Betting to Bedding - Pt. 01

Hi, I'm Dave and seeing as I get hard every time I think of what happened, I figured others might too. I was in college and sharing an apartment with Rob. I didn't have a lot of money so it didn't take long to find that I couldn't afford much. Rob already had a fairly large, one bedroom apartment and as it turned out, 'much' eventually turned into us sharing that apartment because he needed the help with the rent. All in all it was ok, the bedroom was big enough for two twin beds and a couple of small dressers. We'd known each other since high school so it wasn't that big a deal. If one of us brought a date home, the other would either crash elsewhere or sleep on the couch.

By the time we were halfway through the first year, Rob was pretty serious about a chick named Robin - serious enough that I was spending more time on friends couches or ours than I was in my own bed. One evening I came home and Rob and Robin were there and after a couple of drinks he told me that she was going to be moving in so I'd need to find another place but I was welcome to crash on the couch until I did. It wasn't exactly a surprise but I was hoping it wouldn't be that soon.

For the next week or so, I spent my spare time looking for a place and constantly came up either short on money or it was too crappy to live there. I wasn't sure what I was going to do when I got a call from Bonnie who was Robin's old roommate. Bonnie, Robin and Annie had shared a two-bedroom apartment with Annie in one bedroom and Bonnie and Robin in the second, bigger bedroom. At first, they'd enjoyed each having their own bedroom but couldn't really afford it. They'd been looking for another girl to rent to and either didn't like the ones who applied or didn't think they could come up with the rent.

Bonnie knew I was good for it and while we weren't best friends, we'd partied a few times so she knew I was a decent guy and they were already a bit behind on rent. They proposed that I could have the smaller room and they'd share the bigger room. If it didn't work out for any of us then I'd have to find another place. I was really tired of sleeping on the couch so I agreed and by the end of the weekend, I had everything moved in.

The first few weeks were ok, I was a bit uneasy living with two girls and I was pretty sure they felt the same way but pretty soon we got used to each other and it was a lot better. I got fairly regular glimpses of nipples without a bra, they saw me in boxers and a few times one of us would get a quick flash of the other going to/from the bathroom with little or occasionally nothing on. Now that I was seeing Bonnie on a regular basis, I found we had something in common - we both enjoyed making little bets on things.

Rarely did the bets involve money, it was just for the fun of 'winning'. Quite often the four of us would go out and sometimes other friends would join us either for a few drinks, a movie, some pool or whatever we felt like that evening. If we went out for a few drinks, we'd bet on who would sink a certain ball in pool or who could get the highest score in darts. Usually, the bet was for a drink or something similar. Once we were sharing the apartment, we found we were making silly bets on who could get the most pringles in their mouth or a staring contest with each other to see who would blink, smile or whatever first. Often the loser had to take the others turn to do dishes, clean up the apartment, etc.

Annie was much quieter, always did her share of the chores and then spent the evening on her laptop or went out by herself and seldom went out with us. It wasn't that she wasn't attractive - she definitely was but she just didn't seem as social as most people I knew.

It was during one of the staring contests that things started to change. We were laying on the floor (it was more comfortable than the couch for watching tv and as we stared at each other, I couldn't help but notice that she was wearing a low-cut top and no bra. She'd worn it before but the way we were laying, it was hanging loose and I could see her tits and nipples. That broke my concentration and I blinked right away. We usually went much longer so when Bonnie asked me what had happened, I stammered out, "Well, your top.... it's...I could see..."

Thankfully before I got any further, she figured out what I meant and quickly shifted so I couldn't see anything. I was expecting her to be mad but instead she just smiled and said, "Oh well, boobs are boobs and now you're doing the dishes tonight."

Glad that she wasn't upset, we went back to watching TV and I did the dishes before bed. Apparently, she was quite willing to take any advantage she could and I soon found her giving me quick flashes of her boobs while we were playing pool, darts or whatever and once after quite a few drinks, she challenged me to see who could crawl down the apartment hallway faster (we were pretty much past being able to run). I figured that was an easy win but she took off a bit faster but before I could recover, she flipped her skirt up and I realized she had nothing on under it. That resulted in my getting my arms tangled and falling on my face which really amused her, plus I had to take her turn cooking the next day.

Her boobs weren't big - likely between a 'B' and a 'C' cup but they were very firm looking and had fairly large, dark, puffy nipples. When she flipped her skirt, I found that her pussy was totally bare. I certainly enjoyed all the flashes and quickly found I also enjoyed stroking off later thinking about it.

I figured two could play at that game so a few days later I challenged her to a card game where all the cards were spread out on the floor except the aces. The idea was to shuffle the aces, turn one up, and then grab as many of that suit as you could until they were all gone then turn over another ace and repeat until all the cards were picked up. My goal was to get out of doing the cleaning that weekend but if I lost then I had to take her cleaning the weekend after. We were sitting on the floor so when she went to get the cards, I gave my cock a few quick strokes to get it hard (doesn't take much when you're only 21) and angle it so it showed down my pant leg.

