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

It was another day Crystal Prep and another day of staying after school for a swim team meeting. You got pressured into joining by your overbearing parents to help you be more outgoing. But, you knew the true reason they made that move for you. They were afraid that you’ll get hooked on doing hardcore drugs, barring the fact that you’ve never had nor will entertain such thoughts. But, you being you, you rolled with the punches to see where it would take you. As you spent more time with the team, your physique started to improve and you lost quite a lot of extra fat. Over time, the girls at Crystal Prep took notice of you, sometimes gawking at your build. You weren’t incredibly muscular but handsome enough to where you could have a good chance with the ladies.

As you and the swim team wrapped up the day’s practice for the upcoming games, you sat at the bleachers while you saw the rest of your teammates leave. Ignacio, one of your friends on the team walked over to you with a quizzed look on his face.

“Yo Calculus, why are you staying behind?” Ignacio asked “Everyone else is leaving.”

“I’m just catching my breath.” You said with an exhausted look.

“Well, hurry up if you don’t wanna get locked in and Dean Cadence is going to do her door locking rounds soon.”

“Ok, I’m going to be taking a shower here though. I much rather not have my car smell like a dirty gym sock.”

“Well ok, but be quick about it. If Cadence catches you here this late, both she and Cinch will tan your hide.”

“Don’t worry about that. I can deal with them.”

After your friend walked out the doors, you breathed a sigh of relief. Your last statement, however, was a half-truth. While you didn’t fear their anger, their impending call to your parents made you quake. If there was one group of people you didn’t want to anger, it was your parents and they can get rather angry if you stepped out of line. However, Ignacio’s mentioning of Cadence eliminated your worries to an extent.

As you stripped naked and hopped into the shower, your thoughts drifted to that of one of the women of Crystal Prep you had the hots for: Dean Cadence. While young, compared to the other staff members, her commanding position is betrayed by her sheer beauty. Cute face, gorgeous eyes, stylish hair, perfect figure and luscious hips make her the subject of a lot of your fantasies. Sadly, she got married to Shining Armor a few years ago and they recently had a kid. While your chances with her are nil, erotic thoughts about her still danced in your dreams. Even just a mere mental image of her in work clothes is enough to make your dick stand at attention.

As you thought more and more about Cadence, you felt a certain area of your crotch tightening up. You looked down and noticed that your shaft became rock hard from just a thought alone.

“Aw fuck,” you muttered. “Might as well then.” Contemplating a solution, you decide that since the flowing water was going to keep you clean as you whack off, there wasn’t anything keeping you from a quick masturbation session. Double checking for anyone nearby, you waste no time in grabbing your dick with a single hand.

“Here goes nothing.”

Slowly, you stroke your dick as images of the ever-so-sexy Cadence invade your conscious, images of her naked, busty form. Fantasies of you and her doing the spoons position only furthered your arousal as you quickened the pace of your strokes. You eventually found yourself lost in your own pleasure and the hot streams of water only served to magnify the effect. Little did you know, the moment was soon about to turn awkward in a big way.

In the midst of your self stimulation, you failed to notice the soft sounds of footsteps on approach. It was truly amazing how a showerhead could be a pseudo sound muffling device from its squeaking noise. At one point, you swore that you’ve heard a voice sounding off but you weren’t sure what it was. Then, at the corner of your eye, you saw a pink hand grab the shower curtains.

“Hey, whoever’s in here, what are you doing here at this time? It’s supposed to be clo-”

Just then, the shower curtains were pulled aside by the subject of your masturbation session. Dean Cadence just stood there as you held your erect shaft in your hand, staring at you in shocked embarrassment.

“Well… this sure is awkward.” You said in your mind. Awkward doesn’t even come close to describing what the situation felt like. There you were, in the showers, making eye contact with the school’s dean with your dick in your hand. Your instinct badly wanted you to freak out like a jumpy person watching Stephen King’s IT late at night. Your rational side, however, dictated that you’re to stay calm. Still gripping your pride, you worked up the courage to break the awkward silence.

“Ummmm… Can I help you, Mrs. Cadence?”

Her face registered all levels of embarrassment as her face blushed a deep red color. With her hands covering her mouth, all you could see was her eyes and they seemed to paint her mood quite well.

“I-I-I-uhhhhh… So sorry to bother you, s-student.” As quickly as she spoke her words, she dashed away from the sight of you showering. For the next minute, your mind processed a wide range of scenarios that would happen next. Would she just run off and the next run in be awkward? Would she call the police and the both of you face serious charges? Expulsion? Each mental visualization of different possibilities only served to heighten your already rapid heart rate. All you wanted to do was to try to de-escalate the already precarious situation.

