MY SUMMER OF SEX WITH COWBOY
Chapter 18
By Donny Mumford
Gregory was pretty good. After three days without Bruce fucking me, I've resorted to paying for sex. I paid twice, actually; I paid the pussy boy online site and Gregory. And, I just paid for another date with him tomorrow at four o'clock. I used to sneer at people who needed to resort to prostitutes, but now I don't. It's convenient and, while I hate to admit it, I gotta say the pussy boy site makes it easy, and they have an excellent stable of hot, clean-cut young guys to choose from. Plus, as a recent returnee to bottoming during sex, I find submissiveness adds to the sexual experience, and a paid prostitute tries to accommodate his client's desires. Gregory didn't have Bruce's knack for dominance, but he was okay.
It's not fair of me to compare Gregory to Bruce, anyway. I mean, Bruce has been mentoring submissiveness into my training from the very first minute we met. It was subtle programming that, first, got me to accept the concept that he's my main man and that I had no choice but be submissive to him. Once that was hardwired in my brain, he kept reinforcing the concept until I began embracing his dominance. Now I love the submissive sense I feel toward Bruce. He followed the manual, but I think he's also a naturally dominant type. Being submissive to him is an automatic reaction now; it's like wearing your favorite old super-comfortable pajamas. Bruce creates submissiveness that's smooth and requires very little of me as I merely need to do what I'm told. I find it to be pretty sexy.
That's true, but it isn't the only reason I want to save him. Mostly, I want to help him get out of this life he's in because it's a dead-end. He may tell me to go fuck myself, that he wants to finish his punishment, then start from ground level, working his way up to qualifying as a mentor again. I'd guess it's fifty-fifty which way he'll go, but I'll know I did everything I could, and that will need to satisfy me no matter the outcome.
While not perfect, Gregory was as good a substitute for Bruce as I could have hoped for my first time using a paid prostitute. I needed sex, and he came through for me. I hug myself because my ass feels good right now. But, seriously, that one fuck isn't going to be nearly enough. Nope, one fuck in three days doesn't hack it, not after Bruce trained me to expect three fucks a day and four a day starting next week. Um, of course, there won't be the next week thing.
Hmm, I've got a date with Gregory tomorrow afternoon, but I need to plan beyond that. I'll try to get a date with Gregory's friend Jimmy for tomorrow night. I go online to the pussy boy site again, and peruse the site, then call the main number to talk to Gregory's main man again, his pimp actually. He questioned me, sort of pre-qualifying me to have a date with one of his boys as if I didn't just go through this. I'm not a regular yet, so ya know. Still, considering the fake name I use, Tom Jones, I would have thought he'd remember that.
Anyway, he's polite about it and finally agreed I could have a date with his boy, Jimmy O'Neil, whose picture, if current, indicates he's even younger than Gregory. I'm into youth now, probably because of both Cowboy's and Bruce's influence. Plus, I really like the hairless bodies of the pussy boys, although Gregory's body isn't especially hot other than the hairless part.
So, Jimmy's due at eight-thirty tomorrow. That works out as Lee and Cowboy will be at their Broadway show. As a bonus, maybe Jimmy will have some news about the sweatshop, which, after all, is my main reason for being here. Okay, I've taken care of two dates for tomorrow, and now that I've got time on my hands, I'm at a loss about what I should do with it. I need someone directing me.
After thinking about it for a while, I go to Bing for information about where I might find some street boys selling their bodies. Huh, I find that the number of street solicitations has been radically reduced in the last ten years or so. The Internet has a lot to do with that, I suppose. Well, I've nothing better to do, so I get the doorman to hail me a cab, and when the cab driver asks where I want to go, I say, "I'm interested in underground gay sex operations. Do you have any suggestions?" He pulls over and says, "Get the fuck out, pervert."
Huh, standing on the sidewalk, I suppose I should feel humiliated, but I don't. Over the next hour, I flag down three cabs, which is not always an easy task in NYC nowadays due to the emergence of Uber. That company requires an app that I don't have. Anyway, the next two cabbies tell me approximately the same thing the first guy told me... get the fuck out. I'm still not humiliated, and I didn't pay those cabbies, so it's their loss.
The third guy, of undetermined nationality, said something that didn't include, get the fuck out, although I don't know what it was that he said. In any case, he drove me around for twenty minutes running up the meter before finally pulling over at 8th street in front of the Greyhound-Port Authority Station. I give him a fifty-dollar bill and, when he doesn't offer any change, I get out and wander around feeling like a pervert, which I basically qualify for, I suppose.
All the youthful guys, and girls, hanging out here look like they're homeless. They all have the ubiquitous backpack on, and I wonder what the hell they have in them? After fifteen minutes, a girl asks me, "Can you spare ten bucks so I can buy a bus ticket home?" Obviously, that's bullshit, but I give her a ten anyway. She smirks and slinks away without saying anything. Swell.
I'm about to hail a cab back to the Waldorf when a boy with skaggy long dirty-looking hair, who couldn't be more than sixteen, ask, "Dude, twenty-five dollars, and I'll jerk you off." Well, at least I've made contact with a youngster selling himself, but he's too young to have anything to do with the pussy boy organization. Maybe he's heard something, though. And, no, I'm not going to get jerked off my this dirtball, but I walk with him to a spot behind a dumpster and ask him, "Do you know anything about a sweatshop for gays? You know, where a guy might walk around and fuck guys in hammocks?" That's all I remember Eli saying about the place. The dirtball goes, "No, do you want me to jerk you off, or what? I'll blow you for fifty bucks." Poor kid. I give him a hundred-dollar bill and mumble, "Buy a ticket home," then walk away.
Huh, like the girl, the dirtball smirked at me without a word of thanks. It takes me twenty minutes to hail a cab, and then the roundabout way the cabbie takes to the Waldorf costs another fifty dollars. Fucking thieves!
It's almost seven o'clock when I get back in the suite, and, from the condition the bathroom is in, it's obvious the boys showered before heading out for the night. I pick up the towels and clothes they left lying around. Then I took a shower. After that, I eat in the really nice Waldorf restaurant, and I'm back in the suite waiting for Jimmy O'Neal at eight-twenty.
