Mailboy's Reward

(With a huge thank you to the great "Adventures of a Mailgirl" stories which were my inspiration for this story)

It's a typical Monday morning and I am standing around talking to my co-worker Gina near her desk. We work at a medium-sized IT company. I only started a week prior.

Gina is a brown-haired girl in her late 20s, but kind of chubby, with glasses and average looking, but she is smart and funny as hell. I am a 26-year-old man who is about 6'2" tall. I work out pretty regularly and swim so I am in good shape with a toned body.

"Morning Gina," I say. "So did you do anything exciting this weekend?"

"No, I just watched Netflix but let's spice up this morning. Let me show you why you will love your new job here..." I see her push a button on her computer to request a courier for a mail delivery.

We continue with the small talk when suddenly, SHE comes around the corner and my world freezes. Here in this boring office is a naked young girl wearing a leather slave collar and a pager on her arm. She is in her twenties, and I can see her pussy is shaved completely bare and they have tattooed the number 3 above her firm butt where a girl would usually have a tramp stamp. She has a pretty, inviting face and her hair is blonde bob cut that really accentuates her face.

Her body is athletic like a professional gymnast but not quite as muscled. I stare at her bare ass which looks like you could bounce a quarter off it and Gina elbows me.

"This is Anne. At least that was her name. Now she is just number 3. Inspection position, number 3, now," Gina says as she whispers to me "Watch this, Mark."

"Yes Mam," 3 responds, and she puts her hands behind her head, spreads her legs and goes up on her tiptoes without hesitation.

"Mark, you better check her uniform, and make sure she is properly shaved. Mailgirls are not allowed any hair below their pretty little necks," Gina says.

I walk closer to 3, as she trembles on her toes, I can see the strain in her calf muscles and her tight, perfect ass and a light coating of sweat on her entire body. She smells wonderful, fruity but with a slightly cinnamon note as well.

Gina says, "We're not supposed to touch her, but run your finger along her little naked slit to make sure there is no stubble. She won't mind, will you 3?"

3 groans, "No Mam."

I approach this naked beauty and run my finger lightly on her bare pussy slit and can feel her quiver and tremble. Surprisingly her pussy is a bit wet.

Gina says, "Do you feel any stubble on her little hooch?"

"No, very smooth but her pussy is a little wet," I reply.

Gina responds, "Mailgirl 3, why is your pussy wet?" As I continue to stroke 3's bare kitty.

Anne sputters, "B...bb..because he is stroking my bare hooch...and it turns this naked mailgirl on."

"Mark, she hasn't worn a stitch of clothing for the last 50 days. Nothing but her collar. And she was the prudish type who wouldn't even wear a thong bikini at the beach before she signed up to be a mailgirl. But you'd better check her anus for stubble too. She won't mind," Gina says.

I see Mailgirl 3 give her a nasty look, but she stays on her toes and makes no effort to stop me as I run my hands down her tight bare ass and then stroke my index finger into her crack right over her little anus.

There is no hair to be found, not even stubble but with the moisture from her pussy and her sweat my finger accidentally slides in her tight asshole up to the second knuckle. "Sorry 3," I say.

"Nnnnnngggghh, ffff.. uu.. c..kk," she stutters biting her lip. She never falters from her inspection position but starts to grind her asshole on my finger.

Gina commands, "Ride his finger 3. And Mark blow in her ear while she rides your finger, she likes that."

Anne says, "Yes Mistress." She continues to grind her tight asshole on my finger, taking it the entire length into her most intimate opening by flexing herself up and down on her toes. Her muscle tone is amazing as she goes up and down and clenches her asshole on my finger. After 2 minutes of her taking this finger fucking in the middle of the office. I blow in her ear lightly and suddenly; I feel her clench her asshole tighter and she shudders and moans as her eyes roll upward. I can tell she has just orgasmed as some juice runs from her pussy down her bare leg.

My cock is tenting through my pants from this sexy mailgirl riding my finger, a fact

Gina notices and says "3 you are cumming like a little slut. That's enough inspection for today, you may go now."

3 moans softly and licks her lips as I remove my finger from her ass.

She comes down off her toes, gives me a smile and whispers in my ear "Nice to meet you Mark, thanks I needed that so bad..." She runs off as I admire her perfect naked ass.

