There was no reason to turn back now, at least for the young human. The day was now reaching sunset. Windy cleaned off the leftover jizz and led Anon to the guest bedroom. After arriving she turned to him and rose his shirt over his head and simply dropped it on the floor. He decided to return the favor and undo her skirt, letting the same happen to it.

“Woah…” He says as he gets the sight of her drenched panties.

The mare hooked her thumbs around the string and pulled them down, revealing her glistening pussy. Seeing it seemed to send more blood to the man’s groin.

“So, Anon, are you ready to show this old mare a good time? ~” She says, still holding up her seductive smirk.

“Hey, you want it, you’ll get it.” He replied back.

The mare sat on the edge of the bed and spread her legs. Anon drooled upon the sight and didn’t hesitate this time, getting on his knees. He started rubbing his fingers against her vulva, prompting satisfying hums from her as his fingertips were stained with her juices.

He removed them and replaced them with his tongue which caused her to twitch a bit, but quickly relax as he continued to lap at her entrance. The salty taste hit his tastebuds which only fueled his need to service her. He reached around her legs, resting them on his shoulders as he grabbed her asscheeks, giving them a nice squeeze, much to her pleasure.

She giggled as he continued to squeeze her cutie-marked flank as if trying to mold them into a different shape. He leaned forward, pressing his lips against her lower ones, getting his tongue between them which made her gasp. She then started to moan loudly as he started licking around the inside of her pussy, getting as far as he could whilst still fondling her flank.

“Oh, yes! Just like that, sweetie.” Windy says while placing a hand on his head.

Anon wasn’t going to lie, the guilt had still yet to fully fade from his mind, but he figured that he might as well enjoy what he’s got while he can. Then his eyes caught the attention of her bud and he got a little dirty idea. Without warning, he let go of one of her asscheeks and reached up to poke it a bit, which made her gasp once more.

He decided to pinch it afterward and that made her eyes widen and arched her back as she gave a small scream and then released gallons of her juices into the man’s mouth. He gulped all that he could before pulling away and coughing as some sprayed on his cheek. After she was done, she collapsed onto the bed and the man simply wiped off the stain on his cheek as best as he could before standing up.

“Hey, you good?” He asked.

“A-am I…” Windy needed a second to catch her breath. “Great Celestia, you…” She panted before squinting a bit. “Hoo, you young ones are certainly energetic.”

“Eh, I’ve had some practice.” He says while scratching his head.

“Is that right?” The mare then laid her back on the mattress. “Care to show this old mare what you’ve practiced? ~” She gave him another sly/seductive smile.

Anon was now granted the sight of both lower holes. He stared for a bit before standing up and taking his cock, aiming it at her vulva at first, but then a thought occurred. He looked down, then changed direction for her lower hole. She rose an eyebrow at first before clenching her jaw as she suddenly felt him start pushing his member into her sphincter.

The man groaned as the familiar tightness was already starting to attempt to restrain his member. He reached under and pulled, hoping to spread her hole to make the entrance easier. He pushed more and harder until he finally manages to get his rod right in, making her wings spread out as she moaned in pain.

Anon had to put his hands on her ass to push himself in until he was at least halfway in. He stopped, both him and the mare needing to catch their breaths. So far, he could definitely confirm where her daughter got her ass from. The familiar feeling, the familiar strain, it was all there.

“Buck… buck… Oh…” Windy moaned.

“Oh damn!” Anon says. ‘Man, still not used to the tightness.’ He then thought to himself. “You good?”

“Yes, just… Celestia, quit keeping me waiting.”

With a shrug, the man started moving his hips back and forth, letting her moans and the sounds of slapping skin echo through the room. Anon was beginning to feel less guilty about what he was doing… well, not exactly, just was having an easier time ignoring it. All his focus was on giving this pegasi mare what she wanted.

The man was groaning a bit as the feeling of her bumhole squeezing his member still felt a bit painful. At first, he wondered if her husband was ever giving that hole any attention, then he remembered how Rainbow seemed virgin-tight no matter how much they did it, so he wondered if this was a trait of her family.

Windy reached up and grabbed his shoulders before moving them to his head and pulling his face between her bust. He stopped thrusting for a second before continuing. Though, he got an idea and lifted her off from the edge of the bed, holding her up before pushing until he was balls-deep in her and continuing to rut her.

“Oh, buck yes! Just like that!” She says while hunching over the man, arms still wrapped around him.

