When Winning a Bet Goes Right

It all started with a basic Facebook comment. One of my wife's former coworkers is a fan of the Philadelphia Eagles. We had met a few times, and I was friends with her and her husband on Facebook. I'm a San Francisco 49ers fan. Our teams met last year in the playoffs, with the Eagles winning. In her celebratory post, I congratulated her on the victory.

During the regular season, both teams were set to face each other during week thirteen, a game both fan bases were looking forward to.

Ashley, my wife's former coworker, made a post during the week about the Eagles last game, and I commented on it to say, "Go 49ers!"

She liked the comment, and I wasn't expecting anything else until I received a message from her a few minutes later saying, "Want to make a bet on the game this weekend?"

I responded back, "I'm short on funds right now, or I would!"

"It doesn't have to be money," Ashley responded back. I asked what she had in mind, and she said, "Let me think about it. I'll get back to you later."

I had forgotten about it by the next day, figuring Ashley had too. But she surprised me when she sent me a message saying, "Still want to bet? I have two ideas for what we could do." I sent back a message asking what her ideas were, and she said, "If the Eagles win, you have to change your profile picture to an Eagles logo and admit that we're the better team, and I'll do the same if the 49ers win."

I told her, "That's easy enough. We can do that."

"Do you want to hear my other idea?" She asked me, and I said sure. It took a few minutes before she responded and said, "Well, if the Eagles win, you put on an Eagles shirt of mine and have to wear it out in public."

I told her, "And I'm guessing the same if the 49ers win? I don't have any 49ers shirts, surprisingly."

"The shirt I had in mind was a crop top. But, I guess if you don't have a shirt, we can't do that," she sent back.

I messaged her to say, "Maybe we can think of something else? I kind of like the idea of having more at stake than just a picture online." She asked if I had any ideas, and I asked, "What would your limits be?"

"I'll do anything but go nude in public," she told me, with a laughing emoji.

"Anything?" I said. She confirmed anything. My mind was in the gutter now, and I thought of lots of ideas. I sent her some of them back after a few minutes in a message saying, "Well, if anything is an option, I got a few ideas. You could wear a hat in public. You said no nudity in public; how about a nude picture just for me? Or could I go buy a shirt? Ignore the nude picture; that's too far for me to ask. How about a 49ers sticker for your car? I like that idea."

Ashley sent back three messages in quick succession, including the first two emojis. The first was a laughing face, and the second was an embarrassed face and a flirty face. The third message read, "You want a nude picture of me? What would your wife think?"

I laughed and said, "If she found out, she would kill me. But I was just joking based on your comment. I'm thinking I'll just go buy a shirt."

"Nah, you said you're short on funds. I'll do the nude picture. We don't have to worry about your wife finding out; the Eagles will win. I have that much faith in them," she messaged back.

I told her she had a deal.

That Sunday, the game was back and forth all afternoon. I was on the edge of my seat for most of it. The 49ers took the lead early before the Eagles stormed back. Down nine with five minutes left, the 49ers marched down the field, with Brock Purdy finding George Kittle in the back of the end zone for a touchdown. Our defense managed to get the Eagles off the field, but not before they ate up a lot of the clock.

With under two minutes left, the 49ers started their drive on the fifteen-yard line with no timeouts. A quick pass to Deebo Samuel, who went out afterward. Kittle dropped a pass next. McCaffrey caught the ball in the open field, getting across the fifty-yard line, and we ran up to spike the ball. A few passes, and we were within field goal range. McCaffrey ran the ball to get it where our kicker, Jake Moody, wanted it, Prudy spiked it, and our field goal unit ran onto the field with three seconds left.

I was standing up as the ball was hiked, our punter held it perfectly, and Moody kicked it through the uprights for the win! I was jumping in my living room, trying to stay quiet as everybody else was asleep in my house!

Sitting down as I watched the team celebrate, my phone went off with a message from Ashley. It read, "What a game! Holy shit! Let me know when I can send that picture!"

I quickly messaged her back to say, "My heart is still pounding! Honestly, don't worry about it! I don't want your husband to find out and get you in trouble. Maybe we'll just revisit it if we meet in the playoffs again."

"No way! A deal is a deal! Just tell me when!" She sent it back.

I shook my head while reading it and said, "Now? My wife is asleep, and I can hurry and delete it after I see it."

