Toby's High School Harem

**All characters involved in sexual activities are 18 years old or older.**

It was a beautiful Tuesday morning and I found myself pondering life as it was shaping up while driving the Mustang. Not three days ago I was a virgin and didn't have a prospect in sight that wanted to fuck me. Now I had fucked two of the hottest girls in school and was on my way to Felicia's house. She texted me last night asking if I would come give her a ride and to come early. She didn't ask me to drive the Mustang but I was in the mood and maybe we'd go somewhere after school...shit!

I forgot I had another tutor session with Danielle Parrish. She roamed in the same circle of friends as Felicia and Melissa. I don't know how close they are or if she's close to Jenna and Jeremy but Danielle used to date the old senior quarterback before he went to college and they broke up. She's one of the best soccer players and was being recruited in state pretty hard. Her grades needed to improve and she also wanted to make sure she wouldn't get overwhelmed when she got to college.

I pull up to Felicia's house and as I'm about to knock when Amanda Harris opened the door. She is a gorgeous woman, youthful to the point I would hate to guess her age, even in the waking hours of the morning she was beautiful. Her long wavy brown hair, messy from sleep, her heavy lidded dark brown eyes brightened when she saw me, and a smile crossed her sexy full lips. She was wearing a loose fit, over sized t-shirt that rested just above the curve of her amazing ass. She was a little bit taller than me and her daughter, her tits were bigger, C-cup for sure, and looked amazing in their natural state under the loose material of Mrs. Harris's shirt. I had learned she used to play softball in college and never gave up keeping fit, her hips, ass and thighs displayed all of that in the most wonderful way. Her ass may not have been as tight as when she was in college and maybe her body filled out to give her the sexiest milf body any guy could desire. That's what I thought of her since the first time I met her while tutoring Felicia at their home on a number of occasions. The reason I say this is because her pajama bottoms look comfortable, 100%, but they drape down, loose, over her body and even still she looks absolutely beautiful as her ass pushes out on the loose fabric to tease me.

Taking a sip of her coffee, her eyes squint mischievously and her hungry smile appears as she pulls her cup away from her lips. "Toby, what a surprise please come in," Mrs. Harris says as she opens the door but not entirely so I have to turn my body so not to bump into her.

"Uh, thanks," I greet her as I twist my body towards hers as I slid comfortably through the narrow space Mrs. Harris left me. "Good morning Mrs. Harris..."

"Amanda," she said with a seductive tone, correcting me.

"Uh, yeah, good morning Amanda," I have never called her anything other than Mrs. Harris the entire time I've known her, and I explain. "I'm here to pick up Felicia for school."

"She left with Melissa just a few minutes ago," Amanda explained with a smile that was trying to be innocent but looked like a hunter sighting their prey.

"Oh," Confused but also thinking a quick exit seemed appropriate I said, "I guess I'll be going then."

"No," Amanda said calmly as if she already knew I wouldn't be going anywhere. "Come, have a seat." She motioned to the empty spot on the sofa. She was where I took her daughter's virginity and I felt my cock pulse with that thought and the image of Amanda actually sitting before me. Sure, she was not wearing make up, she was definitely not dressed to seduce me, her hair wasn't even brushed, and yet she was absolutely beautiful.

"Okay," I said softly. I didn't know what was going on but I felt like butterflies were going to burst out of my fucking stomach right now I was so fucking nervous! I moved to sit on the sofa on the end and away from Felicia's mother but she pulled me so I sat next to her.

"Are you okay honey?" She asked with an over concerned but sweet voice. I felt like Amanda knew something and was slowly drawing me in for the kill shot like a skilled hunter leading it's prey. "Is something bothering you?"

"I feel a little uncomfortable," I said after Amanda put her hand on my thigh and leaned toward me so she could look me in the eyes.

"Is it me?" Amanda bit her bottom lip as her eyes scanned down my body.

"Honestly, I don't know what's going on right now," I let out as her hand moves up my leg and inside towards my hardening cock.

Without looking away from my wide eyes Amanda pulled her phone out and hit a button which brought her television on with us on the screen. She knew everything that happened that night and now her hand was discovering first hand what she's been craving, my hardened cock. Amanda's fingers grip my girth and her eyes closed in a self satisfaction at finding what she desired finally in her grasp.

