Special Delivery Pt. 02

As weekends go THAT first one was a stress. Once my post-sexual high wore off I realized I'd had engaged in random sex with a complete stranger who for all I knew was a certified psychopath. I would have put the whole thing out of my mind but the tang and taste of her ejaculate lingered in my brain long after it left my mouth.

For the next forty-eight hours, every dark scenario roiled my brain.

She was crazy...

She'd think I was crazy...

She was messing with me.

Normally masturbation was a thirty minute affair minimum, aided by a mix of pornography or the more vanilla sex examples of Japanese hentai.

Just thinking about Mommy's ass or tits had me blowing my load in under ten minutes, five if I avoided wasting time with my umpteen gigabytes of stored material which suddenly only served to remind me of how great ACTUAL sex could be.

Then on Sunday, I got a text message. A digital code for a high-end fitness centre near the downtown train station. There were instructions included if you want to call them that.

"Meet you first thing Monday, club opens at 630." Its curt tone did a lot to convey the dynamics of our newly established friendship. This was someone used to getting what they wanted whenever they wanted FROM whoever they wanted and right now I was what SHE wanted.

"What about work?" I texted back, though I assure you schlepping packages across the downtown core was far and away from my mind.

"I've taken care of it!" was all she wrote back.

Great, I might end up wishing I was the lotion-girl in Silence of the Lambs but apparently my work situation was settled, good to know.

Monday morning I got dressed, headed downtown clutching my workout clothes while conjuring doomsday scenarios, each one more dire then the last.

That nagging voice that talks you out of calling that friend that secretly masturbates while thinking of you covering their body in a glaze of cum, was working overtime to undermine the few tiny dregs of self confidence I'd woken up with.

By the time I got to the club I resolved to do a quick look around then rabbit as quickly as I could. I'd duck her calls telling myself whatever lie made ghosting someone who had sex with you when you felt decidedly UNSEXY a good idea.

There was a young lady at the front desk. Her lithe figure contrasted with the healthy chest which concealed the employee nametag. Though given the scoop neck on her front I'm guessing that was probably by design. She was cute in a pixie sort of way through her aura of ennui dragged down the hotness factor. She radiated boredom like heat from a campfire. She barely glanced away from her screen to scan my ticket. But then she saw something on the screen I didn't and looked, and I mean REALLY LOOKED at me.

"I was invited by-" I started.

"I know who SHE is," I caught the implied question. She didn't know who I was but given who I knew I must be someone, and if I was someone, becoming my friend just became her entire life's focus.

She rose to her feet, grabbing my arm escorting me further into the club. "Let me show you around sir."

I'm not a sir," I replied nervously, "you can call me Micheal."

"Of course, my name is Clare. I hope you'll let your friend know I was helpful to you Micheal?"

The slight hint of obsequious begging pretty much told me all the doomsaying of my superego hadn't come close to the worst case scenario.

Mommy was obviously someone with influence and authority who'd taken an interest in ME. Clare was clearly someone keen on earning that interest herself assuming she didn't already have it, the tone of voice let me know ghosting someone who could inspire that kind of cringing subservience was definitely NOT my best option.

She cling to my arm, chatting bubbly personality on full display; as were her breasts, which she made sure she was rubbing against me as often as possible. Remember how I mentioned I make jokes when I'm nervous, she was trying way too hard to find each of my quips absolutely hilarious which did little to quell my anxiety.

She showed me the aerobic training floor with shiny modern machines that could not only track your daily progress but would upload that data online so you could track how your strength and endurance changed over time via website and a smartphone app.

There was a members-only bar where a mix of hi energy drinks and low calorie foods could be purchased. I noticed a suspiciously well stocked bar. Clare assured me that I could get a stunning array of "mixed beverages".

There were three changing areas; two for the regular folks as well as a larger more opulent one for the club's VIP members. Though technically unisex, there was several rows of private booths the size of department store changing rooms so you could still preserve your modesty.

There was steam baths off the main Olympic sized pool a therapy pool next to that that was essentially a really long whirlpool with water heated up to a comfortable temperature but the VIP members had their own steam baths and whirlpool that resembled nothing less then some Greco-Roman style spa including attendants who's good looks insured the massage tables were always in use. The flushed faces and strangely familiar if odd noises coming from the massage booths hinted just what sort of VIP perks membership entitled you to.

