Betting to Bedding - Pt. 02

Read Part 1 here: Betting to Bedding - Pt. 01

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Having had sex and wanting more opened up a whole new type of betting. While we really weren't emotionally attached to each other, we quickly found we were a great match sexually so if we were home, a winner could easily get oral sex, or the loser had to masturbate for the winner and a couple of times the loser got spanked. The spanking was interesting, I found it slightly arousing (getting and giving) and Bonnie said the same but because we were both competitive, it was the winning that we enjoyed even more.

This went on for a few months and even if a bet wasn't involved, it wasn't unusual for Bonnie to end up in my bedroom or if Annie was away, for us to fuck in their bedroom. The sex was always awesome with both of us cumming at least twice and I think my record in one night was four times.

One evening the three of us were home and out of the blue, Annie said "Hey, I was thinking. I'd kind of enjoy a bedroom to myself and the two of you seem to get together somewhat regularly so what about Dave and I swapping rooms?"

Bonnie and I only thought about if for a few seconds before we both said, "Sure!"

That made it a lot easier for Bonnie and I to have sex when the urge hit us. One night Annie was out and we'd decided to have a few drinks. Even sober we were pretty open with each other so with a few drinks in, I wasn't too surprised when Bonnie looked at me and said, "Don't tell me what they are right now, but is there anything you're really wanted to do sexually that no girlfriend would do?"

A few things came to mind so I said, "Sure, how about you with a boyfriend?"

"Me too."

There was a bit of silence before I said, "Ok, you can't leave me hanging like that. Why'd you ask?"

Bonnie looked at me for a few seconds then said, "Well, whenever we have sex, it's really good and there's no real expectations."

Another pause before I prompted with, "And?"

"Well, here's what I was thinking. Could you come up with two or three things?"

Now I was getting really curious so I said, "Sure, and then what?"

"Then we write down three things we'd like to try on pieces of paper. Whenever we're both in the mood, we have a bet and loser draws one of the winner's papers. Whatever's on it, they have to do."

"That means we'd be doing them all anyway, how about we write down three but only do two - that way there's no guarantee which two we'll do. What it it's something that we REALLY don't want to do?"

"I thought of that but not sure, maybe they'd draw again and must choose one of the two of them plus something else."

"Hmmm, how about some sort of punishment?"

"Ya that might work" then after thinking about it for a bit she added, "once after you'd spanked me, Annie saw my red ass and said she wondered what it would be like to spank someone. Just the way she said it made me think that she's not as shy and naive as we think."

"Ok, that could be interesting - and nothing with pee, poop or bdsm type stuff."

Bonnie nodded and soon we were each writing down three things we'd always wanted to try. I didn't know what Bonnie wrote down but I was looking forward to her drawing mine and hopefully trying them. When we were done, we folded our bits of paper and put them in two glasses.

After looking at each other for a few seconds, I said, "Annie's not going to be home tonight - shall we do one now?"

Bonnie quickly agreed and we decided that the bet would be to randomly dial 20 numbers on speaker phone and see who could get the most people to tell us what they were wearing. Annie did pretty well and I wasn't sure I'd be able to beat her 11 but after a few refusals, my last two did it to give me 12.

I grinned and handed Bonnie my jar. She pulled one out, read it and said, "Anal sex eh? I'm not crazy about it but I've done it a couple of times."

We headed for the bedroom where we quickly undressed and she got onto the bed on her hands and knees, looking back saying, "You're pretty big so you'll have to use lots of lube and go really slow at first."

As much as I wanted to try it right away, I didn't want to hurt her so I grabbed some lube from my drawer and spent the next few minutes getting her pucker nice and slippery before working a finger inside. Her ass was really tight but she moaned a bit as my finger slid in so I fingered her with that finger for a little bit, then added a second one. Once two fingers were sliding in and out fairly easily, I lubed my cock and as I pulled my fingers out, I eased the head against her pucker before it could fully close. Damn she was tight but like she'd told me, I took my time and within a few minutes my cock was buried in a woman's ass for the very first time and it felt amazing. From her moans, it sounded like she was enjoying it too but it was only a few minutes before the tightness of her ass plus the kinkiness of what we were doing added up to me shooting my load in her ass. She hadn't cum yet so I figured I'd finger her to orgasm in a bit but surprisingly, she must have been close because just after I started cumming, she let out a loud moan and I felt her ass constricting and relaxing on my cock which just made me cum even harder.

Almost a month went by and then one evening we went out and at one point Bonnie said, 'I'll bet I can chug this beer faster than you!"

When I asked what the bet was, she just winked and said, "Slips!"

If she hadn't grabbed my cock through my pants, I'm pretty sure I'd have won but that threw me off and I actually choked on it a little bit. By the time the Uber dropped us off, we were more than a little tipsy and as soon as we got inside, Bonnie grabbed the glasses and said simply, "pick one!"

