Five Or Fifteen More?

by Emerald Omen

Rating: mature
Tags: Porn, Sex, Spoiled Rich, Profanity, Anthro, My Little Pony: Friendship is Magic, Fetish, Romance, Self Insert
Length: 2299

Minding your own business. That's what you were doing! Until you saw a MILF that you couldn't take your eyes off of. Of course, she noticed your staring. But she didn't get mad or offended. Instead, she made you an offer: Five, or Fifteen more?

You were just taking a walk through Ponyville, minding your own damn business, when she caught your attention. A pink MILF. She was sitting on a bench in a dress that was far to tight for her figure, and you couldn't help but stare. It was only for a moment, but she took notice of your apparent gaze. But she didn't get sore with you, or even annoyed. Instead, she smiled, and offered you a deal. Most would call it prostitution, but you called it the best day you've had in a long time.

Contains: Sex, Cum Inflation, Prostitution, and Sexy, Sexy MILF Action!

6/24/18 - 6/28/18: Holy hell, this story got featured! I can't believe it! Thank you all!

Audio Reading by Scarlett Blade: https://www.youtube.com/watch?v=wy9sovd6gPk&feature=youtu.be

Published 2018-06-23 16:50:07 UTC
Last updated 2018-06-23 16:50:07 UTC

Five Bits, or Twenty?

It was a great day in Ponyville. Sunny skies, nice temperature, and not to busy in town. You deemed it a good day to take a walk, so you did just that. You locked your house, and began meandering around the town. You'd been here for a few years now, a freak accident on Earth resulting in your arrival. At first, the half pony, half humanoid creatures frightened you, but after a while, you warmed up to them.

You walked around for a good hour, greeting ponies as you passed them, and you even stopped for a moment to talk with Miss Cheerilee, one of your best friends. Being a teacher, she was curious to learn things about you that she could tell her students, and you happily obliged.

After your walk and talk, you decided to go back home and eat lunch, but you didn't make it that far. No, your attention was drawn to a mare sitting on a nearby bench. She was pink with purple hair, she was hot, and she was clearly a MILF. CLEARLY.

She obviously was an older mare, probably in her late thirties or early forties, but she was very sexy! She had a generously sized chest, at least a G-cup, struggling to stay in her obviously to tight dress, and her legs were smooth and long. She showed a slight pudge in her stomach region, and had nice, wide hips. Your ideal woman... er, mare.

She clearly noticed you staring after a few seconds, because she made direct eye contact with you.

“Something I can help you with, kid?” she asked in a somewhat snobbish tone. You decided to ignore it.

“Oh, uh... sorry. I was just spacing out.” you quickly said. She smirked.

“I'm so sure. So I'll ask again, is there something I can help you with? Because, for the right price, I'm sure there's surely something I can do for you.” she said in a deeper tone. You struggled to fight your incoming nosebleed.

“Uh... l-like what?” you asked quietly. She suddenly stood, so fast, in fact, that one of her mammoth breasts nearly jumped out of her dress. She walked closer towards you.

“Tell you what kid, I like you, so I'll offer you a deal. It's apparent you see something you like, and I've got a husband who is more focused around his business than me. So, how's this sound? For five bits, I'll let you take a picture, any pose you want.” the MILF's voice grew softer. “Or, for fifteen more bits, we can take this somewhere more... private.” she finished, folding her arms, pushing her chest to be more exposed.

You started shaking. Was this lady serious? If she was, what the fuck were you hesitating for!? You had plenty of money to spare!

“Uh...” you stuttered. She leaned forwards, exposing her cleavage in all it's glory.

“What was that, I couldn't quite hear you.” she said, a taunting smile on her face. She already knew your decision. You nodded your head slowly, and tried to make it obvious you didn't already have your mind made up.

“My place! I've got bits at my place!” you blurted. She actually looked surprised, but only momentarily.

