Special Delivery Pt. 02

Mommy's arrangement meant I was going to pocket a cool chunk of change for what was essentially a fifteen minute boat ride which culminated at the airport itself followed by a fifteen minute ride back. I got lucky coming and going as ferries were just departing both times. If you got there at the wrong time though, the ferry boat crews might make you wait for half an hour or more.

I got the packages and headed back to the hotel arriving at the front desk. The bored concierge sent me up to Mommy's room where my "surprise" was waiting for me though I wouldn't have called it a surprise since I kind of knew it was coming. She opened the door and ushered me inside the room. Snatching the packages from me, several thick sheaves of paper, she looked them over sighing with an annoyed voice at their content before turning to me.

"Okay Sweetie," she began, "change of plans I'm going to need to move on this stuff right away so I have to leave but I booked this room for overnight so why don't you and Clare get better acquainted."

"You want us to..." the very idea made the words back up in my throat even as my arousal rushed to fill my suddenly uncomfortably tight jeans.

"You disapprove?"

I shrugged, "You're putting me up in a four star hotel suite to have sex with your Submissive. "

Mommy shook her head, "No I'm putting you up in a FIVE star hotel," she corrected.

She jerked her thumb over her shoulder, "-And if you think THAT'S a suite," She chuckled, "you've clearly haven't seen anything yet."

"What's the catch?"

"Why does there need to be a catch?"

"Okay now I am absolutely sure there's a catch." I replied, "I'll be honest, I'm kinda vanilla for ball gags and nipple clamps."

"You had your nose in my crotch and swallowed my load without breaking a sweat," she snickered, "you might not be as vanilla as you think you are."

"That's different, I've always been ...uh, accommodating when it comes to sex." I hesitantly explained, "especially if it'll uh, ...help someone else out."

Mommy rolled her eyes, "This is practical," she replied, scribbling something on a little card that she shoved at me, "I need your step and fetch skill-set first thing tomorrow, and I do mean FIRST THING. I want you at THIS address before the secretary arrives at 8 AM."

"Okay, so I'm on the clock," I replied.

Who would have guessed that a lifetime of customer service training would so adequately prepare me for being a co-operative Bottom Bitch.

"She'll know what to do and where to send you from there." Mommy explained.

"What about Clare?" I asked.

"What about Clare?" Mommy snorted, "I'd tell you to fuck the shit out of her but I've kinda taken care of THAT."

Mommy gestured towards the bed and I saw Clare for the first time secured, spread eagle, to the four poster bed.

"I've actually been a cruel mistress. I haven't let the poor thing climax even after fucking two loads of cum up her ass. You might want to start by cleaning her out."

I watched Clare's writhing form, something about knowing she had an asshole full of Mommy's cum made the idea of eating her ass incredibly tempting.

"You don't mind my sloppy seconds do you sweetie," Mommy whispered in my ear, "or is eating the cream pie from the asshole of my fuckslave too much for you, Vanilla Boy?"

"Please tell me that's not my nickname?"

"It is now," she giggled, "on my cell phone anyway."

I groaned, and she giggled at my discomfort.

"Clare," Mommy announced, "Mistress needs to tag out but I left you in good hands."

"Thank you mistress." The tranny sub replied.

"Is she gonna break my cherry?" I asked cradling my ass nervously, "Cause I kinda thought-"

"Good point, ...Clare," Mommy snapped, "I'm giving you and him A special treat for your hard work today but his ass belongs to ME. You two can have as much fun as you want but that ass is MINE to plunder, understand?

Clare whined.

"I'm not hearing you."

"Yes ma'am," she replied.

"Yes Mommy." I answered.

Mommy nodded, "GOOD, you kids play nice."

8

9

8

Mommy was barely out the door as I shed my clothes while Clare writhed on the bed.

"Did she really fuck your ass before I got here?"

Clare smiled seductively and raised her ass off the bed. Her cheeks flushed and slightly bruised, revealed where a skilled hand had reddened them with a spanking.

"She fired so much cum up there I think I can taste it."

But how did she keep you on the edge?" I asked. I kicked my shoes off and stumbled towards the bed with my underpants tangled around my legs.

Clare wriggled her waist and I saw a ribbon tied round her erection.

"So when I take that off..."

