The whiskey bottle diary, first entry part1. [M][MF] [mF][str8] [VOY][ORAL][MAST]

The whiskey bottle diary, first entry.

I walk a fine line between living a good life, doing all the right things, morally and expectation wise, and living totally free. I enjoy being the guy that does his best to take care of business and make sure the people who need me have their needs fulfilled and more. But it's a struggle for my spirit, that just wants to fly.. down every new road, into the unknown or even the partially known.. just to see what's down there. It's adventures like that, that drive me through the ordinary and mundane cycle of work eat sleep pay bills be broke do chores. The difference now is that I'm older and care a lot more about everything in the regular world that's going on around me. So my adventures are more refined, and direct to the things I want to explore. This is a story of one of those things. It gets a little uncomfortable at the end, so I ask that you, the reader, keep an open mind and understanding of how things ended up the way they did.

Now sit back, relax.. while I pour myself a shot of whiskey and tell you my story..

I have a friend, who I am very close to. The kind of friend I can talk about anything with, and we do. We have the best conversations, the kind that go on for hours, far into the night. We can share our different views on things and totally get where each other are coming from, and even share our wildest thoughts with each other. It's always interesting sharing thoughts with her, and there's a total trust between us that nothing we discuss will ever be held against the other. And yes.. there is also some intimacy involved from time to time, so you can get that I know this friend very well. So when this friend had shared with me an idea of something she wanted to try, but needed my help with, I was all in. My friend wanted to be with a complete stranger, someone she knew very little about, who knew very little about her. She knows that I've always wanted to have sort of a fly on the wall experience and wanted some back up just in case things got weird. So we sat down together, with a bottle of whiskey, and created our plan. Now if you've ever had much whiskey, you know well that there are things you just wouldn't do, unless you've been drinking whiskey…

We discussed all the many different options in an experience like this, the ways to make it happen, the things that could be done, limits, places, what my part would be, how to pull it all off, and finally, we filtered through the guys until she chose the right one. SH he wanted someone clean, local, easy going, and 420 friendly. The girl is a smoker, and the best way to get her to relax is to blaze it up with her and not get weird. Saying that you're cool with her doing it, but not doing it with her is only 50% of what she wants, and this was meant to be a no compromise situation.

So we found this guy that was near enough and totally down to get high and have some fun. She wanted to suck his dick, and pretty much just that, for her first time out. We both agreed that that was the safest thing to try and much easier to control. But when they started chatting about it, things took a turn, and I could see that she was excited about it. The guy had stated that he loves to perform oral as well as receive. My friend is a squirter, but cannot make herself squirt, and as far as she knew at this point, I'm the only one who could ever make her squirt because we learned about this together. (This is how close our friendship is, and why I love being her friend hahaha!). Right before she is about to ask this guy if he's aver been with a girl who squirts, she gets a message from him, asking if she's ever squirted. Game change no.1 is on. She then sends him a picture of her beautiful labia. This leads the conversation into a little bit of cyber sex scenario, that has this guy as a boss in a suit, and her as his slightly submissive secretary. She falls right into it. I think something was said about being professional only at each others professions, and totally loose otherwise. Not important though. What's important, is how excited she's getting over this. See.. this girl is a total lady in the streets type. Sweet, caring, legit by the laws of morality and treating others as she would like to be treated. She doesn't manipulate to get what she wants, isn't one of those narcissistic "mirror selfies all over social media twice a day" girls. Very beautiful and sexy, but with no desire to use it to her advantage or create an army of white knights, ready to jump in and save her over every little situation that doesn't go her way. (Harsh description of the extreme opposite, I know. But you get what I'm saying..).

Back to the story..

