A Losing Hand in the End

It wasn't much of a day but the poker game that night turned it all upside down. It was a group of people I've played with before, I never really got deep into it but for some reason tonight I did and predictably it didn't go well. I was down nearly 500 dollars to the big winner which for a just getting by 25 year old grad student is a major chunk.

Ben is an undergraduate friend of a friend and had been in the game many times and he never won or lost big. But when things broke up we headed out walking in the same direction and I told him that it would take me a couple of months to even up with him.

Ben wasn't overly anxious saying, "You'll mange when you can." Then he said something odd, "Unless you'd like to write it off another way."

I looked over at him a bit unsure what that meant, I mean I wasn't going to kill anybody and he said, "If you'd like to stop by and have some hot man sex I'd forget about the money."

My first thought was actually, 'Am I 500 bucks attractive?' But as my mind raced while we continued to walk I started thinking about how the hottest sex I'd had with my girlfriend was a threesome with another girl and if she could go both ways why was I so reluctant? Ben was a good looking 21 year old guy, I'm sure he has plenty of chances, I remember him talking during the game about a girlfriend once or twice.

So after a million other things went through my mind in what was only about 15 seconds of silence I replied, "Seriously?"

Ben looked at me and said, "Yeah, you're big strapping guy Russell I think you could handle Big Ben. If you're up for a good time, it would just be the two of us, no need for spreading the word around."

Well that sounded good because I wasn't going to be telling anybody about something like this. Then I asked myself what was he talking about, Big Ben. Because Ben is a toned athletic blonde guy 5-11 tall and 180 pounds and I'm 6-3 tall and 245 pounds with black hair. Then it clicked what he was talking about and I thought, well whatever he's is packing Ben will be surprised to see my nine inches and we'll see about Big Ben.

So with my mind wide open and made up, and not wanting to be pinching every cent for six months I decided to go all in, "Well if you're up for it tonight's as good as any Ben."

"That's good for me Russell." Then he slapped me on the ass, "We'll do it up big time. My place is just around the corner."

So we headed to the bedroom and after stripping down Ben said, "Russell I think the first order of business would to give you a nice warm enema to relax you and make a clear path for the activities."

That didn't sound too unreasonable so we headed for the bathroom. As Ben was inserting the tube in my ass I was looking around and got my first real look at him. I don't know what made my head spin more the warm liquid going up my ass or the schlong dangling in front of Ben. Even soft it must have been seven inches and I got the meaning of Big Ben.

With me emptied out we headed back to the bedroom. I was getting a hard on from the warmth and thinking about Big Ben and Ben had been getting into the action because his dick was semi stiff and already impressive. I wasn't sure what the protocol was but I reached out to take Ben's cock in my hand and slowly began jerking him off.

He returned the favor and said, "This looks like a pleasure ride Russell you must be popular. Oh god you've got some big balls on you." As he took them in his other hand, "I just love big balls."

I continued to stroke Ben's cock which is thicker than mine and fuck had swelled to its full 12 inches. The head was huge and I was seriously impressed with the biggest cock I'd ever seen. "Damn I know what you were talking about when you said Big Ben. This thing is a club."

"I do enjoy it and I'm sure you will too Russell. I've known guys who could handle it better than some women but I think you're man enough to take it" said Ben.

We were both good and hard so Ben said, "OK Russell let's get you on all fours on the bed and I'll grease the way."

So I got up on all fours on the bed and Ben proceeded to work one then two fingers of lubricant in my ass. I was relaxed when Ben got a third finger in me and said, "Oh Russell do you feel ready?"

I just nodded silently and Ben said, "Yes you are. Now just hold on while I get this condom on and get myself lined up just right."

This was the longest ten seconds of my life as I waited and wondered what this was going to be like, why the fuck I was even here in this position, how much pain there would be, and a million other things. But what filled my head the most was the thrill of a new experience.

Climbing back on the bed Ben spread my ass cheeks and said, "I hope you're ready Russell because here we go."

Then he poked the head of his fat dick into my ass. I had my eyes closed but I swear they rolled up into my head from the initial shock and pain. But Ben had done a good job working with his hands and greasing me up because I was able to relax and enjoy in short order.

As Ben slowly pushed his big dick deeper into me he leaned forward and reached around to stroke my stiff nine inches, "Tell me you can keep that nice big cock hard so I can suck you off when I'm done back here Russell. Can you do that for me?"

