A Bet's a Bet
This is a story of pure fiction. It involves people who are all of legal age and are willing participants giving their full consent.
Please let me know what you think of this story. You can send feedback to ericblair128@yahoo.com. And please consider consider donating to Nifty if you have the means. Thank you, and please enjoy.
A Bet's a Bet
I will never forget the worst loss of a bet I ever made. It happened on Super Bowl Sunday, February 5, 2017. The New England Patriots were taking on the Atlanta Falcons. It was going to be a hell of a game.
I was hosting a party at my house and one of my best friends, Mike, was coming over. He was a HUGE Patriots fan and always bragged about how many rings "Tom Terrific" has.
Due to this, when the Pats were in the Super Bowl, I always bet against the other team. It worked out well for me in the games against New York. I had a feeling about this game too.
When Mike walked in we had our greetings, then he looked at me and said his usual: "The usual bet? $20?"
Like I said I had a feeling about this game, so I decided to up the stakes: "How about $100?"
He gave me a surprised look, but his cockiness got the better of him: "Okay."
My feelings were getting better and better. At the end of the half, the Falcons were up 21 to 3. Mike looked perturbed, but tried to keep his composure: "Brady will come back. I have no doubt."
I was the one feeling cocky now: "Well, if you are so sure about it, maybe we can up the bet? How about $500?"
Mike felt a bit uneasy, I could tell, but he didn't want his confidence in Brady to falter: "Fine, $500"
The 3rd quarter passed and the Pats were now down 28-9. I was feeling really cocky now: "Still have faith in that comeback?"
Mike was pissed. His eyes were locked on the screen and refused to even look at me. He uttered a single syllable: "Yeah..."
"Well, how about we make it more interesting? How about double or nothing?"
This got Mike to look at me. "Double?"
"Yep, one thousand dollars if the Pats win."
He paused. He was seriously thinking about this. The commercials were almost over, and he took a deep breath and said: "Okay"
I was ecstatic, I started thinking about how I was going to spend all that money... then the fourth quarter happened.
The Pats put up 19 unanswered points and regulation ended with a tied game. The Super Bowl was going to overtime.
Now Mike was feeling cocky: "Still feeling good about this bet?"
I was in shock at what happened, I just replied: "Yeah."
"Want another double or nothing?"
"$2000?"
"Yep!"
I had to show that I was certain of the win and said: "Okay."
Overtime came and went insanely fast. Brady completed pass after pass and was in the end zone. The Falcons lost.
"YES! Ha ha ha!" Mike was screaming. I was busy wondering how the hell I was going to come up with the $2000.
Everyone was leaving. I said my goodbyes to my other guests. Now it was just me and Mike.
I couldn't even look at him. "I'll get you your money... got to give me some time though."
"I do have an idea. We can arrange another means of payment." He said.
I was desperate. There is no way I could pay $2000. "What is it?"
"My lover thinks you are really cute and would love to use you... sexually."
This caught me off guard, but I wanted to call his bluff. "You're okay with this?"
"Of course. We have an open relationship."
I looked at Mike and realized how good he looked. He was an insanely good looking. I never met his lover, but she had to be at least as hot. This made the choice easy: "sure"
"Great, my lover is almost here. Let's get you ready. Let's go to the family room. More room there."
My house was at the end of a cul de sac, so all of the windows provided great privacy. I was fine with this.
As soon as we got in there, he said: "Okay, go ahead and strip. My lover wants you naked upon arrival."
This confused me, but I was desperate to avoid paying that massive gambling loss. I took off my clothes and noticed something weird while I was doing it. Mike was looking at me. He wasn't just looking at me, it was almost like he was checking me out. I just pushed that out of my head and waited to see what insanely hot woman he was bedding. That was when the doorbell rang.
"Come on in!" Mike shouted.
Then in walked his lover and what I saw just about floored me...
HE WAS A MAN! Mike's lover was a man!
"You look surprised." Mike said. "You didn't know I liked men?"
I just slowly shook my head. I didn't know how to respond.