As I'd expect of a pussy boy, at precisely eight-thirty, there's a knock on the door. I open it, and there stands a five-foot-nine slightly husky young man who can't be older than seventeen, but most assuredly, he is older because they wouldn't risk getting in trouble with the law by having an underaged escort. I smile and say, "Jimmy O' Neal, I presume." He looks stern, as stern as his babyface will allow. He goes, "I'm looking for Tom Jones." I sweep my arm, inviting him in, mumbling, 'Well, you've found him. C'mon in."
As he walks past me, I get a whiff of him, and he's wearing the same cologne Gregory wore. Well, they are best buds and lovers, so they probably share what I think is probably expensive cologne. Closing the door, I go, "I'm still not the police." They always seem to ask that, so...
He says, unnecessarily, "You have fifty-nine minutes left in your hour with me. Additional hours are at $300 per hour." I knew that already. I'm more relaxed now that I've had the experience with Gregory and the mystery of doing this isn't an issue for me now. I go, "Shall we have a drink?"
He's looking around the suite without answering me, so I say, "Is there a drink you prefer?" He looks at me and smiles, but only with his lips, saying, "How lovely. Yes, I'd like a shot of whiskey and a beer." Then he sits down and waits for me to serve him. Cheeky of these pussy boys. They both do the same control thing. In the manual, it must state, 'At all times pussy boys will control the situation while, at the same time, accommodating your client.' They could add, and never mind the outrageous cost your client is paying; you're in charge.
Ha, that's more than fine with me. I get two beers and a tiny bottle of VO that I pour in a glass and hand to Jimmy along with the Heineken beer. He says, "Thank you, Tom, but you need to have a shot with me. Show some class; don't make me do a shot by myself." Just more control, obviously, but as I said, that's fine by me, and I even add, "Yes, Jimmy."
After pouring an ounce, or actually, these tiny bottles are an ounce and a half. I walk back over to him, and Jimmy lifts his glass to tap mine, and he flashes down the whole ounce and a half, going, "Oh, fuck!" His eyes watering. He takes a swallow of beer, saying to me, "Drink the rest of your whiskey, Tom." I already feel a submissive sense forming, so I do as I'm told and gulp down the whiskey and a swallow of beer. I can drink shots all night, but it doesn't appear young Jimmy could handle more than one.
He swallows some more beer, then says, "Greg tells me you need to be told what to do, so go in the bedroom and strip, then call me when you've done that." Ordinarily, I'd imagine, the prostitute doesn't give the orders. How would I know, though? Anyway, with me, they're accommodating what they think I want, and they're right too because I get off on being told what to do. After fifteen years as Ronny's wingman, then five years in the Navy, plus three weeks with Bruce, it's been ingrained in my soul to do what I'm told.
I notice the cum stain I left on the bedspread earlier in the bedroom, so I pull the bedspread off the bed and stuff it in a closet. I take this opportunity to do what I should have done after dinner and go to the bathroom to brush my teeth. In the bedroom again, I take everything off and, standing here naked, call out, "I'm naked, Jimmy."
Hmm, I need to force myself not to stand at attention. Jimmy strolls in carrying what is obviously a new bottle of beer. He looks right at my cock and nods his head, then drinks a few swallows of beer and asks, "Can we eliminate the massage, do you think?" That was cool... he made an order sound like it was my choice to do away with the body massage, which, after all, is the only activity covered by the five hundred dollars.
Nodding my head, I go, "Sure, Jimmy." He's still fully dressed and neat as a pin with a very recent pussy boy haircut. Unlike Gregory, there is nothing swishy about Jimmy; in fact, he's gruff and macho, or as gruff and macho as a five-foot-nine baby-faced gay guy can be. He's also cuter than his picture. He has the clear pale complexion I'm attracted to, big brown eyes, and light blond hair, although there isn't much left of it on his closely cropped head. He has sexy bowed lips, pouty lips, and a smallish chin that goes with the rest of his face.
Swallowing more beer, he says, "What are you looking at?" and I realize I've been staring at his face. I gulp and say, "You, I was looking at your face. You should be in male modeling." He goes, "I've done some of that. Have you ever seen the ad for Oreo Cookies? In one of their ads, I was holding and opened Oreo cookie, one plain side and the other with all the icing, and I'm grinning like mad."
I don't look at ads, but I lie, "Oh, yeah, it's you!" He shrugs, mumbling, "It was me. That was two years ago, just after I was qualified by my pimp, Levy Jordan, who is now my main man." I go, "You don't seem old enough to be a pussy boy for two years." He goes, "Well, be that as it may, I am old enough. They do not deal with underaged recruits."
The Oreo cookie discussion seems to have put him in a sweeter frame of mind. He asks, "Well, what the fuck can I escort you into doing, Tom?" Without realizing I'm going to say this, I go, "Um, can I suck your cock?" He goes, "Of course. Do you know the price listing for extras?" Nodding, I say, "Yes, Jimmy," and he holds his arms out, saying, "Go to it then. Pull my dick out and have a blast. If you suck me off, though, it means we'll be going into hour two before I'll be able to fuck you up real good." Nodding again, my mouth salivating, I go, "That's alright. Does the price include licking your balls?"
Swallowing the last of his beer, he burps and says, "No, not really. If you want the whole package of rimming, licking my balls, and sucking me off, it's bargain-priced at $175 plus a tip." Nodding for the third or fourth time, I'm so anxious to do this, I have a difficult time saying, "I'll do the whole package." It came out in a squeaky voice, and he says, "Well, okay, you can start by taking my clothes off."
He has a bossiness to his personality that seems natural and not forced or put on at all. This is how he probably is with his lover Gregory, meaning Jimmy is likely the top in their relationship.