Plans form into this guy getting a hotel, wearing a nice suit, and meeting in a decent sports bar, rather than a coffee shop or some shit hole bar. I mean, shit hole bar is ok, but coffee before oral sex acts? Eww! But anyway.. she is to be dressed professionally as well. Now at this point, I'm just an observer, maybe a little bit of an advisor. This is something she has never done, and besides being inexperienced at it, she's nervous as shit, and wants me there to help make sure she is safe and doesn't get in over her head. I'm street smart, through my life's experiences, and have a good feel for people, surprisingly, even through the internet. As their chat goes on, the dude almost immediately starts talking butt stuff, and sending her pics of chicks with vibrators up their asses. This has me telling her to be cautious, and very specific to him what is go and no. She is very capable of ass play, and even enjoys it, but I caution her by telling her that guys get a little crazy over it, especially if they've never experienced it and think they're going to. It's sort of like the old children's book "If you give a mouse a cookie..". (Yes, I referenced a children's book during a sex story. Those who know it, will get what I'm saying. That's all.). But she never quite gets specific over some of the things he throws out there. I don't know exactly why, she isn't the most assertive girl, or maybe.. she is open to the possibility. That thought turns me on even though I'm starting to worry about her safety. So they get to the point where this guy offers to get a hotel room, another turn in the plan that takes it further out of her control, and mine. I don't want to sit inside this hotel room like a fucking bodyguard, or pimp, or straight up weirdo just watching these two and cramping their experience. But being the good friend I am, I suggest a specific hotel that will work just right for their "scenario". They exchange more plans, agree on it, and she messages him saying, "I just want to be clear that we are not fucking. I don't want you spending money on a hotel and thinking you deserve whatever you want because of it. I promise it will all be worth your while." And this promise is legit. Girl can suck cock better than a porn star. She really, truly enjoys doing it. The guy never messages back with a specific acknowledgement of what she said. This fuels my uneasiness of the direction this is going even more. But plans move ahead..

Up until now, we've been working on this together, and it's been a lot of fun. Very stimulating and plenty of playing with each other. But I needed a little break from it, and she had to go out of town with her family. So I said, "just work on this on your own, and I'll check in or be available when you need my help." She left town, I went back to my regularly scheduled programming, because shit was piling up. I had a very hard time staying focused though. I was right on the edge of fulfilling a sexual fantasy that was on my bucket list of must do's. When the night rolled around, I decided I needed a break from the life stuff too, and went to a bar for some drinks. Because of this, I wasn't available as promptly as she needed me to be, to help her online. So she went ahead with her planning, on her own. Here you go, kid. No more training wheels. I got back in that night, caught up on their online activities, and got myself off with a little bit of fantasizing how this would go. They had agreed to meet the following night, which seemed a bit of a rush since she was going to be driving all day. I had come up with some ideas while Sunday morning lounging in bed, and shared them with her…

Meet at the bar. He's in a suit, you're dressed professional and cute, not super sexy, but have on some shoes that push it slightly. She has great legs, and had sent him a couple pics of her feet up on her desk at work, in heels. He responded very well to them. This is a full blown role play among strangers, that is about to jump from a cyber fantasy to reality. But anyway..in her car, she is to have a bag of extra clothes. Short and tight skirt, thigh high stockings.. When the leave the bar, assuming all goes well, they are to meet at the hotel and smoke some weed in her car together, before going in. The original plan from her to him, was he satisfy her orally first, then she blows him. And she might even blow him again if he can handle it. But I suggest to her, blow him in the car first, in your professional clothes, after you smoke together. This gets his tension out and makes it a little easier to control when they're inside the room. He won't be as eager. It also gives him time to work up again for a second round. I tell her to ask him to cum on her face, and take a picture. Send me the picture, then I'll know they're moving up to the room, and it gives me a little something to enjoy while I wait. It's also less for her to swallow and possibly get upset stomach from (this shit does happen), and better to get a full facial, than a second round dribble. I also instruct her to then remove her panties and leave them on the floor of the car, for me. I want to feel how wet she is from all this. Remember, she's a squirter, and gets very wet. She also gets very turned on by sucking dick, and this whole thing has her going as well. Since I am kind of just hanging around, and may or may not get what I hope to out of all this, I at least want a few souvenirs. My sexually diabolical mind is in full effect now, beast mode. When they get to the room, she is to then go into the bathroom, change into her sexy outfit, then come out into the room and make contact with me..

