I have known Tom for many years. I have always been attracted to him, always wondering what it would be like to suck his cock. I have had opportunities, like the time he was staying in my house and I came out of the bedroom, he was in obviously jerking of because he very quickly acted as nothing was going on when I entered the room. I pretended as if I hadn’t seen anything.
Another time I caught him peeking as I was taking a piss. I have always suspected that I could seduce him but I have always chickened out, never quite knowing how to approach him. He is a good-looking guy. About 6 foot 2, 200 pounds. He always has a great tan and blond hair.
Over the years, we have stayed close. We are both married and our wives get along. We got into a weekly routine, every Friday night we played poker with two other friends. One particular night my wife had gone out of town with the kids to visit her mother. She was going to be gone until Sunday.
All the guys arrived and we had a good game going. We played late into the night. Most of the guys left around 11 pm. Since the wife was out of town, Tom decided to spend the night.
“Hey Matt do you still have any pornos?”
“Nah, the wife made get rid of them.
“Let’s go rent a couple of videos.”
We headed to the local porn shop and started to look for some videos. Tom picked out a couple and so did I. But I made sure that one of the videos was bi.
I had a big screen T.V. in the family room and I popped in a porno. The usual stuff, girl meets boy, boy screws girl. Girl then screws other girl. We both sat back and enjoyed the movie. We were both playing with our groins as the action heated up.
When the movie finished he said. “Pop another one in.”
I put another video in and it was the same kind of stuff, big blond is fucked by a couple of guys. I looked over at Tom and he was really playing with his groin through his jeans. When that movie was done, I popped in my video.
It started out normal. A girl moves into an apartment and meets her two handsome neighbors. After a getting to know you section the girl ends up in bed with one of the neighbors and she is giving him a blowjob.
The other neighbor walks in, takes his clothes of and lies down next to the girl as she is sucking his friends cock. She looks up, smiles at him, and pushes the cock she is sucking toward the roommate. He lets his tongue lick his roommate’s cock and then sucks it into his mouth.
At this point, I look over at Tom and he has an incredible bulge growing in his pants. He looks at me and I shrug my shoulders as if to say. Hey, I didn’t know it was this kind of film. We continue watching it and Tom says.
“Man I can’t believe we are watching this.”
“I know what you mean I feel like I should turn it off but it is exciting to watch. Should I turn it off?
“Nah leave it on, I want to see what they do.”
We watched one guy fuck the other and I said. “Man that has got to hurt. How can they take that big cock up there ass?”
“Shit Matt haven’t you ever fucked a girl in the ass?
“It is all in the preparation.”
“Shit I don’t know man it looks like it hurts like a motherfucker.”
“Shit I have fucked a lot of girls in the ass, I know if I prepared you well I could fuck your ass and you would love it.”
“Ha! Well I guess we will never know that. No cock is going near my ass.”
I said this knowing that is what I really wanted. But I had to make Tom think I was all-macho. In fact, I was hoping to turn it into a challenge.
Finally, Tom said. “Well I am going to bed and jerk off, all this talk has made me very horny, see you tomorrow.”
We played basketball all day and later on Tom suggested we play poker.
“Shit man poker is no fun with just two people.”
“Well there is nothing else to do.”
“Okay deal the cards.”
Tom was having a bad night; he had lost almost all his money to me. We had a good hand going and he bet everything he had. He must have thought he had a great hand. I knew I had a good hand and this was the opening I had been waiting for all night. I checked his bet and I raised him 20 dollars.
“Damn Matt, you got all my money. Let me owe you.”
“No fucking way, you know the rules, you have to anti up or you forfeit.”
“Come on man. One time. Shit your afraid I have a better hand.”
“Tell you what, I will spot you the twenty, but if you lose you have to give me the shirt of your back.”
“Shit it’s a deal….here you go sucker pay up.”
Tom laid down a full house jacks over fives.
I laughed as I laid down my hand kings over aces.
“Son of a bitch.”
As Tom took his shirt off, he said. “Come on man give me another chance.”
“What are you saying?”
“Come on I need another chance to win my money back and my shirt.”
“What do you have to bet?”
“I don’t know I will mow your lawn if I lose.”
“Mow my fucking lawn that’s no fun. How about every time you lose you have to take off a piece of clothing. I want to see you embarrassed you fucker for all the times you have embarrassed me.”
