My summer of sex with Cowboy

by Donny Mumford

3 May 2024 211 readers Score 8.6 (7 votes) PDF Mobi ePub Txt


Chapter 47

Dickie came through for me! Yeah, I guess it'd be better if Dickie had a bigger cock, but he gets all there is to get out of the small one Nature provided him. I like him! It's a little different, but he still managed to get me slightly submissive, and I had a good climax. Nothing remarkable, but it was okay. But it's funny how quickly I've become enamored of confident pussy boys, like Jon, Dickie, and Derick after Bruce and I became best friends; instead of boyfriends and lovers. Bruce was never my boyfriend or lover, though. He tried go fake it for my benefit stressing himself out enormously, but he couldn't be convincing. 

Oh, Well, I still love Bruce, but as my best friend, now. Other than my missing out on Bruce as a lover, everything else in my life is better than it's ever been, and that is mainly thanks to my commitment to the pussy boy's escort organization. I include my paddling therapy. I call it therapy instead of discipline because I'm seeing Richard's tough love in the paddling and the benefits I'm experiencing through self-awareness. I've got some things to work on, in other words.

Thinking these thoughts, I'm walking up the boardwalk to Anne's Cafe to meet Bruce at five o'clock. At the cafe I see they're still closing up, so I smoke a cigarette leaning on the boardwalk's beach-side railing opposite the cafe waiting for Bruce.

That I have life issues to work on doesn't bother me all that much because I now know what I like, whereas I was floundering living my life through Ronny. When he was killed it was like my life was killed, too. Traveling with Ronny's brother Cowboy, Carson actually, I didn't realize he had a life I wanted. Cowboy is a perfect specimen of a younger guy, who's also beautiful, but I never fell head over heels for him and that's because we're too much like him, meaning we're both happiest being submissive bottoms, following a leader.

Cowboy doesn't have a dominant bone in his body. He's the sweetheart type, an almost perfect young gay guy who enjoys life to the fullest. I don't have a sweer bone in my body, but other than that We're alike. And I'm being too hard on myself because I'm a compassionate person supporting guys down on their luck. I just don't do it as sweetly as Cowboy.

Sure, it helps that he's independently wealthy, but so am I, and it's taken me many months to get into a positive frame of mind with the pussy boys. Cowboy has had that outlook for as long as I've known him, and I've known since he was born. Ha, and right now he and Lee are in puppy love, and if it doesn't work out long term, which it probably won't, they'll be broken-hearted for a month and then move on to fall in love again. They've only recently turned nineteen, so they have all the time in the world to rebound and fall in love all over again.

Lucky bastards, but I've blamed myself many times this summer for wasting my youth trying to be someone I'm not... now I'm done with that. I'm doing my best catching up on as much of the things I've missed as possible, and, consequently, I've been happy this summer, even with all its ups and downs. 

While I believe all of the above is true, the most important factor is admitting I was wrong about what Bruce was trying to train me when I was faking being a pussy boy. Bruce didn't have a knack for the trainer/mentor role so between the two of us we fucked it up pretty much. In the process I fell in love with him, or thought I did. That's turned into brotherly love but he's still destined to be a constant in my life, just not as my lover.

That removes a lot of sex from my life and I need to get my horniness under control, which I'm working on. I'll be gradually reducing my need for multiple sex acts each day until I'm prostituting to experience that for a while. I'm going to make sure it doesn't ruin my appreciation for sex as I want a real, long-lasting relationship, hopefully before I'm thirty. In the meantime, I'm learning about myself, seeing everything differently from my new perspective as a sincere pussy boy in training. 

Bruce admitted that he felt making love with me was an obligation because I've helped him with an alternative lifestyle. He's made excellent progress, especially since getting the waiter job, and now that we're best friends instead of pretend lovers, he's finally relaxed and enjoys this life style. I'm switching places with him and so far it's worked out for me. Bruce's job means I'm on my own for too much of the day. On the other hand, it gives me the time to deal with my horniness, so...

I want and need a dominant sex partner and they need to be extra dominant because I don't love them, but the significant point to me is I used to think I was the opposite. I had to be the 'top' dominant jerk. Ronny was mostly responsible for that, but I've been over it before. The most exciting revelation of my life happened way back when Richard first fucked and dominated me into the disclosure, the realization that I've been pretending I was a dominant top. I'd been acting the part of a dominant top and not enjoying it much for years. Richard exposed me for who I was and now I'm following through on the transformation he began.

Hmm, all these thoughts swirls around my brain until I stand and yell at myself, "Stop it!" Oh shit, haha, everyone in the vicinity turned to look at me, including the two gay swisher lovers sitting on a bench, who I smile at. That was random...


Here comes Bruce. We're both comfortable with one another now. What was I playing at before? Bruce smiles and pats my shoulder, murmuring, "Zach, hi!" I remind him my name has changed to Zippy and we chuckle, Bruce muttering, "I'll stay with 'Zach.' 

Dickie came through for me so I'm calm and definitely not horny which I want to be all the time. I don't want Bruce to detect that I'm horny as a buzzard because it'll stress him out that he's letting me down. He's NOT letting me down, but he'd think he was so I'm going to work on not being horny. It is disappointing my infatuation with Jon Scheyer is going no where sexually because his position as a mentor/trainer precludes me hiring him as a pussy boy. I'm still hiring other pussy boys, Dickie being the most recent, so I'm depending on paying my way, and hopefully getting my horniness reduced to one fuck per day.

Bruce and I talk about the boys returning, if everything goes as planned, tomorrow. I make drinks, taking mine in the bathroom to shower. We fix dinner together with our second drink, me making the salad and boiling the corn on the cob for three minutes. Bruce doing everything else. After dinner we watch TV, Bruce's arm across my shoulders and it's very casual, peaceful, and relaxing. We don't talk much about what I did all day or about what's up with the pussy boy organization. 

We're in bed by nine o'clock because we get up early... at five. It goes fast in the morning. Bruce showers morning, we make take-out coffees, and I drive us to Atlantic City so Bruce can be at work by six o'clock. We bump fists, "Have a good day, buddy!" Then I walk the boards smoking and trying not to think too much about the discipline paddling at eight o'clock. I'm killing time watching the young guys jogging on the boards, looking for cute ones. There aren't many even among the very young. True cuteness is rare and get rarer the older guys get. There are good-looking guys like me and pretty ones like Cowboy and Richard, but cute guys are kind of rare.