We had also formed a plan on how I was going to get to be the fly on the wall. Laptop video chat was instantly ruled out. Too similar to me just sitting there. I didn't want some guy trying to put on a show for me, or even worse, talking to me. Recording video on a mobile was a possibility, but I figured the phone would get chucked as soon as things heated up. We discussed maybe a "pocket dial", but just audio, and by crappy cell phone wasn't enough for me to get an idea of what was going on. Remember, this is also about her having back up in case the guy decides to butt rape her or worse. We eventually settle on video chat by phone, I can darken my camera so I'm not seen, but he has to agree on it. She asks if he's ok with video and pictures, he says yes, but don't get my face. Sounds like a go, but she does not get any more specific than that, and that's where she made a mistake. I kept trying to push her to be more specific to the guy, but she was just like, "don't worry, I've got this." More feelings of uneasiness for me, but this is her gig and I'm just lucky to be this much a part of it.

After she comes out into the room, dressed sexy and naughty as fuck, he gets to eat her pussy, and try to make her squirt. Then she's going to suck him off one more time, and leave. No staying all night, cuddling, getting to know each other.. that part is limited to the bar at the beginning. She LOVES my plan. Every bit of it. Says it's fucking hot and yes, she'll do it. I'm like ,"fuck yeah, I live for this kind of shit right here!" The evening rolls in, he sends her a message saying he can't do it that night. Disappointment follows, but she stays cool about it and asks when, he says tomorrow night, and she politely but firmly tells him if it doesn't happen, that's his last chance. Since we were both excited for this to happen, we decided to go for a drink, and just have a chill evening as friends, talk about other things. But then came the shots of whiskey…

We were sitting together in a quiet bar, at the bar counter. There weren't many people around. She was wearing a short, flirty summer dress and flip flops. Lots of leg showing, and because we sit close, they kept touching mine. I eventually set my hand to rest on her thigh, just above her knee. They way she shifted toward me when I did this, invited me to move my hand up a little further. Me being a leg man, and her being so pretty, got me engine revving. And of course, there was the whiskey.. So we finished up, and left the bar. The night was warm and clear, beautiful stars in the sky, and the smell of nearby summer ocean had us both feeling a few levels above. We opened her sunroof, smoked a bit of really good weed, and started driving back toward her side of town. Along the way, she asked me to pull over at this parking lot by the beach. I figured she wanted to burn some more, maybe even take a starlit stroll along the wet sand. But I was hoping too, that she was wanting to have a little fun with me, since she'd been so worked up. My wish came true when she invited me into the back seat, and lifted up her skirt, asking me to play with her pussy. It was already wet, and very warm. It wasn't long before she had my cock in her hand, and we were sideways, me fingering her, her jacking me off. I felt her pussy swell, getting ready to squirt. I'd instructed her to hydrate all day, so that she would have plenty of liquid to share, and it would be clean, less of a strong smell. She was already at that perfect stage of her woman cycle, when her pussy had no strong scent or taste, and her juices were thick and slippery. I grabbed her denim jacket off the floor and stuffed it under her ass. She knew right away that she was free to open her flood gates and not mess up her car. That splishy splashy, gushy sound….Then I was in her mouth. She was hungry for a cock, and I was the one feeding her. There was a shit ton of parking lot activity that was very distracting, but her windows are super tinted and I didn't give a fuck about being seen throat banging a hot chick. activities eventually quieted down around us, and soon she was on the seat on her hands and knees, skirt up over her ass, begging for my cock. I contorted into position and started giving her the cocking she had been craving all day. All week probably. When it was time to cum, she told me she wanted to swallow, and whipped around just in the perfect instant to catch my firepower all the way down her throat. As soon as her mouth was around my cock, I eased her head forward to the back of her throat. But instead of bottoming out there, she opened it up and I felt my cock head enter a tighter, deeper spot of her throat than I've ever been and spurt…spurt..spurt…spurt..at least five or six full shots of my cum went down her throat without her even gulping or gasping once. She pulled back a little and suck stroked me through the rest of my pulsing, before finally sitting up and wiping her cum smile with the back of her hand. She told me she just discovered something new, a cum shot straight down her throat with no swallowing required. I was turned on again with the thoughts of her pending adventure..

Source: reddit.com/r/sexystories/comments/3h8xal/the_whiskey_bottle_diary_first_entry_part1_mmf