Anon meets Rainbow's mother

“You know what, I think this might be a good time to bring it in here. What do ya say, honey?” Bow says while standing up.

“Really? It hasn’t been that long.” Windy asks.

“I know, but I think this guy deserves some.” He says as Rainbow groans into her arms again.

“Wait, wait, deserve some of what?” Anon asked, confused.

“He’s talking about cider.” Rainbow explained, muffled.

“Yeah, I got a couple of bottles. Be back in a minute.” Bow says as he went to the kitchen.

“D-what, wait! I’m only eighteen! I can’t-and he’s already gone.” The man sighed before scratching his head.

“You’re only eighteen?” Windy asked, curious.

“Uh, yeah?” He answered awkwardly.

“Hmm, I see. So my little girl is into younger colts.” Windy says while giving a sly look towards Rainbow who still had her head down, just sighing into her arms.

“Y-yeah, haha.” He awkwardly laughed back.

Of course, Rainbow Dash was a few years older than Anon, but being that the gap was small, it wasn’t a big deal. Then again, cider was basically the equivalent of alcohol in Equestria, and even in another world, he figured he wasn’t old enough to have any kind of drink. Oh well, at least he seemed to be making a good impression on her parents. At least if her dad was going to offer him a drink.

As he heard the clattering and the squeaking of cabinet hinges, he suddenly felt something touching his leg, causing him to jump a bit. It felt like a foot that was stroking up his shin through the fabric of his pants. He turned to Rainbow, finding her head still in her arms, not paying attention.

Confused, he lifted the tablecloth, however, whatever seemed to be rubbing his leg already left. He looked back at his pegasus girlfriend and still no sign of her being the culprit. Then again, she could’ve been putting on an act, but he was a bit miffed that she was being hypocritical. He shook his head, sighing a bit in annoyance.

Then he felt something brush against his knee. He quickly lifted the tablecloth again, only managing to catch a glimpse of the culprit before it fled. However, it didn’t go in the direction of his supposed marefriend. His eyes widened before he turned and saw that she still wasn’t acting up or anything. He then looked forward and there it was.

Her mother: Windy Whistles was giving you an odd stare. At first, he didn’t catch on, but then he jumped as he felt something poke his crotch and looked down. Poking against his crotch was a foot covered in baby-blue fur. That gave him the hint and he knew who was trying to get his attention.

It came to a shock that as a shock to him as he looked up and now Windy was giving him a seductive stare as she rested her cheek in her palm. He blushed bright red, then felt her press her sole against his crotch, causing him to flinch. She was still looking at him with a sly gaze, she knew exactly what she was doing.

He tried not to let her get to him, but he was already feeling his pants begin to tighten around a bulge. Taking a glance over at Rainbow, she seemed to still have her head in her arms. Well, that didn’t help him in the slightest, especially now that he could feel the older mare’s foot start moving again.

His boner pressed against the fabric as the older mare continued stroking it, making it harder with each second. Anon tried to keep himself together. The last thing he needed was to be getting off from his marefriend’s own mother, especially right in front of her.

Just as she started to fiddle with the zipper-

“Hey, sorry!” He heard Bow call out and immediately Windy’s foot disappeared under the table. “I couldn’t find any. Could’ve sworn we had some left.” The stallion then says as he enters and sat back in his seat.

“Yeah, well, I think we can deal with it for tonight.” Rainbow says finally raising her head.

Anon sat, stone/red-faced, silent, and unmoving. He just stared at his boner pressing against the tablecloth. The silence seemed to alert Rainbow as she turned to him.

“You okay, babe?” She asked, slightly concerned.

“Y-yeah, uh…” He answers before looking around. “I-I gotta go to the bathroom.” He then stood up and practically ran off.

“W-wait, Anon!” Rainbow called.

“It’s just down the hall, first door on your right!” Bow says, trying to be helpful.

Anon ran into the bathroom and shut the door, back against the door. He leaned his head against the door before looking back at his boner.

“Great. Just what I needed to deal with today.” He groaned before sliding onto his butt.

This was just great. He was just making it good with his girl’s dad so well that he wanted to share this world’s version of alcohol with him. How would he feel knowing that his wife gave him a footjob without him knowing, let alone the fact it was the guy dating his daughter?