"Earth to Mark," Gina says snapping me out of my daze. "We have a few girls in our mailgirl program now. Bet you didn't think you would get that kind of benefit at this company. We have Anne and five other young, naked mailgirls. But, what if I told you there is a way that you could get some private time with little Anne (sorry Mailgirl 3)." As she lightly brushes her hand over my still erect cock.

I ask, "What would I need to do?"

"Well, and this maybe too much for you, but maybe not," Gina says

I say, "Go on."

She continues "They have asked me to start a new 60-day Mailboy program. It is not fair that the guys get to ogle all this mailgirl pussy and ass on a daily basis, and the women workers get nothing to look at. I'd have to check if you meet the requirements to participate. BUT, if you met the requirements, I could guarantee you that you would get to fuck little mailgirl Anne, every one of those 60 days. Provided you do a good job for me as a mailboy." With this she gives my cock a slight squeeze through my pants for emphasis.

I respond, "I am not sure, what does a mailboy do?"

"Well dummy, maybe you deliver the freaking office mail," Gina jokes.

I say, "Ok tell me more."

"Well for starters you would be buck-naked at all times other than a leather cock strap and your pager. No hair is allowed below the neck either, you must be shaved bare just like the little mail-sluts. You will sleep in the mailboy locker area. You will be hustling your naked ass from office to office with that nice cock out on display." Gina says as she brazenly continues to stroke my cock through my pants right here in her cubicle.

"I will be your trainer, and to make it worth your while, not only would you get to fuck little Anne every day, but I can offer you a $25,000 bonus. If I decide you have what it takes." She continues while squeezing my cock a bit more firmly. "Do you want to do your cock dance with Anne and walk away with a nice chunk of cash? But before you agree you had better understand that I own your naked ass for those 60 days if you do!"

Gina continues, "So, Mark are you interested?"

"I don't know...I am really not sure I want to run around like a naked slave for 60 days. And that cockstrap you are saying I have to wear will have me hard most of the time..."

Gina says in a harder tone, "Oh yes, you will be semi-hard and probably dripping your pre-cum most of the time too. If you don't agree in the next 5 minutes the deals off the table and your hard cock won't be inside Anne's pussy, mouth or ass for the next 2 years of her contract! So, do you want to interview to be my first mailboy and fuck the girl of your dreams or are you too much of a pussy?"

I respond, "I may regret this, but OK."

"Ok, the interview starts now. Get your clothes off!"

I respond, "Here?"

Gina says, "Right here, right now."

Feeling I have made a mistake as I look around and see three other people in our area working, but I am too turned on from feeling up naked mailgirl Anne, that I comply and start stripping immediately. I take my shoes and socks off, my shirt, and then my pants, realizing that wearing a thong today because it's laundry day may have not been a good idea. Gina boldly snaps the thong strap up my bare ass and says, "So you are a thong guy? Nice, now get those little undies off too and hand them here."

I realize there is no turning back now, as I pull my small thong off and hand it to Gina who places it in her purse.

"All this has to go." Gina responds as she strokes her finger through my neatly trimmed pubic hair. "You have nice muscle tone Mark, not too big not too small. Kind of like Matt who used to work who until he was fired for fucking Anne."

She then orders, "Attention position now!"

It will be so worth it I tell myself as I assume the same humiliating position Anne was just in.

She says, "Legs further apart. Now to put on the first and most important piece of your uniform." She takes a small leather strap out of her desk drawer, about 3/4" wide by 3" long with a buckle on it. She loops the strap around my erect cock and balls, then buckles it and adjusts it so it is moderately tight.

With her hand still firmly around my cock Gina says, "Your cock strap goes on when you get up each morning and doesn't come off until you go to bed. Only I or my designee may remove this or adjust it. Understood?"

I respond, "Yes."

She continues, "This little strap is to remind you to stay hard all day as you make your deliveries. You wouldn't want Anne to see you naked and soft, would you?"

I answer, "No."

Squeezing my balls firmly she says, "No what??"

"No mistress."

"That's better, but if you break my rules I will replace your cock strap with a chastity cage, and you do not want that," as she hooks my pager around my bicep. I look over and two older ladies are watching my interview and I see them lick their lips.

Gina says, "This pager shows your deliveries and the time allowed for each one. If you are late on a delivery, you will receive a demerit. If you get 2 demerits in a day, you are due for punishment."

Gina shows me a small whip and then whacks my bare ass with it. There is a surprising painful sting.