“Fine, let’s go before I change my mind.”
I laughed at him and said. “Boy this is going to be fun; I am going to enjoy winning all the clothes off your body.”
What Tom didn’t know I was playing cards with a marked deck. I had him just were I wanted him. Tom proceeded to loose hand after hand. He kept cursing; he couldn’t believe his bad luck. As I laid the hand down I said “okay Tom give me your pants.”
Tom took of his pants; he was down to his underwear. I dealt the next hand. Tom was all excited I had dealt him four queens.
“Hey Mr. big shot, how about we up the anti?”
“To what? I already have almost all your clothes. All that is left is your underwear.”
“How about if I win I get all my clothes back and I bet you a hundred dollars on top of that.”
“You must have a pretty good hand to be so cocky. What if you lose what do I get?”
“What do you want?”
“Hmmm that is a lot I am giving up. Considering you have lost everything. How about if you lose you have to be my slave until tomorrow. If I say jump you say how high.”
“You got it big mouth.”
“I am serious if I win you gotta do whatever I say.”
Okay…okay I promise. Besides I have nothing to worry about there is no way you are going to beat my hand.”
“So do we have a deal?”
“Yeah…. Yeah… Show me your hand.”
I flipped over and showed him my four kings. His jaw dropped.
“Son of a bitch…”
“Okay Tom you lose the underwear.”
Tom was so dejected, he dropped his underwear and a nice soft cock appeared in front of my eyes.
“Okay go to the kitchen and get us a couple of beers slave!”
As Tom walked away, I said. “Nice ass hahaha.”
Tom turned around and sneered back at me.
He came back into the room and I was sitting on the sofa. “Hey Tom push play and play that last porno again.”
Tom sat on the other side of the couch and we started to watch the porno. As the girl sucked the guys cock, I looked over at Tom and he was already hard.
“Hey Tommy are you enjoying the movie?”
“Well what do you expect? Hey, it is not fair. I am naked and you’re not.”
“Don’t worry I will join you in a minute. I am just enjoying watching you squirm … Hahaha. Hey don’t worry about it, if you need to jerk off go ahead.”
“Nah that’s okay.”
“You don’t understand… I said play with your cock.”
“Shit man your one big time fucker. I won’t forget this.”
“Promises…..promises. Now start jerking off.”
I watched Tom play with his cock. He had a beautiful cock. He was about 8 inches long not to wide but a real nice mushroom head. He was really getting into it, and when the other guy started to suck his roommates cock
I said. “Hey that looks good, what don’t you come over here and take my jeans off and suck my cock too.”
“No fucking way!”
“Hey did you forget our little bet.”
I stood up and Tom unbuckled my pants and lowered them. I then told him to take off my underwear with his mouth and not his hands. So I felt his mouth take a hold of my underwear and start to pull it down. My cock sprung out and hit him in the forehead. I heard him gasp. He had never seen my cock. My cock was a full nine inches but what made him gasp was how thick I was. My cock is seven inches in circumference and uncut.
“Put your hands on my hips; only use your mouth on my cock.”
I looked down and watch Tom’s tongue lick up my shaft. He licked my head as it protruded from my foreskin.
“Oh yeah lick it Tom.”
He licked it up and down.
“Open your mouth and suck it Tom;”
Tom let my cock slip into his mouth, I grabbed his hair and fuck faced him.
“Oh yeah Tommy your mouth feels so fucking hot. Are you sure you never sucked a cock before?”
I watched him shake his head no, as he sucked my cock. I couldn’t believe I was watching my best friend sucking my cock. I pulled my cock out of his mouth and sat on the sofa.
“Come kneel before and suck it Tom.”
I watched him crawl over to me, took my cock into his hands, and started to lick the head. Then he let my cock slip into my mouth and suck it in deep. He was really getting into it. I was getting close to cumming.
“Oh yeah Tom suck it faster I am about to cum, I want you to take it in your mouth.”
I couldn’t take it anymore and I started to cum in his mouth, I grabbed the back of his head and pumped all my cum into his mouth.
“Oh fuck yeahhhhhhhhhhhhhhhh take it all Tom swallow it ohhhhhhhhhhhhh.”
He kept sucking it, until all the cum had left my body.
“Damn man you’re a good cocksucker.”
