My summer of sex with Cowboy

Chapter 44

Sunday morning, Bruce's cell phone alarm wakes us at five o'clock. We moved apart while sleeping, so I slid next to him, and he put his arm around me, muttering, "Good morning, best friend," reminding me we're primarily going to be friends from now on. Well, I understand, I'm committed to being Jon Scheyer's recruit, and Bruce knows how much fucking goes on between mentors/trainers and recruits because he was a mentor/trainer, and I was his recruit.

We never forgot that, but I was trying to make us become boyfriends and maybe lovers, which was a mistake. He knew he wouldn't be able to be my boyfriend, not really. At least not for months and maybe years, and I knew that, but I tried to force it anyway. He needed time, lots of time, to get over what he'd been through so far in life.

I mumble, "Good morning." Then, not sure what I should say, I mumble, " Um, is waking up this early beginning to bother you? It's so early, I wonder if..." 

He shakes his head, "Nah, I feel good about getting up this early, about everything! I don't mind getting up this early. I don't mind waiting on tables, either. I'm finally grateful to be living a real semi-normal life. I pinch myself to be sure it's not a dream, and it's not; it's happening for me because of your kindness and generosity.  And now you've removed another stressful aspect of life in that I don't need to stress about relieving your almost constant horniness. You're going to be in the right place for that. Us being best friends is another blessing that I'll never be able to repay you for."

I'm like, "Wow, that's, um, I don't know what to say. I used to, but now I don't." 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 into the bathroom. I pull his pillow to my face, inhaling his subtle scent. I still love him, but it's morphing into a brotherly love. I think, oh geez, I don't know...

Oh, shit, then I remember my paddling date with Sandy at Eli's apartment/office. Jesus, I have a full body shudder and get out of bed with a partial stiffy. That's what I get thinking about how submissive I get after my paddling, but ironically without a stiffy then. After getting paddled, my dick looks like Cameron Hill's dick. Shriveled up and tiny. All our manhood is paddled out of us, and we're docile, submissive, and anxious to do what our mentor/trainer tells us. That's the idea; the punishment aspect is a side benefit.

I've dozed off and am awake when I hear, "Let's go, Zack!" My eyes pop open, and I see Bruce pulling the Cafe T-shirt over his head and 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 in my pussy boy uniform and into the kitchen just in time for Bruce to hand me a take-out cup of coffee, saying, "Oh, boy. You look nice in your uniform."

We're quiet as I drive through 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, "That's a best friend kiss. They kiss, right?"

I grin and nod, and then he says, "Good luck today with, um, you know. I know how much paddling can hurt. Oh, and I'm working again tonight, but you'll be done with your training by four thirty, I'd imagine, so that I could have gone home with you."

Nodding again, I say, "Yes, but I can't guarantee I'll always be available at five o'clock, so I'm buying our family a second car. Then you'll have a ride whenever you need it, whether working here or at the UPS Store when that gets going."
"I'm excited about that, Zach, or, haha, should I call you Ziggy. I'll work the business but split the money with you until I've paid you back. By the way, I'll need to be away training fo a month. We'll talk about it. Let's start in October instead."

Wow, he is excited! I say, "We'll work everything out. Have you noticed we're switching roles? You're legal now, and I'm not exactly legal, but we're both excited about our futures. Have a great day."

He smiles, pats my shoulder, and says, "You too. Love you, bro!"

Watching him jogging up the ramp to the boardwalk, I smile because he can love me as a friend but not romantically. Okay, I'll settle for that. I've got two hours before I meet Sandy at Eli's apartment building, and Anne's cafe won't open for an hour, so I'll drive to the cafe I ate at yesterday, which does open this early.

It pisses me off that I'm shaky and a little bit scared about the third day of being paddled. Sandy doesn't give me a break. He puts a lot of effort into swinging that fucking ping-pong paddle. And it's not a ping-pong paddle. Yes, it looks like one, but it's twenty percent bigger and twice as heavy as a regulation ping-pong paddle. 

