High School Reunion Drinking Games

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A few years ago I went to my twentieth high school reunion. Coincidentally I’d also begun a fitness regime about a year ahead of the reunion. I didn’t really do it for the reunion, but over that year the reunion date did provide some motivation. After all the desire to impress a group of people that you shared five years of your life with in the distant past seems a common enough affliction. Since I wasn’t famous or rich the only avenue left to me to impress was via a regime of workouts. I didn’t have a PhD, but there was no reason why I couldn’t at least have a low BMI.

Our reunion was held at a reception hall near our old high school. It wasn’t a huge turnout, but it was a fun night. There was even some drama when Kate, my girlfriend from grade nine, bumped into me while I was hand talking with a glass of wine. Some spilled on her, it was an accident and of course I apologized. Apparently more was expected though, because friends kept coming up and telling me that Kate was upset with me and I should talk to her. It really was starting feel like high school again. Eventually I did speak with her and smoothed things over enough that people stopped bugging me about it. I suppose it would be appropriate for readers to expect this incident to segue into the story’s tryst, but that’s not how things turned out. Hooking up with an old ex might have made a good story, but I much prefer what actually happened.

This story is about me and another woman from the reunion. The woman that I ended up having a freaky fling with was a little red head named Casey who had been in my home room during our graduating year. Casey resided in a bit of a hole in my consciousness, having not seen her since high school I really only started to reformulate my memory of her after the reunion.

Back in high school Casey and I were part of an extended group of friends. I remember always being on pretty good terms with her, but we didn’t see each other that much outside of school. There were about a half dozen towns that sent kids to our high school and for whatever reason it was a rarity for kids from my town to visit the town where she lived. My memory may be imperfect on this point, but it seemed like my town had hardly any girls and the few girls that there were had long since been exhausted as romantic options. Another one of the town’s that was sent kids to our school seemed to be brimming with girls. As a result, a natural travel corridor developed between my all boys town and the other all girls town. Casey’s town just seemed to lack enough kids or at least a high enough concentration of girls to justify regular trips. Maybe if geographical circumstances were different we would have found our way to one another sooner, but somehow I doubt it would have been as great nasty fun.

I didn’t really talk with Casey that much at the reunion, but afterwards we became facebook friends and soon we were messaging each other with increasing regularity. Things started getting flirty pretty fast and really took off when I gripped about the overly public nature of some facebook messaging apps. I complained that I’d like to be able to ‘poke’, ‘defenestrate’, ‘drunk dial’ or send a ‘sex on the beach’ e-shot without the whole world knowing. Casey responded in agreement and mentioned that at least the direct messaging feature we were using was private, so for us whatever happens on facebook stays on facebook. Since we were both married there was an underlying invitation on offer beyond just commentary on facebook functionality.

I suppose the whole thing would be recognizable as a mid-life crisis. With no notable fault in my life or my marriage I was nonetheless hungry for one more taste of youthful indiscretion. I knew that I wanted to have a fling and it was pretty clear that Casey was declaring her availability to me. I usually know pretty quickly what I want with someone and I knew that with Casey I wanted sexual excitement. I wanted a fellow conspirator that I could look forward to sharing mutual adventures, but I also knew that adventures were really all I was looking for. I didn’t want to send my life up in smoke, but I did want to play with fire. Casey’s marriage was apparently on the rocks, but she did confirm that all she wanted was some fun on the side too. So with the terms set we began to hatch our plans.

It was around November when our facebook friendship crossed over to something more. However, I lived in Toronto, while Casey still lived in the same little town on the South Shore of Montreal. So while we were both ready to fuck like crazy, door to door there was over 500km separating us. The conceptual distance between us that existed in high school was replaced by actual distance, but at least now I had a car.

While the distance and circumstance precluded any immediate meetings our messaging became nightly events. We increasingly shared every detail about what we wanted to do with each other. Anytime I was alone with my PC, my cock would be out and I’d be stroking myself with Casey playing along on the other side.

29 Nov 2010



“Describe your cock for me.”



