Mail Girl - Anal Family Toy

You happily get up from your couch as you hear the elevator doors open that lead directly to your apartment. Except you only one person has the key card, so you're naked to welcome your sugar-daddy except for the only piece of “clothing” you cannot - and don't want to - take off yourself. He promised you a surprise today, so…

You freeze.

Out of the elevator steps your owner - with another man. About five centimetres taller. Young, scrawny. T-shirt with a video game logo – one that you play - on his chest. Pimply – not far out of his puberty. Of course you recognize him - your boss showed you a lot of pictures. Despite never saying it – probably not to him, either - he’s proud of his only son.

Who just stares at your tits, his mouth hanging open.

“Here we are, son.”

His father breaks the ice. Or tries to.

“This is Lexi, my – companion for lonely times, if you will.”

You scoff. If he chooses to introduce his son to you, let’s make things clear. You have no problems to introduce yourself as what you are.

“I’m your father’s sex pet. Pleased to meet you, young man”

You shake his hand, trying to make eye contact, but his eyes don't move up from your chest.

“You're cheating on Mom with… this…”

"I wouldn't consider it cheating, son, it's more of a business arrangement. Men have needs. I don’t have to tell you that any more, you're old enough, am I right?"

He turns to you.

“It’s his 18th birthday, today."

You sigh relieved. You’re proud of your lack of inhibitions and false shame since you are a woman - so much less silly worrying than you used to – and yet, you are always a bit nervous that your boss demands things from you that REALLY push your limits. Or those of legality. You'd do it. You would do everything for the luxury he provides. But not today. His son is an adult and obviously consenting to you. You're perfectly fine with getting to know this 18 year old boy.

“Happy birthday.”

You kiss him on the lips – closed mouth, no tongue, he’s nervous enough – but you do let your tits touch his chest. He flushes deep red.

“Yeah, well, whatever, Dad. Great you trust me with your big secret, what am I doing here?”

“I haven’t given you your birthday present yet. When I turned 18 my father gave me a car but in this day and age... You already got your licence and a Mustang at 16, so I thought making you a man would have to be a bit more… intimate.”

He grins. You raise an eyebrow as you understand. It’s not his habit to inform you about his plans any sooner than you really need to know. You wish he had made an exception this time, but you surprisingly don't mind being made his son’s birthday present – making him a man.

You smile and feel warmth spread in your lower body, but a forewarning would have been nice to be prepared. You don't have any experiences dealing with teenagers as a woman. Your taste – even before you became this rich man’s pet – was for older, mature, experienced men.

That hasn't changed much – but the 18 year old looks quite like his father - a taller, pimply, full haired version. But he’s cute. Awkward. Unlike is father he reminds you of yourself when you were a boy his age. Which is – more than weird, but also – surprisingly exciting.

What Alexander wouldn't have given for the chance to become a man at the hands of an older, experienced woman when you turned 18. And maybe he would have turned out better. Some guidance to stop him from become the egotistic, selfish, toxic jerk that you were before this chance turned you into a confident, sexual, strong woman.

You see the boy's eyes widen as he understands, too.

”DAD! I have a girlfriend.”

The old man chuckles.

“Who hasn't let you fuck her, yet, am I right?”

His son blushes fire-hydrant red. That was mean. You have to suppress a giggle.

“We… we've done stuff. Lots of stuff!”

“I’m sure. But you Are still a virgin. But as I said, this is pure business, anyway, this type of women doesn't count as cheating!”

You chuckle. It sounds like an insult, but it kinda makes you feel nice. You take it as a compliment. You enjoy being This type of woman.

“And you're not getting to fuck her pussy, anyway. That first time for your dick will be reserved for your little girlfriend."

His son leans forwards. Looks down your body and his eyes stick to the only thing you’re wearing. He probably thought it was a pair of panties, and didn't dare to look at closer.

“What the…

He does now.

