Jack – Grindr Fantasies

Threesome at the Hotel

I’m waiting in the tiny lobby of the Pantages hotel in downtown Toronto. Unlike the Sheraton, the elevators here require a keycard to work, so this makes arranging a threesome a little more interesting. I wonder who will arrive first?

A young guy, Eric, messaged me in University Town yesterday morning. When I told him I’d actually be in Toronto for the week, he enthusiastically told me that’s where he was from. I had already made plans for the first night of my trip, but they quickly changed to a threesome.

At 6 pm, I see him walk in the door and I make eye contact. The 20 year old had warned me twice that he was stocky. When I reassured him that it was cool, he sent a terribly lit bathroom photo with love handles spilling over his tight underwear. Fine! I was prepared for anything. It’s hard enough to get three people to agree to meet over Grindr, so you can’t be choosy.

In person, though, he looked like a different guy. He is strong and trim. With some confidence, and a new photo, he could do well.

“Hey,” he says, shaking hands with me before he sits down on the chair facing me.

“Sorry we couldn’t meet earlier,” I told him, “I went out to dinner with a friend.” During dinner, he had messaged me, pleading to meet earlier, but since I was out, I had to tell him no.

“It’s OK,” he says, looking slightly pained as leans back in the chair, and presses his hand against his bladder.

“We just have to wait for Jack now… Actually, I think that’s him.” It has been 13 months since I’d seen Jack’s face, but I instantly knew him. Last July, I was over at his apartment for my first threesome. After his wedding, however, he had given up playing around. Still, he sometimes pops up on Grindr, and quickly agreed to meet in Toronto. The threesome was his idea. Jack is incredibly fit. His dark shirt covers his perfect V-shaped frame.

Back in my room, the air is musty and hot. I only had time to throw my bag down when I arrived this afternoon. Jack tracks down the thermostat and turns it on for us.

“I think Eric has something he’d like to do first… desperately.” I say, winking.

“Yes,” he exclaims. We quickly get out of our clothes on the way to the bathroom, except Eric keeps his shirt on. He stands in front of the shower, holding his cock.

I’m on my knees, and Jack stands in the doorway, watching with curiousity. But with Jack nude now, we are both transfixed by his perfectly toned body. Apparently, volleyball can do wonders for your physique.

“I might have to go too,” he says.

“Hmmm… Shall we make Eric wait?” I say, and here our young friend gasp.

“Nah, that’s too cruel. Go ahead”

I turn to face Eric, and very slowly move toward his flaccid penis. He pulls back the foreskin a little. I wrap my mouth around it, and he lets out a sigh as he relaxes. Too quickly, the flood is unleashed. I can’t swallow fast enough, and some spills out and down my chin as I close my mouth. Last night, Eric had bragged that he would have about one litre for me. As I gulp down each mouthful, I feel my belly quickly filling, and I wonder if I’m going to have to stop. But I can’t stop because then I’d be drenched. Instead I have to keep gulping it down as quickly as he can piss it out. When he is finally done, I suck the last few drops straight out of his dick.

I turn to Jack who’s been watching with curiosity.

“Well now it’s too late. I’m hard,” he says.

We laugh and stare at his dick, sticking straight out at me. I can’t resist and plunge my mouth over it. He gasps and holds my head as I start to blow him. I’m in candyland; on my knees in front of two dicks.

“Shall we move to the bed?” Eric asks when I finally let go to breathe.

The two men lie back on my fresh white hotel sheets. I reach under Jack’s thighs, pull myself up to him and go down on balls and cock. He gasps as I take him into my throat.

“Wow you’re good at deep throat now,” he exclaims appreciatively.

I’m excited by the praise and suck on him with more gusto. But I remember all those months ago he came very quickly, and by the way he is bucking his hips up, history might repeat, so I have to back off.

You taught me how,” I tell him. “By force, as I recall!”

I will never let him forget that.

Eric has been watching patiently. I look into his eyes and start to work on him again. His cock is slippery with precum. He moans appreciatively, and I feel the underside of his dick hardening.

