Cupid's Big Weekend

Calvin stands before me, naked and beaming.

"You are the man," he announces, bouncing up onto his toes and back down, up and down. His cock is bobbing at me, beckoning. But now it kind of belongs to someone else. That thought gives me a twinge in my gut, but just for a moment.

"Nah, I just do what I can to help," I modestly reply.

"Can we go again?" he asks, planting himself back down on the rug.

"How about if you and Reese do each other this time?" I suggest. "You know what they say, 'give a man an enema, and he'll get fucked once. Teach a man to give an enema, and he's fucked for life.' Or something like that. I forget how it goes, exactly."

Calvin laughs. "Maybe Aunt Emily has that cross-stitched on a doily somewhere. We'll have to look for it later."

Of all of the things I've dreamed about doing if I was ever alone with a naked man on his hands and knees, laughing until I cry was not one of them. But it seems right, somehow, completely right.

We hear the toilet flush, and Reese appears in the doorway.

"Well, that was ... different," he says, slowly.

"You okay, buddy?" asks Calvin, getting to his feet and coming to Reese's side.

"Oh, hell yeah. We doing this again?" Reese clearly found something to enjoy about the experience.

"Josh says we should do each other, kind of a hands-on application of what we've learned. You ready?"

"Fuck yeah. Let's do this thing."

"Me first!" Calvin throws himself down on all fours, legs spread wide. He lowers his forehead to the rug, reaches around behind him, and pulls his asscheeks apart. His hole, glowing with all of the attention it's been getting, twitches in the cleft, hungry.

Reese steps up. I hand him an enema bottle, and nod my head toward Calvin's waiting ass. He takes it, presses the nozzle to the pucker, and pushes it in. He smiles, like he's a caveman who's just discovered fire. He squeezes the bottle and watches the liquid flow into his best friend's ass.

"Done already?" Calvin whimpers when the bottle is empty. "We need to find larger ones somewhere."

"Dude, you're a total ho," laughs Reese. "Now get up and do me."

"With pleasure, sir." Calvin springs up and grabs the last enema out of my hand.

Reese settles onto the floor, hands and knees, and waits.

"Come on, help a brother out here," whines Calvin. Reese reaches back as Calvin had done, spreads his own ass wide open, and waits.

"Fuck, man, you are ... okay, I'll say it," he says, with a glance at me. "Reese, you are beautiful."

He leans down close to Reese's tightly buttoned ass. Instead of the enema nozzle, what Reese feels poking him is Calvin's tongue.

"Stop it! We're not done yet!" growls Reese.

"Mmmmppphhh!" is all Calvin can say in reply. To be fair, it's hard to enunciate when one's tongue is shoved completely into another person's asshole. Try it sometime!

"Okay, okay," Calvin says, regretfully, as he pulls out of Reese. "Here goes." He thrusts the nozzle home with perhaps more gusto than Reese was expecting, but he holds the bottle firmly in his friend's ass.

"Ready?" he asks.

"Go already," replies Reese.

Calvin's hand, the product of years of intense physical training in the grasping and holding of footballs (and baseballs and rugby balls...) flattens the enema bottle so rapidly I think it's going to burst. The resulting jet has to have reached Reese's throat from the inside.

"Oh, fuuuuuuuuuuck." breathes Reese, as he struggles to keep himself from collapsing.

Calvin yanks the nozzle free, and then sits back on his heels to admire his work. "That is one fine ass. I am so boning you tonight."

"You, sir, are a romantic," mutters Reese. "And now, I have some stuff to blow out my ass, if you'll excuse me."

He gets up and walks off to the toilet, leaving me alone with Calvin, who is seriously tumescent. A drop of clear pre-cum drips in a long, spidery thread from the tip of his enormous cock.

"So," Calvin begins. Am I really going to be making small talk with a naked hunk of man with a dripping dick while his lover evacuates his bowels in the next room? My fairy godmother is fucked up in the head.

"What do you think it's like to be, you know..." he trails off, suddenly demure.

"Fucked in the ass?" I cheerfully offer.

He grins. "Yeah, that's what I meant. Do you think it hurts, the first time?"

"Calvin, I don't know first-hand, but I cannot imagine that it is without at least mild discomfort, at least at first. Just look at what you are proposing to put in there," I add, gesturing toward his leaking snake.

"Yeah, but if a guy's really into it, it's probably okay, right?"