“Is that metal? Is that... what’s it called…”

“A chastity belt.”

You help him out.

“Quite the misnomer in my case. I consider myself anything but chaste."

His father laughs.

“You make your lover wear - that thing???”

His looks at his father in horror as the old man smiles at you.

“I'm not making her wear anything. That was her gift to me for my birthday.”

The boy looks at you aghast.

“But... why... that’s..."

“Your father is man of particular tastes…”

You look a the old man and he nods.

“He’s an ass man. Hasn't fucked my pussy once since I'm his. So… as my whole body belongs to him and he decided not to use that part, I can make it official and never use it again. Haven't taken it off, haven’t regretted it for a second. Haven't touched my clit or had anything my my cunt ever since."

"But... doesn't that… don’t you have any… don’t you miss…”

He stammers.

“I don't miss a thing. And I DO have – orgasms, if that’s your question. In fact, the orgasms I get with your Dad in my ass are miles ahead of everything I ever experienced before. Rarer, but SO much better.”

And that Very much includes the ones when you had a cock, but you'll never reveal THAT to your owner or anyone.

”Orgasms from…”

The boy runs out of words. His farther fills the silence.

“It takes a special kind of woman to become so – tuned into my particular preferences and enjoy it so much herself, but I was lucky to find one. In short, Lexi is a true butt slut. An anal whore."

The boy stands there, open mouthed, shaking his head.

“And... don’t you… I mean … when you're alone….”

You giggle.

“I masturbate. Of course. But only anally, with some nice vibrators and dildos. None of the messy pussy rubbing or clit touching. Anal orgasms for me only. Your dad has the key to my pussy - literally. And I don't get to use it. Ever. Nor do I want to.”

You distract the men.

”Alright, I assume, it's all quite a a lot to work though. How about a good breakfast?”

“Splendid!”

Your owner nods and you walk into the kitchen, prepare some small snacks - a fruit bowl for you – you like to eat more heartily, but your owner loves to see you take care of yourself and you oblige – and sandwiches for the men.

While his father eats hungrily, the boy just nibbles on his, his eyes wander again and again toward your naked chest. You can see his pants bulge. Girlfriend or not, he's an 18 year old boy.

You take the initiative and feed him one of your fruits – he blushes but takes off from fingers. Another one and he eagerly begins to lick them as you enter them further into his mouth.

Eventually, when you feel he’s ready to accept his birthday gift, you lean over to kiss him on the mouth. Open your lips. You smile, your tongue teasing his until he also opens up and lets you in, He's shy, at first, but your probing tongue encourages him and he begins to join. He has some experience with his, he wasn't lying. Not his first kiss. But maybe his first...

You go down on him. Pushing up his shirt, kissing his belly while you open his fly and release his hard throbbing cock. Quite an impressive one, got that from his Dad. You lick your lips.

“Nice cock.”

You hear a **** noise – not a compliment he’s used to. Pull back the foreskin and kiss the glans lick it, and begin to suck on it. He moans, closes his eyes, thoughts of his girlfriend apparently forgotten.

His father gets up.

“I need to go to work soon, I'll leave you two lovebirds alone – but you mind if I join I for a quick release, son?”

You feel the boy move - apparently shaking his head, as his father positions himself behind you and with a quick, practised motion sinks his cock into your bowels.

Your ass welcomes him, more than used to it by now, but it never gets old. The feeling of fullness is overwhelming, the burning turning into a warm wave of pleasure running all through your body as he begins to pump your tight sphincter. You close your eyes, enjoying it while sucking his son's eager erect cock.

It goes quick, your owner can take his time if he wants to – his stamina is amazing for a man his age, but this morning he doesn’t. You felt his son's cock twitch in your mouth more than once in these few minutes. His first blow job you assume, and the teenager doesn't have as much experience to draw it out like his old man but you do. You slow down whenever he’s getting close, edging him, making him groan and grunt, and you at least manage to make him hold out enough to come together with his Dad a few minutes in. As you feel his hot cum shoot into your bowels, you suck hard on his son's cock and take his load into your hungry throat, swallowing it all, filling you from both ends. He tastes almost like his father – tangy and musky - a bit more acidic. Maybe to many energy drinks.

