A Bet I Might Regret

"It's only 5 minutes", I thought, "how hard could it be?"

Me and Liya had been together for about 9 months now. It had moved quite quickly and we'd recently moved in together. She was always totally my type and I was still so attracted to her. She had mid length brown hair just past her shoulders, and beautiful brown eyes that still after 9 months made me stumble over my words when she looked up at me with them.

Her body was incredible as well. I've always been more of a boob guy, but her ass had made me a convert. Just the right size, and it bounced slightly as she walked. Since we moved in together I'd noticed she loved to show it off by walking around in just her underwear. Sometimes I got the impression she did this while I was trying to work because she got off on the idea of distracting me and teasing me like that. Not that I was complaining, of course.

Her tits were just perfect as well. She wore a 32C and they were perfectly perky and even. She also had one of her nipples pierced which I've always found so hot. I loved to play with it during foreplay, teasing it with my tongue and mouth. It helped that her nipples were super sensitive as well -- I loved to drive her absolutely desperate by just teasing her nipples and make her beg me to finally pay her pussy some attention. I always gladly obliged, of course.

In the bedroom I wouldn't say we were super adventurous. We had sex quite regularly -- about 4 times a week -- but aside from the occasional bit of teasing, or using some handcuffs or a blindfold, it was generally pretty vanilla. But it was good. I found her so hot, and I think she felt the same way about me. So we always had fun playing with each other, and it had never felt stale.

But one night just as we were getting set to go to bed, she looked directly at me with those beautiful brown eyes, and said "do you want to make a bet tonight? I've got an idea which I think could be fun"

"A bet?" I replied, intrigued.

"So you can say no if you don't want to, but... I want to set a little challenge. I want to see if I can make you cum in... 5 minutes, using just my mouth. If you manage to last that long, you can ask me to do whatever you want with you. If I win, then I get to do whatever I want with you".

I wasn't expecting that. But honestly I loved the idea. I mean, I get a blowjob, and then either I get to fuck her however I want, or she gets to do whatever she wants to me. I didn't know exactly what she'd do, but I assumed something like making me eat her out, or maybe she'd get me to fuck her in her favourite position. Both of those sounded pretty fun to me. It seemed like a win-win.

"Oh wow, that does sound fun" I tried not to sound too eager.

"Of course, the timer would start when you were already hard. And I'd have to tie you up first as well, just to make sure you don't try and cheat or anything".

We'd played with handcuffs a few times, but never tied each other up. But I liked the idea, and it was only for 5 minutes, so I was definitely up for giving it a try.

"You mean you don't trust me?" I said with a smirk

"Of course I do! But when the stakes are this high, who knows what you'll try and do? I just want to make sure it's a fair game!"

"Are these high stakes? What do you have planned if you win?" I was starting to think she had been thinking about this for a while and had more of a plan for if she won than just asking me to eat her out.

"Well that'll have to stay a secret for now, I'm afraid. Besides, it's only 5 minutes. You'll probably win anyway!"

She was right. It was only five minutes. I didn't have pornstar stamina or anything like that, but I wasn't a minuteman either. I could usually last for at least 15 minutes in bed, and I'd jerked myself off earlier in the morning as well, so 5 minutes should be no problem.

"Alright, deal!" I said.

"Ok! Well let's go get you all tied up!" She said, while looking me direct in the eye with a devious smile on her face. My cock started to swell already. This was exciting me more than I expected. Maybe this wouldn't be so easy after all.

She led me into the bedroom and told me to undress while she got the ties sorted for the bed. I slowly unbuttoned my shirt, and then unzipped my jeans, taking them off along with my boxers.

"Someone's excited about the game" She said as she looked round and saw my cock spring out of my pants, rock hard already.

"Fuck. I guess I am. Still, it's only 5 minutes. Should be an easy win for me!"

She didn't reply, and just confidently smirked while turning back round to finish off preparing the bed.

"Alright, hop up, it's time to get you all tied up."

I jumped onto the bed and Liya then started tying me to the corners of it. She started with my wrists, tying both of them up, and then went to my ankles and tied them to the bottom corners of the bed. I'd never been tied up like this before, but judging by the reaction of my cock, I think I liked it.

"Mm, good. All tied up. And you're rock hard already. So I think we're ready to start!" She said, looking down at my helpless body while standing at the foot of the bed.

She got her phone out and opened the clock app, setting the timer for 5 minutes. She leant over and laid the phone down next to me, so I could turn my head and see how long was left if I wanted to. As she did that, her arm rubbed against my cock a little, making me twitch. I don't know if this was an accident or she did it on purpose, but I let her get away with it anyway. Just before she clicked start on the timer, she jumped up and, in a pretend-innocent voice, as if she hadn't planned this whole thing down to the minute detail, said:

"Oh, silly me. One more thing to do before we start"

With that, she immediately stripped naked in front of me. Lifting her dress over her head, and then taking off her bra from behind and sliding her panties down her legs.

"Fuck", I couldn't help saying it. Even after 9 months together I still found her body incredibly sexy every time I saw it. My cock twitched again and a little bead of precum leaked out. "It's only 5 minutes", I thought... But fuck these were going to be a long 5 minutes.

"OK! Time starts now!" She leant down and clicked start on the timer. I could hear it ticking away next to my head.

I thought she was going to go straight in and start sucking me as fast as she could. But instead she just started kissing my neck, and then slowly working down my chest with her lips and tongue. At first I thought she was wasting her time, but after a few seconds I realised my cock with twitching and leaking like crazy.

She kept working down slowly, over my stomach and down onto my thighs. My cock was just stood there, untouched, increasingly desperate. I looked over at the timer -- only 45 seconds had gone.