His concern for Reese, his feelings, and the structural integrity of his lower gut is touching, in its way. He really is a sweet guy, even if he lets his dick think for him most of the time. Of course, if I had a cock like that I'd let it do anything it wanted.

"You and Reese love each other. You wouldn't let anyone hurt him, would you?"

He is immediately tense, as if he has just heard paratroopers land on the roof with perverse intent. "No," he says in voice that chills me with its calm determination. He's a little scary when he does that, even when he's naked.

"Then you won't hurt him. You'll know to go slow and let him decide when it's too much."

"That's not what I meant," he begins, but at that moment Reese emerges from the toilet room. Calvin rushes past him, eager to release his own load.

"Well, that's not as bad as I thought it would be," Reese announces, somewhat jauntily. He sits, somewhat carefully, on the edge of the bathtub and takes several deep breaths.

Calvin emerges from the toilet room, grinning eagerly.

"What's next, gentlemen?"

"Ah, now that you're all clean and ready to go, let's get you into the bedroom and on to the next thing: The Talk."

"The Talk?" Calvin repeats, looking at me and then Reese. "What's The Talk?"

Reese frowns. "You know, the way you two say that it sounds like it should be capitalized. Kind of creepy."

They follow me into the bedroom, where the lube and the condoms lie in wait on the bed.

"Yes. The Talk. Before one commences anal intimacy, one must ascertain the history and past practices of the potential partner," I begin.

"Dude, now it sounds like you're reading from an instruction manual," Calvin says, his nose wrinkled in objection.

"I am. Page 36 of 'Gay Sex for Complete Beginners.'" I show them the book on the nightstand, where I've left it open to the salient section.

"So, full disclosure time. You both must first swear that you will be honest and complete in your answers."

They hold up their hands in a perverse imitation of an honor pledge--the honor is intact, I'm sure, but they are still naked and mostly boned-up while they do it. It's quite a sight.

"All right. Now, unprotected anal sex carries risks, and so you must wear a condom unless you are in an exclusive relationship."

"Josh, I'm not looking to fuck other guys," interrupts Calvin, seeming offended at the very suggestion. "I don't want any other guys. Just you," he turns to Reese. "Only you."

"Only you," replies Reese, solemnly. I feel like I've just witnessed a wedding. It's simply too sweet.

"That's great, guys, but you also have to take into account your sexual histories. Now, have either of you had unprotected sex, whether anal or vaginal?" That last word shocks them a bit, I can tell; it's almost like I've reminded them that vaginas exist, and they are troubled by that.

Reese answers right away. "No, no anal, and ... well, the other kind ... always with a condom."

Calvin nods. "Well, I've had lots of regular and actually quite a bit of anal..." I can tell Reese is taken aback by this, but Calvin continues. "Always with a condom."

"Quite a bit of anal? What does that mean?" demands Reese.

"Well, I've done a few chicks that way. You really never have?"

"Cal, you seem to have forgotten that I was pretty much wrapped up in not admitting that I was in love with you. I've had sex with exactly three women, total, and anal was the furthest from my mind, because it would have made me think of you."

Time to get our focus back. "Okay, so here are the standings. Reese: no men, no anal, vaginal always with condom. Calvin: no men, lots of pussy, and a suspicious amount of anal, always with condom. That about cover it?"

"Yep," Reese nods.

"What do you mean by a 'suspicious amount of anal'?" demands Calvin.

"I just mean that the large number of times you were up people's butts may be an indication that you were trying to work through your desire to possess the one butt you couldn't have. That's all." I smile sweetly at Calvin. Reese bursts out laughing.

"I love this guy," he manages to say through the peals of laughter. "He can turn your relentless pursuit of fuckable women into a hidden desire to fuck me. That is awesome." He presents his fist to me, and we bump. Calvin scowls.

"Whatever. So, what's the next step, chief?" Calvin is all business when it comes to pleasure.

"Well, you guys need to make the call. If you trust one another completely, I think your risk from unprotected anal sex is relatively low. At least that's what the flow chart on page 38 seems to indicate."

"Whoa. I've never done it bare," marvels Calvin. "That would be totally awesome. Are you up for it, buddy?"

Reese takes Calvin's hand in his. "I trust you with my life, Cal. And I trust you with my ass."

They kiss. Is it possible for a moment to be both romantic and profane? Because this one is definitely both.

They're still kissing. I wonder if I should slip out of here.

Still kissing. Yeah, it's time for me to go. I grab my pack, and head out to find a place to crash for the night.