I’m kneeling on the floor at the foot of the bed, and I feel Jack grabs my cock and starts to jerk it. Then I feel the hotness of his body behind me, and something warm and hard pressing against my butt crack. Jack is lightly humping my butt now, It feels so arousing. I have never let anyone inside, but just the feeling of him sliding further between my cheeks as he pleasures himself, while I suck on Eric’s penis, makes me feel like a whore. It is awesome.

Eric is enjoying my enthusiasm too. He starts to thrust up into my face, moaning.

“Oh fuck! I’m gonna cum,” he gasps. Then he holds his breath and plants his large hands on the back of my head, holding me in place, while he takes over the thrusting. I am so turned on I am high. I can’t wait to taste his load. He thrusts faster now, still holding his breath.

Finally, he gives a sexy grunt of release, and jabs himself against my throat, holding me there. I feel his cum forcing its way out and down my throat. Immediately I know there is going to be a lot of it. I feel like I’m about to choke, but thankfully he relaxes his grip on me and I’m able to back away slightly. With each pulse he squirts out a wave of cum and it fills my mouth. As the pulses die down, I suck him as long as I can, until he starts to soften, and then carefully pull back. I taste the huge wad of his jizz in my mouth, roll it around my tongue, and then swallow.

Eric sighs and collapses into the bed, spent.

I turn to Jack, and he is already laying beside Eric. He presses his cock out toward me. A clear drop of precum sits on his slit. I lap it up, and then start to suck on him, moving my lips back and forth over his sensitive head with reckless abandon.

“Oh yes!” gasps Jack and when I look up I see that Eric’s mouth is clamped over Jack’s nipple, and he’s running his hands over Jack’s perfect abs.

Jack moans as he experiences the pleasures of two mouths on him at once. His legs, which are hanging off the side of the bed, shoot up. A few seconds later, his cock pulses and the taste of sperm again floods my mouth.

As I suck him clean, I think that I really have to get more guys next time.

Jack reaches for my cock, so I get up onto the bed. Unfortunately, hand jobs rarely work for me, so I lay down with them and take over. As I stroke, their hands are everywhere, playing with my nipples, and my balls. A moment later, I lift my ass off the bed and shoot into the air. I feel some land on my face and chest, and more on my abdomen. I keep going.

“Wow, that is really a lot,” remarks Jack.

“It is indeed,” agrees Eric.

I look down at the puddle and grin proudly.

That was the first night.

Last Man To Cum

“And how about you, Peter? As I recall you were chatting online before with… other men. Is that still going on?” The marriage counsellor looks at me over her grandmotherly glasses.

Sitting on the couch, I clutch my wife’s hand. “Oh no,” I chuckle. “Just Facebook now.”

“And what have you learned about yourself? I mean, besides–”

That I’m bisexual?

I smile at her, being sure to crinkle my eyes a little to make it look natural. “Maybe I need to reconnect with some friends,” I say. I rehearsed this in a mirror. “Working from home, I don’t have any co-workers and it gets lonely sometimes.”

My wife chimes in, “Unless you count three screaming kids.” We laugh and I hug her close.

Cheater! My mind screams. Liar! How can you say you love her? I bite my lower lip and maintain eye contact. I do love her. I feel out of control. It started as a lifetime of curiosity, an it was supposed to end with an I’ll-try-anything band aid fix for my depression. Now I can’t stop. The best I can manage is to protect my family and the woman I love from my dark secret. I feel completely alone.

“Let me tell you something,“ says the counsellor, putting her notepad in her lap. “You two are just about the most open minded couple I’ve ever seen, all considered. You’ve come a long way since February. I can really see the closeness you have together, and it always brightens my day when you come in. If you’d like, I can see Jennifer alone next time. Next Thursday at 3?”

I’m not surprised. Even with everything going on, I have been feeling better lately. With the help of a mild antidepressant, I can dip into a well of happiness whenever I smile.