"You'll get a cock milkshake in the face or in your mouth."

I knelt on the bed cradling her full ass in my hands.

"Either way works for me." I replied.

She flinched as I touched her ass cheeks, her bottom still sensitive to the touch from the punishingly brutal fucking she'd already gotten from Mommy. I tried to be gentle, as I trailed soft kisses across the creamy soft expanse of her flesh. My lips circling closer to the coffee-coloured ring of her tiny hole. My kisses and licks let me taste her excitement. She moaned softly, fingers clutching at the air while my tongue circled back to the dark hole that pulsed and throbbed with my attention. Her breathing hitched and gasped as my tongue invaded her secret places. Her hips rose, writhing and pumping as if trying to pull my french kisses deeper inside. I started to taste something familiar. Mommy's cum, oozing down from wherever her lengthy cock had fired it, onto my searching tongue. Her moans were louder and more passionate. I heard whispered begging for me to go deeper and suck more of Mommy's creamy mess from Clare's well fucked hole.

The creampie started running out of her hole, a frothy mess that stiffened my own erection. I remembered the taste of Mommy's creamy cocktail from before and to taste it again even as second hand leavings from Clare's ass had me grinding my shaft into the bed. Her moans grew louder and longer as she thrust her restrained erection in the air.

I licked my hand and curled gentle fingers around her shaft and started stroking even as I kept my tongue and mouth working her anal passage, drawing gasps and moaning from her.

I pulled the end of the ribbon between my teeth and gently loosened the tie and she wailed as her shaft shuddered and pulsed as the long delayed climax unleashed a geyser of semen across my face. I opened my lips and took the remaining load in the warm cavern of my mouth.

Her hips pumped up as if trying to hilt her cock in my throat. I held her load in my mouth as her climax slowed down and finally stopped. Kissing my way up her stomach and chest I arrived at her mouth and her tongue entered and searched for the creamy treasure hidden within. I gave up the sweet tasting load letting her lick the dregs from the inside of my mouth.

We made out, kisses and touching revving our need for each other's bodies.

Clare rolled us over onto my back and she reached down to caress and fondle my hardness as it rubbed against her own. I pulled her face to mine and whispered in her ear.

"Feel like getting in trouble with Mommy?"

"She's claimed your ass," Clare whined.

"But what do you want to do?" I asked.

"I want to fuck you till you scream my name but she's got dibs."

"In my ass, I'm guessing she made a big deal to mention that for a reason?"

Clare smiled and reached over to the nearby bedside table. A bottle of clear liquid that had to be baby oil sat there and she uncapped the top and poured out a generous portion in her hands which she wrapped around both our shafts and started stroking them both while cowgirling me.

"I want to fuck you so bad," she gasped, "the second she let's you off the leash, you gotta come find me so I can rail that ass."

It was my turn to moan and gasp as my shaft and hers slid into and all over each other. The oils kept our shafts slick; and her grip on them drove my lust and need to spray paint her tummy and chest with my own creamy cocktail.

"God damn, I'm gonna shoot," I hissed.

I reached out, replacing her fist with my own. My hand started stroking again, this time the stroking made easier with the baby oil on my erect flesh. Clare gasped and whined thrusting between my slicked fingers. Our cries reached a crescendo as we came together. Some cum landed on my stomach and chest while more gathered on my hands. Clare lifted my hands and licked them clean before dipping her fingers in the creamy mess pooling in my belly button. Clare collapsed on top of my body. I could feel the sticky mess cooling between us.

"I need to up my stamina." I huffed and puffed, exhausted from our exertions.

"You'll get the hang of it eventually." She replied.

"Especially if Mommy has anything to say about it."

"Why do you call her Mom?"

"Cause apparently I have a mommy fetish," I confessed, "and as near as I can tell she's got one too or at least she blasted quite a load on me when I started calling her Mom."

"That one has a lot of fetishes," Clare laughed, "Hell ...her fetishes have fetishes."

We shared a laugh for a moment then kissed for a few more before Clare whined about how sticky she was feeling, covered in semen both inside and out.

"Well I think there's a stand up shower," I answered.

"So there is," Clare laughed, "care to join me."

She curled her fingers around my swelling shaft, "I'll clean you off," she whispered.

