Real Estate Entanglements Pt. 03

I didn't sleep that evening. How could I? All I could do was toss and turn in my bed and think about Randy. I knew I was falling for him and I also knew what an incredible mistake it was to fall in love with the man so quickly. Sure -- we had been intimate -- for the sake of a wrestling match. I had been just as "intimate" with plenty of other guys and never grew attached to them as anything more than opponents. I was certain these feelings were just because I was feeling bad about my recent break-up, or because I was lonely and in a new area, or maybe because Randy was sexy but also had qualities that most other guys I had wrestled didn't possess.

I lay there in my bed trying everything I could to clear my mind and go to sleep. I watched television, read a book, I even stripped myself naked and spread out across my bed rubbing my cock and fantasizing that it was Randy -- but I stopped myself before I unloaded -- I wanted to have a decent showing in case Randy was able to take the title from me tomorrow night.

The night went on and finally the sun was illuminating the sky and I was just as restless and exhausted as when I had gone to bed. I toyed with the idea of calling in sick to work but I decided against it -- not a good impression to make when I had only been there a few weeks. So I showered and shaved and dressed and as I was getting ready to walk out the door my cell phone began to ring. It was Randy. My heart sank -- afraid he was going to cancel our match this evening -- even though it might have been for the best considering how exhausted I was going to be.

I picked up the phone and said hello and he said "would you like to meet me for lunch this afternoon?" I wondered what this meeting was going to be about but I just said I would meet him and later that afternoon I was seated across from him picking at a hearts of endive salad with an unsweetened iced tea I hadn't even touched. Our conversation was civil -- at best. We asked each other how our days were going and he told me I looked like I wasn't feeling well, which was the truth.

"We can postpone tonight, if you don't feel up to it?" I could tell he was disappointed at the idea of putting off tonight but I could also tell that he sincerely would be okay to wait. I shook my head and said I just needed some sleep and I would be fine. I was heading home after lunch anyway -- a half a day was better than nothing -- and I would be "ready to go" for seven o'clock.

We picked at our food a little more and there was no conversation at all until he put his fork down and said "I need to tell you something."

"Fuck" I thought. "Here it comes. Some terrible revelation that would probably make me despise him." I braced myself and waited for his admission but he casually sipped his iced tea and said "when we wrestle tonight, I want it to be the greatest match you and I have ever had."

"Okay," I said. "No pressure on either one of us."

"What I mean is, I want to do whatever we want to do. I don't care what it is. Anything you've ever wanted to do in a match but were afraid to ask because you thought it might be too weird or because your opponent told you 'absolutely no way.'"

I'll admit -- I've had some strange requests over the years. Some of my opponents have had some very unusual "kinks" when it came to their fighting. There was the guy who wanted to wrestle with knives -- not prop knives or plastic toys -- real, sharp, lethal knives. I politely told him where he could stick his knife and never contacted him again. There was the guy who wanted to tie the loser up and defecate all over him. I told him I was all out of rope and ended that conversation quickly. There was even a guy who wanted to wrestle wearing nothing but pantyhose. I had even considered that one -- it seemed harmless and I wondered if it might be kind of arousing (albeit a little strange) but when he insisted that his wife was going to watch us and that she wanted to keep the pantyhose we wore ... it got a little too weird for me to agree with.

I looked at Randy and said "what kind of things are you talking about?"

"Like costumes ... or props ... or setting up a scene between the two of us to play out. Whatever you want to do. So long as it doesn't break our rule of no injuries or pain -- I want you to know that I would be willing to try it."

I couldn't think of anything to say so I took my iced tea and drank some of it, hoping Randy wouldn't realize that I was stalling.

"Or we don't have to do anything ... I just wanted to suggest it in case you ..."

I cut him off mid-sentence with "do you have something to suggest?"

He smiles at me. "Well ... I have this Tarzan loincloth that I've been dying to wear!"

"You didn't have to ask my permission to wear a loincloth," I said as I tried not to fantasize about his body wearing nothing but a loincloth -- but I could not clear the image from my head and as a result my cock, knowing a good thing, started to grow hard.