“Alright then. Lead on, stud.” she said, taking your hand in hers. You forced yourself to remain calm, and lead the MILF back to your home. On the way, she informed your her name was Spoiled Rich, and her husband was always gone on business, so she never got the attention she very much needed. You were happy to help her out, even if it did cost you a little money.

Once you got her inside your house, all hell broke loose. The second you locked the front door, she shoved you up against the wall and began invading your mouth. Damn, this mare had experience! Her tongue had forced its way past yours in a matter of seconds, despite your best attempt at fighting back. You opted that if you couldn't beat her in a tongue battle, you could dominate her in other ways.

While she was winning the make-out battle, you put your hands on her body, and found the two soft mounds you were looking for. You groped and rubbed her breasts, making her moan into your mouth. Eventually, she let you breath, and looked a tad flustered herself. Once you caught your breath, you suggested taking it to the bedroom. She agreed, and once you told her where it was, practically dragged you to it.

You got her on the bed, and she began kissing you again. While she did so, you managed to free her breasts from their prison, and resumed groping them. After a few minutes, you felt something wet on your hands. You broke the kiss to look at her breasts. Milk was leaking from her swollen nipples. She was a mother after all.

“You know, it's been a while since I've been milked. Partially because I haven't had my breasts properly aroused for a while, but they seem adamant on losing their load now, so I can only trust that you'll finish the job.” she said, holding her breasts up for you. You needed no more coaxing, and put your mouth on one of her nipples. The second you sucked, you were rewarded with a flow of the creamiest milk you'd ever tasted. It was simply delicious! You sucked harder, eliciting a moan from Spoiled Rich. She began panting, so you switched to her other breast, making her pant harder.

Much to your disappointment, milking her breasts had caused them to get a bit smaller, but they were still a lovely size, a fact which you told her, and earned yourself a kiss from. Once you'd had your fill of her milk, you waited for her move.

“So far, you're better than I thought you'd be kid. Let's see what you're packing.” she said, tugging at your pants. You let her practically rip the pants off of you, to which she then tossed them across the room. Your manhood was standing tall and proud, at full alert since the kissing had started. Spoiled Rich mewled at it in awe as she placed a hand on it.

“You're certainly bigger than my pathetic husband. He's not even half your size.” she said, positioning herself so her head was level with your groin. Without warning, she began licking up and down your shaft, a sensation which you'd never felt before.

“Sh-Shit!” you groaned in pleasure. Spoiled swatted your leg.

“Kids these days, no control over their language.” she murmured, while still pampering you. You thought about telling her that you were twenty six, but her licking only caused you to groan more. Eventually, she stopped licking, and placed your member in her mouth.

It took all yourself control and then some not to blow your load right then and there.

Spoiled's experienced mouth took nearly all of your member on the first try, although she did gag a little, considering you were apparently much bigger than her husband. On the second try she downed all of it and her eyes watered, running a few mascara trails down her face. You could literally see the bulge of your member in her throat, something that aroused you more than it probably should have.

As she quickly worked your member, her breasts bounced and swayed, pushing you even closer to your rapidly approaching climax.

After approximately thirty more seconds, you knew you weren't going to last much longer.

“I-I'm close!” you shouted in warning. Spoiled Rich moaned, which you interpreted as a green light to let her have it.

You groaned as you violently came into her throat, Spoiled Rich not spilling a drop of your spunk. You came for about ten seconds before she finally took your member from her mouth. She patted her stomach.

“Damn kid, you sure were pent up.” she said, standing up. You shrugged.

“That was about the normal amount for me.” you said. She looked as if she didn't believe you.

“Well, we'll have to see if you can do it again, but I need to be tended to again.” she said, laying on her back, her bloated breasts sagging to the sides.

“If you would kindly free me of this dress, I'd like to see how hungry you are for some dessert.” she said, smiling. You quickly slide the dress down Spoiled Rich's body, and discarded it completely, staring in awe at her now fully exposed body.

You had been correct before about her pudge, she was slightly chubby, but you loved a soft woman, so it didn't bother you in the least. Her legs also had a nice amount of fat on them, giving them a slight jiggle if she walked just right. You never did like stick legs on a woman. In a word, she was perfect, even for her age.

