Dr. MILFlove or: How I Learned to Stop Worrying and Love the Cougars

by TheWingman

Dungeons & MILFs(Elaina - AKA: Button's Mom)

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Last week was one hell of a party. Even to this day, especially after high school, you’re still amazed that Pinkie Pie can throw one hell of a party. In between your job hunts and your scholarly duties, you still managed to keep a stable social life and hang with your friends when time allows it. Even now, as you walk along the streets of suburban Canterlot, you were excited about tonight because your friend Button Mash and his mother are throwing a LAN party with some of his friends and hers. Hours upon hours of scarfing down pizza and soda while playing such great hits as CS:GO, Red Alert 3, Left 4 Dead 2, MvC3 and Smash Bros await you and your mutual friends that want a night to let loose and have fun.

As you were getting closer to Button’s house, your phone vibrated briefly in your pocket. Pulling it out, you saw a text message from Button Mash himself.

“Yo Calculus, Rumble’s rig is on the fritz. From what I can tell, it shouldn’t take me no more than say three hours to get it fixed. Go on ahead to my house and you can help my mom get things squared away. I’ll be there as soon as I can get this machine fixed. Peace!”

You couldn’t help but let off a small chuckle at the situation with Rumble’s “Mjolnir” as he likes to refer to his computer as. Though you and Button Mash went to separate high schools, the both of you attended the same elementary and middle schools. Though he was upset that your parents put you in Crystal Prep, you still kept in regular contact with him. Hell, you attended his graduation party and got him the latest DOOM. He had a substantial knowledge when it came to computers and helped build your first rig. Knowing how long it’ll take him to fix Rumble’s problem, you kept on your course towards his house with your rig in tow.

Eventually, you arrived at his house. It looked well kept and the grass was vibrant green color. Button did mention that his mother had a bit of a green thumb. Walking up to the door, you gave it a few good raps on its surface. After a few seconds, the door opens, revealing a sight that made your heart skip a beat.

“Hello there, Calculus!” Elaina, Button’s Mom, said. “No doubt my little Button told you he was helping a friend, right?” Elaina was, as you would say… a bomb-ass lady. Curvy and bubbly, cheerful and motherly, with a nice long hairdo with a bow at the end, she had her own charm to compliment her looks for a woman that’s nearing 40. Though her husband is the breadwinner of the household, she does a few part-time stuff to make sure her family has money for the fun stuff. Oddly enough, like you and her son, she was a bit of a gamer as well. Who would’ve thought that a mother likes to play video games. Taking a slight cough, you reorient yourself and made eye contact with her.

“Yeah,” You replied. “He texted me about it five minutes ago. He said it’ll be a few hours. He also told me to help you get things squared away.”

“I see.” She replied with a veiled moan. “Well, all we have to do is get the tables in the basement setup and everything else hooked up. It’ll be done faster now that I have an extra pair of hands for help.”

“Okay, let’s get to work then.” With that exchange, you set your rig to rest in the living room and followed Elaina into the basement. However, as you were climbing down the stairs, you noticed she was giving her rear end an added sway with each step. Though you would find it arousing to where it left you frozen in place, your past experiences with some of the older women you’ve known had let your mind numb to such sights. Quickly shaking the sight from memory, you helped Elaina set up the power strips at every outlet you could find. You also had to make sure that the tables would be able to reach them, considering that computers and consoles will be in use. After the power strips were all set, Elaina called to you with a ladder in hand.

“Calculus, can you be a big helper and hold this ladder while I place this router? It’s a bit rickety and it makes me nervous.”

Complying with her request, you meandered over to the ladder and held it in place, allowing her to setup the aforementioned router. For a such a relatively young MILF, Elaina had both a youthful appearance and geeky nature along with the refined curvy features of more older women, a nice combination, one in a million. She wore a white tank-top with a short blue skirt. As she clambered the ladder and fiddled with the wires and velcro, you got a good glimpse of her tan red lacy panties, barely veiling her puffy wet vulva.

