Summer of Sex with Cowboy

By Donny Mumford - Laureate Author

Published on Mar 11, 2022

Gay

MY SUMMER OF SEX WITH COWBOy

Chapter 44

By Donny Mumford

Sunday morning, Bruce's cell phone alarm wakes us at five o'clock. We moved apart while sleeping, so I slid over next to him, and he puts his arm around me, muttering, "Good morning." I go, "Good morning. Um, is waking up this early beginning to bother you?" He shakes his head, "Nah, I feel good about everything, Zach; I don't mind getting up this early. I don't mind waiting on tables either. I'm grateful to be living a real-life existence finally. I pinch myself to be sure it's not a dream... and it's not, it's really happening for me."

I'm like, "Wow, that's positive thinking." He shrugs, "Yeah, it's something I'm trying out... thinking positively. Well, it's another new morning, so here I go," and he slides out of bed and goes into the bathroom. I pull his pillow to my face inhaling his subtle scent, and doze off until... "Let's go, Zack!" My eyes pop open and see Bruce pulling the Cafe T-shirt over his head, adding, "It's five-thirty. If we leave in five minutes, I can be there before Anne opens the door."

Nodding, I get out of bed and stagger into the bathroom. After a much-needed morning piss, I wash quickly and brush my teeth. I'm dressed and in the kitchen just in time for Bruce to hand me a take-out cup of coffee, saying, "Let's get to it." We're quiet as I drive us through the deserted streets making good time to Atlantic City. Pulling up to the boardwalk ramp near the cafe, the sky just brightening with the sound of seagulls squawking over the beach, Bruce leans over and kisses me quickly on the lips, saying, "See you at three-thirty." He's out of the car before I can say anything. As he's jogging up the ramp, I go, "Have a great day, Bruce." He waves and goes around the corner on the boardwalk. Huh, he initiated the quick goodbye kiss... sweet!

I back the car up and then, for the first time this morning, think... 'Derick.' He hadn't entered my mind until right this second. When I'm with Bruce, he's all I think about. Now I'm wondering why the fuck I arranged to meet Derick this early? What was I thinking? Well, Derick made me horny, and I blurted out the time of six-fifteen. He's so 'effing sexy, plus I'm expecting he'll be one dominant motherfucker.

Damn, though, I'm still feeling good about sex with Bruce last night, and not especially horny. Well, this summer, it seems I'm always up for sex with the right young guy, and Derick certainly qualifies as the right young guy. Driving back the way I came, I soon see the run-down motel Derick is staying at; it's coming up on my right. There are cars parked in front of most rooms, so it can't be as run-down inside as the exterior.

Hmm, he said room 21. There's a fairly old Volkswagon parked in front of room 21. Someone who is fat with cash, as Derick claims he is, would have a better car. And that someone would stay in a better motel as well. There's a good chance Derick isn't completely honest with me about his financial situation, not that it matters all that much. It matters to the degree that he needs my business, which gives me a little leverage about how things will proceed.

The closest spot I can park is three down from room 21. Putting the top up, I get out and lock the car. Yeah, now I'm feeling empowered to insist we skip the paddling. I'll pay him the $50 for it, though, which is what he really cares about, right? Walking up to the door for room 21, I'm beginning to feel an exciting sense of anticipation. He is a hot little dude, so yeah, I'm excited to experience a new dominant pussy boy.

Knocking on the door, the anticipation builds, making me grin to myself. Goddamn, I like sex! Derick opens the door and nods at me with a neutral expression on his face. He also has a toothbrush in his mouth which he takes out, saying, "Good start... you're right on time. Come in but do not speak unless I ask you something." Shrugging, I saunter inside a rather small room that's neat as a pin and appears to be freshly painted. Bruce's dumpy apartment was always super-neat too.

Closing the door behind me, he says, "Get undressed and neatly fold your clothes on that chair," as he points to the only chair in here. Leaving the door to the bathroom open, he finishes brushing his teeth. Interesting that he's wearing only bikini-type underpants. His cock and balls seriously bulging out the front, barely being contained inside the silky material. Huh, bikini bathing suit yesterday and bikini underwear this morning... sexy.

In thirty seconds, I'm standing here naked, my clothes on the chair as I watch him rinsing out after brushing. Wow, what a hot little body on this guy, totally hairless except for the very short blond hair on his head. He comes into the bedroom, his shockingly blue eyes showing intensity as he says, "Stand up straight." I do that, and he adds, "I should have thought of this yesterday on the beach. Um, well, you've already experienced pussy boy recruit training, so you'll recognize some of the techniques I use when servicing extra submissive clients like you. That makes for an unusual situation, and I need to ask you before accepting your money if you're willing to proceed knowing what I just told you about my tactics? Also, once we start, the money is non-refundable."

Hmm, recruit bullshit again. On the other hand, Bruce is still doing a bit of pussy boy recruit stuff, and, anyway, I can agree to go along with Derick's dominant act, but if I don't like something, no problem. I'll tie his dick in a knot and leave.

Nodding, I go, "Yes, I want to feel your dominant sex, Derick. That's the reason I'm hiring you." He mumbles, "Huh, why doesn't that surprise me? As a super-submissive, you probably had a hard-on through most of the pussy boy training, getting off on it" I go, "Nah, it was too stupid for..." but he holds up his hands, muttering, "No talking, just give me four hundred dollars." I get the money from my shorts as he tells me, "The other hundred you'll want to give me as a tip when we're done."

