My name is Jake Tillman and I’m a senior at Rockford High. I get good grades and I’m popular with the girls. Being a star in the 100 meter dash and the high hurdles doesn’t hurt my popularity in the slightest.
The crowd I hang with uses Bill Clinton’s definition of “sexual relations”. We have oral sex for fun and don’t consider anything short of actual penetration to be real sex. When I go on a date, I can expect a blowjob or at least a handjob. The way it usually works is, the girl I’m with will suck my dick or jerk me off, then I’ll go down on her and get her off a time or two (or three or seven, whatever) and then she’ll get me off again. It’s all very casual and relaxed. Only two girls have let me screw them, but all in all, I’m pretty happy with my sex life.
My best friend is Bill Roth. Bill’s a basketball star and gets more head and pussy than I do. A girlfriend of his named Amber has always been home-schooled and loves to get away from her over-protective parents and have fun. Amber and Bill get together whenever she can get free and they fuck like rabbits.
Bill introduced us and we learned pretty quickly that Amber likes fucking with an audience and doing more than one guy at a time. Just as you see in porn videos, Amber likes to be doggie-fucked by one guy while blowing another guy kneeling in front of her. The first time we tried it, I was so turned on that I blew my load in her mouth in two minutes flat! Since then, I’ve had my turn at the other end, cumming in a condom inside her pussy. I’ve screwed her and cum inside her – always with a condom – several times and she’s blown me, at last count, eleven times. Amber might not be the best looking girl I know, but she certainly is the easiest!
One Wednesday after school, I stopped by Bill’s house on the way home. His mom’s car was in the carport, but Bill’s car wasn’t around. The Roths and Tillmans are all good friends and we come and go at each other’s homes pretty freely. I usually go in through the unlocked back door, so I parked my car in the street and walked around toward the back of the house. As I walked through the carport, past the side of the house, I noticed a light on in Bill’s mom’s bedroom. The curtain was apparently caught on a chair or some other obstacle and didn’t cover the bottom corner of her window. I could see inside. Mrs. Roth was masturbating. To say I was surprised would be an enormous understatement. Mrs. Roth was nude and slumped in a chair facing almost directly toward me. She had a silver vibrator and was fucking herself with it while pulling her nipples. I got an instant hard-on.
As I was taking all this in, it occurred to me that Mrs. Roth might be able to see me spying on her, but it was pretty dark under the carport, she had her eyes closed and the lights were on in the bedroom. I figured I was safe. I dug out my smart phone and started taking photos. It’s a good thing I routinely have the auto-flash turned off or I’d have busted myself with the first photo. After taking several pics, I switched to video and got almost nine minutes of Mrs. Roth bringing herself to four very energetic orgasms. She looked really good. She had excellent muscle tone, a small waist and full, B-cup breasts. When she was finished, I pocketed my phone, scurried out to my car and got the hell out of there. At home in my room, I uploaded the photos and the video to my computer, reviewed my work and jerked off. Mrs. Roth was hot, a true MILF! She looked like an early-forties woman who was doing her best to stay in shape and succeeding brilliantly.
Now, I wondered, what the hell am I going to do about this situation? By that evening, I had a plan.
I copied the pics and the video to a CD.
I dropped the CD into a padded mailing envelope with a note that said, “Life’s funny that way!”
I addressed the envelope to Mrs. Roth. I did all the writing in block letters with a ruler, so that no one could do a handwriting analysis.
I mailed the envelope at the local post office on my way to school the next morning. I was pretty sure it would be delivered the next day, which was Friday.
Note: I wore gloves for all of this. There was no way for her to know who sent the CD and that’s exactly the way I wanted it.
I let Mrs. Roth stew until Tuesday, when I knew Bill would be on a bus heading for an away game. Bill’s parents were divorced and his father had been out of the picture for years, so I assumed Mrs. Roth would be alone. I parked in the street in front of the Roth residence and let myself in through the back door, as usual. I was carrying a small gym bag equipped with certain hidden features. Mrs. Roth was sitting at the kitchen table, drinking a cup of coffee and staring at the wall.
“Hi, Mrs. Roth! What’s new?”
“Oh, nothing,” she mumbled, looking distracted. “Same ‘ol, same ‘ol.”
