Goes Around

d’Neronique

Three cans of Mountain Dew and four packs of Gushers later, I was out of steam. See, Corey had this friend who had this girlfriend who had this thing for social gatherings. Since I was unsuccessful trying to convince him that consuming large amounts of high-sugared items was a much better time than actually going out and doing something, to the party he would go. It was really funny in a lame sort of way, actually. Corey had to be hard pressed to even let himself be convinced by a guy who had to be hard pressed to be convinced to go by some bimbo who was hard pressed for some hard pressing.

Normally, I don’t let myself be convinced by someone who had to be convinced by someone who always had to be convinced, but I made an exception for Corey. He was fucking my dad. That made him special to me – he was like the younger, hotter and male version of my mother. Corey was also my boss, which gave me infinite opportunities to fuck around and not get in trouble at work.

One time at work, me and another co-worker – a righteous bastard named Armando – spent our entire shift trying to convince the new girl to use the Enema to wash her ass out with Dr. Pepper. The Enema was something Corey kept in the bottom drawer of one of his desks in his office, and accidentally left it out on occasion. I’m personally afraid to touch it – it had probably seen parts of my father that I hadn’t even though possible to see. Armando, however, had no fear. He was a fearless dude. And in his fearlessness, he would grab that son-of-a-bitch thing of an Enema and slam it down on the new girl’s desk, along with an unopened can of Dr. Pepper and clearly explain what he wanted of her. After a while of strictly denying any desire to feel the fizzing joy of the doctor up her ass, Armando explained that in order to be officially considered an employee in his eyes, she would at least be required to pour a frothing cup of espresso into her “spunky love hole.” Still, she refused. Not more than a week later, she quit.

But Armando and I didn’t care. We still had each other to amuse, and that was all it took. Since he was a good five years older than me, Armando had endless stories of his many past sexual experiences with all types of women. While I was no virgin, my skills were limited to one girl’s worth. It just didn’t compare. Now that we had broken up, however, Armando seemed convinced that he would be the one to tell me how things were in the real life. How pleasurable sex can be; Armando was a big fan of the anal stimulation. Both giving and receiving. But since he was the straightest guy I thought existed, I figured it was ok. To him, few things were more pleasurable than a hot chick with huge boobs sticking a well-lubed finger or two up his ass. “There’s a lot of nerves up there, Josh.” That was his motto. It seemed to me that he said it especially often, and in retrospect, I think it was because he was nervous about admitting his anal-obsession to another guy. “In the shower, I just soap up my finger, shove it inside and give myself a swirly. It feels good and it cleans it out. The chicks appreciate cleanliness.”

In my shower that night, I secretly took his technique into hand. If Armando liked it, and my dad liked it, maybe there was something really good about it, you know? My finger well soaped up, I had reached behind me and pushed it in. It felt unnatural, like a mini-poop worming its way up inside me. Needless to say, I didn’t have the temptation to do it again.

So Corey was going to be out of the office. That Armando and I had the office completely to ourselves was no real change from the norm – Corey was always in and out, no real pattern to rely on. The only real difference about today’s particular absence was that I knew he was going to, at some point during my shift, fuck my dad. And I don’t care who you are, that’s just an awkward thought.

Instead of working, Armando and brought in his pc-emulation of a bunch of sega-genesis games and was playing them half-heartedly. I leaned against the wall beside his desk.

“I tried your thing with the shower and swirly, and it was not fun. You suck.”

Armando looked at me and laughed. “You what?”

I can’t believe I had to explain myself again. I was two seconds away from blushing. There was something about the earnestness with which he spoke, however, that made telling even the weirdest things to Armando completely painless. “You know – your thing. With the soapy finger up the ass and the swirling. I tried it.”

“Oh,” It was a laughing sort of ‘oh.’ “And you didn’t like it? Huh. Wonder why – did you do it right?”

“I think it did it right.”

He closed the game he was playing and faced me. I don’t think it matters who’s talking about it or in what context, sex is always more amusing than videogames to Armando. He liked being the go-to guy. “Did you soap your finger up enough? Did you not enjoy it because of pain?”

