The Bet

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“Hold on, I need to stop here quick,” Katie said as she whipped the car into the dimly lit parking lot and pulled up to a small storefront. The pink glow of the neon sign lit up the darkness casting a glow across the puddles from the afternoon of heavy rain. As we got out of the car the wetness still hung in the air and the humidity clung to your skin making me regret even getting out of the car.

Katie was one of my best friends, we had been camp counselors together a few summers ago after hitting it off we had been pretty close ever since. We had never actually dated which I wish wasn’t true. She was a drop-dead gorgeous girl by any guy’s standards. Taller than most at six feet and had long blond hair down to her waist that she liked to braid any chance she could. She played tennis and was very fit as well as muscular going to the gym almost every day. She could bench more than most guys I knew. With large D breasts, she could get any guy she wanted and she knew it. Often wearing low-cut tops or tight athletic wear while working out, she loved it when men tried to catch a glance and even more so when she caught them.

We had always had feelings for each other or at least I had for her and I thought she did for me but the timing was never right. In my opinion, she always dated jerks or guys who never treated her right yet she kept going back to them almost as if she was chasing after something and could never find the right guy to give it to her. I tried to stay out of her love life, maybe that’s why we had stayed friends for so long.

As I followed her in the store I saw what we were here for. I had been so out of it from our concert and my ears were still ringing a bit that I had failed to notice we had walked into a sex store. The walls were littered with everything from lube and massagers to lingerie and penis-shaped bachelorette party gifts.

I gave a slight smile to the girl working the counter and slinked to the back where Katie was already making her selection. She looked at me and held up a clear tube of pink gel. “I needed some more lube, ran out last week and I’m all wired tonight from that show. I need a little pick-me-up before I go to bed.”

“Wow pink, nice, matches your dildo.” Me and Katie had always been very open about our sex lives and who we had slept with or what we did in the bedroom or at least she was with me. My sex life wasn’t so busy at the moment. I was one of the few people she was completely open to which often was excruciating when she would detail events like how she had ridden the buff gym guy with the monster cock the night before. It often just made me wonder what it would be like if that were me.

As we made our way to the front she stopped and grabbed a package off the wall, “Look this one matches mine it’s the same color pink only bigger.” I smiled and nodded. Katie smiled back even bigger and looked me dead in the eyes. ” Wanna make a bet? I bet I can sneak this out of here.”

“Katie, that’s shoplifting. If you get caught you could be in big trouble.”

“Oh boo hoo, Mr perfect I’ll tell you what If I can smuggle this out of here without the girl at the desk knowing when we get back to my place tonight I’ll use it and you can watch!”

I was a bit taken aback, Katie was a strong woman and always took the dominant role in her relationships and even most things in life. I had even seen her naked once or twice or helped her pick out stuff like lingerie but this was still a bit shocking. I gulped and tripping over my words at her sudden proposal and was able to make out a slight yes.

“Oh good” she stated as she grabbed my arm, spinning me around and lifting my sweatshirt. Pulling my waistband and before I could resist she shoved the package in my pants and pulling my sweatshirt back down covered it up. We made our way up the front and checked out the entire time I was just waiting for the cashier to notice. As we made our way out and to the car I was sweating bullets half expecting the alarm to go off and the girl inside to come running after me.

Getting in the car I reached to pull the package from my pants and Katie swatted my hand away. “Not until we get back to my apartment.” With that, I nodded, putting my hands back down to my sides and she started the car.

The ride back to her place was short, the tires splashing through the small puddles and the whole car ride sitting in anticipation of what was to come. Shortly later we pulled in, Katie lived in a duplex with two rooms and one bath connected to a small living room with a kitchen. It wasn’t huge but for the area, it was a great place in fact I was the one who had found it for her.

As we made our way inside she told me to sit on the couch and keep her toy in my pants while she got ready in the other room. I had to admit I was very excited at the prospect of seeing her fuck herself with a dildo. I had only gotten a short glimpse of it in the store but it had to be at least 8 inches long. If we couldn’t date and I couldn’t fuck her this was at least the next best thing and I didn’t really care what happened to our friendship as long as I got to see her shove that monster in her pussy and my cock agreed.

It took a few minutes but Katie soon emerged. She was wearing a black lace bra with matching panties connected by straps running down her torso connecting the two pieces making a stunning figure-fitting single lingerie piece showing off her gorgeous body.

She smiled as she noticed me clearly staring but despite that, I couldn’t look away. “Pull it out of your pants.” I quickly obliged, pulling the package out of my pants and handing it to her eagerly.

