The Milf That Too My Cherry

Growing up, I was a typical skinny, nerdy and insecure teen. I had access to porn magazines through friends, but my romantic experiences never got further than slow dancing at the senior prom. Now, I was a 19 year old who had just signed up for the Air Force, and taking advantage of a few weeks of freedom. As a high school graduation present, my parents had helped me buy an electric guitar, and I would practice in my bedroom, wearing headphones and listening to my favorite records. I was in there one Saturday afternoon changing albums when I thought I heard someone knocking on the front door. My folks were away for the day, gone to visit relatives in a nearby town, and I wasn't happy about having to stop playing.

Before I opened the front door, I peeked out a side window to see who was interrupting my alone time and saw one of my mom's work friends, Mrs. Crews. She was younger than mom, probably around 30, and they were teachers at a local elementary school. She seemed to be melting in the sun, so I opened the door and invited her in. She was tall, close to six feet high, with short black hair and retro-style black rimmed glasses over her pretty smile. I'd always thought she was cute, with smallish firm boobs and a wide set of hips that I had admired several times, swaying side to side as she walked. I'd even appreciated her large buttcheeks and thighs, but I would probably never admit it to any of my friends, or they might think I was weird for being attracted to older ladies with a little extra padding.

"Hi David. Is your mom at home?" she asked.

"No, she went with dad to visit family in Centerville. Probably won't be back until late tonight."

"Aw damn. I was hoping to borrow her lesson plans for next month."

"I think I know where they are, and I'm sure she wouldn't mind."

"Thanks. Did I hear guitar playing when I walked up?"

"Yeah. I've been playing a couple of months, but just in my room, I'm not in a band or anything."

After I'd found the lesson plans, Mrs Crews thanked me and asked, "I've always liked the look and sound of guitar. Can I see it?"

I was taken by surprise, but I showed Mrs. Crews where I had been practicing and she genuinely seemed to admire the look of my setup. She was asking me about my music, who I listened to and what I liked to play, and when I turned to show her a few albums I noticed that she was looking at my bed. A little too late, I remembered that I had left a couple of dirty mags on my bed earlier, because I'd taken advantage of the privacy to jerk off a few loads. She chuckled and grabbed one of the magazines, flipping pages and pausing occasionally.

"Just what kind of practicing have you been doing in here, mister?" she asked coyly, grinning and looking at me over her eyeglasses.

"Well... that's not... I mean... it's something else..." I was stammering and trying to figure out a way to talk myself out of this embarrassing situation.

"Yeah, I'd say this something completely different. Hmmmmm? Just you and these naughty fantasy girls having some wicked fun? You dirty boy! How many times a day do you jerk off? Do you even bother to use any lube before you strangle your poor abused dick?" She laughed, and even though she was trying to embarrass me and my situation, I was starting to enjoy the torture. I found that being talked to like this was kind of exciting, and I was quietly hoping that there would be much more to come.

I couldn't even look at her, but I couldn't deny that I was getting horny either. She kept up the verbal abuse, "Teen pervert! It must have been pretty good too, because your dick is getting hard again." My cock was making a painful tent in my jeans and we both knew that I would need some relief pretty soon, knowing that this woman was humiliating me for masturbating and I was enjoying being humiliated too.

"Have you ever been with a girl before?" she asked. I could only shake my head no.

"So you've never seen a girl naked? Except in a magazine?" I gave her the same reply.

"Well I can't stand to see you this uncomfortable", Mrs. Crews said. "Let me see what you're packing there. Show me the other instrument you've been playing with in your room." She sat down on my desk chair, hiked her skirt up a bit, and spread her luscious legs just enough to give me a peek of lacy pink panties between her soft thighs. I even noticed a small tattoo, what appeared to be a pair of lipsticked lips with blood dripping from one corner. "Maybe I can convince you to appreciate a real woman for once, even if she doesn't look like those skinny chicks in your dirty magazines."

My fingers were shaking, and I stumbled trying to take off my belt and unzip my jeans. I yanked them down about halfway to my knees, then I looked straight into her eyes as I hooked my thumbs into the waistband of my underwear briefs and slid them down. My cock sprang out in the open air and throbbed proudly with my pulse. She smiled and stared at my lewd display, then told me to stroke it slowly. Of course, I did as she instructed, but I was also curious how far we were going to take this.

"Nice and slow... I know how eager a horny young guy can get, but let's make this last, cause I don't want you to cum for a while," she warned me. It took all my concentration to slow my strokes, but she seemed to appreciate it, especially when I squeezed my balls. She moved the chair until she was just a few feet in front of me, pulled her dress off over her head and sat back down in her matching bra and panties, legs spread wide so I could stare at the damp spot covering her pussy. Her nipples were poking through the thin fabric of her bra and she was licking her lips as her eyes were glued to the sight of my hand going up and down my throbbing cock.

"Oh Mrs. Crews," I moaned. "I don't know how much longer I can hold back."

"In that case, I think you should call me Kimmy." She reached behind her to release the hooks on her bra, then slid it off her arms and dropped it on the floor. "And why don't you aim that cock this way, and shoot your hot cum on my titties?"

I kept my eyes on Kimmy as stroked faster, and moved directly in front of her. I must have spurted 5 shots directly onto her tits, and watched fascinated as she smeared it onto her nipples and belly. "That feels so warm and sticky," she cooed before she brought the fingertips to her tongue and licked them clean. Being a typical hormonal young man, my cock started twitching at the sight of Kimmy smearing and licking up my cumload, and that brought a wicked smile to her lips. "You still haven't had enough?"

She crawled onto my bed and peeled off her moist panties before she said "Well hurry up and strip off the rest of those clothes David, cause I'm going to need you to fuck me."

I was naked in about 2.5 seconds, then I crawled between Kimmy's spread thighs and admired the incredible view of this nude vixen in my bed. She grabbed my cock and guided it through the dark forest of her pubes, till I found her dripping wet pussy lips and sank it balls deep in one thrust. "Oh God yes! I'd almost forgotten how good a hard young cock feels!" Her nails dug into my asscheeks as she taught me how to fuck, stroking in and out of her wet cunt for several passionate minutes. We pounded against each other faster and harder, till she arched her back and tensed her entire body in a fabulous orgasm. I lifted her legs over my shoulders and stroked in and out, feeling my balls slapping against her ass.

"Don't cum in my pussy, baby," she begged me. "Pull out and cum on my tits." I nodded and did as she asked, depositing my second load on her nipples. She kissed me deeply and said "I hope you realize that we can't ever do this again. I'd love to teach you more about women, but I think it might be a little dangerous." We kissed again, then she got dressed and left me a sweaty but happy mess.

She was right about one thing. I never saw her again, because a month later I was across the country being sworn in to the Air Force, and by the time I came back for a visit two years later, she and her husband had moved away.