Then, there’s Rainbow. Oh, he knew that she would take it worse if she found out. Sure he hadn’t been with her as long as usual, but he’d hate to see her face if she found out about what happened, much less how she would react.

Then there was a knocking at the door, causing him to flinch.

“Babe, you good in there?” He heard Rainbow’s voice and sighed.

“Y-yeah, just… gonna be in here for a while.” He says, trying to sound convincing.

“Okay well… we’re gonna head out. You gonna be good till then?” She asks.

“Why are they suddenly-?” He mumbled to himself before speaking up. “Yeah, I think I’ll be good.”

“Alright, see you when we get back. Make sure nothing happens to this place.”

“You got it.”

He leaned against the door to listen, hearing the front door open and close. Whatever the reason for her and her parents leaving, it must’ve been a sign from the god of this world. Despite his sins, Anon thought he was granted mercy at a time like this. However, there still was one problem. His boner.

He looked down at his pants, seeing the bulge, begging to be released. While he may have promised Rainbow he wouldn’t do anything dirty in her parents’ house, this was probably the best time for him to take care of it now that he was the only one in the house.

So he stood up, went to the toilet, opened the lid, then unzipped his pants, whipping out his member. With a sigh, he took hold of it and started rubbing himself off as best as he could. He had inhaled deeply as he did so. So far he seemed to only make the problem worse as he only got harder with each stroke.

He was a minute in and again he didn’t make much progress. He mentally cursed out Rainbow’s mother for doing this to him. Then it hit him, maybe he could just imagine Rainbow giving him a hand job.

So he did just that, he imagined her crouching down right in front of him, working her hand around his member. It seemed to be working, at least, it seemed that way to him. He was still going to take a while, and he could only hope the others won’t be back for a long time.

Slowly but surely, he started to feel like he was finally making progress. His imagination seemed to be going wild as he could almost hear her lust-filled moans, feel her furry hand taking over for him, going down to the base, her other hand fondling his balls, and her lovely equine tongue going from the bottom of his shaft right up… to his… tip…

Wait… didn’t Rainbow say that she was… and she couldn’t have… as he began to realize, Anon’s eyes slowly opened widely. Then he looked down and saw that it wasn’t Rainbow rubbing and licking his shaft… it was her mother, staring right up at him with her eyes half closed.

He stared back at her… slowly regaining his sense.

“DAH!” He screamed, jumping back before slipping and falling on his ass. “What the f-Wha… WHAT?!” He shouted. “What are you doing?!”

“Oh, forgive me for not letting you know. I just figured you’d like-” Windy starts to say in a sultry tone.

“Why would I-Dh…” He felt his voice caught in his throat for a moment before gulping. “I-I thought you left with…”

“Not all of us left. I decided to stay.” She says before looking back at his member. “And I think I’m glad I did.”

Seeing her gaze, he covered his crotch, though he could only cover so much of it. It didn’t take long before she removed his hands and continued to stare.

“I gotta say, I was a little shocked by the shape. No sheath, no flathead… I like it. ~” She says before grabbing it and starting to jerk him off again.

“W-wait!” Anon stammered out, face beat red. “You can’t do this!”

“Oh, is something the matter?” She asked, acting oblivious.

“You’re literally my girlfriend’s mom! That should make it obvious from the start!”

“Well, if that’s the case, maybe we can make this our little secret.”

“T-that doesn’t-” Anon stammered.

He again found his voice stuck in his throat as Windy continued rubbing him off. She fondled his balls, he couldn’t bring himself to voice how wrong this was as he was lost in the pleasure of the mare’s handjob. She didn’t seem to care about committing infidelity while her husband and daughter were out; despite knowing such, the man’s member was betraying him.

Then he took a second to look back at her, reexamining her. He recalled her ample bust and began to take note of her lighter freckles and magenta eyes that her daughter inherited. Now that he was getting a different look at her, he couldn’t help but notice how sexy she was and how much of a milf she truly was.

She seemed to take his silence as a good sign and licked his tip, making him tightly close his eyes.

“Let me ask you this.” She says before crawling up until her face was just inches from his. “Have you done this before?”

He breathed heavily, face feeling like it was gonna go up in flames.