“Okay we are even now, I am going home.”
“You’re not going anywhere. The bet was for the weekend. We’re just getting started.”
“Fuck you; I already sucked your cock man.”
“Hey you made the bet, now live with it. Tell you what I will give you a break. Let’s jump into the Jacuzzi and relax.”
We both got into the Jacuzzi. The water felt good. I was getting horny again and sat up on the edge of the Jacuzzi. I didn’t have to say anything. Tom knew what I wanted. He came over, took the cock in his hand, and stroked it slowly. Watching my head disappear and reappear as he played with it.
His pretense of objecting was over. He was enjoying this as much as I was. I watched him suck my cock until I came again, this time when I started to cum he pulled his mouth away and pumped my cum onto his face. It was so cool watching my cum splash his cheeks and lips. Then re rubbed the cum onto his face with my cock.
I was so horny that I told him to sit up and I moved to him and took his cock into my hands. I marveled at its beauty. It was so different from mine. I played with it looking at the mushroom head. I bent down and let my tongue flick the head. It felt strange but also amazing. I let just the head slip between my lips. My lips could feel the velvety head slip past them and into my mouth. I stroked his cock deeper into my mouth when I felt Tom’s hand grab my hair.
“Fuck yeah suck it Matt, damn this feels great. Suck it deep man.”
Tom was so horny he started to cum. I felt the first wave of cum hit the back of my throat.
It tasted a little weird, salty and bitter and it was hotter than I had expected. However, at the end of the day. I enjoyed feeling his cum in my mouth. I felt the power of making this man cum. I enjoyed the fact that I could make my best friend feel so good and I enjoyed tasting his cum. I swallowed as much as I could but some of it trickled out of the sides of my lips. He had way too much cum for me to swallow it all.
I kept pumping his cock until it got soft in my mouth. As I backed away. Tom said. “Damn Man that was hot.”
“So are you saying your okay with this now?”
“Hell yeah…you can suck my cock anytime you want buddy.”
“Good Because I plan on sucking you cock a lot and you are going to be sucking mine just as much. In fact I am horny again.”
“Cool bring your cock over here.”
“Nah I have a better idea.”
I got out of the water and came back with a bottle of baby oil.
“Hey no fucking way man. You are not going to fuck my ass.”
“Yes I am… did you forget our bet.”
“I don’t care. Your cock is way too big.”
“Tell you what, if you promise to make a good effort to try I will take it slow and if you don’t want to I will stop.”
“Okay I can handle that.”
“Stand up and bend over the side.”
I watched Tom’s pretty bubble but exposed to me and I poured some baby oil and watched the oil slide down his crack. I massaged the oil all over his butt. I enjoyed rubbing it in, and Tom seemed to be enjoying it too.
He seemed to like having someone else in control. I rubbed my forefinger all over his hole and slowly pushed it in past the first knuckle. I felt him gasp as I pushed it further into his ass. I went slowly and gently. I started to fuck him with my finger making a point to rub his prostate.
“Oh shit man that feels good, keep it up.”
I pushed a second finger in. Then I pulled them out and soaked my cock with oil. I also squirted his ass again and I grabbed my cock, put the head at the entrance, and slowly pushed the head in.
“Oh shit man that fucking hurts pull it out…shit PULL IT OUT MAN!”
“Tom you have to trust me, just relax, and stop trying to push my cock out. Let your ass muscles relax. Believe me the pain will subside and it will start to feel as good as my fingers did.”
“Okay… okay I am trying but shit man your cock is so fucking big.”
It was comical. Here I was standing behind my friend with the head of my cock shoved in his ass, this big strapping hulk of m man was whimpering like a girl.
Finally, Tom relaxed his ass, the pain subsided, and I slowly pushed more of my cock into his ass.
I grabbed his hips and shoved the rest of my cock until I had impaled my cock inside him. He raised his feet of the Jacuzzi floor as I shoved my cock in.
“Oh man your ass is so tight. It feels fucking great.”
“Your cock feels like a huge beer can up my ass but I am getting use to it.”
I felt Tom squirming his ass on my cock, wiggling it. He was really getting into it.
I started to slowly pull my cock almost all the way out and push it back in. I watched Tom grab the sides of the Jacuzzi as I pumped his ass. We had a good rhythm going. I was enjoying fucking my best friend’s ass. I started to feel my legs weaken and I told him I was about to cum.