The sight… the all too familiar sight made you desire nothing more than to lay her on one of the tables and rut her like a wild beast in heat. But, you’ve felt these thoughts weren’t kosher because she’s your friend’s mother. However, you are Dr. MILFlove and knowing that Elaina is on CHS’s parent-teacher council, she likely knows about your exploits. With yourself on guard, you decide to shift your mind away from such lecherous thoughts and decide to strike up a friendly conversation.

“So Elaina,” You started. “Where’s your husband at?”

“Sparkplug?” She replied “He’s on a business trip in Manhattan, they’re probably gonna make him the regional manager for the GoGoTire chains in this state.”

“Hmmm, sounds like he’ll be one busy man, I take it.”

“Busy, yes. But hey, At least it’ll allow for more wiggle room on the budget side of things. With him gone for a few days, it allowed me to do this sort of party, knowing me and my son’s mutual interests.”

“Vidya games, right?”

“Exactly.”

“Who would’ve thought that an older woman like video games. Interesting.”

“Well hey, I was young at one point, you know.”

“Heh, true, true.”

Elaina then finished setting up the router and cables. From your view, it looked a bit like a kraken made of wiring and circuitry, considering all the ethernet wires were all dangling from the metal box above. With everything setup, there was nothing else to do but wait a few hours for the event to start.

“Well, since just about everything is in place, wanna play some Street Fighter V?” Elaina asked.

“Sounds good, getting a little bored myself.” Following her back up to the living room, you and Elaina sat in front of the television and powered up the ol’ PS4. When you saw her username on the home, you were in shock as you were reminded of an embarrassing defeat. A week ago, you were on an amazing win streak against random players in SFV’s multiplayer. When you got to what would’ve been your 50th win, it was against a player named “MadameKrieg747”, the same username as Elaina. You were barely given any time until she won all two rounds against you. It was a crushing defeat and now… you were in the same room with the person that stole your thunder.

“You.” You growled slightly. “You’re the one who robbed me of my win streak!” Elaina then turned to you with a wry smile.

“So, how embarrassing was it, noob?” She replied with a chuckle.

“It killed an amazing streak I was rocking!” You said as you picked up a controller. “Now, I’m so gonna enjoy this little rematch of ours.”

“Well, try to beat me if you can, WardawgAlpha.” Calling you by your username made your blood bubble with pride and adrenaline as you chose Vega and Elaina chose Cammy. You both decided on a random stage select, wanting to get to the fight, post haste. When the fight began in earnest, you were quick to dodge and counter her attacks, netting you a round of victory. However, almost as if she pulled a clutch, she put you on the defensive the following round which resulted in her victory when the time ran out as she had the most health.

When the tie breaker round began, both you and her brought your respective A-Games and began matching her blow for blow. When there was 30 seconds left on the clock, the both of you had tiny slivers of HP left. One connected attack will decide the victor. Elaina went for a jumping kick. You anticipated she was going to and went for an uppercut. Your hit was the first to land and Elaina’s character was KO’d. Finally, your defeat was avenged.

“Hells Bells!” You shouted as you raised your arms in the air, humming the aforementioned song. Elaina was none too happy about her loss.

“FUCK!!!” She shouted as she, without warning, accidentally slammed a fist down hard onto your balls in impulsive anger. The shock and pain from the blow was so much that it caused you pass out. The only thing you heard as you slipped out of consciousness was Elaina shouting:

“OH SHIT, SORRY!”


When you came to, you found yourself on a bed built for a couple. You immediately figured it to be Elaina’s bedroom. You began to feel a chilly presence develop on your crotch. Lifting your head a bit revealed it to be an ice pack on your genitals, unveiled by your boxers and jeans. Though the pain subsided for the most part, you still felt a bit sore in the sack. But, you’ll work through it and soldier on. About five minutes later, Elaina walks in, looking regretful and apologetic.

“I’m so sorry about that, Calculus.” She said as she sat down on the chair next to you. “I just carried away, didn’t mean to do that.”

“No worries.” You grunted. “People make mistakes, just… watch where you land a fist next time.”