“A-a-a few times… s-several actually. Rainbow and I have been… well…” He struggled to get the wording out being more nervous and yet turned on.

“Did she take your first time?” The mare asks, getting the tiniest bit closer while rubbing his member faster.

“Y-yes.”

Hearing this, her smile seemed to grow wider.

“I’m glad to hear that. I wouldn’t want to take that away from my little girl.” She says as she slows down with her rubbing. “That being said though…”

Then she moved back which allowed him to relax a bit before watching her undoing the buttons on her shirt and letting it fall to the floor, revealing her large, what was assumed to be, double E-cup boobs in an orange bra. Then as she reached back, undoing it, it practically popped off her and made them look even bigger as they bounced free, her furless nipples peeking out.

If it were possible, his nose would’ve exploded with blood. She continued to smile before pushing herself up so that her breasts were in his face.

“There’s just so much that a filly can do compared to a mare with experience. ~” She says as she straddles him, placing his cock between her buns. “So…” She then held one of her breasts up to his lips. “Do I have your interest now?”

His boner practically begging for relief, Anon decided to give up trying to resist and gave in. He opened wide and allowed her to place her nipple in his mouth. As soon as he felt her areola against his lips, he sucked like no tomorrow. She giggled lightly before biting her lower lip, taking his hand and placing it on her other breast while placing her own hand on the back of his head.

He could feel her wiggle her hips and her asscheeks rub against his tower as he squeezed and massaged her boob whilst circling his tongue around her nipple on the other. She definitely had a leg up on her daughter in terms of chest size, though, he sure knew where she inherited her bum from.

Of course, he did feel guilty, not just about Rainbow but also her father too, but he also couldn’t help himself. Unfortunately, even he wasn’t the purest being on Earth… or Equestria. He got turned on by many mares in Ponyville and some even flirted with him, even after getting into a relationship with Rainbow.

He of course didn’t give in to them, but Windy catching him off guard and going straight was a different story. After a minute she pushed herself up and pushed his head off of her breast. Anon didn’t know whether to be relieved or be saddened.

“My, you must’ve enjoyed yourself.” She says.

“Sorry, I just… kinda got… a little carried away.” The young man responds.

“Oh, well if you like my boobs so much, let’s see if you can handle them.” She says while shuffling down and spreading her bust, then sandwiching his member between them.

“HOLY-!” Anon bit his lower lip to keep himself from cursing.

Windy started mashing her tits together against the man’s shaft, causing him to shift his head to look at the ceiling breathing a bit more heavily than usual. The soft pillowy skin rubbing around his rod made precum start leaking already, much to the mare’s pleasure. She gave the tip a kiss before licking it, causing it to twitch.

“Naughty, naughty, boy. Getting off this much from an old mare such as myself? ~” She giggled before squeezing them together.

“I-I mean… k-kinda, yes.” Anon stammered out.

“With something this big, I think I know how you got Dashie to fall for you.” She says teasingly.

“W-well, not really. We did the whole process of dating first-!”

Anon cut himself off, stifling a groan. Then his eyes went back to Windy’s, seeing them half-lidded and a dirty smile on her face. Then looking down and seeing her jugs working around his shaft. Then she starts licking around the tip, causing his member to twitch and twitch as his balls began to churn.

Without warning, his rod squirted cum like a fountain between her cleavage. The mare leaned back, closing her eyes, but turned back quickly and opened her mouth wide. Big droplets landed on top of her jugs and dripped down them, same could be said with her face before it stopped. Her mouth was filled to the brim before she closed it, in a single gulp, she opened it again to breathe, revealing nothing left.

“Goodness.” Windy says while wiping some from her eyes. “You sure were pent up.”

“A-actually, that’s the normal amount. At least for me.” Anon says to her.

“Oh, is that right?” She asks as she gains a smirk before getting up close him, cum still dripping from her chin. “Then how about we go somewhere more comfortable?”

“U-uh…” He stammered while leaning back to keep himself from getting touched with any.

“I haven’t had a good bucking in a while and judging by your current state-” She says while turning back to his shaft. “I think I already know your answer.”

He stared at her, she stared back. He thought about what she said and looked back at his standing cock.

“Ya know what, fuck it.”