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
01:25
Casey
"Describe your cock for me."
01:31
Mike
"Right now 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."
01:37
Casey
"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?"
01:43
Mike
"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."
01:48
Casey
"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."
01:51
Mike
"I'm getting so close."
"What about you?"
01:53
Casey
"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: )."
01:58
Mike
"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.
02:04
Casey
"Me too and I'm licking the juice off my fingers. I wish I could taste your cum too."
02:08
Mike
"Nice! I can't wait to see you do just that.
"Now I've got to get 3hrs sleep."
02:11
Casey
"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
13:36
Mike
"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."
15:27
Casey
"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."
16:49
Mike
"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.
17:24
Casey
"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."
23:49
Mike
"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."