"I thought you were the one feeling dirty." I chuckled.

"I think we're BOTH absolutely filthy." Clare hissed.

"I've learned to never argue with the person who gets you hard."

"Especially when they've got your balls in their fist." Clare grinned while squeezing gently.

I honestly intended for us to actually shower and we got as far as standing under the warm water and applying the floral smelling shower gel to our bodies before horniness kicked in again.

It started with the walk to the bathroom. I watched Clare's ass sway back and forth as she walked. She made me sit on the counter while she started the shower and tested the temperature before gesturing me to follow her into the shower and under the pulsating spray with a wink and a, well honestly come hither wouldn't be adequate, more like come fuck me Little Man. I might be projecting on that last one.

She curled her hand around my semi hard shaft and pulled me under the cascading water.

She poured gel into her hands and rubbed it into my chest and stomach before cupping my balls and using her probing fingers to tease my asshole even as she looked into my eyes.

"She wants to fuck you so bad you know," she whispered, "she has anyone she wants whenever she wants but you're special for some reason."

I moaned softly, my erection already responding to her stroking hands.

"She put me in chastity and denied me an orgasm. She fucked me over and over again not letting me cum but she made me describe your workout."

"Everything?"

"Everything, she must have fucked a pint of cum up my ass just during the weight training alone."

"Wow!"

"She promised you'd fuck me hard and suck every drop of cum out of my asshole."

Feeling weak in my knees, I braced my hands on the wall of the shower. Clare's hips pumped my behind, I felt her stiffness that yearned for my bottom.

She stroked my cock, "What did you do to her," she hissed, "why is she horny for you?"

I recounted to Clare my first time with Mommy. The Tgirl panted and moaned as I vividly described licking Mommy's sweat-soaked body before taking her thick creamy load in my mouth.

Clare whined, I felt a climax rising in my shaft.

"I want you," I grunted while kissing her hard, our tongues swirling around each other's mouths, my hands sliding over her soapy slick body. The water fell over our heads and down our faces.

As we came closer together, I could feel Clare's raging erection pressed against mine, our shafts grinding and frotting against each other.

The hot water ran over our bodies and we huddled tightly together, my hands still playing with Clare's incredibly stiff cock and sweet ass.

"You like that baby, you like Mommy's FuckToy playing with you?" I hissed into her ear.

"MMMMM Yes" she moaned as she put her head back on my shoulder and tightly closed her eyes, enjoying the feeling of my fingers stroking her throbbing member.

I could feel the hot water running in between our legs and even between my ass cheeks.

"Do you think Mommy will fuck me in a shower like this one?" I asked, "you think she'll ream out my ass?"

"GOD I hope so, I hope she lets me watch." Clare sighed.

For several minutes we stood pressed against one another, my hands stroking and playing with her sweet knob.

"I want to suck it," I whispered, dropping quickly to my knees, letting the water wash all of the soap off of the shaft.

I watched the water bouncing off the surface.

"It's beautiful," I whispered before opening my mouth wide and engulfing the head.

I licked and slurped my tongue around, as the hot water kept cascading down, hitting me in the face. I kept my eyes open, watching the expressions of lust and passion swim across her face.

Her eyes snapped open, her hand came down cradling my head and with a moan that came from the deepest parts of her, pulled my head into her crotch "forcing" me to take her deep inside my mouth.

The head smacked against the back of my throat and I felt it tickle my tonsils. I slid it back out a few inches and then engulfed it again. I wrapped one hand around the lower shaft and stroked it gently into my mouth, using my other hand to cup her trembling ass.

I rubbed and massaged her cum filled sack between my fingers while I kept pumping my mouth down her stiff length.

Clare groaned with pleasure, her sighs even drowning out the hiss of the shower, her hands, resting against the back of my head, continued pulling at my head and I could feel her trying to force me deeper onto her hard rod.

I gave her the pleasure she craved. I fucked my mouth on her erection with a hard fast pace, swallowing the pre-cum that leaked out onto my tongue.

Some part of me contemplated the depraved scene.

Me, on my knees feasting on the prick of Mommy's sub. Her fingers curled around my head, hips pumping, yearning to fill my hungry sucking mouth with her lust and sex; loud groans of pleasure echoing off the steamy glass of the shower.

