Culdesac Kelly Next Door Whore Ch 06 Nerd Milf

Well, Wendy Fernstein was coming along just fine.

At the moment this little 36D wide-assed 18 year-old blonde was on top of me, my cock deep in her pussy as she rode me reverse cowgirl style.

"Higher, higher, that's it, now slowly down...". She obeyed my commands, lifting her pussy off of my cock inch by inch, until it was almost out and then slowly sliding back down until her sweet jiggly ass was resting on my pelvis.

"Fuuuuccckkk...it's hard not to just piston fuck your fat dick....", Wendy complained. She then looked over her shoulder and bit her lip, pleading with a whiney little voice I had taught her to use, "I just want to grind my whole pussy into you Daddy...." I chuckled and gave her ass a smack, "Oh no you don't! this is training. Slut training. And you gotta fuck like I tell you. You can cum on your own time, if you follow all your lessons. Now lift that ass again, there ya go...." I fondled her jiggling ass cheeks as she lifted and lowered her pussy up and down my shaft. Her white ass flesh felt amazing in my hands, and I could not get enough of those round globes. In fact..."

"Now come off my dick and scooch backwards, farther, farther....yeah!" She had her ass in my face and I buried my tongue straight up her asshole and pushed her cheeks even tighter towards me, suffocating myself in that ass. I could hear her giggle and shriek as I probed and licked and nuzzled her sweet little sphincter

all I could, until finally I pushed her off, gasping for air. I then flipped her over and began to fuck her just for myself, missionary style, pounding into her pussy just like she had been begging me too.

"Oh, YES!! Please, Vernon! Fuck me hard, fuck my pussy hard!!"

Her pink laced canopied bed rattled and shook with every thrust. This was the first time I had fucked Wendy in her house and I was a little nervous about getting caught. After all, I was running a small time prostitution ring in the suburbs, and I had to be careful.

Jesus, it was hard not to giggle every time I thought something like that. But it was true. The details are in the previous chapters, but essentially I have arranged for my friend Kelly to whore herself out to our neighbors. Wendy Fernstein is the 18 year-old dumb-as rocks daughter of computer software engineers that found out about our gig, and now I fuck her on a regular basis, teaching her how to fuck for a husband. She occasionally does a little sex work for me, but just a little, as she doesn't really have the stomach for the gig. So right now, as I pin her arms down and slam my cock into her, I am just fucking for fun.

"Ungh, yes, fill me with your cock...fill me with it, make me take it!!!!" Her filthy grown-up language contrasted bizarrely with her childhood bedroom. The boyband posters, frilly curtains, the stuffed animals, and then a sweaty 18-year old body getting fucked like a Hustler Honey. "Oooooh....yes!! I love feeling those fucking balls bounce against me...fuckfuckfuck!!!", Wendy screamed.

Out of the corner of my eye I thought I saw a flicker of a shadow pass by the slightly open door. But I was strokes away from coming, and wouldn't stop now for anything. I let go of her arms, and her hands flew to my ass, pulling me closer and deeper into her, her legs twisting around me, grasping me to her with her entire body. Thrust after thrust made us both grunt and moan. My cock erupted with sperm, forcing me to shout out and growl with the pleasure of release. For minutes, my cock throbbed and pulsated with the orgasm as we both lay there, locked in congress and catching our breaths. When I finally pulled out, rose from the bed, disposed of the condom and started to look for my pants, Wendy had fallen to sleep. So I used her shower, dressed and walked out of her room, only to walk smack dab into Wendy's Mom, Dr. Amalia Fernstein.

She was kinda short and had long dirt brown hair which she had carelessly tied back in with a black hairband. She had thick glasses, a prominent nose and the same wide mouth and sensuous lips as her daughter. Her chin was pointier and her demeanor was far more serious than her bubbly daughter. She was dressed in a long light blue dress a with a cardigan that buttoned all the way up....well, shit, I guess I'm describing a nerd. A typical nerd. I didn't want to admit it, as I hate stereotypes, but it seems the word keeps throwing itself at me. She was curvier than the classic skinny nerd stereotype, but with her dumpy and all-covering clothes, one could not detect much else about her figure.

At the moment, all I was really concerned about is whether or not she was going to shoot me in the face for having sex with her daughter.

Her hard green eyes were boring into mine. It was all I could do to keep my cool. I retreated into the Vernon Mangripp character, that Pimp guy who was miles away from the real John Parsons. Vernon wouldn't let a little white Nerd-ette back him down, even if he had just fucked the shit out her daughter. Yeah, that's right little Mama, what you looking at? Three, four, then five seconds passed in silence between us. Then she sniffed a little sigh.