I thought about it for a moment. There was no pain, just a strange discomfort and lingering grossness in my mind. “It didn’t hurt. It just felt like… a finger-shaped piece of shit going in my ass the wrong way.”

“Hmpf.” Armando made a face. “Next time, keep it in longer. And try to find your happy spot. It’ll feel good, I promise.”

“Wait, wait, wait! Who says I’m going to do this again?”

“You won’t regret it.” There was a pause where I just gave Armando the most disbelieving look I could muster. Armando smirked his evil mob-boss smirk. “You will do it again, Josh, and you’re going to tell me about it. Don’t make me force you.”

“What an empty threat. Like you’re actually going to know whether or not I did it. I could just lie and say I did it and you’ll never know.”

Armando’s evil face continued. “Or I could just force you to do it now.” He stood up and grabbed the top of my pants and pulled me towards him, not giving me much of a chance to react before he began to unzip my pants. Surprised, yes. But appalled, not really. Armando and I frequently slapped each other’s asses in friendly comrade-liness, and this really didn’t seem that much different.

I grabbed his hands and twisted them a in a way I knew would be uncomfortable. “Wow, Armando! I didn’t know your anal obsession extended to guys too!”

“Oh, there’s a lot of things you don’t know about me, Josh.” There was an awkward pause – awkward, but strangely not out of place. “You know how easy it would be for me to overpower you – so either you finger yourself until you like it, or I will.”

It then dawned on me that he was serious. But since it was Armando, I didn’t blush. I burrowed my brow a bit and looked at him closely. What a self righteous sex addict, trying to teach me with these methods. “Fine. But if I’m taking my pants off, so are you. I need to learn your technique… You know?”

Armando looked creepy-pleased. “Would be my pleasure, Joshua.”

Work completely forgotten, Armando and I found ourselves in the boy’s bathroom. Since it was a small office, the bathroom was meant for one person only: it included a toilet, a sink, and a medicine cabinet above the sink. Seeing our reflections in it made me realize how absolutely weird this would look to an outsider. But it was just Armando so it was ok. “You go first.”

Humility a foreign concept to Armando, his pants were gone within seconds, and his boxers trailing behind a few seconds later. Armando had told me long ago that he was uncircumsized, and now I had proof. He kept his shirt on. It was a work-shirt, all nice and button-down and all that – even though it was summer, it was long sleeved because the air conditioning in the office was always kept in nice and cool. The other employees had to wear ties, but Armando and I didn’t because the boss was fucking my dad, and Armando was the friend of the guy whose dad was fucking the boss. Special privileges.

Armando shamelessly grabbed his goods with his left had and he reached for the hand-soap on the sink with his right. “It helps if you’re already aroused,” he explained. After his finger seemed like it was soapy enough, my co-worker reached around – his left hand still massaging his cock in slow, lazy movements – and fingered touched his ass a bit, but didn’t insert it quite yet. “It’s not a wham-bam kind of operation, see. You have to romance yourself a bit. Make sure everything’s all slippery and relaxed.”

Even I had to admit what Armando was doing to himself seemed awfully erotic. His legs were spread a little more than shoulder length apart, his back turned to me in such a way that I could have a perfect view of what he was doing to his asshole. It really was no surprise that Armando got all sorts of chicks into his bed – he had a good body and all that, a quirky sort of arrogant shamelessness that seemed to make awkward situations less awkward. I sort of wondered if part of the reason he had good muscles in his ass was from all the fucking he did. “You’re getting kind of hard there, Armando.”

He nodded and agreed with me using a sound that came from somewhere deep inside his throat. “Don’t worry about it.” The official ass-probing had not yet begun, and from the looks of it, Armando still seemed unsatisfied with the level of soapiness of his ass. With a final squirt from the hand-soap dispenser, Armando let out a satisfied breath and readjusted his footing. “Alright, I’m pretty much set now. Pay attention.”