She spread her legs, revealing her marehood, swollen and leaking with arousal. From what you could tell, she needed to be boned badly. But she apparently didn't want that quite yet.

“Get eating.” she ordered. You willingly complied, and got your face level with her twitching nethers. You began to lick the outer region, which in itself made her start shuddering with pleasure. After a moment of warming up, you shoved your tongue inside, and worked it as hard as you could.

“Oooh! Yes, keep that up!” Spoiled Rich shrieked. You smiled to yourself and continued to eat her out.

After the short time of thirty seconds, she rewarded your efforts by spraying your face with love juices. You were somewhat disappointed she didn't last longer.

Once you finished, she continued to lay on her back, breathing heavily for a minute or so. You took the time to lay atop her and bury your face in her chest. Between her pillow like chest, and her padded stomach, she was softer than a bed. Eventually, you got off of her, and she sat up, a predatory hunger in her eyes.

“That's it! I can't wait anymore. I haven't been fucked this good in a while, and I'm not stopping now!” she said, suddenly pushing you onto your back before straddling your once again erect dick with her marehood.

“Wait! What about a condom!?” you asked quickly. Spoiled rolled her eyes.

“Ugh, forget the condom! If you get me pregnant, I'll tell my husband it's his!” she said, quickly lowering herself onto you.

The moment you entered her, both of you let out a yelp. She was surprisingly tight, which only proved her point of her husband being smaller than you.

“Poor mare, with all of this body, and a less than satisfactory husband. I'll make sure you're walking funny for a day or two.” you said. She moaned loudly at your words.

“Do iiiit! I neeeed it! I don't want to feel my legs by the time we're through!” she screamed.

“As you wish.” you said, grabbing her hips before forcefully thrusting yourself into her repeatedly.

It was probably a good thing you had all your windows shut, because with as much screaming as Spoiled was doing, somepony was bound to figure out what was going on.

Her breasts bounced violently up and down, occasionally flecking milk into your face. You could hear her massive ass jiggling and clapping together, so ou placed your hands onto her plump ass, and squeezed it. She moaned all the louder as she rode you to oblivion.

“Where have you been all my life!?” she shouted as she rode out an orgasm. You had yet to cum, so you continued pounding her perfect MILF body for another few minutes. Eventually, you felt your climax approaching.

“You ready?” you asked. She nodded and pleaded for you to let her have it, so you did.

“AAAAAAAAHHHHHHHHHH!!!” she yelled as you fired your load into her waiting insides, painting them a solid white. You came much more than the previous time, so much that you actually bloated her womb a bit. She looked like she had eaten way to much at once. It was amazingly sexy.

She continued to hump you for a few seconds after your orgasm had stopped, the proceeded to flop onto the bed next to you, breathing like she had just run a marathon.

“You alright?” you asked, somewhat concerned for her because of her older age. She nodded.

“F-Fine. Just a bit... tired.” she breathed. After a few minutes rest you got up and gave her clothes back to her.

“Thank you. I must say, I've never experienced anything like that in my life.” she said, struggling to fit her huge breasts back into her dress.

“I've never had a mare like you in my life.” you replied, smiling. She blushed, and gave you a quick kiss on the cheek. You then remembered her payment.

“Oh, right! I've got to get your twenty bits.” you said, beginning to walk to your dresser. She put a hand on your shoulder.

“Forget about it kid. For giving me an experience like that, I can't possibly charge you.” she said, fixing her hair.

You nodded.

“Just so you know, I'm twenty six.” you told her. She stopped.

“Are you really? Well then, I might have to come back sometime.” she said, smiling as you showed her the door.

“Feel free to anytime.” you told her as she walked back to town.

Once she was gone, you plopped onto the couch, and ran over the previous events in your mind. It was certainly an unexpected event, but it made you wonder...

if going for a walk gave you such a sexy mare, what would going for a run do?