You lick your lips as the old and the young man slip out of your holes. You owner slaps your ass.

“Alright, I'll leave you two alone. You have her as long as you want her today, for whatever you want. Except for the obvious, of course."

Grinningly he flicks a finger against the small metal belt caging you pussy.

“It’s a school day…”

“I called your principal. Very understanding man when I explained to him we're having a father son day for your 18th.”

The boy looks at you.

“Dad's the main donour for my school.”

You smile

The old man kisses you goodbye passionately, then puts an envelope on the kitchen counter.

“Here’s another present for you. Don’t open it before you’re done with me pet for today. Have a splendid day, son!”

He enters the elevator and the doors close.

The boy takes out his phone and you raise an eyebrow.

“You’re kidding me, right?”

“Just texting my girlfriend. We are going to go that fancy fast food joint after school to celebrate, and then to her place. Hopefully... If I don’t show up for school she’ll be worried if I make it.”

“Aww. How considerate. I bet you're a great boyfriend.”

He looks at you blushing.

“I just got a blowjob form another woman. Am I?”

You kiss his cheek.

“Your dad was right, I'm not anything romantic or personal. I'm just a harmless fun birthday gift. But don't write her why you aren't at school....”

You wink at him.

“Haha. Thanks a lot for that tip.”

He puts his phone back.

Stands in the middle of the room awkwardly.

“So... uhm...I…”

You smile at him seductively.

“Are you feeling like a second round already?”

”I’m.. I… Not sure…”

You nod, the blowjob was a surprise attack to lower his defence. You're sure it worked and you'll get him to relax, but for now, maybe ease him in some more. Make him feel comfortable.

“OK, no need to rush. Later. What else do you do to have fun?”

“Well, I… skate..”

“Cool.”

He blushes and grins.

“Gaming, of course.”

“Of course. I'm a gamer, too.”

“You are?”

“Sure – I hope you’re not one of the guys having problems with girls gaming?”

“No. Course not. My girlfriend's a gamer too.”

"Cool. Come into my lair then!"

You take him to the lounge area, where below the TV multiple consoles are installed.

“Wow. Nice. I only got two of those..."

You smile.

“Yeah, your Dad only got me two, too, when he had the apartment furnished for his pet. Had to get the rest myself."

He blushes again - hard, as you remind him this whole pace is paid by his father for you as reward for servicing him.

“But he Did have a landline phone installed.”

You both laugh

“He’s SUCH cringy boomer!”

He smiles at you – there's a notable age gap between you, you're far from being the same generation, but mocking his Dad, whose age gap to you is twice as big as yours to his son, is bonding. Even though you feel sympathy, gratitude, almost love for the old man and you would never purposely disrespect him.

You pull the boy towards the couch and start one of the consoles. You're still naked - don't even think about it, it comes natural to you and after you tasted this boy's cum, he’s practically family. Metaphorically spoken.

You play for a while. You used to be a decent gamer as a man - not as good as you believed to be, but still - and have a lot of opportunity to practice when your owner doesn't need you and you're alone in your huge apartment. You notice you can crush the boy – you picked the game you're best at, anyway. And he's more than a little distracted sneaking peeks of your body. But you don't. It’s his birthday, so you let him win. But not too high. Just enough so he keeps respecting your skills.

“You do play with your girlfriend, too, huh?”

You open a conversation after a while.

”Yeah. She's cool.”

“I bet. When you said you did stuff, how far did you go?"

He looks at you.

“I’m not sure I should talk about her with…”

“Oh come on, we're gamer buddies, right? With benefits.”

He chuckles.

“We kissed. Made out…”

“You touched her boobs?”