He casually tosses the four hundred dollar bills on the newish-looking bureau and turns around, saying, " Okay, you're under my control until I excuse you, or until you won't do what you're told. That will end my escort service today, and we'll go our separate ways. This is how we do it in Delaware and how I'll teach my recruits to service clients."

He looks at me blankly, asking, "Any questions?" I go, "Um, would it be alright if we started later today. Um, say if I came back at, um, ten o'clock?" He keeps giving me his cute dead eye expression, so I go, "I don't know why I suggested six-fifteen, haha, ya know... it's so early." Derick goes, "Is that all?" Shrugging, I mutter, "Um, the other thing is, do you absolutely need to do the paddling? I'll pay you for it, but I don't wanna..."

Fuck, now he's staring into my eyes with a disgusted expression on his face, so I stop in midsentence and look down mumbling, "No, I guess you know best." He says, "Stop this ridiculousness immediately! You picked the time, and I told you on the beach the paddling was mandatory, plus I have your non-refundable payment." Frowning, I nod, mumbling, "Yeah, okay, you're right. I was the one who said six-fifteen, not you. It could have been later, but the paddling, um, yeah you did say..." Derick mutters, "Please, shut the fuck up..."

As I said, I'm not especially horny because Bruce's sex on my body last night is still in my mind, but Derick has my attention now. He has his arms folded across his chest, looking smug, comfortable, and confident. Well, I get off on being dominated by little tough motherfuckers like Derick, and he's too hot to pass up, so I mumble, "Sorry, I apologize for speaking out of line. I'm ready."

He makes a face looking up, like...oh, brother! Then he opens the bottom bureau drawer and takes out an identical paddle to the one Bruce used on me, saying, "Bend over with your hands on your knees." Fuck, I haven't gotten off to a very good start, so I better do what he says. I bend over with my hands on my knees and when he swings the paddle, it makes a "Swoosh" sound just like Bruce's paddle. A "WHACK sound follows as the wooden paddle connects with my buttocks, leaving them quivering and stinging. My jaws clenched as another "Swoosh, WHACK!" and another, "Swoosh WHACK!" and another, "Swoosh, WHACK!" I go, "Ow, ow, okay, please stop." "Swoosh, WHACK!" Then he says, "Walk it off on your hands and knees."

That hurt, yeah, but it wasn't as bad as the way Bruce paddled me. Dropping to all fours, I walk around this small room on my hands and knees as fast as I can. Derick sits on the edge of the bed with the paddle on his lap. I go twice around the room, and he says, "That's enough." When I stop, he says in a nice quiet voice, "Come over here now, and get in between my legs." I do that, and he murmurs, "Liftoff your hands." When I straight up on my knees, he hugs my head, my face against his bare hairless chest. Oh, man, this feels nice, and he smells nice too. He rubs my head and soothingly says, "Shh, no more paddling for now. You're okay; you're not injured. I didn't hurt you much."

The contrast between this and being paddled makes my eyes water, and he goes, "Go ahead, let it out." I lean against him, my arms around him feeling like a child, which is exactly the way I felt when Jon gave me the unwanted pussy boy haircut that time. Derick does more light rubbing on my head, his arms around the back of my neck. This is totally unexpected; then, a few of my tears begin running down his bare chest. I'm not crying, far from it 'cause I like this, but my eyes are watering.

He gets a tissue from somewhere and holds it at my nose, saying, "Blow your nose, Zach." Really? What the fuck? It's silly, but I do that, and he quietly says, "Now, stand up and go over there to stand in that corner near the door while I get a few things I'll need." I say, "Yes, Derick," only now realizing I am in a damn good submissive trance, one that makes me shiver as I press my nose in the corner of the walls. Derick's Delaware technique as a pussy boy escort is pretty fucking interesting. The paddling followed by his compassionate hugging, me in an inferior position on my knees created this submissive trance I'm in.

Yeah, but understanding how he got me this way doesn't lessen my submissive frame of mind toward him. There's nothing original about standing in a corner, but it feels different. By now, I know it's some kind of phycological bullshit fucking with my mind, and they all use it. And, why aren't I embracing this rather delicious submissiveness? Well, it's too soon, that's why. It took less than a minute to paddle me, and I've been standing here for thirty seconds. Yeah, that, plus the fact he was upfront about recruit tactics used on submissive guys like me and then giving me an out before I paid him... that wasn't dominant at all. I'm not used to pussy boys being fair.

On the other hand, I kinda like this so far and... and then I jump when I feel Derick's hand on my shoulder. He goes, "Relax; this is just a dog collar. A small thing that'll help you stay in a submissive frame of mind." and he fastens it around my neck, but not too tightly. He says, "Keep your nose against the corner of the walls while I give you a massage. It's a bonus I do only for special street clients. Usually, massages are reserved for those hiring me online." I'm totally fascinated by this guy. He's very different from other pussy boys I've hired.

His hands are strong, not that I'm surprised by that because, while smallish, he looked strong on the beach. His gripping and releasing tenons or whatever in my shoulders is almost painful yet feels really good. He says, "I do my massages while my client is standing in a corner so they can concentrate on how it feels without distractions. Arms at your sides now."