My wife, on the other hand, has been stuck at home for a year with two preschoolers and a baby. She’s anxious, so tightly-wound that everything sets her off. A popcorn maker left on the counter from our “date night” instils, without warning, a seething rage the next day. After the kids have climbed all over her, she doesn’t want to be touched. She needs a break. After 5pm, I take care of them and give her some time off, every day. There is no time for beer with friends, and there won’t be for a very long time.

At least I don’t have to visit the marriage counsellor next week.

That’s when my first gay threesome is scheduled.

“I’m bringing together two previous characters,” I tell one Grindr buddy, “The 5-minute kid and the engaged guy.” Adam and Jack. It’s surreal. I feel like a puppet-master.

“So jealous ;),” he writes back. “Lemme know when it’s on your blog.”

It’s exciting – the 20yo Adam is sexually charged. And I loved chatting about married life with Jack. I wouldn’t mind getting together for coffee with him as his wedding approaches.

Hookups are a lot like public speaking. After the first few awkward attempts, you become natural and relaxed. When the day comes, I’m casual. I get a lot of work done in the morning.

By noon, it turns out that Adam has to work until 4 and can’t meet at 3 as promised. And he needs a ride.

I drive down to where he works and he squeezes into my tiny car. The young Caucasian has slick black hair and he’s built like a football player. He tries to push his seat back, but it’s blocked by the baby seat behind it.

As we drive, he’s a ball of energy.

“My mom and sister were gone this weekend,” he tells me, “So I drove to Timberville and had sex!” He holds up his phone, sporting a young man in a black shirt. “It was this dude. Did you ever talk to him?”

Being smaller than University Town, Timberville’s population is starving for sex. Late at night, 18 year-olds often contact me, but there are easier pickings locally.

“Just a sec,” he says, and Snapchats a photo of himself. “Okay, who was the waiter? Was it him?” He scrolls through an ensemble of baseball-cap wearing dudes and I say no to each one. “Come on, I wanna know! Wait, Bi guy is saying we have to hurry, his room-mate’s coming back at 5.”

It’s 4:30 when we pull up next to the apartment building. The asian man paces anxiously in the lobby.

We quickly pile into the elevator and he tells us our cover story. “If my roommate comes back, you guys are my beach volleyball buddies. Got it?”

“Yeah, sure!”

“Just nod and go with it.”

We go into his spartan bedroom and quickly strip. We’re on the bed. Jack lays back and Adam engulfs he penis. Moments later I jump on him, straddle his face, and shove into his mouth.

“Oh gahg gyeah,” Jack manages to utter, but his mouth is full of my penis. He sucks on it eagerly. I can’t believe I’m in a fucking threesome. Jack’s having a lot of fun, it seems, as his familiar moans get more urgent.

“Ugh kay guys I’m gonna cum,” he sputters. I pull out to watch. Adam holds Jack’s penis up and a moment later it erupts powerfully. Jack shoots himself in the face and all down his chest, then lays there gasping, chest heaving.

It looks delicious. I dive in and get what I can from his leaking penis, then lap his warm sperm off of his his toned abs.

Adam watches and slowly moves his foreskin up and down his thick cock. I have an idea.

“Hey guys, last time I was here, I choked on Jack’s cock.”

“Yeah I read that, I’m sorry.”

“And now,” I grin evilly, “I think it’s time for a little payback.”

“What?! ”Jack’s eyes widen in shock.

“I want you to suck his cock,” I order. “And I want you to make him gag on it!”

They both stare at me, Jack in growing horror, and Adam with a sly grin. The kid spreads his legs and lets his thick penis flop down under its own massive weight.

“Okay, whatever, I’m game.” says Jack, and rolls over to his task.

Jack bobs his head up and down, and Adam sits back and enjoys it.

“That’s not good enough,” I tell them. I can still remember nearly vomiting as Jack obliviously plunged down my throat with his full bodyweight last week. “Come on, make him gag!” I command. I put my palm on his head and shove. Immediately I hear the muffled gurgle and I know it’s working.