He didn’t have to tell me twice. With what seemed like exact coordination, Armando gave his dick one last pull, and his ass one more massaging gesture before his hand readjusted itself in such an angle that let it’s final destination was forbiddingly obvious. The entrance of the finger was slow, slower than I thought it would have been; Armando used his left hand to lean against the sink so that he could angle his ass in a way that allowed me a better view of his technique. I took the opportunity was studied it closely. When it seemed as though Armando was pleased with the level of deepness of his finger, he sighed loudly and when I looked up, I saw that he was looking at me through the mirror. He was obviously aroused. “You have to let yourself adjust a bit, you have to want the swirl. You have to feel that want with your finger. Understand?”

I shook my head, a little absentminded from something. “Not really.”

Armando was disappointed in my answer. So disappointed, in fact, that he quickly withdrew his invading finger. It was so quick and unexpected, my own ass clenched a bit.

“Josh, soap up your finger.”

“Huh?”

“Soap it up, you’re putting it in.”

That was a little strange, I can’t lie. I’m feeling a little uncomfortable. “But why?”

“Because you have to feel the want with your finger.”

I sighed. I guess it was ok, since it was Armando. I went to soap up my finger until Armando gave me the ok. He had some seriously soapy standards. “What now?”

“Alright,” Armando had repositioned himself again, this time leaning against the sink with his right hand, his left hand back on his penis, playing with the foreskin a bit. He was looking at me through the mirror again, watching me closely – making sure I wasn’t about to rough-house his soapy asshole. “Now slowly put your finger on my ass.” I paused a bit longer than I should have. “Josh, put your fucking finger on my fucking asshole!”

“Alright, God..” I did as commanded. I also probably did it a little faster than Armando would have liked – he twitched a bit when the contact was made.

“Way to have cold hands.”

“Whatever.” I wasn’t really paying attention to his words.

There was a silence that passed between us then, although it wasn’t really awkward. I figured Armando was just going to jerk himself off a bit before my finger and his asshole reached a common temperature. Eventually, Armando switched his hands again – his left hand was leaning against the sink, and his right hand was now free to reach behind and grab the hand that was touching his ass. His index finger was still soapy; it made me feel pleasantly weird. He looked at me through the mirror. “I don’t really trust you with my ass, so I’m just going to, you know, guide you.”

“Whatever.” I wasn’t really paying attention to my words.

Armando’s guiding hand led me to lightly circle his puckered entrance a bit. “I need to re-relax.” I didn’t respond, I was too busy watching his hand lead my hand. It wasn’t long until Armando applied certain kind of pressure to my hand that suggested that it was time to enter the ass. I obliged. Armando exhaled.

“Armando, my finger is in your ass.”

He glared at me. I realized he had probably been watching my reflection the entire time with that expression; it was kind of hot, I’m not going to lie. His hand tightened its hold on my wrist. “I know.”

“Can I move it around?”

“Slowly. In a circular motion.” He paused, still looking at me. “Josh, slowly.”

I nodded, my eyes returning to the ass. My finger looked to funny, all truncated in his ass like that. I wondered if I was feeling the want, as Armando had instructed me too. To be honest, I wasn’t entirely sure what I was feeling. The inside of his ass felt so foreign and tight to me, I almost forgot it was his ass. I began to move my finger, afraid of hurting Armando, or displeasing him. “Like this?”

“You can move it around more, if you’d like.” His hand, which was still grabbing my wrist firmly, actually began to push it in even further. It seemed incredibly slutty of him to do so; I didn’t mind. I obliged and put a bit more pressure, allowing my finger to move around a bit more liberally.

Armando moaned. His ass twitched. I stopped my finger. Armando looked at me, a little angry. “Keep going!”

I didn’t like Armando mad at me, but I also wasn’t completely comfortable with the fact that I was sexually stimulating a guy - even if it was Armando. “Now that I know I’m doing it right, when is it my turn?”

“You fucking slut.” Armando seemed more like playful-mad than genuine-mad, now. He used his guiding hand to draw my finger out slowly. When I was returned the full control of my finger, I inspected it thoroughly; although there were no unpleasant specs of brown, it did smell rather funky. Armando and I washed our hands with the same soap we had used as lube, and Armando wiped his ass with toilet paper to get the suds off.

He turned to face me, a mischievous smirk on his face. “Alright, now show me the goods, lover boy.”

I couldn’t help but notice something very obvious about Armando at the present. “You’re really hard right now, ‘Mando.”

