High Stakes and Hard Lessons

"There is absolutely no chance that your team can pull this off," I said with a drunken sense of bravado as I walked back in the room. "We are up by two and there are five minutes left of the game. You've lost!"

"I've seen crazier comebacks than this," Brad replied. "I wouldn't start talking shit until the final whistle is blown."

"Yeah, okay! I'll bet you another fifty bucks your team doesn't score a single goal and my team wins two to zero."

I couldn't help but talk shit. Usually, Brad and I got along well during soccer matches and rooted for the same teams to win. The exception to this is whenever Orlando, my favorite team, plays Colorado, his favorite team. Those matches tend to be a bit more tense.

"You're already on the hook two hundred bucks if you lose," he replied. "Are you sure you want to up the stakes again?"

"Absolutely!" I exclaimed loudly. "I'll bet anything that you're going to lose," I said with confidence as Orlando gained control of the ball again. "Do you hear me? Anything!" I laughed knowing full well that my team was going to win.

"You'll bet anything?" Brad asked me with a hint of mischief in his eyes.

"Damn straight," I replied. "You name it!"

"It's time someone knocked you off that high horse you're on," he said. "Let's take this to the next level. If you have the balls for it anyway."

"Hell yeah, I do," I replied immediately. "Take it all the way up to the maximum level."

"To the maximum level?" Brad asked. After I nodded my head, he continued. "Okay then. If Orlando wins, I will send you all the naked photos I've taken of Susan."

Susan is Brad's girlfriend. She is a swimsuit model and is one of the hottest girls I have ever seen. I'd kill to see those photos and Brad knows it.

"Deal!" I said immediately.

"You don't even know what I get if I win." Brad said.

"You're not going to win," I replied. "But go ahead, tell me what you want if you some miracle happens and you win."

"If Colorado wins, you have to suck my cock." Brad said with a smile.

"What the fuck dude!" I exclaimed. "That's nasty!"

"You said you would bet anything and that you wanted to take it up to the maximum level," he said in response. "This is the ultimate bet. If I win, you suck my cock and swallow my load. Deal?"

Brad stood there staring at me waiting for my reply. From the look in his eyes, I could tell he wasn't joking. He was being serious.

"You're serious, aren't you?" I asked him. "I didn't know you were gay."

"I am being dead serious," he replied. "I'm also not gay. But you've been talking shit all night and I've had enough. Either shut the hell up or take the bet." He finished.

"You are fucking serious," I replied. "That's sick man. You're sick."

"I didn't realize you were such a chicken shit. You said you'd bet anything. Here's your chance. Take it or be a chicken shit forever. Deal?" Brad held out his hand to seal the deal.

I paused. I was not about to suck his dick, or any dick for that matter, but Orlando was winning two to zip, and this asshole needed put in his place.

"Fine. You got a deal." I said taking his hand and shaking it.

"Deal," Brad said in reply. "Let's see what your future holds." He said turning back to the television.

There was only 3 minutes left of normal time and then whatever stoppage time the referee added on at the end. This was going to be an easy one to win. I was really looking forward to jerking off to Susan's photos.

But that was not what the future held for me. I watched in horror as Colorado rallied and scored not one, not two, but three goals in the last few minutes of the game!

"That is impossible!" I exclaimed after it was all over. "How? Three goals? No fucking way!"

"I told you I have seen crazier things in soccer matches," Brad said. "But you couldn't see past your own ego. This should be fun." He finished with a laugh. "Do you want me to sit in the chair over there or do you just want to get on your knees and suck it right here?"

"No way dude," I said. "Not going to happen. That wasn't even a real bet."

"Not a real bet?" He asked with a stern look. "If Orlando had won, you'd be demanding that I send you the photos of Susan. You know it. I know it. It was a real bet and you're going to pay up."

"Like hell I will," I said.

"Don't force me to make you uphold your side of the deal." He said threateningly.

"And just how are you going to do that?" I asked stepping towards him. I could feel myself getting angrier by the second.

"I'll send Julie the video of you in Panama." He replied.

I stopped in my tracks. I have always known Brad had a video of me getting a blow job from a hooker in a casino bathroom when we were in Panama last year. I never thought he would use it as leverage against me.

"You fucking asshole." I yelled. "You wouldn't dare!"

"I may be an asshole up but you made the bet and I will absolutely send it to her if you don't pay up." Brad continued to stare intently at me. "What you did down there has never sat well with me. You cheated and you brought me into it. Now we're going to clean the slate. You follow through on your bet and I'll delete that video."

"You're a piece of shit!" I yelled back. But Brad didn't move. He was dead serious. I could see it in his eyes. What the fuck! I either had to suck his dick or kiss my entire marriage and family goodbye. What the fuck!

I walked over to the bar and poured a glass of bourbon. I drank it in one gulp.

"Fine," I said after a pause. "I'll do it. But I'll never forgive you for this. And you better delete that video!"

"I will," he said. "Before we get started, why don't you go put some of Julie's lingerie on? That will be really sexy!" he said with a laugh.

"No way," I said. "Just pull out your dick and let's get this over with."

"Not a chance," Brad said with a laugh. "The lingerie will be the best part!"

