A lot has changed in the past six months. Sandy, my sexy sister-in-law, established herself as a top-notch webcammer, earning her well into the six figures. And now, she's branching out into custom content and full-length videos.
When I first got involved, my role was not what I expected, nor my wife. What was supposed to be me helping her set up any technology needed for her to be successful or assist when issues arise, ended up with me pushing the boundaries of what's acceptable for a married man to do with his sister-in-law. In the end, it wound up being a win-win-win. Sandy, my wife's sister, successfully embarked on her career as an adult content creator, my wife got the satisfaction of knowing I'd been a huge part of her success, and for me...well, let's just say I've been rewarded continuously, over and over, by both my wife Deborah and her sister Sandy.
To be honest, it almost seems like Deb is trying to win me over with sex. Like it's a competition or something. Which is silly. She already 'won' me when she married me. Either way, she usually drains me, in every sense of the word. Even after having given nearly everything I have to her sister. But, who am I to complain? If it makes my wife happy, I'll do it.
The interesting thing is, once I had Sandy on her way to becoming successful, we all assumed I'd step back and let her take the reins. Well, that plan was quickly squashed when it was evident that her viewers strongly desired to have me back in front of the camera. I honestly had no idea why they'd want to see me but Sandy assured me that it was a hot topic during all of her shows.
She ended up begging Deb to let her have me whenever she needed me. Deb's response was odd in that before she answered her sister, she ended up screwing my brains out that night and then made me promise that I'd always be hers. I really wasn't sure where this was coming from but I did my best to assure her I'd never leave her. The next day, Deb called her sister and told her she could continue to use me as long as she didn't cross any boundaries that shouldn't be crossed. Of course, Sandy quickly agreed. And, that's how I became a recurring part of her show.
It was awkward at first because it was basically a chat room full of guys trying to get Sandy to do unspeakable things, most of the time with me, or with a certain part of me. Oddly enough, I had gotten used to seeing my sister-in-law naked so that part wasn't so bad. And, if I'm being honest, she is one sexy woman, especially when she's trying to tease or entice me, or when she's in the throes of ecstasy.
I guess the oher thing that has surprised me is how comfortable I've gotten when being naked as well. It certainly never was planned but after taking repeated requests to 'whip it out', or to 'let 'em loose', I gave in a few times. And, the funniest things would happen when I would. One of them being the sense of admiration which seemed to ooze from the screen. Even though it was typed text, I could feel the viewers' emotions. It kind of made me feel like a rockstar, or something.
But, as soon as it was out, the requests started flying in. Most of it vulgar, but all along the same lines. They all wanted Sandy to take my penis in her, one way or another. I got to say, these guys have quite the imaginations. I was blushing most of the time but whenever I'd look over at Sandy, she just had this weird look in her eyes. The only way I can explain it is like she was a predator, and I was her prey. I know, it's crazy, but that's exactly how she looked.
Anyway, things really took off from there. She'd get so many tips and requests for private shows that it was almost overwhelming. Eventually, we had to tailor the show around the lead up to the big show, which cost extra. And, man, would these guys pay. Sandy kept raising the prices, and they kept paying. Of course, there was the promise of a spectacular show.
Funny thing is, I never considered myself a showman. But, something about Sandy and all the encouragement we'd receive, just made me want to do the best I could. More than anything, I didn't want to let my wife down. This was a big sacrifice for her with me being away from home late into the night. I wanted to do whatever I could to help her sister...within reason.
Thankfully, Sandy was there to guide me through everything. I really can't thank her enough. She just has this unique ability of explaining things in a logical manner, helping me get over any qualms I might have about certain aspects of our working relationship. I think she explained it best when she simply told me to think of her as my boss and that as her employee; I should always keep her satisfied.
I mean, sure, there's some boundaries I'll never cross. Like, I'll never make love to Sandy the way I do my wife. Other than that, I've come to realize there isn't much I wouldn't do for Deb and Sandy.
I guess that's why I find myself now arriving at Sandy's apartment sixty minutes earlier than before. Maybe I should back up. I think I mentioned how rather colorful some of the requests can be that come in through chat. Well, one of the most common requests involve having Sandy take my penis as far down her throat as she can. Honestly, I had no idea what they were talking about. I mean, she's been giving me blowjobs regularly and I thought they were amazing. Why would she need to take more of me in her mouth?
After some explanation from Sandy and further comments from the guys, I finally understood the objective, but I was still fuzzy on the rationale. Either way, Sandy thought about it for all of two seconds before exclaiming that she'd love to do this for me but admitted it was going to be quite the struggle given my size. This only served to inflame the guys more and they got even more riled up at the possibility of seeing her struggle to get me down her throat.
I still wasn't sure why she'd torture herself like this but Sandy was determined and went about setting up a private room and spelling out what it would take for her fans to get into it. It wasn't long before we had over 200 guys in the private room and Sandy was ready to begin. Me, well, I'm always ready. Not because of some superhuman power or anything. It was simply because Sandy kept me in a constant state of arousal with her tight sexy body, not to mention her slick hand constantly gripping my shaft.
To make a long story short, she struggled. Boy, did she struggle. And, in the end, she could only manage to get about half me into her throat. I felt so bad for her. She had tears streaming from her eyes and her makeup was a complete mess. It wasn't a sad cry, though. I think she just put in so much effort, it was all she could do. And, given how bad she was gagging and all the saliva that was running down onto her perfect tits and all over my penis and balls, I'd say she put in maximum effort.
I did my part the best I could, supporting her all through it, and of course keeping my dick hard as a rock for her. She eventually ran out of steam and I could tell she was thinking she disappointed me and her fans. It ended up being the furthest thing from the truth. I thought she was crazy for even trying and her fans were overjoyed, sending tips on top of tips, virtual applause, and an extraordinary number of pics of their spent penises.
She was appreciative of it all and with a bit of sadness, we signed off. I immediately went into comfort mode and took my sexy little angel into my arms and carried her into her bed, where I snuggled up against her, nestling my still hard dick between her perfect ass cheeks, and rubbed her shoulders. It didn't take long for her to settle down and before I knew it, she'd opened her legs a bit and guided my member into her sex.