Hearing her moans Anon decided to up his pacing, feeling her ass ripple in his hands and her entrance rubbed against his crotch as her moaning got even louder. Her legs tightened around his waist as he did so. He pulled his head out of her bust, forcing her arms down to his shoulders and catching his breath.

He looked at her wings and another idea came to mind. He removed one of his hands from her ass and reached up, grabbed one, and began stroking it, causing her to squeal. Still keeping his rhythm, he continued to rub her wing, which made her loosen her grip a bit and for her tongue to hang out from the side of her mouth.

Anon didn’t stop there though. He leaned his face into the crook of Windy’s neck, and gently nibbled on it. She moaned between her panting before looking down at the man, then removing his mouth from her neck and slamming his lips against his, much to his shock.

He went with it though and pressed back. He didn’t hesitate to fight her tongue with his own. She had shown that she was more experience, her equine tongue especially having an advantage, but he still overpowered her and she was loving it. The kiss got sloppy and spit coated their lips while still not breaking rhythm with their hips.

Anon had a familiar feeling building up and moved his hips faster. As he did, he could feel her juices spray on his crotch. Her eyes opened and rolled up as he continued to pound her ass into oblivion. One final slam and he fired his seed right into her anus.

She grew a small bump in her belly grew in her belly before the man had come to a stop. After a bit, they pulled their lips away from each other and panted for air before they collapsed on the bed.

“Oh fuck…” Anon moaned through his pants.

He pulled out of her, and as he did, his cum squirted out from her anus. Windy opened her eyes and stared at him, then smiled.

“Not bad.” She giggled. “I haven’t felt that good since I was a young filly.”

“You call yourself old? No old lady has an ass like that.” He says before thinking. “I mean, I haven’t slept with any other older woman here so, I guess I can’t really say that.”

“I see.” The mare says before grunting as she felt her ass squirt his cum again.

“That’s gonna be going on for a while.”

The mare giggled again before sighing. The two lay on the bed for what felt like an eternity… okay it was only a minute, but it felt longer than that. Neither really knew what to say after what they did. Anon looked back at Windy’s boobs and seemed to fall into a trance as he stared at them.

“You want another taste? ~” She offered while cupping one of them.

Well, that was an offer he definitely wasn’t gonna pass up. He leaned down and reached just to suck it until something out of the corner of his eye caught his attention. Then his eyes widened in fear. Standing right in the open door was the speedy pegasus Rainbow Dash, eyes also widened, looking mortified.

Seeing the look on the man’s face, Windy turned and saw her daughter looking at them. Slowly, Rainbow’s mortified face turned to rage.

“What…” She says while gripping the knob roughly. “The…” She then clenched her fist tightly. “FUCK!” She was so angry that she spouted out a curse from your world.

“Uh… uh…” Anon stammered before he shot up from the bed. “Wait, wait hold! It’s not what it looks-AGH! I-I mean, I guess i-it is what it, b-but-”

“Oh!” Rainbow dashed up to him, getting right in his face. “Don’t even try to worm your flank out of this. What, my small boobs ain’t good enough for you so you go after my mom’s? Especially MY MOM!”

Anon didn’t have any way to defend himself. A scene like this is a scene that’d put him past his redemption. Any redemption really.

“And don’t get me started on you!” She then pointed at her mother. “Out of all the colts and stallions, you decide to buck my boyfriend?!”

“I’m sorry Dashie, but well… can you blame me?” Windy says while pointing at the man’s member.

“Oh. My. BUCKING CELESTIA!” Rainbow screamed before stomping back and forth while muttering to herself.

“L-look, I’m sorry, I really am. I just…” Anon trailed off before sighing. “I’m sorry, I don’t know if you’ll forgive me or not, but I-I didn’t…” He looked back at the older mare. “Listen, Mrs. Whistles, I don’t want to cause problems between you, your husband, or your daughter-”

“Wait.” Rainbow says as her anger was suddenly replaced with puzzlement. “Say that first part again?”

“Uh… I was saying that I don’t want to cause trouble between her, your father, and you?” He says, mirroring her puzzlement.

“...” Rainbow stared for a moment before glaring at her mother. “You didn’t tell him?”

“Mmm, might’ve slipped my mind.” Windy says with a sly smirk.

“... What?” Anon says, now more confused as Rainbow groaned.

“Babe… My parents are in an open relationship.” She tells him.

“... Again, what?” He says, now more astonished than ever.

“Ya know, like… having multiple partners.”

Anon still looked dumbfounded but started to understand.

“Oh…” He says to himself before looking back at Windy. “But… shouldn’t I… not count since I’m dating your daughter?”