This was getting out of hand. Thankfully all the bourbon I had been drinking was really helping. I stomped out of the room without saying another word.

I went into my and Julie's bedroom closet and began looking through her drawers. She has some sexy lingerie, but I wouldn't fit into any of it anyway. I found her collection of thigh high stockings, one of my favorite clothing items for her to wear. I pulled out a pair of black opaque stockings. I looked through her collection of skirts and blouses and found a short skirt and blouse that she used to wear when she was a little heavier. I thought I might be able to squeeze into them. I went to the bed, stripped off my clothes, and put the thigh highs, short skirt, and blouse on. I still couldn't believe this was happening.

Once I was dressed in her clothes, I went back to the man cave where Brad was waiting for me. It was humiliating. I half expected Brad to snap a photo but surprisingly he did not. He just sat in the lounge chair, naked from the waist down, with his legs spread apart and his cock laying on the chair between his legs. It was large. Quite large. There was at least 9 inches of half hard dick lying there.

"Don't be shy," he said with a smile. "Get on your knees and satisfy your bet. The better the job, the less time it'll take." He laughed again.

In that moment I was glad I drank the extra glass of bourbon. It made what I did next a little easier. I walked over to his chair, got down on my knees, picked up his cock with my hand, and without any further hesitation, parted my lips and slid them down the shaft of his cock putting it firmly into my mouth. No sense dragging it out. It was either this or end up divorced.

I stopped when I had about three inches of dick in my mouth. I just froze. It wasn't because I realized what just happened or that it was the first time I ever had any kind of sexual contact with another man. My mind was focused on what the physical feeling felt like. The warm, soft flesh against my lips and tongue. It felt different and not at all like what you would think it would feel like. I also thought to myself that this is what Julie felt every time she gave me a blow job.

Brad did not care to provide time for reflection. Now that the hard part was over, actually getting me to put his cock in my mouth, he grabbed a handful of my hair and pushed my head down. Not just a light push but he was going for the gold medal. I was caught completely off guard and was not prepared so I did not react until my gag reflex kicked in. By that time the entire length of his cock was in my mouth and throat.

I gagged. My body convulsed. He relaxed the pressure and let my lips slide up nearly all the way. He kept enough pressure on the back of my head to ensure his dick didn't completely leave my mouth. It was nice of him to let me finish gagging and breathe a little.

"Stop stalling and hurry up," he commanded. "I don't have all night."

He started pushing and pulling my head up and down from his grip on my hair. My mouth traveled the length of his cock, from tip to base, over and over. My gag reflex reacted less and less each time his cock traveled down into my throat.

It must have been one hell of a sight. Me, wearing a short skirt and thigh high stockings, down on my knees, with my head bobbing up and down on his cock. Not something I thought I'd ever be a part of. Fuck you Orlando for losing that match!

"You better try some other tricks or you're going to be there for a while," Brad said. "You don't stop until you've swallowed my entire load."

I wanted to get this over with as quickly as possible. I started thinking of all the things that Julie does when going down on me. I moved my tongue forward to put more pressure on the sensitive parts of his dick. Then I wrapped my hand around his cock and started stroking and twisting as I continue to move my mouth up and down his cock. It was awkward at first but then I found a good rhythm. I kept working his dick and sucking on it hoping that he would finish so we could be done with this.

After a short time, I realized that I didn't feel any pressure on the back of my head. Brad had removed his hand. He wasn't forcing me to suck his dick. I was doing it all on my own. I was sucking his cock. On my own. This was a very strange thought.

I didn't have much time to continue that train of thought. Brad's hand whipped down to the back of my head again and held me down on his cock. He started thrusting his hips up and down, fucking my face with everything he had. I could feel his cock starting to bulge. I knew what was about to happen.

"Yes," he groaned. "Fuck yes. Swallow this bitch!"

I felt his cock throb starting at the base and pushing up the length followed by a very warm and very wet glob of cum shooting into my throat. I didn't have any choice but to swallow it. It was instinct. And then his cock throbbed and exploded again. More cum filled my mouth and I swallowed it too. This repeated more times that I can count. I had no idea a man could cum that much to be honest.

His cock stopped throbbing but he didn't release my head.

"That felt amazing," Brad said. "But you're not done yet. Clean my cock for me, bitch. Get all the cum and spit off for me."

I tried to say no but it came out as a muffled mess of sound around his still hard cock in my mouth. I tried to push back to stand up but he held me firmly down on his cock.

"I said you're not done yet," Brad said tersely. "Clean my cock or Julie gets the video."

There was nothing that I could do but comply. I continued to suck and lick his cock and I didn't stop until he told me that I could.

"I hate to say this buddy, but that was one of the best blow jobs I've ever had." Brad said. "You're a natural!"

"Fuck you, Brad!" I said. It is tough to sound tough when you're wearing a short skirt and thigh highs, on your knees, with your mouth full of the taste of cum. "I followed through on the bet. Now delete the video."

Brad taped a few keys on his phone.

"Done," he said. "The video of you in Panama is deleted."

"Thank you," I replied. "Now get out of my house you asshole!"