"I have a costume I'd like you to wear, if you would?" he asked.

"A gorilla suit?" I asked and he laughed, almost choking on his food. He swallowed and said "no! It's a special kind of underwear. I think it's called a "sock" or something. It has a waistband and just wraps around your cock and balls."

"Real easy to take off of me, I guess?"

"I forgot to mention that my loincloth doesn't have anything underneath it -- just two flaps that barely cover my front and backside."

My cock was swelling now. I wasn't going to be able to stand up for a while so it was a good thing we were still eating. He swallowed some iced tea and took a breath before he said "and ... finally ... since tonight is such an important match for both of us -- I'd like there to be stakes."

"Stakes? What kind of stakes?" I asked.

"Well ..." he was about to speak when our sexy twenty-three year old waiter came over to ask if we wanted anything else. He was wearing a small apron in front of his pants and I wanted to remember to ask Randy if his loincloth was smaller than that. We both smiled and said "no" and he walked away.

"Yes," Randy said.

"Yes?" I asked.

"Yes, my loincloth is smaller than his apron."

I slapped my hand on the table, jangling the silverware and said "can you read my mind?"

"No," he said with a grin "but I can read the way your eyes were checking out our waiter."

"I wasn't the only one checking him out ... and since he's not here let's get back to those 'stakes' you were talking about?"

He took another sip of iced tea. "This is what I had in mind. We wrestle to earn three points to determine who the winner is. The first point is a submission. The second point is an erotic submission."

"You mean first to cum?"

"No, the second point is by a submission we get by doing something erotic to the other. Working over his erogenous zones until he can't take it anymore."

The more I thought about this second "point" the more I liked it.

"Okay," I said. "And the third point?"

"Making your opponent cum, of course. So, I figure after all that the winner of the match is going to be frustrated and horny and ready to blow ... so ... I suggest ... if you're okay with it ... that the winner fucks the loser?"

I thought about this for a moment. I had to let it sink it. In all the wrestling matches I have had only three other guys had ever suggested we have sex after the match. I had agreed to only one of them and after we wrestled (and he lost) he claimed he was too exhausted to do anything. I knew it had more to do with his being terrified of a man truly dominating him that way and he had been hoping it would be him "on top" but I wasn't about to force him into it, even though it had been his idea. I hadn't been interested enough in the other two guys to consider it so I said "no" and we just wrestled and played. Nobody had ever brought it up again ... until now ... and "now" it was from a man who had kept me awake all night because I believed I was falling for him and now ...

"You're not saying anything" Randy finally said, snapping me from my thoughts.

"I know ... I'm sorry."

"No, I think I should be the one who is sorry. I shouldn't have suggested something like that when we ..."

"Yes," I said without letting my brain have any more time to toss around the fears I had. "Let's wrestle for stakes tonight. Everything you said ... it's fine with me."

He smiled and said "what about you? Any fetishes or fantasies you want to explore?"

"Yes" I said as I finished the last of my iced tea. "I want to wear the loincloth and you wear the sock thing."

Randy seemed pleased with this suggestion. Very pleased. He smiled and finished his iced tea and we finished the remainder of our lunch in silence. I went home and undressed and crawled into bed, and rolled over onto my stomach and fell asleep after only a few moments. Perhaps it was in anticipation of the night ahead or just the exhaustion finally catching up with me -- but I slept until six o'clock and woke up feeling much better than I had before. I took a shower, dressed and headed over to meet Randy at the house for sale.

When I arrived I saw Randy's car in the driveway and pulled in next to it. I went up to the front door and was about to ring the bell when I saw a note taped over the buzzer which simply said "come in and go downstairs." I obeyed the instructions -- locking the door behind me -- and went to the basement. It was much more different tonight than it was yesterday. The bright fluorescent lights were off and only the small recessed lights in the corners were on -- dimly lighting the room. Candles were lit and placed along the wall by the wrestling mat. The stereo system was turned on but instead of the loud, thumping techno music of yesterday it was a soft, soulful jazz station. A saxophone was wailing sadly as I walked over to the wrestling mat where I could see a brown paper bag with my name written on it in black marker.