He massages down my arms, gripping my hands, then reaches around me to massage my chest, always gripping just barely this side of pain, leaving each area tingling and feeling really good. Massaging down my stomach makes me gasps, then his hands grope my cock and all around my groin until my cock is a steel rod up against my belly. He gently squeezes my testicles, lifting them, then he drops them, and his hands move over to my thighs on top, then the side gripping and releasing, squeezing and rubbing tightly. His hands work their way around to my buttocks, and, Omigod, my cock throbs as Derick's hands go under my ass, pulling skin backward and letting go. My whole body feels alive.

When he stops, I'm tingling all over as I hear, "Swoosh" then "WHACK," and I screech out, then "Swoosh, WHACK! Swoosh WHACK!" and, dropping the paddle, Derick's arms are around me as he's quietly saying, "If you scream out like that again, I'll put a ball gag on you. Do you understand?" I nod, "Yes, Derick." He says, "Okay, this is going very well. You can turn around now, and we'll do the two-minute makeout you've paid for." My buttocks are vibrating and sore, but I don't mind. I want to please Derick by not complaining.

He takes my hand, gently saying, "Come with me," and I again realize I'm acting extremely submissive. I stare at him, impressed by his technique even as my butt cheeks are burning and stinging. Still holding my hands, he grins as he gets on the bed he made up himself. Then, lying on his back, he says, "This fifty bucks I should be paying you, Zach. You're the best-looking client I've ever had." Pulling on my hand, he goes, "Don't be shy, get on the bed, I won't paddle you here." Fuck, I am acting shy as I crawl on the bed. He lets go of my hand to hug his arms around the back of my neck, murmuring, "C'mon, you know how to make out, don't you?"

Pulling me down to lie on him, he says, "Oh, you're a big boy. You'd better lie on your side facing me." It'd be easier to do if he'd let go of my neck, but he doesn't. When I'm lying on my side, my boner throbs, and I have that feeling of being hypnotized. Staring into my eyes, he murmurs, "Pretend we're lovers," and his fingers touch my lips as he murmurs, "Open your mouth slightly. There that's good." He leans over and covers my lips with his, his tongue sliding on my tongue, his hand lightly rubbing the back of my head as his other hand is now cupping my balls. I'm partially afraid he'll squeeze my nuts and partially aroused by his sexy making out as I kiss back, closing my eyes, my cock continuing its throbbing.

His minty-tasting saliva mixes with mine, and I moan, "Mmmm," as Derick almost devours my mouth. This is a fantastic make-out, the kind I want to have with Bruce, but in my sexual submissiveness, at the moment, I feel privileged to be doing this with Derick. His hand on my balls gets slightly tighter, ever so slightly tighter, and then tighter still as I feel my climax building and building, his mouth and mine almost one now and then I squeal into his mouth as my hips hump, and I blow my load up my stomach and chest. Another spurt of cum, and Derick backs away, saying, "Oops, wow! You are a sexual creature, aren't you?"

I'm in a daze, shuddering at the after-effects of that unexpected climax. Derick slides down to get off the foot of the bed, saying, "Off the bed, bend over with your hands on your knees again." I'm shaking with sexual arousal, cum drooling down my chest and stomach. Without hesitating, I scramble off the bed and bend over with my hands on my knees. He smacks my ass with his hand, saying, "Good, you're totally compliant now," and he gives my ass another casual smack with his hand, saying, "Stand up." I do that, and he retakes hold of my hand, mumbling, "Come with me."

Leading me into the small bathroom where, still holding hands with me, he turns on the sink spigot and wets a paper towel, then cleans the cum off my chest and stomach, quietly saying, "I expect a perfect blowjob after I've cleaned you up." I mutter, "Yes, Derick." I'm feeling fantastically submissive to him and loving this very different experience. The dog collar is fine, and my ass is fine too. He doesn't paddle as hard as Bruce did.

Ya know, I'll bet I'd like being Derick's recruit, but then I thought the same thing about being Jon's recruit. And, fuck, under many different circumstances, I think I could actually be a successful pussy boy for any of these three mentors, Derick, Jon, and/or Bruce. Of course, Bruce!

Derick's still holding hands with me, leading me back to the bed, saying, "In fact, I'm so impressed with you as a perfect client, one I'm sure will tip me handsomely when we're done today, I'm going to allow you, without extra charge, to lick my feet and my body as a prelude to sucking my big cock. Whaddaya think about that?" I nod my head too fast for too long, saying, "Thank you, Derick..." Hmm, I'm into this submissiveness perhaps too deeply to think straight.

He lets go of my hand and gets on the bed again. Then says, "C'mon up here and get on your knees. I do that and he mumbles, "Go ahead, pull down my underpants." On my knees gulping and licking my lip, I get my forefingers inside the waistband at each side of his tiny underpants and slowly pull them down. The bikini underwear slides down, and I keep pulling it down his legs and over and off his feet. His big cock and big balls lie there, waiting for me. Of course, they're perfectly hairless. They're also slightly damp and sticky-looking after being encased in the silky material overnight, or more likely since he took a shower yesterday after coming off the beach.