We arrived back at the desk just as the elevator's door opened up and Mommy herself strolled out with a workout bag casually tossed over one shoulder and plastic bags in her other hand. She seemed taller than I remembered, a result of the thick heeled boots on her feet. A curve hugging set of black leggings caressed her thighs and ass while showing off her thick shaft looking cramped within the confines of her bottoms. Her outfit topped off with a silk bomber jacket emblazoned with the figure of the video game character Bayonetta on the back. The perma-smirk she seemed to always have was topped with a pair of cat's eye sunglasses that did not look like the seven dollar versions you could buy at any gas station kiosk.

She walked up to the both of us. Kissed me on my cheek before tossing me the workout bag, which I scrambled to catch.

"Clare, you've met my new friend and given him the tour?"

"Absolutely ma'am," Clare replied, "I showed everything we have to offer."

"I'm sure he wishes THAT were true." Mommy snorted, "Well I'm going to get warmed up. Why don't you run him through a basic aerobic session and we'll see if you can take the edge off of him."

"Thank you ma'am."

"Oh, ...and I know I'm asking a lot of you working with my friend so I got you a little something to liven up your session."

Mommy handed the young girl the plastic bags.

Clare looked inside and flushed a crimson shade. "Thank you ma'am"

"Do a good job with Micheal and I will be very happy to show you my gratitude for the hard work."

"Hey, I'll thank you myself," I replied.

Mommy chuckled, "Lets see how your stamina training goes before we talk about how much gratitude you can show."

Mommy turned to Clare, "He'll be on the training floor in ten minutes."

The woman blushed and dashed away clutching her bags.

"You have any problems getting here?" Mommy asked.

"No problems," I answered.

"You've been thinking about running since Sunday night."

"Of course not!"

Mommy captured my face in her strong hand. Just the aura given off by her presence gave me a weird feeling. A slightly kinky friend called it 'putting you in subspace'.

He required a few hours of cock and ball torture or a weekend long edging slash orgasm denial session after being locked in chastity to get there.

Mommy could do it with a glance. It was like she knew my deepest secrets; like she KNEW how often I'd cum while dreaming of the taste of her creamy discharge.

"First rule Micheal, never lie to me. We can have a lot of fun, but only if I can trust you to always tell me the truth." She said softly, "you were thinking about ghosting me?"

"I was thinking about ghosting you," I answered, "though I kinda thought you were fucking with me so it wouldn't be ghosting you, it would be me not falling for whatever the scaaa- ... I mean whatever it is that's going on."

She looked at me, obviously she knew where that sentence had been going before my sense of decorum kicked in.

"And now?" She asked dryly.

"Between this place and Clare, you still kinda intimidate me."

"But you're not running."

"My dad grew up in rattlesnake country. He used to tell me that there's a difference between being scared and being anxious before something big that's going to change your life like marriage or a new job He called it having rattlers in the belly. He told me any time I get rattlers in the belly I gotta hold on tight."

I looked at her, "For some reason you give me HUGE rattlers." I finished.

Mommy caressed my cheek, "Good boy, there's rewards for being straight with me."

"Which reminds me. Clare asked me to tell you if I had a good time. So this is me telling you I had a good time."

The transwoman snorted, "You've had a quick tour of the facilities and met a pretty Tgirl," Mommy commented dryly, "your day has barely started."

"Then let's see if I can go the distance," I replied.

Mommy laughed, "By the way when you get out there tell Clare I'll have my phone with me, ok?"

"Okay?" I replied suspiciously. Being a millennial, the idea of NOT having a smartphone or similar device within easy reach was practically unthinkable.

Mommy gave me a look that practically screamed "kids these days,"

"She'll know what I mean." Mommy replied with a grin.

8

9

8

I thought I was in ok shape, endurance-wise anyway. Clare's instruction put THAT thought right out of my head.

She eased me into it with a few simple stretches. I noticed she was standing particularly straight while swinging her arms gently so I emulated her as much as possible. It felt odd to have my back straight and chest forward but I figured that was down to generally poor posture.