It turns me on, and I’m horrified that it does. I don’t show it though. “That’s enough.” I let him up. He coughs and wipes his eyes. ”Now it’s my turn.”

I bend down and grab Adam’s penis, pull his foreskin up around my tongue, and swirl around. His taste is gone already, so I start blowing him. Moment’s later, he’s humping me from below. We fall out of sync so he grabs my head. It works, and I feel him shooting, filling my mouth with his sperm.

I’m the only game in town now, and both of them take turns sucking on me. But I came too recently, so help them out.

“Where should I cum?” I ask.

“On my chest,” Jack offers immediately.

I kneel over him, my butt to his neck, and start shooting. Then I just keep going.

When I’m done, I hear Adam snigger.

“Oh wow,” Jack says.

It’s like he’s been sunbathing in thunder shower. I’ve covered Jack’s whole chest with thick drops of cum. They start to pool under his pecs.

“Yeah, uh, sorry man,” I say, grinning proudly. He starts to wipe himself with a tissue, then gives up and goes to the bathroom for a towel.

Adam and I pull on our shorts and continue our conversation from the drive over. When Jack comes back with two gnome-mugs full of water, we’re talking about anal intercourse.

“It’s just not something I’ve ever fantasized about,” I tell him. “I can never meet up with a lot of guys again, because they want anal.”

Jack herds us towards the pile of shoes near the door.

“Don’t do it,” Adam tells me. “It just hurts for the first few inches. And with Asians… I mean if his cock isn’t long enough, that’s all you get.”

“But you’re a bottom, right?” Jack says. “You’re just trying to keep all the fun for yourself.”

Adam laughs, unable to keep a straight face. “Yeah, I am.”

“Would you like anything else? More water?!” Jack asks, making increasingly panicked glances toward the door.

“Um, no, I guess we should go now?” I suggest.

I drive Adam back through the 5pm traffic, and we chat about work and life, but mostly about sex. It’s wonderful to be able to share with someone, and I’m disappointed when he gets out at the bus stop. I can’t help thinking I’ve made two new friends. Or at least the beginnings of buddy-ship.

The next morning when I check my phone, I get a message from Jack.

“Hey Pete, I’m going to uninstall grindr now. I think it’s time for me to stop playing around and get settled down with my fiancee. Thanks for the fun time we had ;)”

I smile, recalling the previous afternoon. I’m sad to lose him, and happy for his new life. Plus, for the next while at least, I am the last man to cum on him.

Extra Marital Bliss

“Hey man, wanna come over to my condo at lunch today?”

An apartment with a bed and no pesky room-mate around? Meeting horizontally is a rare treat in University Town.

“Sure,” I write back. I balance the phone on the toilet tank, and grab a diaper. My 11 month old just woke up. My wife should be back soon to take over and I’ll leave for work.

Yesterday I’d been chatting with this bi torso. He’s engaged, and we seem to get along well.

“Have you ever tasted your own cum?” he asks.

“Yup. It’s like sweet nectar of the gods. And bleach.”

“Hahaha… I can’t wait to taste it :)”

Those are words I like to hear.

I meet him in the lobby of his apartment. He’s asian, strong and compact. His gray T-shirt hangs off his V-shaped torso. We make easy conversation in the elevator.

In his apartment, the unmatched furnishings and the printer on the kitchen counter reveal that his fiancee probably doesn’t live here. His bedroom is spacious and contains only a bed. It would be Zen, except plastic tote boxes piled against the wall threaten to come crashing down at any minute.

Definitely not gay.

I look out at the trees far below the apartment window. The curtains are missing.

He comes up behind me and puts his hand on my shoulder. “Don’t worry. No-one can see us up here.”

I spin around. He’s so close I can smell the sweat on him. It seems like we should kiss, but neither of us want to go there. Instead, I reach down and peel his shirt up, revealing a set of honey-brown abs. In a moment, we’re both down to our underwear.