I see guys in their early twenties who were probably cute as young teenagers, but aren't cute now. Often cute teens make for funny-looking adults. Haha! Killing time like this keeps my mind off unpleasant things like paddling. It's unpleasant while it's happening but has been an eye-opener for me, but I've gone over that in my mind enough. 

The cafe around the corner from Eli's apartment building opens at seven so I get another coffee there. Drinking it I remember Billy saying he was being paddled for the first time this morning.  Apparently, the new thinking is that all new recruits get a taste of paddling to encourage them not to do anything that might get them paddled for real. No matter what excuse Richard has for my paddling, it's because I fucked the organization up and this is getting even.

Eli and Jon claims there are other reasons and I don't care what they are because the paddling has mad me in introspective and blah, blah, blah. I've been over it too many times as if I'm talking myself into believing it.

When I'm wandering to the front entrance of the apartment, I see Billy pacing back and fourth. He's okay looking but his body is, um, bulky, and his lips are fucked. Haha, they're flat without shape, or something. He says, "Zippy! Oh, thank God. What do I do?"

Shrugging, I say, "Hell, I don't know. Who told you you'd be paddled today?"  "Um, I guess it was Jon, but he said he was told. I don't know." I say, "Don't worry about it. It's not your problem. You're here as ordered; the rest is up to them."

Them Sandy appears and does the neck gripping to Billy, telling me, "Open the door," handing me a key. I do that and he gets my neck with the other hand. I sigh because this is one of the stupid routines they've kept, but what the hell. Billy's whining, "Ow, ow, no..." Yeah, I used to do that. too. It's a waste of breath.

In the discipline room, Billy and I get undressed and we're parked in corners. We hear paddling muffled screams, but no bladders being let loose. We'd hear piss hitting the bucket if that happened. Then Sandy is putting the ball gag in Billy's mouth, Billy complaining like mad, then the dog collar and, I don't see it but hear, "Whack! Whack! Whack! Whack!" and a lot of muffled screads from Billy. I almost snickered, but then was mad at myself for almost snickering. Then it hits e that Billy got four paddles and the new recruit yesterday only got two. Huh.
Then there's a ruckus and grunting and, "Well, open wider and we'll get it out." And then Billy voice, "Fuck you! Get this piece of shit dog collar off!" and then what can only be fighting/wrestling and I have to take a peek. Yet, Billy swinging his fist and two pussy boys are wrestling him to the grown as Billy yells, "I quick thius chicken shit organizatiom. Let me up... I'm calling the cops!"

Some guys don't take to paddling as well as I did. The threat of the cops got the pussy bpys backed off trying to passify Billy, "It was part of, just routine. You don't need to quit, you..." but Billy has his shorts on and sneakers without socks, carrying underpants a pull over to screaming, "Get away from me!" Everyone got away from him and he stormed out of the lavatory slamming the door against the wall opening it.

Everyone is talking at the same time until Eli comes in yelling, "What the fuck happened?" There' yelling from Sandy and the short stocky black guy. both trying to blame Billy, "We didn't do anything differently. His buttocks, um, Sandy, what was that?" Sandy shrugged, "I don't know. His ass blew up, um, got enflamed or something. Tender flesh, something. I never saw anything like it before." The black guy says, "He's going to call the cops."
Eli says, "The rest of you guys get dressed. Who knows where that asshole might be going?" Pulling on my underpants, I say, "He lives in that dive apartment on sixth street." "Do you think he's going there, Zach?"

What happened to 'Zippy?' I say, "I don't know where else he'd go." I'm dressed and Eli says, "Come here," and we step out of the lavatory. "I'm going to the dump apartment, you go to Jon's incase, what's his name?" I mutter, "Billy-something." "In case Bily's there. We do not want cops involved. If you see him try calming him down and bribe him, if necessary, Tell him you've heard we'll give him money to keep his mouth shut. We spent a hundred thousand dollars keeping outside authorities away from the club disaster."

Nodding, I leave and drive to Jon's. Eli is going to see if Billy's at the apartment. Thinking about it, I'm not surprised someone refused to go along with this barbaric tradition. They do it in frat houses, too. In fact, there is a lot of fraternity nonsense in the pussy boy strategy of getting recruits in line. Some military tactics as well. It works for me, but not for others. Hell, that's why it's hard recruiting pussy boys, but the ones who finishes all the way through the training and indoctrination do make clean-cut, excellent prostitutes.

Billy isn't here and I didn't think he would be, but Jon wanted t hear all about it. Humans love gossip it seems. When I've told all I know, Jon is texting to see if there's an update and Corndog asks, "Do you want to blow me, Zippy? Sixty bucks. right?"  

Well, why not, so I look at Jon for an okay and he mutters, "Yeah, go ahead if you want." Corndog and me go into his and Peanut's immaculate bedroom, so different from the rest of the apartment, including Jon's and Benny's bedroom.

Corndog is about five-foot eight or nine inches with an average, nothing special build and brown hair and eyes. He the average, average kid. He pulls his cargo shorts down and I fiddle with his average penis, asking, "What's your real name?"

He says, "Michael O'Rourke." I stroke the foreskin, that slightly longer than most after circumcision, and asks, "Did you graduate high school?" 

"Yeah, I did last year. What's it to you. You writing a book?" Smirking at him, I shake my head, not wanting to say how much I liked young guys and their young dicks. I didn't used to pay any attention to young guys and then spending these past months with Cowboy and lately with Lee, I've learned to appreciate how special they are. That, plus I wasted my teen years, so... 

Anyway, I drop to my knees and, without further ado, I put his average dick in my mouth and immediately notice Michael isn't as immaculate as his bedroom. He needs a bath and his penis taste like pee. The pee taste is enhanced, made stronger by the urine smell of his pubic hair. Did he pee himself and not clean up? Well, I've drunk urine the past couple of days, so a urine smell is no problem for me. Grunge is sexy in its own way. Not too grungy, but Michel's grunge I'm kind of getting into.