“I told you, don’t worry about it.” Just to spite me, he stretched his foreskin over his tip a bit; it soon sprung back to its normal place. When aroused, you really couldn’t tell he was uncircumcised at all. “Less staring, more stripping. Come on.” He snapped his fingers at me.

“You fucking perv! I’m stripping, I’m stripping.” I wasn’t exactly what you’d call a shy boy. Then again, I wasn’t accustomed to stripping in front of guys with erections. I tried to keep telling myself that it was Armando and therefore, by default, ok. When my pants were gone and my boxers dropped, Armando guided me to his previous spot against the sink. He stood behind me, and had something of an evil smirk on his face as he checked out my ass. “It’s my ass, not a Philly Cheese-steak.”

Armando playfully slapped my ass. The bastard likes to harass, I swear to god. “What’s were about to do, Josh, is all about trust. I trusted your finger, now it’s your turn to trust mine. You ready?”

I was leaning with both hands against the edge of the sink. Between the evident awkwardness and generic tensioned created by stripping in front of another human, my knuckles were kind of white against the counter. “Sure, whatever. What do I do?”

“Start by relaxing a bit.” He still had his pants off. I probably would have had an easier time relaxing if his pants weren’t off. “I played with myself, remember?”

“Oh, I remember.” It might have come off as bitter, but I readjusted my weight against my left hand and let my right hand wander down to touch myself. It started off slow, but as my bashfulness left, my speed increased. “Now what?”

“Soap.” It was one word, but it was enough.

I stopped jerking myself off long enough to soap up my index finger as good as Armando had be soap it up for him. Maybe a little more – because I still remembered what the soapiness felt like. It was, after all, the same finger. While trying to maintain my stunted state of arousal, I slowly reached behind myself and lightly touched my ass with my finger.

It was fucking cold. Armando hadn’t been kidding. When I hissed, Armando laughed. What a sadistic bastard. “What comes around, Josh, what comes around.”

“Shut up, dude.” I tried to mimic what Armando had been doing earlier. I tried to slowly massage the opening, to relax it. It was no use. It felt like I was tickling it with some sort of melting ice cube. Damn air conditioning. “Armando, this isn’t working. My ass doesn’t like it, ok?”

“No, no. You’re doing it wrong. Here-” Without waiting for any sort of confirmation, Armando reached forth and just sort of grabbed my hand, completely taking control over it. He slowed it down and with some sort of magical powers, warmed it up. “Is this better?”

“A little. I mean.” I mean it was strange. Armando wasn’t touching my asshole, but he was definitely in full control of my own hand that was. I was even relaxing. What can I say, Armando has these amazing chillaxing powers. “I think I’m relaxed enough.”

“Alright, now I’m going to guide your finger in, now.” It wasn’t really a question, and even if it was, I think I’d allow it. For some reason, having Armando guide my finger into my ass felt like a completely natural way to learn something I apparently wasn’t very good at. Ass-swirlies are something I’m just not qualified for. With his hand on my wrist, he angled the entire contraption of flesh and appendages in a certain way, and began to apply the appropriate pressure.

My finger going in wasn’t all that new of a sensation. I knew what my ass felt like inside, and I knew what my finger felt like to my ass. It still felt like a little shit, only now, it was a slightly more pleasant little shit. I can’t explain it very well. “Ok, what now?”

“You’re a retard. You have to feel the want, Josh, the want!”

“Oh, just swirl it around already.”

So I did. It felt like a finger swirling in my ass. A still-rather chilled finger swirling around in my ass. The chilled factor made it a little nice, actually. It gave a distinct sensation that was just finger-in-asslike. Armando, without warning, pushed my finger in further, and started to force my hand around in a swirly-like manner.

I was a little surprised. “Whoa, there, Mando. Give a guy a warning.”

“Oh, take it.” I suddenly have a strange thought, wondering if Armando was still aroused. I tried not to linger on it. Armando wasn’t gay, I wasn’t guy. This was just… ass-lessons. “Feel anything good yet?”

“It doesn’t feel bad. Just not very, you know…” I kind of trailed off because I kind of did feel something. It was hard to tell, really. Like, my balls felt heavier, like they did when they were aroused or stimulated, and there was definitely a sort of intriguing feeling now and then in my ass. “Well, I don’t know.”

