Raise A Glass: To The Ones Who Will

Rejection sucks. There’s really no other way to put it. It is one of those softballs to the abdomen that just leaves one with a horrible feeling, like a black hole draining life of all joy.

Setting oneself up for rejection is one thing. I can handle being turned down by a guy I actively choose to cruise. Hey, I’m just not their type. Whatever. I’m a big boy. I get it.

But that isn’t the only kind of rejection.

How about the rejection one feels when someone you fucked with once (and had a good time with) goes out of their way to ignore you? Especially when they remain on good terms (i.e. fucking terms) with acquaintances you have in common.

There’s this guy. We’ll call him Charlie, because no other name suits him (and it is, in fact, his real name). He is the sweetest guy. Dark hair. Dark, winning eyes. Charming smile. Great lips. He’s at least 5 inches shorter than me and ten years younger. His body is not worked out, but it is nice. His skin is deeply tan and there is just something so sexy about him. In part, it is his sweetness and his style of seduction; which I guess I would characterize as surprising – as in I am totally surprised when he seduces me. If he wasn’t gay, he’d be a total lady killer.

We have a bit of history between us, although I can’t recall the specifics. We hooked up on-line years ago and then disappeared from each other’s lives. The details of that tryst remain pretty vague for me. Earlier this summer, however, he hit on me at the Prairie. He was very complimentary about my body and didn’t seem to remember our previous involvement (or at least he didn’t acknowledge it). He was very charming and sweet as he sidled up beside me. He was also very direct. He intended to fuck me, which I was all for.

It was a nice fuck; one of my first this summer. It was a hot scene, getting naked and writhing away in the tall grass. His kisses were an added bonus. His dick, uncut, while average in size, performed nicely. We both got off and left each other on good terms. I asked him his name and kidded him that he indeed looked like a ‘Charlie’. He left me with a warm feeling, and I’m not just talking about the after glow that was heating my just-fucked hole.

I must admit, I do not have a good memory for people and places. I saw Charlie a few days later and wasn’t sure if it was him, or some other guy. The next time I saw Charlie, and each subsequent time, he has silently walked away from me like I was a dog that had bitten him once. He seemed wary of me and made it clear with his body language that he is not interested in me on any level. I’ve done my best to put on a brave face. I still make a point of saying ‘hello’ each time I see him, but he never stops to talk.

The other day I arrived at the Prairie and noticed a little threesome near one of my favorite sunning spots. It was Charlie, and Kyle (this guy I spoke of last week) with whom I am on good terms with, and a very tall guy named Eddie (not his real name), who is very unfriendly and rather anti-social. I’d heard through the grape vine that Eddie has a huge dick, but I have yet to see it. I doubt I ever will. I chose a spot nearby (one of my regular spots, but not my favorite) and made a point of not looking over in their direction or going over to bother them. Once I dropped off my stuff, I walked in the opposite direction to see if anyone else was around.

My friend Kyle was busy being pig roasted by Charlie and Eddie. By the time I got back, it was all over except for the huge smiles and group small talk. I sat on my blanket and made no attempt to join in their conversation. Charlie was all smiles. Charlie has a great smile. It made me sad that I no longer get to see it radiate in my direction. I felt odd about being in such close proximity to them; so again, I walked off to another corner of the Prairie. Giving people their privacy is important in my book. Respecting personal space is something that I believe earns one brownie points in the big picture. By the time I returned, Eddie and Charlie had gone their separate ways. I approached Kyle and we began to chat.

Kyle, flush with his recent activity, shared a few details about how it all came about. He had a great time and only griped that he wished it had been Eddie ramming his ass with his gigantic cock, instead of just Charlie. I was happy for him. Envious, too. I can’t help it. I hate feeling like the ugly stepsister.

I commented that Charlie and I had hooked up, but that he no longer talked to me much. I almost immediately regretted saying anything. I seem to make this mistake often. But the fact is, I’m just looking for insight and information – something I could learn from. I really would like to know why it is someone stops talking to me. It’s one of the reasons I think I seek out anonymous sexual situations – I don’t want to risk personal rejection, and in a no-strings relationship, other than being turned away at the door, there is no risk of being rejected. No, that only happens in the long run.

In moments like these I try to take comfort in one thought, or in this case, one line. It’s a line from a really intriguing film by Joel Schumacher. Joel is a frequently horrible director. His instincts are almost always over-the-top in a bad way. The film is titled Flawless, but is anything but. It stars Robert De Niro as a tough guy cop who recently suffered a stroke and Phillip Seymour Hoffman as a vocal coach / drag queen who wants to transition into becoming female. It is worth checking out, as it features interesting work by the actors, a nice story and a soundtrack by one of my all-time favorite composer/performers Bruce Roberts.

