Betting to Bedding

When we were still lying in bed the next morning, Bonnie and I talked and decided we were both fine with Annie joining us occasionally for sex and later when we asked her, not only was she good to join, she even suggested that she might enjoy being part of our bets occasionally. I looked at Bonnie, Bonnie looked at me and we both nodded so we told Annie we liked the idea too. After talking for a bit about the only thing that Bonnie wasn't sure she wanted to try was going down on another woman and Annie wasn't really interested in anal but they were open to pretty much anything else.

Now that we were all involved sexually, the frequency of our 'bets' died down over the next month or so but the frequency that two or all three of us had some really good sex went way up. It turned out that the 'quiet' Annie had a definite kinky streak that both Bonnie and I totally enjoyed. One Saturday, the three of us had been out to a party but it wasn't great so after a few drinks, we'd come home to have a few more and a few 'edibles' as well. Now all three of us were on the couch, somewhat watching tv and randomly touching/teasing each other when suddenly Annie said, "Anyone else horny and up for some fun?"

When both Bonnie and I agreed, she said "Ok, I was thinking of an 'anything goes' evening."

Bonnie and I weren't totally sure what she meant but with the buzz we had going, we were pretty sure it would be fun so before long we were all naked and on the bed. "What exactly did you mean by 'anything goes'?" I asked Annie.

"Well, we know what we've done with each other but usually we kind of 'plan' what we're going to do. I was thinking we just start and do whatever comes to mind at the time."

Bonnie giggled and blurted out, "I want to get eaten!" followed by Annie saying "I want to get fucked!"

I flopped onto my back and said, "I think I can do both - how about Bonnie straddles my face while Annie rides my cock.

Bonnie quickly nodded and was moving to straddle me when Annie quietly said to her, "Or maybe I could eat you while Dave fucks me from behind?"

Annie and I talked a few times when Bonnie was out and she'd mentioned that she'd been thinking she might want to try licking Bonnie's pussy but wasn't sure if Bonnie would be into it but I guess she'd decided to see.

Bonnie just looked at Annie for a few seconds and at first, I wasn't sure what she was going to say until she smiled, rolled onto her back and said, "Sure, go for it!"

As much as I wanted to slide my cock into Annie, I really wanted to watch Annie eating Bonnie for the first time so I shifted so I had the perfect view of Bonnie getting the first few licks from Annie's tongue. It didn't take long for her licks to be firmer, longer and more confident and it also didn't take long for Bonnie to start moaning about how good it felt. I watched for another minute or so and then moved behind Annie so I could give her the fucking she'd asked for. I couldn't resist bending forward to give her pussy a few nice long licks and she was already so wet she was almost dripping.

I gave her the full 7 inches in one thrust, driving her face deeper into Bonnie's pussy which got a moan from both of them. Looking up at Bonnies face as she got eaten, how hard her nipples were, Annie's moaning and seeing Annie's face buried between Bonnie's legs meant I wasn't going to last long but I wanted to try and hold back until Bonnie had at least one orgasm. Thankfully it didn't take Bonnie much longer to cum or I wouldn't have lasted and soon I was filling Bonnie's pussy with spurt after spurt of cum.

Annie pulled her mouth away from Bonnie's pussy long enough to moan, "Oh fuck ya, fill me up!" and then looking up at Bonnie she said, "Damn your pussy tastes good, I wish I'd done that before. Why don't you try it?"

Bonnie looked at her and said, "I....um....I've never....maybe...but you're full of cum right now."

As Bonnie was answering, Annie was slowly moving up her body and when Bonnie finished, she leaned forward a bit and whispered, "Well, you've tasted plenty of Dave's cum so the only new thing would be my pussy. I loved making you cum with my tongue, why not give it a try?"

By now she was pretty much over Bonnie's face and I could see her tongue coming out as she gave Annie's pussy a tentative lick. "Mmmm, that's it! Keep going!"

'Keep going' she did, it wasn't long before I was treated to the site of Bonnie digging in with her tongue and getting every bit of cum that oozed out. I thought it was almost all out and then Annie half moaned, half screamed and totally came. When she did, there was a big squirt that was a mix of her cum and mine and it totally coated Bonnie's face. When Annie shifted moved off her face and saw the result, she grinned and moved so she could lick some of it off and to my surprise, they were soon sharing a long, hot kiss as well.

After they separated, Bonnie looked at me and said, "I still want to feel your cock in me but it doesn't look hard enough".

With a grin, Bonnie threw in, "Maybe I can fix that" and with that she rolled over so she could start licking and sucking me to full hardness.

I was at that point where I wasn't soft but wasn't hard either so while I definitely started getting harder, I knew Annie would have her work cut out for her to get me totally hard again. After a few minutes, I could see Bonnie moving up behind Annie wearing the harness and strap-on.

I couldn't really see what was happening but it looked like at first, she just rubbed and fingered Annie's pussy then used a lubed finger from the other hand to play with Annie's ass. I felt Annie moan around my cock so I was pretty sure she was enjoying it then Annie shifted closer and I heard a soft "Oompf" from Bonnie.

Right after that, Annie said, "Way back you listened while I used this on Dave, why not see how it feels?"

As she talked, she must have been easing it into Bonnie's ass because Bonnie said, "I usually don't like anal but seeing as you're already partly inside and it feels pretty good, you might as well keep going. Just be really gentle, that feels huge."

Just at the point where Bonnie had it all the way inside, Annie looked up at me and whispered, "You bastard, you knew what she was going to do and didn't say a word - I owe ya one!"

She was smiling so I knew she wasn't actually upset and went back to sucking me. Just knowing that she was getting her ass fucked at the same time was enough to get me from 'really firm' to 'rock hard'. By now Bonnie was thrusting harder into Annie which pushed her onto my cock with each thrust and it didn't take long for that to make me cum. Usually my second load isn't as big as my first, but it felt huge and from the look on Bonnie's face I think she felt the same.

As soon as I finished cumming, Annie moved forward and the next thing I knew, her mouth was on mine, her tongue was parting my lips and a good portion of my cum was flowing into my mouth. When she moved forward, that pulled her off of the strap-on which let Bonnie move to see what was happening. I still hadn't swallowed all the cum so I grabbed Bonnie, rolled her onto her back so I could kiss her and let it trickle into her mouth as we kissed. We spent the next minute or two kissing and swapping the cum then Bonnie grabbed Annie to swap some of what was left in her mouth. Eventually Annie kissed me and I was surprised that I could still taste traces of cum from her mouth.

I wondered if things would change or if we'd get tired of what we were doing but by the time I'd been living there a year, we were still enjoying bets (both sexual and not sexual), having great sex between us and we were all getting along just great. Occasionally it would be just Annie and Bonnie having sex and I always knew when that had happened because they'd both be horny as hell when I got home and when we kissed, I could usually taste pussy on one or both of them.

Our best laugh was when Rob called one evening to say he'd broken up with Robin and wanted to know if I wanted to move back in with him because Robin was hoping to move back in with Bonnie and Annie. When I said no, he laughed and said I must be getting some from either Bonnie or Annie and I just said "YUP!" but wouldn't tell him which one. If he'd been there to see the grin on my face, there's a good chance he would have guessed that it was both and understood why I had no plans to go anywhere!