"Follow me, if you would."

She walked away toward the back of the house.

The fuck?

I followed.

She was in a back bedroom, sitting on the reason the room was named such. I didn't know Dr. Fernstein very well, regardless she seemed a bit perplexed, and not angry at all.

"Firstly, my name is Dr. Amy Fernstein. Who are you?" Her tone was flat, almost monotone.

"Vernon Mangripp."

She blinked. "Doubtful. But I can acquiesce to the need for pseudonyms in your line of work, which I assume is prostitution." She stopped right there, making it clear I needed to answer.

"And if it was?"

"Well. Ahem. I would like to hire you."

I blinked. I breathed. I thanked Viola Spolin for my Improv training.

"I see. Are seeking to hire my girl, Miss Mandy?"

"Oh, my goodness. No. I would like to hire you to do to me what you just did to my daughter."

"I see." Holy shit. Really? Really?? I walked across the room, and then turned back. "Are you fully aware of all I just did to your daughter?"

Dr. Fernstein's brow furrowed. "Ah. No. I discovered you and Wendy, in the middle of it, as I can perceive such things. So, I am not fully aware of all the things you did to her." She fidgeted a little, betraying some cracks in her calm demeanor. "It was more the results I am seeking you to...reproduce."

"Ah, that's good. That's clear. And that's something I can't guaranty. The orgasm, that is. I don't know everything about sex, or women. I only know what I know. And it's not like men. Mandy and Wen...ah, well..."

"That's alright Mr. Mangripp. I know my daughter is a wanton slut. I've made my peace with it, though her father hasn't. If she was intelligent it would be a shame. She isn't, and she seems to be preparing her self for a life of what is, basically, sexual indentureship, at her own choice."

I blinked. "Okay. So, men cum easy. Women don't. With women, you can have all the right stuff, and still not make her cum. So...."

"I am aware of the research, both academic and personal. And indeed, I have had only self-served orgasms for years. But, from what I witnessed...". Amy licked her lips and her hands gripped the sheets on the bed. "...I believe with some coaching, and with the added comfort of the the financial nature of the exchange, which would ameliorate the ethical and moral dilemma, we can achieve success. If not, I will accept the results and not ask for renumeration."

I paced the room slowly and then with my back to her I said, "It's two-fifty for an hour, and that includes oral, mouth to mouth kissing, and anal. I won't draw blood or do golden showers." That last line was one Mandy used all the time. I didn't think she would want any of that. I just thought it sounded cool.

"No, neither of those for me. Not yet at any rate. Let's just try to get me to an orgasm and go from there. You have a deal." She stood and walked over to me with her hand extended. I took her hand and shook it, like we had just sold a house or something. About ten seconds ticked by with nothing happening but two grown adults standing in front of each other on silence. Dr. Fernstein finally broke the silence.

"Is this a time where it would be appropriate to fellate you now?", she asked blandly.

"Wow. You really have no idea what to do, do you?"

"Other than the basics for procreation. It never really came up. It is only recently, having witnessed my daughter's adventures, that a need for non-procreative activities has existed in me at all."

"Hm. That helps a lot, actually. But let's get Wendy out of the house, and then we can be comfortable and alone. May I call you Amalia?"

"No. I would not care for that. I think calling me 'Doctor F' will be just fine, in consideration of our activities. Wait here please."

Dr F left the room and came back in just a few minutes.

"I gave her 315 dollars and sent her to the mall. That is one nice thing about having a daughter with shallow values. They are very easy to distract. Now, may I see your penis?"

I almost coughed. "I'd like the 250 first, please. A rule of the profession."

"Of course. Here." She reached into a pocket of her dress and pulled out a wad of cash and handed it to me. After counting it to confirm the amount, I tucked it away and unzipped my pants. I pulled out my flaccid cock. Amalia peered at it.

"Can you get it harder, like it was before, please?"

"Perhaps if you took off your shirt, or your skirt, that might help me."

"All right, you're the professional." Amalia unbuttoned her shirt to reveal a very utilitarian bra, off-white and ancient. Her skirt, however dropped to reveal a killer ass and thick thighs that made my mouth water. And she was a grown-up, an actual grown-up! Her body had some age, some life, some experience. She had the body of a fucking adult, and that was so hot after only sleeping with the 18 year old Wendy. Maybe it was just a case of the grass being greener, but as Dr F stripped down her MILF-y curves were making my cock twitch in response, a twitching she noticed.

