New York Magazine Sex Diary 3

By Hypnothrill -
published December 19, 2018

This week: an office manager who’s fantasizing about cheating on his wife. Male, 42, Long Island, straight.

{Author’s Note: Here are the final entries in the diary. Let me know in the comments how you liked the story!}

Day Five

9:00 a.m. The gym’s already so busy this morning, I can barely find a parking space. And when I get in there, it’s a total party atmosphere. A lot of guys on the gym floor are working out shirtless or even just wearing little posing straps, all the better to show off in. In the locker room, it’s even more sexual; in one corner, four guys are sitting on the benches having a circle jerk. I’m tempted to join them, but I know I need to get in an actual workout as well, so I change into my gym clothes and reluctantly leave the locker room.

It’s so hard to focus on my workout with so many distractions. It’s like an all-you-can-eat buffet of hot man meat out there, and I want it all! And to judge by the hungry looks some of these guys keep giving me, they feel the same way. I keep locking eyes with this one tattooed guy—a total Guido type in his late 20s—and then finally he motions toward the locker room and I follow. Pretty soon we’re all over each other—I pull his tight compression pants down with my teeth, and his thick Italian sausage springs up and hits me on the chin. Pretty soon we make our way into the sauna. It’s already pretty full; I see the bearded guy from yesterday in there and, even though he’s got his hands full fucking this blond surfer guy, I manage to catch his eye and give him a high-five. Then the Guido guy and I find some free space on one of the benches and start 69ing. We cum in each other’s mouths at just about the same time, and I can swear his cum tastes a bit like garlic and oregano.

On my way out of the showers, I spot four young guys having a circle jerk in one corner of the locker room. It takes me a second to realize that it’s my son and three of his friends (including Trevor). My son looks embarrassed, but I just smile and tell them to have fun. Then I give Trevor a little slap on the ass as I head over to my locker to get dressed.

5:30 p.m. I take the train into the city, then make my way to Dan’s Midtown apartment for his Super Bowl party. He greets me at the door, wearing nothing but an apron that reads “Kiss the Chef.” So I do, and as our tongues duel for a moment, I can feel his growing erection through the thin apron. Dan tells me that he’d love to play more, but he’s got some nachos and potato skins cooking, so I should just join the others in the living room.

I recognize some of the guys from work: Roger and Kent, two of the other doctors in the practice, are sitting on the sofa, and I take an open seat next to them. I notice that Kent’s shirtless and so are a few of the other guys. Actually, a couple of them are just in their underwear. And they all seem to be scoping each other out, casually rubbing their crotches, just waiting for the sexual tension in the air to turn into something more.

Finally, Kent asks, “Anyone mind if I turn on the TV?” And then we try to watch the pregame commentary through the static, but there is so much static, we can barely see, but we don’t mind the static, we just keep staring at the screen, staring at the static until a pattern emerges, and I find that I like staring at the pattern, and I keep on staring until I feel a hand unzipping my jeans, and I look over and see that it’s Roger. And then I look up and see that Dan’s standing in front of me, his hard dick sticking out of the side of his apron. And so I start sucking on Dan’s dick as if my life depended on it, while meanwhile Roger starts sucking me off. And then I can tell Dan’s getting close, so I stop sucking and tell him that I need him to fuck me, that I want him to be my first. And then someone (Is it Roger? Is it Kent?) is licking my ass, getting it ready for Dan’s big dick. And then Dan’s inside of me, and it feels amazing, he feels amazing. And then I look over at the TV and it seems like somebody just scored, but through the static, I can’t tell who. And then Dan’s spewing his hot load inside of me, and it triggers my own orgasm, and I shoot inside of someone’s mouth, but I can’t tell whose (Is it Roger’s? Is it Kent’s?)

11:00 p.m. After we all have a few more orgasms, breaking for rest and beer and nachos and potato skins in between each round of our Super Bowl orgy, the party finally breaks up, and the guys take their showers, get dressed, and head home. I know I should get home too, especially with the long train ride back to Long Island, but I want an excuse to spend more time alone with Dan, so I offer to help him clean up. We’re both still naked and covered in drying cum, but we go around the apartment together picking up all the dirty plates, washing the dishes, wiping the semen off the furniture. It feels nice. Cozy couple time. And when Dan asks if I’d like to stay the night, I gladly accept. I fall asleep with him spooning me, holding me in his arms, feeling the comforting weight of his big dick pressing up against my buttocks.

Day Six

6:30 a.m. I get up before Dan, so I decide to wake him up with an early morning blowjob. He wakes up with a smile on his face and tells me that I’m the best. “Better than all your girlfriends?” I ask, and he just laughs and nods. I feel like I could stay between Dan’s legs forever, but we’ve got to get ready for work, so we get out of bed and take a shower together. Afterwards, we shave in front of the mirror, and it’s so cute how Dan insists on shaving me, lathering up my face, then running the razor along my cheeks with the steady hands of a medical professional. I have a brief moment of panic when I realize I didn’t bring along a change of clothes and I have nothing to wear for work, but Dan lets me borrow some of his clothes. Luckily, we’re just about the same size, though Dan fills out these clothes a lot better, with his barrel chest and broad shoulders. (Have I mentioned what a HUNK my boyfriend Dan is?).