His cock isn't as long as Bruce's cock, but it's a lot fatter. Well, on second thought, it is almost seven inches, but its bigger heft fools the eye about its length. He motions for me to kneel between his legs, then puts a hand behind my head and gently moves it forward until my face is squished against his sex organ, my hands on the bed on either side of him. There's a slight musty scent to go with the pleasant scent I noticed when he hugged my head against his chest, comforting me after the first paddling.

I lick the shaft of his cock, and he says, "Not yet. This was a tease. First, start with my feet. Give them a good licking and work your way up one leg and then the other before you get to suck my cock and balls. I want to feel shivers of pleasure too." "Yes, Derick."

Going backward on my knees to below his feet, I lean down and lick up the sole of his left foot and suck on his toes, getting my tongue between a few of them. Lifting his foot, I suck on the heel and lose myself in a deep submissive trance, licking and sucking on his left foot and leg, now losing all track of time, saliva drooling down my chin as I lick, lick, lick his feet and leg. Lick up his leg so far the side of his scrotum is against my cheek. I'd probably never stop licking this leg, but then he murmurs, "Now my right leg and foot." I'm in a fabulous submissive frame of mind licking and sucking his other foot and leg until he says, "Okay, now you can lick and suck my cock and balls," I have no idea how long I've been doing this and can barely remember who I'm doing it for.

That's not to say I haven't enjoyed every second of it because my cock is another roaring boner, this one sticking straight out as hard as stone. I lick up his fat cock from the big mushroom head to the root, then pick it up and suck the head into my mouth. I'm licking and slurping on his cock for I don't know how long, but it's become a fat wooden dowel by now, and it's sticking straight up as I leave it there and get to sucking on his balls. He's been groaning and squirming on the bed, his hands on my head, for quite a while. Finally, precum drools out the big piss slit, and he pushes my head away, grunting, "That's good. You've gotten way more than your fifty dollars worth. Stop!"

I'm panting, my head only inches from his saliva-saturated boner and balls. He says, "Off the bed, hands on your knees." I don't even know how I got here, but I'm standing next to the bed bent over and, "Swoosh, WHACK!" That felt good! "Swoosh, WHACK!" So did that! I'm actually disappointed it was just two paddles this time. By now, Derick is doing a little panting himself as he rubs my back, mumbling, "Good, you're doing good. Did you like licking and sucking my body?" Still bent over with my hands on my knees, I say, "Yes, Derick." He goes, "Did you get your money's worth?" "Yes, Derick." He pats my ass, mumbling, "Well, don't forget the tip then."

He takes a deep breath and goes, "Wow, you're quite a workout. Stand up and walk around a little bit." I do that feeling really, really sexually hot and aroused. Derick's cock is still fairly hard as he squeezes it, muttering, "Fuck, you almost had me blowing my load, and I'm the 'effing pussy boy, not the client." That wasn't a question, so I didn't say anything as I walk in circles around this small room.

Derick takes another deep breath, then takes my clothes off the chair, puts them on the small table, and sits down, saying, "Come over here." When I do that, he says, "On your knees between my legs like before." I do that, and, like earlier, he hugs my face against his chest, murmuring, "Just relax." Lightly rubbing my head, he quietly asks, "Are you thinking you'll nap with me after I fuck your brains out?" I murmur, my lips moving against his left nipple, "Yes, Derick." Rubbing my head some more, he goes, "I thought you might. I also thought you'd be an interesting client, and you sure haven't let me down on that score."

Without realizing it, my arms are around his waist as I totally relax, leaning against his smallish but tight body. He rubs my shoulders, asking, "Are you glad now that I insisted on the paddling?" I murmur, "Yes, definitely, Derick. That feels really good... I like everything you're doing." He mumbles, "Yeah, well, I make sure to never bruise clients' butt cheeks when paddling them because they may have, as you do, a boyfriend who would ask questions. It's a balance not to overdo it, but do enough, cause enough pain that the difference between pain and pleasure emphasizes the pleasure." It sure as shit works for me, but that wasn't a question, so again, I say nothing.

Wow, this feels so nice as he continues lightly rubbing my head, shoulders, and back. I know he's stalling after almost climaxing. Hell, I would have climaxed while licking and sucking his hot body if I hadn't blown off during our fantastic make-out. So, we're both recharging, getting ready for the grand finale. Grand finale for this morning anyway. He asks, "Would you like me to do you bareback?" I say, "Yes, Derick." He adds, "I rarely do that, but you've turned out to be a special and unique client, one who's had pussy boy recruit training, so I know you're clean. I get tested monthly anyway, not that I'm worried about catching something from you." No question in there, so no reply from me.

Sounding reinvigorated, he says, "Okay, here we go. Suck another good boner on me." He takes his hands off me, and I hunch down, pick up his almost flaccid cock and suck on the head, then cover my teeth with my lips and bob up and down, up and down. Christ, I love doing this! Quickly, his cock gets hard again, so I lap his nuts and then inside his thighs, then up and all around his hairless groin until he goes, "Good, that's perfect," pushing my head away.