“Sure.”

He grins.

“How are they?”

And blushes.

“G... great. Really nice. Uh… smaller than yours but...”

You giggle.

“Size isn't all. But you may touch mine, too!”

He does, blushing.

“And what else?”

“I…

He blushes then grins – you see a mix of embarrassment and pride. Now that could be interesting.

“Se lets me eat her pussy.”

You perk up.

“Really? You like it?”

“It’s awesome. Totally great. Love the taste. And the way she moans when she cums...”

“So you make her cum, huh? Good boy.”

He blushes hard and grins sheepishly.

“But... hm... no offence but that was your first blowjob this morning, am I right?”

He nods.

“Thought so. So – does she make you cum?”

“She… she jerks me off afterwards. But that’s it.”

“Hmm. Cool. I like a girl who knows what she wants. Getting her boyfriend to eat her out without expecting to get his cock sucked in return. Sounds like a confident, strong girl. I like her. And I like you for giving her what she needs and not make any demands. You're a good one.”

You lean over and kiss his mouth. You mean it. You wish you had been a teenage boy like him. His friends may call him a beta or a simp or whatever boys today use for is insulting considerate, kind, gentle, caring males.

You were a selfish prick, insecure, and trying to cover that with a tough act when you were a boy. Learning the lessons this boy so willingly incorporated into his life would have prepared you a lot. But then again you might not have gotten the chance to become a woman to atone. It all has its upsides

“You want me to give you a little tip how to drive your girl crazy enough so she might be willing to let you go the next step?”

He looks at you wide eyed. Tips from an experienced woman. Another thing you SO wished you'd have had as boy his age.

“Of course… My perspective is a bit subjective. You dad was right, my tastes are as particular as his. But... I'm not the only girl with these tastes. Not as strong as mine, but definitely many women have them.”

He looks at you confused.

“What I'm trying to tell you is that the hole you work at is not the only one she has…”

His eyes widen.

“That's... I… no offence, but you're... what you do is…”

You chuckle

”I’m a perverted ass slut, no doubt.”

He blushes hard.

“But I mean it: my tastes are not THAT unusual. You may be surprised if you include her rear entrance into your services to her."

“I... I couldn't…”

“Oh, bullshit, you're a young, horny man, don't tell me you wouldn’t...…”

You grin. Drop he controller on the couch and get on the all fours on the floor, your ass facing him.

"Don't tell me if ask you to lick it you’ll say no!”

You hear him gulp and smile. Look behind you at him staring at your ass.

“Come on, big boy. Lick my asshole!”

He breathes heavily and you see his pants bulge again. You grab your ass and spread your cheeks. He licks his lips and leans forward. Kisses your cheeks and licks them. You sigh

“The secret loot box is in the valley between the hills, my gamer hero!”

You direct him toward your hole and he follows your orders. You feel the wet slimy tip of his tongue against your well used pucker.

“That’s what I'm talking about.”

You lean on your arms, pushing your ass into his face even more and once he got over his first inhibitions, got a taste of it – literally – he's on fire. His tongue probes your sphincter, sloppily licks it, his lips kiss your hole and he practically French kisses your asshole, pressing his lips to it, entering your rectum with his tongue as deep as it can reach. You moan into your lush carpet – you love getting rimmed almost as much as getting sodomized. His father does it, too, of course, but not as much as you'd like. It's what you have instead of cunnilingus, after all. It's different, but nice. Better, in your opinion.

The boy eats his little heart out at your rear buffet until you hear him move. You lick your lips, don't look around. You're more than ready for the next step - without words, he puts his cock against your sphincter and rams it in, one hard, fast stroke. You let out a moan – his cock feels a lot like his dad’s, too, as do his motions and thrusts. Not bad for s first timer. REALLY not bad.