I picked up the bag and inside was the loincloth he had promised me. It was truly nothing more than a thin waistband and two flaps of leather that fell in the front and back of it. It would never have made it on the set of any "Tarzan" movie -- but it was definitely titillating and I was eager to try it on -- and hopefully not be wearing it for long.

Randy came out from the bathroom holding a bottle of wine and two glasses. He was wearing a black garment that was basically a strip of material around his waist and a small "sock" that wrapped neatly around his cock and balls. I couldn't help but stare at it and wondered how he was planning to keep this on him while we wrestled and -- even if we weren't wrestling -- how was it supposed to stay on him if he got aroused? There didn't seem to be enough material to contain his package now -- once it got hard I was certain this "outfit" was going to pop off of him like a balloon released after being inflated and flying around the room.

"You like?" he asked, showing me the front and back of his wrestling attire. I smiled and nodded as I held up the brown bag and said "I should go get into my costume."

"There's plenty of time for that" he said as he poured us each a glass of wine and handed me one.

"Wine, candlelight, and wrestling" I said with a little laugh. "This would be a perfect date for me if I thought we were on a date."

He sipped his wine and stared at me for a moment before he said "I was hoping to make it a little less antiseptic. Make this a little more ... enjoyable ... for the two of us. And maybe a little romantic, I admit. Especially with what we have planned for after the match."

I smiled, sipped my wine and headed towards the bathroom to change. "You're still okay with that?" he asked as I headed to go change.

"Of course," I said. I went into the bathroom and stripped from my clothing and pulled the loincloth up around my waist. The tiny patches of leather in the front and back barely covered me -- but that didn't really matter. I admired myself in the mirror, took a large sip of wine and went back into the basement.

Randy was already standing on the mat, adjusting the tiny pouch of an outfit so that it covered him a little more -- which still wasn't much. I finished my wine and set the glass on the floor before before I crossed towards him I stepped onto the mat. He looked up and down, not so much "sizing me up" as he was checking me out.

He nodded "that looks better on you than it does on me" he said, not taking his eyes off the flimsy bits of leather barely covering my cock and ass. I looked at his own package and scoffed "that's going to offer you much protection."

"I'm not looking to be protected for the match" he said. "That's for the winner and I have condoms for that." I couldn't help but continue to stare at his thick cock which seemed to grow larger as we spoke and -- as earlier -- my ass twitched a little ... only this time it was from it being a possibility. He reached his hand out and gently took my chin, lifting my face so that I was staring into his eyes again. "We're good with the three points rule? Submission ... erotic submission hold ... then first to cum." I nodded in agreement. "Then I guess that's it - so let's go?" he said as we moved up nose-to-nose and pressed our chests against each other, trying to stare each other down.

"There's no way I'm going to let you win this," I growled at him. "I have a reputation."

"In the west coast" he said. "You have to earn your title here on the east coast."

We locked up and began to grunt and growl against each other as we struggled for an opening -- but as we had wrestled twice already we both were more prepared for this round and neither of us were willing to give the other man the advantage. We pushed against each other but it was to no avail. Finally Randy leaned forward, his lips against my ear, and whispered "so you're not just going to hand over your ass to me tonight ... are you?"

I thought about it for a moment but decided to play strong - for now - and said "you'll have to do your best to win tonight!"

He purred into my ear "oh, I plan to give you everything I have." Just being here on the mat with him, feeling the heat from his body and his warm breath on my neck was making my already semi-erect cock stiffen and push aside the leathery fabric that barely covered it when I was flaccid.

Randy made the first move, freeing his hand and bringing it down and punching me in the side -- just above my hip. He wasn't putting enough pressure behind it to make me black and blue but it still hurt and I jerked to the side when he did it -- so he did it again and again.

"Are we boxing or wrestling?!" I moaned into his ear as he pulled me tightly against him with one arm behind my back and punched my ribs with the other. Before I realized what he was doing he had danced us up against the wall and forced me up against it. Damn! It was a slab of ice cold cement and I shrieked when I hit it. It didn't stop Randy from attacking. He had been punching my right side so he raised my right arm over my head and began rabbit punching my ribs. I buckled and gasped and coughed but he worked me over like a half a cow hanging in a meat locker.