“Right now ısparta escort it’s hard and I’m stroking it ready to cum. Just thinking of meeting you and without a word taking out my cock, you taking it, licking off the pre-cum, rubbing it over your face before you take it in your mouth.”



“Wow, that’s just how I was picturing it. I’m getting so wet. Are you going to imagine me drinking it and make yourself cum?”



“Yeah, I’m thinking of jerking off into your open mouth. I’m thinking of coating your outstretched tongue with cum. Then I want to watch you swallow my load and show me your empty mouth.”



“Yum, sounds delicious. I bet you taste incredible. Go for it, I want you to cum while thinking about fucking my mouth. You’ve got me throbbing.”



“I’m getting so close.”

“What about you?”



“Actually I’ve been rubbing my pussy and getting myself off all night. I think this will be my second or third orgasm with you tonight: ).”



“That finished me, thanks. I’ve cum with the thought of filling your mouth in my head. Imagining your sopping wet pussy sure didn’t hurt either.



“Me too and I’m licking the juice off my fingers. I wish I could taste your cum too.”



“Nice! I can’t wait to see you do just that.

“Now I’ve got to get 3hrs sleep.”



“Well if it makes you feel any better I’ll be up at 5:15.

“Night. Can’t wait!”

Casey in particular would look back and question why we never got together in high school. I had to agree and while I’m sure I would have appreciated fucking her back then, somehow I doubted there would have been the same lack of restraint as we were currently considering. Initially I figured that Casey’s attraction to me was something recent, but the more we communicated the more my memories of her from high school returned. I vaguely remember a few times friends letting me know that Casey liked me. I remember too that I always though Casey was cute and there was something about her that certainly had me occasionally imaging how hot she would be to fuck. Of course as a high school boy that was a common preoccupation I had with a lot of girls. The biggest encumbrance though was that there was another girl that I was dating at the time.

Casey was about 5′ 4″ with red hair past her shoulders, hazel eyes and her best feature was probably her body. Her tits in particular, Casey was nicely endowed.

Plans with Casey were always increasingly pushing the sexual envelope and then one weekend after our first attempt to get together fell through things made another interesting progression. While revisiting the blow job she was going to give me, likely emboldened by a few scotches and a hard on I asked Casey if she would be happy if I did more than cum in her mouth? I was a little nervous awaiting her reply, but when the message came in I’d describe her response as a wobbly, but pussy moistened yes.

21 March 2011



“Well our visit is off. Our dog is really sick and we can’t put him in the car for five hour unless we’re willing to junk the car at the end of the trip. He seems a bit better today, but other than to see you, I can’t justify driving down just to come right back the next day. I don’t think the wife would buy into my reason for sticking with the trip.

“I’m so bummed out. I’ll have to reload for you on our next trip back.”



“Well I’m glad Marlin is feeling better. On a purely selfish note, I think I’ll cry. Oh well, guess I’ll just have to keep dreaming.”



“Sorry, I guess you really wanted to drink some cum this weekend? If it makes you feel any better, even if we did come it might have been hard to get away.



“Well I really wanted to drink YOUR cum this weekend! Can you blame me?

“Think I’ll have a drink since I won’t be having a Mike cocktail.”



“Here’s how I see the opener:

“We meet and you suck my cock and drink as much cum out of it as you can. Then after my cock goes soft in your mouth I want to give you a shower. You can lie back rubbing your pussy feeling completely dirty as I piss all over you. Then at the end you have to take me in your mouth and taste the last drops and feel my cock get hard while you suck me. When I’m hard I’ll lick your asshole and get it ready for my cock. Then I’ll fuck your ass nice and hard.”



“Oh wow I think I just came reading this. Where are you when I need you? It sure will be fun if we ever do manage to get together.”

22 March 2011



“I think so. I really want to have my cock to spend time in your mouth.”



“So do I, you have no idea!! I was hoping to have a visit from the Easter Bunny. I was looking forward to playing with his carrot!! Next time. In the meantime you can continue to tease the hell out of istanbul escort me since you’re so good at it.”