I thought about sending another message to make a joke about the Eagles losing when I received the picture. Ashley had blonde hair that ended a few inches below her shoulders. She had on a green Eagles jersey that she had pulled up, along with her white bra, and was flashing her C-cup-sized breasts into her bathroom mirror, where she took the selfie. She was a skinny girl with a flat stomach. She stuck out her tongue through her red lips, and I'm pretty sure she was trying to flip me off as she took the picture.

Before I could say anything to the picture, Ashley said, "Sorry, it's not a full nude. I can take one of those later, or tomorrow."

I told her, "That's OK; you don't have to. I'm really glad I won that bet!"

She laughed and asked, "Are you going to put it to good use before you delete it?" I asked like what, and she said, "Oh, come on. Are you going to jack off to it?"

By the time she sent me that message, I was already in my room, my hand fondling my cock as I looked at her picture. "Maybe," I said back to her.

"If you say yes, I have a few more I can send you that will help," she said.

"Why do you want me to jack off to your pictures?" I asked in return. In a second message, I said, "And yes, I'm doing it now while everybody else is asleep."

She said, "It's a turn-on to know that somebody besides my husband thinks of me that way."

She sent me two more pictures, both of which are obviously a lot older. One was her in her bed, no shirt or bra, and pulling her nipple up to her mouth, with her tongue trying to lick it. In the second picture, she was at work; she worked as a veterinary technician, and she was in the bathroom. She had her green scrubs pulled up, taking another mirror selfie of her chest.

"Let me know when you're done," she said.

Looking at her pictures, I had my six-inch-long, thick cock in my hand, rubbing up and down. Imagining myself fucking her, I quickly came, grabbing a tissue to clean up the mess. I sent her a message saying I was done, and I watched as the pictures disappeared from our message thread as Ashley deleted them.

"Now that you've seen me naked and jacked off to me, tell me about your dick. I don't want a picture of it, so just tell me how big and thick you are," she said.

I laughed and sent back, "I'm six inches long. I've never measured my thickness, but both girls I've slept with have said I'm pretty thick. I can barely wrap my fingers around it. Why?"

"I just was curious! Let's hope we meet in the playoffs!" Ashley said back.

Flash forward a few months to the playoffs. Just as we predicted and hoped, the 49ers and Eagles were meeting in a rematch for the NFC championship, with the winner going on to the Super Bowl. I hadn't heard from Ashley since our last bet, but I decided to send her a message, asking if she wanted to make another bet.

I told her I had bought a shirt that she could wear when the 49ers are playing in the Super Bowl, but Ashley didn't respond, leaving my messages on read. I figured she must have just been feeling guilty about the last bet and didn't want to make another one.

But the next day, she messaged me back to say, "Hey, sorry, I was super busy yesterday and never responded. I actually would like to make another bet. I need revenge! We can bet the shirts if you want, or we can bet oral." I asked what she meant by oral, and she said, "Silly head, oral sex! Eagles win; you make me cum using your mouth. 49ers win; I give you a blowjob. And don't worry about our spouses; I've got that figured out!"

I asked if she was serious, and she said, "Yes, definitely. I'm sure you're worried about cheating on your wife. I get it. When I win the bet, I will come to your house, hide my face under your blanket, and you can pretend I'm here. Same if you guys somehow win."

I asked why she wanted it to be oral, and she said, "Let's just say that ever since you've told me about your dick, I've wanted to see it for myself. And if I don't get to see it, I get an orgasm. Between you and me, my husband isn't very good at giving me them."

I hesitated for a few minutes, thinking of telling Ashley that I wasn't the biggest fan of eating girls out. But I also don't get a lot of blowjobs. My cock was growing in my pants; my brain down there took over, and I told her that she had a deal.

The game that weekend was the complete opposite of the regular-season game. Instead of being a close, back-and-forth game, the 49ers scored three touchdowns in the first quarter and never looked back. Ashley sent me a message at halftime to say congratulations and that we would have to find some time for the blowjob. I tried to tell her that there was still a chance the Eagles could come back, but we both knew it was over.

