The Lost Lovers

Pinkie woke with a yawn, she'd never had a more relaxing sleep in her life. She briefly wondered why it had been such a restful sleep until she got out of bed and felt the familiar feeling of a big horse cock dildo still in her ass just barely held in place by her panties. She smiled and removed her panties, allowing the dildo to unceremoniously fall out of her ass and thud to the floor, Pinkie shuddered at the odd sensation of being so suddenly empty in a hole she liked having stuffed with thick cock as much as possible. Time for her daily anal exercises! Pinkie put on her usual exercise get-up, light blue headband with matching shorts, light yellow shirt with matching knee high socks, all topped off with striped light yellow and light blue bands on her arms. Once she was ready, she got up her exercise mix playlist up on her phone and pressed "play", immediately her room was filled with the thumps and booms of music made to trigger feelings of the need to knuckle down and get to work!

Pinkie always considered it important to flex her anal muscles and keep them trained, while it may have been easier and perfectly safe to just let her ass be as loose as possible, she liked to think that having her back door put up at least a little bit of resistance added an extra something to the constant butt fucking she casually engaged in for both her and whoever was doing the fucking. Speaking of which, she had a bakery to run and a one hundredth customer to look forward to! Pinkie Pie took off all of her exercise gear, got dressed, brushed her teeth and immediately went downstairs where she had just enough time to eat a hearty breakfast of pancakes covered in syrup before the first customer arrived. After serving several customers that morning, number one hundred arrived in the form of Pip, this was exciting for Pinkie because she had just days ago arranged his 18th birthday party and now she had the chance to give him his first taste of anal sex, she would have done it at the party but his mother knew what kind of girl Pinkie was and didn't want her son Pip immediately diving dick first into the nearest fuck hole on the day he finally became legal.

"Well hello there Pip! Nice to see you! It's good timing as well, because surely you've heard of my one hundredth customer policy? So what do you say? Wanna head upstairs and bang this baker's booty?" Pinkie turned around, showing off her large buttocks.

Pip thought before going "No that's OK, I've already had some anal sex today", Pinkie's jaw hit the floor and her eyes widened cartoonishly as she gave a genuine gasp, how had someone gotten to him before she did?! Pip continued "There was a brief window of time at the birthday party where my mother wasn't watching over me and before I knew it I was in my bedroom balls deep in a woman's ass, it was so magnificent I just had to visit her again today! I assumed you would have gotten to me first but it looks like someone beat you to it!" Pinkie Pie was majorly pissed off, it looked like there was a new anal whore in town and she wasn't too pleased that this girl had enough skill and determination to bag a barely legal boy she'd had her eye on for a while.

Pinkie glared and said "Who is she?"

Pip chuckled nervously and said "Uh... she asked me not to say...", Pinkie had to find out who this girl was but she wasn't about to sacrifice her principals, she still had a one hundredth customer to serve.

"So, what can I get you Pip? Oh and more importantly, what kind of sex are you in the mood for if not anal?"

Pip said "Well I just wanted to pick up an apple pie, as for the sex... um, well I have always wanted to kind of try... pegging......", Pinkie's face lit up a little, she did always like the kinky ones.

"Hmm, not exactly my first choice..." said Pinkie "But I like it! Alright Pip, let's do this!" Pinkie grabbed him by the arm and dragged him upstairs to her bedroom. As soon as they were inside her room Pinkie said "OK Pip, you get naked and get on all fours on the bed, then I'll wear my strap-on and give you a good pounding, m'kay?" Pip just nodded and did as instructed, slowly stripping a putting his clothes to one side, Pinkie kept on almost all of her clothes except for her skirt, she didn't want the skirt getting in the way or obscuring the view of her strap-on sliding into a tight virgin ass hole. Retrieving the strap-on from a drawer she slid it up her legs and tightened it around her waist while Pip got in position and waited patiently, Pinkie unscrewed the cap from her bottle of lube and spread a good amount on her strap-on, twisting her hand around it while stroking the entire length to ensure every inch was as slippery as possible. Getting behind Pip, she spread a generous amount of lube on his pucker, Pip gasped slightly at the cold substance being applied to his back door, especially when Pinkie saw fit to gently insert half of one finger to get some of it on the inside of his bottom.

Before Pinkie proceeded to try and enter him Pip said "Pinkie... is pegging... gay?"

Pinkie giggled and said "Of course not ya big silly! You're still having sex with a girl right?" That was a good point, Pip wouldn't allow this to happen if it was a boy doing it. Pinkie moved forward and held onto Pip's shoulders as she pressed the tip of her strap-on against his previously unpenetrated rear, as could be expected, Pinkie had to put a fair amount of pressure behind her insistent attempts to get inside him before the tip finally popped inside. As soon as it was in Pinkie was, unfortunately, not really in the mood to be the most gentle lover and thrust forward, sinking the whole thing inside Pip in one go, Pip cried out in a strange mixture of pain, discomfort but also an immense sense of pleasant fullness that somewhat masked the other two things he was feeling. Pip had barely recovered from the initial thrust before Pinkie started hammering away at him, he felt so... slutty. Whilst Pinkie was pumping away in his ass she said "How does that feel Pip? You like it?"

In between the grunts and moans he was making Pip simply went "Uh-huh, I feel so full... I really like it..."

Pinkie giggled and started going harder, she wanted to go as deep as possible to make sure that the strap-on was hitting his prostate, considering that all a doctor needed to find it was one finger she felt pretty certain that she was hitting the mark, plus the fact that Pip was moaning like a whore with a very stiff erection, that was also a pretty good indicator. Pinkie Pie decided to reach one hand underneath Pip to start stroking his cock in time with her thrusts, she could feel it throbbing as he got closer and closer to orgasm, she smiled mischievously and said "You gonna cum bitch? Gonna shoot you pathetic load from having your ass fucked by this fat fucking dick?"

Pip didn't respond in words, instead just cried out as he came all over the bed sheets below, Pinkie let go of his cock and gently fondled his balls as if silently encouraging them to empty themselves as she continued to fuck him. Once Pip went from moans to mumbles and his cock stopped spurting spunk, Pinkie slowed down her thrusting until she stopped altogether, she pulled out and said "Did you like that?"

Pip nodded, drool dripping from his lips, he had clearly enjoyed this a lot more than Pinkie thought.

The End