"Josh, wait," calls Calvin as I step into the hallway.

"Yeah, Calvin? What is it?"

"Will you stay? I want you here. I want to be sure that this goes okay." He looks at Reese. "I want to be sure no one gets hurt."

His concern for Reese touches me once again. What can I do? And objectively, if you have the chance to watch two completely gorgeous men have sex for the first time right in front of you, would you be able to walk away? Yeah, I thought so.

"Calvin, you won't hurt Reese, I know you won't. But I'll stay anyway, if it will make you feel better."

"Thanks, man," Reese softly adds, stroking my arm gently.

I sit in the chair off to the side of the bed, and Calvin and Reese begin making out again. Immediately, they seem to forget that I am there, and I watch them as their groping and rubbing becomes more urgent. They fit together as if they were molded as one and separated at birth; here, eighteen years later, they are to be rejoined. I find myself swept away with the passion of the scene, forgetting that I am there to be, oddly, the anal sex coach who also happens to be a virgin. Strange world.

After a considerable stretch of foreplay that is leisurely and frantic by turns, I sense a moment of transition coming. They are getting ready to embark on something completely new, and both their spirits and their flesh are willing. With passion-drunk eyes and steel-hard cocks, they are ready.

"Josh," Calvin huskily whispers. "We're ready." Reese nods.

As I stand and step to the edge of the bed, Calvin rises and joins me. His eyes burn with pure sexual energy, and I hardly recognize him.Well, I recognize that slab of horse meat he uses for a cock--that's perfectly familiar. I find myself worrying that I've been too confident in Reese's ability to take that thing. I'm not sure I could. Then again, having Calvin kiss me for twenty minutes would make me consent to fucking a fire hydrant.

I turn to Reese. "Are you ready?"

He swallows. He nods. "Yes, it's what I want."

"Then do it already! Fuck me right now before I take it and shove it in myself!" Calvin shouts as he mounts the bed on all fours.

Reese looks at him, and at me, and back at him. He is speechless. I am speechless. Calvin simply wags his widespread ass back and forth, ready for the onslaught.

"Something wrong?" he asks, bouncing up and down slightly on the edge of the bed.

"No, I ... I just assumed that it would be Reese that would be ... umm..." I trail off, not sure how to say what I only now realized that I had been assuming.

"Me too," says Reese, with a voice that betrays both relief and excitement.

"Why? Because he was the one who was all heartbroken and pining? And that makes him girlie? Come on, Josh, Mr. Let's Not Care What Society Thinks! We're both men, we are in love, and we both have shiny clean asses thanks to you. Now I want my best friend to fuck me in the ass, right now, to show me that he loves me enough to bugger me into next week. Are we clear?" He again wags his ass at us, emphasizing his point. He makes a compelling argument.

"Dude, chill," Reese soothingly replies, his hands tracing delicate patterns on Calvin's lower back, and down along his powerful, open buttocks. "I want you so much it hurts. I just never knew that this is what I wanted. But it is."

He drops to his knees, wraps his arms around Calvin's hips, and pulls that lovely ass right back onto his mouth. From the sounds he makes, I can tell that he's giving Calvin's anus the same treatment he gave mine earlier, and my ass twinges a bit, jealously. The guy knows how to rim.

Remembering my role here, I grab the lube that's still on the bed, and pop the top. Reese pulls his face out of Calvin's ass crack, a huge smile shining between his spit-slicked cheeks. I squirt some lube onto my index finger, and press the tip against Calvin's asshole. He moans and rocks back, forcing my finger into his rectum. It's warm and soft in there, and Reese is a lucky man. I squirt and probe several times over until I've gotten a good amount of lube into his ass and around the outside of it. Then I squeeze a huge dollop onto Reese's burning hot prick, and work it around. He moans in response to my impromptu handjob, which I take as a compliment.

"You're ready," I pronounce.

"Josh," calls Calvin. I walk around the other side of the bed so that I can see his face.

"Yeah, Calvin? What is it?"

"Stay right here with me, okay? I want to be able to see you."

For the first time I sense a stress in his voice. I realize that all along he's been asking me about whether it would hurt, and he was asking for himself, not Reese. He's been planning on getting fucked all along. Was it just yesterday that he couldn't get past his disgust about the whole gerbil thing? Now he's preparing to have a throbbing hot cock inside him, and it's clear that he can hardly wait.