He’s got the talent to sodomize a woman from his Dad. You close your eyes and smile. As much as you admire his girlfriend for stetting her own pace and telling what's what in their relationship, she has quite a revelation coming towards her. This boy is good. Really good. You moan and grunt, sigh and pant. You bet he will be just as goods in her young juicy pussy once she let’s him in. If you were still into such stuff, he would do great. And if she ever allows him to enter her rear entrance...

He pushes you down to the floor and you grunt again. He’s GREAT assfucker. Lacks the refinement his father has, but makes up for it with pure juvenile energy and power. The familiar waves of pleasure that his father always can cause in you, too roll trough your body.

Unsurprisingly, he doesn't have his Dad’s stamina. His youthful energy and lust make him cum shortly before the heatwaves in you can reach their peak and grant you one of the anal orgasms you crave so much these days. He grunts, grabs yours hips and comes deep in your bowels. He sighs as he pulls out. Despite not having come, it was REALLY great experience. Close enough to his father to be familiar and yet different enough to be - exciting and new

Your body is burning, you sweat and pant, have to catch a deep breath as you look at him.

“That was amazing. Thank you.”

He smiles and blushes.

"Don't expect your girlfriend to let you go THIS far the first time you try rimming her ass, but ... I dare to say your talents in this area will make her... grateful.”

You wink at him and kiss his mouth.

“Happy birthday, young man.”

“Thank you, Lexi. That was…”

He stammers. You smile.

“It was, indeed.”

He pulls his pants back up.

“You should wash your face, I'm sure your girlfriend would notice a – different taste if she kisses you like this.”

You chuckle as he blushes and follows your advice, before kissing you again and turning to leave.

“Don't forget your Dad left you another present on the counter!”

He turns around and grabs the envelope. Opens it. Holds up the familiar black plastic card that’s inside it.

“Huh? Is that a credit card? I already got an unlimited one for my 15th birthday...”

You giggle.

“That’s a key card to my elevator. Congratulations, your Dad just gave you unlimited access to his pet. Well. Except for the one limit...”

His eyes widen.

“So I can come here…”

You embrace him

“You can come here and cum here…”

He blushes even harder.

“...whenever you want. Just drop by when you feel hungry for some ass. Or just wanna play a game!”

You kiss him, passionately, lovingly, for the first time with the same energy you reserved for his father so far. He's your new co owner now, he gets whatever the old man gets.

“I can’t wait.”

You feel his cock grow hard again, but he’s already late for his date - you don't want to be responsible for relationship drama, so you push him into the elevator - and immediately move to your toy-box. The two ass fucks were both to short to push you over the edge but more than enough to get you close to it. You feel you're going to burst if you don’t finish yourself off quickly.

On your huge bed you spend the next hour with your toy in your ass, grunting, sweating like a wild animal. You're not missing vaginal or clitoral orgasms. You didn't have have many, really before your owner turned you into an anal only slut, but those didn't compare. You sure as hell don't miss your ridiculously quick and pointless orgasms as a man. This is what orgasms are meant to be. Deep, tectonic movements sending hot magma all through your body, over and over again. It's impossible to count them, they melt into one another like tidal waves, and when the last one crashes over you, you collapse onto your bed, dildo still in your ass and fall into a semi-comatose sleep.

When you wake up in the middle of the night, your phone blinks. You let the rubber cock slide out and put it on the night-stand - you'll take it to the shower to clean it. Then use it. Then clean it again.

You read the message you got.

Dad gave me your number. Your advice was GOLD! My GF let me lick her pussy for my Bday, then I rimmed her ass and she went totally crazy. Literally begged me to fuck her pussy! Totally slammed her. Thnx, Lexi. Gonna drop by tomorrow and thank you in person.

You smile. Not just did you make your new co-owner a very happy young man, you also enriched the life of a young girl. How could this life be any better? This is what you are meant to be!

The End

Or is it?

[I will not accept chapters before the endings to not change the points, but if you feel inspired to write a story about the hero/ine's life after my final chapters feel free to write them.