Sucking, then. licking his five-inch cock, I soon eliminate the urine taste although the smell remains. Corndog claims to be straight, only letting a gay guy blow him because he needs to money, but maybe that's not the whole truth because, while a straight guy will get hard eventually having a gay suck his dick, he wouldn't get hard immediately like Michael here just did. Rock hard boner in one minute and he's doing little hip humps and he's a sexy boy moaning, "Um, um, aah, ahh..."

Yep, precum already, so I take his hard boner out of my mouth and press it to his hairy groin ad lick his average balls and then, finally getting a boner myself, lick the inside of his legs and then his balls again and he climaxes, cum shooting straight up skimming his pubic hair and arching over my head to land with a "Splat" behind me on the hardwood floor. He shakes, squeezing my head, then shoots a second spurt of cum that hit my forehead.''

I sit back on my ankles, wiping his cum off my forehead and tasting it. No taste. Corndog is squeezing his eyes shut as he's squeezing his dick. I mutter, "You should be paying me the sixty bucks. Do you work?"

Taking a deep breath, he opens his eyes and let's go of his dick, saying, "That was good. My first gay blowjob. I'd do it again for, um, forty dollars."Chuckling, standing, I reach into my pocket and get three twenties. Giving them to Corndog, I ask again, "Do you have a job?" He takes the money, "Yeah, I'm a bag boy at the Penn Fruit. I'm joining the Navy at the end of the summer. In two or three weeks. Now you can finish writing your book about me."

He pulls up his pants, and we go to the bathroom, which is not immaculate either and wash up. I say, "I'll hold you to the forty dollars next time.' He says, "Nooo! I was caught off guard how good it felt. I wasn't in my right mind when I said that." Haha, he's a funny kid. I pat hos shoulder, 'Yeah, okay."

In the living room, Jon says to me, "I've got to go to Eli's. He caught up with Billy and it looks as if he, Billy, won't go to the cops but it's going to cost some money, I guess, He said he'd come back with a guarantee he'd never be paddled but Eli said Richard won't okay that."
I nod, think I've got the rest of the day to myself, wanting to see Dickie in the hotel room I rented. Yoo-hoo! But, no. Jon says, "I'll be back here, but I don't know when, so I'll see you tomorrow. Come here at nine o'clock. The paddling program is temporarily on hold until Richard figures out what to do."

Nodding, I mumble, "Sure, Jon. I'll see you at nine o'clock tomorrow. I hope everything turns out okay." He shrugs, "I didn't have high hopes for Billy to start with, but who could have predicted this?"

As I walk out, I think about how it will just be Jon and me moving forward and that's what attracted me to do this pussy boy retraining in the first place. Jon is my replacement for Bruce and for Ronny before that. I need a bossy authority figure in my life. I don't care if that makes me a wimp! It's how I'm made up, so eat shit if you don't like it. That might be a tad too strong of a response from me, but...

Haha, and why am I angry? I've got the rest of the day with hot shit, Dickie. Driving to the other end of the boardwalk, near the locker room and Anne's Cafe, I park in the lot and at five-after-nine, I' knocking on the door of the room I rented for Dickie and me.

I need to knock three times before a sleepy-eyed Dickie opens the door wearing only jockey underwear, asking, "Is it one o'clock already?" 

He makes me smile, and, as happens with me, the more often I see the same pussy boy, the cuter he seems. I rub his too-long hair, too long for a pussy boy, saying, "This is better than one o'clock." Ignoring me, he leaves me standing at the door as he goes into the bathroom. Huh, I walk into the room and close the door behind me.

Dicky comes out of the bathroom looking awake now after washing his face and slicking down his hair. He's taking off his underpants, saying, "My work day begins. Give me two bills upfront, and we'll get right to it." 

After dropping, two hundred-dollar bills on the bed, I quickly got undressed, then fell to my knees in front of him. Again, I need to stifle a snicker when I gawk at his three-inch penis with the oddly large head. He immediately takes hold of my head with both hands, the head on my shoulders, and pulls it down to his junk, then presses my face against his junk and rubs my face around a little, saying, "I need to do a better job of earning my money. I was too buddy-buddy with you earlier... I need to be more dominant when serving an 'S' type client such as yourself."

Well, yeah, sure he does since I don't even love him a little bit, getting dominant sex from my hired pussy boy in mandatory at least. My nose rubs tightly on his belly where his pubic hairs would typically be as my lips drag over his cock, my chin hitting his scrotum. He's slowly moving my face back and forth on his privates while I'm acting docile, letting him do as he wants and I just felt an inkling of submissiveness. Letting myself go with it, I'm not thinking much about anything except Dickie's hands on my head and the feel of his naked privates' area against my face, plus his scent... it's becoming nicely dominant of him, and sexy.

He says, "The clock is ticking," so with my face squished against his privates, I try to lap the head of his cock into my mouth. He's still moving my face a little this way and that as I get my tongue out all the way and lick the abnormally big head of his otherwise small penis. It takes five or six good licks before I feel it stir under my tongue. Alright, now that I've activated some erectile fluids, they begin flowing into his sex organ, such as it is. 

I do a few more long licks, and his dick firms up a little more, and then a lucky lick gets under the head, and I grip the neck of his dick between my lips. Using very little force, I move my head up slightly, his cock slides inside my mouth on my tongue, all three inches of it. Dickie goes, "Ummm." 

I've got it now and go to town licking the head while sucking on the skinny shaft turning his baby-dick into a hard spike with a blunt head. Needing oxygen, I turn my head slightly to the side to inhale a deep breath through my nose. He lets up on my head now, shuffling his feet, and now I'm able to bob up and down on his steel spike. 

Precum soon drools out, and he's pushing my head away, saying, "I don't want to cum. Assume the position." I drop my hands to the floor. Then, I start to push up my ass from habit but quickly realize that's not what Dickie needs. He's too short to want that, so I lower my ass a little, and he spanks my ass with his hand. I'm embracing the submissive sense, missing my morning paddling, my face squished against his crotch, and now letting the submissiveness expand as my spanked ass stings.

When the stinging gets too much, I start walking on my hands and knees to get away from his spanking hand. In my deepening delicious submissiveness, I don't think of complaining about my stinging buttocks. Then, unexpectantly, he rams his cock inside, firing the head in past my sphincter muscle, and I go, "Aiiieee," as he grabs my hips and begins humping his boner back and forth inside me like a mad man, "Slap, slap, slap!" 

