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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.


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.


Right. Like Monday doesn’t follow Sunday.

Get real, dude.

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