Anal game

My boyfriend keeps wanting to have anal sex with me. My big concern is it being painful so I have been semi successful in evading the situation but he keeps hounding me about it. I think I finally have come up with a solution.

“I’ve been thinking, Babe”, I said to Jon. “You keep wanting to butt fuck me and I think I found a way for some anal sex to happen.”

“Go on, Jess”, he said with some interest.

“Well, we are both very competitive. So, I was thinking of a contest and whoever wins gets to have anal sex.”

“OK. Wait, what do you mean by that”? I could tell he was a little confused with the way I put it.

“The contest is wrestling. We can take the car out of the garage and spread out an old carpet for
padding and a blue tarp on top. Then we oil each other up. If you manage to hold me down and get
your fat cock up my ass and cum then you win.” I told him.

“Cool. I can do that.”

“But I will be wearing a strap-on and if I get that fat fake cock up your ass and I cum from fucking you then I win.” I laughed wondering if he would actually accept this offer.

Jon just stood there and stared at me. I could see he was calculating the odds before he finally
accepted. Wow, I wasn’t sure if I was happy or afraid that he accepted. He must want it really bad if he was willing to risk me fucking him. Now I had to go out and buy a strap on for the occasion.

We decided to wait until Saturday to do this. That morning Jon took the car out and we moved the few things we had in there into the utility room that was adjacent. After sweeping we pulled out these two old rugs that were rolled up and not in use. The two of them were a little larger than the single car garage but instead of over lapping them we let them rid up the walls a little. Then we placed a couple of big blue tarps over everything. We also placed some pillows in large black trash bags around the steps and a few other areas so no one hurts themselves.

The rules were pretty simple. We oil ourselves up and we also added some lube to each other’s assholes to make it easier and less painful. We had Siri set a 20-minute timer to wrestle and then a 3-minute break in between. When the 20 minutes were up wrestling would stop and if you were actually inside someone you had to pull out immediately. After the 3-minute timer went off we would start with both of us standing. To win you had to have an orgasm while fucking. I also promised not to fake one.

Also, no hair pulling, punching, kicking, biting, etc. You could spank someone’s ass but not in the crotch or tits. You could lick or suck.

Jon is thin and muscular and about 1” taller than my 5’7”. He is about 5-10 pounds heavier. He has a nice 6.5” dick. Not too fat that it is uncomfortable but he does have nice big balls. I am similar to Jon in size but with a C cup. Nice dark nipples that stick out. My strap on was about 7” long and about the same width as Jon. It was the soft fleshy kind so it wouldn’t hurt anyone. It had a little dick that stuck into my pussy with a spot that would rub my clit nicely when I started to fuck. A belt with Velcro attachment was used to hold it in place.

So, we stripped down inside and went out to the garage. We each had a bottle of baby oil to smear on ourselves. I made sure I was well coated so he would not be able to get a good hold on me. He looked good coated in oil. When we were both ready and my phone was on the top step, I called out to Siri to start the timer.

We both started to circle each other with a little bit of banter going on. There were a few fake lunges and grabs before Jon dropped to his knees and grabbed my legs below my knees. I decided to push off his shoulders over him thinking that I would just slip out and hop over. It kind of worked. I slipped out and then slid down his oiled back and laid face first on the mat.

Jon quickly turned around and threw himself on me and slid up to far so I slithered away from him. Damn, this was harder than I thought. I tried to crawl up on to him and he rolled over so we were facing each other. He managed to keep pulling me so I rolled over and he got on top of me with his legs outside of mine.

Jon held my shoulders down while he pushed forward while pushing himself in an upright position. This allowed him to straddle my chest like he was going to titty fuck me but he moved forward more and tried to push his dick into my mouth. I stopped him from doing that while struggling to get loose but then I thought I would let it slip in and suck him for a bit. I was thinking that he may get distracted and then I could push him off.

After fucking my mouth a bit, I noticed that he was not as in control as he was before so I pushed off to the side and knocked him on to his back. I quickly got on top of him and started to poke my dildo at his mouth. I managed to get inside of his mouth and started to fuck his face like he did mine. The thing is that this wasn’t doing much for me so I wasn’t distracted.

I was trying to figure out how to get him in a better position. Ideally on his stomach so I can fuck him from behind. I need to slide down and roll him over. Not easy since he would be fighting. Maybe I could slide down and pull his legs up and get him from the front.

As I was trying to figure out my next plans, he managed to pick a leg up high enough to wrap around my head and pull me backwards. He quickly sat up to get me as I tried to slide forward. He managed to grab and ankle good enough to pull me back so my butt was up against his crotch. I thought he was going to
push me down and get on my back so I pushed up and back but he started to pick me up with one hand. I easily went up so I tried to come back down at the same time he let me come down and I ended up with his cock in my ass. I could feel one of his hands was holding it up at the right position. My weight and gravity along with the lubricant caused it to slide all the way in.

I was startled. It didn’t really hurt but I definitely filled full. I had paused for a couple of seconds but Jon didn’t. He started to fuck up at me while I was basically sitting on him. It felt good but I wasn’t going to let him win. He might have gotten the first point but I was going to win the game.

I let him fuck me for about a minute before I made my move. I rolled to the side pulling him with me but slid out from under him before he was on top. I then rolled back on top of him. I hooked both of my legs around his and my arms around his arms, holding his wrist. I then pulled my arms and legs out to make him spread eagle. As he tried to buck me off, I angled my pelvis and thrust him fake cock up into his ass.

He yelped as I entered and then moaned as I went all the way in. I started to fuck him as hard as he did me. He grunted and moaned but was starting to struggle less. I started to fuck him harder as it was rubbing against me clit nicely.

He started to buck harder but that was only making it feel better for me. I really don’t think he was trying to get me off, so to speak, it was more like he was fucking me back. Kind of like when he takes me in the doggy position. This whole situation was very intense and I came hard and fast, grinding my big dick into his once virgin ass. He let out a loud grunting moan.

After a moment of neither of us moving I pulled out and rolled to my side facing him. He rolled over to his side facing me as well. I looked down at his cock. I was ready to give in and have him fuck my ass but I saw his cum over his cock and stomach. He must have cum when I did.

“That was fun,” I said. “It looks like you enjoyed it as well.” I bent down to clean off his cock with my tongue. “I guess you want a rematch next weekend.” He could only moan his consent as I swallowed his softening cock. The timer went off. It was hard to believe that this all happened in under 20 minutes but I guess we were both horny.

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