“How do they do it?” Tom asks me.
“What are you talking about?”
“How can gay guys have anal sex? I just don’t get it.”
“Well, just because you’re not into it doesn’t make it your business.”
I’m in Tom’s dorm room just hanging out, just a week into our senior year. He is a lot of fun to be around, a mile-a-minute talker with a great sense of humor, but he is more conventional (some would say conformist) than most of my friends.
Unsurprisingly, from the posters of fighter planes on his dorm room walls, Tom is from a military family, and from the sound of it, a pretty restrictive one. What qualifies as a rebellious streak in him has been letting his hair grow five inches long and getting drunk on weekends. In other conversations, he proudly talks about being “tolerant” of gay people, but he always adds the very conventional “as long as they don’t hit on me” qualifier, very clearly prescribing the limit of this alleged tolerance.
Tom is the last friend I would want to know that I am Bisexual. I suspect that in his worldview, being Bi might even be “worse” than being gay. People with a black-and-white perspective don’t appreciate it when shades of gray are suggested.
“That’s not what I mean,” Tom objects. “I’m not judging them as long as they don’t make a move on me.” There’s that qualifier again. “I’m asking about the mechanics of it. How can they do it, physically? How can you get something that big up your ass? I just don’t see how it would fit.”
Well, I sure know the answer to that, but I’d best be careful in revealing how I know. A few months ago, a gay friend gently introduced me to backdoor pleasure, as described in my “Thanksgiving Stuffing” story earlier in this series, and my ass has been rather welcoming since then. I take a mental count and realize I’ve had three gay cocks and two Bi cocks in me. Wait, five, really? Am I turning into an anal slut? Is buttfucking contagious? I don’t know, but it is addictive.
As I ponder these experiences, realizing I cannot reveal any of them to Tom, I can only come up with, “Well, think of what comes out of there? Isn’t it sometimes as big as a dick?”
“Well, maybe some dicks.” With a grin, he adds, “But not as big as MY dick.”
“Pffft! I don’t know how big your dick is. I’m talking about dicks generally.”
“Oh, are you talking about dicks generally? Perv,” he jokes, punching me in the shoulder. “Anyway, still seems like it would really hurt.”
“C’mon, Tom. You see guys doing women in the ass in porn all the time! And even little petite chicks seem to handle it. How is a guy’s ass any different?” He shrugs. “Other than hairier?” We both laugh. “And a few inches from balls?” More laughter.
“Yeah, I guess so.”
There is a pause in the conversation.
“You really think it doesn’t hurt?” he ventures.
“I dunno,” I lie. “Maybe it hurts a little bit at first, but obviously they enjoy it once they get going, so the pleasure must outweigh the pain.” Oh, does it ever!
“But do you really know? I mean, have you fucked a chick in the ass? If you have, spill the beans!” Funny, it doesn’t even occur to him to ask if I’ve been fucked in the ass.
“Actually, I did. Once.” Another thing I’m not going to tell him is that it was just three months ago (as described in my “Sloe Ride” story). She was insanely fun, but she had taken one of those pledges (probably due to a religious background, though I didn’t ask) not to have intercourse before marriage. Luckily, her asshole turned out to be a loophole in the pledge. To protect the woman in question, whom Tom knows, I make up a story about doing a different girl up the bum.
“So she thought it felt good?”
“She loved it. Damn, you just won’t let go of this, will you?” I taunt, laughing lightly. “I guess you’ll have to try it sometime and find out for yourself.”
I sincerely mean that as a joke. I haven’t considered Tom a potential candidate for sex. Not only do I think he would not be interested, but given his general macho vibe, I don’t think I would be interested in doing him, either. His attitude towards gayness seems a bit of a red flag, and I’ve already had a .. uh, cautionary experience in the past with a guy who got Cold Cock after I made him cum. Not that I would be absolutely opposed to doing something with Tom, especially if he has a huge dick as claimed, but I would need to know he really, really wants it. I don’t want things going south as soon as he stops jizzing.
I figured my last comment would shut him up on this topic. But sometimes I forget how hard it is to shut Tom up. After a minute, he shoots me an anxious look and says, “Look, swear yourself to secrecy …”
I make the lip-zipping gesture in response. Even if I’m not ready to do something with him, I am curious as hell about where he is going with this.
With a sly grin, he follows up, “Listen, Joe Barnes, you already know it feels really good to do someone in the ass.”
I nod. Take your time, Joe. Give him the time he needs to get to wherever he wants to take this.
“Wanna have that feeling again?”