Three inches or not, a cock jammed in past sphincter muscles without lubricant is going to hurt. Not for long, though. The pain quickly fades as I stay still for him, allowing the pounding in my ass with my eyes wide open as I make little quick moaning sounds, "Ah, ah, ah, ah, ooh, umm..." Great pleasure is bursting off my prostate; that's in a constant state of super stimulations.

Everything he's done was unexpected, and I'm highly aroused, feeling pleasantly dominated. It's a quick three-minute thrill ride, then my back arches, and I squeal embarrassingly as my wooden boner spurts out one, two, then a third hot creamy streak of cum. Not long lines, but the sensations take my breath away. The second Dickie heard my squeal, he pulled his cock out, leaving me shivering and shuddering, not knowing what happened for a second there. It was such an unexpected abrupt entrance and then an abrupt withdrawal; it was all so, um, all so startling. 


Swaying on my hands and knees as the after-effects of that climax swarm over me, shivers going down my spine to my toes, I feel weak but good too. I look over when I hear the faucet turn on in the bathroom and see Dickie washing up at the sink, and only then do I notice cum drooling out my ass and down the inside of my left thigh. Yeah, he didn't have time to put on a condom, so he fucked me bareback. I'll bet he got so aroused from spanking me, he lost it and went crazy. Awesome, from my point of view!

I start to stand as he comes out of the bathroom, Dickie saying sternly, "Stay down!" I get back on my hands and knees, looking down and feeling that awesome submissiveness again. Looking at the floor, I see the three little blobs of my climax. Little nuggets of cum that felt like long streams of creamy semen when coming out. He grips and squeezes the back of my neck, saying, "Good, you did what you're told. Was that dominant enough for you?" 

I say, "Yes, Dickie." He pats my head, mumbling, "I told you you'd get your money's worth. You can get up now." Letting out a long-held breath, one I didn't know I was holding in, I get up, and he points at the droplets of cum, saying, "Clean that up." As I do that, he gets a nine-dollar bottle of OJ from the little convenience bar, sits down, and asks, "Did you set up this date through Richard?" 

The submissiveness drains away rather quickly, and I get embarrassed for becoming that submissive to little Dickie, um, the person, not his... oh, never mind. Well, it's what I wanted, right? I say, "No, because he's dealing with a crisis," and tell him what happened,

He says, "So you missed out on your paddling?"


Nodding, I change the subject, "You didn't use a condom," which doesn't have anything to do with paddling. Somehow, Dickie paddling doesn't resonate as improvement for me. It's simply dominant paddling. He goes, "That's right, I didn't use a condom, but no extra charge. So, you'll get in touch with Richard about this morning and set up a date for tomorrow, right?" 

"Yes, I definitely will." Still a bit groggy, I'm just standing here holding the tissues I used to clean up cum droplets as his large deposit of cum continues drooling down the back of my legs. Dickie swallows some orange juice, totally comfortable being in charge. He points to the bathroom, "Go clean your ass, and then I have a suggestion for you." 

I nod and go into the bathroom, grabbing a washcloth and wetting it, then wiping his cum off my butt cheeks, anus, and legs. It's still leaking out, though, so I hold a few tissues at my asshole, only now realizing how terrific I feel. With the tissues held at my ass, I walk back to the bedroom, asking, "What's your idea?" 

"First, how'd you like my escort service?" I grin and say, "Top notch, excellent, although too fast." He says, "Hey, you're the one who blew his load first, then I blew mine seeing how aroused I'd gotten you. It was a turn-on." That's a lie. He had to blow his load first because he pulled out the second I squealed at my climax. And, I could mention the real turn-on for him was his spanking fetish, but I won't because I don't want to embarrass him. Instead, I say, "You surprised me about three times... it was hot sex, Dickie, scorching hot sex."

"Okay, then, I did my job. Now, here's my idea. You arrange another date with me, an overnight date this time, and I stay here where I'll be available to you at whatever time it's convenient for you." 

I ask, "How much will that cost?" He shrugs, "My main man, Richard, will decide that. You'll need to ask him." 

"Well, I need to leave for Jon Scheyer's at eight thirty." He mumbles, "That's no problem."

"I'll rent the room for another day and you'll be here for whenever I can make it. That sounds expensive, but let's try it."

He finishes the OJ, standing and saying, "My shift for Richard starts now, and I'm on call from now on until like seven o'clock." Right on cue, his cell phone rings. He gets it and answers, "Yeah?" Listening, then, "What type and where?" Then he says, "Well, I just now finished with that 'S' type client you hooked me up with." Listening, then he goes, "He said you were dealing with a crisis and he'd be sure to tell you he had a date with me."

Ending the call, he says, "Yeah, that was Richard, and I told him how much I made so far; I included the freelance thingie here too. I don't want to cheat him. Anyway, he's got another client for me... a sixty-something-year-old guy who's waiting for me at a casino hotel. I can easily walk to the hotel from here. It's only ten blocks or so." I'm nodding while checking to see if his cum is still drooling out of me. 

He adds, "Wait for a few hours before calling to set us up for tomorrow. Do we have a deal?" 

"Sure, great idea, but I'll be here tomorrow around noonish." Shrugging again, he says, "Well, I'll be here too." We both get dressed; he takes the key card with him, mumbling, "This is great. After my shift, I'll come here and have a good night's sleep for once." Dickie opens the door, then turns back and asks, "You won't mind if I charge a little something from room service for my dinner, will you?" 

I wave a hand, "Of course not. See you tomorrow at noon." When the door closes, I check one more time to make sure no more of Dickie's cum is leaking out of my ass. Nope, I'm good. Twenty minutes later, I'm sitting in my beach chair wishing my best friend and ex-lover, Bruce, was with me. 

Hmm, Dickie said to wait a couple of hours before calling Richard to set up an escort date with him. Fuck that, though; I'll do it now. Looking up the phone number, I call and Richard answers all business-like, acting as if he doesn't know me. Fine by me. I give him a credit card number, and he gives me the bullshit line that the $200 includes a massage and lasts an hour. This is how the mentors make most of their money. The pussy boy gets only ten percent of the two hundred dollars, but ninety percent of their tips. 