"Ok now for the 2nd part of your interview, follow me to the locker room."

We go to a locker area on the same floor, while I am extremely conscious of being completely naked on the way there. Several female employees and a few guys ogle my naked body as I walk around with my cock bouncing in it's strap.

The large room has an open shower area, 3 small beds, a bathroom and a mirror on one wall.

"This is your new home for the next 60 days," Gina says. "That glass is one-way so the ladies will be watching you shower and shave each morning, just like the guys watch the little mail girls. Now for the final part of the interview lay down on your bed."

She pulls out a shaver and thoroughly removes my pubic hair. She then grabs my cock and starts to stroke it.

In a sultry voice Gina says, "I have been watching you since you started working here, but to be sure you are worthy of fucking Anne, I have to test you out myself, Slave. And besides, why should little Anne have all the fun. Ok?"

"Yes mistress"

"I own your naked ass now, mailboy," Gina says as takes my 7" hard cock in her mouth.

She is very skilled with her tongue, and she has me right on the edge of cumming.

"Not so fast slave, you are going to earn the right to wear my cock strap now," she says as she removes my hard cock from her mouth. Gina unzips her skirt, removes it, and then takes her blouse off. She is wearing only a tiny black g-string which she pulls to the side. Her pussy is fully shaved, and she a nice round ass and C-cup firm tits, with just some chubby baby fat on top of her curves. I wonder what Gina would look like as a naked mailgirl running around with her chubby little naked ass around the office.

She mounts her wet pussy on me and starts to grind. I grab her ass as she grinds up and down on my cock. I pull her little g-string tighter up her ass while she rides me.

"I got so wet watching you finger-fuck little Anne's ass, now it's my turn. Work mailboy, work that hard cock in your Mistress! Fuck me just like you will be fucking Anne tomorrow if I allow it. I've seen her fuck and you won't last long, now give me your first load as a mailboy."

"Nnnghhhhh," I groan as her tight pussy milks my cock I release my large load for almost a minute.

Gina groans as she cums too, "Good, that's it, let it all out boy. Give me that man cream."

She gets up when she is finished and adjusts her small g-string back over her pussy and puts her short skirt back on.

"Congrats! You passed the interview, number 1" so tomorrow you just might be fucking Anne, if you continue to satisfy your new job requirements."

Gina has me sign my 60-day contract and my mailboy number is painfully tattooed above my ass while she watches. She has me do a couple of trial deliveries to some of her female friends, and even one guy. Gina has instructed me that anybody who wants to can order me into an inspection and grope me or even finger my ass, but I am only permitted to fuck her or sweet Anne. She makes a big show of tightening and loosening my cock strap during these deliveries. "Got to make sure this is just right, not too tight and not too loose, Slave" she purrs. I just take her manhandling me in public and her adjustments while groping my balls has me hard and dripping pre-cum most of the day as well. One middle-aged woman asks if she can adjust my cock strap and Gina says, "Yes, Inspection position 1, now!"

I assume the humiliating position and the lady tightens my cock strap a notch and gives my balls a squeeze.

"Thanks, mam," I respond.

At the end of the day, Gina takes me to my bed, which of course has no covers.

She says, "Good job today, mailboy," and starts to suck my naked cock with extreme skill.

"Arghhhh...." I groan as I shoot my load in Mistress Gina's throat.

I ask, "May I have my cock strap off, mistress?"

She says, "Yes, slave" and she finally removes the leather strap and leaves the room.

The next morning.

Annes viewpoint

Delivery for Gina floor 5, Mailgirl 3 sees on her pager. Not good, Anne thinks, what new humiliation does this bitch have for me today. Yesterday she had me felt up by the cute new guy and I came from his finger up my ass while that smug bitch laughed.

After finishing shaving her snatch bare, Anne quickly runs up the stairs.

There is Gina sitting at her desk. "You are 2 minutes late; I should have your little naked ass whipped by your Oka-San again," she tells Anne.

Anne grimaces and thinks of the last time she had her bare ass whipped by Oka-San because of Gina. It is still fresh in her mind because it was only 3 days ago. Her ass still stings from the 10 strokes she had to endure while strapped to the punishment horse. To add to her humiliation, she was so horny that when she was released, her Oka-San allowed her to finger her twat until she orgasmed right there on the punishment horse like a complete slut.