"Now, go slow, Reese, and let Calvin know when it's okay to go further. Calvin, you set the pace by pushing back when you're ready." They both nod, as if it's the most natural thing in the world to have someone give you instructions as you lose your virginity.

I walk around the other side of the bed and lay down so that Calvin and I are face-to-face, while Reese stands behind him. I can tell just by looking into his face when Reese's cockhead makes contact with his ass. His eyes open wide, and then they close with a flutter, and I feel him push back, gently at first with a little rocking motion, and then harder, more urgently. His breathing is a little shallow, his teeth are gritted, but I can tell he's in heaven as Reese's cock takes possession of his most private place. Finally, their bodies make contact, and Reese is fully inside.

"You okay, Calvin?" I ask, whispering my question against his forehead, which now glistens with sweat.

"Yeah, I'm okay. More than okay. I mean, it's a lot, like every single button is being pushed at once, but it's amazing." His eyes open, and meet mine. "Thank you," he whispers, and kisses me softly.

"Okay, Reese, you're in charge," he announces. "Make it good, because I'm coming after your ass next."

As Reese draws back slowly, I sense my presence is no longer needed. I get up from the bed (and from the wet spot that my leaking, aching prick has left there) and slip quietly out the door, pausing only to take in the sight of Reese thrusting cautiously yet deliberately into his best friend, his lover, his dream. They're going to be fine.

CHAPTER TWENTY

As I open my eyes and look about me in momentary confusion, I wonder when I am going to wake up knowing where I am. This weekend has changed so much in my life that I cannot imagine going back to the dorm tonight and sleeping in my same old bed. The bed I'm now in, which I found in the next room down the hall from the master suite, is comfortable enough, but a bit lonely after the sleeping arrangements the night before.

There's light streaming into the room. I can hear movement in the kitchen, so at least I know one of them survived the night--hopefully both. I am naked, as I have been more often than not lately, and the sheets are suspiciously damp. Did I do that on purpose, or did sleeping next door to the energetic (and occasionally quite vocal) guys result in my spewing in my sleep? Doesn't really matter, I guess.

I get up from the bed, pull on a pair of shorts, and make my way out to the kitchen. There I am greeted by a lovely sight: the two men in my life, standing at the stove, apparently trying to cook breakfast. It's not that they are cooking that makes them a lovely sight, however; it's that they are both wearing sweatshirts. And only sweatshirts. Under the waistband of the gray jersey material are two beautiful, perfectly shaped asses--Calvin's full, strong buttocks, and Reese's two tight handfuls. As I watch, Calvin shifts his weight from one side to the other, and the fluid motion of muscle and sinew is enchanting. I could watch this all day.

"Morning, gentlemen. Nice view." They turn, realize what I'm referring to, and smile in greeting. Of course, once they turn I also am treated to the sight of their relaxed but still sizeable cocks arching gracefully from under their sweatshirts. Fuck me they're beautiful. It is only once I can tear my eyes away from their cocks that I notice what they're wearing: Calvin's sweatshirt says "STATE" on it, and Reese is wearing Calvin's University sweatshirt.

"So, I see that you have reconciled your differences when it comes to college rivalry," I tease.

"Well," says Calvin," Once you buttfuck a guy--"

"And are buttfucked in return by him--" adds Reese.

"Small differences like where you go to school seem pretty silly," concludes Calvin.

"Oh, and I'm going to transfer to the University next semester," says Reese, clearly pleased with the decision. "Since I already know some people there," he smiles at me, and kisses Calvin.

"That would be awesome," I reply, meaning it with all my heart. These guys are good for me, and I want to keep them in my life.

"So what's the plan for today?" I ask, as the guys bring breakfast to the table.

"Well," says Calvin, with a wicked grin at Reese, "We could show you some new stuff we learned last night. You might want to try it out."

I look across the table at them. They are both so happy, so much in love, and, of course, so fucking gorgeous. I am happy to be a part of their lives, wherever that takes us.

"You know, I might be persuaded to try something new," I say with a wink. "If the right opportunity presented itself."

"I got your opportunity right here," growls Calvin, grabbing at his meaty crotch. He's such a romantic.

"A toast, then," I announce, holding my orange juice glass aloft. "To new friends, to old friends and new lovers, and to Aunt Emily, the sly old lesbian who saw it coming years ago."

We clink glasses, and laugh at our good fortune. Sometimes life can change in a weekend of improbable circumstances; but it can also change when we decide it must, because we have already missed too much to let any more go by.