“Oh, it’s really not any trouble dear.” She says while waving.

Well, so much for feeling guilty for fucking her behind her husband’s back.

Rainbow glared back at the man, then grabbed his arm in a tight grip before dragging him out of the guest bedroom. She led him down the hall, naked with his dangling pillar swinging about. She stopped in front of one of the rooms, pushing through the door, dragging him in with her, and locking them in.

“Rainbow, I’m sorry. I won’t-” The man tried to say.

He was thrown onto the bed before he could finish. Next thing he knew, he heard some wooshing, then the rattling of chains, then he looked up, seeing his hands in handcuffs, trapping him to the bedframe.

“Shut it with the ‘sorry’. You wanna make up for it? Stay where you are.” She scolded before she took out a remote. “From this point on, you’re a dildo for the rest of the night.”

As she pressed the button, Anon yelped as he suddenly felt vibrations around his shaft. He looked down and his eyes widened. She had a vibrating-dickring at the base of his member, already causing it to rise.

“Like I said, keep your mouth shut.” Rainbow says as her clothes were dropped to the floor and she was left naked, still looking annoyed.

The tone she spoke in alone sent shivers down his spine. She got on top of him, placing her hands on his chest before scouting back until his shaft was between her jiggling asscheeks. She continued to stare down at him with an even smile before wiggling her hips and letting her lower cheeks smack around his tower to get him hard enough.

Anon was panting and moaning. He was still sensitive after just climaxing earlier and her assjob along with the vibrator made it impossible for him to hold back another one. He kept his mouth shut though, believing this to be karma. He expected Rainbow to be more pissed at him, but if he had to go through this torture to keep his girlfriend from leaving him, he would go through it.

“You still thinking of my mom now?” Rainbow asked him.

“N-no.” Anon stammered out.

“Are you thinking of bucking my mom?!”

“No! No, I’m not!”

“Good. Now shut up and lay there like the toy you are.” She then says with an angry smile.

This was something new to Anon. There were usually days where he’d take the lead and other days where she’d take it, but this whole sadistic and dominant attitude was new to him. Then again, it wasn’t necessarily an unwelcomed thing to him.

She leaned over him and started grinding against him, wrapping her tail around his member, and began pumping his member to add to the torture. So far, it was starting to get the better of him and he could already an orgasm starting to reach. However, he suddenly felt a slight bit of relief as the vibrations stopped.

“Really, Rainbow. I didn’t take you for this.” He heard as he and the rainbow pegasi looked back to see her mother standing there, holding the ring. “To be treating your lover in such a manner.”

Rainbow glared at Windy before speaking up. “You have no room to talk!”

“Yes, I guess, but even so, I believe this was a little far.”

“Oh, I could’ve gone a whole lot farther than this. This is mercy.”

“Is that right?” Windy says before tossing the ring onto the ground. “Of all the things I expected, I didn’t expect this, especially in your old room of all places.”

“This is your old bedroom?” Anon asked before getting a stern glare from the rainbow mare.

“Look at this, you’ve already gotten him all wild up again.” Windy says.

“Mom, get out. I’m not about to let you overthrow my spot as his… as his…” Rainbow trailed off, trying to think. “Well, whatever. I’m gonna show him that I’m a better bucker than you.”

Hearing that, something seemed to snap within the older mare’s head.

“Dashie, care to repeat that?” She asked with a dark look on her face.

“You heard me. Besides, I’ve got the ass you don’t got any more.” Rainbow says back.

Anon’s eyes were now wide, not from the attempted torment from his marefriend, but the fact that she was attempting to roast her own mother despite the current scene.

“Is that right?” Windy asked before sighing, then nodding her head. “Okay then.”

The man still didn’t catch on before the older mare turned around. She then both the rainbow mare and the man’s shock, something completely unexpected, and mashed her ass against her daughter’s and his member.

“Shit!” Anon yelled.

“What the bu-?! MOM!? What are you doing?!” Rainbow practically screamed.

“Sweetie, you wouldn’t have that ass if it weren’t for me. You may still be young, but I’ve still got more experience.” Windy says before pushing her cheeks against her daughter’s, causing Anon to grunt. “So, as much as I love you, I’m not about to let such slander slide.”

‘What?! Where did the talk about how to treat your boyfriend go?’ Anon thought to himself, still in disbelief.

“You can’t just but in! This is supposed to be our time!” Rainbow yelled as she tried to shove her mother back with her ass.

“Well, you should’ve thought of that before challenging your mother.” Windy says doing the same.