Wrapping the towel around your waist, you walked out of the shower and began searching for the spooked Cadence. You eventually found her sitting on one of the benches near another row of lockers. You heard what could be quiet gasps as you approached her from behind, curious as to what she’s up to.

“Hey, Mrs. Cadence?” You called to her with no response. “I-I would like to apologize for what you saw me doing back there.”

…

“I could explain what you witnessed me doing.”

…

“Mrs. Cadence, are you ok?”

“I’m… I’m fine, student. What were you doing here past closing?”

“Bathing after swim team practice. I don’t like my car smelling like a gym bag.” You knew that she thinks you weren’t telling the complete story. She saw you beating your meat in the showers and she probably knew you were. But, she didn’t know that she was the one you jacked off to.

“Well, you should know better than to stay on campus after closing.” She said, standing up with her back still turned to you. “You are in some deep trouble for that. W-We *gasp* ssshall discuss this *gasp* next week with Ms. Cinch.”

You paid no attention to her words. All you could focus on was the fact that she was gasping with every other word she uttered. With careful observation, you noticed that her arms appeared to be centered towards the front of her waist and only her right arm was making slight movements. You began to put two and two together: her gasps, hands presumably centered towards her crotch, and only one of her arms were moving. You had a good idea of what she was doing but you needed visual proof to confirm it.

“Ok, what are you doing, Mrs. Cadence?” Your words appeared to have made her jump in surprise, like a reaction towards something she was hiding about to be discovered.

“N-N-nothing! Never mind! Mind your own business, student!” You didn’t buy it. She was clearly up to something and you knew it. Walking closer to her, you quickly grabbed her right arm. She struggled to break free of your grip but your inquisitive attitude only made you all the more determined. As you finally grabbed hold of her wrist, to much of her objections, you saw a coating of moisture on her fingers. You took a quick whiff and found the liquid to be musky and… oddly arousing. Snapping back to reality, your earlier suspicions have now been confirmed.

“Mrs. Cadence, ” You gasped in shock. “Y-Y-You were schlicking, weren’t you?!” You knew it, you fucking knew it! Though, you did see it coming after she caught you in mid-masturbation. She was aroused by the size of your member, but, she was a married woman. Why did she suddenly run off just to fingerbang herself to you being buck nude? Why didn’t she immediately close the curtains or never opening them to begin with? At that point, you had a lot of questions and no answers to them. Still gripping her wrist, you start to pull her closer, causing her to try to get away.

“Let go now! I’m warning you, student! You’re on the thinnest of ice here!” She screamed as you started pulling her back towards you.

“No! We’re going to talk about this! I’m not letting you go until I get an explanation!”

“You’re not the one to talk! I saw you with your… thing in your hand!”

“Well, then why were you staring at me for that long when you shouldn’t have opened the curtains?”

As she pulled away again, you responded in kind. However, it was the spark that had finally set off the powder keg the situation was. Her high heel shoes weren’t slip resistant and she slipped and fell on top of you, knocking you to the floor like a wooden domino. With a loud thud, you winced at the pain of your hand being bashed between the tile floor and your hard skull. The good thing was that your head didn’t suffer anything other than a minor bump.

However, Dean Cadence laid on top of you, her beautiful mounds squeezing against your chest and her lips locked with yours. Immediately after you both opened your eyes, Cadence had hastily broke the kiss in embarrassment, not that you didn’t mind the accidental gesture. The atmosphere felt incredibly weird and erotic at the same as your now unveiled member tightly pressed against Cadence’s clothed nether lips. A tingling sensation ran down your spine as you tried to process the situation, looking into her blank stare.

Without warning, Cadence suddenly resumes the accidental kiss. It felt different that time, like it had a deeper meaning and purpose behind it, similar to how a lover would give one. Becoming more relaxed from the sensation, you closed your eyes and allowed yourself to become lost in the kiss, resting your hands on the back of her head and her nicely firm yet soft rump. As the kiss went on, your shaft got harder and harder, causing Mrs. Cadence to let out a soft moan breaking the kiss.

“Mrs. Cadence, why?” You asked in slight shock, still reeling from the earlier experience.

“Just seeing sight of you like that made me wet. I never expected you to be that… gifted.” She replied, referring to your dick. Admittedly, you felt flattered that one of the hottest women in school complimented your lower anatomy. Still, part of you felt that it felt wrong because she is a married woman and the potential fallout would be painful.