"Don't worry," his lover chimed in, "we'll ease you into it. And who knows, you just might find out how fun this can be"
As he said that he reached down and started fondling my balls. I freaked out from the surprise and swatted his hand away.
"Not ready to accept this?" Mike said to me, "It's alright, we have a way to make this easier for all of us."
Mike's lover disappeared. I wanted to run away and forget this whole thing, run away from my own house. However, I was in such a weird place mentally I was left paralyzed, just wanting to get this over with.
The lover came back and was hauling a weird barrel made of a pillow with four straps dragging behind it. It was placed on the ground, and Mike took me by the shoulders and pushed me over the barrel. His lover immediately grabbed my wrists and clasped them into two of the straps. At the same time I felt Mike grabbing my ankles and doing the same. Then I heard ratcheting and before I knew it, I was completely immobilized.
The lover tilted my head up towards him and looked down at me: "You ready for this?" I really did not want to owe this $2,000 but was so weirded out about what was going on. I was about to let two men have their way with me, and I was completely straight. All I could do was nod. He smiled down at me and said, "Well relax. You're going to love it."
The lover then looked up at Mike and said, "Why don't you get to work loosening him up. I'm going to get more comfortable."
At that moment, I heard a bottle snap open and some sort of liquid squirt. Then I felt one of Mike's hands set on my back and the other one move to my ass cheeks. His hand gently squeezed and massaged the cheeks with a firmness I never felt from a woman before. The hand gradually worked its way to the crack and then I felt a cold, wet finger start at my taint and slide up to my asshole.
I let out a weird grunt. I had never had a man touch me like that before and what was weirder is it wasn't as bad as I thought it was. His finger then began slowly moving around the rim of my asshole ins gentle circles and that was feeling kind of good. I then felt my cock begin to betray me, and Mike did not miss it. "Hey, Chris, I think he is starting to like this."
I looked at Chris and watched him as he started taking his clothes off. His body was surprisingly fit. He had a nice, firm build with a perfect V in his abs that led down to his hips. He kept his underwear on, but I saw a massive bulge in them. Chris caught me staring. "Like what you see? Maybe you're not as straight as you thought you were."
Chris then slowly moved up to me the bulge was not even an inch from my nose. I could smell a strong, manly musk coming from it that was surprisingly enticing, and Mike's continued manipulation and circling of my asshole was making the whole thing all the more intense. I couldn't believe how horny this was making me. Then Chris closed that final inch and my face buried into his bulge. It was incredible.
Chris pulled away and I found myself straining to get it back in my face. "Missing it already? Don't worry, you'll get plenty of intimate attention from it. We just need to make sure you are really ready for everything." At that, he pulled out a weird bottle and placed it under my nose it had a weird chemical smell.
"Breathe deep," Chris said to me. I took a deep breath and as I did I felt Mike move from circling my asshole to pushing his finger in to the first knuckle. My head was spinning and the feeling of my ass being invaded was intense. Then Mike started the circling again, inside my ass. I started groaning in the surprising pleasure of the feeling.
Chris moved his massive bulge back to my face and started rubbing it against me. I just groaned right into his bulge and felt that cock contained behind that thin layer of cloth get harder and harder. Chris then pulled away again and pulled his underwear down revealing a massive, veiny, uncut cock. He pulled the material under his balls to prop that monster up and looked at me. I couldn't look him in the eye this time I couldn't take my eyes off of his cock. It looked so delicious to me and I found my mouth (and cock) drooling uncontrollably. I never knew that a man could make me feel like this.
"Not yet," said Chris, "you still aren't ready yet." He placed that bottle under my nose again and I took another deep breath without prompting this time. Mike heard me take that breath and pushed his finger in further, to the second knuckle, and started the circles again, stretching my asshole further.
The whole feeling was intense I started involuntarily rubbing my cock against the material of the cushion barrel. I couldn't think of anything anymore except how horny I was.
Chris then moved his beautiful cock closer to my face and mouth. I opened it willingly and tried to get a taste. Chris kept teasing me moving it closer making me strain to get it then pulling away. "For a straight guy, you sure look hungry for cock. Beg me. Beg me to let you suck my big beautiful cock."
