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This story has its genesis in real life events and real people. I've just imagined it going a bit further than it actually did. Enjoy! I was in my mid-20's, in supreme physical condition, and in a relationship with Cass. Cass was a year younger than me, average height, brown hair, pretty face with an athletic build herself and an absolutely magnificent pair of DD tits that, at her age then, just sat there. She tended to dress plainly and conservatively but what was hidden beneath her clothes was simply incredible! At this stage of our relationship Cass was, it must be said, sexually unadventurous. After we had gotten to know one another I had revealed some of my escapades in the past – which shocked her somewhat – and I think it wasn't until she really got to know a few new girl friends in our social circle that her mind was slowly opened to new and exciting possibilities. Hearing her friends talk of bisexual experimentation and threesomes she was becoming less shocked and more curious, to the point where she eventually started to bring these things up in our conversations as well. One night Cass had mentioned that she'd be open to the idea of, as she put it, being in the bed whilst I had sex with another woman. At the time Cass's best friend was a girl named Stacey. Stacey was perhaps a year or two older than us, again average height and build, with dyed blonde hair and nice C-cup breasts that she managed to show off to mouth-watering perfection with the right bra and V-neck top. She was also divorced with two young kids – a textbook MILF. We saw a decent amount of Stacey, who would sometimes tag along with us on the rare occasion that her ex had the kids and she wasn't dating, but mostly we'd spend the evening at her place and just drink and chill once the kids had gone to bed. It must be said that I found Stacey to be a bit of a tease. It was all talk, and always in the open with Cass there to hear it. It was never anything that she couldn't laugh off as a joke at the time, and as such I didn't take a lot of notice to be honest. It all came to a head, however, when Cass was on the phone to Stacey telling her about her first experience sunbathing topless – at my request – at a public beach that day. Stacey asked Cass if I would mind if she joined us next time, as she had always wanted to go topless at the beach, but was too chicken to do it alone. I couldn't believe my ears! Stacey was clearly teasing me, and I played it up completely. After that, I felt I had license to suggest to Cass that perhaps Stacey would be suitable to help us realise some of our fantasies. She was non-committal but didn't veto the idea. Not long after that, Stacey's flirtations seemed to get a little more covert and, after a while, even a little more physical. She still made the odd joke with Cass present, but now she'd sometimes follow that up when Cass wasn't in ear shot or had left the room. And then the little touches started; initially quite innocent but then progressively more inappropriate, until one day at her place she patted me on the ass whilst telling me that she loved the fact that I always wore shorts. I had always been careful to respond in good humour but not actively encourage the behaviour. Secretly I was absolutely loving it of course, but by this stage I felt I had no choice but to tell Cass before it went too far. If I'm being honest, it was a pretty big stroke to the ego; I just hoped she didn't end the friendship over it. So tell her I did, trying to play it down as much as possible. Cass clearly wasn't pleased, but instead of confronting Stacey about it she wanted to see how far Stacey would take things if I reciprocated. So I was instructed to play along, but not actively encourage her or up the ante in any way, and to report anything and everything as soon as possible. I suggested that the whole 'forbidden fruit' aspect that got Stacey excited in the first place might kill it all if I was suddenly keen. In my gut however I suspected that going down this path things wouldn't end well, but at least it was going to be a little fun whilst things lasted. My challenge was to draw this out and enjoy it as long as possible! Cass seemed eager to spend as much time as possible in the ensuing weeks hanging out at Stacey's, no doubt wanting to test her intentions. I started out by responding suggestively to Stacey's little jokes when we were all together, giving her a little smile when she thought Cass wasn't watching. Cass pretended to either not hear the banter, or simply to ignore it. Cass also started to make herself scarce a little more often, and for a little longer. Stacey's behaviour hadn't really escalated for a few weeks now – still the odd touch here and there but nothing more – and I thought that was the end of it, until one Sunday afternoon. We arrived at Stacey's early while she was still putting the kids to bed. Stacey wore a stretchy green and white striped singlet top and a pair of white shorts. It wasn't long before I realised that she wasn't wearing a bra, and although the top was likely designed to be worn that way, I had never seen her wear anything that hugged her body like that. I was mesmerized by her bra-less tits, the outline of her nipples clearly visible, and had a hard time not staring at them. And so it was that a few hours later that I found myself doing exactly that, with Stacey bending over in front of me clearing pizza boxes from the coffee table, straight down her top at her glorious cleavage. She suddenly looked up, straight at me, gave a quick gasp, stood up, turned towards the kitchen door and and walked away. I knew I was