Ashley told me to let her know whenever I was either home alone or had time to drive over to her house, and she would see if she was alone. The first week went by with no chances. The second week, my wife was off on Thursday and told me that she was going to take the kids to her friend's house to play with her friends kids while they hung out and that she would be gone most of the afternoon. I messaged Ashley to let her know. She surprised me by saying that she could leave work early and come over to my house.

After I got off work and arrived home, I quickly changed out of my dirty work clothes into something a little cleaner, cleaned up my groin a bit, and threw on some deodorant. My cock started to grow in my pants when Ashley messaged me that she was on her way.

I heard the car door shut when Ashley arrived, and I went to open the front door when she knocked a few minutes later. I looked at her as I invited her inside. She had just turned 37 and was eight months older than I was. She had her blonde hair pulled back into a ponytail, black-framed glasses on her face, and just a hint of make-up around her eyes and cheeks. With big hoop earrings in, she was wearing blue scrubs with the name of the animal hospital that she worked at on them.

I followed her up the stairs to my living room, where she turned around, gave me a quick hug, and gave me a kiss on the cheek before saying, "Here or the bedroom?" I told her the living room would work and went to sit down on the couch.

Ashley kneeled in front of me, in between my legs, and eyed my groin. She reached out with her hand, rubbing my cock through the pants I had on, feeling as I started to grow hard. She then unbuttoned my jeans, and I lifted my ass off the couch as she pulled my jeans and my boxers down my legs.

Ashley wrapped her hand around the shaft of my cock, rubbing it up and down as I grew to my six-inch length. Her fingers were being pushed out, the tips of them barely touching, when she said, "Wow, you weren't kidding about how thick you are."

Ashley licked her lips before opening them, her tongue coming out to lick the pre-cum coming out of the tip of my cock. She then sucked me into her mouth and started to bob her head up and down the first few inches of my shaft. Taking me out, but her hand still working the shaft, she licked up and down both sides of me with her tongue before taking me back in and bobbing up and down. She tried to go down a little farther, getting about five inches in before starting to gag with the sides of her mouth being pushed out.

She took me out again and said, "Sorry, I'll work up to deep throating you. Any requests while I blow you? More tongue? Less hand?"

I looked down at her and said, "Keep doing what you're doing, but take off your shirt and bra."

Ashley thought about it for a minute before letting go of my cock, reaching down, and pulling her scrub top up and off her head. She was wearing a white tank top under it with a red bra covering her breasts. The tanktop was off next, followed by the bra. She cupped her C-cup-sized breasts in her hands, squeezing them together as she stared at me, before letting go and going back to blowing me.

With her hand continuing to work my shaft, Ashley kept bobbing her head up and down it. She would lick all around my cock, trying to get me deeper and deeper into her throat. Leaning back on her heels, her hand never leaving my cock, she said, "Excuse my language, but fuck, I've never not been able to deep throat a guy."

I laughed, incredibly turned on by her efforts, and said, "I guess since you can't deep throat me, you'll just have to let me fuck you before I cum down your throat."

"No kidding," Ashley said as she stood up.

She started to pull down her scrub bottoms when I said, "Hey, I was only kidding about fucking you. That wasn't part of the bet."

Ashley was wearing a red thong under her scrubs and turned around to toss her pants on top of the scrub top as she said, "Whatever, I know you want to fuck me." She climbed on top of me, her lap straddling mine on my couch, and said, "Or is that where you draw the line? Because I'm telling you right now, I'm fucking wet, and I want your cock inside me. But, I guess if it's too much, you say so now, and I'll finish blowing you."

I wish I could say I had a dilemma in my head about going from oral to sex, but it was all cheating to me. It didn't matter how far it went. It had been years since I last cheated on my wife. She never found out, and I prayed she never would. I knew it made me a horrible person. But, as Ashley rubbed her groin on my naked cock, wrapped her hands around me, and leaned down to kiss my neck, I gave in.

My hands went down to Ashley's ass, squeezing her cheeks, and I started to kiss her chest. I pushed her away from me enough to get to her nipples, sucking and licking both of them into my mouth.

Ashley reached down between us, pulling her thong to the side with one hand and inserting my cock into her wet pussy with the other hand. She started to roll her hips back and forth, moaning as my cock slid in and out of her. "Fuck, your dick is so thick," she moaned.

I laughed, kissing her nipples one more time, then leaning back on the couch and watching as Ashley started to bounce on my cock. I moved my hands all over her body, grabbing her hips to help steady her, then up to her chest, grabbing her breasts, squeezing them, and pinching her nipples.