I take his clothes off piece by piece; Jimmy is as relaxed and comfortable while I do it as anyone could be. In a way, it's like he's the one paying. His body is, of course, completely hairless, which I love, but his penis is disappointing. I don't let that show in my facial expression, though. He has an average cock about five inches, at the most, but unlike Gregory's, Jimmy's cock has a normal heft to it. It's not a fatty one at all. He's pale all over, though, with beautiful taut skin, and his complexion is identical to Bruce's skin coloring. Jimmy's blond hair, big brown eyes, and pale completed skin make him a shorter, stockier version of Bruce minus two inches of cock. Also, I need to admit; Jimmy's cuter than Bruce.
The odd thing is, I was going to request Jimmy because he's Gregory's boyfriend. Then I really wanted a date with him when I saw his baby face, but I never thought of comparing Jimmy to Bruce until now.
Jimmy hands me his empty beer bottle, saying, "Put this someplace and then start with rimming my ass as I lie on my stomach on the bed. When I tell you to stop, I'll roll over, and you'll lick my balls until I tell you to stop, and then the prize, you can suck my cock until I blast a load of cum down your throat. Deep-throating is okay, but only if you can do it without gagging. I hate the gagging sound."
Putting the bottle on the bureau, I'm definitely sensing submissiveness now, so I raise my hand the way I did with Bruce when I wanted to ask something. Jimmy doesn't blink an eye at that. He nods, mumbling, "Go ahead. What do you want to say?" Gulping, I manage to squeak out, "You're going to lie on the bed?" He goes, "Yep, that's the way I do it. I'm not standing and bending over for you. You'll need to do the best you can with me lying down." I go, "Yes, Jimmy," and he says, "Hey, Greg said you were a pussy boy in training, so didn't you learn to rim a guy's ass while your client lies on a bed?" I'm the fucking client, but I let that slide.
Shaking my head, I go, "No, my mentor didn't get to that. He was, um, fired after my third week." Jimmy mutters, "That explains it then because it is an advanced technique for week five or six." He gets a grip at the back of my neck, squeezing hard, leading me to the bed, saying, "There's a time limit for rimming, licking my balls, and sucking my cock, but I won't tell you what it is. Don't goof around because you'll want to get all you can from the rimming, licking, and sucking, never knowing if the time is almost up. Do the best you can and enjoy my body!" I nod, "Yes, Jimmy." Okay, I'm feeling fairly submissive to him now. The grip at the back of my neck had its intended effect, and I felt a tightening of my cock.
He lies on his stomach, saying, "Good, you took the bedspread off. The germs on bedspreads, well, never mind that. Oh, and I need to tell you if you shoot off, it's another fifty dollars. A total of $225. Got it?" "Yes, Jimmy."
He looks at his Rolex wristwatch, mumbling, "Your rimming time starts now!" Climbing up on the bed, I get on my knees between his legs and lean down to do long licks on his hard butt cheeks, the skin tight and pale and nice smelling. Jimmy's obviously conscientious about keeping his ass clean when on duty. The only time I smelled excrement and tasted it briefly while rimming was Bruce's ass was when it wasn't expected that time; he let me do it as a favor to me.
When Jimmy's butt cheeks are covered with my saliva, I spread them wide and then bury my face between them, pushing my nose firmly against the top of his ass crack and pushing my tongue way out, reaching just behind his scrotum then dragging my tongue over his asshole, and shiver with a submissive sense spiking in my brain. After lapping over his anus several times, I need to lift my face to inhale deeply. I take another deep breath because I can't breathe with my face against his ass. Keeping his buttocks spread, I get a good look at his anus. Huh, I haven't seen a lot of assholes up this close, but the few I have seen all look the same--tight rosy pink rosebud anuses.
Rimming a guy's asshole is a very submissive act, and submissiveness grabs me tightly. It's incredibly sexual and very arousing. My face goes snuggly between his buttocks again as I'm pressing my tongue on Jimmy's asshole. And, just like that, my cock tightens from flaccid to hard and then harder as it moves up against my belly. A whole group of enormous sexually submissively hot vibrations streak all over me. With my face against Jimmy's ass, my nose pressed tightly against the top of his ass crack, my mouth and cheeks partly in between his butt cheeks, I not only can't breathe, but I can't make audible moaning sounds either. I'm moaning with deep arousal, but only in my mind.
My tongue again reaches the back of his scrotum, poking it before dragging back across his asshole. I need to breathe, but I can't stop licking his asshole, and then I have to pull my face away again to gasp in a lungful of air. Then, I'm right back with my face between his buttocks again, my tongue licking and poking at his asshole until I feel the lips of his anus moving. Jimmy's body gets tight as he's squirming and grunting on the bed.
That's a good reaction from him, but I need to get my tongue up inside his rectum. I poke at his anus' lips until they surrender and give up the fight. Yes, Jimmy's anus, something is coming in the wrong way whether you like it or not!
My tongue victoriously squeezes up his asshole an inch, and then it begins fucking his asshole. Not for long, though. My throbbing boner drools pre-cum; yep, my climax has arrived on the scene. One last lick across his asshole, and I pull my face up, gasping in oxygen, then I go, "Ahhieee," a girl's squeal as my boner fires cum from the gaping piss slit, cum streaking warmly and creamily up my stomach and onto my chest. Another weaker shot of cum follows as my cock throbs and then quiets down. I shudder with the pleasure that can't be compared with anything else.
Jimmy does a shiver, too, then says, "Times up." I ignore that and lick along his entire tight ass crack dragging my tongue with pressure making Jimmy shiver again. My tongue aches and my toes clench, then I sit back and breathe normally, thinking, 'that was almost as good as rimming Bruce's ass.'
Looking back at me, Jimmy goes, "Who the fuck was your trainer? And, did you say you were only into week four?" I go, "His name is Bruce Dunlop, but we never got into week four." He goes, "Holy fuck, you must be a quick study. That was an excellent ass rimming. For now, though, get into the bathroom and clean the cum off your body."
I'm still vibrating a little from my stunning climax as I. walk into the bathroom and clean the cum off me. It's disappointing I've already blown my load, and I still have balls licking and cock sucking to do on Jimmy. As I said, there aren't many more submissive acts than rimming a guy's asshole, so I couldn't help blowing my load.