Anyway, I set that up, and then spent a minute thinking about the semi-hot time I had with Dickie. Most of it was okay, and there was some dominance involved. Maybe his dominance, psychologically, is enhanced because of him being so much smaller than me, plus his small penis. Ya know, acting submissive to that. Yeah, it's kind of crazy.

Now I've got this thing for Jon Scheyer, so am I a person who habitually falls in love, as I've been accused of doing by some? Do I catch love as if it is a virus of some sort? Do I need to be loved as a self-esteem thing? And why am I asking myself these questions when I know I don't have the answer to any of them?

Love hurts so good; sometimes it doesn't feel like it should. Bruce not loving me should have hurt more than it did and I think that's because we really care for one another as best friends. Seriously close friends. I take a long swim and then have lunch at Anne's Cafe although I get seated in a waitress's section, but Bruce and I exchange smiles.

Bruce surprises me two hours later, showing up on the beach, "Anne told me to enjoy some beach time." 

I say, "Awesome, you make me happy." He seriously says, "You've made it possible for me to be me happy, Zach, and I can't recall being happy before meeting you." 

"Thank you, Bruce. We make each other happy." I'm leaving it at that. I want to get over constantly beating myself up for making so many wrong choices over the years. My infatuation with Ronny seems so misguided to me now, and I can't explain why it didn't seem misguided when Ronny was alive. I've been a mess for a long time, but I feel as if I'm on the right road now, and I don't know for sure it's the paddling that got me reevaluating myself or something else. It doesn't matter, anyway. I'm on the right track.

Even though I'm getting into another thing with Jon Scheyer, I'm not faking being happiest when I'm with Bruce, and I'm not faking loving Cowboy and Lee like brothers, so I'm not going to worry about it. Glancing at Bruce, I see his eyes are closed, and he looks, his facial expression look comfortable and relaxed. He didn't use to look that way, not until a week or so ago. As I've realized before, I'll never be able to put myself in Bruce's place the same way he can't put himself in mine, so we both need to deal with the here and now, and every indication is the here and now is working pretty fucking well.

Later, Bruce wants to do the mile swim, so we do. I can see him struggling after maybe a quarter mile, so I'm like, "Let's float awhile before doing the half-mile back." He nods, gasping for air as he catches his breath, then says, "A half-mile is a long way." Nodding, I go, "Uh-huh, but you're getting there." He doesn't know what a half-mile is, and why would he? Very few people can swim a quarter-mile, never mind a half-mile or mile. It's hard! 

When he looks rested, I go, "Ready?" He nods, and I keep a slow pace, swimming back. Coming out of the water at the lifeguard stand that I use as my marker, I put my arm across his shoulders as we walk up the beach, telling him, "There's maybe only one person out of all these people you see on the beach who could do the swim we just did." 

He gives me a grin, "Really?" I nod, "Yep, really. Be proud of yourself." He goes, "I thought of myself as athletic as a teenager, but never put in the work to be on a team or anything like that." I can see he has a natural, athletic, God-given body, so I believe him. He's slim, but like Dickie, he has a sculpted body, although Bruce is four inches or so taller than Dickie. I think Bruce is perfect.

We stay on the beach until six thirty, then stop on the way home for Chinese take-out for dinner... again. At the apartment, I put the unique Chinese take-out containers in a warm oven, and we have a shot of Jim Beam with a can of Bud Chaser. Then, we take the beers to the balcony for a smoke. Lighting two cigarettes, I pass one to Bruce, who smiles and says, "You like doing things for me, don'tcha?" 

"How can you tell?" and grin at him, adding, "You're my best friend, so, yeah, I get off doing shit for you." He says, "Thank you, but you're way too good to me." I hug his waist, murmuring, "Stop putting yourself down."

Holy shit, he looks away, rubbing his eyes, sounding choked up, saying, "I wish I believed in God so I could pray my thanks for you." 

I mutter, "Ditto for me," and he leans against me, wistfully murmuring, "I do wish I knew how to thank you properly, Zach. I really do." 

"You've thanked me plenty, Bruce. Over thanked me actually because everything I try to do for you is for me too. I have a selfish motivation for trying to please you. You're the best friend I've ever had." 

After eating Chinese takeout, Bruce takes a shower, and then I take mine. We're in bed by nine o'clock, seeping against one another. The alarm goes off at five o'clock, and, like zombies, we go through our morning bathroom ritual and leave for Atlantic City on time.

Later, in the car drinking our take-out coffees, Bruce is chatty during the twenty-minute drive to the boardwalk. Mostly, he's talking about how Anne, the cafe owner, is thinking about selling the business and how we could buy it and keep it open year-round. He says, "It's only a block and a half from the big group of casino hotels, and if we advertise it properly as an alternative to the high-cost breakfasts in the hotels, we could have a thriving business. Same for lunch, especially if we can get a liquor license. Then, why not keep it open for dinner too, ya know?"

I'm mumbling, "Uh-huh, hmm, yeah, I see what you mean," but I'm not crazy about this idea. I don't want to work in a restaurant! I like his UPS idea or, even better, an online business of some kind. Something like that where we'd make our own hours. Some kind of business that requires a lot of travel to interesting foreign places. We'd travel first class and stay at five-star hotels. For now, I'll let Bruce's cafe idea die a slow death as I'm assuming, in time, he'll talk himself out of it without me needing to drop a wet blanket on his idea.

At the ramp, I say, "We'll give a lot of thought to your restaurant idea these last three weeks that Anne's keeping the cafe open." He says, "But you think it's a possibility, right?" I nod, "Sure. it'd be cool." 

He grins, "It would be, thanks," and he leans over to give me a friendship kiss, "Have a great day, Zach!"
Watching him jog up the ramp and turn the corner, I smile, feeling good about how well he's handling himself as a young gay man in this new life of more or less normalcy. I don't want to do anything to fuck that up.

I don't need to be at Jon's until nine, and it's only a little after six, so I drive back to the apartment and sleep for two hours. Whatever happened to my idea of buying a second car? Then, I drive back and park on the street near Jon's apartment. He opens the door when I knock, saying, 'Billy's gone, so it's you and me. I'll be acting as the client when you're practicing your pussy boy escort role."