I grinned and pulled one out. My first reaction when I read "Eat me after you've cum" was 'no way' and Bonnie must have noticed the look on my face because she said, "You cum in my mouth, what's so wrong about you tasting it?"

Maybe it was her logic, maybe it was the drinks but, in the end, I agreed and we were soon playing around on the bed. I was just getting ready to slide into her pussy when she whispered, "you don't have to but I'd really like to do it like a video I watched. He was tied to the bed so he couldn't move while she straddled his face after he came."

I figured if I was going to do it, it really didn't matter how it happened so I agreed and while I think I could have pulled out of them if I'd wanted to, a few minutes later I was tied spread eagle and she was riding my cock for all it was worth.

It didn't take long to realize that this one was all about what she wanted and tied to the bed I didn't have much choice anyway. She had a couple of small orgasms before I exploded into her pussy. When I finished cumming she whispered, "I've wondered for a while what this would be like" and with that, she pulled off and moved up my body.

The closer she got, the less sure I was that I wanted to do it but again I didn't have much choice. Soon her pussy was right against my mouth and after a couple of licks, I found it wasn't too bad at all and started doing everything I could with my tongue to make her cum again. By the time we were done, she'd came three more times and each time she did, more of my cum was pushed out and mixed with her juices. I was surprised to find I was actually enjoying the taste of her juices mixed with my cum and was actually a little disappointed when she finally moved off my face.

"Holy shit! I enjoyed watching it online but that was nothing like feeling it. Now I don't think I could be with a guy for long if he wouldn't at least try it."

Usually, after sex we'd clean up and go back to our own beds but for only the second time since we'd started sharing a room, we spent the whole night sleeping in the same bed and when I woke up in the morning, it was to the feel of her sucking my cock. She'd gotten much better at it and after a few minutes I was cumming.

"I know you weren't too sure about following through on the paper last night so I just wanted to say 'thank you'!"

I grinned and said, "With that kind of a thank you, I might just do it again sometime."

Bonnie grinned back and said, "I'll certainly keep that in mind!"

We were just getting into exams so the next week and a bit was studying, writing and studying for the next one. After the last exam, we all went out to a local bar to let off steam and while we were happily getting drunk, I told Bonnie that I bet I got a higher average for the term than she did and I was willing to bet another slip on it. She took me up on it and it was felt like a really long week before we finally got our marks. When we did, she'd beat me by 2% so when we got home, she promptly pulled out the jar and with a bit of nervousness, I picked one of the two that was left. I had to read it twice before I was sure I hadn't read it wrong, the slip said, "fuck you with a strap-on"

Now I'd never had ANYTHING up my butt and I really didn't think I wanted to so I said, "I'm going to take a 'no' on that one.

Bonnie grinned and said, "Ok, I guess you get to go tell Annie that you need a spanking and then you can pull the last one and see which one you'd sooner do."

FUCK! I'd forgotten about the spanking part but I knew there was no way she was going to let me out of it so we headed to Annie's room and I knocked on the door. When I heard a 'come in' and walked in, Annie was sitting on her bed in the long t-shirt she often wore at night. When she saw us both come in she said, "What's up?"

I looked at Bonnie for help but she just grinned and said, "you tell her."

Looking at Annie, I said, "Well, you know how Bonnie and I like to make bets."

"Ya, for all sorts of things."

"Well, we made a deal that the loser had do something sexual that the other wanted but if we really didn't want to do it, we could say no."

Annie looked at both of us a little puzzled and said, "And where do I come into this?"

After swallowing, I said, "Well, we also agreed that if we said no then as a punishment whoever it was had to ask you to spank them."

I was watching her face to see if I could pick up her reaction and after a brief smile she said, "This could be interesting. Sure, I can do that. How many swats?"

Bonnie and I looked at each other before I looked back at Annie and said, "Umm, we never decided that."

Looking at Annie, I could almost see her change from quiet, shy and a bit naive to in-charge and confident. "Then I guess I'll have to decide for you and I pick 30 on each cheek. Drop your clothes and get over my knee."

I shot a quick look at Annie and it seemed she was just as shocked as I was. Apparently, I hesitated too long because I heard a sharp "NOW!" from Annie.

That got me moving and before she could say anything else, my pants and boxers were on the floor and I was over her knees. When Bonnie had spanked me, it didn't hurt too much, it was more of a 'ha-ha, I won!' kind of spanking.

By the 4th swat, I knew this was going to be different as it was already stinging and by the 10th, I was squirming. What really surprised me was that by the 20th swat I was getting hard and by the time she finished the 30th, it hurt like hell but also felt good and my cock was throbbing as much as my ass was. When I stood up to reach back and rub my ass, my cock was rock hard and right in front of Annie's face. She just looked at it, then looked up and said, "Well, now I see why Bonnie makes so much noise when you're having sex."