This is frustrating. I'm not acting like a Navy Seal. I'm like a wimp, but I can't help it because I've had experience from Bruce paddling me. Four paddles is one thing. Six paddles are twice as bad as four. The pain accumulates from paddle to paddle, and I've never had seven. Jesus, that scares me because I had tears in my eyes yesterday. What if I actually cry like some cunt one of these mornings, unable to take it anymore?

That would be so humiliating! Well, fuck, I'd need to leave Atlantic City. No more negative thinking, though! I'm going to do it without complaining or begging. I need to if I expect to move forward. Considering the pussy boys I've hired, the idea that I couldn't qualify to be a pussy boy is unthinkable!

In the cafe, I'm too fidgety and nervous to eat anything substantial, so I drink a coffee and eat half a plain donut, stretching out the time so I only need to wait ten minutes for Sandy to arrive. When I see him coming, I stand straight, then mumbling, "Good morning, sir." Sandy frowns at me, and I think it's because I'm wearing the pussy boy uniform. I don't feel I have the right to say anything and now he tightly grabs behind my neck and pushes me in through the first door, then unlocks the main door, and up the stairs, we go to Eli's apartment, then to the punishment bedroom.

Johnson has just finished paddling the kid named Cameron Hall, and I see Cameron has pissed himself. Well, not himself. There's a bucket under where our dicks hang when we're incapacitated across the desktop with our dog collar attached to a hook on the floor. Cameron's bowels gave way, and all the piss in his bladder drained out without him being able to stop it. The room smells like piss.

Johnson, Cameron's short, stocky, African American mentor/trainer, shrugs and says to Sandy, who is still gripping my neck, "The kid lost control of his bowels. This is his last day getting paddled, so that's a shame. The pain builds up and..."

Sandy interrupts, mumbling, "Yeah, I know. I've seen it happen to everyone I've disciplined who goes two weeks getting paddled every day. Hey, did you see the Phillies last night kicking the Met's asses. Holy shit..." and they chatter about that baseball game until Cameron dick stops drooling piss.

Johnson unhooks Cameron's dog collar and helps him stand. Tears all over Cameron's face as Johnson says to him, "Let's go, Cam, open wide," and then takes out the ball gag, handing it to Sandy. I open my mouth wide without being told, hoping for brownie points. Sandy presses hard, getting the sloppy ball gag inside my mouth. He attaches the Velcro straps behind my head, and I begin gagging like mad again. 

My eyes are wide open and tearing as I'm making lots of gagging noises, staring at the tiny shriveled two-inch penis on Cameroon. Sandy is fastening the sweaty dog collar around my neck, mumbling, "Hey, Johnson, have you ever eaten at that Italian spot near Market and Vine?"

I can't breathe with the ball gag on my gag reflex area and the dog collar tightly on my Adam's apple. Sandy drags me over by the leash and pulls me onto the desktop, fastening the leash on the hook on the floor, totally immobilizing me. Gagging, my flaccid penis over the piss bucket, I jerk my head up a tiny bit, moving the collar just off my Adam's apple, but I'm still gagging from the ball gag. Sandy's saying, "Tony and I, you know Tony, right? That big-ass Italian with the six recruits in Cape May. We went there for dinner, and..."

My eyes are watering, not crying, watering, and I'm using my throat muscles to move the ball gag a little. My gagging lightens up, but not completely, and I hear "WHACK!" and the pain immediately rolls over me. It's already worse than the third or fourth one yesterday. The next one is worse, and I feel my dick shriveling and going inside my body. Maybe to be safe. By the fourth paddle, all I'm concentrating on is not peeing like Cameron did. I'm a fucking ex-Navy Seal, for Christ's sake, I don't pee my pants!
The sixth paddle, and I suppose one could call what I'm doing crying, but there's no boohooing or begging coming from me. Sandy says in a bored-sounding voice, "This number seven paddle is for not getting a passing grade yesterday from your trainer." 

What? I jerk, grunting, "No, I didn't do..." "WHACK," and I scream into the ball gag, then make a gurgling sound as my bladder lets go, and I'm dizzy and humiliated. I heard someone giggle, but it didn't seem to be coming from this room. Outside the room as the unmistakable sound of water dripping on water... my piss dripping onto Cameron's piss in the bucket .
The pain was constant, the humiliation almost unbearable, but I began dealing with it until I begin screeching not sounding human when Sandy sprayed the alcohol-based pain-reducing spray on my swollen buttocks. Then, ten seconds later, tears rolled from my eyes, so grateful the pain was numb and almost gone. I knew a version of it would be back an hour from now, but not nearly as bad as it was ten seconds ago.