Well, I knew that wasn’t true. “Just thought I’d drop by and see how you were doing,” I lied.
“I’m okay” She obviously wasn’t in the mood for small talk.
“Well, I said, “you never know when something interesting will come along.” I paused for effect. “Life’s funny that way.”
It took a moment for the significance of my comment to percolate through her consciousness. Then she looked at me, wide-eyed.
I smiled, winked and nodded. “Life’s funny that way!”
Mrs. Roth slumped back in her chair. “It was you, Jake? Oh, god, it can’t be you!”
I set my bag on the table with one side oriented toward the counter and pulled up a chair across from her. “Take it easy now. It’s not as bad as you think.”
“Not bad? My son’s best friend saw me doing ... that? You took video?” Her voice was shaking. “Oh my god, Jake, what do you want?”
“I don’t want much. I enjoyed seeing you jilling off. You look really fine. I’d like to see you a bit closer up, though.”
“Forget it, mister! You wouldn’t dare show that crap to anyone! You’d be arrested for peeping, you know.”
“Oh, I don’t think so. You don’t have any evidence that I was even here. It’s a ‘he said-she said’ case. Anyway, I checked and peeping is a misdemeanor. Even if I was convicted, I might get a fine and some community service, but that’s it. You, on the other hand, wouldn’t like it at all if that video was anonymously uploaded to a couple of those amateur porn websites, especially if the link to the video was leaked around town. I’m pretty sure you have more to lose than I do.”
If looks could kill, Mrs. Roth would have had a dead teenager in her kitchen. “All right! What’s it going to take to get that shit away from you and be sure you don’t have copies?”
“To start with,” I said, “I’d like you to stand up right over there and take off your top.”
Mrs. Roth sat for a few moments, weighing her options. There weren’t many. She got up and stepped over to the spot I’d pointed to, next to the counter. With an angry expression, she unbuttoned her blouse and hung it over the back of her chair.
“Now the bra,” I said.
Mrs. Roth reached behind her in that way women have and unclasped her bra. With a look of contempt, she tossed it on top of her blouse.
“There! Are you happy now?”
“Yeah, I’m happy, but we still have a ways to go before I’m as happy as I want to be. You need to get those shorts off and your panties if you’re wearing any.”
“You bastard,” she snarled. “You piece of shit!”
Mrs. Roth angrily stripped off the rest of her clothes. She stood with one arm covering her boobs and the other hand over her snatch patch.
I stood up slowly and walked toward her. I stopped a foot and a half away and looked her up and down. “You don’t mind moving your hands, do you? I can’t see much the way you are now.”
She lowered her hands to her sides, looking resigned.
“Don’t move, Mrs. Roth. I’m not going to hurt you.” I put my hands on her upper arms and slowly ran them up to her shoulders. She flinched when I first touched her, then held still. My hands moved down her chest to her breasts. I kneaded her breasts gently and caressed her nipples. Her tits felt excellent. Mrs. Roth reached behind her, gripped the edge of the counter and closed her eyes. I bent and drew a circle around her left nipple with my tongue. She made a barely audible “ummm” sound and sighed an exasperated sigh. I sucked her nipple between my lips and inched my hand toward her pussy. Mrs. Roth apparently understood the futility of resistance and soon my fingers found their way to her slit. I pushed one finger into her and felt her slickness. I used her natural lube to massage her clit.
“You son-of-a-bitch,” she whispered huskily. I pushed two fingers into her and pumped them while sucking her nipples. “You fucking son-of-a-bitch.”
As I finger-fucked her, Mrs. Roth held my head and tilted her hips toward me. I stopped for a moment and boosted her up onto the counter, then slid a chair over and sat between her thighs. I parted her pubes and licked her pussy. “Oh,” she moaned. “Goddamnit!” She slouched against the cabinet and opened her legs all the way.
Mrs. Roth had a very nice tasting pussy and I explored as much of it as I could reach with my tongue. It wasn’t long before she began pulling my face tight against her and panting. A continuous “ahhh, ahhh,” sound came from deep inside her as I sucked her clit. It wasn’t long before she shivered and released a long “uhhhhh” as she came.
.... There is more of this story ...