Ashley started bouncing harder and faster on me; her mouth opened as she moaned every time she impaled herself on me. I eventually slipped out of her. Ashley felt me slip out and fell onto my chest, breathing deeply. "Fuck, I can't ride you any more," she said.

I pushed her up, standing up off the couch, and adjusted us so that Ashley could lay down on the couch. I quickly pulled my shirt off and tossed it on top of the other clothes. With her legs spread, Ashley pulls my cock back into her pussy, moving her thong to the side again. I leaned down, kissing her lips, as I pushed in deep to her.

Breaking the kiss, I started to thrust my cock in and out of her and said, "I can't wait to cum down your throat."

"Oh fuck, cum wherever you want!" Ashley said as I pounded my thick cock into her over and over. "Just keep fucking me!"

I pushed myself above her, looking down to see her C-cup-sized breasts bouncing as I slammed my cock into her. "Yes! Yes! Yes!" She continued to moan, my thick cock filling her extremely wet pussy.

I was getting closer and closer to my orgasm. I started going harder and faster, slamming my cock into her over and over. I leaned down, licking and sucking her nipples. Ashley moaned out that she was cumming, and I felt her pussy tighten around my cock, clenching hard enough to squeeze my cock, nearly making me cum.

As Ashley orgasmed, she wrapped her legs around me, pulling my body down on top of hers. I could feel her nipples rubbing against my chest as our bodies worked together. "Oh fuck, that felt so good. Do you still want to cum in my mouth? Are you close?" She asked me. I told her I was was, she said, "Then get up here and finish in my mouth!"

She unwrapped her legs from around my body, and I pulled out my cock, leaving her pussy with a pop. I moved up to her open mouth, sliding my cock inside it. Ashley stared up at me with her blue, lust-filled eyes, begging me for my cum. I moved my hips back and forth, sliding my cock in and out of her mouth, her tongue licking all around it.

When I felt my orgasm starting to hit, I wrapped my hand around my shaft, jacking myself off as the first squirt of cum shot out, landing on Ashley's tongue. The second shot landed on her lips. After that, I pushed back into her mouth, going as deep as I could, and pumped the rest of my cum down her throat.

When I was done, I pulled out of her mouth, half standing and half kneeling above Ashley. I looked down at her, seeing her breathing deeply, my cum still on her lips. She was holding up her upper body with her forearms, pushing her chest out and up towards me. Her flat stomach was covered in sweat, which led to her groin and a little peak of hair poking out from her red thong. Her hair was slightly disheveled, and she was staring back up at me, watching as I looked up and down at her body.

"What?" she asked me.

"I just can't believe that just happened," I told her, moving as she started to get up.

Sitting on the couch, she asked, "Are you mad it happened? Feeling guilty?"

I sat down next to her and said, "Nope. There is no guilt here. What about you?"

She got up and went to grab her clothes, saying, "Nah, I never do. I find that it's usually the guys. They either feel immense guilt or they want to cling on."

"Wait, have you done this before?" I asked, watching her put her bra and tank top back on.

After pulling on her scrub top, she said, "Yeah. I was actually thrilled when you mentioned a blow job for a bet. It's normally me that has to start bringing stuff like that up." I asked if her husband knew, and she said, "It was his idea to start. I have an extremely high sexual drive that he can't keep up with. So, before I could start looking elsewhere, he offered to open up our sexual life, and I get to sleep with whoever I want."

"Wow," I said. "Does he sleep with whoever he wants to?"

Ashley pulled her pants back on, sitting down next to me again. She said, "He can, but never does. He does get turned on whenever I sleep around, so I usually go home and tell him about it, unless the person I'm sleeping with is cool with me taking a video. Ours happened so fast, I didn't even have time to ask."

"When you say people you sleep with," I started to say.

"I'm bi. I like guys more, but I'll fuck a lady when I can," she interrupted me.

"Wow," I said again.

Ashley gave me another kiss on my cheek before saying that she had to leave. I kissed and hugged her again at the door, closing it behind her after watching her get in her car.

The next day, Ashley sent me another Facebook message asking if I felt guilt yet. I told her I didn't, and she said, "Cool. So, what's our next bet going to be?"