At one point during the film, De Niro’s character is down in the dumps after being rejected by a sexy dance hall hostess who used to lavish attention on him due to his status as a cop and the fact that he had money. Now, suffering from the effects of the stroke and living on a small pension, he has nothing of value to offer her and she dismisses him rather cruelly. Not that it should matter, for waiting in the wings is another dance hall girl who has long burned a torch for De Niro, though he has never paid her any attention. She is a lot less glamorous than the dance hall hostess, but is incredibly beautiful none-the-less. De Niro is whining to Phillip Seymour Hoffman’s character about how no one finds him attractive anymore, how he isn’t getting any and isn’t likely to given his current situation. That’s when the Phillip the drag queen says something to the effect that it’s not the ones who won’t that matter. It’s the ones who will.

Of course De Niro ends up in bed with the less glamorous dance hall girl. His lack of coordination doesn’t matter to her. She loves him for who is, not what he was. And later in the film, when he has recovered from the stroke, he get a chance to rebuff the advances of the dance hall hostess who had rejected him earlier. He ends up finding happiness and the tango of his dreams in the arms of the dance hall girl that would.

Which brings home the lesson that it’s not the ones who won’t that matter. It’s the ones who will.

That is the gem that keeps this movie alive in my memory. And that is the little gem that I try to comfort myself with when faced with rejection. Or when faced with situations like the one I am currently experiencing with Charlie.

A few days later I ran into Charlie at the Prairie. I called out to him and he said hello back, but kept walking. He disappeared in the shadows beneath an area lined with trees where people hook-up. After ten minutes or so I decided I would go see what was up. I knew no one else was back there. Maybe Charlie was waiting for me to follow? But, alas, that was not the case. There he sat, on a rock, eating a bag of potato chips. As soon as I caught sight of the potato chip bag I turned around and returned to my blanket in the grass. Let the man eat in peace.

I may never learn why Charlie has an issue with me. I could ask. But what if he doesn’t want to share? What if I don’t want to hear? What if there is nothing to learn? In asking, I can only come off as desperate. So I will spare myself that little bit of deprecation.

The next day, I decided that my days on the Prairie are over for now. I’ve had a hell of a summer. Fucked a lot, sucked a lot. But it’s all gotten to be a bit too high school for my taste. People are complicated. People and their sexuality? Even more so. I need some simplicity. Enough with being social. I want to return to the anonymity of the internet. I need to concentrate my efforts and energies elsewhere. I need to go find me a whole new group of the ones who will.

I need to figure out what I’m going to do now that the weather is turning colder.

So the next time you are put on in your place in that chat room, or some guy emails you back to tell you that you are not his type, or the next time you’re at a bar using all the arsenal in your little bag of tricks to line up a trick that just isn’t happening, just remember: it’s not the ones who won’t that matter. It’s the ones who will.

And you better be damn grateful that there are those who will. Because without them we’d all be sitting at home jerking our gherkins to whatever kinky little perverted posting catches our eye on Xtube. And keep in mind… that someday… there won’t be as many who will. And then one day… there won’t be any.

But until then? Perch proudly on the barstool of your choice and raise a glass to: the ones who will.

Whatever Happened to Bicycle Mary? (And Other Horror Stories)

I was at the Prairie the other day talking with a fellow outdoor sex enthusiast. Let’s call him Kyle. We were busy sharing stories about our recent sexual conquests, as well as insights into some of the various Prairie regulars. We were in the middle of discussing a certain foot fetishist when a familiar silhouette appeared on the hills’ horizon. It was a man I have privately dubbed Bicycle Mary.

There has yet to be an occasion when I have been at the Prairie and not spied Bicycle Mary pedaling his way along the various dirt trails. Bicycle Mary is at least 65 years old (and perhaps even older). He is rail thin, with weathered, tan skin, and a mop of wispy grey-white hair that falls like trails of smoke just short of his shoulders. I think he’s short, but I am not a good judge of this, because I have never seen him when he was not riding his bike or standing astride of it. He’s an odd little character, dressed in age-inappropriate, revealing running shorts that are too, too short and frequently minus a shirt, when a shirt really is quite warranted. Sagging man boobs are not pretty, especially when attached to a leathery skeleton of a man. As I have watched him wind his way through the maze of trails throughout the summer, I’ve found myself wondering what it is he gets out of being here. He is forever poking around in the shadowed corners of the field; the areas where most people go when cruising for or engaging in sexual activity. Yet, I’ve never seen anyone approach him; in fact, just the opposite seems be the case. When he draws near, guys tend to leave the area rather quickly.

Kyle physically shuddered at the sight of Bicycle Mary. “I just don’t get… that.”

I laughed and agreed that Bicycle Mary is quite a character.

After a few more snide observations had been spat out, I sighed and said, “Well, there for the grace of God. Someday we’ll all be… there.”

And by ‘there’, I meant one day we will all be elderly, unwanted, and the objects of potential cruel comments. Kyle seemed to pick up on this right away. So I asked, “What will become of us when we’re that age?”