Then I asked the question.



“Would you have been happy if I did more in your mouth than cum this weekend?”



“Honestly, I’m not sure. I can’t believe I said that. I guess we’ll just have to get together and see where it takes us. Would it have made you happy??”



“Yes it would. Maybe a few beers would help us both to do it.”



“Maybe, can’t hurt!! So tell me what the big thrill is in all of this? I find it so intriguing.”



“Your full commitment to have my cock in your mouth while I both cum and piss blows me away. My soft pissing cock would be rock hard in your mouth before I’m done. Let’s see how it goes.

“PS – I’m f’n horny 4 your mouth.”



“Well I’m definitely committed to sucking you. As for what comes out, well I guess only time will tell. Am I freaking you out? I think I’m freaking myself out. Maybe I’m too nasty and I’ll scare you away?

“I’m horny for you too. The things I could do with that rock hard cock!”



“Hey, who’s nasty? I want to piss in your mouth? I’m wondering if I’m going to freak you out. Does the thought turn you on?”



“Freakishly, I think it might. The thought of doing anything with you turns me on. We should have done this in high school.”

I was already pretty excited about getting together with Casey and now that I knew that that she would try drinking my piss I was beside myself with anticipation. I was also flush with self-congratulatory lust. I’d just seduced a woman to drink my piss! She hadn’t done it yet, but she was going to try. Further this wasn’t someone from a dating line that I could assume certain proclivities or that I could anonymously slink away from if I fell on my face. Casey was a girl next door type, though technically speaking a girl next door from the next town type. I had a sense that I’d overcome probabilities. Not only had I found a woman to drink my piss, but the one I’d found was someone who until then hadn’t even considered such a thing. The thought of it being Casey, someone who I had known for so long and shared so many friends all added to the sense of the improbable. Despite that sense of improbability, I must say that when I put it out there I still wasn’t completely surprised when Casey agreed. After all she was at least as carried away with out plans and nightly sessions as me. And though my surprise might not have been complete, my excitement certainly was certainly total. Casey was going to try and drink my piss. The next objective would be to build her enthusiasm. Casey’s initial yes would become more determined to the point of anticipation by the time we met.

23 March 2011



“When we meet you better be thirsty, because I when I cum and piss in your mouth I don’t want you to let any go to waste.”



“Gee you really know how to sweet talk a girl!! lol

“Fuck, I wish you were here right now, cuz I’m in the mood to try just about anything. I’m feeling so horny.”



“I can’t wait. I get so hard when I think of you sucking my cock while I piss. It’ll come out hot in your mouth and I hope you can drink it.”



“I honestly don’t know but like I said if you were here right now…

“I love it that you get hard thinking about it.

“Oh what the hell, I’ll try anything twice. Getting wetter…”



“Trying is good. I think if you’re willing to try then you’ll be able to do it. And like we said, beer will help. I’ll start you off with hardly enough to fill your mouth to see how you like it.

“Do you want to feel my cock get hard in your mouth while I piss?”



“I want to experience everything there is to experience with your cock. Why is it so exciting for you to piss in my mouth? What about that turns you on?”



“I was just feeling super horny and I just ran with the idea. Regardless it does turn me on and I’ve always liked corrupting. Other than that it’s hard to say. Maybe I watch too much porn?

“Do you want me to do this to you? “



“Can one watch too much porn?!?!

“Funny, I like being corrupted. Yes, I do want you to do this to me. I would do anything to have your cock in my mouth right now. I guess I’m in one of those moods where anything goes. I’d love to do all kinds of strange things to turn you on”.



“In a way it’s good we couldn’t make it this week. Now we know that when we do get together it will be one hell of a memorable blow job.

“Right now it looks like May 24th for our visit. I might only have enough time to just slip out to fill your mouth this time around, but sometime this summer we’ll be in Montreal for a week. Then your ass and pussy will get some too.”



“Yes izmir escort it will be memorable. At least not anything I’ll ever forget.

“I look forward to your visit and our opener. I’m so horny for you now, I really need to cum.”