I nod as if that's okay when I'd like to do a cheer. It's what I wanted from the start. There are no blowjobs or urine play today, so it's Jon and me in his office going over familiar pussy boy stuff I remember Bruce going over six weeks ago. Some of it is still stupid, and some of it makes sense, but either way, I enjoy having Jon's undivided attention. He didn't explain how Billy's situation was resolved, and I didn't ask because I didn't care. I got what I wanted, which is Jon all to myself.

Jon says, "It's only eleven thirty, but we've covered everything scheduled, so you're dismissed. Tomorrow, get back into the eight o'clock routine with Sandy. You'll be getting paddled again." Oh, I hope he sticks to four paddles.

Grinning, as I start the car, I'm thinking about Dickie, my only sexual outlet. My expensive, only sexual outlet. It's so much cheaper to have a boyfriend. Who can I romance as a boyfriend? Hmm?

When I knock on the door of the room I rented, Dickie opens it looking as if he's still asleep. He nods, muttering, "Hi, c'mon, get in here." Walking into the room, I say, "It's barely good morning! Did you get a good night's sleep?" 

He got a haircut yesterday, although it's not as short as mine. Dickie mumbles, "No, I didn't get a great night's sleep yet. Give me a hundred dollars, and you can sleep with me a couple of hours." 

Hmm, yesterday it was nip and tuck sensing submissiveness with Dickie, which I'm paying for while not getting much of it. I'm like, "No, I'm not paying for you to get two more hours of sleep." 

I could go for a couple of hours of sleep myself, but I'm not a big enough sucker to pay a hundred dollars so Dickie can get two more hours of sleep in the 'effing hotel room I paid for. He slept naked, which I approve of, and I would like to sleep with him but not pay a hundred dollars even though I couldn't care less about a hundred dollars.

Well, that's not true. I care about a hundred dollars, but not as much as most. Dickie scratches his balls, which are standard size even though his penis isn't, and mumbles, "I got a text yesterday that you set up this date with my main man, but you didn't wait a couple of hours to do that as I told you to." 

Shrugging, I go, 'What's the dif?" Shaking his head, he goes, "Get undressed. I have a surprise for you." 

Kicking off my sandals, then pulling my T-shirt over my head, I go, "We can sleep a couple of hours, but we'll do it after our escort date starts."

As I drop my shorts and underpants, he gets a paddle out of the satchel he has his change of clothes. He yawns, then says, "I went to the trouble of borrowing this paddle because when you mentioned it yesterday, there was something in the way you talked about paddling that told me you liked being paddled." 

Shaking my head, I go, "Wrong! I just heard about it from a random pussy boy a couple of weeks ago. Look, we're getting off on the wrong foot this morning. Let's do it your way and get in bed to sleep for a couple of hours, then start fresh. Whaddaya say?"

He says, "Nope. I'm in charge, and since you gave me some shit about not paying to sleep with me, we start your escort date now. As I already said, the paddling will cost you fifty bucks and then a hundred dollars for sleeping with me. Get naked on your hands and knees. First, though, let me have the hundred and fifty right now and no more lip from you."

Oh, shit, that authoritative bossiness got my dick moving. Dominance at last. I wasn't paddled today, and Dickie knows that because he's always talking to Richard. It won't have the same effect if Dickie does the paddling, but I can't pretend I don't like it. 

He's standing there, the paddle resting on his shoulder, as he says, "Do what I said, or you can try getting your money back from Richard, and we'll forget about this date." 

Well, I'm not doing that, so I make a face, then get a hundred and fifty dollars from my pussy boy light tan shorts and hold it out to him. He says, "Bring it over to me." Oh, yeah! I get a submissive twinge in my nuts from that. Well, okay then, good. This is what I'm paying for.

Hot shit! I actually feel timid walking the four steps to Dickie, hand him the money, and mumble, "Sorry, I, um, ah..." and leave it at that because I can't think straight. He tosses the money on the bureau, then says, "Instead of getting on your hands and knees, bend over, hands on your knees, and push your ass out." I do that, and he taps my ass with the paddle, mumbling, "I said to push your ass out, not up." I do that, and he goes, "Don't fucking move." 

I hear, "Swoosh" as he swings the smooth wooden paddle, then, "WHACK!" it connects with my buttocks, and I go, "Oooh!" He gives me four hard paddles, then says, "Stay," and that one word after being paddled puts me into a deep submissive frame of mind, my buttocks quivering, feeling red hot, and stinging, but not as bad as when Sandy does it.

Dickie saunters around in front of me and says, "Huh, we both have our pussy boy haircut, but you're not a pussy boy, are you? I think in your heart and soul you wish you could be, but you couldn't hack it." Dragging the paddle along my spine, he walks back to his position and "Swoosh" "Whack!" Then he says, "You're done, you can get in bed." 

Reaching back to rub my buttocks, I mumble, "Yes, Dickie, and I do want to be a pussy boy. That's why I'm working with Jon and getting paddled every morning but today, um, until now." and scramble, almost tripping over my own feet to get in bed and under the covers, my ass feeling raw, still stinging like a motherfucker.

Dickie says, "And you know that I know all of that already. I think it's cool, but we're on an escort date, so..." as he takes his time closing the curtains, blocking out daylight, then gets in bed, holds out his arm, and I slide right over to lie the back of my neck on his arm. He pulls my head over, saying, "I don't want to hear another word out of you unless I tell you to talk." 

We wrestle around a little until he's comfortable and stays, "Stay still." It's awkward because he's smaller than me, but I like the feel of his body and finally relax, then feel really good. My ass still stings, but Dickie did an excellent dominant job this morning and earned his money. I feel properly submissive to him as I snuggle in just a little bit more, my leg against his shorter one, my forehead against his chin. He smells good too. 

That makes me think about how Derick smells good, too. Who do I think is a better pussy boy, Derick or Dickie? It's Jon, but I mean, between those two. I would have said Derick immediately before yesterday and today, but the dominance is getting good with Dickie now, so...

