. I was able to bend my neck forward just a little and I could see us in the mirror. My ribs were showing and I had a sweet boner going in my Speedo. I could see Toby peaking over my shoulder, looking into the mirror, as he continued to pin his boner against my back while continuing to grunt. We were both sweating and Toby's eyes were glassy. I realized that he was trying to get off on my back, which would have left me high and dry, so I submitted to him.
Toby released the nelson and then the scissors and I slowly rolled out from between his legs, then turned to face him, showing off my own boner as I did so.
Toby looked at my boner and smiled, but I could tell his only focus was getting himself off. He reached down, adjusting his Speedo and stuffed his erection back inside.
We decided that now was a good time to hide the wine bottle and our empty glasses so we picked them up and hid them in Toby's closet. When I stood up to leave his bedroom, Toby jumped me and I landed on my back on his bed, bouncing into the mattress as Toby slid onto my hips in a straddle position. This was the first wrestling contact on my boner and it felt really good. Toby slid on my waist and then started to move into a school boy pin on top of me. I could see his boner sticking out of the top of his Speedo while I tried to wrestle free. His bed didn't have a headboard, but the head of his bed was pushed up against a wall and I ended up wrestling myself against the wall while Toby held the straddle and inched higher. Toby was sitting high on my chest and had his knees pinned into my shoulders when he dropped the front of his Speedo to free his erection. I can still remember how white his cock was compared to the rest of his body, and how hard and long it was too. As I laid pinned under Toby, he grabbed his erection and told me to suck it. I was shocked and said no way. He began almost pleading, saying c'mon, I've got you pinned, just suck the head for a second. I told him to stroke me. He reached back with his free hand and started rubbing my boner and then stroking it. It was the first time anybody besides me ever stroked my cock and it felt good. I let him continue stroking me while he held his boner near my mouth until I was close to shooting my load. Toby knew I was close and started bending forward, trying to force the head of his boner in my mouth while continuing to stroke me. I was turning my head left and right, trying to dodge his boner while he briefly pinned it under my chin. Toby was gripping my pistol tight but slowed down the stroking, going up and down, up and down, as I began to bridge, trying to escape. As I began to bridge, Toby slid his erection off my chin and pinned the head of his cock against my lips. I began wrestling frantically, bridging even higher, trying to escape when I noticed the basement light outside Toby's room blinking on and off. I quickly began tapping Toby's leg as I turned my head to the side to avoid having him slip his boner into my mouth and said, “Toby, the light is blinking on and off.” Toby said “shit, my Mom!” and removed his hand from my erection, slid his boner back in his Speedo and slid down on my chest into a school boy pin. Just then Toby's Mom came around the corner, into the bedroom and asked what we were doing. Toby said that we were wrestling. I layed pinned under Toby and suddenly realized that Toby never pulled my Speedo up and my boner was exposed! Toby's Mom stood in the doorway and began talking to us as I frantically tried to free my arms but couldn't because Toby had his knees on them, pinning them into the mattress. Toby's Mom moved closer, asking questions, did we watch the movie, how long have we been wrestling, etc. Toby was answering his Mom by turning his head, but he wouldn't get off me and I knew why, his boner was still standing up in his Speedo, almost spilling out of the top. Toby's Mom had definitely seen my boner, and as she walked up closer to the side of the bed, I knew what she was doing. She was checking to see if her son was hard too. Toby's Mom was making eye contact with both of us now and continued talking. When she asked why we were wrestling on the bed Toby quickly replied that we had just changed to wrestle on the mats and I pushed him on the bed and we started wrestling. I was embarrassed yet extremely turned on knowing that Toby's Mom could see my exposed erection and she wasn't saying anything about it. She didn't freak when she walked in and saw Toby pinning me with my Speedo pulled down in front and my boner standing up and I thought that was really cool. Toby's Mom continued talking to us and then suggested that we wrestle on the mats while she watched. Toby quickly agreed to that idea, hopped off me and kept his back to his Mom while he circled his way out of the bedroom so she couldn't see the erection in his Speedo. I stood up off his bed while his Mom watched my boner and then I slowly pulled my Speedo up, covering it. We made eye contact and there was a hint of a smile on her face as I followed her out to the mats.