We moved onto walking the treadmill, as a delivery courier, walking from place to place was ninety percent of my day-to-day. She kept me on there for what felt like hours but was surely only a few minutes. Apparently all she needed to do to make things tough was add the slightest of inclines to the treadmill. My legs were screaming the vilest curses at me via the pain running the length of my tortured thighs and even into my feet. She was very encouraging and it seemed like she was working up a decent sweat of her own.

We did planking and a kind of reverse-crunch. I felt the muscles of my stomach whining in protest. Clare moaned and grunted as she did each movement with me. I tried to not ogle but I started to see something odd, a weird almost unnoticeable protrusion along her bottom. I figured I'd better stop before I made her uncomfortable.

We moved onto cycling which I enjoyed though not as much as Clare did. She was bouncing atop the thickly padded seat or grinding against it and I started to hear an odd buzzing sound following us around the training floor. I thought it was the speaker system so I didn't comment.

She eventually let me do some simpler weight training though she made sure she was spotting me. I started with forward presses, some lat pulldowns and several arm curls. At one point she stepped close to me to help correct my form. As she pressed up against my side to make sure I was "properly holding my core...", I felt the oddest thing, a tingling sensation seemingly coming from her upper body.

I felt it a few more times and to lighten the mood, remember, humor as a defense mechanism to alleviate anxiety, I decided to joke, "Someone really REALLY wants to talk to you."

"Wha...what?" She sounded distracted.

"Um, you're buzzing, your smartphone I guess, don't worry I won't tell anyone of you need to slip away and answer it."

"It's okay," she replied, "It's not a phone."

We kept working out, doing leg curls, leg presses and switching things up with an endless rope pull. That buzzing, just on the edge of my hearing, was clearer now.

"What's up with your speaker?"

"Huh?" Clare asked, sounding distracted.

"Your speaker," I answered, "I've been hearing a buzzing sound following us around."

I noticed she was standing with her legs crossed and twitching visibly. She swayed back and forth and I suddenly noticed the buzzing seemed to lessen when she did so but never went away. That's when I realized, I only heard it when she was standing close by.

"Why are you buzzing?" I hissed.

She shuddered, biting her lip as she choked out a soft answer. "Considering who you came here with, do I really need to explain?"

"Fair point, five minutes after meeting her for the first time I was on my knees swallowing one of her hot loads and five minutes after that I was out the door because, and I'm quoting directly here, 'any longer she'd have been balls deep in my ass...' and I can't say she was entirely wrong about that idea."

Something about that idea clearly excited Clare who moaned softly clutching my arm. I could feel it now, vibration coming from her waist and chest.

"So how does this work? I assume she's got some kind of remote control?"

Clare nodded, "I'm uploading your results. Whenever you do a rep set faster or longer she adjusts the power."

"So the better I do," I mused, "the better she makes you feel."

The transwoman nodded.

"So you need me to do well enough that she let's you cum but not SO well that you wet your pants on the training floor."

"I'd be lying if I didn't admit I wouldn't have the biggest problem with THAT scenario."

"I'd love to help out but I'd rather NOT end up an aching muscle zombie for the rest of the day."

Clare bit her lip and nodded, obviously the powerful sensations going through her body made it difficult to speak.

"Then let's go through all the exercises again and we'll shoot for better times on all of the tough ones."

"Why would you ...uh, help me out?"

"You're wearing vibrating nipple clips and what I have to assume is some kinda anal thing and you're still giving me a run for my money. I'm learning a lot from you, the least I can do is make sure you get something out of our time together."

Clare and I cycled through the training floor again. This time I concentrated on pushing past my times and reps. When I couldn't do heavier, I'd do more. I realized that Mommy was probably not just monitoring MY progress but also using the info Clare sent her to know when to adjust the power of the toys Clare had in her and on her.

I'll grant Clare this, for someone with vibrators up her ass and clipped to her nipples she was surprisingly professional, attentive to both my form and efficiency.

She'd often stop me when I was doing something wrong and make me repeat the movement until I got it RIGHT. She said it was because she wanted to avoid being punished by Mommy. I believe it was because underneath the sexual masochist was a very knowledgeable and professional personal trainer who wanted to EARN her orgasm the right way.