“But, you’re a married woman, to Shining Armor no less!” Holding your face in her hands and caressing it with her thumbs, Cadence gave you those half-lidded ‘bedroom’ eyes.

“No need to worry about it.”

“What?!” You gasped in surprise.

“Me and him are in an open marriage. He said that it’s fine for the both of us to have sex with whoever we want as long as it doesn’t result in pregnancy.”

“Hmmm, that sounds… reasonable.”

“Oh, it is, Mr…”

“Calculus.” As you gave your name to her, Cadence stood up and put her hands on her damp coat. You anticipated what she was going to do next but not how arousing it’ll be. The sensation ate away at your mental fortitude, making your anxiety grow stronger. You badly wanted to strip her naked and spoon her. But, you decide to go along with what she has planned for you.

“Ok Calculus, I have a couple of questions before I go any further: How old are you and are you a senior?”

“Yes, I’m 18 and graduating this year.” You softly said.

“Who were you jerking to in the shower?” Damn, she got you there with the question you were ashamed of answering truthfully. But then again, due to the predicament you’re in, it didn’t really matter. It was more of those scenarios of admitting to a crush that you love her deeply. With one big gulp, you swallowed your pride and decided to tell the truth.

“Y-Y-Y-You, Mrs. Cadence.” With your admission, Cadence gave a rather mischievous smirk as you closed your eyes and braced for the worst. However, after several seconds, you opened your eyes to a sight that you’ll never forget.

Cadence stood before you, completely nude. Her D-cup breasts jiggle as she swayed her rack, side to side. There were no signs of a bush near her nether region, a truly wonderful sight of the Dean. There, Cadence gave you a smile that could only be known as the bedroom smirk.

“Okay Calculus,” Cadence started. “ I'll make you a deal. Get me to cum first and I'll let whatever fantasy you have about me come true.” She said it, she was going to make your dreams. You were going to spoon her but you have to fight for that pleasure.

Without warning, Cadence straddled your face with her puffy pink vulva level to your mouth. It was dripping wet with the same fluid you found on her hands. Like before, the scent was musky and arousing.

“Just the sight of your package is making me wet down there.” Cadence moaned as she brought her mouth close to your shaft. The subtle breaths from her sent shivers of ecstasy through your spine as she brought her mouth closer and closer to your pride. “Please, don't disappoint me.”

As you brought your mouth closer to her pussy, you felt a wet and squishy sensation snaking around your rod as Cadence gives it a lick. The spine-tingling sensation of sensual pleasure was only magnified by her taking your the length of your dick into her mouth, bobbing her head up and down. To say that it felt good would be underselling how it felt. It felt like getting blown by a goddess. In that moment, you remarked in your head that Coach Shining Armor was truly lucky for getting a wonderful woman like Cadence. Getting those thoughts out of your head, you divert your focus to licking her vagina.

Once your tongue made contact, you heard what sounded like muffled moans from her as your tongue began its assault upon her nether lips. From how wet she’s becoming from your licks, she was enjoying this as much as you were. Despite the smell being musky, the wetness tasted like the perfect ratio of salty and sweet. You were determined to taste more of it. YOU were determined to make her orgasm first.

While you were licking her lower lips, your tongue brushed over a small nub that made her quiver. Pulling your tongue away for a brief moment, you realized you hit her clitoris, her achilles heel. With her muffled moans fueling your drive, you continued to ravage her clit with your tongue, flicking it, brushing it, and even rubbing it between your teeth. With each maneuver, you felt Cadence quiver and writhe with pure bliss. Little did you know, she was planning her endgame. In the midst of her pleasuring your knob, she landed a firm but soft grip on your balls, massaging them as she continued to suck on your shaft. The sensation was powerful, briefly stopping your assault. You were, in no way, going to let her get away with it. Thinking hard and fast, you devised of a plan to rock her world. In a heartbeat, you jammed her tongue in her moist love tunnel.

*Gasp* “OH… MY GOODNESS!” Cadence gasped as she was overwhelmed by the feeling of your tongue in her pussy, momentarily removing her mouth from your penis. With that, you had a brief moment of respite but you were sure she was going to recover from the surprise pretty soon. You wasted no time in resuming your tongue’s intrusion into her vulva. She was still recovering but you planned on keeping the momentum and then some. You used two fingers to scout around for her clit and rubbed it between them. She let out long and loud gasps and cries of pleasure as you ravaged her on two fronts.