He gets up, mumbling, "Hands and knees again," and as I do that, he goes into the bathroom, returning with a container of lubricant. As he pushes lube inside my ass and on my anus, he says, "You're so much taller than me, but on your hands and knees, we're a good fit for fucking. You're the client, though, so do you have a preferred way of getting fucked?" I'm woozy in my submissive trance, murmuring, "No, Derick. You're the boss." He mumbles, "Spoken like a true submissive," and he smacks my ass, getting lube on my right butt cheek.

Contentedly on my hands and knees, I hear the container of lube being dropped on the small table my clothes are on, then I feel his lubed hand on my hip and then the head of his boner against my anus. He doesn't thrust it in, though. He exerts pressure to slowly open me up little by little until, and there's a lot of opening necessary so it takes a minute or so, then "Ahhh!" it slides super-tightly in past my sphincter muscle. And, yes, of course, it hurts to be this wide open, but I'm embracing the pain because it aches so good. Derick's boner has a circumference, I'm guessing, of five and a half inches, so, from a tightly closed anus to one opened up to over five inches... yeah, that will always cause pain. I'm picturing his boner in my ass, and that thrills me, and the thrills continue as he slowly pushes that fat boner inside my rectum, almost seven inches of it.

When it's all the way in, Derick goes, "Ahh, umm," and leans against my buttocks as he rubs my shoulders, mumbling, "Your body is turning me on." I'm assuming he says that to all his clients because he said it in a kind of rote-like voice. I moan, "Mmmm, feels really good." He humps against me, his hands going back to gripping my hips as he says, "I'm not expecting this to last very long, so after I fuck a climax out of you, I want you to stay on your hands and knees for your last paddling of this date. It will help you maintain a good submissive feeling even though we'll be done with this particular escort date." I say, "Yes, Derick, but I definitely want to stay with you for seconds." He goes, "I thought you would, but we'll discuss that when we're through with this one."

It already feels pretty amazingly good, and I can't ever remember a bigger boner in my ass. Yep, Derick's hard fat cock is feeling mighty fine! Not even Richard's huge cock felt this good. Pussy boys with big cocks must make out really well with their whoring, and be as youthfully cute as Derick too... damn!

Tightening his grip on my hips, he moves his big boner back and forth three or four inches and keeps doing it, getting my prostate involved. He's also getting the walls of my rectum used to this big intrusion. The pain lingers, but I pay no attention to it as I can tell I'm in the hands of someone who knows how to fuck an ass awesomely.

He does one long pull back, the swollen head getting caught at the tight lips of my asshole, then he pushes it all the way in, and I go, "Ooooh, umm..." He does the same thing three more times before doing it three times at a different angle and I go, "Ahhh, ooh, ooh, ooh that feels good..." Then, he starts fucking my ass steadily, but not hard enough that his crotch is slapping against my buttocks. Just steady thrusting activating every nerve ending in my rectum, my prostate humming with pleasure, and the stretched lips of my asshole begin getting that stretched itchy feeling that Derick's fast-moving cock scratches all the way in and all the way out.

Long steady, smooth thrust after thrust with me moaning in ecstasy, my head back as I sway to and fro on my hands and knees. Three, then four minutes with sensations spreading out all over me, and then Derick grunts, and his hips begin humping much harder, and now I hear the slapping sounds as he's really got a hard, steady rhythm going, "Slap, slap, slap," and "Ahh, ahh, ahh... ohh! Derick..." This is a pleasure to go to war with. And then my climax sneaks up on me, and the anticipation of an epic climax is at the tipping point but then dies there as Derick stops thrusting, leaving his huge boner impaling me. He rubs his hands on my back, going, "Shh, easy, take it easy... let it last."

I'm gasping, needing to get over the top and blow this load of cum that's tantalizingly close to exploding. He sees me settling down so he murmurs, "That's my boy, easy does it. I'll get you there," and finally, the sense I'm going to climax drifts down to sort of idling and purring. It's maybe thirty seconds more before Derick starts his engine moving his hips again, doing that slow thrusting before picking up the pace as I gasp out, "Derick... ahh, ahh, oooh..." and he's full speed ahead again, "Slap, slap slap," and me, "Ooh, ooh oooh!" and in two minutes I blow my load with worlds colliding. I'm shuddering and shaking as he's holding onto my hips, still thrusting. I shoot off a short follow-up shot of cum, thinking my balls burst in their sack. Now, he's almost on my back humping once hard, and I feel his sharp stream of cum hit inside like a stick poked me. He gasps and groans, then he pulls his cock out and says conversationally, "Goddamn, that was good."

My forehead drops to the back of my hands as Derick casually mumbles, "Push your ass up. Get it up high for your paddling. I need to do this before all that cum starts drooling out." I push my ass up so high I go up on my toes 'cause I want to feel this paddling. Immediately, I hear, "Swoosh," and "WHACK!" I grunt, "Ow!" Two more Swoosh-WHACK! Swoosh-WHACK!" "Ow, ow." and then he cheerfully says, "That's all folks," and he chuckles while wiping the paddle with tissues, then putting it back in the bottom drawer of the bureau. My buttocks are hot and stinging, but they feel really good too, as I do as well. Cum did drool out and splattered when the paddle smacked my ass hard. Derick put extra effort into those last three whacks with the paddle and my buttocks are burning hot, stinging like crazy, and sinking me deep into submission. Excellent!