People who spend a great deal of their free time pursuing sexual exploits are naturally concerned about and aware of the condition of their body and how it is ageing. Neither Kyle nor I are spring chickens. I think we both look good for our age. Me, due to a disciplined workout regimen, a practice of abstaining from excessive alcohol and a firm grasp of what constitutes good nutrition and good hygiene. In part, the opposite is true of Kyle. He drinks heavily and smokes. I can personally attest to the fact that his personal hygiene is good, but I have no idea what his diet might consist of, other than a steady stream of semen. Kyle is also blessed with a handsome mug, a winning smile, a masculine voice and very good social skills, none of which I believe I possess.

As Bicycle Mary disappeared into the nether regions of the field, Kyle and I paused to consider our own futures.

Kyle was the first to speak. “That’ll never be me. I’ll shoot myself first.”

And so the questions of the day are: What does a cocksucker do with the rest of their life when there are no longer willing cocks to be sucked? What happens when our holes no longer intrigue, but instead, disgust? And will my inner troll know when it’s time to retire from under the bridge?

Kyle was certain he wouldn’t be hanging out at the Prairie trolling for dick the rest of his life, but failed to offer up any concrete insight into what he might be doing instead.

I told him I thought I’d take up badminton or some such activity. Truth be told, I hate team sports and most group activities and haven’t really given the matter all that much thought.

We’re only young for so long. Gravity wins and when it does I doubt anyone will find yours truly attractive. At least, not anyone I might find attractive. I don’t want to be the object of someone’s old man fetish. The idea of that sort of relationship creeps me out. I’d rather read a book. And bottom line – that is what I hope happens to me. I hope I simply lose interest in sex. I’d rather it be gradual than sudden, so I don’t really notice it. I also hope it happens out of a natural lack of interest rather than an inability to participate or perform. Like the end of a great film I would just like my sex life to fade to black.

I shared this with Kyle. Kyle added that he thought we’d both have partners by then and be old married guys.

Not likely. I suggested getting a roommate, with privileges, but then nixed that idea because I like being and living alone. If I had a fuck buddy they would have to live somewhere else.

I’m just so glad the whole “If I’m not married by the time I’m such and such an age, you can be my back up,” came up, because I don’t see my friendship with Kyle lasting past the fall. He loves going to bars and clubs. I do not. The only thing we have in common is a love of dick – in our mouths and up our butts. So in the end (no pun intended), we would just be competition for one another. Besides, such arrangements are the stuff of bad rom-coms and stale sitcoms.

Still… the question haunts. What will become of me? Who’s gonna need me? Who’s gonna feed me? When I’m sixty-four? Seventy-four? One hundred and four?

I don’t want to be someone who is delusional, still living in their glory days – days whose passing escaped their notice. That seems as sad as it is clichéd.

I don’t want to turn into ‘Whatever Happened to Baby Jane’ or ‘Whatever Happened to Bicycle Mary?’ for that matter.

But I’m also not quite ready to retire my balls and leave the field. I still have a few good years left.

When that time comes, I hope I recognize it. I hope I accept it with dignity. I hope I have something better to do. I hope I don’t even notice.

Until then, I plan on continuing in my role as the lead in Little Whore on the Prairie, Laura Ingalls Wilder be damned.

TMI: I Don’t Want Your Number (Because You Are Just A Number)

I was hanging out at the prairie this week. Summer is on the wane and I wanted to take advantage of whatever warm weather remains. It was a beautiful day, though I was not having a lot of luck snagging dick. It seemed every time someone interesting would wander into my radar field I would also run into someone I knew. I would have to get all chatty with this person (as I had probably tricked with them which is usually why I know them), and the potential new trick would become discouraged and wander off in search of someone not so preoccupied.

So why not fuck around with the chatty people? Well, there are a couple of them I would and do. But for the most part – I never do anyone twice. I like keeping things casual. Those that I do play with on a repeat basis? They understand the rules. Sex is a casual thing. I may fool around with you today, and have no interest tomorrow. It works both ways, too. Some days they are more interested in new meat than they are in me. Unfortunately, I just lack the social skill needed to let them know when I am more interested in new meat than I am in chatting with them. Thus my dilemma. Thus the trick gets away.

However, one thing is completely understood between myself and my repeat tricks; I never give out my phone number.

This is a huge issue for some people. I, myself, do not understand the problem. In my mind, they are a casual potential or former sex partner – so where do they get off asking for my phone number; a piece of information I consider very private?

I make all sorts of excuses for why I don’t want to give out my cell phone number. They are all based on fact.

1/ I have a phone phobia.
2/ I never answer my phone.
3/ I rarely turn my phone on.
4/ I am a very private person.

But underlying all of that is one, single, undeniable fact: I don’t want to be bothered. By anyone.

In my world, phones are for emergencies only. And ordering things – like services (tow trucks, pizza, etc.). I have used my cell phone about 10 times in the last 3 years. Four of those times were to call AAA to unlock my car doors so I could retrieve my keys. Other than that? I don’t see the need for it.