"Oh, I see your penis is getting harder. Should I touch it now?"

"Dr F, you're the client. You should do whatever you need, or want to do."

"It has been a long time since I've touched another penis. I think I'll do that."

"Great. Where would you like me to be?"

"I'll sit on the bed, and you stand before me, yes...right there. Oh my, it is getting bigger. I wasn't sure if I saw an accurate view of it while you were fornicating with my daughter... it is a pleasant.. specimen..."

She was stroking my cock with both hands now, caressing it, with her fingers and her palms. She squeezed it several time, and stroked it harder, using her hand on the very tip, which brought a gasp from my lips.

"If I did not fellate you, would you be disappointed?"

"It is impossible to disappoint me."

She looked surprised and a little lost.

"Here, let's try a few things." I kneeled down in front of her. "Tell me if any of these things I am going to do to feels good." I ran my hands lightly over her thighs and waist, taking my time, paying strict attention to every curve my eager fingers brushed across.

"That is not unpleasant. Is it meant to be orgasmic?"

"No, this is meant to make you feel relaxed and beautiful, so you get to the Orgasmic part."

"I see. Squeeze my thighs harder, please."

I began to kneed her thighs, increasing the intensity squeeze by squeeze. She didn't stop me, in fact she began to breath a little faster, and her face grew a little red.

"I'm going to go a little ...harder..now. If I go too far, say the word 'Calculus' and I will stop."

"Ah, the safe word rule as used in Bondage and Discipline and Sado-Masochistic sexual activity. Is this considered to be Bondage and Discipline and Sado Masochistic sexual activity?"

"Well, it might be....", I leaned down and kissed her thighs, and then gently took her skin between my teeth.

"Oh, oh my...." Dr F said, her voice finally breaking from it's usual clinical delivery. I began to bite down lightly, gently increasing the pressure second by second. I felt her gasp and wiggle a bit, but she said nothing. My teeth sank deeper into her flesh, deeper and deeper until she peeped out with a throaty, "Calculus! Calculus...oh my..."

I sat up, licking my lips and looked her dead in her eyes. "Did you like that? Did you like what my teeth were doing to you?"

"I...I...partly. I would not wish for you to break the skin...but the feeling was....oh my..." A slight smile flickered at the corners of her mouth.

"Let's try this..." I stood up and lifted her to her feet, and guided her to the bed, and positioned her in a doggy style position. I took my time, touching and caressing her more than necessary. "Tell me, Dr F, did it bother you that I put you in this position, that I made you get on the bed, with your ass up in the air."

"It did not disturb me, I cannot say that I enjoyed it, really."

"That's a start." I was kneeling by her side as I started to rub her ass cheeks, softly at first, but increasing tempo and pressure gradually. Her pale skin reddened up nicely. As soon as her milky white MILF ass cheeks gained the appropriate level of pink...

"Dr F, do you remember your safe word?"

"Of course I do, why do you.... Oh!"

My hand had slapped down briskly on her ass cheek. Her white buttock rippled wonderfully from the blow, and I applied an equal stroke on the other cheek right away."

S-PAAP!

"Ohhh MY!" Dr F said again, her body trembling slightly.

S-PAAAP-PAAP!! My hand came down harder on her ass cheek, and then quickly on the other, making her hips wiggle back and forth.

"Oh my goodness, that is a...that is a ...", I let Dr F search for words to describe her feelings, and leaned down to whisper in her ear.

"Shush. I'm going to spank your ass now, because I think your sweet ass needs to to feel my hands on it." As I poured words with my husky voice into her ear, my hands were running themselves all over her back and ass. She began to arch her back a little, like a cat.

"Um...Ah, well, I do feel that...um..."

I sat back up and gave her six hard whacks, three on each cheek, filling the bedroom with the echos of the contact my huge hands made on her jiggly ass.

"OH GOD!" She screamed, and then gulped hard as she tried to contain her lust. "Yes! Yes, I am enjoying your spanking." Her voice had retreated to the clinical Doctor's tone, so I matched it.

"Ah thank you. Now, tell me, at this juncture, would you find it more stimulating to demand to be spanked, or for me to spank you to please myself, perhaps adding a fantasy of resistance?"

"...oh, that's something that I...oh....",her professional tone broke a little more and I swear I could hear her pussy getting wetter as she thought about the two options. " I think I would like to demand to be spanked.", she said in a monotone that was also somehow sexy.