“This will take longer than five minutes,” he tells me. referring to my other story. He kneels and munches my goods through my underwear. (SAXX Kinetic Brief Fly, $30) I lean against the side of the window and watch him, and run my hands down his back.

But one thing works best to turn me on.

We switch, and I pull down his black boxers. His uncut cock juts out at me, his glans perfectly pink and smooth. It looks like the perfect size for me. I just have to know, so I skip to the good part: I take it all in. It tastes wonderful, and its smooth end just lightly nestles against the back of my throat. I know immediately that I am going to like this guy.

“Lay down, I want to suck you too,” he says. I settle onto the mattress.

“Oh wow,” he exclaims, as he grabs my 6.5” erection. I lay back against the wall as he sucks on my penis. God it feels good. My wife does it best, of course, but it’s been about six months since the last time.

“Want to 69?” I ask when he comes up to breath.

His eyes light up. “Sure,” he says, and we lie sideways against each other.

For me, the hottest part of a man’s body is the little crack between his legs, under his balls. I stare at his and pretend his cock is candy. It’s his turn to moan. Everything I do is turning him on, and he returns the favour.

I use his moans as a guide, and bring him to the edge, then back down, once, then twice. I love teasing him, but he shifts his weight, and suddenly he’s in control. He’s on top of me, thrusting down, pressing his penis against my throat. It just fit before, but now he’s more aroused. With his bodyweight, he shoves himself all the way in, and I panic. I can’t breathe.

I push his hips up and take a quick breath, so I can stop gagging. But he plunges down again, banging against my throat, still moaning. I feel like I’m going to vomit. But it’s fucking hot. I feel utterly dominated. My mouth is his fuck toy.

I’m so distracted, I don’t notice my own feelings down there until they’re unstoppable. I’m going to cum, but I can’t warn him. I let out some desperate moans. And then it happens, sweet release. With the gusto of his urgent need, he sucks it out of me, hungrily.

And then he lets off, allows me to sit up. I quickly wipe the tears off my cheeks. He doesn’t notice. He half stands on the bed, grabs my head and starts to fuck my throat again. I reach around and pull him to me. His moans become faster, more urgent.

When he cums, it lasts a long time. I can feel every strong pulse against my lower lip. There must have been 10 spurts right down my throat, but I taste very little. Finally he drops me, and we both settle down into the bed.

Drained.

As our cocks shrink, we talk. He’s getting married in a few months.

“It’s good that you’re exploring now,” I tell him. “I never did.” I was shy throughout school. After only two awkward lunch dates with girls, I found my soul mate and never looked back. By then, it wasn’t a stretch to stay a PIV virgin until my wedding night.

“Yeah, I guess,” he says, and looks to the blue sky outside the window.

Gazing at the sunlight streaming in from the bare window, I have an epiphany. Bi men often seek other bi men, because the rest of the world sees us as shifty liars. Jilted lovers are quick to point accusing fingers if we happen to switch sides. It’s unfair, because most bi men have completely normal, committed, monogamous relationships.

Us? We are both cheating. We understand one another.

“How do you initiate sex?” he asks.

“Well, it’s rough right now with the baby,” I tell him. Before kids, Sunday was our day, but it ended up being once a month anyway. Now, with three kids under five, we’re both exhausted. The pregnancy was not a good one, and afterwards, the baby seemed to drain from her breasts any remaining whiff of her sexuality. Blowjobs were all she could manage. One night, fatigued after a long week at home with our son, she admitted that our “intimacy time” was yet another chore on her long list of things to do. I stopped asking.

“She gave you blowjobs?” he asks incredulously.

You poor man.

I dispense more marital advice, stories of battles over knives in the dishwasher, compromise, and how to live with your soul mate.

“It was easy to move in together,” I tell him. “It was different than a roommate, because I really liked her.” Like her, I quickly correct myself. “You know what they say. ‘Happy wife, happy life!’” I chuckle.

“Right.”