I realize that if I gave out my number, I would then get more phone calls. But I don’t want them. Again - I don’t want to be bothered. This is especially true of someone who will be in my life for a less than an hour.

Casual sex is supposed to be casual. No strings attached means: I don’t want your name or your phone number. I just want your dick.

I don’t care where you work or what you do. I care about where you live, but only because I need to drive there so you can fuck me. Remember TMI, as in ‘Too Much Information’? Well there is a lot of that out there. And people should really know better. Have you ever been stalked? Once you have, you will think twice about offering up information to some trick you met in the dugout of your community ballpark at midnight on a hot and sweaty Saturday night.

And I don’t care how good the sex was, how much we enjoyed kissing, or how much of a connection we experienced… I still won’t be giving you my cell phone.

So what is proper etiquette when one is offered the phone number of someone you have no intention of ever calling? I always feel bad when this happens. I should feel flattered, but instead, I just feel perplexed and guilty. Perplexed, because I can’t muster up the courage it takes to say “No, thanks.” Guilty, because I know I have no intention of calling this man and therefore, shouldn’t get his hopes up that I might.

So, back to my day on the prairie. As I mentioned I wasn’t having any luck. I’d been there for four hours and zilch, mostly due to bad timing on my part (not able to extradite myself from conversations with past acquaintances). And then, this dude who I do play with on a regular basis shows up. I’m thinking this is good, as he is usually a sure thing. But hold the phone – he masturbated before he came and is really there only for the sun and conversation. That’s cool with me. So we chat. As we chat, this very tall, very young Viking type strides past. I had spotted him earlier in the day. He was hanging out with a group of three other people his age. They said hello to me as I walked by. Continuing on my way, I commented on what a beautiful day it was. I was almost out of earshot when I heard one of them say something to the effect that the day was not the only beautiful thing around here. I pretended not to hear that – it’s kind of a corny thing to say, and just continued on my way. In hindsight, I think it was the Viking guy that said it.

Why am I calling him the Viking guy? Because he is very tall. And sturdy and beefy. He has reddish blonde hair and a bit of a permanent scowl. He also had a little beard on his chin. In other words, he looks like a Viking.

Now since my chances with my usual fuck bud are nil, I decided to go pursue the Viking. My friend continues on with a monologue I’m not hearing as I drift off into the woods, in search of a little Valhalla. My approach is an anxious one – he is young and what if he’s a total bottom or only wants to suck me off? What if I’ve misread him and he isn’t interested in me at all? But I needn’t have worried. As I approach he has his back to me. Then he turns around and I catch glimpse of the most perfect hard-on trapped in a pair of khaki shorts that I have seen in a while. We do a little dance where we eye one another and feel each other out. Then I move in close enough to grab me a handful. He unzips and hauls out a nice thick pink one. It has that translucent skin that only the dicks of true red heads have. It is also heavily veined, which always makes for an interesting suck. I’m on my knees in a flash. Recently, I have rediscovered my love of sucking dick, as in – I don’t need a hit of poppers to enjoy it. My technique is greatly improved since abstaining from poppers and those I suck seem most appreciative of my efforts. At first, his dick is sticking out of his open fly, but soon, the khaki shorts are loosened and falling off his lightly furry ass. I cup his ass cheeks and go to town, deepthroating him for all I’m worth. On occasion I steal a look heavenward to watch the pleasure spread across the face of this formerly rather stern Viking. After a few more minutes, having altered my technique several times, my mouth is making a great sucking noise which is then joined by the joyful noise made by a Viking who is about to lose his load. With a great crescendo, our orgasmic choir hits all the high notes, and I end up with a nice throat full of cum.

The Viking fixes himself up quickly and after a few terse smiles and a couple of obligatory thank you’s, he sails away.

I return to my spot next to my fuck bud, only to discover that he has fallen asleep. Bored, I cast my sights about to see if there is anything new on the whore-rizon.

I didn’t need to wait long. An older, thin, formerly in great shape, man walks by. He stops a few yards away from me, under a group of trees that offer heavy shade. I can see him quite clearly, but wouldn’t necessarily know he was there unless I was looking for him. He drops his shorts and begins to put on a cock ring. Needless to say, my interest is peaked. I saunter over.

As I approach, he is now half hard. His body is okay, but he is older than I usually like. He is in decent shape and I figure, I’ve done worse, so what the hell. Without a word between us, I take his dick in my mouth. It is average in size, but it is hard. He comments on the job I am doing, really appreciating my technique. He keeps promising to cum. He wants to cum in my mouth. Fine with me. Then he starts playing with my ass. Well, considering that I came here with only one thing on my mind – to get fucked – I figure if this is the best the universe has to offer at this time, that I'll take it. I turn around, take a nice hit of poppers and offer up my pre-lubed hole. He grabs it and starts delivering a nice fuck. He’s not wearing a condom, but I am in an ambivalent mood about the whole safe sex thing and let him pound away. He throws an okay fuck – nothing earth shattering, but fine all the same. After a point I realize he’s not gonna cum and that I am bored. I’m not really that into him and, mid-fuck, am beginning to regret having his dick up my ass. At that moment I notice someone approaching and pull off of him. Pointing out the approaching stranger, I gather up my shorts and head back toward my towel.