Tom started to push his ass back into my cock faster as I fucked him harder.
“OHHHHHHHHHHHHHHHHHHHHHHHHHHHHH” I started to cum inside Tom’s virgin ass. I pumped my seed deeper and deeper into his ass and Tom loved every minute of it.
I finally stopped cumming but Tom kept trying to squeeze every drop of cum out of me. My head was really getting sensitive so I slowly pulled it out of his ass. I watched the gaping hole I left behind and saw my cum leaking out of his ass.
“Man you are one hot fuck. I loved fucking your ass.”
“So when do I get to fuck you.”
“Not here lets get out and go to my bed.”
We got out of the Jacuzzi and we dried each other’s bodies. We walked into to my bedroom and I told Tom to lie down on the bed. I crawled up to his cock and started to lick his balls and the stem of his cock. I licked the shaft up and down and finally I licked the head. I slowly sucked it into my mouth.
I then reached over and grabbed the baby oil; I pulled my mouth away and let the oil drip down his cock. I stroked his cock until it was super hard. I then raised my self over his cock and I pointed his cock as I slowly descended on it.
I felt his cock at my entrance; he was trying to push it in. I lowered my ass and I felt it slip in, just the head. I held my ass still as I got use to the feeling. I was very glad his cock was a lot slimmer than mine was, I couldn’t imagine how he took all my cock. Finally, when my ass had relaxed enough I let go and dropped my ass down until his whole cock was buried in my ass.
I never felt fuller. So this is what a girl felt like. I enjoyed the feeling. I liked being fucked. I was bouncing up and down on his cock.
“Man your ass is so tight”
“Well you cock feels amazing.”
“Man I can fuck you all night long if you let me. I can’t believe we have never don e this before.”
“Well I guess we will have to make up for lost time.”
I kept pumping his cock and when I felt him ready to cum I bent down and frenched kissed him. He was cumming in my ass as I kissed him. It was amazing to feel his cum enter my ass as our tongues played with each other. It was so intense, that he his tongue froze as he pumped his cum into me. I pulled my face away and rotated my ass to grab every drop of cum out of his cock.
“Wow that was amazing.”
“Yes it was, now I am horny again. I want to fuck your ass again.”
I lay down behind Tom and rubbed my cock all over his ass, and then I slowly pushed it in. It went in much easier this time. His ass seemed to open up, grab my cock, and pull it in. I slowly fucked his ass, taking the time to really enjoy fucking him. I reached over, grabbed his cock, and stroked him. I kept jerking him off until I had him cumming. He exploded all over the bed sheet. That set me off and I erupted inside of his ass.
We were both so tired that we fell asleep with my cock buried inside of his ass. I woke up in the middle of the night. My cock had slipped out and cum was leaking out of his ass. I rubbed my cock up and down his crack and I slowly pushed the head back into his ass. It went in so easily, it was amazing Tom’s ass was getting use to my cock.
He woke up as I slowly fucked him. I pulled out and pushed him down on his back. I put his legs on my shoulders, aimed my cock and pushed it back into his ass. I started to fuck him hard and fast. We had been fucking so long my sweat was dropping down from my face onto his. I was giving him a royal fucking. We looked down and watched my cock disappearing into his ass. It was mesmerizing watching my cock reappear and disappear.
I felt the cum erupting from my balls making its way out of my cock and exploding inside Tom’s ass. I kept pumping. He grabbed my ass cheeks and pulled me in deeper. Tom was trying to squeeze every bit of cum out of my cock.
I finally collapsed on top of him. “OH shit man that was incredible.”
“I never thought I would love being fucked so much.”
“We gotta do this again buddy.”
“Don’t worry I intend to fuck you as often as I can. We can tell the wives we want go fishing and we can fuck all next weekend. After that we will figure something out.”
Tom and I spent the day in bed fucking and sucking. Tom finally got dressed and went home. Just in time before my wife got home with the kids. I couldn’t believe it had worked out so well and I couldn’t wait for a repeat performance.
Let me know what you think of my story and don’t forget to vote. I also love to hear from the readers about their fantasies. Thanks for reading my stories and for the compliments. I had only intended to write one story when all this started but your inputs keep me going.