The Land of MILF and Honey Ch. 01

"Watch it, nerd!!" Ronnie Tillerson, the head of the football team grunted, pushing me to the floor on Monday. It was also my 18th birthday.

Some hell of a birthday it had been. It had been two months since my dad had walked into the kitchen one morning and announced his mistress was pregnant and he was leaving us.

Now, Mom and I were both working to pick up the bills, which Dad flat out refused to help with. We had to downsize, moving to a middle-class neighborhood. I was surprised how positive she had been throughout the divorce. I was eager to help her... but I couldn't stop thinking how life could have been different.

Like it had been before.

And that's what I thinking about as I stood in the middle of the hallway, accidentally blocking the prideful strutting of 'his Lord and Majesty', Ronald Tillerson. And now we return to the beginning of this story.

- -

The crack of my head on the hard floor couldn't have been heard by anyone else, but in my head it sounded like an explosion.

Getting bullied was one thing. The laughter was another. The snickers and picking on the little guy.

"Dude are you okay?" My buddy Rob asked as he ran up. My friend Chandra was along with him, nervously hugging her books to her chest, the large-rimmed glasses barely held on her nose.

They helped brush me off, a lump already forming under my blonde hair. I just hoped my mother wouldn't notice, as she was already worried about me ever since my dad had split almost a year ago.

"You're sure you don't want to go to the nurse?" Chandra asked as we pushed our way through the glaring crowd. I nodded, clenching my fists but controlling my anger.

After school, I decided to go for a walk in a nearby park to clear my head. It was popular with runners, bikers, dog walkers, etc. Right now, it wasn't as active due to it getting dark.

As I rounded a corner into an open area, a group of people were in the grass a small distance from the path. I decided to slow to a walk and saw the group had just finished doing yoga in the park.

The teacher rose up and dismissed the group. As I observed the people rolling up their mats on very well endowed, woman caught my eye.

I took inventory of her. Beautiful G-cup breasts in a peach colored tank top (a white jog bra held them snuggly in place but did allow her nipples to appear). She bent over to pick up her mat and those tight yoga pants were black and showed off her lovely ass.

She then turned around and my jaw dropped.

Dorothy Baxter, our principal was the subject of my observation. Upon seeing me, she waved and walked over. My cock was already hard from seeing her and I wanted to get out before the situation got embarrassing but it was too late to leave.

"Thomas, how lovely to see you." she said with her usual smile, "It's a lovely day for a stroll in the park."

"Yes it is," I replied.

"So, how are you doing?" she asked in her ever-pleasant way, "I heard about the scene in the hallway today."

"It's nothing," I replied with a shrug, "I've been bullied so much, I have a callous toward it really."

She nodded slowly, as if trying to examine my feelings.

"Oh my," she said as she checked her watch, "Rick will be home any minute and I still have to prepare dinner."

"Thomas," she said after I helped her gather her things, "would you mind escorting me home? I'd just safer walking home with someone as it gets dark."

"I'd love to," I replied and we set off. I couldn't help but sneak as many glances as I could at her ass, the yoga pants so tight it seemed they were practically painted on.

When we arrived, I helped her carry in her things.

"Go ahead and sit down Thomas," she said, "I'm need to change."

"Ok Ms. Baxter."

"Oh please Thomas, you're already 18. Feel free to call me Dorothy."

"Ok Ms. B-," I caught myself, "I mean Dorothy."

She gave me a warm smile and headed upstairs. As I imagined her naked, my cock filled even more and I just struggled to get it go flaccid as she was upstairs. Finally, she returned and my jaw dropped for the 2nd time in under an hour.

She wore a silver robe with a matching bra. In her hands were two glasses of iced lemonade.

"I want to thank for walking me home Thomas. Not enough men care anymore about a woman traveling alone."

I smiled and accepted the glass as she sat down. She took a long sip, the golden droplets landing on her boobs and even in her deep cleavage, accentuated even more with her bra.

As we talked more, her phone rang.

"Hello?" she asked pleasantly, "Oh hi Rick! When are you...?"

The smile disappeared from her face and she set down her glass.

"No Rick," she said with a shaky voice, "that's fine. I'll um... be fine here by myself."

She disconnected the call and appeared ready to cry.

"Are you alright?" I asked and she slowly nodded, wiping her eyes.

She lifted her head however and I can see red eyes and running mascara. I hate to see a woman in emotional distress. So, I closer to her and place a comforting hand on her shoulder.

"Dorothy, why are you so sad?" I quietly ask.

"Nothing Thomas" she laughed, though I could hear the pain, "just something I should've gotten used to by now.

"Please tell me," I whisper moving closer to her.

She looked at me, seeing the care in my eyes and she took a deep breath.

"Ok Thomas, but please keep it to yourself. Today is my anniversary and I planned a romantic evening with my husband. Now he tells me that he left for a golf weekend with his buddies." she said with strained emotion.