She smiled “Now while I get ready you go into the bedroom and strip.” I was a bit confused. I thought she had already gotten ready? She noticed I was perplexed, “If I’m going to be just about naked you might as well and that means if you want anything to happen tonight you’ll do as I say now get in there.” She didn’t have to say it again. Her harsh tone quickly made me get up from the couch and scurry into the bedroom. Stripping off my clothes and throwing them in a pile, I stood there curious as to what to do next. “You see those handcuffs on the bed? Get on facing the headboard and handcuff yourself to the bedframe. I don’t want you running away on me or worse getting in my way.”

I was beyond confused now but since I had given her the dildo her tone had changed and she was now ordering more than asking. Besides I was naked in her apartment while she was dressed like a goddess, my horny cock wasn’t backing out now and I would do just about anything to stay in this position.

Grabbing the handcuffs I ratcheted it down on my wrist and looping it through the headboard closed the other side tightly until the cold steel held me in place facing the wall with my back to the door. Seconds later I heard the door open and turned my head to see Katie standing in the doorway. The large pink dildo perched on her crotch and her hand held the shaft firmly accompanied by a giant grin. “It seems someone didn’t look at what they were shoving in their pants before they made that bet.

You see that dildo came with a harness, ever heard of a strap-on?” I swallowed hard, my eyes fixed on her crotch. “You see when I said I was going to use it tonight and you would get to be there I meant I was going to use it on you. I have been looking for someone to peg and deep down I have been wanting it to be you for a long time. Now I have you naked and handcuffed on my bed and all you need to do is bend over and show me that ass of yours and I’ll give you the best orgasm you have ever had.”

I had played with my ass some before but only with fingering it or a few butt plugs, never a dildo, and never one that big. Still despite this revelation even if I didn’t like it I just had to tough it out once and then It would be over. In fact, Katie looked even hotter with a big rubber monster between her legs. I nodded and a bit nervously gave a smile, “I guess I got the sore end of the bet then so it’s only fair.”

“That’s the spirit” And with that she jumped up on the bed and got on her knees grabbed the bottle of pink lube she had purchased earlier, flicking the cap open I heard it squirt onto presumably her strap right before she squirted another large helping on my ass. The cold sensation made me jump as she laughed and started smearing it around and slowly working it into my ass sliding her finger in and out. “We are going to need a lot of this your hole is night and tight just the way I imagined.” She responded giggling as I felt her insert a second finger and speed up her motion a bit.

I let out my breath. I was holding trying to relax as she slowly stretched my hole. After not too long I felt her move behind me and that’s when I gasped as it slid in. She grabbed my ass holding it still and slowly started sliding her strap in and out. I had to admit it felt good as I relaxed and let her pump in a steady rhythm.

She slowly began to speed up and with every thrust, I was getting more and more pleasure. Soon I was overcome by the feel and entered a wave of total bliss. Arching my back and pulling on my cuffs Katie had sped up to fucking speed and was pushing with every thrust and fucking my ass hard. I let out a moan as she rammed the pink invader deeper and deeper in me, laughing as she placed both of her hands on my ass cheeks and slowed down a bit but adding pressure to the end of every thrust ramming it on my prostate over and over. “Looks like someone is liking it. Who knew you were a little ass slut.”

I didn’t even care what she thought of me, I didn’t even know what I thought of myself in the moment all I knew was It felt so fucking good. “Please Katie fuck me faster I think I’m going to cum.” The words escaped my mouth without a second thought but the hand on my throat made me figure she liked it. “Wow all it takes is some fucking in the ass and you’re already gonna blow your load. Well, we might as well make your first orgasm from your ass count. Squeezing my left ass cheek and tightening her other hand around my throat even more, pulling my head up with my hands still outstretched in my cuffs, she sped back up to full speed.

At this point, I had lost all control of my body. I was in her grasp with nowhere to go and on the edge of the biggest orgasm of my life. The entire bed was shaking and my eyes rolled back in my head while I was being basically choked by her which I didn’t know until then turned me on a great deal. I started what can only be described as screaming mixed with a moan as she gave a last few powerful thrusts and my orgasm overcame me. My back arched and I strained against the handcuffs as I came all over the sheets with her dildo still in my ass.

Just like that it was over, she released her grip on my throat as I gasped for air and tried to recover from what had just happened. I felt her slide out of me as she leaned forward laying overtop of my back, the lube-covered dildo laying on my back. She leaned down kissing me on the cheek. “I’ll let you recover and then we will go for round two. It looks like I am going to have a lot of fun with you!

Who knew turns out losing that bet was worth it.