My bladder had emptied because Sandy was now unhooking my lease and pulling me up and off the desk. My legs are wobbly, and I didn't notice Cameron being wobbly, so I concentrate on being steady as Sandy takes out the ball gag, handing it to someone, then the dog collar, and I see another pussy boy trainee with a brand-new pussy boy haircut. Sandy says, "Empty the piss bucket and rinse it out.

I carry the bucket past the mentor/trainee who I recognized. He didn't recognize me, though. He was with Eli with that night in the bar with Bruce many years ago, I mean many weeks ago. He sounds nice explaining to the kid, "I'm putting the ball gag in so you'll know what it's like, and the same for the dog collar. You wouldn't normally need these items because you only get two paddles to show you what you want to avoid." 

I'm completely naked carrying the piss bucket all the way across the office, hearing snickers but not caring. In the lavatory, in a submissive trance, thrilled I'm not feeling pain, I empty the piss in a urinal getting splashes on my bare feet, then rinse the bucket out awkwardly in the sink. Returning to the punishment room, I put the bucket where it was and wait for Sandy to say, "Don't just stand there. Get dressed."

I hear the kid says, "Yes, but why do I..." as Sandy moves me out of the room and over to the front door, saying, "Make sure Jon texts Eli that you had an okay day. He forgot to do that last night, and that's why you got the number seven paddle. Your bladder will settle down in a while. I'll see you tomorrow morning." 

He pushes me out of the apartment's front door. As I go downstairs, I know I've been beating up this morning, and it's not so much as I'm extra submissive because of it. Well, I am submissive, but it's more like I'm beaten into submission rather than concentrating on the delicious submissiveness I feel for a hot, dominant top guy.

I don't know how to explain today as compared to yesterday and the day before that except to say it's different. I'm walking down a sidewalk, crossing side streets for about ten minutes before when a stranger calls to me, "Hey, you. Get over here." He's a middle-aged man wearing a suit and carrying a briefcase. What have I done now. I cross the street and timidly ask, "Yes? Did I...?" 

He asks, "How old are you?" I humbly mutter, "Twenty-three," and he asks, "Are you one of Murphy's boys?" 

What? It doesn't occur to me he recognizes the pussy boy uniform I'm wearing and is thinking about hiring me. I say, "No, I don't know anyone named Murphy." In my brain the old me is yelling, 'Tell this pompous ass to go fuck himself.' But the lightbulb finally goes on and I understand he thinks I'm for hire." so the new me says, "I'm one of Eli's pussy boys.

He looks at his wristwatch and mumbles, "Never mind, I can't fit you in tome-wise," and he walks off leaving me standing here. I'm starting to come out of my paddle-induced coma and ask out loud, "Where am I going," and a teenager on a bicycle yells, "Dude, get the hell out of the way when you see someone on a bike." 

I jump out of the way, saying, "I'm sorry," instead of asking, 'Why the fuck are you riding your bike on the sidewalk, you dumb shit?'

That was pathetic, apologizing to a fifteen-year-old who was the one in the wrong, not me. And it isn't that I'm pissed off and angry about Sandy paddling me as if it were nothing, not giving a shit about me. Somehow, they've convinced me that I deserve this discipline, maybe because of how I've been all macho and tough, beating people up whenever I felt like it. Not that they didn't deserve to get beat up, so maybe it was more my obnoxious arrogance that deserved punishment... my comeuppance for being like that. I know I deserve to be paddled. Perhaps I'm not upset because the boy I love paddled me almost as hard, so I must have deserved it then, too.

Well, I don't feel arrogant or macho now, nor do I feel like beating anyone up. I'll take my punishment and learn my place, which isn't any better or worse than anyone else's. I'm nothing special. In fact, I'm inferior compared to most of these pussy boys who have made the best of the rotten hand they've been dealt in life. I was born with a silver spoon up my ass, and all I've done with it is entertain myself by following Ronny's adventures irresponsibly.