He follows me. He then wants to give me his phone number. Do I have anything he can write on? I look in my bag of supplies and come up with a receipt for bottled water. He has a pen, and scribbles out his name and number and hands it to me promising to fuck the cum out of me at his place. I wordlessly accept the phone number and my sorta-fuck walks away.

By this time my fuck bud is awake. He makes a comment about how everyone could see me getting fucked. I’m a bit embarrassed; not for being such an obvious whore, but because of whom I was getting fucked by. I then ask my fuck bud what the etiquette is when receiving a phone number from someone you have no intention of calling. My fuck bud decides, suddenly, that he is a lawyer and begins to breakdown the pros and cons of various arguments and possible outcomes.

Finally, we mutually decide that if the phone number was not requested and the receiver makes no promises to call, then the receiver is not guilty of anything that will result in bad karma, because there is no spoken intent upon the receiver. This makes sense to me, but I begin to think of all the people who have given me their number and elicited promises from me that I would call. I never called. Which is my burden, I guess. I should just be frank with them, brutal even, and tell them 'no'. But that in evidently leads to the question I cannot bring myself to answer – which is “Why not?” Why not? Because I am not attracted to you. Because I do not want to come to your house. Because you are a casual fuck, not a potential partner or date. Because I don’t like making phone calls to guys who I shared an orgasm with. Because this is a no-strings transaction.

Because… I don’t want to.

Does that make me mean? Perhaps.

But, given the circumstances, why on earth would they want to give me their phone number?

Common sense says… no.

So, this entry is for Dennis. Dennis? I won’t be calling you. Why?

Because I don’t want to.

A Tale of Two Fucks: Two Guys Dickens My Ass

Sunday. I do not feel like warming up yesterday’s coffee or eating anything in my refrigerator. I decide to take my laptop over to a nearby coffee shop and steal some wi-fi. The shop is nicely laid out, the counter help relatively friendly and the wif-fi is super reliable.

I order a skim latte and settle into what is destined (as in – come this winter, when I cannot be outside trolling for tricks) to become my regular spot; near the windows, near an electrical outlet, and private enough to scope out the amateur nude shots prospective on-line tricks will send me.

I sign into my email and two of my regular gay hook-up sites. It is about 11:00 am and I am fairly certain that finding someone on-line will be a long and painful process, eating up the rest of my afternoon and possibly resulting in absolutely nothing of value – as in – no hook-up for yours truly.

I’m pleasantly surprised when I get hit on almost immediately by two separate individuals. Playing the odds, which are that neither will result in my ass getting any dick, I decide to pursue both.

Candidate #1: is this tall, thin, black-haired youth. He has a freckled-face that makes me think of a child actor who is no longer a child, but keeping his cute factor in place. On-line? Charming. Friendly. Lots of humor. He’s young. Only 28 years-old. His body is rail thin, but he looks good in his pics. He’s clothed in all his pics. His overall style strikes me as someone who listens to Fall Out Boy or My Chemical Romance. He wants me to come over to his place so he can fuck my ass. He also likes to make out and kiss. I’m all for that. Unfortunately, he has a lunch date and won’t be returning home until after 2:30 pm.

He wants my cell phone number.

As a rule, and I explain this to him, I don’t give out my cell phone number. To anyone. Fact is; I have had a cell phone for over five years. I believe in that time I may have used it 10 times – three of which were to call AAA to come help me retrieve my keys, which I locked in my car. So I am not big on cell phones. I do not give out my number. Why? I don’t want anyone calling me. Why? Because I never check messages on it and it is rarely on – so I miss a lot. Why? Because I have a phone phobia. I hate them. I don’t like talking on the phone. I hate the sound of my voice and – and this is probably at the root of my phone phobia – when on the phone I tend to get talked into doing things I don’t want to do. I can say no in person – I just haven’t mastered that on the phone.

He is kind of put off by it. After volleying emails back and forth at a good clip for over a half hour, his end suddenly goes silent. Twenty minutes later, I get an email telling me, okay, to email him and he will get it on his phone. I want to say – if you can get email on your phone – then why would you need my cell number? But I don’t. I just promise to email him at 2:30 pm, once he has gotten home from lunch and had a chance to clean up his place. That last comment is usually a red flag for me, but I let it pass. I promise to email him on time and look forward to getting together.