busted, but also had the feeling that there weren't going to be any adverse consequences. Stacey emerged from the kitchen only a few moments later, cloth in hand, and walked straight back to the coffee table. She made a show of bending over again, wiping the table and generally fussing over nothing. Cass was conspicuously absent still. "Are you looking down my top again?" she asked quietly without looking up. "Yes" I replied matter-of-factly, knowing now that that was exactly what she wanted to hear. She continued to wipe for a few more seconds, her boobs jiggling side-to-side with each motion. She stopped, looked up at me again, and smiled. Then she shot a quick glance at the kitchen door, turned back to me, and reached over and cupped my semi-hard cock in her hand for no more than a second. Then she stood, checked the door once more, and whispered, "So you like what you see!" and marched off again triumphantly. I sat there, heart racing, my cock only getting harder. I realised that this was probably the game-changer. Cass wouldn't have an issue with me salivating over Stacey's breasts or even unashamedly looking down her top, but I couldn't imagine her forgiving Stacey for what she just did. I also realised that this was likely the last chance I'd get to reciprocate, and I was going to make sure that I copped a good feel, especially since it would be sanctioned by Cass in the name of catching out Stacey. And so about half an hour later, heart pounding and blood flowing to my cock, I followed Stacey into the kitchen to grab another drink from the fridge. As she opened the fridge door I came up behind her, and pressed my semi-hard erection into her white shorts. Wanting to make the most of the opportunity, I reached around and caressed her breast through her top for a few moments, whispering, "Yes, I like what I see very much!" into her ear. I then stepped back and edged over to the sink, ready for her reaction. She closed the fridge door and, bottle in hand, turned towards me. She held my gaze for a moment before glancing down at the bulge in my pants, then over to the door. "You can't let her see that now!" she exclaimed with a wicked grin, and then walked out to Cass in the lounge room. It was a few minutes before I could leave the kitchen. I was delirious. Here I was feeling up my GF's best friend, behind her back albeit with her approval, and it was exhilarating! I knew I was getting caught up in the moment, just like Stacey no doubt, and I briefly entertained the idea of not telling Cass about tonight. Maybe I could get a bit further with Stacey before spilling the beans? My mind raced, trying to come up with a way for this not to end, but I knew it was futile. The frustrating thing was that if it wasn't happening behind her back, there's a chance Cass would be into it. What if I could convince Stacey herself to come clean – would it turn out differently? What to do? It was getting late... On the drive home Cass asked me what happened. She probed for details and I left nothing out. Cass couldn't see but telling her about it had me hard again. Cass didn't say much, she seemed deep in thought, likely plotting some sort of revenge, or at the very least how to confront her over her actions and possibly even end the friendship. It was hard to gauge her mood as we readied for bed. In bed, lights out, I suddenly felt Cass's hand on my cock. "What do her tits feel like?" she eventually asked quietly, rubbing my erection. I tried not to answer too enthusiastically, but it wasn't long before Cass had mounted me and was sliding up and down on my rock hard cock, bringing herself to orgasm. I'd be lying if I said that I wasn't imagining that it was Stacey grinding on top of me that night! As we lay chatting, coming down from the sex, Cass said to me, "One final test!" I was surprised, and to say excited would be an understatement. Cass explained that she wanted me to kiss Stacey, to see what she'd do! She wanted to know if this was Stacey just getting off on a little forbidden groping, or whether she was willing to go the distance and have an affair! At this point I didn't see that it mattered much, but guessed that Cass had already plotted her revenge; whatever went down she wanted to catch Stacey in the act this time! We started to discuss how that would happen but we drifted off to sleep. A few days later Cass exclaimed, out of the blue, "I've got a better idea!" She went on to explain that she thought a kiss was too easy for Stacey to explain her way out of, she could claim that I kissed her and that she was caught by surprise. She wanted to catch her doing something that she couldn't worm out of, something that was clearly purposeful, something perhaps even a little humiliating to be caught doing. She still wanted me to kiss her, and report back, but ultimately she wanted to catch her – sucking my cock! I was taken aback but my heart started racing. The very thought of that sent my head into a spin. I had no idea how I'd set that up, and said as much. In the ensuing days we tossed around some bad ideas until a few days later, Cass announced with authority that she had a plan. And it was a good one. Normally we'd see Stacey at least twice a week, sometimes more, but it was fast approaching 2 weeks since we saw her last. I figured that Cass was pissed and although she was plotting revenge, still couldn't face pretending that nothing was wrong. I was beginning to wonder if we'd even see Stacey again, but then Cass rang to tell me that we'd be hanging with her this Friday night, at her place, no kids. It was on. — Continued in comments — hereforthesex69 [2


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