When I think about it, I admire the moxie of pussy boys like Dickie, small of stature, and in Dickie's case with a small penis, and yet he can pull something like this off. Of course, he couldn't pull it off unless his client wanted him to, which super 'S' types like me want, but it is still interesting to witness him doing it firsthand.

That's my last thought before falling asleep. Sure, I got nine hours sleep between last night, and this morning but there's something about getting up at five o'clock that makes me think I need more rest. Whatever, I sleep for less than an hour, then see Dickie's still deep asleep. He probably was up late watching TV and running up the room service charges. Umm, his body feels good, though, and I squirm against him a little, getting my hundred dollar's worth.

A couple minutes later my contact with him makes Dickie open his eyes slowly, then he jerks his head when he sees me. Only for a second, though, before saying. "Let's talk business. What are you up for? And, um, the paddling is mandatory. I had to go through some trouble borrowing the paddle." 

Putting my arm across his chest, not moving away from him, I mumble, "I kind of want it all, Dickie. The make-out, sucking you off, then a dominant fucking." He goes, "And the fifty dollars paddling before and after." I mutter, "But, um, I already paid for the paddling." He snorts, "Don't try nickel and diming me. That was before sleeping with me. And, you still get the after sleep paddling when we get out of bed, but you still need to pay for the new date's before and after paddling."

Oh, jeez, that got my submissiveness reactivating, and I go, "Oh, yes, of course, Dickie. Sorry." He says, "Order lunch for us, and then I'll paddle you, and we can get the making-out part done while we're waiting for lunch." I'm like, "Okay, but what should I order for your lunch?" He's pushing me away from him, muttering, "I want a cheese pizza." 

Getting out of bed, I call room service and order what he said, then nothing for me. Dickie's got some excellent dominant vibes going for him this morning, and that's what I'm concentrating on, so I'm not hungry. I haven't been in the mood to be this submissive in quite a while, and it's kind of exciting to revisit it to this degree.

I look over at Dickie when he says, "Get in position for your paddling." Wow, it's like an electric shock just ran through me as another submissive vibration resonated in me. Quickly, I bend over, grabbing my knees, and push out my ass so he has a level target to hit with the paddle. Out of bed now, he mutters, "Stay," and he goes into the bathroom. I'm quivering with anticipation but grinning to myself because this is cool, hot, and submissively sexy. I'm in the mood for this sub/dom experience, as I said, and obviously Dickie's entirely up for it as well.

I hear him taking a piss, then washing his hands... that's good. He comes back into the bedroom, saying, "I should have thought to ask if you wanted some golden shower play. I mean, before I took that piss. Do you?" 

Holy shit, I'm really into my submissive role, gulping, then mumbling, "I'm up for whatever you want to do." He swings the paddle twice, then says, "We'll add the cost up when we're finished with this sleeping date."

He gives me four paddles, "Swoosh," "WHACK!" four times, then he leans the paddle against the bed, muttering, "Stay like that." My eyes sting but I'm far from crying. I've experienced much worse pain than that, but it still made me sweat and my eyes watered getting salty perspiration in them. Anyway, the paddling did its job of getting me into a perfect, deep, submissive frame of mind. So much so, I wouldn't think of moving my hand to wipe away the leaking tears.

Dickie pulls on his three-inch-oddly-big-headed penis, saying, "Okay, we'll plan our new escort date now that the sleeping with your escort is completed. Um, a new round of paddling before and after cost you fifty bucks, the two-minute make-out is fifty, then I'll do a quick urine play of some sort for you which I'll only charge fifty for, then fifty for sucking my cock, and a hundred for a hard dominant fuck on your ass. Is that about it?" 

I can hardly find my voice to say, "Yes, Dickie." He goes, "It's pretty much like yesterday, meaning the total is a bargain at three hundred, and that is a steal, honestly! You can stand now and get me my money."

I quickly do that, and he puts the money on the bureau with the first hundred and fifty. "I changed my mind. We'll have lunch before we start. You've just been paddled; another round is unfair to you." 

Nodding at him, he adds, "Are you feeling submissive? I mean, I'm doing my best here." I say, "Yes, Dickie. It's working this morning." He mumbles, "Good, I thought so," and he wraps his hand around my stiff dick, stroking it twice, murmuring, "That paddling gave you a boner." 

I didn't realize I had a boner until this second. Maybe I'm connecting the paddling to the real thing from Sandy that's doing some good. Right now, it feels recreational, having sexy fun.

Letting go of my boner, he grins, "I won't charge you for those couple of boner-strokes. Anyway, I was off my game during the early stuff yesterday. I wanted to make it up to you today by being extremely dominant." 

I don't feel like talking, so I nod, and he says, "Come with me." I follow him to the bedside table, where he pulls some tissues from a box and wipes my tears, murmuring, "You're a pleasure to service, so I almost don't feel I need to mention this, but I will anyway. Um, don't forget a nice tip when we're done. I get to keep all of the tips I receive." 

"Yes, Dickie."

Done wiping my face, he says, "Okay, then. Um, I need to check in with my main man now. Richard's been known to leave work early, so I know he's there now. Turn around," 

I don't even give a thought to ask why; I just do what I'm told. He goes, "Uh-huh, there are still two welts on your right butt cheek that haven't gone down yet, so lie on your stomach on the bed while I take care of my daily call to Richard."

Lying on the bed, my ass still burning a little, but nothing too serious. I again think back to when Bruce paddled me as his recruit, and he didn't hold back. These pussy boys realize they're paddling to get clients like me submissive. That's what we're paying for... a sub/dom sexual experience. Sandy's paddling is because Richard wants it done for disciplinary reasons. They all do a good job of keeping any contempt they feel for pathetic submissives like us out of their eyes. I imagine they, like most people, including me, can't understand why anyone would want to feel submissive on purpose. 

Not in a sexual way, but many people feel submissive to someone in a higher position than themselves, and, while they don't like it, they need to be that way for their job or for some other reason, such as living under a dictatorship with no human rights.

Dickie talks on the phone for maybe five minutes, then says to me, "Last night it was forty-five minutes before room service showed up, so I changed my mind again. Let's finish the two-minute make-out; then, after lunch, you'll get your first paddling for our second session. After that, I'm not sure, but I'll probably get the golden shower out of the way, too." 