Then I look around and '"OH!" I'm across the street from Jon's apartment. What time is it? Looking at my phone, still talking to myself, I say, "Eight-fifteen? All that happened in less than fifteen minutes? In less than five minutes because it took me ten minutes to walk over here."

I'm trying to think if I'm supposed to be here this early. Then, for the first time since waking up, I remember Derick fucking me last night and wondering if I need to confess that to Jon. Well, of course I do. Why must I, though? My brain isn't working properly. Looking at the apartment building, then at my phone again, I remember Jon told me to go right to his place after my paddling. 

I'm thinking more clearly by the minute. My buttocks feel numb, as if I had ten shots of Novocain back there. Inside the apartment, I can't go further without being buzzed in, so I use the house phone to call Jon's apartment. Someone buzzed me in, and Jon waited at the open door. I stood at attention, asking, "Is this too early, sir?"

"No, no, not at all. Come in, Ziggy."

He's wearing only jockey-style underpants with a pee stain where his smallish penis head rests. I walk inside, and Jon closes the door and hugs me, murmuring, "I heard you had a rough time of it this morning. I feel bad, Ziggy. Seriously, I'm sorry. Come into my bedroom, Benny's asleep. I've got some excellent pain-reducing cream that will keep the swelling down, too. Get undressed."

I'm in shock that Jon is so compassionate and sweet; it brings tears to my eyes. He says, "That's okay. Cry it out, Zig." Feeling relief because of my mentor's compassion, I blubber a little bit, and then, as I get undressed, I say, "Mentor, I need to confess something I did wrong. Um, I ran into that Derick guy last night after you dismissed me. It was on the boardwalk, and I tried to act like a pussy boy coming on to a stranger, but he turned the tables on me..." I went on to tell Jon everything that happened between Derick and me, even though it was a humiliating experience and humiliating to confess it.

Jon shakes his head, "It's good you told me about that, but do not let it happen again. Wait for me to okay it, and there will be opportunities to practice with guys who will help out, pretending to be clients. As a matter of fact, you'll get to blow Benny when he wakes up. For now, lie on my bed." 

His small bed is a pile of sheets and blankets, but I lie on my stomach and soon feel cool cream that feels wonderful. Cream that Jon is gently rubbing on my ass cheeks. This is unbelievable, and after the rough treatment at Eli's, I'm overwhelmed with emotion by how Jon is taking care of me. I've made the right decision to become Jon Scheyer's pussy boy prostitute. Omigod, I get this wonderful warm, fuzzy feeling all over. No one in my life has ever been this nice to me.

Jon gently rubs cream on both buttocks, in my ass crack, and then a few inches down the back of my legs to be sure all the hurt is covered. Then he washed his hands and lay with me, comforting me until I could cry. I never imagined Jon could be this considerate. He can be very dominant, and now I've experienced his other side.

 "How are you doing, Zippy?" Sighing, I murmur, "Jon, you've made me feel wonderful. I'm more relaxed and comfortable than ever."

He murmurs, "I'm wondering, Zippy, if we shouldn't maintain the seven-paddle routine till the end of the week. I know it's painful, but look how you feel now. I can tell you from my viewpoint that this is the best attitude I've seen from you. There's no hard edge under the things you do and say. Now, you're a pleasure to work with, and I think it's because the bad attitude has paddled out of you. You're not the first one to benefit greatly from the paddling. What do you say?"

I can hardly remember how bad it was after the grand treatment I've been getting from Jon. I mutter, "So, you think we should keep the seventh paddle, Zippy?"

 "Yes, I do, Zippy, because it puts you in the proper frame of mind to do the training and follow my instructions. As I said, it eliminated that nasty edge to your attitude. It canceled out that feeling you project that you're better than, um, others. It should be your decision, though."