Candidate #2: is a tall, thin, Jamaican man that I fucked around with once before. He has a gorgeous body, beautiful skin, a beautiful face and a big, big dick. Probably 10 inches and thick. His head is shaved and he embodies none of that culture’s pot influence. The last time we fucked, he had me meet him in the lobby of his apartment building. He took me down into the basement to an empty storage locker. We went inside and he closed the door. It was pitch black inside. The only light we had came from his cell phone. It made fooling around a bit challenging, but I like a challenge. Plus, we had to be quiet – which is always a challenge for me. It was fast and furious. Lots of kissing and the inhaling of poppers. He ate my ass. I deep-throated his dick. He fucked me with a condom on, but little lube. It was one of those scenes where you leave quickly and giddily, still trying to catch your breath as you approach your car.

He wants me to come over for a repeat. This time, behind his parked SUV in the underground parking garage. But he can’t play until 4:00 pm. I’m cool with that. He lives a bit of a distance away, but nothing that I can’t get to within a half hour. I agree, thinking this will probably not pan out. Later he changes his mind and writes me that he wants to meet at 3:00 pm. By this time I have already made a date with Candidate #1 – whom I will call Emo Boy. I tell him I can’t meet then. I then tell him that I can’t be to his place until 4:30 pm, thinking this will be a deal breaker and result in him calling the whole thing off. I’m wrong. Still later, he writes me that he has changed his mind about the parking garage. Instead he wants to play in the shower in his bathroom. He wants me to put on a thong or some underwear so he can fuck me through them. Something like that. I volunteer a jock strap. He says he may have something for me to wear. He sends me his apartment number and the code I need to buzz him. We’re all set for 4:30 pm.

Feeling like the total slut I am, I decide not to count my chickens before they hatch. This could all blow up in my face. One or the other could get cold feet, find a better trick, or lose their nerve. Or… I just might pull it off and get fucked by two dicks instead of one.

So I order a piece of coffee cake and an herbal tea and wait.

2:00 pm I get an email from Emo Boy. Did you change your mind? I write back – you said to wait until 2:30. I was just following directions. He says he’s home and will jump in the shower. How soon can I get there? I tell him I would need an address to figure that out. Turns out he is about 10 minutes away. No problem.

But wait… problem.

And this is the problem with hooking up outside the home. I need to douche. Yes, I douche. I like a clean butt. I like to know that it’s clean. It gives me confidence. Not having a clean butt is like offering someone a hamburger – which looks edible, if not great – trouble is you’re not sure if the meat is fresh. I like to keep things fresh.

I widen my time window and tell him I’ll be there as soon as possible. I hit the bathroom. But not before I send a final email to My Jamaican Friend assuring him that I will be there at 4:30.

It is now 2:15 pm. I have calculated my little adventures to take place on the following schedule.

2:15-2:45 Shut off computer, pack up. Douche in bathroom. Drive to Emo Boy’s house.
2:45–3:45 Kiss, suck, and get fucked by Emo Boy. Make polite conversation, clean-up and leave.
3:45–4:15 Drive to My Jamaican Friend’s apartment complex.
4:15–4:30 Check to see if I still have a brain. Also check to see if ass is still clean and wipe down self with disinfecting wipes.
4:30–5:30 Kiss, suck and get fucked by My Jamaican Friend. Clean up, go home.

Perfect.

First, I wait in line to use one of the two unisex bathrooms available. I’m last in a line of five people. These are single units with a lock on the door. In one, there is someone who seems to be taking their time doing whatever it is they are doing (douching for a date, perhaps?). I look at the ceiling and count the bumps in the tiles. After what seems like forever, I get in the bathroom.

Someday I’ll explain my douching technique for public places. It is involved and is not always fool proof. But I do the best I can. I like to run a clean business. Once finished, I hustle my fresh-as-spring ass to my car. The lights are with me, and so is the flow of traffic. I get to Emo Boy’s place a little ahead of schedule.

Emo Boy’s neighborhood is not the greatest neighborhood. I feel intimidated and fear for the safety of my vehicle. I lock my computer and brief case, along with my billfold, in the trunk of my car. Emo Boy’s house is much nicer than the neighborhood, but still looks like it could use a bit more care. I ring the door bell.

Did I mention it is Sunday? I’m no fashion queen. Monday thru Friday I am a button-down shirt, dress pants and tie guy. On the weekends, if not going out for a special dinner – I am a t-shirt and jeans kind of guy. I don’t like fashion fads. I buy basics. In my eyes, they never age, nor do I end up looking ridiculous by trying to keep up with fashion or dressed inappropriately for my age. Emo Boy is 28. I am not. I am older. He knows this. He has assured me that he only likes older guys.

Emo Boy opens the door. His hair is moussed up in dramatic angles, like a rock star who just rolled out of bed. He’s wearing big dark glasses created by a designer of note, a white, short-sleeve shirt riffed with some Christian Audigier type pattern worked in, and hip, trendy jeans. He’s tall and super thin. He looks like a member of Tokyo Hotel.

First words out of his mouth? "Nice outfit."