I couldn't even think in terms of gay or straight. All I could think of was that I wanted that cock in my mouth and would do anything to get it. "Please, may I suck your big beautiful cock."
"Please what?"
"Please... sir"
"Say it all, say what you want."
"Please sir, may I suck your big, beautiful cock."
At that, Chris placed it on my lower lip and pushed it in. I just started sucking on it hungrily. As I did Chris placed the bottle under my nose and I immediately took another deep breath. Mike pushed his finger in the rest of the way. The circling started back up and I was over the moon. My head was swimming so much at this moment I couldn't even tell you my own name.
I just kept moaning with this delicious monster pushing its way deeper and deeper into my mouth. It hit the back of my throat and I started gagging.
Chris pulled out and said, "Just relax, try swallowing as it goes in." Then pushed it back in. I gagged again, but a little less. I tried swallowing like he said and felt those thick veins rubbing against my tongue. Mike's finger just kept circling. Then I heard that bottle snap open and felt that cold liquid squirt into my ass along his finger. Then he pushed in a second finger. They both started those circles.
Chris's cock was getting harder and harder. I kept feeling it push deeper into my mouth easier and easier. My nose was now buried in his pubes. I just kept swallowing. This was all amazing. Mike moved on to entering digit number three. My cock was now much harder than it ever has been for any woman.
After about a minute of me still hungrily sucking on Chris's beautiful cock he pulled out.
"I am about ready to cum, but there is no way I am doing it in your little cock whore mouth." Chris said to me, "I want to break that little straight boy ass in and properly turn you into the fag you were always meant to be."
Mike pulled his fingers out my ass and it felt strangely empty. I found myself pushing back trying to find them again.
"Wow!" Mike said, "Is your little fagboy ass missing me already? Don't worry, you'll love this next part." At that he slapped both cheeks hard and I felt Chris assume the position behind me grabbing both of my hips. Mike walked in front of me and place that bottle back under my nose. As I took another deep breath, I felt it.
Chris's cock began sliding into my asshole. The fingering and stretching Mike performed made this process easy. With no resistance at all his cock bottomed out and I felt his pubes brush against my cheeks. I couldn't believe how fulfilled this made me feel. Chris then slowly pulled out until just the head was in then slammed all the way in again. This caused his cock to rub against my prostate and sent a shockwave of pleasure through my whole body.
Mike moved up to my face and began rubbing his cock against my nose through his pants. It was already hard. Chris's thrusts into me caused my face to mash deep into Mike's cock. He then slowly reached up and pulled down the zipper. Then slowly pulled out his cock.
It was beautiful too. He was cut and at least seven inches. It also had a slight upward curve that showed all of the ridges that ran along the shaft. My mouth was wide open from the pleasure I was getting from Chris's powerful anal invasion, and Mike took full advantage of this. He simply placed the head against my lower lip and began a violent face fucking.
This began the most intense sexual experience I ever participated in. Mike and Chris had me fully spit roasted. Their cocks were postponing into me growing with more and more intensity. This was causing my own ecstasy to reach greater and greater heights and I was feeling my own cock start to reach the edge of the most intense orgasm I ever felt. I just needed that final push.
I felt both cocks buried in me expand even more and I knew what that meant. Instantaneously, both cocks exploded with what felt like gallons of cum. I felt Chris's fill my bowels with it, and it was all I could do to keep up with swallowing Mike's. That was the final push I needed to have the most amazing, explosive orgasm I have ever felt.
As their cocks began to deflate they pulled out of me. Chris laughed as he looked down and saw the puddle of cum under me.
"Looks like he had a good time too," he joked to Mike.
"Yep, for a straight guy, you sure do make one hell of a cock hungry faggot," Mike said to me.
They both started putting themselves back together and, after cleaning it, carried the cushion barrel out of the house.
Mike came back in. I was still sitting in the living room. I had a lot to think about. "That was real fun," he said, "you ever want to do it again, you know where to find us."
After Mike and Chris left I got into the shower to clean the sex off. I still don't know what that night says about me. All I know is that I definitely need to start losing more bets.