He's so nice, I nod; "Okay, if you think it'll help me, Jon."
"It's already helped. Okay, that's settled. You'll get seven paddles for the next four days. Billy will be joining us at ten o'clock. He had a dentist appointment he couldn't reschedule, but let's you and I get started on your retraining. I got Benny to promise to let you blow him for fifty dollars." Then to Benny, "Are you ready, roomie?"
Benny sniffs, "Yeah, I can't go back to sleep with you two talking. I need the fifty bucks, except I got to take a wicked piss first." Jon says, "Hey, that will be another good experience, Zippy. You've swallowed urine before, right?"

"Yes, I have. It's sterile, so..." Jon nods, "It'll be a good start before you suck him off. Urine play will come up maybe once a week, so it's not real popular, but you need to know what you're doing when a client asks for it."

Benny pulls out his dick. It's a grungy-looking five inches with an enlarged head and a sore on the shaft. Jon mumbles, "Get over there, Zip, we can use this room. It's the strangest thing, but I'm okay with everything. I've got an incredibly positive attitude, and I want to impress and please Jon so much that I feel like jumping around the room. Instead, I get on my knees between Benny's legs and guide his penis to my lips; just the head with my lips tightly closed, and he lets loose a yellow stream of urine as Jon says, "Swallow right away and keep swallowing. I don't want you to get piss on the floor."
I'm gulping the piss down my throat as fast as I can, but some is coming out both sides of my mouth and running down onto my chest. Quite a bit of it, but none gets on the floor. He peed for a seemingly long time but Jon said it wasn't even thirty seconds. I sit back on my ankles, licking my lips and feeling proud. Benny mumbles, "You pussy boys are some fucked up dudes."

Ignoring that, Jon says, "Go right into the blowjob, Zippy." I put Benny's average-sized dick back in my mouth and stroke the shaft as I suck on the head, and it gets hard pretty fast. What is puzzling me is I'm not getting a hardon as I used to when sucking cock. I miss that, and then when I've got Benny fully boned up, and I'm holding his boner up against his belly so I can lick and suck his nuts, I feel my cock finally getting hard. Benny starts taking quick inhales and rubs my head as Jon says, "Turn around, Benny, so Zippy can rim your asshole."

Benny moans strokes his boner and stands to turn around, bending over his bed. My first lick up his ass crack taste vile, a total excrement shit taste. Same for the next three licks, but then the shit taste fades, and, as my cock is as hard as a steel rod, I get into rimming Benny's poorly-wiped-after-defecating asshole. Getting into it fast and sloppily, after thirty seconds, Benny grunts, "I'm gonna cum," and he does. His hips humping on their own, and long steam of cum shoots across the bedding, landing against the wall.

Benny grunts, "Holy shit!" and strokes his cock, his ass against my face. I lean back, then stand with my forefinger and thumb in my mouth, fishing out pubic or ass hairs, maybe both.

While I was doing that, Jon got dressed in his pussy boy uniform, saying, "You need two buy a pair of white, high-top sneakers, Zippy. That completes the uniform, not the sandals you wore here. Benny, still pulling on his dick, mutters, "Where's my fifty bucks?" Jon hands me my new pussy boy shorts, and I take out my money, hoping to find a fifty, but I only have a bunch of twenties and a bunch of hundreds. I give Benny three twenties, saying sincerely, "Thank you. Benny. I hope you'll let me do that again." He says, "How about every morning?" Jon says, "I'll decide that. Get dressed, Zip.

I nod, "Yes, sir." He says, "I appreciate that you say 'Sir' as a sign of respect for me, but I'm only a trainer/mentor and not a 'Sir.' Eli is a 'Sir.' Richard is a 'Sir.' You say, 'Yes, Jon,' to me, acknowledging that you understand what you're to do and that you will do whatever it is immediately."

"Yes, Jon."

Benny leaves the room to have breakfast. Jon says, "Close the door, Zip. We have time before Billy gets here for you to suck my cock, and then I'll fuck you hard as a reward for the way you've handled yourself this morning. I know you let loose your bladder, which is disappointing, but you showed the right positive attitude in everything else."

I nod, excited to have sex with Jon. He chuckles, and, as he's taking off his T-shirt, he leaves on his shorts and underwear, mumbling, "Dammit! I shouldn't have gotten dressed or told you to get dressed. You need to take everything off again."