I am… speechless. I have on basic dark blue jeans – no holes, no trendy anything. They are the right length and fall nicely. I have on a basic white t-shirt. Clean. Bright white. New. My hiking boots. Broken in, but still nice. Not dirty at all. And a clean baseball cap.

I explain: It’s Sunday. (Doesn’t that translate in Emo?) I originally had a sweater on, but when the day heated up, I took it off. I didn’t know I was supposed to dress up. I didn't know this was a runway challenge.

He motions me inside and immediately tells me we have to be quiet. I look around. There are numerous pairs of differently sized shoes sitting beside the front door. However, the owner’s of said shoes are not in sight. We proceed up the stairs. He opens the door of his bedroom and out streams a very large, very loud dog. Fortunately, the dog must be used to strangers and does not bite me. He is hustled back into the room and told to go to his kennel. But he doesn’t stay there. He brings me toys. I am also now afraid to leave anything on the floor, such as my clothing and shoes for fear the dog will assume they are new toys and take them back to his kennel.

The bedroom is untidy, but not bad. It is appointed with the type of furniture that you buy at any number of outlets and the overall room has a very generic feel about it. The untidiness and the dog seem to be the only indication that anyone lives in this room. It has no character. But who cares. I’m here to get fucked.

Emo Boy lies on the bed – fully clothed. And closes his eyes. I have no idea what to do. Finally I take off my shoes and join him on the bed. We kiss. It is nice. He seems to want to take his time. He is a good kisser. He also opens his eyes on occasion, but rarely. He is super relaxed. Maybe a bit too relaxed. He is wearing cologne, not enough to be gag inducing, but enough that you can tell he is covering up something. That something would be the smell of last night’s alcohol. I am thinking Emo Boy is a bit hung over.

But his breath is fine. And he kisses well. And we seem to have some connection. I relax and sink into it. Or I try to. That dog is wandering about again. Slowly we undress each other. Or rather we take turns removing a bit of our clothing. Emo Boy is not big on movement. So far everything he has done, he has done lying on his back. Underneath it all, he is wearing black jock strap like undergear. This amuses me for a bit.

I have brought with me my usual arsenal: a black plastic cock ring, a bottle of poppers, a condom and a packet of lube. He asks about the cock ring, which I do not have on, nor have I made any attempt to put it on. What about it? He wants to know why I have it. I tell him it is fun. How so? I like the way it feels. Like how? I try to explain about how it helps the blood in your dick to stay in the dick and that creates pressure which feels really good. I don’t do a very succinct job of explaining and finally just clam up and shove the cock ring to the side.

We are naked now. His body is thin. His freckled face, cute. We kiss and try a bit of frottage. I move down and suck his dick. His dick. It is probably five inches. It is thin. It is pretty. His body and pubic area is covered in dark black fur. The fur is straight and extremely soft. I realize this is the type of boy who never looks my way twice. Dark and cute and young. So I better enjoy this while I can. Sucking a smaller dick can be just as much fun as sucking a monster. In fact, more so. I don’t need poppers to handle this dick. I take my time with it and Emo Boy lies on his back with his eyes closed.

After about 10 minutes he asks me, “So, do you want me to fuck you?”

He reaches over and grabs a condom from his stash, puts it on and pours on some lube.

We kiss. I move up his body and straddle him. A bit of frottage and then I reach back and work his dick into my hole. It feels great. Like it should. Like it just found a home. I move my feet up so I am now in a couched position. Sitting on his dick. I bounce up and down. So far, I have done all the work, and I assume that the fucking will not be any different. He is making wonderful moaning sounds. He grabs my dick and begins to stroke it. After about five minutes I tell him he better stop or he will make me cum. He tells me that’s not a problem. So, another minute or so and I shoot on his furry chest. He grabs a towel and wipes it off. Then tells me to lie on my stomach. I do and he climbs on top of me and reinserts his dick. This is not my favorite position, but a lot of guys like it. I imagine it is how high school kids fuck on a sleepover. That is usually what I think about as the top grinds away. Emo Boy does not weigh a lot, so it is a little like getting fucked by a teenager. He puts on his best moves and after about seven minutes or so, he shoots, he scores.

He removes the condom and places it on the bed side table. And then we cuddle. And we talk. It is a strange conversation. I’m very upfront with my tricks. I am not looking for a boyfriend or a relationship. For some reason that is all Emo Boy wants to talk about. After reminding him that I am not looking for a relationship we talk about relationships. He got his heart broken. He likes this song by Martina McBride. He is afraid to love again. Why am I not interested in him? Why can’t he have my cell phone number? What do I mean I don’t want to be stalked? Men stop by and knock on his door in the middle of the night. He is selling his house. He is moving in with his best friend whom he will not be cuddle buddies with. On and on. Until he falls asleep. I remain a respectful time (to actually make sure he is asleep) and then quietly hit the bathroom, dress and exit. The entire time I am trying to make my getaway, the dog is following me and bringing me toys.