"That was so thoughtless of him. Why would he leave a sexy hot woman like yourself to play golf? Is he blind or just clueless?" I asked.

"You think I'm hot and sexy Thomas?" she sniffled and raising her eyes.

"Of course! I'd give anything to be with a woman half as attractive as you are." I said with a smile and Dorothy smiled as well.

"Well Rick is clueless because he treats me more like a maid than a wife! We haven't had sex for far too long" she states with disgust.

"I believe he's blind! I would have trouble letting you leave the house for work. Just look at yourself in that outfit, you are the very definition of a sexy hot MILF!"

She looked at me and chuckled. "Oh, please! You probably wouldn't spend time with this washed up old woman either."

I scoffed. "Dorothy! You are absolutely not old. I know thousands of women would kill to have your figure!"

She smiled. "You're sweet Thomas."

She gave me a big hug which provided as much body contact as possible. Her jigging tits began to excite my libido. I stayed close but not to close because with her position at school I didn't want a nosy person making trouble for Dorothy.

"Well," she said, "looks like we're both pretty lonely tonight."

"Yeah..." I replied, slowly looking up at her.

It felt like music played as our eyes met and before I could process what was happening, our lips met. Her lips were soft but determined as her tongue met mine.

"Ms Baxter..." I began as she separated from me but she placed her finger over my mouth.

"Dorothy, Thomas. Don't talk. Just let me reward you for being such a gifted, caring boy."

Her lips met mine again as she reached into my pants, pulling out my throbbing meat, already oozing precum in large amounts. I had measured it numerous times, finding it was 7'' while flaccid while maxing at around 9 or 10. And I was fully hard.

"Would you look at that?!" she exclaimed with a large smile, "Someone getting hard to their principal? This is the first a woman has touched your cock huh Tommy?"

I could only nod as she smiled and gave a long lick from my root to the base, swishing my precum in her mouth.

"Sweet and salty. Just delicious. You have a beautiful cock between your legs. Strong and hard."

She leaned over me, giving me a full view of her skill contained boobs, "How would you like the special treatment Rick missed out on?"

My cock throbbed rapidly and she giggled. As we got into her candle-lit bedroom, I picked her up and began to kiss her mouth, face and neck, my cock nestled against her pussy.

Dorothy moaned softly, intertwining my hair with her fingers. I then palmed her ass, the dough-like flesh squishing through my fingers.

"You're such a good boy Thomas..." she moaned softly, "such a good boy..."

She instructed me to lay on the bed and I immediately complied. "Close your eyes honey. I want this to be special."

Though it took every nerve in my body not to peek, I didn't open them until she said, "Happy anniversary Thomas."

I opened them and my prick got so hard it nearly shot off. Dorothy's huge knockers stood proudly, her erect pink nipples just waiting to be sucked. And her pussy! Pink, wet and glistening.

"Holy shit..." I breathed out and she smiled before turning around and bending over, giving me a full view of her ass, just as flawless as the rest of her.

"You think you can handle this Thomas?" she asked seductively with a long lick to her lips.

"Absolutely..." I said, still drinking her full and ripe melons. Gravity must have had a hard fight on its hands. They didn't sag in the least as she licked her fingers and softly traced her nipples, getting me even harder.

"You naughty, naughty boy..." she said as leaned over, letting her boobs lightly brush against my cock, "getting big and firm for your principal."

She crawled onto the bed and kissed me tenderly while pumping my cock, getting her hand and cock slick with my leaking seed.

"How does it feel baby?" she whispered in my ear.

"F-fucking incredible..." I moaned as she smiled before moving her hand down to my bloated sack, where it felt as if my balls were floating in all the cum I had produced in the last few minutes.

She began to jerk me off again, faster this time as we made out passionately, my hands groping her soft tits and ass. We were now lovers, our lips furiously attacking each other, groaning into each other's mouths.

"Don't worry Thomas. Your cock is going to feel so much better..." Before I could respond, her lips closed over my head and she began to suck using her tongue to coat my cock in saliva as her head bobbed vigorously up and down my pole.

Her cheeks hollowed as she sucked me deeply, her tongue teasing my base. All signs of my school principal were gone, Dorothy slurping loudly as she carefully got every inch perfectly.

"Oh fuck..." I moaned as my eyes rolled and I fell onto my back.

I could her lips form a smile around my prick as she went faster, her saliva dripping down to wet my sack. Eventually, she stopped moving just holding her head against my crotch.

"Are you okay?" I asked leaning up before she began to vigorously move her head from side to side as if she was having a seizure. It was absolutely amazing. It felt as I lost feeling in any part of my body besides my shaft at that point.

I could hear numerous wet smacks as my head collided with the back of her throat. I was in fucking heaven, the mirror on the back of the door, showing my hot principal on her knees, head bobbing on my cock at the speed of light.