"Awh, poor boy. Is time moving a bit slowly at the moment? And I haven't even started sucking you properly yet."

She looked up at my with those eyes that drove me crazy, and then opened her lips and placed them right above my cock. They were just millimetres away from touching my tip. So close, but so far. She then stuck her tongue out and worked it down the length of my shaft, still not quite touching it as she slowly moved it up and down, staring at me the whole time.

90 seconds gone. This was such a strange feeling. I wanted to feel her lips on my cock so badly. I was desperate. I needed it. But I also wanted to win the bet. And I knew that if she started sucking now I'd blow almost instantly I was so worked up.

"Do you want me to suck you yet?" She asked and then gently kissed the tip of my cock. My whole body twitched and I let out a primal moan I couldn't keep in.

"Poor boy, you don't stand a chance, do you?"

3 minutes to go.

Her lips wrapped around my cock and slowly worked down it. Feeling her warm, wet mouth on my cock felt so incredible. As she worked up and down my shaft with her lips, her tongue was teasing the tip of my cock, focussing on that spot on the underside of my tip. It was driving me absolutely wild and I could feel myself getting close to the edge, but I was trying my best to hold out.

She kept sucking and licking and teasing me like that, getting faster and faster. Every now and then she'd take me as deep as she could. She was able to get most of my cock down her throat, but she'd gag just a little right at the end. This meant my cock was getting covered in her spit, and the blowjob was getting faster and sloppier and messier with every passing second.

2 minutes to go.

"Are you worried about what I'm going to do to you when I win?" she took a brief break from sucking me to ask.

"When?" I managed to reply. I tried to sound confident and cocky, but between the moans and whimpers it probably didn't come out quite as confident as I wished.

She just moaned into my cock and sped up again. I was getting closer and closer. My cock was about ready to burst. I didn't think I could hold on much longer. I looked over to the timer. One minute to go.

"I want your cum, baby. Give it to me. Let me swallow your load. Let me taste you. Be a good boy for me."

Fuck. I'd never been called a good boy before. I didn't know I was into that. But as soon as she said it, my cock got right to the edge and to the point where I couldn't stop it anymore. I was going to cum. Fuck it, I thought. I can't hold off any longer. I might as well let go and enjoy this orgasm, at least.

She took me deep once more and that was enough for me. My whole body tensed up and I started shooting my load into her mouth. I couldn't believe it had only been 5 minutes. I felt like I'd been teased for hours. I couldn't remember the last time I shot a load this big, it just never stopped. I looked down at Liya and she was swallowing every drop of it. Seeing that just turned me on even more and I keep shooting more cum into her mouth.

Eventually my orgasm stopped and I came back to reality. Just as I did I heard the timer go off. There must've been only 30 seconds left or so when I came, but I couldn't hold out.

"Oo, looks like I win!" Liya said while looking up at me with a beaming grin on her face

"Fuck. That was amazing." I replied, trying to catch my breath after the orgasm of my life.

"Mm, well I glad you enjoyed it! And now... time for my prize"

In the height of that orgasm I'd forgotten about the bet. Now I'd come back to reality I was increasingly worried about what she had planned. I was also acutely aware I was still tied up and helpless.

"Mm, well I'm all yours Liya! Untie me and I'll do whatever you want"

"Untie you? Oh no... you're staying tied up for a while yet"

Fuck. What had she got planned?

"Do you trust me?" She asked.

I did, of course. But I felt like I was seeing another side of her come out right now. I couldn't decide if I was scared or excited.

"...yes. I trust you." I said, tentatively.

"Look, you've probably guessed I have a plan worked out for this. I hope that you're happy to go along with it because I think it will be a lot of fun. But if you're not into it, just tell me, OK? I'll give you a safe word -- pineapple. Say that and I'll stop all this and just get you to eat me out as my prize. But I hope you'll at least give this a try."

A safeword? What did she have planned? This was definitely new for our sex life.

"Fuck Liya, what do you have planned?"

"I think it's best if I just show you..."

She walked round and pulled a bag out of her bedside table. She opened it up and pulled something out. I was still tied to the bed, and tried to look round and see it but I couldn't quite see what it was. I heard some metal clinking. And was that a key I saw?

She walked back round to the foot of the bed and then crawled up between my legs.

"Fuck, what is that?" I asked, looking at some metal device she was holding next to my cock.

"This is my prize", she replied.

"Fuck Liya, is that a chastity cage?"

I had done a bit of edge play before, and I liked teasing, but I'd never done any denial play, let alone chastity.

"That's right! Again, if this is all too much, just say and we can call it off. But once I put this cage on, then your cock is mine, understood? I'm going to hold your key and you won't be able to cum, you won't be able to touch yourself, you won't be able to even get hard, unless I say so, OK?"

Liya seemed so excited about this. And I had to admit to myself the thought of giving her full control of my cock did excite me as well.

"OK. I'm in. Just don't treat me too mean, will you?"

"Oh don't worry, I won't torture you". She said in a sly tone. "Too much."

With that she reached down to my cock and slid it into the metal cage. She closed the lock shut and then put the key on a small chain around her neck. I started to think about what I'd got myself into. My cock, totally in her control. When was she going to let me out? How long would it be until I even got to feel any contact on my cock again? A day? Two? Surely not longer than that. Even on the days when we didn't have sex, I usually jerked off anyway. I wasn't used to going without pleasure for more than a day or two.

As I kept thinking about all the things she might do to me over the next few days, I noticed the cage around my cock get tighter and tighter. Fuck, I was enjoying this.