“No worries.” Elaina sang as she moved a hand near your crotch, taking off the chilling bag of ice. “Does it still hurt down there?” She, in a non sexual way, lightly squeezed your nads with her hands. You felt hardly any pain, only the residual soreness.

“Just a bit sore, that’s all.” You moaned as she continued to fondle your sack. Then, you felt a stirring in your loins as she massaged your testicles in a sensual way as opposed to how it was before. The grin she sported was one you’re all too familiar with, the signature smile of a cougar that’s staring at her prey. Eventually, the thightness bloomed into a full-on hard on. You were amazed that you were able to sprout an erection when got punched in the nads so hard.

“Hmmm,” Elaina said as she say your erection, uncovered by clothes of any kind rise and stiffen. “It seems your joystick is a little stiff. Heh, it’s gonna need some…” She then took your tool in hand and looked you seductively in the eyes. “ recalibration.”

“Heh, using double entendres I see.” You chuckled as she began fondling your package, causing you to moan in pleasure. Though it still hurt a bit, the pleasure overrode the still lingering pain in your nuts and kicked your head back to Elaina’s amusement.

“Hmmmm, looks like I’m doing such a good job at taming this monster that I might gain a level after this fight.” She mused as she continued to stroke your shaft with progressive vigor. As cheesy as her double entendres were, you found them oddly arousing, probably because you do a lot of gaming on the side apart for your usual schedule. On top of that, because she had experience with her husband and she’s also a gamer, the whole scene felt like heaven.

“I guess it’s time to activate my limit breaker.” The moment she said that, she began to deepthroat your entire schlong in a slow and sensual manner. You felt immense pleasure from feeling the back of her throat with your shaft while she also massaged your pills. You wanted to give her presumably wet vagina some pleasure but you knew she wouldn’t have any of that. As you looked around, you noticed your foot is within striking distance of her puffy vulva. Smirking a mischievous grin, you used the toes of your right foot and pulled aside the crotch of her panties, soaking wet from her hungry pussy. You rubbed and rubbed your big toe across the length of her folds, causing her to shudder and moan with your cock still in her mouth.

“Oh yeah, baby!” She said, briefly removing your cock. “Keep pleasing the water goddess and you’ll receive her blessing!” More of that gamer talk integrated with her intercourse, she was one sly and hungry minx. It must’ve been months since she had someone rock her world. Resuming her blowing, you upped the tempo of footing her sopping wet vagina. The moans she made vibrated along your length, pushing you closer to your inevitable climax and hers as well. With your blood basically being replaced by pure testosterone at that point, you decided to maneuver your big toe into her wet lower lips. With each insertion, Elaina moaned and gasped with desperation and abandon

“Oh my goodness, my mana is low!” Elaina moaned out as you felt her walls clamp around your big toe, upping the tempo of her blowjob as she orgasmed. You couldn’t withstand it any longer and you busted your load down her gullet. You held onto her head for dear life as you shot loads of ropes of you continued to cum.

“The goddess… of.. the... water temple… is pleased!” Elaina panted as she rolled onto her back next to you on the bed. “Your battle prowess is to be commended.”

“Well then, I do declare myself blessed.” As you said those words, Elaina gets off the bed and stops at the end of it. Those bedroom eyes she gave you… enchanting, mesmerizing, and intoxicating.

“Now, the water goddess shall give you a reward that few mortals dream of.” She then began the most erotic dance you ever saw. It was a mix between what strippers would do at a club and the most erotic belly dance. Her hips gyrated in a hypnotic way as she fondled her E-Cup mounds. Then, she began to slowly hook her fingers on the hem of her tank-top. As she pulled up her top you then got a glimpse at her perky chest pillows, covered by a red bra.

“I see the wayward adventurer enjoys the view.” She said as she raised her arms in the air and began to shake her hips as her skirt started to become loose, falling down and revealing her pantie covered flower. “You have the rare privilege of having a personal audience with a goddess.” Elaina reached her hands behind her back. You heard an audible click and you knew what that meant. She allowed gravity do the rest as you saw her breasts unveiled, puffy nipples and all.