When I'm in the bedroom again, I see Jimmy's lying on his back with his hands behind his head. I crawl up on the bed and move his legs apart, then lean down from a kneeling position and gently move his penis up against his belly, holding it there with a finger, then lick his scrotum and lift it with my tongue, feeling his balls slide around. Holding his penis against his belly with my forehead now, I put a hand on each of Jimmy's thighs and lick the side of his left thigh and the side of his scrotum at the same time. Then lap four times at just the side of his scrotum. There's no taste but a faint smell of bath gel. I lick up and over to the other thigh and suck on his leg where the scrotum connects to his crotch. Ohh, nice skin on Jimmy. I find it fabulously sexy licking and sucking an attractive guy's body, my nose dragging along inhaling the male, barely detectible scent; it's a faint scent hidden under the bath gel scent but extremely pleasant.
After sucking his lower nut in my mouth and pushing it around a little with my tongue, I let go of it and do the same thing with his higher nut pushing it so hard with my tongue, Jimmy goes, "Awk.. ahh..." Then, I let go of it, and I lick down the edge of his scrotum, where it's attached to his body. Then over where most people have pubic hair. My cock is another hard boner by now, and Jimmy's cock is getting hard against my forehead. I spend a minute licking all around the groin area and then up to his belly button feeling his stomach muscles clenching as Jimmy goes, "Mmmm, ahh, ahh," rubbing my head, murmuring, "I'm gonna cum... stop."
He pushes my head away, but not roughly. I felt his cock getting hard, and now I can see it is hard as wood with a bubble of pre-cum at the piss slit. He takes a deep breath, then says, "I want to shoot off in your mouth, which is what you paid for, so I had to put a halt to the balls licking for a minute." I'm looking at the bubble of pre-cum. Jimmy sees me looking at it, wipes his forefinger across it, and holds it out to me. I suck on his finger, getting the cum bubble on my tongue but don't notice a taste. Maybe a touch of sweetness, though, like putting a few particles of sugar on your tongue.
Jimmy says conversationally, "You're oral skills are advanced past week three training, so I assume you've been blowing and sucking guys off since you were very young." I've only been doing it for three weeks. You know, after a four-year period of not doing it even once. Not feeling like explaining, I mumble, "We all tend to do things very well that we really like doing."
He sort of shrugs, then says, "Your ball licking time was just about up anyway. My dick has softened up enough, but I need to take a piss before you suck me off. Beer runs right through me." Sliding off the bed, he says, "You can hold my dick while I pee if you want. No charge." I mumble, "No, that's alright," and, walking into the bathroom, he says, "Some guys are into urine, ya know? Just a thought."
That was nice of him to offer me that for free, but I've never had any interest in urine play. And, I know urine is supposedly sterile, but how the hell can that be true?
When Jimmy's back from peeing, he fluffs some pillows and sits up on the bed resting his back against the pillows, saying, "Okay, with your oral skills, I'm expecting a great blowjob. There's no time limit. You go until I blow a wad of cum down your throat."
Nodding my head, I get on the bed on my knees and, with a hand on each of his thighs again, I lean down and lip his penis into my mouth. A drop of piss tastes bitter, but only for a second or two, then it's only the non-taste of Jimmy's cock. I take my hand off his leg to hold his penis at the root and lick up and down the shaft starting at his scrotum and going up to the cute head. His dick is skinnier than mine, but it's a serviceable penis, I'd imagine. He certainly hasn't seemed at all self-conscious of its size. It's a cute penis with a pointy head, just not at all large.
When I suck on just the head, my tongue twirling around it, I pretty quickly get it growing into a hard little boner. Now that I've got it boned-up, I move it all around in my mouth. Then, wrapping my arms around his waist, my lips cover my teeth, I bob up and down on his hard cock, my jaws closed tightly on the shaft, basically jerking him off. He goes, "Ahh, fuck..." and straightens his legs out on either side of me, squirming on the bed and rubbing my head.
The eighth or ninth bob, my face goes forward so far my nose is tight against his groin, and the head of his cock goes into my throat. No gagging as the pointy head goes in and out of my esophagus easily, two, three, four times with Jimmy making grunting sounds, lifting his ass off the bed, his body stiff as a board, and with a moan, "Ahhhee," he blows his load down my throat.
When I had each of his balls in my mouth, neither one seemed especially big, so his orgasm maybe wasn't huge either, although it shot right down my opened throat, so I have no way of knowing its size. My head moves back, and a follow-up spurt of cum hits my tongue. Huh, I was right about the pre-cum because his cum tastes like, well, yeah, a little like candy. It had a sweet after-taste anyhow. Nice, actually.
Smacking my lips after moving my mouth off his cock, I look at him, and Jimmy mutters, "Fucking fantastic, Tom. Too quick of an orgasm, but that's my bad. That was a near-perfect blowjob, dude." I'm looking at his still firm penis, and there are some drooling cum bubbles at the piss slit. He grins, saying, "It's okay; you can clean it up." Leaning over, I take his still firm cock in my mouth, all of it with the head popping into my throat again, and then back my head off it an inch or two to suck on his penis like it's a candy cane. Taking it out of my mouth with my thumb and forefinger and holding it there; it's shiny with saliva, and, as I said, it looks somewhat cute.
Jimmy takes it from my fingers, mumbling, "I thought you were going to take a bite out of it the way you were staring at it." I snort out a chuckle as he pulls on his dick, saying, "I should be paying you the $225, but fortunately, that's not how this works. Do I have a great job, or what?" I'm sitting back on my heels at the very end of the bed, shrugging and saying, "Hell, I loved doing all of that, Jimmy." He says, "Any time, Tommy... any fucking time you want, feel free to arrange a date with me through the pussy boy site. Greg told me you were a primo client, and he's right."
I'm grinning, staring at his cute face again, and he says, "Come over here, and I'll give you your tip." I'm like, "Wha..." as I lean toward him, and he puts a hand on either side of my head and kisses my mouth with his active tongue sliding on my inactive one. That took me by surprise, making it all the more enjoyable. It was a five-second hot pussy boy kiss after which, still holding my head between his hands, he says, "Maybe Gregory and I should adopt you as our boy toy. Hey, how old are you, anyway?" I lie, mumbling, "Twenty-three, why?" Letting go of my head, he mutters, "That's what Gregory guessed. Dude, do you realize how hot you are? Your fucking body rocks, and you're a really good-looking motherfucker too!"