He is a sweet dog. Emo Boy needs to pay more attention to him. Take him for a walk.

Having made my escape from Emo Boy’s lair, I get in my car and drive away as quickly as possible. I check my time. It is going to be close. Fortunately, it takes much less time than I anticipated to arrive at My Jamaican Friend’s apartment complex.

Upon arrival, I do a bit of safety cleaning with the wet wipes and make my way to his lobby. I am right on time. I enter the code. On comes some generic sounding reggae music. I hang up and dial again. Same thing. He’s not home. I move toward the door and pause. What to do? I can’t call him. I can’t email him. He’s stood me up. Okay. That’s cool.

I am opening the door when My Jamaican Friend greets me from behind. He apologizes and asks me to come up. We go to the elevator. In the ride up he cups my ass and sticks his crotch in the crack of my butt. He is very animated. Once the doors open, he is cool and serene. Once we are in the apartment, he is all agitated and bouncy again.

The apartment. It is a mess. It is dirty. A bit cluttered. It is uncared for. It is not the worse I have seen, but clearly cleaning is not a high priority for this one. I dread seeing the bathroom. I do not have to wait long.

My Jamaican Friend is stripped bare in two seconds. I follow suit. He is very animated and I cringe a bit to think he may be on meth. But he’s not the type. Although this particular apartment set up certainly is the kind of scene one might associate with such use.

He hustles my ass into the bathroom. It, too, is not in great shape, but not the worse I have seen. The medicine cabinet opens into a three-way mirror and My Jamaican Friend is enthralled. He wants to see my ass in the mirror. He wants me to stick it out and spread it for him. He wants to lick it. He wants to spank it. He wants to soap it up and then run his very large, erect dick up and down my soapy crack. We kiss as he barks commands. I have to stay on my toes. If Emo Boy was a bit too relaxed, My Jamaican Friend is anything but.

We hop in and out of the shower. He soaps me up. He drags me over to his bed where he orders me over his knees to spank me. But he never really spanks me. He just likes the sensation of my dick rubbing on his dick while his hands cup my ass cheeks.

Back in the bathroom, he orders me to put on a pair of pants. He wants to rip a hole in them and fuck me through it. He becomes enthralled with the reflection of my ass in the pants. His hands run in and out of the pants. He searches for a scissors. No scissors. Then he searches for a knife. (A knife!!!) No knife. (Whew.) Then he searches for… a razor blade. He find an Exacto knife and tears open a small hole. He rips away at the hole. He tongues my ass through the hole. He wants to fuck me. Poppers time. He fucks me. Poppers. More fucking. In the mirror his big fat dick is riding my ass, sliding in and out. He rips the pants off me and rapes my ass some more. It is wild. There are kisses throughout. It is very animal. Suddenly he pulls out. He doesn’t want to cum yet.

It is at this moment that I realize he is not wearing a condom. Oops.

He puts on a cock ring. He wants to fuck more, but each time he puts his dick head near my hole he pulls back. He is afraid he will shoot immediately.

After a few more attempts we take a break.

I show off my ass for him. He is sitting on his couch. He tells me he is going to shoot. He wants to know that if he shoots, can he still fuck me? Well, duh. Yeah. I turn around and place my mouth at the base of his balls and begin to lick and suck. He fires off a huge load all over his chest and abs. He is not even touching himself as he cums. His cum: it glows on the surface of his delicious dark skin. Such a beautiful juxtaposition, now it is my turn to be transfixed.

In a flash, My Jamacian Friend is behind me. He enters his still rock hard, spent cock in my ass as I am still on my knees facing the couch. He wants me to cum. He pounds away at my backside urging the jizz out of me. I unload all over the front of the couch. It feels fucking fantastic.

And that is it. Game over. Very little small talk. I hit the bathroom. I decide to douche and clean up. The toilet seat is cracked, so each time I move while seated on it, the crack opens closes on my ass, pinching it. The door is closed, but I still feel uncomfortable as hell. I am trying my best to get everything done as quickly as possible. Every towel available is soaked and soapy due to our afternoon activities. I rinse off and do my best to air dry my bits and pieces. Damp and wanting to flee, I open the door and get dressed. I’m not sure where this sense of urgency is coming from. I must still be operating on My Jamaican Friend’s previous wave of energy.

In the living room, My Jamaican Friend struggles to make small talk. He is spent and very relaxed. I however, am still rushing about. We kiss. I exit and make my way to the elevator.

I climb into my car and close the door. I start the car and turn on the air conditioning. Ahhhh. Peace. Quiet. I feel myself relax. The wow factor of the most recent fuck washes over me in little waves of electricity. He is so pretty, so good looking. His body is so hot and perfect. His dick is so fucking big. Ahhhh.

As I pull away from the curve I wonder if I will ever feel the need to get fucked again.

Really?

Right. Like Monday doesn’t follow Sunday.

Get real, dude.