I shrug, still not 100% sure if he is serious, and even less sure that I should trust him.
“So, is it like the tightest pussy you’ve ever been in?”
“Yes, it is,” I reply, fairly deadpan. Maybe I’ll fuck him if he wants, but he’s going to have to show me he really, really wants it.
“I know we’re not gay,” he continues. “I love women, but I wonder what it feels like.”
I’m not sure whether he’s asking to bottom or top. “If your dick is as big as you say, I sure as hell don’t want that thing in my ass.”
“No, no, no, I’m not interested in that. What I mean is … well, how big’s your cock?”
No sense puffing myself up here. “Uh … about average, from what I hear.”
“Good, good. See, you could help me find out right now. As long as you promise never to tell anyone.”
“Oh, believe me,” I assure him, “I promise. Are you really sure you want to do this?”
“Yeah, Joe, I haven’t wanted anything so much in a long time. But it’s just a science experiment. Don’t worry, I won’t go all gay on you.”
Too bad.
Before I can even react to that, he’s standing in front of me with his pants down and a tube of lube in his outstretched hand. Has he been planning this?
All right, we’re doing this. For “science.” He is facing away from me, so I can see his bare ass but not his member. I bet he is as hard as a rock, but doesn’t want me to see his state. The idea of “turning” a guy like this – not making him gay, not even making him think he’s Bi in his own head, but confirming that he’s at least a little Bi in my head – has my own cock straining.
“Go ahead and stick it in.”
“I don’t think you want me to just stick it in. Then it will hurt for sure,” I say as I pull down my pants and underwear. “Let’s work our way up to that.”
And with that, I lube up a middle finger and ease it into his hole. He lets out a low moan. I gently move it in and out, wiggling it inside to see if I can tease his prostate.
He is clearly enjoying the manhole massage as I change the angle around to loosen him more, and after a couple of minutes, I gingerly slip a second finger in. He is moaning deeply now.
I withdraw my fingers, press my prickpoint against his aperture, and ask, “You ready for the real thing?”
“Oh Jesus, that’s your cockhead back there, isn’t it?” Taking a deep breath, he utters, “Yeah, let’s do this.”
I quickly slip a condom over my dong, squirt on some extra lube, and push it in just very slightly. He starts pushing back. To keep it from going in too fast, I put my hand in the space between us to hold us apart.
“Just take your time and get used to the pressure,” I direct. “I know it sounds weird, but just relax back there like you’re going to the bathroom. I’m not going to force my way inside you. Once you relax enough, I’ll start to slide in kind of automatically.”
“Feels ok so far,” he replied.
Slowly, just a few millimeters at a time, I slip in deeper, until the resistance decreases and I am sure my glans is past the gate. “Still okay?” I asked.
“Yeah,” he stammers. “It feels really full, but it doesn’t hurt much. Not so bad.”
I remove my hand from between us and start pushing myself the rest of the way in. “I’m all the way in, man.”
“Oh fuuh-uuuhhh-uuuhhh-uuck,” he moans in one long, obscene utterance. “How can having that inside me feel so fucking good! You’re right, the fucking pleasure is way bigger than the pain!”
Feels pretty good for me too. Hot and tight, as with my previous anal encounters. Loose deeper inside, with his tight ring squeezing up and down my length. I grab his hips and start pumping in and out, slowly and gently, but making sure to bottom out with each stroke.
After a few iterations, I stop, buried deeply, ask “How’s this feel?” and reach around underneath to roll our balls together, which makes him gasp. “Fuck! Unbelievable!” Feels pretty fucking unbelievable from my perspective too.
Then I ask, “This okay?” as I move my hand from his balls to his cock.
“Yes. Oh God, please,” he replies.
He wasn’t kidding about the size of his dick earlier: I can’t see it, but just by the feel of it I can tell it’s bigger than average. I really, really, really would like to get it in my mouth. And probably not in my ass. I hope he won’t ask to reciprocate on the assfucking. He is thick.
I stroke his meatpost slowly as I fuck him, sometimes working the foreskin back and forth, and sometimes just tracing my fingers from his balls up along its length and over the glans.
He is oozing a little glob of cum down the shaft, indicating that I’ve at least brushed his prostate in the process. I take it in my fingers and lick it, relishing the taste.
“Hey, are you gonna cum in me?” he asks, panting.
“Do you want me to?”
“Oh fuck yeah. You know you’ve always wanted this straight ass,” he teases. Calling himself straight, while I’m doing the gayest possible thing to him, gets him off? No problem, because it’s getting me off too.