Muttering, "Thanks," then I don't know what to do, so I ask, "What do you want me to do now?" He snickers, "Dummy, that's what the escort is supposed to say to you." I shrug, "Yeah, I guess." He says, "Well since you don't know, you need to call the site and pay for another hour. They'll send me a code on my cell phone that another hour's been paid for, and we can chill out until my balls work up enough juice for me to fuck you. How's that sound?"
Nodding my head, I slide off the bed, mumbling, "Sounds good. I'll do that now." I use the second of my three $1000 prepaid AMEX cards to book Jimmy for another hour. Jimmy gets his naked body under the covers, saying, "Get us a couple of beers and turn the TV on to the Met's game. You can get in bed next to me, and we'll watch my favorite baseball team find a new way to lose."
Taking the last two Heineken from the refrigerator, I give one to him and get under the covers. He hears his cell phone ping that my payment's gone through and mumbles, "There's the code," and he pulls me over right next to him, then puts his leg over mine, saying, "You can suck on my tits if you want. I won't charge to you, although that's normally $50 bucks a nipple." I lean against his smaller body and mutter, "Thanks, but, um, a little later maybe."
Without talking, we watch two innings of the game, then I get a brainstorm and say, "I can't believe I haven't followed up on something. Um, my mentor talked about putting me on the street soliciting blow jobs and backseat fucks here in New York. Where does that take place?" He goes, "Oh, you asked about the sweatshop, which most of us half-believe is a bullshit story to scare recruits into behaving. The street action mostly takes place around porn shops, and there are many of them in the city. We're taught to be subtle about it, mostly using eye contact. Obviously, we look like preppy nerds with these haircuts and preppy clothes, but that's the genius of it. Rarely are we ever hassled by the fuzz."
I'm like, "Huh. No shit. Um, where exactly are these porn shops?" He shrugs and goes, "How about if you order room service for more beers and some kind of snacks like potato chips and dip, or some fucking snack like that?" I go, "Oh, sure, Jimmy."
His naked body, so much like Bruce's in some ways, is hard to pull away from, but I use the room's phone to order a six-pack of Heiniken and chips and dip. I'm told they don't have that on the room service menu, so I'm like, "What's your second choice for a snack, Jimmy?" He goes, "For Christ's sake, Tommy, can't you make a decision?" I show my palm, whining, "I'm sorry, I want to order something you like." He sighs, "No, I'm sorry. You're a sweet guy. See if they have a tortilla chip and dip." They do, and I order it. The guy says, "Yes, sir. Fifteen minutes."
I get back in bed and slide over to my miniature Bruce, and he goes, "No offense, but you're easy to take advantage of, dude. I don't want to, but it's hard not to. You need to toughen up, or NYC will eat you alive." I'm not going to tell him I'm pretty tough already after surviving mind-numbing life-threatening danger in the Navy Seals, but I know what he means. It's just that Bruce has mentored me into a submissive frame of mind. With my tops, I can't seem to help myself. I like pleasing them whenever I can.
Snuggling against Jimmy, he casually puts his arm around me, which is a bit awkward since he's a lot smaller than me. I hunch down, so that's not as noticeable, and grin to myself. Obviously, this is an expensive way to have sex, but I've been missing intimate behavior with another guy after almost three days without Bruce as my leader. Hesitating, because I don't want to press the issue, I finally mumble, "Ah, where'd you say those porn shops were?"
Jimmy goes, "Oh, hell, it was two years ago that I was on the street. Let's see; oh yeah, my man put me on the street in the West Village. What were the names of those porn shops, though? Fuck, I saw them every day. Um, oh, yeah, Pleasure Chest was one and, um, Leather Man was the other one I remember. There were others, but those are the two I remember. Christ, I used to get some good results hanging around those two shops." I memorize the names and don't press for an address because that's easy to find on the Internet. Heh-heh, that's right, I'm nerd-ing my way to finding out what I want. Fuck James Bond.
The knock on the door gets me scrambling out of bed and wrapping a towel around my waist. I open the door, and a young fellow scurries in with six beers in a bed of ice and a big platter of Tortilla chip with a guacamole dip that has that disgusting artificial cheese and cut olives, and God only knows what else. I sign the $55 check and leave the cute guy a fifty percent tip, and off he goes thanking me profusely. Jesus, I hope Jimmy likes the dip because it looks gross to me. I don't like the taste of tortilla chips anyway. They taste like, um, perspiration or BO or something offensive.
Jimmy sits up to drink and eat, so no more cuddling. That's okay; when I get right down to it, he's not Bruce. This is a nice divergence, though. Jimmy dips a chip and holds it out to me, so I eat it, grinning at him. It's gross tasting, but I eat each one he feeds to me, not to be rude. The baseball game ends with the Mets losing 8 to 7. Jimmy pushes the half-eaten tray of garbage to me, saying, "Enough of this shit. Let's wash up, and then I need to use your toothbrush. After that, I'll fuck you good and hard, and then I need to get out of here. I have a midnight date with a foursome. That's a thousand bucks in my pocket. How about that?"
Jeez, maybe Bruce was telling the truth about retiring after four years of being a hooking pussy boy. We both go in the bathroom, standing next to one another, pissing out about twenty ounces of beer. I try holding my dick back a little, so Jimmy doesn't get embarrassed about his smallish penis. After washing our hands and face, Jimmy picks up my electric toothbrush, puts too much toothpaste on it, and uses it for like six or seven minutes.
Turning it off, he hands it to me, muttering, "Here ya go," and, pulling on his cock, he adds, "I'm getting psyched to do this." I mumble, "I'll brush my teeth later," and then rinse out my mouth with five mouthfuls of water, gargle with Waldorf's complimentary mouthwash, then hurry into the bedroom.