“This is supposed to be a punishment, you can’t just turn it into a reward.”

“Too bad. I’m not going anywhere.”

The two continued to try and shove each other off, much to Anon’s pleasure as his member was constantly being squished back and forth between their asses. While they were arguing, he was panting and breathing heavily. If he wasn’t already close before he sure as hell was now.

Then, his balls churned, his shaft twitched and then, it happened. His member fired cum between their asscheeks, stopping their bickering as their tails, wings, and backs got covered in it. He lay in bed, wrists still cuffed to the bed frame, panting for air and face so hot it felt like he would’ve melted on the spot.

“So, guess that makes us tied now?” Windy asked.

“Yeah right, that was was all me. I know what my boyfriend likes, and so does…” Rainbow began to say smugly.

But then as she looked back at Anon, seeing his eyes squinted and his breathing still heavy. Something seemed to smack her back to her senses.

“Oh, shit, shit! Anon!” She says as she quickly got off and uncuffed him then checks his face. “Are you okay?” She asked, not getting an answer. “Oh, shit, I’m sorry.”

It was like night and day that she suddenly switched back to being the loyal and caring marefriend she was. Anon coughed before clearing his throat and looking back at her.

“C-can I… just… get some water.” He asked, still panting.

“Right, got it.” She then sped out of the room before coming back with a cup of water. “Here.”

He took it and started to drink, stopping for a few moments to catch his breath. He continued until the cup was empty. Afterward, he started to breathe more steadily, much to the rainbow mare’s relief.

“Anon, I’m so sorry, I am so sorry! I-I didn’t mean to go this far-” Rainbow continued to speak a million words per second.

“Rainbow!” Anon says, with a hand up. “It’s okay…” He sighed before making eye contact with her, having finally cooled down. “It honestly wasn’t that bad.” He says while giving her a reassuring smile.

The mare sighed before lunging at him, pulling him into a hug. He returned the hug… in spite of his arms getting covered in his own jizz in the process. He was still a little caught off guard by her sudden shift in personality but decided to be the caring boyfriend he was known for.

“Oh, you two are just adorable.” Windy says in a cheery tone.

“Mom, get out.” Rainbow groaned, not moving her head from the man’s cheek.

“Alright, alright. But…” The older mare was about to leave before saying- “Would you mind if I have at least one more turn with him?”

“Are you serious right now?”

“Just one more then I’ll be done.”

Rainbow glared at her, then looked back at her boyfriend, then sighed.

“What do you think?” She asked.

“Uh… if you don’t want me to I won’t.” Anon tells her before closing her eyes to think.

“Wait till my turn is over.” She says before pushing herself up and looking back. “You still hard?”

“Uh… well, after that first session, I uh…”

“Alright, let’s do this.”

Rainbow lifted her hips and pushed her pussy on his member, moaning as it was going in slowly. However, despite the restrictions, he managed to slip in.

After a moment, she started bouncing on him, letting her moans echo through the room. With his hands free, he grabbed her hips to assist her in doing so. Yes, it was tight, but he still decided to push past it.

The rainbow mare leaned down and captured his lips, immediately shoving her tongue into his mouth, entangling it with his own. He kissed back, returning the attention. She then moved her hands down and began feeling up his body, brushing her hands up from his abs to his chest, then up to his face, holding him in place.

Through the window, the sky had darkened as the stars and moon came out. Anon reached and gripped Rainbow’s ass and upped the speed of his thrusting, making her moan into his mouth. He squeezed her pillowy asscheeks whilst keeping rhythm, her tail swishing around while her wings spread and started to lightly flap.

Despite the scene, Windy was watching with a proud smile as she watched her daughter make love with this man. Although, while she was in awe by the sight, it was starting to get to her a little. She placed a hand over her entrance, which still had not been penetrated for the night, and began to rub her outer lips.

The two eventually separated to catch their breaths, panting with a string of saliva connecting their lips. They stared into each other’s eyes.

“You know I love you, Rainbow.” Anon says to her.

“I-I know.” Rainbow says between her moans.

He removed his hands and cupped her cheeks before reconnecting their lips and going back to battling with tongues. Then their hips started going faster again and sure enough, she came, spraying her juices all over his crotch, then he came, shooting his seed into her cavern.

They separated again and Rainbow fell to the side, panting along with her lover who was still cumming inside her and her belly began to slowly expand. It became big enough to look like she was halfway through pregnancy before it stopped and his member slipped out of her entrance, allowing what remaining semen to flow out.