Hmm, I like his confident attitude and the way he definitively says everything, knowing I'll do whatever he decides. That's how it should work in sub/dom situations, within reason, of course. So, knowing my role, I immediately get off the bed, ready to do what I'm told.

He says, "The difference in our sizes makes it harder for me to do a proper make-out with you, and I'd be within my rights to add a surcharge of ten percent, but I won't because you're a cooperative 'S' type client. Some aren't, if you can believe that. I mean, they defeat the whole 'effing point when they start complaining and not doing what they're told." I'm nodding, still not talking, just enjoying this dreamy submissive world without responsibility other than doing what I'm told. He asks, "How's your ass? Can you sit?" I reach back and feel both butt cheeks, mumbling, "Yes, Dickie." 

He has me sit in the arm-less desk chair; then he sits on my lap facing me and grins, saying, "I feel like a little kid sitting like this." He may feel that way, but he doesn't make out like a little kid once he starts. I can't remember anyone making out as hot and sexy as Dickie. His arms around my neck, he almost convinces me he's hot for me. He has a perfect size, very pink tongue, perfect firmness, and it's very active. Soon he needs to shimmy his ass back a little on my lap because I quickly get a hard boner sticking up between us. His make-out leaves me gasping and grabbing my boner as he gets off my lap, saying, "Don't touch yourself." 

My hand comes off my boner, "Put your shorts on so you can answer the door when room service gets here." As I grab my shorts, there's a knock on the door. Dickie mutters, "Oh, this is much faster service than I got last night." 

He's still naked, so he goes into the bathroom as I open the door. An older waiter rolls in a cart, saying, "Your lunch, sir." I sign for it, leaving my usual large tip, which he doesn't see because he's too polite to look. It'll be a pleasant surprise for him when he's outside the room. Dickie tells me to pull the armchair over as he sits on the desk chair, then asks, "Didn't you order anything for yourself?" Shaking my head, I say, "I'm not hungry." Shrugging, he digs.

Dickie is an accomplished, friendly, and dominant partner. He takes good care of his clients, or maybe he simply likes me. All I know is that he's taking good care of me. I feel good, I feel submissive, and I'm excited for what's coming next. And, yep, today I'm most definitely getting my money's worth. 

After lunch, Dickie's brushing his teeth, and I go into the bathroom to piss. He rinses his mouth, then says, "After you wash up, brush your teeth," and holds out his toothbrush. He's the second or third pussy boy who insists I share their toothbrush or mine, which is something I wouldn't think of doing normally. In my current frame of mind, however, I don't think of not doing it.

Finished with that, I get paddled and slip right back into a deep, dreamy submission to Dickie, who's very relaxed and comfortable, taking his time doing everything. He reads texts that come in on his phone as I wait on my knees, rubbing my paddled ass, ready and eager to suck him off. Finally, after texting back to a few people, he walks over, his tiny penis bobbing with each step as the oversized head seems to get the skinny thing moving. 

Standing in front of me, he says, "Pick it up and put it in your mouth." When I do that, he pees in my mouth for about five seconds, and I swallow three times. He says, "Ahh, I was holding that in for you. Later, if you want, I can pee on you in the bathtub, but it's up to you. I've had clients; all I did was drink iced tea and pee on them. Crazy!" 

I've enough sense that I'm not doing that! Instead, I lick and suck his cock and balls until we both have hard boners, then he grips my ears like last time,  humping his hips fucking my mouth, his cock sliding back and forth on my tongue, my lips-covered teeth clamping on his short penis shaft until my climax shoots cum out from my hard boner in a long stream between his legs. Then he blows a large load of cum in my mouth, and, again, I need to swallow three times clearing it all out.

He grunted and groaned, "Oooh, fuck, yeah," when he climaxed, so he enjoyed his work. He mumbles, "Stay," and gets tissues to wipe his dick, then, using the same tissue, wipes cum off my chin and at the edge of my lips. We put on shorts, then drink nine-dollar cans of beer from the convenience bar, smoking cigarettes on the tiny balcony as he rubs my back, talking soothingly about me being his favorite client ever. It sounded a little too, um, rote, as if he said it to all his clients, but it kept me in my submissive frame of mind.

I'm in a daze and losing some time because the next thing I know, Dickie is fucking me fast and hard. The hard sloped ring-type thing at the bottom of his penis's head is causing havoc with my prostate, wave after wave of pleasure soaring from it as I'm going, "Um, um, um, um... Dickie, oh, oh oh..." Then cum comes roaring out my straight-out boner to make a little 'Splat' sound dropping on the hardwood floor near the door. It felt like it came roaring out, but it was just a plop of watery cum.

Then Dickie wants me to hurry to get dressed, telling me, "Rent this room another day and arrange another escort date for tomorrow." He's getting dressed, too. Then, I find myself in the hall outside the door, alone. I'm dizzy with submissiveness, smiling, my feet barely touching the floor as I walk to the elevator. 

What an excellent escort date! Dickie's the very best! Oh, man, that was perfection for a sub/dom pussy boy date. I can't think of a better one. At the front desk, I rent the room for two more days, Saturday and Sunday, because Bruce works both days. Oh, God, I feel good walking out into a day that's clouding over. Dammit, not today! I want to sit on the beach in the sun and relive this date with Dickie.

In my car, my buttock still tender, I do what I'm told and call Richard to reserve Dickie for tomorrow. Richard handles it very professionally, saying, "I'm happy your escort pleased you. Would you like me to use the same credit card number?" I say, "Yes, please." He goes, "Thank you for your business. You're all set for tomorrow, sir."

Cloudy or not, I go to the rental tent and rent a chair, asking the old codger, "Where's Markie?" He goes, "He'll be back tomorrow." Which didn't answer my question, but I'm still feeling too docile to press the point. Going to my spot on the beach, I sit on my paddled buttocks and marvel at how well the date with Dickie went today. Horny? Ha, get serious! I'm not horny! I feel marvelous. 

The sun peeks out behind the clouds, and the seagulls do their squawking. The ocean does its rolling waves that run out of steam and retreat endlessly back to the Atlantic Ocean. Experiencing the beach, I feel wonderful. I'm chilling, waiting for my best friend, Bruce.

To be continued...

by Donny Mumford

Email: [email protected]

Copyright 2024