Slightly out of breath I could only grunt a 'yeah' but damn right I was sure going to do my best to hold out and not just to do it for Ben who was alternating stroking my dick and playing with my balls.

Ben rubbed my ass cheek and said, "Thank you Russell you are very considerate. Now you get yourself set because it's time to really give your big butt a big banging."

And with that Ben continued to push deeper on every stroke and before long was pushing all 12 inches up my asshole and pounding against my big ass. I hope he was enjoying himself because I sure was especially feeling his balls slapping into mine as he drove forward. It was an awesome new experience having my ass stuffed for the first time especially with so much cock but fuck it was more than I could have ever imagined.

I was impressed that Ben had so much stamina and could hold back from cumming as he continued to ream me deep with that foot long. Finally he held my hips and pushed in all the way in before shooting his load buried to the balls in my ass. Fuck it was incredible.

Ben pulled out slowly and I just pitched forward face down on the bed. Ben rubbed my back then slapped me on the ass saying, "Oh come on Russell don't forget your promise. Roll over and let me at that big dick of yours."

So with a push from Ben I rolled over onto my back and he quickly dove between my legs and took my stiff dick in his mouth. Ben kissed the head of my dick then almost instantly took at least half of it between his lips. Damn I thought, this boy knows his stuff. In no time Ben's head was bobbing up and down as he held the base of my cock in his hand while slowly and methodically taking a little more of the shaft down his throat.

It was quite an enjoyable display of sucking cock and even more intense as Ben had an inch or so to go and began juggling my balls in his hand. Then when he went all the way and completely swallowed my nine inches and ever so slowly drew back until he only had the head in his mouth it would be hard to say who was enjoying himself more, me or Ben.

He repeated that move several times, while massaging my balls with both hands. That combination proved more than I could stand and I shot my load. Ben was actually humming as he held the head of my dick in his mouth and pumped the shaft with his hand, getting every last drop out of me.

Ben looked up between my legs with a big grin on his face. I rubbed the top of his blonde head and said, "Fuck you are the master."

Ben said 'Thank You." Then moved up and sat on my stomach and rubbed my chest with both hands. "Oh you are a man sized treat Russell on both ends. I hope I pleased you."

Looking up at Ben I could feel his big dick laying on my chest I replied, "Oh yes Ben I'm very pleased. This has been a completely new experience but it was awesome to say the least."

"Oh I'm so glad to hear that Russell. It was such a pleasure to fuck your big ass and to be able to suck your fat dick. You're fabulous"

Then I had a thought, "You know since you do like girls maybe I could talk to my girlfriend about a threesome. Noreen's a big girl if that's up your alley"

Ben smiled and said, "Yes I like the big girls the best Russell. If you think she would want to include me."

I rubbed Ben's thighs, "Oh she would find you much to her liking I do believe."

Seeing that Big Ben was starting to get hard I began stroking it and Ben said, "First time I doubt you could swallow much of that but I could sure go for a manly handjob."

"That sounds good to me." Was my reply and we stood up next to the bed and I put my arms around Ben's toned body and jerked him off with one hand and played with his balls with the other. Ben began grinding his sweaty firm body back into me so I held him tightly to me with my left arm and pumped his now stiff dick slowly with my right hand.

We were both groaning and I found it exhilarating holding Ben's huge dong in my hand, out bodies pressed tightly together. I sped up my motion and Ben said, quietly "Oh I'm going to cum. Would you like to swallow it?" It was not something I had ever thought about but if there was ever a night for breaking new ground I was having it so I hugged him and said, "I'm game."

So Ben spun around and I dropped to my knees. I was a bit stunned being head to head with Big Ben. I mean I had had in my hands and up my ass so knew it was big but it being right in my face it was imposing. But I took a deep breath, opened wide and got the head in my mouth just as Ben began to cum. I was preoccupied so Ben jerked himself off to keep things going.

Ben was very considerate and tilted my head a bit and I was able to keep almost everything in my mouth and swallow the salty shot. Damn, I thought, how much can this guy hold, because my mouth seemed to fill twice before Ben was spent.

Looking up at Ben I rubbed the backs of his thighs and said, "I guess this makes us even."

He laughed and patted the top of my head and said, "Oh we're good alright."

He suggested I get cleaned up and as I exited the bathroom dressed and worn out I said, "I'll let you know when Noreen and I can set a date to get together with you."

Ben kissed me on the cheek at the door and said, "Oh Russell I look forward to meeting Noreen and another incredible time."

After a life changing evening I couldn't wait to call Noreen and continue the changes.