Chapter 2: Learning to Cover Your Bets

Sharon gets a lesson in what happens when she makes wagers she can’t cover. She finds a way, but it costs her something precious.

I marked this story finished, but I think there will be more chapters later. I just didn’t want it to get flagged as incomplete. Enjoy!

After that first time with Brian, I sucked a lot of cocks. I really enjoyed the feeling of power I got sucking a guy off, and I loved feeling them flex and pulse as they came down my throat. My dating life quickly resumed. The guys didn’t even care that I wouldn’t let them fuck me, as long as I sucked them off. And none of them every complained about coming in my mouth. :)

The summer I graduated, I had just turned 19 and was at a party Brian’s fraternity was hosting. There was a guy there named Brad. He was sort of standoffish, a little bit of the bad boy type. I found him exciting. “He likes you,” Brian said from beside me as I poured myself a drink. “But be careful with him. He’s strong willed. Don’t get yourself in a compromising position.”

“Would he...?”

“No. He won’t force you, if that’s what you’re asking. If you tell him to stop he will. But if you don’t he might not, so if you get to that point just be clear with what you will allow.”

“Ok. I’m pretty good at handling that.” I replied. “But I do need your help with something.”

“Name it,” Brian replied.

“I made some stupid bets, and I owe some money to a couple people from school. Well, one guy in particular. And now he wants me to pay up this weekend. One way or the other. I don’t have the money, and I certainly don’t want to fuck him, but I’m running out of time.”

“Shit, I spent everything I had on my car yesterday,” Brian said. “How much do you need?”

“500,” I replied.

“Damn! You need to stay small time, Cher. Brad’s the only one of us who would have that on short notice. Be sweet to him this evening, then ask him nicely and he’ll let you borrow it, I’m sure.”

I smiled. “I’m pretty good at persuading guys to do what I want.”

“Just remember, be careful.”

“Always!” I laughed as I skipped away in search of Brad. After I found him, we danced and drank most of the evening. I was careful to regulate our drinks, so we were relaxed but not drunk.

As a particularly slow song ended, I looked up at Brad and smiled shyly. “Let’s go somewhere quieter.” He nodded and we went to the back of the house, where there was a separate sitting room. It was empty, and Brad closed the door behind us. I melted into his arms and he kissed me softly. I lingered in the kiss awhile, enjoying the feel of his body next to mine.

I broke the kiss and approached the subject of my debt, telling him the story briefly, including my offer of several blowjob’s, which was turned down, before asking if he would loan me the money. “I don’t want him to be my first fuck, so I have to find a way to pay him. Can you help me?”

“Well, I don’t make loans,” Brad said. My face fell. “But since you’re a betting girl, I’ll make a wager with you.”

My stomach fluttered. “What kind of wager?” I asked softly.

“Well, I’m intrigued by your oral talents. And since I’m a guy, I love a good blowjob.” I was starting to like the direction this was going.

“Ok. I’m game. What’s the bet?”

“You agree to suck my cock, and if you can make me come in three minutes, I’ll loan you the money.”

Three minutes! That was forever to me. If I just wanted a guy to squirt, I could be swallowing 30 seconds after my lips touched his dick. This was going to be easy!

“And what if you can hold out for more than three minutes?” I said, though I really doubted that would happen.

“We’ll deal with that if we get there,” Brad said. “So what do you say? You in?”

I slid a hand between us and groped his cock. I could tell it was a nice size, even thru his pants. “Sure! I’m going to like having this in my mouth,” I smiled as I stroked him and felt him growing hard.

“Just one condition,” he said. I cocked my head to one side and raised my eyebrows. “I get to see you naked.” Brad smiled.

“No touching without permission. Just because I get naked doesn’t mean anything is going to happen.” I replied.

“Deal.” Brad said. “Take it off slow for me.”

I backed up a couple of steps and started a slow striptease. I took my time undressing, but soon stood naked before him. I reached and unbuttoned his pants then, freeing his cock from its restraint. It was a nice size, as I had surmised. Brad pulled his shirt off and dropped it on the floor as I leaned forward. He pulled his phone out of his pocket. “You ready? I’ll start the timer when you start.”

I nodded. “I’m ready.” I leaned forward and he hit the start button as I sucked his cockhead into my mouth. I figured I would play with him a bit before I made him squirt. I licked softly around the head of his cock before sliding slowly down the shaft, stopping when I felt him touch the back of my throat. I didn’t want to give away all my talents up front. I stroked slowly at first, keeping an eye on the timer on his phone. A minute had passed already. Time to get down to business. I really wanted to take my time and pleasure him properly, but I figured I’d get another chance to do that. I sucked him in completely then, pushing his cock deeply into my throat and working him with my tongue while caressing his balls with the other hand. It wouldn’t be long now. It never was, when I started deep throating them in earnest. He wasn’t moving as fast as I wanted, and the second minute was ending. I let some spit drop onto my hand at the base of his cock, then slid the hand upward and caressed his ass. That almost never failed to make guys come in my mouth, but still he didn’t squirt. I slipped my finger into his ass then, waiting eagerly on the reward I knew that would bring. Instead of his warm juice in my mouth, I heard the beeping of the phone as my 3 minutes expired. How had he held out that long? No guy had ever been able to last 3 minutes when I really wanted him to come.

I felt Brad’s hands under my arms, and released him as I stood up. He kissed me passionately. “Nice effort,” he smiled. “I thought you were going to get me with that ass play.”

“Me, too,” I replied. “What now?”

‘Well, I think sucking my dick got you more excited than it did me. If it didn’t, and you’re not soaking wet, I’ll GIVE you the money and we’ll get dressed and go back to the party.”

“And if you’re right?” I asked softly.

“A bet’s gotta have two sides. If I’m right, and you’re soaking wet, I get to fuck you. Right now. I’ll still give you the money, though. Deal?”

I couldn’t really say no, since I owed him from the original wager. I already knew the answer, but I hoped he would give me a break. I swallowed hard and just nodded, unable to say it out loud.