11:00 a.m. I’ve been multitasking this morning, filing patient records on the computer while responding to Grindr messages on my phone. Feeling a bit bored, I decide to wander down the hall and see what Dan’s up to. No surprise: he’s in one of the exam rooms, fucking a patient. Dan waves me over, and pretty soon the patient is sucking my cock while Dan fucks him. Then I get the patient to roll over on the exam table so I can jerk him off while he’s still sucking me off and getting fucked. As the patient shoots his load in my hand, Dan makes a little joke about how we run a full-service clinic here.

3:00 p.m. I’m feeling bored and horny again, so I wander out of the office in search of Dan. I don’t find him, but I do come across Roger and Kent having an orgy with a couple of patients, and so I strip off my clothes and join them.

6:00 p.m. After the workday is finished, Dan stops by the office to find me, gives me a little kiss, and asks me if I’m ready to hit the gym with him. He tells me he’s going to ride my ass at the gym, then after we get home, he’ll ride my ass in a different kind of way.

8:00 p.m. Dan wasn’t kidding. That was a hell of a workout. (And afterwards, in that orgy in the steam room, we engaged in a different kind of workout). I’m worn out, and ready to head back to Dan’s place for some dinner and a quiet night in, but Dan wants to try this new Korean restaurant and then go to this private sex party in Soho he got us invitations to. You see, this is the great thing about having a younger boyfriend; he pushes me out of my comfort zone and gets me to try new things.

Day Seven

6:00 a.m. I’m the first one up again, so I make myself some coffee, then wake up Dan with a nice blowjob while giving a handjob to Ryan, this guy we met at the party who spent the night with us. After he blows his load all over my arms and chest, Ryan gives us both a deep kiss and takes off. Dan and I take our time and have a nice slow fuck in the shower. Damn if his cock doesn’t feel like it’s just made for my ass. After the shower, Dan shaves me again, then makes a little joke about how if we’re going to be living together, I need to buy my own toiletries. We both know what he’s asking, and even though we’re moving so fast, nothing would make me happier than moving in with my sexy boyfriend.

11:30 a.m. After Dan and I doubleteam a patient, I wander back out to the waiting area and see that we’ve got a bunch of patients lined up to see the doctors, and they’re getting impatient. All this sex is really slowing down our turnover rate. As Office Manager, I know that patient satisfaction is an important part of my job, so I give out complimentary blowjobs to all the guys sitting in the waiting room. After a while, Dan comes out to see if I want to grab lunch, and he sees me on my hands and knees, cum dripping off my face and onto the shirt and tie he loaned me. And then he gets down on his hands and knees too and starts blowing the guys I haven’t gotten to yet, so I can finish up quicker. Have I mentioned yet what an amazing boyfriend I have?

1:30 p.m. After lunch, I decide to call my wife and let her know that things are over between us. She’s cool with it and lets me know that her friend Liz is moving in with her and they’re a couple now. I never thought Liz was very attractive, but to each their own I guess.

6:30 p.m. It’s my son’s 19th birthday today, and I’m throwing a big surprise party for him at the sex club by Union Square that used to be a Barnes & Noble. He thinks we’re just going out to dinner, so on the walk over, I decide to get the hard stuff out of the way and tell him that his mom and I are splitting up. My son takes it pretty well and says he saw this coming a long time ago. Then he perks up when I tell him about my new boyfriend and show him a naked photo of Dan on my phone: “Way to go, dad! You’ve bagged yourself a hunk!”

He’s even more surprised when we walk into the sex club and a bunch of his friends from high school and college jump out to greet him; Trevor is there, and I invited his “Uncle Colin” as well (and of course, Dan). I booked the club’s private playroom (in what I think used to be the Classical Music section of the B&N). There’s a sex sling hanging from the ceiling, so of course the Birthday Boy gets to climb in there first. And of course he wants Dan to be the first to fuck him. Like father, like son!

I move over beside Trevor and we start jerking each other off as we watch my boyfriend fucking the shit out of my son. And then Trevor and all my son’s other friends take their turn shooting their loads up his well-fucked ass.

Finally, all the others have had their turn and I’m the only one who’s left. I try to bow out, because it just feels too awkward; my son and I have barely talked about sex, much less fucked. But the others egg us on, chanting to the tune of a 50 Cent song: “Hey boy/ It’s your birthday/ Time to ride the / Dick that made you.”

And once I get in there, I’ve got to admit: my son is one hot piece of ass. His hole’s still so tight, even after taking 10 other guys’ dicks. He leans forward in the sling and we kiss deep, savoring the father-son bonding moment.

After I deposit my baby batter deep in my son’s hole, Dan comes up to me and whispers, “You looked so hot fucking your son like that. Maybe later I’ll let you top me.” Oh man! I can’t wait!

It’s been such a crazy week, but I finally feel like I’m living the life I’ve always wanted!

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