Toby and I dropped to our knees to begin the match while his Mom moved a chair next to the mats, closer than she really needed to be. We started wrestling and Toby quickly got me in a headlock and flipped me down to the mats, on my back and my back made a loud slap as I went down. I immediately began to try to wrestle free while Toby worked to slide himself on top of me for the pin. My boner was tenting the front of my Speedo at this point and it was a huge turn on to me knowing that Toby's Mom could see it. Meanwhile, Toby had lost his erection, probably embarrassed to be wrestling in front of his Mom like we were. Toby slid into a school boy pin on me and I threw up a fast bridge, surprising him. I arched high and flipped him over my head. It was the first time I've ever bridged my way out of a pin and I was happy to do it in front of his Mom like I did. I immediately went on the offensive while Toby tried to scoot away. I ended up on the side of him and wrestled him to his back. I reached down, grabbed his legs and rolled him into a perfect cradle. His Mom was watching intently and I had my back to her, laying on my side, while I cradle pinned her son. Toby was struggling furiously trying to wrestle free and I had a really nice tent going in my Speedo at this point that his Mom couldn't see. Toby's Mom was bent forward watching us so I rolled to my back and began to arch slightly, giving her a full view of my Speedo clad erection. It was at this point that Toby's Mom said she wanted to wrestle the winner. I realized that I was going to be wrestling Toby's Mom, there was no way that Toby was breaking my cradle. Less than a minute later, Toby's struggles stopped and he submitted the match to me.
Toby's Mom said she was going to change and I released Toby from the cradle. Toby immediately said “shit dude, you are going to wrestle my Mom and I don't want to see that, I'm going to my bedroom and finish off the wine” and he took off, leaving me alone on the mats.
Toby's Mom, who I'll now refer to as M going forward, came back downstairs wearing a two-piece black leotard to wrestle me in, if there is such a thing. Anyway, she had black tights on and basically a white sports bra, that left her tummy and back exposed.. M asked where Toby was and just then he closed his bedroom door. I told her that he was watching a movie and she seemed o.k. With that.
I should explain what M looks like at this point. First, she is a MOM! Second, she is about 5'6 and 175 pounds and she completely filled out her leotard. She was large through the thighs, hips, tummy and breasts. She wasn't a beauty queen, but she was actually kind of pretty.
We began moving toward each other and I quickly got behind her, wrapping my arms around her tummy in a reverse bearhug. She grunted, which I thought was funny, but it showed she was taking the match serious. I pinned my body to her back and my boner immediately sprang to life. Luckily my Speedo was holding or it would have been bare skin against bare skin at this point. We were on our knees and M went down on all fours so I slid up on her back, straddling her as I tried to wrap my thighs around her hips to hold her tight. As M went down on all fours, my hands accidentally slid up so that I was holding her just under her breasts. My hands were actually pinned against the bottom of her breasts and I was shocked when she said that I could move my hands if needed to gain the hold I wanted. I slowly slid my hands up, wrapping them around her breasts as I held my mount on her back. M began to wiggle her hips, trying to toss me off, as I held on tight, mounted on her, as her tights began to slide down and her top began to slide up, exposing more of her back. My boner was going wild in my Speedo and I could feel her nipples getting hard in her sports bra.
M wiggled hard to her side and I lost my hold, rolling off her back and to my side, so that we were facing each other. M moved first, reaching out, grabbing me and pulling herself tight against me. We were face to face at this point, each trying to wrestle the other to their back when M got her top leg over mine and dropped her beefy thigh down against my hip, gaining control. As she raised her top leg up, I could see her tights sliding farther down her hips. I could feel her sliding her bottom leg under my waist and I tried to push away, but wasn't able to before she wrapped her thighs around my waist and crossed her ankles, gaining the scissors on me. We were laying on our sides, facing each other, almost face to face in this position and M was wrapped around me good. I had no idea she had wrestling experience, but she obvious did to lock me up like she had me.
She was wrapped around me tight and I suddenly realized the top of my boner was pinned against her crotch. I was hard as a rock and the contact on the head of my boner was driving me crazy. I was still contained in my Speedo, but the head of my cock was rubbing against her crotch as we struggled against each other. We were so close we were almost kissing and our lips did touch briefly at one point before I pulled away.
I looked down and I could see M's tights inching farther down her hips, which were milky white and provided a nice contrast to her black tights, but I couldn't see how far they were down in the front from my position.