When he had enough of this he let my arm drop -- it fell limp at my side -- and spun me around, forcing my chest and face into the cold wall. He held his arms against my upper back while he brought his thigh up into my lower back. Each time he struck I cried out and I knew I needed to get out of this predicament quickly ... my lower back was already starting to ache a bit from this and if he kept it up he might actually get me to give up.

But Randy let me go and moved to the side, allowing me to play my part and fall to my knees -- my hand to my backside and my head leaning up against the wall. It was exactly as he had hoped because he moved back to my side and pulled up on my arm -- securing it in a hammerlock as I knelt on the floor beside him pounding my free hand into the wall in frustration.

"Had enough, chump?" he said as he bent my arm back farther than I had ever thought it would go.

"NO!" I cried out, sounding a bit more desperate than I had wanted to. He dropped my arm and wedged his kneed into the small of my back, then wrapped his hands around my chin and pulled me backwards.

"No fair!" I shouted as my hats slapped the wall "I'm up against the ropes!"

"You're against the wall ... in an octagon this would be perfectly legal!" He dug his knee into the small of my back and yanked back on my upper body -- and I crawled and slapped at the wall in a desperate attempt to do something -- anything -- to escape from the predicament he had me in.

But Randy was not about to give up his advantage. He moved his knee to the side and his fists began to hit my lower back. With each punch I sputtered and whimpered, pressed up against the wall with nowhere to escape to, and then -- suddenly -- he stopped and leaned forward.

"Harder?" he said, sounding as if he hoped I would agree.

The side of my face may have been pressed against the wall but I was still able to smile and say "fuck yeah!" I had never been interested, or even excited, by punching before ... but now that I was trapped in this position and having him hit me all I wanted was for him to hit me a little harder.

His fist slammed into my lower back this time and I cried out, but instead of asking if I was okay he just kept punching the small of my back. We both knew what to say to make him stop ... and I knew that if I said our safe word he would stop instantly. But I didn't want him to stop. I wanted him to keep punching me. It was turning me on so much that my cock was as hard as it has ever been and jutted out from behind the loincloth with the head rubbing against the wall -- trapped along with the rest of me.

Randy stopped working over my back and sat down behind me, stretching his legs out on either side of my torso. His hands were still around my chin and he pulled us both backwards until he was on his back and I was laying on top of him and an instant later his legs snapped shut around me in a very tight bodyscissors.

"FUCK!" OH, FUCK!" I screamed as he squeezed his thighs together around my middle. I heard him whisper "yeah" as his muscular legs tensed and crushed me ... oh, God! He was seriously squeezing me harder than any man had every done in a wrestling match before and all I could do was lay there, on top of him, and look down at his legs wrapped around me. I reached down and tried to pry his legs from me but he wouldn't loosen the hold.

I was trapped between his legs for a few moments, squirming and panting and crying out in desperation ... and the whole time Randy just lay beneath me -- his arms on my shoulders to keep me still while his legs slowly decreased my waist size by an inch or two.

"Give?" he finally yelled. I tried to give him some bravado, I tried to touch and cocky but I couldn't speak. All I could do was shake my head "no."

"Well, good" he said with a sadistic cheerfulness. "I wouldn't want you to miss what I have planned next!"

He dropped his legs from around me and I quickly took in a deep breath and slid my ass to the mat. All I could feel was my bare ass on the mat as my loincloth had not only slid up my body a little but had rotated so that it offered no protection at all. I didn't think of adjusting it, I sat on the mat and held my sides while Randy got to his feet and stood up alongside me. He took my hair in his hand and yanked on it slightly, more to encourage than to hurt.

"On your feet, bitch!" he said as I groggily obliged. I got to my feet and he turned me towards him and with a cheerful "here we go" his arms were sliding around either side of my body and around my back. He pulled me into him tightly -- a bearhug I knew was not going to be easy to escape from. He squeezed, his muscular arms holding me firmly in place and not allowing me an inch to maneuver ... or even breath.