Betting to Bedding

For the next few weeks, we went back to our original style bets with a bit of flashing and had some great sex when we got home. That Friday, we decided that would be a good time for a bet or two. Seeing as I knew what the Bonnie's third 'wish' was, we'd decided that she could change it to a new one as long as I could change my third one if I wanted. I was really hoping I'd win because I'd only gotten one and she'd already gotten two.

We both enjoyed playing video games so we decided that it would be best two out of three for the latest shooter game I'd picked up. I'm pretty sure Annie knew what we were going to be doing because she said, "I think I'll go listen to some music."

I won the first one, she won the second and the third was close - she tried everything she could to throw my game but I managed to beat her by just over 100 points. She tried to look disappointed but I could tell she was looking forward to seeing what I'd written down.

When she pulled it out, I knew which one she'd picked just by the look on her face and she confirmed it by saying, "Fisting? Not a chance! I like a nice big cock but no way a hand's going there!"

"That's ok, once Annie's spanked you then you can see what the other one is and decide."

The reminder about the spanking made her think and she tried to 'downgrade' it to me fucking her ass again, I said I'd stay with the original plan.

She didn't say anything, just got up and headed to Annie's room. Annie must have heard some of what we'd been saying because when she opened the door, her nipples were already hard.

"So, who's getting spanked tonight?"

Bonnie mumbled a soft "Me."

Annie looked at Bonnie and said, "Mmm, I kinda hoped I'd get the chance, you've got a nice ass! Clothes off and over my knee for your spanking."

Bonnie did just that and while I couldn't explain it, I found the same that Bonnie had - it was much more of a turn on watching Annie spank her than when I'd spanked her myself and I couldn't resist taking my cock out and stroking it. Annie got spanked just as hard as I had and was squirming by the time she'd gotten 10 and muttering, "ow, ow, ow" by the time she was at 20. As soon as the 30th one landed she reached back to rub her ass and said, "Damn, that hurt!"

When she got up, I tried to see if her pussy looked wet or not but instead, I noticed a wet spot on Annie's crotch just like Bonnie had mentioned after my spanking. After a bit of rubbing, Bonnie said, "Ok, now let's go and see what my other option is."

"Actually, why don't you stay here and I'll grab the glass for you?"

From the look on her face, Bonnie wasn't sure what was happening but before she could say anything, I grabbed the jar and came back. I could tell Annie was curious too and even more when Bonnie looked at what I'd written, looked at Annie, looked at me and said, "Well, it looks like more fun than the first option."

Annie couldn't hold back any more and asked, "What exactly was the first option?"

When Bonnie stammered out, "getting fisted", I was quite surprised when Annie said, "I've seen a few fisting videos, never tried it but looks like it could be fun! What's this option?"

Bonnie tried handing me the paper to read it out but I just shook my head and said, "You tell her."

"Well, it says 'get both pussy and ass fucked at the same time' "

Annie just laughed and said, "Guess I get to listen again while the two of you enjoy what you're doing!"

I just grinned and said, "Not necessarily!" then turning to Bonnie I added, "Remember the bet where you had me eat you after sex and you said that the way you'd really like it was with me tied and I agreed? Well, here's what I'd like....Annie's right here so..." and I held out the strap-on that I'd grabbed from the bedroom.

Bonnie's reaction was a series of stutters, mumbles and looks that told me just how surprised she was. Annie was trying to stay calm but her voice cracked a little when she asked, "Which one of us goes where?"

I thought about it for a couple of seconds then looked at Bonnie and said, "You'll be on the receiving end, why don't you decide?"

Bonnie looked back and forth from Annie to me a few times before looking at Annie and saying, "I've felt him in both and never had another woman in either. How about you start in my pussy and then switch so Dave's in my pussy and you can try my bum?"

After a quick, "Hell ya!", she pulled her t-shirt off and surprised both of us by being naked underneath. Her tits were a bit larger than Bonnies but the nipples were smaller and really hard. As I looked down, I could see her pussy was shaved but unlike Bonnie's small, tight lips, Annie's were much bigger, open and what caught me the most was that her clit was already protruding from between them where Bonnie's clit wasn't easy to find even when she was aroused.

If I'd been asked, I couldn't have decided which one was sexier but the sight of the two of them naked could have gotten a dead man hard. I had originally been tempted to write down 'watch two women have sex' but at the time figured there was no chance it was going to happen but here it was, and I had a front row seat.

Bonnie lay back on the bed but instead of fucking her right away, Annie reached down and tentatively felt her tits and then down between her legs where she touched and then fingered Bonnie. I was kind of hoping she'd go down on her but I didn't want to push things. As it was, Annie fingered her until she came and then moved over her, lined up the strap-on and slid it into her pussy.

Guys, if you EVER have the chance to watch one girl fuck another, take it! I really can't explain how much of a turn on it was to watch them. Annie started slow but as she got the feel for it, she sped up and thrust harder. I could see from Bonnie's face that she was getting close to cumming so I reached over so I could squeeze and tease her nipples for a few seconds before leaning over to suck on them. That did it and almost right away she was moaning and shaking as she came. When she'd relaxed, I lay beside her and said, "Climb on whenever you're ready!"