Holy shit, what an awesome date this has been! He says, "Stay like that as long as you want. I gave you some extra hard paddling so take your time recovering. When you're ready, we'll clean up and talk money again. Take your dog collar off too. As it turns out, you didn't need it. You got submissive from anything I did or said!"

I stay like this until my buttocks stop quivering, Derick's cum drooling down the back of both legs and under to the back of my nuts. Messy. The pain added tremendously to the pleasure; a delicious combination the way Derick does it. Then the superb fucking he gave my ass. He's special and I think he'll do much better mentoring than Jon. He's probably better than Bruce too, but I'm not in love with Derick, and Bruce is no longer a mentor, so who is a better mentor is a moot point.

Sighing, I get up, rub my butt cheeks, getting his cum on my hands. Haha, what was I thinking? Taking off the dog collar, I'm smiling at myself because that was a special experience. I get a hundred-dollar bill from my shorts, then join Derick in the smallish bathroom. He's just now pulling back the shower curtain and stepping out of the tub after a three-minute shower, saying, "Take a quick shower to wash all that cum off your ass and legs." "Yes, Derick," and I put the tip next to the sink.

He left the water on and as I step in under the flow, he says, "Showering is required if you're serious about having a nap with me, and then a second date." I mumble, "Yes, Derick. Um, this was a special date, really excellent." I'm still full of submissive vibrations toward him. He mumbles, "Right, whatever," and I mutter, "There's your tip on the vanity. I had a fabulous time. You're the best pussy boy I've hired, um, by far."

I see him pick up the hundred-dollar bill, saying, "Yeah, thanks. Glad you enjoyed yourself. That is my job, after all. By the way, how many pussy boys have you hired?" I say, "Six or seven different ones." Finished drying, he goes, "How was Jon Scheyer?" I say, 'Very dominant, but he lacks your, um, compassion to go with your seemingly natural dominance." He chuckles, "Natural, huh? You should see my act with a dominant client. It's a very different thing. Submissive clients like you are kinda fun, or as fun as whoring ever gets, anyway."

To wash, I'm using the only washcloth here, the one Derick used. I wash under the shower flow feeling fantastic. I'm thinking that after our second date, later on, I'll bet sex bedtime sex with Bruce will last at least five minutes. I desperately want our sex to be more memorable, and two-minute sex acts aren't especially memorable. Well, with Bruce, all our sex is memorable, but I want our sex to be so sexy-hot and special, lasting a long time, that he'll want to do it more often.

Satisfied I'm clean enough to nap with Derick, I use his damp towel to dry off the best I can. One towel and one washcloth? What a cheap joint this place is!

In the bedroom, Derick is dressed, and I notice the five hundred dollars has been put away. He says, "It's been a pleasure servicing your sexual needs, Zach. I appreciate your business. Just to review, if you want the nap with me and an abbreviated second date, I'll need two hundred dollars plus an extra hundred for the together-nap which includes a kiss before and after napping." Wow, what a bargain!

I've got my underwear and cargo shorts on, so I pull out my money and get a hundred dollar bill, plus four fifties, and hand the money to Derick, murmuring, "Thanks for letting me have seconds. I want to tell you again; you're awesome." He puts the money in his pocket, nodding his head, "Thanks, I'm happy you can afford me. Before napping, would you care to join me for breakfast?" I'm like, "Oh, sure, Derick. Thanks for inviting me."

He grins, "You're still experiencing heavy submissive vibes, aren't you?" I nod, and he mumbles, "That's remarkable. Jesus, you're really something." I can't stop staring at him. When I stare at Bruce like this, he tells me I'm making him uncomfortable. Derick just acts confidently smug, but then I've given him $800, so he doesn't care if I stare at him or not.

We walk out of the room, and he points at his shitbox car, mumbling, "Get in." When he told me to get in, I didn't give a thought to saying I'll be glad to drive my, um, slightly better car. The passenger door sticks, so I yank on it, and it makes a cracking sound, but it opens, and I get in. To Derick's credit, he doesn't feel the need to apologize for his piece-of-shit car. As he drives us out of the motel area, he asks, "How old are you, Zach?" I tell him the truth, and he says, "Yeah? Seriously? You look a lot younger. What makes you so submissive, though? I mean, you're hot with a tough body and good looks; what's up with your submissive nature? Um, was it some kind of childhood experience, or what?"

That's a good question, although I don't know the answer. I go, "Jeez, I don't know, but I first recognized my tendency for submissiveness at prep school. As a kid, I never called it submissiveness, though; I simply realized I loved being the bottom boy, and the more dominant my top was, the more I loved it. That continued during my college days, and then, because of a guy I idolized for years, I submerged my submissive tendencies and convinced myself I was an exclusive bad-ass top. Ha, then, after that, I wondered why sex was ho-hum for me... like I could take it or leave it." Derick goes, "It's amazing what we can convince ourselves of even though somewhere in our minds we know it's bullshit." Huh, I wonder what lies Derick's had to convince himself about? Whoring is a good way of life, would be a good guess for a lie he tells himself.