When I'm naked, he waves his hand for me to come up on the bed with him, saying, " C'mon up here and get on your knees. I do that, and he mumbles, "Go ahead, pretend I'm your client who wants you to do everything. Start by pulling down my shorts and then my underpants." On my knees, gulping and licking my lip, I get my forefingers inside the waistband at each side of his jockey underpants, slowly pull them down, and continue pulling them down his legs and over and off his feet. His smallish cock and balls lie there, waiting for me. Of course, they're perfectly hairless. They're also slightly damp and sticky-looking after being encased in underpants overnight, and Jon is unlikely to have taken a shower last night.
His cock isn't even as long as Bruce's cock, but it's fatter. It is almost four inches but gets a little longer when erect. 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, and it's damp with perspiration, but it's Jon Scheyer's damp musky cock and balls, and I'm deeply into him. Bruce used to do this exercise with me.

"Go ahead, Zip, take deep inhales, get used to my scent. I do that, and it's a fairly strong scent, making my eyes tear up, and he says, "You need some practice on the full body worship, starting with my feet. Give them a good licking and work your way up one leg and then the other, eventually sucking my cock and balls. I want to feel shivers of pleasure, too." 

"Yes, Jon."

Going backward on my knees passed 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. Since my latest paddling, I've been docile and submissive even when I'm NOT doing sex, but doing submissive sex with my mentor/trainer gets me into deeper submissiveness than ever before, and it's an exotic,  beautiful thing. Like living in space without a care in the Universe, I'm in dreamy, deep sexual pleasure.

 Licking and sucking on Jon's left foot and leg, losing all track of time, saliva drooling down my chin; I lick, lick, lick his foot and leg. I lick up his leg so far that the side of his scrotum is against my cheek. I'd probably never stop licking this leg, except 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 a stone. I lick up his chubby four-plus inch cock, over the head and back down to the root, then pick it up and suck the head into my mouth. I'm licking and slurping on his cock, feeling like a fat wooden dowel sticking straight up. 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 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, and Jon's doing a little panting himself as he rubs my head, 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, Jon, I loved it." He goes, "Did you get your money's worth?" "Yes, Jon." 

"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 sexually hot and aroused. It's as if I'm walking on clouds; I'm so mellow. Jon's cock is hard as he squeezes it, muttering, "Fuck, you almost had me blowing my load, and I'm supposed to be the 'effing pussy boy, not the client." 

Without thinking, my arms are around his waist as I lean against his small but tight body. He rubs my shoulders, asking, "Are you glad now that I added the seventh paddling?" I murmur, "Yes, definitely, Jon. It's exactly what I needed."

"Yes, you did. I told Eli and Richard I could tame your Navy Seal's obnoxious ways and turn you into a team player. Neither one had the balls to have you paddles like I did. Bruce tried and got closest, but he wimped out when he was on the right track. I knew what needed to be done, and there's a way to go, but I'll have you paddled into the perfect pussy boy before I'm done. You trust my decisions, right?"

"Absolutely, Jon. The paddling hurts, but I've never felt this good before, so it's working for me."

"Yes, I can see that. We're paddling all the negatives out of you, and you're smart enough to appreciate it. You even asked for the seventh paddle to stay a part of it."

What? He talked me into it, but I agree with him. I feel I'm where I need to be, under Jon Scheyer's total control. This feels so nice as he lightly rubs my head, shoulders, and back. I know he's stalling after almost climaxing. Hell, my old self I would have climaxed while licking and sucking his hot body. So, we're both recharging, getting ready for the grand finale. The grand finale for this morning, anyway. 

He asks, "Would you like me to do you bareback?" I say, "Yes, Jon." He adds, "I rarely do that, but we all tested monthly, not that I'm worried about catching something from you." 

Sounding reinvigorated, he adds, "Okay, here we go. Suck another good boner on me." He takes his hands off me, and I scooch down the bed, 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 hairless 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, the bed springs creaking, mumbling, "Hands and knees again." I do that, and he picks up a container of lubricant from a shelf. I'm uneasily on my hands and knees on the too-soft mattress with Jon going up on his knees behind me, pushing 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 super-submissive trance, murmuring, "No, Jon. You're my trainer, so whatever you want is what I want." He mumbles, "Spoken like a true submissive."