Jimmy goes, "Lean over the bureau, and I'll fuck an orgasm out of you. Then you owe me, um, you're a good guy, so let's even it off to five hundred with a hundred dollar tip." I go, "Yeah, sure."
So, this night cost me thirteen hundred bucks, but it's worth it because I've not only had a great sexy time already, I still have a fuck coming to me. Plus, I also found out where to look for a pussy boy who just maybe was in the sweatshop or knows where it is.
Jimmy nods his head at the bureau, and, leaning over, I put my hand on it, then push up my ass, getting my lower back involved the way Cowboy does it. Jimmy, of course, smacks my ass hard and says, "Jesus, that guy, your mentor, did a helluva job training you," and he smacks my ass again, adding, "Get your pussy up a little more," and I go up on my toes. He moves his soft cock under my ass, and it's just long enough that the head pokes the back of my scrotum. He rubs his dick across my buttocks a few times, firming it up enough to roll on a condom.
Then, with his left-hand flat on my back and his right hand guiding his semi-firm condom-covered penis, he humps the head in along with about an inch of the shaft, spreading my anus open about an inch and a half. That's the smallest insertion-opening since I've returned to bottoming, but going from a zero opening to that still hurts like a motherfucker, and I grunt, "Ooph!" He says, "Bend your knees a little," which I do while dropping down off my toes as well. Obviously, Jimmy is used to fucking shorter guys than me, but I don't mention how dumb it was to tell me to get my pussy up higher.
His cock is firming up quickly, and happily, I notice the initial pain of entry is already subsiding. I've been programmed to embrace the pain, but I don't personally mind when it's not much of an issue either. Now that he's got his cock inside my rectum about two inches and it's become a pretty hard boner, he humps the last three inches up inside me too. I go, "Ahh!" and then, "Umm." It feels good. The circumference of his dick isn't much, but all assholes will tighten around any size intrusions and grip the penis, or whatever is up there, pressing it against the prostate gland. That's a dandy pleasure-giving gland that millions of years of Nature's subtle changes finally settled on for no other reason I can think of except for us homos to enjoy.
Jimmy doesn't waste a lot of time and begins hard, fast thrusting right from the get-go. "Slap, slap, slap," sounds bounce around the room as sensations begin percolating from my rectum that quickly get me forgetting about the size of Jimmy's boner. Yes, bigger boners give greater pleasure, for me anyway, but this boner has all my attention right now, and I'm going, 'Ah, ah, ah," with every hard thrust, full five-inch thrusts that feel awesome. Plus, Jimmy is doing the thrusting with his skinner penis in the same manner, Gregory did it, meaning alternating the direction of his thrusting slightly, surprising me in a most pleasurable way as to where the head will bounce off my bowels next while exerting different amounts of pressure against my prostate and stretching my anus in different ways.
Whatever he's doing, it feels fantastic, and this is a damn good fuck. My cock is hard as nails up against my belly as I concentrate, visualizing even his five-inch spiky boner doing what Jimmy wants it to do. I'm going, "Oh, oh, oh... Jimmy, ah ah, feels good, Ummm..." and then my climax explodes from my nuts and up my boner and out into the world, I go, "Eeeeiii," sounding like a girl who just saw a mouse. My cum shoots straight up, up, up, then curves slightly to come down, splattering on the bureau top between my hands.
He thrust a half dozen more times before pulling out, mumbling to himself, "I almost blew my load." Like Gregory, Jimmy fucked an orgasm out of me without climaxing himself. They both are saving their cum to service their next client. I don't care because they get me off really well, and I've got the sizzling after effects buzzing around me right now to prove it. Oh man, that feels good!
Breathing deeply, Jimmy goes, "Okay, Tom? Did you get off pretty good there?" I exhale, mumbling, "Yep," and I turn around, then wrap my arms around him, momentarily pretending he's Bruce. He lets me hug him, hugging me back a little, murmuring, "All you need to do is get another date with me, and we'll do it all over again. Okay?" Getting myself together, I let go of him and says, "Yeah, of course. You and Gregory are excellent pussy boys, and I appreciate it."
He's getting dressed, mumbling, "So, six hundred dollars, and we're even." I go, "Oh, yeah, of course," and pick up my shorts to get my cash from a pocket. I give him $650, and he hands me back the fifty-dollar bill, saying, "The hundred buck is more than sufficient for a tip. I told you to wise up or guys, not me or Gregory, but most guys are gonna take advantage of you."
As he finishes getting dressed, he's like, "Um, Tom, we were wondering, Gregory and me, why you were trying to qualify to be a pussy boy if you're rich. Throwing money around, staying at the Waldorf, ya know?" I say, "I'm not rich. I'm having a blast spending the money I saved when I was in the service. I've got some left too, but not qualifying for a pussy boy job throws a wrench in my plans."
He pats my shoulder, saying, "It's been a pleasure, Tom. When your money runs out, I'll put a word in for you with my man, and maybe he'll take you on, although I've heard him say his mentoring days are behind him. Still, if Greg and I ask him nicely, maybe he'll mentor you the last three weeks of training you're missing. He's a tough motherfuck, though, so I'll warn you about that. Once we guys finally qualified to his standards, though, he treats us very well. You gotta make money for him for sure. He beats the boys who slack off."
At the door, I lean over. and kiss his cheek. He grins, mumbling, "You owe me twenty-five dollars for that," then laughs. After another little hand wave at me, he goes on his way. Closing the door, I sit on the sofa and smile because I'm getting back to feeling okay. It's cost a lot of money, but Greg and Jimmy have provided some good sex and intimacy that Bruce has programmed me to need. Rubbing my junk, I think back on the oral sex with Jimmy. Gawd, I liked doing that!
Well, it's almost ten-thirty, so Cowboy and Lee are probably out of the show they went to see. What would get me back to feeling almost as good as I feel when Bruce was mentoring me is if I could fuck Cowboy tonight. That would be perfect, but there's no realistic chance of that with Lee here.
I put on boxer shorts and a t-shirt and wait for the boys, but they're making a late-night of it, so I'm in bed before they come in. Later, basically sleeping, I hear them laughing, so they're alright.