Not mentioning that I mutter, "Yeah, who knows how our subconscious minds are fucking us up?" Yeah, who knows, but it occurs to me that, actually, I don't want to change. And, I can't change anyway because Bruce will always be the dominant boss in our relationship. That's a given. Plus, I want our relationship to go on for years and years, so that leaves me in the submissive role, which I like anyway. God forbid, but if Bruce never loves me, I'll still prefer my submissive role when having sex with him... or having it with somebody. In everyday life, though, I'm not what anyone would consider submissive. Other than when having sex, I'm only submissive with Bruce, and I'm sure he assumes it should be that way.

Derick drives us to a local Pancake House, a good chain restaurant I've eaten at ten times at least. He orders a big breakfast for both of us, telling me, "My treat, Zach." Most guys would be offended if someone orders for them in a restaurant. Derick never hesitated, telling the waitress, "We'll both have number 12, with a side of home fries, coffee, and the large orange juice." She leaves, and he tells me, "Ya know, you are an extraordinary client. One of my all-time favorites, and I kind of thought you would be too. You enjoy yourself so much it makes it enjoyable for your hired sex partner."

I'm like, "Thank you, Derick. To be honest, most pussy boys I've hired can't compare with you, so my enthusiasm probably wasn't as noticeable to them. Don't get me wrong, they were all pretty good, or most of them anyway. And, ya know, before ten weeks ago, I'd never hired a, um, pro before." He nods, "Uh-huh, let me ask you... would you consider being my recruit and finishing your pussy boy training under my mentoring?" Puffing my cheeks out, then exhaling slowly, I go, "The thought of doing that makes my dick hard because, under different circumstances, I couldn't resist being your recruit or your prostitute on the street. That's honest to God true, but my circumstances are what they are, so I couldn't possibly do it."

He says, "I believe you'd flourish as my recruit, but what circumstances are you talking about? Maybe I can change them. Just so you know, I intend to continue sexually servicing my boys, rewarding them for a job well done even as they're making money for both of us." The waitress brings our coffees and orange juices. When she leaves, I say, "You're fantastic, Derick, but I'm in love with Bruce Dunlop, plus I'm the beneficiary of a large trust fund, so I don't need to make money." He goes, "Damn, you'd be great on the street."

When breakfast is served, we eat without talking, me staring at Derick getting excited to sleep with him. And, I'm definitely hiring him for tomorrow. Maybe I can use Derick in weaning myself off multiple sex acts by eliminating the nap with him and the follow-up date in a week or two. You know, be satisfied with one fuck before Bruce and I have our bedtime sex. It's good to have a solid plan, but is it actually solid?

As he drops a fifty-dollar bill on the table after breakfast, I ask, "Um, can I hire you every day this coming week?" He gets up from the table, saying, "You'll need to ask each day because if I get a recruit, I may not be available." Nodding, I mutter, "Yes, Derick," realizing I still have a submissive vibe going for him. Well, it's an ongoing sex date so, of course, I'm submissive to him.

Getting in his shit-box car, I'm like, "Derick, can I have a date Monday, um, tomorrow?" He nods, "Yes, same time and same everything, but ya better tip me well after our nap and seconds today." I say, "Of course, I will, and thank you!"

Damn, I feel so good! What great luck hooking up with Derick! If I wasn't in love with Bruce, I could fall totally under Derick's spell, and I'd probably end up whoring for him and to hell with my trust fund. There's something so intriguing about Derick being my main pussy-boy-man, working for him, trying to impress him so he'd praise me and give me the complimentary sexual attention. Oh, Christ, that is so sick of me, but there it is anyhow... haha.

Back in the motel room, we get naked, then do our stuff in the bathroom. Derick insisting I use his toothbrush, and, surprisingly, I didn't mind, then we got in bed, and he gave me more of a lovers-type kiss than I ever got from Bruce. He snuggles with me the same way every pussy boy I've slept with snuggles, and, with a boner tight up against my belly; I fall asleep. Well, I did get up at five o'clock this morning.

Derick nudges me, saying, "Time to get up, Zach." My eyes open, and he gives me another perfect kiss, then says, "Out of bed and get your hands on your knees for your first paddling." We're off and running. All the paddlings feel so good this time, and so does the standing in the corner, our making-out, the delicious oral sex on Derick's body, more paddling, and then another spectacular fuck with Derick outdoing the first one he laid on my spanked ass. The final paddling is hard and goes for five paddles with me yelping but feeling fabulously submissive and perfectly fucked.

In the bathroom, I use the same washcloth to wash my spanked ass and the back of my legs. There wasn't as much of Derick's cum to deal with this time but what a great climax I had! I tip him a hundred and fifty dollars, and he excuses me by sending me on my way at eleven-thirty saying, "Six-fifteen, Monday. Be on time!" I thank him for everything for the tenth time and walk out, rubbing my buttocks, feeling very submissive and fantastic! I can't remember the last time I've felt this good.

Driving back to the apartment to get into my swimsuit, I find the boys, Cowboy and Lee, ready to leave for New York. I'm in a great mood hugging and kissing them goodbye. Cowboy chuckles, saying, "Wow, you're in a great mood, but we said goodbye last night." I go, "Yeah, I know, with Bruce and me after dinner. You were supposed to leave first thing this morning, though."