"Holy shit," I said as my body tenses up but I don't try to get away or stop what she was doing.

"I'm a single woman living alone with my teenage daughter," the way she said teenage daughter made it all sound taboo with her seductive tone. "I have to protect us so I installed a security system. The whole house, minus bedrooms and bathrooms." Amanda said this as she finally took her eyes away from mine and pointed up into the corner of the room were I noticed, in plain sight, the white camera in the corner of room displaying our image on the television.

"I'm sorry for what happened in your house..." Her fingers squeezing my engorged dick stopped my words.

"I didn't like having to watch my daughter getting fucked but I had to make sure she didn't get hurt," Amanda started to stroke me as her words slipped from her lips and her eyes looked into my soul.

"I would never hurt..." Another firm squeeze of my hard cock shut me up.

"Listen," Amanda's voice got serious and her firm grip on my cock never eased up and I seriously thought I was she was going to kill me. "I'm a busy woman and I don't want to slut myself out trying to find a guy that will respect me, care for me when I want it, hold me when I need him and fuck me because I'm horny."

"What?" Lost and confused with her hand firmly massaging my penis through my pants, that was all I could think to ask.

"After seeing you take my daughter, you came inside of her, you took care of her and when she got back home, before going to her room, she called her boyfriend and broke up with him...for you." She slid her body off the couch and to her knees, positioning herself between my legs. "For this," she hungrily said as she worked my belt free and opened up my jeans.

"Holy shit!," Before I could even try to process what she was doing my fully erect cock was out with both of her hands holding my girth.

"Mmm, impressive," Amanda's voice husky, her eyes took on a dreamy look as she gazed onto my thick, vein rippled cocked.

"I can't believe this," I breathlessly said, I wanted to reach out and touch her but I felt like I just wasn't able to move as I stared down at her amazing, soft yet mature face. "You're so fucking beautiful."

Amanda's smile grew, "If you want this," using her tongue like a snake and teased my tip. "I'll need something from you."

"What?" looking into her lascivious eyes as if she has me under her spell. Her hands lightly massaging the base of my shaft which made the head of my dick swell right next to her sultry mouth.

"I want you to be my personal escort," Amanda explained as she stroked the shaft of my cock with both of her hands while my head bobbed dangerously close to her lips. I could feel her breath as she spoke, "I'm too busy to date, and my schedule is all over the place but I have needs."

"Needs?" I knew what her needs were but my dumbfounded brain wasn't operating correctly at the moment.

"When I first saw this magnificent cock take my daughter I was boiling with rage." Amanda told me as she continued her firm massaging of the base of my cock. I was feeling very vulnerable and yet still so fucking hard as she continued. "I wanted to rip this cock from your body and shove it down your throat...but as time went on and the image of this beast invading my pussy filled my thoughts and knew." Amanda paused to lick the tip of my cock and then kissed it as if kissing a relatives cheek in welcome. "I needed this cock, I needed you."

"How?" I wasn't sure what I was asking or who I was even asking. Was I asking her how she needed me or was I asking myself how fucking lucky I was to be sitting with this absolutely stunning milf between my legs, teasing my cock.

"How?" She smiled a seductive grin and her eyes were in flames with her desire.

"How the fuck an I so lucky," I finally let out as I reach out and pull her into my arms and kiss her.

She grabbed the back of my head and pulled me harder into her lips as I devoured her. Without releasing my lips, our tongues exploring each others, quick nibbles of her lower lip, Amanda climbed onto my lap. Even in her natural state, no makeup, and the absolutely comfortable loose fabric covering her gorgeous body from my view she was altogether stunning. "Perfect," Amanda panted as I pulled from her lips to kiss down her neck. She moved her head up and away, giving me access to her body. Her hips ground her pajama cover pussy onto my rigid dick. I could feel the heat from the wet fabric as it rubbed the length of my shaft. "You're so fucking big," her husky voice breathing heavily in heat.

"You're so fucking wet," I counter as she continues to grind into my cock with her soaked pajama bottoms.

"Jeezus, just get that shirt off and let me see you," Amanda demanded in her lust fueled hunger and practically ripped it over my head. Once my chest was exposed she attacked my nipples and it sent shock waves through my body. I grabbed her hips and slid my hands around to her perfect, fleshy ass and started thrusting my body against hers.