I could see Armando’s reflection smirk in the medicine cabinet mirror in front of me. What does that mean? Once again without warning, Armando shifted the angle of his control and began to change the very nature of the swirlies. In fact, I don’t think they counted as swirlies. They were more like thrusts. Yeah, this is kind of gay.

“Oh,” Was all I really had to say about it. Yeah, that’s more evident, right there. “How interesting.”

“Only interesting?” He sounded disappointed. I say ‘sounded’ because I wasn’t really watching him. I’d closed my eyes more or less, and had begun to lazily hang it downwards. I was concentrating on that somewhat foreignly goodness becoming more evident in my ass.

I was super surprised when I felt my ass unpleasantly stretch for another finger. One of Armando’s fingers. I snapped my head up to look at him through the mirror. “Armando! The fuck?!”

He didn’t have to answer me, however, and he knew that. I was kind of otherwise amused with the addition of his finger. It was the strangest thing in the world, to have his hand cover mine as both our index fingers plunged into my ass with an increasing force. The increasing force was must appreciated, because what had started as in intriguing sensation in my ass had somewhat evolved into a needy sort of ranging pleasure. It was still my finger, but fuck, I didn’t have any control over it, which made it needier.

“Ok, now what do you feel?” He sounded smug, even in my aroused haze. What a jackass. He’s going to hang this over my head forever, I’m never going to live it down. When I don’t answer for a few seconds, he gives me a few extra hard thrusts and something grunt-like definitely comes out of me.

“Q-quite nice.” I look at myself in my the mirror and I hardly recognize myself. My face is flushed, my eyes a little half-lidded, one arm balancing on the counter top, the other arm reaching behind me and thrusting in and out of me, the force from Armando’s forceful thrusts kind of making my entire body shift around. Oh god, I’ll never look my dad or Corey in the eyes again, not after this. “I’m so… just wow, Mando.”

He was silent for a couple of seconds, just doing his thing and serving my ass a righteous dose of finger fucking. Only two fingers, but wow, I think that’s enough. My ass thinks it’s enough. I’m good for now. “Hey Josh, you want to cum?”

Well, that’s a question. I’d love to orgasm. That would just be awfully slutty of me. “Err... okay, yeah.” I’m a pushover. He was offering. Not my fault.

My confirmation in place, Armando sort of reaches around me and starts to jerk me off. Seriously. The elbow of the arm supporting my wait nearly bends and collapses in my aroused surprise. Armando’s all around me now. His hand on my cock, in my ass, and the feeling of another person completely makes me realize that I’m not masturbating. I’m getting closer to orgasm with every thrust and every pump, however, so the thought doesn’t bother me. I start to grunt more, and eventually, my elbow does give out and I’m just sort of leaning there, Armando pumping his and my finger all around and deep into my ass in a way that just feels so good, my workmate’s hand giving me a handjob like its all he practices at home, and my face is all red and sweaty, lolling around on my arm.

I bite my own arm as I orgasm. It’s the weirdest thing I’ve ever done, I think. I’m referring to the orgasming all over Armando’s hand, not the biting on the arm bit. It’s also so awkward. I can feel my ass all spazzing out on itself, and it’s just so weird because I know Armando is feeling the exactly same thing.

As soon as I’m done, I laugh. “Oh GOD. Get your finger out of my ass, Armando.”

He obliges and we laugh together as we wash off our fingers. Armando has to clean up my semen from his hand, and I spend the extra time wiping down my cock and the front of the sink where I unloaded most of my jizz. “Ok,” I finally admit to him when we’re mostly done cleaning up. “I like the swirly. I’m a slut for the swirly.”

He looks like he owns the world. “Serves you right for ever doubting my sexual expertise.”

It’s almost like we’re intentionally ignoring the fact he just brought me to orgasm, even though we’re not. Armando is just that way – making everything awkward seem unawkward. Handjobs on payroll? Bring it. It’s ok, since its Armando.

AN: Maybe it’s just the gay talking, but fuck you guys… mutual straight-guy amateur anal-exploration is so hot.