I have a solid night's sleep, which only happens when I'm sexually satisfied. I get up and order coffee and a new toothbrush from room service. Peeking into the boy's bedroom, I see Cowboy deep asleep with his arms around Lee. Hmm, it's going to be hard for Cowboy to move on from Lee. Puppy love maybe, or, no, they're too old for that. Jesus, real love?
The craft of coffee and new electric toothbrush arrive, and I sign for it, tipping the older guy ten percent. They overcharged me forty bucks for the toothbrush, so ten percent was a damn nice tip for five minutes of work. Heh-heh, if he were that cute young kid from last night, the tip gets doubled.
The first thing is I give the new toothbrush a workout, then I shower, and around ten o'clock, the boys stagger out of their bedroom. Cowboy comes over and hugs me, kind of hanging on me, saying, "This is a wonderful summer, Zach. Thank you!" Then he kisses me, and I look at Lee, who grins and says, "My turn," and he does the same thing. Jeez, he's a skinny kid.
At eleven, we go to the brunch buffet deal the hotel offers, and the three of us eat enough to cover lunch. The boys are off to the Met, one of the world's finest and largest art museums, to look at the, um, art. I look up the address of the porn shops, Pleasure Chest, and Leather Man, then have the doorman flag down a taxi for me. I give the cabbie an address in the West Village.
After a fifteen-minute drive in heavy traffic, the taxi driver says, "I ain't going down that congested street. You can walk from here." Fine with me, I want to walk anyway. It's twenty-one dollars on the meter, so I pass a twenty-and-ten-dollar bill to him, and he says, "Thanks, pal," so no sense waiting for change. Getting out of the cab, I think I see a pussy boy right away. He's with three tough-looking women, two black ladies, and one white. The women all have way too much make-up on, and they're wearing skimpy clothing, one with hair the color of cotton candy.
A block further down, I see a sign for Pleasure Chest. That's all the sign says. Casually walking on the other side of the street, I saunter down past, which I think is a pussy boy to get a better look. He sort of has the right haircut, although, like Gregory, he's in bad need of a haircut. He's wearing a blue polo-type shirt with the collar up and khaki shorts, and he also has a fairly large nose ring which I find gross. So, he could be a pussy boy, or maybe not.
Slowly walking a block past that little group on the opposite side of the street, I don't know what to do next. I'm not sure I want to do anything. There are three teenage-looking boys with backpacks smoking cigarettes up ahead. I keep walking towards them without any hope they're pussy boys because they're the opposite of preppy. I just don't want them thinking I'm afraid to walk past them. It's my ego, ya know. Without looking at them, I walk past them, and when I'm ten feet by, one of them says, "You looking for a good time, or are you lost?"
I stop and turn around, "Who said that?" There must be something in the way I asked that has them all looking away. Going back to them, I say, "Do any of you guys know where the sweatshop is?" The blond boy with a green streak in his curly hair says, "Nope. You mean like kids working in China for a dollar a day, right?" I give him a hard look, then mumble, "If you know anything about a gay sweatshop, it's worth a hundred dollars." The older-looking kid says, "You a cop or something?" I go, "I'm something, but not a cop."
Walking back the way I came, one of them calls out, "Oh, I just remembered where the sweatshop is." I stop and turn around again, "Yeah, where is it?" It's blondie with a green streak in his hair. He goes, "Where's the hundred?" I go, "You get the hundred when you walk me to it." He goes, "I ain't walking anywhere with no fag," and all three giggle, turn around, and walk away from me.
I didn't think it'd be easy. Walking back past the women and the possible pussy boy, um, oh. He's gone now. It's just the three tough women. Tough broads; that's what they were called many years ago. Or, in the movies, at least.
Then, oh, there's the possible pussy boy leaning against the side of a check-cashing shop looking at me. I look at him, and he goes, 'Doncha got a car?" I go, "I came in a taxi, why?" He asks the obvious question, "Are you in law enforcement?" Shaking my head, I go, "No, are you?" He smirks, muttering, "Oh, sure," then asks, "What are you doing around here?" I say, "Looking for pussy boys. What are you doing around here?"
He's about as tall as me and thin, looking as if he's in his early twenties. Up close like this, he's not good-looking at all. Big nose and the ring in his big nose is through the side of his right nostril, about an inch in diameter, and it's lost a lot of its artificial gold color. He goes, "I can take you to a safe alley. You don't need a car." I shrug and go, "Why would we do that?" He says, "Don't fuck around, alright? You want some action; I'm here to accommodate. If you don't, hit the road."
I ask, "How far's the alley?" and he snorts out a laugh, saying, "You don't know shit, do ya?" I go, "Everyone tells me that," and he goes, "C'mon, I'll show you," and he grips the back of my neck. Ah-ha, a dead giveaway; he's a pussy boy.
He squeezes tightly, saying, "It's fifty bucks for a blowjob, or I can fuck you up against the wall really well for a hundred." The alley is a half block down from where he was standing, and it goes down a block, but he moves me to an alcove, saying, "Safe and snug in my office here." Now, I can't catch my breath because I realize I'm going to do this. A couple of recent fucks from pussy boys has me wanting more, plus this guy, assuming he knows what I'm looking for, is more likely to tell me where the sweatshop is if I first do business with him.
Letting go of my neck, he smiles, asking, "What's it gonna be, hotshot?" I try to say, "The fuck up against the wall, but it comes out, "Ah, um, ah, the wall." He nods, mumbling, "Good choice. Let me hold the hundred dollars, and we'll get to it." I swear, I'm in some kind of trance at the matter-of-fact way he is going about this bizarre experience. Bizarre to me but not to him; this is routine for him. I pull out a bill, but it's a fifty, so I pull another one out, and it's a hundred. He takes them both, smiling and saying, "Hey, you're alright, bro! Nice tip."