“I know you like what you see, adventurer.” Elaina moaned as she took her tits in hand and massaged them, shaking the pair up and down. There, you’ve felt your loins beginning to tighten as your member became hard once more. Elaina immediately took notice and gently blew on your spear, sending shivers of pleasure down your spine. It was very erotic and sensual to the touch. You reached forward to grab hold of her soft titflesh, only to haf your hand swatted away by hers. “The adventurer should wait for permission to touch the water goddess.”

Hooking her fingers around the hem of her sex-soaked panties, she continued her erotic dance as she slowly but surely slid them off. Just as Elaina was about to reveal her slightly hairy beaver, she crouched down and pulled them back up. For a tease, you found that rather sexy. Your cock tingled with unprecedented lust and want as you want to net another MILF like her to your high score as you call it. Finally, she does away with her panties and tosses them to the side. Her eyes became half-lidded and a lustful smile develops on her face.

“Holy mother fuck, this is intense.” You gasped as she climbed onto the bed like a cat on the prowl, lightly brushing her boobs against your cock. When her eyes met yours, she pulled you in for an open-mouth kiss. It certainly felt weird having sex with one of your friends mothers. But, you being Dr. MILFlove, you couldn’t care less as Elaina broke the kiss. To further tease you, she ground her puffy pussy against your shaft, leaving trails of her warm juices on your length. She continued to do so until the tip of your spear made contact with her lips. However, she just continues to grind her vulva against your tip, further driving you insane as everytime she puts the tip in, she takes it out and grinds it once more.

“I think it’s time for the adventurer to receive his reward.” Elaina moaned as she stopped her grinding. “Now… You may enter the water temple and lay with the water goddess.” She then speared herself on your cock, swallowing your shaft in her love canal. She blushed, you blushed as she brought her mouth to your ear. “Your legend precedes you, Dr. MILFlove.”

Before you could think about her earlier remark, Elaina’s lips made contact with yours as her hips moved her vagina up and down your length. The feeling of her breasts against her chest, her tongue wrestling with yours and her pussy humping your cock, it all indeed felt like a gift from a goddess… a very sexy gamer goddess. The both of you had fuck for about an hour before the inevitable outcome came around.

“I… can feel that… you’re about… to cum!” Elaina said as she took your hands in hers locking both your fingers together, humping with complete abandon. “Go on, unleash your life force into my caves and let it flow!” Even at the doorsteps of her climax, she still kept up with fantasy. You gotta hand it to her being able to think clearly with all of those endorphins flooding her brain. Just as her walls were about to clamp down on your rod, Elaina pulls sits you up and embraces you. She lets out a hoarse moan when her walls lock around your cock and squirts rivers of ladycum allover your crotch, making your shaft quiver and shoot torrents of semen into her womb and making her stomach slightly bulge. After respective orgasms lost their momentum, the both of you collapsed on the bed next to each other.

“Oh wow!” Elaina gasped. “That certainly cured my itch.”

“Glad to be of service, Elaina.” You replied as you climbed on top of her to make out with her furiously. In the midst of your kiss, you heard the faint sound of your phone vibrating. Pulling it out of your pocket, you saw another text from Button.

“Dude, just fixed Rumble’s machine. Will be there in about 20 mins. CYT.”

“Oh shit!” You muttered to which Elaina heard. “Button will be over within 20 minutes!”

“No worries, we’ll take short showers and I can phone in the pizza.” Elaina said as she got off the bed and directed you to her shower room. “You can go first. It’s the least I can thank you for… servicing me.” Giving her a quick wink, you jumped into the hot shower, and began cleansing every trace of your deed from your body, taking extra care to not give your friend any hints of what you did. You could only imagine how awkward the air would be if Button Mash found out that you banged his mom. All in all, you’ve had sex and it was time to play games and scarf down pizza.

“Heh, Time for Dr. MILFlove to relax and play.”


Author's Note

Warning: The Surgeon General has determined that this chapter will contain cheesy video game double entendres.

Anyways, I'm glad y'all like this so far. Show of hands, who wants Milky Way in this story? Ask and ye shall receive.

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