Feeling stable now that Jon's not pushing at my ass, I hear the container of lube being dropped on the shelf, 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 open me up little by little, and 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. I'm picturing his boner in my ass, and that thrills me, and the thrills continue as he slowly pushes the rest of it inside me, making me shiver and make a sighing sound, so contented it's ridiculous. This is worth more than a hundred dollars plus the twenty-five surcharge for my paddling.

Not that it's in, Jon murmurs, "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 rote-like voice. I moan, "Mmmm, feels really good." 

He humps against me, his hands gripping my hips, "I'm not expecting this to last very long, Zippy. I murmur, "It already feels amazingly good, and I can't ever remember a better boner in my ass." That's not true, but I like brown-nosing and complimenting Jon. He is so perfect!

Tightening his grip on my hips, he moves his slightly-over-four-inch boner back and forth and keeps doing it, getting my prostate involved. The entrance pain lingers, but I pay no attention to it as I'm in the hands of someone who knows how to fuck an ass awesomely. Jon does one pull back, the swollen head getting caught at the tight lips of my asshole, then he pushes it 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 Jon's fast-moving cock scratches all the way in and all the way out.

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 got a hard, steady rhythm going, "Slap, slap, slap," and "Ahh, ahh, ahh... ohh!" 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 Jon stops thrusting, leaving his 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 idling and purring stages. It's maybe thirty seconds more before he starts his hips moving again, doing that slow thrusting before picking up the pace as I gasp out, "Jon... 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 hard, and I feel his sharp stream of cum hit inside like a stick poking 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 Jon casually mumbles, "Push your ass up. Get it up high so I can see if the swelling has gone down." My buttocks are hot and stinging, but they feel really good, too, as I do as well. That pain-reducing cream is a miracle worker. How wonderful the last hour has been after the five-minute paddling. That paddling was so worth it! I know, I keep saying that, but it's true!

He says, "Lie beside me until Billy gets here. We're done with the pussy boy escort service for you. The rest of the day I'm your trainer/mentor, but you do owe me for the sexual service. Let's make it an even two hundred which includes the tip.
Sighing, I get up, saying, "It was worth more than that, Jon." I'm smiling because this morning in Jon's bedroom was a special experience. I get two hundred-dollar bills from my shorts and give them to Jon, murmuring, "Thank you, Mentor."
Join mutters, "Fuck, I can't lay here all sticky with lube and cum. Let's clean up in the bathroom." We do that and then get dressed in the bedroom. I sincerely say, "I'm proud to wear the pussy boy uniform. Jon. Some guy recognized the uniform and called me over this morning. He didn't have the time for a date, but he almost asked for one.

I pull out my money and get a hundred-dollar bill, murmuring, "You deserve a bigger tip, Jon. Here, please take an extra hundred." He takes it and puts it in his pocket, saying, "Don't expect you can buy your way into special treatment, but thank you."

 "Well, Jon, I don't expect nor want special treatment; I wanted to tell you again that you're awesome." He put the money I gave him earlier, and he dropped it on his desk in his pocket now, nodding, "Thanks, I'm happy you can afford me." 

He grins, "You're still experiencing heavy submissive vibes, aren't you?" I nod, "Yes, since I got here, I've felt them." 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. Jon acts confidently smug. We walk out of the room, and he says, "We'll have a cigarette outside waiting for Billy. Outside, lighting up, Jon says, "I believe you'll flourish as my recruit."

I stare at him, feeling in awe that I'm his recruit. Everything I've had to go through the past three days to be allowed to be Jon's recruit makes it all that more significant. With Jon Scheyer, I feel as if I'm in the presence of someone special who will do special things, and I'll be holding onto his coattails and experiencing them, too. I know that sounds like how it was with Ronny and me, but Jon is a more serious, special person than Ronny, or me.

Jon mutters, "Here comes Billy. I don't want either one of you taking advantage of me, expecting I'm going to be okay with you taking time off for things like a dentist appointment. Training with me is the most important thing either of you will do all day, every day.

"Yes, Jon." And I was sincere that I agree with him!

To be continued...