Eventually, Mommy herself strolled through the training floor saying hello to a few individuals before stopping before me.

"How's our newest member?" She asked with a cocky smirk.

"It's great," I replied, "I love this place; wish I could afford to actually be a member here."

"What do you think Clare?" Mommy asked as if the transwoman wasn't climaxing next to her.

She seemed to be struggling for her words, her thighs were clamped shut and she was barely controlling her twitching.

"His form needs work," she finally grunted, "and he should practice everything we worked on until he's got it down pat."

"You know Clare I really REALLY appreciate your taking the time to work with Micheal here." She trailed her hand down Clare's back grabbing her bottom and squeezing her meaty rear end causing the young girl to gasp and whine while wriggling and grinding her ass against Mommy's hand.

"Micheal here has an errand to run for me later, any chance you and I can discuss his workout plan. I'd really like your input."

"I'd love to talk ma'am."

"I think she's looking forward to YOUR input." I snickered.

Mommy turned and caught my eye in her powerful gaze. Whatever dark wonderland she already had planned for my asshole, that crack had just earned me a whole NEW series of red delights.

"Then it's settled," Mommy replied to Clare while looking at me, "you'll meet me for a quickie lunch date in the hotel in a half hour. In the meantime Micheal and I have things to discuss so if you'll excuse us?"

"Yes ma'am."

"Oh and Clare?"

"Yes ma'am."

"Don't take them off yet," Mommy said, "I honestly don't care if you end up wetting yourself, as a matter of fact I might enjoy it if you do. I'll remove them MYSELF is that clear?"

"Yes ma'am." Clare whined

"Good girl, off you go." Mommy chuckled, "oh and Clare?"

Mommy held up a small device and touched a button; Clare shuddered, moaning as her eyes rolled back in her skull.

"A little something to make sure you remain focused on...your work," Mommy said with a smirk.

Clare nodded and literally stumbled away from them.

"Now, time for a quick shower," Mommy declared, "you've had enough exercise I assume?"

"For now anyway," I answered, "I assume my muscles and joints will be lodging a formal complaint with management in the morning."

"Try swimming, it's low impact, works your whole body and won't cause you too much stress."

"You want to go swimming now?"

"No right now I want to shower. I was suggesting an activity for tomorrow if you aren't up for a full workout."

I shook my head, "There's no way I can afford a membership to this place." I replied.

Mommy paused, "Ah, I see the source of the confusion. You already HAVE a membership."

I crossed my arms, "I can't afford this place," I answered, "Are you sure you want to do this?"

"Are you sure YOU want to do this? She replied.

"I feel like the T-girl with an ass full of vibrator and panties full of cum should be a red flag but I'm still not looking for the door."

"Good boy!" she chuckled, "now I've arranged for you to be my contract courier. That will let you be where I need you to be, whenever I have need for you to be there."

"You said you had a job?"

"Pick-up and delivery, in this case there's a package coming into the island airport." She explained, "I need you to take the ferry to the island, pick it up and bring it back to the hotel."

"Ferry boat runs are a guaranteed C-note."

"And this is premium so be a dear and hop to it."

"I'll be back here ASAP."

"Be back inside of an hour and I may have a surprise for you."

"I'm not sure I'm ready to wear a vibrating chastity belt."

"That ass is far too precious to me to waste toys on it."

"Well diet and exercise take time and you don't strike me as willing to wait THAT long for a piece of ass."

"Oh I'll claim your ass in due time," Mommy replied, "but yes I have one or two people I'd like to show it off to; hence WHY I'm paying to make it nice, tight and even more fuckable than it already IS."

Strangely enough finding out I was apparently some combination of fuck toy and arm candy made me much more comfortable with the situation.

8

9

8

So-called Ferry Runs were a delivery courier's wet dream. There was a busy commercial airport tucked away on a string of islands in the middle of a vast lake that gave a beautiful view of the city's Harbourfront. The only way to reach it was via the island ferry which traversed the watery route multiple times per day. Couriers who did the ferry run automatically made more money for the trip ON TOP of whatever they earned for the service level. This was because it was generally assumed that you'd be either waiting to get TO the island airport or waiting to RETURN, either way the normally speedy service promised by our company was very much at the mercy of bored municipal employees with ironclad job security.