It wasn’t long before she let out one final scream of orgasmic bliss as she came, drenching your face in her ladycum. You felt her inner walls grip tightly around your tongue as her orgasm went on. You held her lower lips to your face as she continued to become lost in her release, taking in more of her sweet ladycum. After a minute of intense pleasure, her orgasm died down, rolling off of you and on to her back, panting in slight exhaustion.

“That… was amazing, student.” Cadence panted as she sat against the lockers with you. “You should know that I’m a woman of my word. You made me cum first so I’ll be willing to make your fantasy come true. What is it you want to do?” It didn’t take long for you think on that end. Your earlier masturbation session made you think of a most sensual fantasy about her. Wasting not a second more, you blurted out your answer.

“I’ve always wanted to spoon with you, Mrs. Cadence!” Your words were met with a loving smile from her and a peck on your lips. As she stared you in the eyes, she held your chin with her index finger.

“Please, just call me Cadence. You deserve that privilege.” With those words, she turned her back towards you and laid on her side, lifting a leg up. “Now come, take your prize. You also don’t need to worry about getting me pregnant; I’m on the pill.” Gulping at the realization that this was the moment you’ll lose your virginity, you wasted no time in getting behind her and wrapping one arm around her midsection and guiding your shaft to her vulva with the other. Once you felt that feeling of her wet lower lips on your tip, you took the guiding hand and held her raised leg with it, pushing your lap howitzer into her vagina. It was an all new feeling to you. You were finally having sex with the woman of your dreams, the dean of CPA no less. Her love tunnel was gripping your member tightly as its warm and wet feeling sent new levels of pleasure throughout your nerves.

“So, how do you like it?” Cadence moaned with a sultry tone.

“I-I-It feels… magnificent.” You stuttered back, still in shock.

“Congratulations, consider yourself a virgin no more.” Catching you by surprise, she plants another kiss on your lips. However, it was fueled by pure lust than the earlier ons from just the spur of the moment, it was pure unbridled passion. Fueled by lust and confidence, you began to thrust in and out of her pussy, earning muffled moans from her as she kept the kiss with you.

“Calculus, please! Harder! Faster! Deeper!” Oh that naughty Dean of yours, talking dirty to you only added fuel to the fire that was your passion. Obliging her request, you redoubled your efforts and did what she begged of you. As your dick reached further and further into her love canal, you were stopped by a fleshy wall. From your time in biology, it didn't take you any thought to figure out that you reached the entrance of her cervix. Each and every time your tip rammed against it, Cadence would let out an excited Yelp as her inner walls gripped tightly around your member, as her climax was near and yours was soon to follow.

“C-Calculus,” Cadence with a pleasured stutter. “ I'm… about to cum!” It also didn't take that long for you to reach that level of buildup in your loins.

“Me too!” You grunted as you upped the tempo of your thrusts. “Let's cum together!” Letting go of her leg, you wrap your other arm around her chest as you held her tightly against you. With a few more hard thrusts, your dick quivered and throbbed as you released your seed into her womb. Spurt after spurt, your seed filled her insides as her walls tighten around your member with her own orgasm, milking you for every drop you had in your loins. As both of your respective orgasms died down, you held Cadence against you, not pulling out yet as you brush her face with yours while engaging in post coital cuddling.

“That was wonderful.” Cadence said as she got up from the floor, breaking the spooning embrace. “How did you last that long?”

“Dunno, I guess it was from training my stamina while on the swim team.” You replied with a shrug, getting up as well and reaching for your spare clothes.

“For your first time, you did good.” Cadence complemented. “With that level of stamina, you can have a line of ladies wanting to do you.” Truth be told, you were approached by quite a few of the girls in the school, sometimes with them doing the flirting whistle sound. But, your busy and structured schedule prevented you from reciprocating those advances.

“Well, I tend to go with the flow when in that regard. If it happens, it happens.” After you got your spare clothes on, you noticed Cadence putting her still slightly damp attire on as well. “Anyways, I have to get going. My parents like to freak whenever I'm out for a long time.”

“Don't worry about me, Calculus.” Cadence giggled as she put her coat back on. “I still have part of my rounds to do. I'll see you next week. Take care!”

“You too, Cadence.”

As you traveled towards your house in your Camaro, you reflected on what happened earlier: you lost your virginity and you realized you fantasy with the woman you had the hots for. You considered it to be not only the best day of the week but also of your high school career. You drive on down the road in satisfaction as you feel proud of yourself.

Little did you know… you lit the match in the metaphorical room of gasoline and the flames are about to burn you.