She wasn't applying submission pressure, but she definitely had me trapped, however her tights were rubbing against my waist and that hurt. I didn't want to tell her and ruin our match, but I had to. She immediately released the body scissors and apologized, saying that she was worried that might happen if she got a scissors on me. She told me to wait while she changed and she came back downstairs barefoot and wearing a robe. She walked to Toby's room, inched open his door and turned to me smiling. She closed his door and then walked over to the mats and said that Toby was passed out. She said knew that we had been drinking and could smell the wine on my breath when we were wrestling. I immediately began apologizing and she said not to worry about it, Toby drinks on weekends and invites his friends over to do the same.
She walked over to the mats, still wearing her bath robe and I was in total shock when she removed it. She was wearing a white thong and had changed into a thin sports bra. I could see her nipples sticking out in her bra and the outline of her dark pubic patch through her thong. Unreal.
She kneeled down on the mats, we locked up and the match was on. We struggled against each other and my boner immediately sprang to life from the body contact. We were going for the takedown on each other when we fell to our sides, and I'll be damned if she didn't get that same body scissors on me again, only this time we were skin to skin, her bare thighs were wrapped around my stomach like a boa constrictor. On our sides, facing each other, her nipples were sticking straight out of her sports bra. I was struggling to escape when she pulled me in and our lips barely touched. This time I didn't pull away.
My speedo slid down just slightly during the takedown and I suddenly felt the top of my boner pressed against skin. My boner was pressed against her thigh. Our lips were still lightly pressing when she decided to rewrap her body scissors on me and when she set the body scissors in place again, my cock was pinned tight against the front of her thong. It almost felt like I was pinned against a bed because my shaft was tight against her and nustled against her soft, thong covered mound. We layed like this for several minutes before she suddenly rolled to her back, taking me with her and keeping the body scissors in place.
I was laying on top of her now when she quickly changed the scissors into a figure 4 body scissors, locking herself even tighter around me. I tried to look down at my cock, but we were so tight against each other I couldn't see down that far. I could hear her grunting lightly, so I layed my upper body against hers and dropped my head on her shoulder, my mouth near her ear. I began lightly grunting too with my chest pinned against her hard, sports bra covered nipples. M had her thighs wrapped around me well, and even though we were both starting to perspire, I couldn't wiggle my way out. Not sure what to do next, I wrapped my arms around her neck, trying to gain some control of her upper body. I could hear her grunting when all of a sudden she lifted her hips up and pressed herself even tighter against me, using the figure 4 to her advantage. She was continuing her grunting as she would increase the pressure and then let up, pressure and release, etc. My cock was going crazy rubbing against the front of her thong when she rolled us again, to our sides and then rolled me to my back, pinning me. She released the scissors when she gained the straddle, but was able to mount herself on my skinny hips to prevent me from wrestling free. She spread her thighs for leverage and I could feel her inner thighs gripping my hips. She was in perfect pin position on top of me and slowly layed her body against mine, covering me and stretching herself out over my body. We were mostly skin to skin in this position and she had her tummy pinned over my exposed erection. She was laying tight over me, her head resting on my shoulder and I could hear her lightly grunting as I struggled underneath her, trying to wrestle free. I attempted to bridge, but with her position on top of me, I couldn't arch my back. My shoulders and back were pinned tight to the mats and I could barely move. She really had me pinned good. She was continuing to grunt, her mouth was near my ear and I could feel her warm breath on my ear when she asked for my submission. She had me and we both knew it. I submitted the pin to her. She began to release the pin and then asked if I wanted to wrestle a mattress match upstairs. I asked what she meant and she said that she had a king size mattress upstairs in a spare bedroom that we could wrestle on. I said that sounded fine by me. She rolled to her knees and said “I guess the old lady can sill wrestle”. I smiled at her.
She grabbed her robe and put it on while while I tugged the front of my Speedo up and shoved my erection in diagonal to cover it up. She turned off the basement lights and I followed her up the steps.
It was now 1:00 a.m. And dark outside. There were just a couple of lights on in the house and she turned them off as we passed by them.
The spare bedroom was small and there was a king size bed in the middle of the room, with a sheet over it. She turned the ceiling fan on, dimmed the lights and closed the door. I was about to have my first mattress wrestling match....against my friends Mom.