It took her a few minutes to notice but when she did, she totally lost track of her cards and I won the first two rounds easily, she managed to win the third and by the last round, I was excited knowing she was sneaking looks at my cock so it was even harder. I'm not huge but seeing the tip of a fairly thick, 7" cock seemed to have her attention. When she protested the loss and I asked her why she said, "Well, it's not easy to play when your 'thing' is sticking out."

"Oh, and how's that different that you winning because you distracted me with your boobs or ass?"

She actually blushed a little before saying, "So seeing my boobs distract you, do they?"

"Well, I'd be lying if I said I didn't enjoy it. You seemed pretty distracted my seeing my 'thing' as you called it."

"Ya, don't take this the wrong way but I was surprised how big it was."

I knew right then that we'd opened up a whole new avenue and sure enough, a couple of nights later Bonnie wanted to go out with a couple of her friends after class but it was her turn to cook. I said that I'd cook for her if she did my next two nights of cooking. She thought about it and then suggested we play a single hand of poker which didn't surprise me because she usually won at poker. When I said no, she thought and then said "Ok, poker - loser cooks and has to flash the winner.

I pretended to think about it for a few seconds before saying, "Ok, you're on but it has to be full frontal flash, totally nude."

She agreed and much to her disappointment, not only did she end up cooking, I got to see her nude for the first time. I didn't get to see her for long but damn she looked good! I'm pretty sure she noticed me getting hard but didn't say anything.

From then on, while we still did our 'normal' bets but it wasn't uncommon for us to bet a flash, having to streak up the hall or if we were out sometimes flash a stranger. Sometimes I won, sometimes I lost but either way I think both of us enjoyed it. One night we'd had a few drinks and were flicking channels when we stopped on a pool tournament. Right away, I said, "I'll bet the guy on the left wins."

"You're on, let me guess you want to bet a flash, don't you?"

I thought for a second and likely the alcohol helped because I said, "How about a flash and a touch?"

I was fully expecting a "No way" but I guess the drinks had hit her too because she said, "Ok - but no more than 5 seconds of touching."

She won the first one and when I pulled my shorts down, she cautiously touched me for a couple of second before giving me a few quick strokes. I won the next two games, the first time I spent the 5 seconds feeling her boobs (her nipples got really hard when I played with them) and the second time spent it touching and fingering her pussy.

Inevitably by the time the tournament was over, we had no idea who was winning because we were both pretty much nude and making out on the floor. Right about then, Annie came in, saw what we were doing and with a quick, "Holy fuck!" she went to the bedroom and shut the door. I looked at Bonnie, Bonnie looked at me and we both started laughing.

At first, I wasn't sure if we were going to keep going or if that was going to stop our fun until Bonnie said, "Well if she's in that bedroom, how about we go to yours?"

I was all for that and it wasn't long before instead of just seeing and touching her pussy, I had my tongue buried as far as I could inside her and over the next 5 or 10 minutes, ate her through a couple of orgasms before I heard her say, "Your turn" and guided me onto my back.

I've had better blowjobs but none with quite the enthusiasm she showed and it wasn't long before I was moaning. When she heard me, she pulled back long enough to say, "Don't you dare cum in my mouth!"

"No problem, not everyone likes the taste."

"Oh, I'm fine with the taste but tonight I want to feel you cum inside me."

Damn! I was pretty impressed that hearing that didn't cause me to cum and soon I was enjoying the feeling of sliding my cock into her very warm, wet, pussy. She came again before I was all the way in and a second one a few minutes later. I'd never been a 'bar pickup' kind of guy, sex had always been with someone I'd been dating so this was different. There wasn't an emotional link, it was just raw, hot sex between two horny people. It didn't take long for Bonnie to get her wish and I emptied into her pussy which triggered another cum from her. Apparently, I was hornier than I thought because even though I softened slightly, when she reached down and stroked my cock, I quickly hardened again.

For round two, she climbed on top of me and rode me hard and fast. I could tell she was pretty much fucking me so she could cum and she did - four more times before I finally released a second load into her pussy. As she rolled off, I wasn't sure if there'd be any awkwardness or regret so was happy when she said, "See ya tomorrow - that was awesome!" before heading back to her room.

It was a bit awkward with Annie there at breakfast the next morning but all she said was, "maybe shoot me a text or something next time so I can decide if I want to come back right away or not?"

Bonnie just laughed and said, "things went from 0 to 60 pretty quickly but I'll try to either let you know or at least take it to the bedroom."

"Thanks...just make sure you take it to his bedroom or at least your bed - no sex on mine!"

She was grinning so we knew she wasn't mad and we all laughed harder when I said, "Not even if you're already in it?"

"No, not even if I'm already in it...although it could be interesting."