“I dunno about before,” I reply enthusiastically, “but your hot straight ass feels pretty good right now.”
“Then give it to me! Yeah, my ass is so hot even the straight guys want it!” Hopefully, having him see things that way will help avoid any post-cum regrets. I make a mental note that I need to keep him thinking I’m straight, too.
We fuck silently (except for squishing and slapping sounds) for a couple more minutes, while I continue my slow and steady reach-around action on his other side. The pressure starts to build in me.
“You gonna cum, already? C’mon, fill this straight ass of mine.”
I tense up and fill the condom, careful not to kiss the back of his neck or otherwise express affection as I normally would, quietly withdrawing as I soften.
Since he isn’t done, I have him lie back so I can finish him off. And what a massive slab of pork he has. I’ve had contact with a longer cock, and thick ones that weren’t as long as his, but never one that was so just plain BIG.
“You gonna suck it?”
Hmm, seeing his friend kneeling in front of his hard cock could possibly turn him off, I suppose … or on. Better check in. “You want me to suck it?”
“Oh God, please. See, even straight guys want this big fucker.”
Wanting to scream, “I’m Bisexual, motherfucker, not straight!” I stifle the words even as I open my mouth for other reasons. He lays his head back and closes his eyes while I set to work. First, I lick off the rest of the cum I’ve prostate-milked out of him, which is kind of a nice bonus to have at the beginning of a blowjob. I suck in as much as I can. He gasps, taking in a sharp breath and then moaning, lifting his hips a bit in response.
I slip a finger back into his lubed-and-loosened rear entrance while bobbing steadily up and down on his thick rod. I’d gladly suck on that thing for an hour, but between my sucking and fingerfucking he only lasts another minute, filling my mouth with a very satisfying helping of man-milk. I gulp each burst eagerly.
He said, “Oh fuck, yeah,” lying back on the couch with his eyes closed, as I gird myself for whatever his mental state will be when they open. I stand up and start getting dressed in case he loses it.
He gets up and starts putting his clothes back on, too, grinning. That’s a good sign. “Told you that you wanted my ass,” he says.
“And now you know the answer to your question,” I reply.
“I’d call that a successful experiment.” He places his hand on my shoulder and adds, “Uh, thanks for what you did there at the end, too. You did a really good job. I wouldn’t have made you swallow, but … uh, thanks for going above and beyond the call of duty.”
“No problem. Just helping a buddy out.” Our eyes meet for just a moment, and something passes between us. There is a new understanding. I know he wouldn’t have tolerated one increment further than what we have done. And going forward, he will not want anything less.
We go back to our beers and the TV, resuming regular guy banter as if nothing unusual happened. There is no weirdness whatsoever between us.
A couple of days later, I’m at his place again, watching TV and drinking beers, and nothing happens. Maybe it was a one-time deal, which is not a bad deal. He got his ass filled and a good blowjob from me, I got a mouthful of cum, and pumped a load of my own into him.
The following week, while we are just hanging out again in his room, he gets up for what I think is another beer … and returns with the lube tube and a grin on his face.
I nod, no words spoken, and we strip. He lies back on his bed, his magnificent prick up in the air, and lifts his legs.
This time, I don’t wait to get a taste of his delicious sausage. I lick up and down his oversized slab of meat for a minute, then lick his balls and across his perineum. I’m not bold enough to make continuous eye contact, but unlike last week, I dare to look up at him a few times. He’s staring back.
Fortunately, he has clearly just showered and is pretty clean. Evidently, this encounter is premeditated, too. I lick around the hole, again looking directly into his amazed, wide eyes, and even pry his cheeks apart so I can probe his butthole with my tongue a bit to loosen it up. I stand up, slipping on a condom, and slowly and carefully entering his ready opening.
Although we are facing each other, I figure he is too straight-laced to have me leaning over him, let alone kissing. I figure I’ve pushed the envelope just enough by eating his ass, so I remain standing at the end of the bed while I pound him. For that matter, he again seems disinterested in my own dick (or the rest of my body) other than having it fill his ass.
As before, I come first, then pull out and suck him off. It lasts longer this time, since I didn’t stroke him during the fuck. I savor every second of him in my mouth. Especially the moment that giant rod swells even larger and feeds me his dollops of sweet cream.
“Thanks, man,” he breathes as he comes down. These are the first words (other than an occasional grunt of “fuuuck” from either of us) that have been spoken during the entire encounter.
I don’t know it yet, but in two more days, I will meet my next girlfriend, Daphne. That might put an end to what Tom and I have been doing.
Or …. will it?