"You're amazing," I pull her face off my nipple to look her in those stunning brown eyes. "Seriously the most stunning woman I've ever seen, you make me insatiable!" I declare as I throw her off to my left and get down onto my knees. I push her fully onto her back, grab each or her ankles and spread her legs. She willingly follows my lead in anticipation of what I'm going to do next. I slide my hands along her calves to the back of her knees and lower my head to her pajama covered pussy.

"Oh, thank you, gawd!" Her pleasure ever present in her voice as my mouth attacks her pussy. I eat her as if she was bare and I was licking at her folds. I knew this wasn't going to get her off but I also read that this was a great way to rev up a woman before giving her direct attention. It seemed to be working as Amanda grabbed at my hair and pulled my head harder into her cunt.

"Fuck!" I couldn't take it any more. I wanted more, I needed to actually taste her, feel her pussy on my tongue. I grab at her crotch and rip the material covering her sweet womanhood from my starved mouth. Her neatly trimmed brown pubic hair highlighted her very wet and glistening slit.

"Oh, yes you fucking animal!" Amanda cried as I rest her legs over my shoulders, holding the torn fabric apart while I feasted on her juicy pussy. The musk hit my nose, her tarty taste was heaven on my taste buds. She clamped her legs around my head, I reached up and pawed, pinched and groped her tits through her shirt with my arms wrapped around her legs.

"You taste is addictive," I said between licking, sucking, and flicking her clit with my tongue. I start sucking on her folds, I dart my tongue into her whole as I move from her clit, to licking her entire slit to collect her juices on my taste buds. I trace along the outer edge of her lips before slicing deep as I force my tongue deep down cunt and corkscrew it within her. Her hips sway and press against my ravenous mouth as I find her clit and say hello with a little nip with my teeth which causes Amanda to moan her pleasure.

"YES...YES! OH YES!" Suddenly both of Amanda's hands grab at my head, gripping my hair, pulling my face hard into her pussy while her legs clamped down on me. Her head flew back and her scream of pure ecstasy exclaimed her gushing orgasm. My mouth, cheeks, and chin were being sprayed with her climactic juices as I tried to suck it all in.

"Holy shit," was my remark when Amanda released her climactic death grip on my body. I was so turned on I slid up and kissed her, our lips collided lustfully, our tongues danced, our hands pulling each other as close as possible against our bodies.

"I need this now!" Amanda moaned with desire as she took my rigid cock with both of her hands, moving her hips to align her cum slicked cunt with my meaty dick. I felt her hot, slick slit as she rubbed my fat head along her wet lips.

"Then take it," I said as I pushed almost half my cock into her tight, searing pussy. I was so close to the edge I fell over and felt my climax hit me out of nowhere as I erupted inside of Amanda's tight tunnel. "Oh FUCK!"

"Jeezus," Amanda panted and tensed up with me invading her womanhood, "I can feel everything!"

I kept thrusting, thinking...I just prematurely ejaculated! Amanda was such a goddess in my eyes that even in her absolute natural state she was still a dream come true. At first I saw disappointment when she felt me cumming inside of her. When I continued to fuck her, luckily, without getting soft. I did soften a little but I was still full mast but just not hard as a rock. Amanda's face softened with a thankful look as she got was she wanted, to get fucked.

"You're stretching me out," Amanda moaned as her hips started to gyrate and match my rhythm. Her sopping wet canal coated my cock with our creamy satisfaction.

"You grip me perfectly," I tell her as I start to feel my cock getting more and more rigid as I pumped her pussy. Her cum soaked cunt squelched and slurped as my cock plunged into her depth as I grunted and she moaned our pleasure.

I push her legs up so they are pressed against the sides of her body with my hand to the back of her knees. I look down onto Amanda's impressive body, still fully clothed, wearing that loose fit t-shirt and pajama bottoms did nothing to diminish her beauty. Her natural beauty only enhances my attraction as she is just as beautiful without makeup. I lean down and attack her covered nipples with my mouth. I bite, a little harder than I would if she were topless, which causes her to squeal and moan in pleasure. I continue to pump my cock within her slick, tight vaginal walls. Her hands paw and explore my torso like a woman possessed.

"Oh YEEAAHH!" Amanda's body shook, her face looked pained but her pleasure came through her moans and orgasmic yelps. Her pussy rippled through her orgasm and gushed with her climax which I felt along my entire cock.