“When we meet I want you to ask me to piss in your mouth. If you aren’t able to drink it all and it spills from your mouth, will you enjoy the ride back home all wet with piss along with the taste of my cum and piss in your mouth? When I get back to Toronto I’ll want to read about how that felt.”



“You’re starting to freak me out, but it’s good. I like it. Don’t stop. I am rubbing and licking and thinking of your cock and it feels fucking amazing. Wish it was you I was tasting!”



“How am I freaking you out?”



“Gee, I don’t know. It could have something to do with the fact that you’ve actually got me considering any of this. Never mind considering, anticipating! I can’t imagine anyone else being able to pull this off. I’m sure if anyone had ever mentioned this to me I would have thought they were nuts, but somehow you can get away with it. Why do you think that is?”



“Sorry, I can’t help you there. When things are going my way I try not to question it.

“So are you going to ask me to piss in your mouth?”



“By the time we actually get together I’ll probably be begging you to piss in my mouth. I’m telling you if we were together right now you could do anything you want!”



“You mentioned once before about this catching you at the right time and it’s the same for me. It’s one more visit to being twenty-something that I can’t resist.

” When we meet I want you to suck my cock, make me cum and drink it. I also want to take a piss in your mouth so you can drink my urine too. I’ll try piss slowly so you’re not overwhelmed and so that you can drink it as it comes out. I’ll take my cock out of your mouth, so that I can watch my stream of piss fill you open mouth and also piss on your face and soak you hair.”



“So is this what you did in your twenties?!?!

“I can’t wait. I got wet just from reading this. Fuck you turn me on.”



“Well that was before the internet really came into play. I’ve never made such nice plans for a first date.

“I want to cum before bed, so send me one more message and tell what you’re going to do when we meet. I want to make myself cum when I read it.”



“Lol, I’ve never planned such a fascinating first date either!!

“When we meet I want you to take out your cock for me. I want to lick it very slowly at first and rub it all over my face and trace my lips with it. Then I’ll slide my lips up and down the shaft. By then you should have some pre-cum for me to lick off. I will keep teasing you with my tongue and then suddenly take the whole thing in my mouth. I will lick and suck you until I feel your hot cum in my mouth and I will drink every drop of it down. Then when you’re soft, I’ll keep working on it to make it hard again. In between, I’ll look at you and beg you to piss in my mouth. I’ll continue to lick and suck and drink until I feel you get rock hard again in my mouth.

“Are you hard now? Does it feel good? Just imagine my tongue all over you making you feel amazing and me doing anything you ask. I wish I could feel your hot cum right now.

“I’m in bed and rubbing my pussy. I want to cum with you.”

Things continued on this vane and by time May rolled around we were both beyond feverish for one another.

8 May 2011



Well the countdown is really on now until my cock is in your mouth.



“Yes it is and you have no idea how thirsty I am…”



“I’m not sure if I’ll be able to meet you on Friday or Saturday. If it’s Friday it might only be for a quickie.

“Have you got a spot pick out for us yet?”



“OK now we’re talking. I’m dying to drink your hot piss and see how turned on you get. So what do you think, will I like it? I bet you taste great!

“A spot…guess I better get on that.”



“I think that since you want to drink my piss that you’re going to like it. The more turned on you are the more likely that you’ll be able to drink it all. I’m going try and let it out in short burst to give you a chance to drink a mouthful at a time. I could piss faster, but I want to give you the best chance to drink everything. I think slow will work best. I think that I’ll also have to resist pushing my cock too deep into your throat while I’m pissing, because I don’t want you to inhale a stream. It’s OK if you choke a little at the end and I might drive my cock into your throat for the last shot of piss – but mostly I’m just going to try and relax with dick in your mouth and let you slowly drink down all my piss.”



“Wow, you’re very good! I think you’re right, slow is best. There are a few places I’d love you to drive your cock, believe me. I really can’t wait to do this. My tongue is dying to meet your cock and show it a fantastic time. I can’t wait to taste you and turn you on and feel your hot cock explode in my mouth!”

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