Lee snickers and says, "I needed to do Cowboy up right before we left, which took a while, and then he wanted seconds." That sounds familiar, haha. I mutter, "You two have turned into sex fiends," as if I'm not one too. When the limo Cowboy hired to drive then to New York shows up, I go down with them to see them off. Cowboy says, "We'll be back probably Friday, Zach," and he kisses me again. I watch them drive away, missing them both already. We don't do a lot together, but just knowing I'll see them every day, having dinner together most nights, is something I'll miss.

I'm still feeling fabulous while driving back to Atlantic City wearing the bathing suit, a polo pullover, and sandals. There's not a touch of horniness in me and I'm not even thinking about sex with anyone. Hell, I could be with Bruce, and I wouldn't think about sex, which would be the first time that's ever happened. He'd like that. Take the pressure off him.

At the rental booth, I give an extra cheerful hello to Markie and then a hug lifting him off the sand when he brings the chair and umbrella around to the front of the counter. He goes, "Ah, you've still got a crush on me, I see." I go, "Yes, I do 'cause you're a hot little dude. I wish I were younger, so I could give your boyfriend a run for his money." He gets the umbrella on his slim shoulder, muttering, "You'd need to be a helluva lot younger. What are you, about twenty-three or four?" I go, "Something like that."

When he's got the umbrella set up, I go in my pocket and find I don't have anything smaller than a fifty, so I give him that. He looks at it, then says, "Seriously? I can't accept this, Zach." Ha, that's the second time he's said my name. I go, "It'll be for tomorrow's tip too, okay? I don't have a smaller bill." He nods, mumbling, "I really like you, thank you," and off he goes trudging up the sand.

Being a trust fund guy, I've never respected money. I'm kind of revolting like that, but, whaddya gonna do? Wow, though, I haven't felt this good since... since ever. Derick was perfect, just what I needed, and, sure, it was absurdly expensive, ridiculously so, but do I care? HA!

It's not long before I'm lonely. I'm totally sexually satisfied, but I like having company... being with someone. I hate being on my own! The few people I know in this town are either working or going to New York City. As fantastic as Derick was, the person I most want to be with is, obviously, Bruce. Damn, life is far from perfect.

I sit in the sun, then under the umbrella, wishing I'd remembered to bring my book. Hmm, I do some boy watching with some success, although the guys I thought were interestingly cute, hot, and sexy tended to be Markie's age. Oddly, I find macho guys, musclebound and hairy, unattractive. Maybe that's because my best time sexually was in prep school, and I'm projecting back to those glory days for me--glory days when I wasn't tagging along after Ronny that is.

Frustrated from thinking about that, I go in the ocean for a long swim blanking my mind to concentrate on doing a mile swim. Unable to make it back after swimming a half-mile down the beach, I get out and walk the last two hundred yards back to my chair, breathing hard but feeling invigorated too. That's just what I needed to lose the last of my submissive feeling for Derick. I'm good now, feeling like myself, which means all my thoughts are about Bruce.

I was not especially hungry after that big breakfast two hours ago, but I want to see Bruce, so lunch at the cafe is my next move. First, I use the outside open shower at the top of the beach. It's just a pipe in the ground with a showerhead for washing sand off your feet before going on the boardwalk or going to the parking lot. I stand under it, washing the salt from the ocean water and sweat off, then dry in the sun for an hour. At two o'clock, I put on the polo shirt and carry my sandals to the boardwalk to have lunch at the cafe and to see my lover boy.

This time at the cafe, I get seated in Bruce's section, and he waits on me, asking, "Will there only be one for lunch, sir?" Grinning, I go, "Sadly, yes. My boyfriend is working, so I eat alone." He drops a menu on the table, saying, "Well, your boyfriend is a lucky guy." He goes off to deliver lunch to the table next to mine as I glance at the menu. Not being especially hungry, I order a Coke and a bowl of clam chowder."

As Bruce serves it, he asks, "Did the guys take off on time this morning?" I'm like, "Haha, they were a bit late because Lee was diddling Cowboy a couple of times. Maybe they're worried they might not be able to keep up with their rabbit-like frequency of having sex in New York." He grins, taps the table, and says, "I'll see you on the beach in a couple of hours."

We have a nice afternoon on the beach; then Bruce treats me to dinner at that Italian restaurant near the hotel we stayed at, seemingly, a long time ago. We're in bed at nine o'clock with me horny for Bruce, but not generically horny as I was the last few nights. Derick took care of that for me. And, yeah, I don't blow my load as quickly tonight, so neither does Bruce. After cleaning up, we're back in bed snuggling, and Bruce says, "See, that was better, wasn't it? I told you we'd quickly get comfortable with only bedtime sex. It seems more special now." I nod against his shoulder, then lean my head over to kiss him, murmuring, "Yes, you're right again, Bruce. I love you." He gives my shoulder a squeeze, murmurs, "Good night," and we fall asleep.

To be continued... donnymumford@comcast.net.

Please consider making a tax-deductible donation to nonprofit Nifty to help with the expenses of maintaining this huge and diverse free story site. Thank you.

Next: Chapter 45


Rate this story

Liked this story?

Nifty is entirely volunteer-run and relies on people like you to keep the site running. Please support the Nifty Archive and keep this content available to all!

Donate to The Nifty Archive
Nifty

© 1992, 2024 Nifty Archive. All rights reserved

The Archive

About NiftyLinks❤️Donate