It took her a few minutes but eventually rolled over and with a smile and lowered herself onto my cock. As much as I was watching Bonnie slide up and down my cock, I was also watching Annie, watching us. Her fingers were between the harness and her pussy, obviously touching herself as she moaned softly. After a minute or so of watching, she grabbed the lube that I'd brought with the strap-on and I could actually feel Bonnie's pussy clench the first time Annie slid the tip of a slippery finger into her bum plus I could even feel the finger against my cock through the membrane. I had no idea if Annie had ever used a strap-on before or had received anal but she seemed to know to take her time and use lots of lube because everything she did seemed to excite Bonnie more. When she shifted so she was right behind Bonnie and pushed the tip of the strap-on against her opening, I felt Bonnie push back gently. It only took a little bit of pushing before I could feel the strap-on easing into Bonnie's ass and from her moans of "Oh fuck, I've never felt this full!" I was pretty sure that Bonnie was enjoying herself too.

Unlike in porn videos, it took Annie and I a little bit to find a rhythm where one of us wasn't falling out but when we did, Bonnie's moaning increased and so did mine. The combination of having her pussy and ass filled at the same time seemed to trigger orgasm after orgasm from Bonnie. None of them were big but they came one right after the other. The additional pressure of the strap-on against my cock soon brought me to orgasm and I filled her pussy with spurt after spurt of cum.

It certainly wasn't 'elegant' but Annie pulled back, took off the strap-on and flopped onto the bed to my left, then Bonnie rolled over and flopped to the other side of me. After a few minutes of just lying there, Bonnie said, "Wow! That was something right out of a porn flick and damn it felt good!"

Looking at Annie she added, "Have you ever done anything like that before?"

Almost shyly, she replied, "No, but I watch a fair bit of porn and enjoy the kinkier ones so I've watched lots of stuff but I've never had the nerve to try anything because I always thought that wouldn't happen in real life and if I did, whoever I was with would think I was either weird or a pervert."

Bonnie and I chuckled a bit at that before I said, "Well, I certainly never thought you were into much of anything but I'm glad you are because damn that was exciting!"

Annie just smiled and said, "It sure was and damn I'm horny too...too bad guys can't keep cumming the way women can, I could use a good filling right now.

I looked over at Bonnie and then at the strapon but she said, "I'm 'fucked out' for the next while."

Looking back at Annie, I said "Well, if you'd like to try something, I'm pretty sure I can help you cum."

"Maybe, what are you thinking?"

As I grabbed the lube, I said "Well, you did say you thought it might be fun to see what fisting felt like."

"Ya, I did but...oh what the hell....be really gentle and stop if it's too much."

That got Bonnie's attention as she said, "Holy shit, you're serious? You're actually going to see if his hand will fit into your pussy?"

"I've masturbated with a big cucumber and a 750ml pop bottle before. It took lots of lube and I had to go slow but holy shit once they were in, it felt amazing!"

"I've got to see this!" and with that, Bonnie moved so she could see better as I made sure my hand was well lubed and then spread some on Annie's pussy. She was slick enough that I skipped using one finger and only used two to make sure she was slippery enough. Three fingers went in easily but four took a bit of gentle pushing and turning. When they were in almost to my thumb, I heard Bonnie whisper, "oh damn!"

After I made sure that she was ok with four, I did what I'd seen in numerous videos and tucked my thumb into my palm and started working that in. That went well until I hit the widest part of my hand and then it just didn't seem to want to go any further. After a little bit of pushing, rotating and wiggling that didn't work, Annie said, "How about you hold still and let me push?"

I figured it was worth a try so I did my best to hold my hand steady as she began thrusting against it. I could see my hand slipping further inside but not much more. I was almost ready to tell her I didn't think it was going to work and then on her next push, it went from almost in to all the way in. There was a long, drawn out "Fuccckkkkk!" from Annie, "Oh my God!" from Bonnie and "Damn it's in!" from me.

Neither Annie nor I moved for about 20 seconds and then she started to pull back slightly and then push again. Each time she pulled back it was a bit further until almost all my hand was out before she pushed back onto it again. By now she was moaning constantly so the next time my hand was fully inside her, I curled my fingers into a fist. When she started to pull back, her eyes got really big but after a minute or so of thrusting, she was able to take my whole fist in and out of her pussy.

When I heard her mumble, "Gonna....cum....soon!" I kicked it up a notch and started rubbing her clit with my fingers. The extra stimulation put her over the edge and I felt her pussy suddenly squeeze tight enough around my wrist that I couldn't move my hand for a few seconds. I'd been pulling back so when she relaxed, my fist popped out of her suddenly and at the same time, she started squirting. The first one hit my arm and the second one almost hit Bonnie. Without stopping, I slid my fist back in and she screamed and squirted again, this time even harder. She kept squirting as my fist slid out and back in a couple more times before she grabbed my wrist and said, "Can't...no more."

I opened my fist then slowly and gently pulled my hand out which got one more, smaller squirt.

All I could do was watch as her pussy slowly closed to its original size. Bonnie watched as well then finally said, "Holy fuck, I've never seen anything hotter than you taking his whole hand inside you and then squirting that much!"

Annie was still quivering a bit as she said, "I couldn't see much but I've never felt anything like it and I know I've never squirted that hard before."

Bonnie looked at me and said, "Maybe, just maybe, I'll reconsider and let you try that with me sometime."

Annie chipped in with, "as long as I get to watch!"

That got a "Mmmmm" from both Bonnie and me before the two of us headed back to our room, curled up together and crashed for the rest of the night.