After a bit, they stared into each other’s eyes. Rainbow smiled and snuggled against him.

“You dummy.” She laughed.

Anon didn’t say anything and just hugged back. That was until the sound of throat clearing caught their attention. Windy gave a little wave as her daughter groaned.

“Okay.” The rainbow mare says.

“By the way, should I be expecting grandbabies sometime soon?” The older mare asked.

“Nah, from what I hear, we can’t crossbreed thanks to genetics.”

Hearing that, her mother’s ears dropped. She seemed saddened by the idea that she won’t be a grandma, but then again, it also excited her as she didn’t believe she needed protection.

The two separated, Rainbow Dash lying close to the edge of the bed as Anon got up. Windy then laid her back on the bed, spreading her legs out. The man got on the bed in front of her, and aligned his member with her vulva before taking her hips pushing it into her. Like her daughter, there was some restaint, she moaned at the feeling, before he was fully in her.

“Yeesh, I will never understand how ponies can remain so tight.” He huffed.

“Just get on with it already.” Rainbow says, a bit annoyed.

Anon looked at her mother who seemed to be indifferent about the whole thing before he started thrusting repeatedly. She gasped at first before smiling as the man was now rutting her. Problem is that he was now extra sensitive from past four sessions, so he didn’t know how longer he’d last this time. None the less, it was clear that the older mare still enjoyed.

Rainbow turned around to not look, though it was clear that she could still hear. Anon looked at her, feeling a bit bad, however, he was taken out of that thought when Windy reached up and pulled him down to her breasts while wrapping her legs around his waist.

“You haven’t given these attention in a while. How about you treat them to such? ~” She says, seductively.

He wasn’t dittered and took ahold of her breasts and started sucking on one while sucking the other. Her moans had increased along with her grip on not only her arms and legs, but her pussy.

As he was bucking his hips, he thought back to all that had happened. One second that he was going to visit Rainbow Dash’s parents, next second, he got a titty fuck from her mother, fucked her in the ass while making out with her, then got a double buttjob from both of them, fucked Rainbow in her childhood bed, and now was doing the same to her mother.

Anthro or not, this a dream most people would kill for. And he didn’t think he’d have to worry about the man of the house as her parents were said to be in an open relationship. Damn was he a lucky, especially for someone who was literally eighteen.

It was only so much longer before he could feel his end coming up. He moved his hips faster, and swapped breasts, sucking on the other. After about another minute, her head leaned back and she let out the loudest moan she could as she came on him and he came in her, filling her with whatever was he had left.

It was long before her belly began to grow and was now also looking as though she was halfway through pregnancy as well before he was done. He pulled out of her and heaved before falling onto the bed between the two, panting as his tower fell limp.

“Oh…” He huffed before wiping his forehead. “That was… something.”

“T-that was amazing.” Windy moaned out. “You and Bow… b-both of you… are the best.”

To that, Anon sighed before turning away. Rainbow then laid by his side, wrapping her arms around him, hugging him.

“So, how do you feel?” She asked him with a smile.

“I… feel like I’m gonna need a week before doing anything sex related?” He smiled back at her as she laughed.

“Yeah, figures.”

The two then gave each other a short yet passionate kiss before they stared into each other’s eyes… then the moment got brushed to the side as Windy scooted up and took his other side.

“I hope this doesn’t turn into a one time thing. I’d love to have you and my husband take me at the same time.” She says.

“Ugh… mom…” Rainbow groaned with her face in her hand as her mother laughed.

“Still though.” Windy says. “I’m glad that my baby has found someone to love her in such a manner. You better keep her satisfied now.” She says before kissing him on the cheek as her daughter rolled her eyes.

“Right, but I’m still the bigger priority.” The rainbow mare asked.

“Of course you are. Don’t worry.” Anon says before hugging both of them closely.

Rainbow blushed before smiling as she snuggled up against him. Well, now he had two mares he could bang without trouble or even the worry about them getting pregnant… well, that was what you thought anyway, but… if only they knew to play safe-

“Wait, Rainbow, I got just one question.” Anon asked as his marefriend looked up at him. “Where is your dad?”

“Huh?” She didn’t catch on at first, but then realized. “Oh right. Ya see, he wanted to see where you were living and I decided to take him over to your place. I got to introduce him to your sister and as we were leaving he decided to go to the bar.”

“Is that right now?” Windy asked before sighing. “Guess he couldn’t wait for cider. Leave him be. I’m sure he’ll be back at some point.”

Author's Note

AHA! Yeah, little hint… he didn’t go to a bar.