"I'm cumming!" I said with a husky voice as my balls feed my exploding cock deep withing Amanda's snatch. As my cock pumps the last of my seed into Amanda's body I pull out and fall onto my ass on the floor.

"I've never," Amanda said to nobody as her legs rested, still spread open from my absent body. Our cum spilling from her slit and onto the couch.

"I can't believe that even happened," I said in disbelief.

"Toby, baby, I believe it did and I know it will again." Amanda said as she slid from the couch to cuddle up to my laying body on the floor.

"I'm sorry about your pants," I finally felt some guilt for ripping her nice pajama bottoms.

"I'm not," she answered as she caressed my chest. Her head resting on my left shoulder and her left leg draped over my slick, flaccid penis. "Now to business..." Amanda explained the nature of our relationship as business of pleasure. I was to be her escort, she was going to pay me $500 but that would be for the entire day. She wanted the boyfriend experience and when I asked about our age difference she scoffed and said, "if a 60 year old man can date a 20 year old girl the a 36 year old woman can damn well date an 18 year old man!"

Amanda and I already were familiar with each other because I was tutoring Felicia and over that time we had discussions that spanned general interests. We obviously never got too personal before today but she admitted she would only continue this as long as she felt a connection and we continued to grow closer over time. She even told me I would be attending some formal events when I would need to dress appropriately and that I was to throw all my over sized clothes away and update to fitting attire. I conceded, of course, and agreed to be her man whore, which made her smile in amusement.

Amanda made it clear that this wasn't a love relationship but she didn't want an empty relationship based solely on sex. She was a busy woman, she traveled for work, she had her daughter, she enjoyed her alone time, admitting she was selfish, and didn't want to stress over finding a man. $500 for a day, guarantied once a week, maybe more if needed for an event or other outing.

Again, how could I say no to that?

Satisfied with the terms of our 'relationship' Amanda got up, I couldn't help but notice the spatter of wetness around the crotch of her pajama pants. My member was coming back to life and Amanda gave me growing penis an appreciative smile and took it in hand as if remembering a fond memory. She led my, her hand in mine, to her private bathroom which was attached to her impressive bedroom.

The bathroom looked modern had to vanity sinks, a very nice looking toilet that looked more sophisticated than the TV at home. Then there was a nice two person soaking bathtub and a large shower designed to drop the water like rain from above.

Since I was naked already, Amanda turned to face me and raised her arms and waited for me to pull her shirt off. I walked up behind her, reached around the front of her waist, and gently pulled her into my body. My nearly erect cock pressed to the underside of Amanda's amazing round bottom and into the fabric of her pants. I grab the bottom of her shirt, she was grinding against me slowly, seductively while her hands were still up in the air. I lift her shirt up Amanda's body while putting my hands under the fabric so I can caress her body while slowly exposing her stunning torso and beautiful breasts.

I toss her shirt aside and run my hands down the underside of her raised arms. Her skin is soft, her body firm as she moans to my touch. Amanda's head falls back onto my shoulder and I slowly kiss her neck, down to her shoulder as my hands softly explore down the sides of her body. Amanda brings her hands down to my head and her fingers weave into my hair, massaging my scalp. I kiss my way back up to her neck as my hand travel the center of Amanda's stomach and up to her full, perfectly shaped tits. I couldn't believe I was even able to see this stunning woman naked let alone touch her the way I was.

"You are full of surprises," Amanda cooed as she ran her hands down her body but then to my hips to help push her ass onto my throbbing cock. "You know how to fuck and now it seem you can love too."

"I want to be everything you want me to be," I said between kisses. She turned her head and our lips met in a slow yet passionate kiss as I caressed and fondled her nipples gently and attentively rolling her perky points with every part of my hungry fingers.

I kiss my way down her past her shoulder and then to the nape of her neck. I moved her long brunette hair over her right shoulder, with my right hands while my left felt my way down her stomach. Amanda softly moans and her breaths are heavy as I kiss my way down her spine. I rest on my knees and move my hands to her waist and slowly, kissing her perfect ass as her cheeks appear, pull her pajama bottoms down over her amazing bottom. I could smell our previous experience as her musk was ripe with sex which made my cock ache with desire.