"Sorry mistress," Anne replies, knowing how much Gina owns her now.

"I have a little surprise instead," Gina says. "You know where this goes, so get it in now," Gina commands as she lubes a metal butt plug up and hands it to Anne.

Anne hasn't ever worn a butt plug before, but she knows the punishment Gina can inflict on her naked body...besides being this submissive makes her SO horny. She slides the cold butt plug up her ass, groaning as it stretches her asshole and slides fully home.

Gina says, "Good. Let me see it, little slut. Ankles, now".

Anne complies bending over and grabbing her ankles and showing her little green jewel to Gina (and the other 3 employees on the floor.)

"Nice number 3. Your surprise is in the stairwell you used to fuck Matt in. And do not disappoint me. And that butt plug doesn't come out of your ass today until you go to sleep tonight or need to go the bathroom. Got it, slave?" Gina asks, "Now go", and slaps her tight ass.

Anne responds, "Yes mistress" and rushes to the stairwell.

Mark's viewpoint

I am in the stairwell on my floor, after delivering mail all morning in nothing but my cock strap.

Gina called me to her cubicle around noon, groped my balls and said "I'll be watching on camera and taping the show so don't disappoint me. Now get in those stairs and work that cock in your true love."

I see mailgirl Anne run in the stairwell suddenly, and she has a hungry, wanton look in her eye. Her naked body has a light coating of sweat on it.

"Oh no, she tricked you into being a naked mailboy," she says as she sees my naked body and licks her pouty lips. "And you have to wear this too," Anne asks pointing to my leather cock strap. "Is it around your cock all day?"

"Yes, I have to wear it all day and Gina only removes it when I go to sleep. I agreed to all of this for a chance with you," I tell her.

She says, "While I guess I better make it worth it then, mailboy," kissing me hard for a minute while groping my cock and then she pushes me down onto the ground and puts me in the 69 position.

I gasp when I see she has a small green jewel up her ass, "Did you wear this plug for me."

"Yes," she groans. As I lick her little pussy and she takes my cock in her mouth. "Do you want this cock strap off, stud?" Anne jokes.

"No, I am not allowed to remove it. Only Gina can or her designee."

"Same with my butt plug. Guess it stays on then. Good, because I want your slave cock extra hard for my slave pussy!" Anne says as she tightens my cock strap a notch.

I lick her sweet clit and also push her butt plug into her ass a bit deeper.

"Don't you dare cum, slave," Anne says as she orgasms. "I am not nearly through with you." She then mounts me and starts to ride. I tweak her perfect hard little nipples. She rides me like a stallion and says, "Now bend me over stud and take me from behind. Being a mailgirl keeps me so horny and this plug she made me put up my ass has me even wetter. Get that hard mailboy cock back in my twat, now!"

I pick up Anne and bend her over the railing and plunge my cock deep into her pussy pulling her plug in and out of her ass while working her.

"Oh my god!" Anne says

I work her gripping snatch, like my life depends on it. Grunting and thrusting and pounding her sweet little pussy. There is absolutely nothing that can compare to being a naked slave fucking the naked mailgirl you are in love with. I smack her ass hard and pull her head up by her collar.

Anne moans, "Ohhhhh, please don't.... stop. Slave. Please fuck me harder, my slave pussy is so horny from being a mailgirl...running around all day naked with my hooch on display...Gina is watching us on the cameras...but I don't care. Fuck me...just fuck me... harder..."

Finally, I can hold my load no longer and I blow it deep in Anne's pussy. I grip her tighter as I unleash.

She orgasms simultaneously while taking my load.

We lay there for several minutes in ecstasy experiencing the afterglow. She gives me the most passionate kiss of my life and says, "Thanks, I really appreciate you doing this for me. I never thought any man would be willing to become a naked love slave for me. I love you, Mark."

"I love you too my sweet Anne," I respond.

I see her pager go off, and she kisses me once more, smacks my bare ass and says, "Until tomorrow, lover."

I see her butt plug gleam in the light as she runs up the stairs to her next delivery, giving me a perfect view of her pussy as well.

I realize my mailgirl is going to have that butt plug in her ass all day today.

My pager buzzes, and I see it is Gina.

It reads, "Good job. That was so hot, you owe me for having your mailgirl's little ass plugged for you. Be at the locker room in 10 minutes and you better get hard again, because now that Anne has had your cock, I need it too."