I nod and kind of grin. He twirls his finger, so I turn around facing the wall, and he pulls my shorts down past my hips and then my underpants, both to my knees. I turn my head looking back, and see him pulls his shorts down to just below his balls. He holds up his fat six-inch flaccid penis with the fingers of one hand and shows me a condom in his other hand, saying, "Stroke my johnson while I get this open." It was like a magic trick how he did everything in five seconds, and now here we are with our junk swinging in the breeze. He has no pubic hair, so I got myself a real live pussy boy after all.
Making a face, I'm like, "What?" He mutters, "I said stroke my dick to get it hard. Haven't you ever had sex before? We help each other out." Still, mostly facing the wall because I don't want him questioning me about my shaved pubes, I take his penis in my fingers as he quietly says, "There you go," and he rips open the condom packet while nodding his head at his cock, so I stroke it fast. He goes, "Nice fingers, nice and soft, so I'm guessing you don't do a lot of heavy lifting, huh?"' I go, "What?" He grins, and he has a very nice grin, then mutters, "Nothing, I didn't say nothing. Go ahead, keep stroking my little buddy there."
His dick firms up in twenty seconds, and he pushes my hand away, saying, "Both hands on the wall and stick your ass out." I do that, and he immediately feeds in the not quite hard head of his cock. That hurt with the lubricant squishing all around my anus. He does some two-inch thrusting, and I feel his cock getting harder and bigger. Then, POW, he shoves it in, all the way in, and I make a screeching sound, so he puts a hand over my mouth, leans against me, and moves only his hips driving his cock back and forth in my ass, "Slapslapslap," fast and very hard.
The pain soars and stays with me for a minute. I struggle a little, but he's as big as me, and he's leaning on me. It's a rough ride for a minute or so, and then the pleasure of having a cock pounding my rectum takes over, and I go, "Ooh, umm, yeah." Then I get very docile as I'm now totally dominated. He goes, "Keep your mouth shut, bro. We don't need company." Then he takes his hand off my mouth, grips my hips with both hands, and wildly slams his rock-hard fat six-inch boner too and fro in my ass.''
I cum quickly after he took his hand away from my mouth. It's a violent orgasm screaming out of my boner that's sticking straight out. A hard burning stream of cum that makes me dizzy with sexual pleasure. I slump against the wall, barely avoiding my large cum load that splattered on the wall and is beginning to drool down slowly. That's when I notice many cum shots and many drooling streams now dried except for one that's a little lower on the wall than mine. This guy must have had an earlier customer back here.
As soon as he saw me humping my climax out, he pulled his cock out and patted my ass, then pulled up my pants, again without unbuttoning my shorts. He goes, "Nice doing business with you. I'm Shawn, look for me next time. Thanks," and he walks quickly away. I'm still shuddering from that fantastic climax. My ass feeling gooey with lubricant, but my anus is still quivering, and my prostate is still ringing its bell a little.
Holy shit, I need to support myself against the wall, keeping away from the many cum shots on it. My body's calming down finally, and I step away, taking a deep breath, then another. What the hell was that? Well, it might be the hottest fuck anyone has ever laid on my ass; that's what that was. Good, God! It hurt like a motherfucker for a full minute and then was so fantastic the next ninety-second I blew one of the best orgasms of my life.
And, I never asked him about the sweatshop. Walking out of the alley, I realize it was the weirdness, the totally new aspect of that sex act added to its heat. And so did Shawn. He did everything his way, fast and hard, and then... thanks, bro, look for me next time, and he's on his way. Unkindly, I have another thought, and it's that Shawn is the least attractive guy I've ever had sex with. Out of the alley, I look for him but don't see him. He's not with the women of whom only two are left. I guess one of them got lucky.
My hand goes back to feel my ass. I don't feel any wetness from the lube soaking through, not yet anyway. Damn, though, I'm still jittery from that climax I had. Checking my cell phone, I see it's only ten after twelve. I've got four hours before Gregory is visiting again. Damn, where did Shawn get to? Ya know, I might come back tomorrow for another go at it with him. Nah, it wouldn't have the thrill factor now that I know what to expect; that was half the experience... the unknown, the suddenness.
I'm looking for a taxi and not seeing a single one. Four blocks away, I see Shawn, though. He's drinking a soda standing outside a small grocery store talking with another pussy boy. And that kid is definitely a pussy boy with a recent haircut, a white polo shirt, and tan khaki shorts. Shawn's back it to me, but the other pussy boy is staring at me, perhaps thinking, here comes his next customer. And, as I get closer, I see that this pussy boy isn't attractive either! I was under the impression one needed to be good-looking. That's unrealistic, though, now that I think about it. Most guys are average-looking, a small percentage are really homely-looking, and about the same small percentage are very good-looking and/or cute. Most are in the middle.
I walk right up to them and put my hand on Shawn's shoulder, saying, "Hey, stud. I didn't thank you for that exceptional fine two-and-a-half minutes." The other unattractive pussy boy goes, "Hell, Shawn usually only needs two minutes. You got an extra thirty seconds." Shawn snorts a laugh spitting out some soda, and goes, "You're welcome." Then to his buddy, he goes, "He's the handsome motherfucking stud I just told you about."
I go, "I'm desperate to find someone. A friend of mine who is, like you, a pussy boy. He was sent to one of the sweatshops, and I'd like very much to visit him. Can you help me out here? Do you have any idea where the sweatshop is?" The kid with Shawn has a biggish head and a big face with facial features spread out. His smallish eyes too far apart with big eyebrows, a small pointy nose, and an ass-chin under a wide mouth. He goes, "Dude, what the fuck you talking about. A sweatshop?" Shawn says, "No, Nicky, I heard something about that. A pussy boy farm out in Brooklyn somewhere. It's probably bullshit, though." Nodding, I pat Shawn's back again, "Thanks, and you fuck great!" Nicky goes, "Shawn's a legend."
Walking away, I feel a little optimistic because I've got a lead. As it turns out, I need to walk almost an hour to get back to the Waldorf, asking for directions three times. And, I hate asking for directions! Where are the fucking cabs? It wasn't all that bad, though, as I had plenty of time to reminisce about Shawn fucking me in that unbelievably hot manner. And Gregory's due in three hours... hot shit!
To be continued... donnymumford@outlook.com.
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