She looked like the very definition of a MILF. Her juicy ass cheeks were on full display, sitting on her sexy heels as her hair was spread on my thighs. She finally pulled back up, my cock glistening with her saliva and lipstick.

"I've never met a cock that survive one of my blowjobs. You may give me some satisfaction after all."

"Wow..." I said as I squeezed her ass.

We began to kiss passionately before I moved down to her tits, hearing her soft moans as she continued to stand, running her fingers through my scalp.

"Dorothy sounds too old for a hottie like you. You need a younger and hotter nickname." I told her. I knew I was pushing my luck but she seemed to like it.

"People called me Dot in college when I was young. And frankly, I feel young and exciting right now," she moaned as she lay back on the bed.

I bended over and began to lick her pussy. I could feel her body writhing under me. She began to get more vocal.

"Fuck, Rick has never done this for me..." she groaned as she played with her tits.

I laughed internally as I began to lick inside her pussy, giving her the loving she desperately needed. She tasted absolutely incredible as I licked in slow circles.

"Yes baby... that feels so good..."

Her moans got louder. Finally, I found her clit and immediately attacking, sucking the flesh vigorously.

"Fuck yes! SUCK MY CLIT!!!!" Dot screamed as her nails dug into my head. It hurt somewhat but the pleasure of her pussy overshadowed everything else.

Soon she tells me she going to cum and it will be huge.

"Cum for me Dot." I said, "Don't hold back. Let the college you come out. No repression, no boundaries. Allow the climax to wash over you."

Dot covered her mouth with a pillow and I hear a series of muffled screams. Her juices flooded my mouth, filling my cheeks as I struggled to swallow the years of her unfound relief.

When she finished, I picked her up in my arms and she begins kissing me passionately. When she came up for air, she kept thanking me.

"I want you to fuck me Tommy," she moaned as she spread her pussy lips, "have your way with me."

Gently laying her back on her bed, I pulled her legs up and stood between them. She reached out and guided my fully erect cock into her pussy, making us both as my swollen head pushed into her.

"Yes Thomas! Momma needs Daddy's big fat cock!" she moaned with tears in her eyes. I gently pushed inside, not wanting to hurt her.

She pulled me in for a long kiss. "Don't make love to me Thomas. I need to be fucked!"

Without further ado, I pulled out to the tip and slammed back in, making her scream. I was quickly going full throttle, pounding furiously as my balls connected time and time again with her wet cunt.

"Oh fuck yes!!" I shouted as we moved toward each other while gaining speed.

"Yeah! You like that?! Your huge cock pushing deep inside your slut of a principal?"

"Yes! It's fucking great!!" I replied, raising my hand to squeeze or slap her bouncing tits. Soon she was on top, both of us moaning or crying out as she rode my pulsing cock like a damn professional.

During this marathon, an observer would've seen her bouncing violently on my cock, her G cup breasts creating an almost hypnotic motion or bent over holding a bedpost allowing me to drive my cock into her pussy from behind.

The entire time she screamed about that her pussy being split open, no one has ever been this deep, I was battering her cervix. I had never felt such pleasure, far outweighing even my greatest wank session.

When my cock started to droop, she would begin sucking my cock or using her breasts to reinvigorate it. As I was fucking her from behind again, I was still sucking her tits and thrusting with growing power. "Oh fuck Thomas! I'M GONNA CUM!!!!!!" I picked up speed, her ass rippling as I made contact.

She screamed loudly as I didn't let up, her juices spraying all over me and the bed.

"I didn't know I could squirt," Dot said and I laughed.

She began to cum again, screaming my name repeatedly as her pussy went off like a cannon, expelling her juices so hard I nearly fell out. I soon rolled her over, her feet my her head as I continued to thrust vigorously into her.

"Yes baby! More!" Dot begged me.

I clamped my teeth as my balls tingled while Dot looked up at me with love in her eyes.

"I'm about to cum Dot!" I shouted, thrusting madly.

"Do it baby! Cum inside your principal. Give me a child and let everyone know I'm your's!!!!"

My world exploded as we cried out together, the first thick rocket of jizz entering her waiting cunt. What felt like a thousand more hard blasts followed. The pain was as great as the pleasure as I finally ran dry.

We lay beside each other, kissing tenderly. At the end of the marathon, we took a shower together, which included even more sex. We changed the bed sheets and curled up in her bed.

"Are you feeling better?" I asked as I kissed her forehead.

"Absolutely, that was the absolute fucking best!!. From now on, I plan to let Dot out more!" she exclaimed, "but only for you daddy."

Before I left, we did it every room of the house and I filled all her holes with cum. Finally, after yet another fuck filled shower, she sucked me off at the door until I blasted another load down her throat.

"A good boy in school and in bed," Dorothy giggled as she licked me clean, "I think I finally found a way to pass the time between those meetings."