When I looked back at her, I could see her nipples were showing rock hard through her t-shirt and she looked somewhat flushed.

I looked over at Bonnie and I saw that she was rubbing her pussy through her pants. When she saw me looking, she quickly pulled her hand away and said, "Thank Annie for helping and let's go back to our room."

I couldn't be sure but when I gave Annie a quick, "Thank you!" I was pretty sure she licked her lips before saying, "You're quite welcome, any time!"

By the time I closed our bedroom door, Bonnie was already naked and on the bed.

"So, what got you so wet? I thought you said spanking me didn't turn you on."

"I'm really not sure! Spanking you didn't turn me on near as much as watching Annie spank you - that got me wet almost instantly and you didn't see but when you stood up, I could see a wet spot on her panties so I think it turned her on too."

I was all for fucking her right then and there but instead, she held out the jar with the slip of paper in it. When I pulled it out, I was totally surprised to read, "fuck you with a strap-on"

When I looked at Bonnie with a 'what the fuck' look on my face, she said, "we never said they all had to be different."

Fuck, she had me there and now it looked like I had my choice of getting fucked with a strap-on or getting fucked with a strap-on except now I could still feel the sting of Annie's hand on my ass. With a groan of acceptance I said, "Ok, let's get this over with. How do you want me?"

She just grinned and said, "Just like you had me the last time!"

It wasn't long before I was kneeling on the bed, ass in the air while Bonnie spent a few minutes spreading lube in and around my ass before sliding one, then two fingers inside. Honestly, I was expecting it to hurt a bit and not be enjoyable but I was wrong on both. Sure, I could feel myself getting slightly stretched but it actually felt kind of good. After a minute or so, I felt her fingers slide out and almost right away I felt something bigger pushing against my pucker. This time there was a bit of pain but still not as much as the spanking and when it finally made its way past the muscle that was trying to keep it out, I couldn't help but groan.

"Hmmm, sounds like you're enjoying this!"

I didn't want to say that it felt good so I said, "It's ok. You can go deeper if you want."

After a few more minutes of pushing just past the muscle and then pulling back out, she slid the dildo all the way in and then held it there. I felt her moving but decided instead of looking, I'd just wait and see what was next. When I felt the dildo sliding back out, she moved so she was kneeling right behind me and then I felt the push of a different toy against my ass. I was glad I'd taken my time when I fucked Bonnie in the ass because she was very gentle with mine. This time it took some more lube and lots of pushing before it finally slid all the way in. When it did, there was a brief bit of pain but then I felt a warm, tingly sensation run from my ass all the way down my cock. That got an even bigger groan and soon I was pushing back as she pushed forward.

I was a little disappointed when she pulled out but when I heard, "Roll over", I knew she wasn't done. Laying on my back changed the angle and now every time she slid into my ass, the head of the strap-on hit my prostate and my cock jumped. She seemed to enjoy that because she made sure she hit the spot as often as she could. I was enjoying it too and was close to cumming but couldn't quite get there.

"I'm getting close, fuck my ass with your toy and make me cum!"

"Wow, you're actually enjoying this! I'd love to see you cum while I'm fucking your ass with my toy!"

Finally, she took pity on me and started stroking my cock the same speed she was fucking my ass. That was all it took and my cock erupted. If I was masturbating and really turned on, I often hit my upper chest with cum but my first shot hit my forehead, the second right across my cheek and the third hit my chin and lips.

Seeing me cum must have been enough to put Bonnie over the edge because she started moaning and shaking as well. When she finally relaxed, she looked down at me, smiled and proceeded to lick the cum off my face.

When we finally parted, Bonnie said, "oh my god! I couldn't actually feel your ass around the strap-on but if that's what fucking my ass looked like, I can just imagine how it would feel. What did you think?"

"Well, at first I was pretty sure I didn't want anything up my ass. Once I felt your fingers, I realized it wouldn't be that bad. The first toy was ok and at first the second hurt a bit going in but after a couple of minutes it actually felt good. When you started stroking me, that put me over the top and I can't remember ever shooting cum that far."

Bonnie just laughed and said, "Ya, you look pretty hot shooting your cum all over your face, maybe I should have put that down as my third one!"

The next day before Bonnie got home, Annie asked me how my ass felt and when I said, "The spanking hurt but it's ok now" I was quite surprised when she grinned and said, "Who said I was talking about the spanking, the walls are pretty thin!"

I could feel the heat all the way from my head to my toes as I blushed, stammered and headed to my room. When I told Bonnie later, she just laughed and said that she hoped Annie got nice and horny listening to what we were doing. Of course, that put my mind into picturing Annie laying there masturbating as I got my ass fucked which in turn got my cock hardening but unfortunately Bonnie had to study for a test and finish a presentation so there wasn't time to take care of it that night.