"Excellent. Now, we need a motivating force behind your demand that I can respond to. And this force must be channelled through the subjective lens of your personality." Okay, I was pulling all that shit out of my Community College psych class, but I think I was remembering it right...?

She rolled over on her back to look up at me, hissed at the twinge of pain on her ass, smiled at the twinge, and then she blurted out the thought that made her roll over in the first place. "An example, please."

"Oh, ah...such as, 'I've been a bad girl, I deserve a spanking, Daddy.'"

"No. I don't like that. May I degrade and insult you as part of this?"

I didn't blink. "Yes, you may. Um, but don't hit my balls."

"Hm, I see. I understand." She rolled back over and stuck her glowing pink ass in the air. "Spank my ass like the slavish worm you are, please."

I did as she commanded. S-PAAP! S-PAAAP! S-PAAAP!!

"Oh my, yes, now spank it harder, little man, please."

SMAACK! SMAAAACK! SMAACK!

"Oh my,MY! I like that! I like...telling you...what to do..." She was stumbling over the thoughts, but she was making sense. I leaned over and whispered in her ear. "Then tell me, order me. And Don't...say...please....", that last part made her take a deep breath as she lowered her head slowly to the mattress, her face out to the side, and stuck her ass higher into the air.

"Spank my ass, spank it harder...." I felt her almost say please, and then she said, "...NOW."

I did as commanded, shifting from Dom to Sub in two minutes. I gave her ass the same level of pounding, changing nothing this time, but staying consistent. I was teaching her how to order me to fuck her, but she was a quick student. She began to tell me what she wanted right away.

"Harder! Harder! Now slower, take your time....three seconds between each stroke. Unnh....unh.... unnnh....! Now give me lighter strokes but faster! Yes, good... Ohhhhhhhh my goodnesss......"

"Dr F, would you like me to touch your vagina, or your rectum in any way?" I asked casually.

"Oh, oh my yes, that's right. We can do things with that as well. I had forgotten."

"You can order me to do anything." I said slowly and dramatically. "And you have to order me. I want you to."

Dr F rolled over onto her back in a flash, and winced as her ass cheeks touched the bed. "Fuck me, Vernon. Put your penis in me."

"How far do you want me to put it into you?" I asked while climbing between her legs.

"Start slow, I'll tell you when to stop." It was getting easier and easier for Dr. F to give me commands, and her voice began to gain a hint of steel in it. "I want to put it in." She reached down and grabbed my cock and guided to her hairy bush which was dewy with her wetness.

Dewy with her wetness? Yeah, I know it's cheesy. But it was, so bite me.

My cock slid into her easily, and Dr F's eyes were glued on the spectacle of our joining. Her hand gripped the base of my dick as she pulled it into her until her fist was pressed against her pussy. And damn! if her pussy wasn't tight as fuck! She then pulled me out and I gave out a small whimper of protest at leaving her, which made her forehead furrow in wonder.

"Was your reaction pretense? It seems genuine, but you are a professional."

I chuckled nervously. "Does it matter?"

"I think it might. In a small way. The idea of you finding pleasure in this does...appeal to me...." She pulled my cock back into her pussy. "Ungh....but I am also very much excited about this aspect..." She took her hand off my cock. "...of our coitus. Now put it all the way in." With an evil grin I gave her the rest of my cock, filling her up and making her back arch and gasp as I hit bottom. "Keep it right there! Don't move!" Dr F's eyes were closed as her hands grabbed my hips and held me tight inside her. She began to rotate her hips ever so slightly. It was an amazing feeling! I know it must have looked boring as hell from the outside, but the way she was moving made her pussy feel like it has hugging and unhugging my dick, and that pressure was located right on the head of my dick. Holy shit! It was the freakiest thing, she was hitting the exact spot that makes me cum, but the way she was doing it wouldn't let me cum!

Dr. F was oblivious to my ecstasy, as she laid back and fucked her self on my cock. A smile was perched on the corners of her mouth, a slight smile she wore for no one else but her. She wasn't giving a rat's ass about my feelings at all, and it was beautiful. I leaned down to kiss her nipple, and she swatted the top of my head like a naughty child.

"No! No breast play for you." I leaned back up, and saw a surprised look on her face. She began to sputter, "Oh, I just did that without thinking...I..."

I interrupted her quickly. "And how did it feel, Dr. F? Doing something without thinking?"