I wanted to swallow her load, to suck her cock off until she unloaded her spunk into my throat, but my own shaft practically vibrated. I could almost feel it acting like a divining rod, calling me towards Clare's ass.

My thumb found her hole, moist from the soap and water and clearly needing fucking to judge by her moans when the tip of my finger slipped inside her anal ring.

"Yes, fuck me," she pleaded.

I removed her wet shaft from my mouth and stood up.

I picked her up, cupping her ass in my hands. Her arms came up wrapping around my head moaning into my mouth as my shaft slid across the puckered lips of her ass.

Pinning her to the wall I bent my knees and literally sat her on the head of my stiff head and pushed forward.

We sighed in unison, my eyes rolled back in my head as the tightness of her asshole hugged my probing shaft.

She yelled as I slid the first few inches of my shaft right up inside her ass. Each hard thrust filled her hole, plunging deep inside of her to the hilt.

I bent my knees, all that working out I'd done earlier apparently already paying dividends. My thighs burned a little though as I supported Clare's weight. She must have heard my slightly pained grunting because one of her legs slid down, curling around me.

The hot water ran down my back as I buried my face in Clare's neck as I concentrated on pounding my shaft into her ass. Her asshole tightened and gripped around my erection as it pistoned in and out of Clare.

"Fuck, yes I love it," she yelled.

So did I, I could feel my climax rising up in my shaft

My shaft kept pounding her ass, her tight hole close around my thickness like a velvet gloved hand.

"Oh yes me....FUCK sweetie....fuck me hard ...You're gonna make me cum again."

Her ass convulsed and contracted around my stiffness as another hard orgasm swept through me. I actually yelled my lungs out as our mutual climax hit.

"All over that cock, baby," I panted, "CUM ALL OVER IT."

My commands seemed to fuse her up and get her even hotter as her creamy goodness gushed and poured across my stomach and chest. I could feel it running down my front and coating my flesh in a creamy glaze that reached my cock lubricating it's journey in and out of her orgasming asshole.

I yelled and panted as a final wave confused my insides and I felt my own creamy baby better shooting deep up Clare's ass.

My knees gave way, and I sank to the wet floor the messy goo of our lovemaking pooling around me. Clare sagged against the wall of the shower. I leaked in running my tongue down her shaking thighs catching some of my cum as it leaked out of her anus.

She cradled my head, more gently then when she'd been practically skull-fucking me.

"Give me a minute baby," she puffed.

She was definitely winded, but Clare was rather obviously in better shape then I.

I saw her amused smirk.

"No fair," I whined, "I just started with a personal trainer today."

"We'll have to focus on getting your stamina training going, especially if you're looking to go the distance with Mistress."

She reached over and turned the water off. I climbed to my feet , slightly embarrassed that I was unsteady as we walked back to the bed.

"Let's give you a rundown and then we'll order some room service."

"Maybe not necessarily in that order?" I pleaded.

Clare laughed and reached for the phone while I arranged myself on the bed in the vain hope I looked mildly erotic as opposed to bone weary.

**Clare's Story**

Clare watched Micheal sleep.

They'd made love, ....Hell they'd fucked a few more times. Clare was still feeling a little bit tingly. Proof if any were required that she was in much better shape then her bed-mate.

Still he'd been pretty good for someone new to her slightly fucked up world. She saw a text message from Mistress. She responded, Mistress wanted to know how her newest Fuck Toy had performed. Clare interfaced with the room's surveillance equipment and sent her the raw footage under the title Proof of Concept as instructed.

People always reacted differently when they knew they were being observed. Hell she had enjoyed their time even more knowing they were being recorded. Score one for her voyeurism fetish. Since the footage wasn't going to be used outside of a small tight knit circle, prior consent wasn't strictly speaking necessary.

Mistress thanked her for the footage and repeated her pledge that Clare would have dibs on that sweet ass when Mistress was done. She looked at Micheal, he didn't know it yet but his life was going to change profoundly in the next few hours. Just the thought of it got the Tgirl hot enough that she wanted more. Clare decided to wake him up with a blowjob. Sleep was a luxury FuckToys like Clare and now Micheal were rarely afforded. Micheal might as well start adjusting to his new normal.

**TBC**