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.
I stood up and pushed the chair back. “That was nice, wasn’t it? You taste good. I loved feeling you cum. Do you want me to do that again?”
Mrs. Roth swallowed. Her face and upper body were flushed. “Fuck you! I want you to get out and never come back, that’s what I want!”
“Well, considering the circumstances, what you want doesn’t count for much.” I helped her down from the counter. “We have one more piece of business to conduct before I go.” I kicked off my shoes, unbuckled my belt, opened my jeans and took them off, along with my shorts. I had a serious hard-on and my dick was dripping. I hopped up on the counter and pointed to my erection. “Welcome to the blowjob portion of our program!”
Mrs. Roth looked horrified. “Oh, shit!” she whispered. “Don’t make me do that! I only did that for my husband on his birthday!”
“I don’t mind if you’re a little out of practice. It’s like riding a bicycle. It’ll all come back to you.” I pulled her to me and wrapped her hand around my cock. I moved it in the usual jerk-off motion. “Just start with your hand. Get used to it. Come on, you remember what to do with a dick, don’t you?”
Mrs. Roth jerked me hesitantly at first, then she must have decided to get it over with. She jerked me faster, using both hands. Soon, I was starting to feel it.
“That’s good, I like that, but you need to start blowing me. I want to feel your lips and your tongue. Suck my cock!”
Mrs. Roth dropped her head and took me into her mouth. She stroked my shaft and bobbed her head. It wasn’t enough.
“I can’t feel your tongue, Mrs. Roth. Use your tongue! Ahhh, yeah, that’s better. Much better. Yeah, suck me!” I held her head and thrust into her mouth. Mrs. Roth must have been pretty skilled at deep throating at one time; my cock entering her throat didn’t faze her in the slightest.
“You’re doing fine, Mrs. Roth. I’m going to cum soon and you need to let me cum in your mouth. Don’t swallow if you don’t want to, but don’t stop sucking me until I tell you to. Hold the end of my cock in your mouth and stroke me. Suck hard when I cum. I’ll tell you when you can stop.”
My orgasm crept up my body and I humped Mrs. Roth’s mouth harder. “Fuck, that’s good! Gonna cum in your mouth! Yeah, cum in your fucking mouth! Ahhh, fuck-fuck-fuck!” I came, sitting in my best friend’s kitchen, shooting my sperm into his mom’s very unwilling mouth! What could be hotter?
I kept Mrs. Roth right where she was, sucking my dick and stroking me for at least two minutes after I was done. When I let her go, she lunged for the sink and spat out a mouthful of saliva and semen. She made a beeline for the table and her cup of coffee, which she used as a mouthwash, spitting into the sink again. I stayed where I was, admiring Mrs. Roth’s body and playing with myself.
“Now will you get the hell out of here?” she rasped. “Jesus fucking Christ! You made me blow you, for god’s sake! Fucking pervert! Get out of here and leave me alone!”
I slid off the counter. “No problem. I’ll be going now.” I pulled her to me and groped her tits. “You give pretty damn good head, Mrs. Roth. It was fun eating you and more fun having you blow me.” I picked up my clothes and got dressed. “I’m sure we’ll be able to come to an arrangement that satisfies both of us.”
“What do you mean? We’re through! You have to give me the pictures and the video! I did what you wanted, didn’t I? You can’t keep coming back and wanting sex from me any time you get the urge!”
“Well, you’re partly right. We’re not going to keep this going for very long. There’s too much chance that one of us will make a mistake and neither of us wants that. I am going to want more from you, though.” I clapped my hand over her pussy. “I’m going to want to get my cock inside this vagina. I want to cum inside this vagina and do it without a goddamn condom! The sooner I get what I want from you, the sooner we’ll be done.” I pushed a finger into her and gripped her tit. “Listen here; I don’t expect you to trust me, but I’m going to do what I told you I’d do, including deleting those files and not keeping any copies. We’re going to do what we did today a few more times and I’m going to fuck you in whatever positions strike my fancy. As long as you’re cooperative, everything will be fine. I’m not out to hurt you or wreck your life. I’m a horny eighteen year old boy with a chance to fuck a fine looking woman and I’m not going to let that chance go by.”
I released Mrs. Roth and picked up my gym bag. “I’ll be seeing you.”
In my car, I checked to be sure my video camera was still running and the connection to the tiny HD lens I’d mounted in the side of the bag was secure. I watched a minute of Mrs. Roth blowing me, just for quality control purposes. The image was sharp and clear. At home, I edited out the beginning and end of the video, along with anything that made it look like we were doing anything that wasn’t consensual. When I finished the final edit, I watched the whole thing and jerked off. Then I copied the video to another CD and made a quick trip to the post office, mailing it to you-know-who. I expected Mrs. Roth would have it in the morning mail.
At track practice the next day, I ruptured a minor ligament in my right calf. It wasn’t serious, but the broken ends of the ligament were raw and it hurt to walk. The team doctor told me to stay off my feet as much as possible and give it a couple of weeks for the ends of the torn ligament to heal. He gave me a medical excuse to cut school for the rest of the week. There was no use hanging around the house being bored, so before I went home, I called Mrs. Roth from the phone in the student center so as not to leave any cell phone trail.
“Hi, Mrs. Roth!”
“Jesus,” she yelled, “do you have no shame? What the fuck are you trying to do to me? Another goddamn video?”
“Take it easy; that file will be deleted, right along with the other files.” I held the phone away from my ear as Mrs. Roth screamed at me. When she ran down, I managed to get a word in. “Do you want all this to be over by the end of the week?’ I asked.
“I want it to be over now! What are you talking about?”
“I have a slight injury that’s keeping me out of school for the next two days. If you can come to my house in the morning for a couple of hours tomorrow and Friday, we can clear everything up and go back to our normal lives.”
“Well, shit! If that’s what it takes, fine. Is 10:00 alright?”
“That’ll be good. See you then.”
A few minutes after ten on Thursday, Mrs. Roth parked out front and walked to the house. She was wearing a business suit and carrying a briefcase. I let her in.
“What’s with the office attire?” I asked. I was only wearing a frayed pair of cargo shorts and suddenly felt massively underdressed.
“If anyone asks why I’m here, you can tell them I work for the insurance company that’s handling the claim for your injury, whatever the hell it is.”
“That’s smart. I like the way you think.” I took the briefcase and put it in the coat closet, then I handed her a piece of paper that read, “Don’t say a word until I say it’s OK.” I hung her jacket in the closet and hobbled down the hall to the guest bathroom, using a cane. Mrs. Roth followed me. The next piece of paper read, “Take off your jewelry and all your clothes and leave them here. I’ll be in my room.”
Five minutes later, Mrs. Roth walked into my room with a towel wrapped around her. “You can speak now,” I said.
“What the hell was that about?”
Instead of answering, I reached for the towel. Mrs. Roth shrugged and handed it over. I checked to be sure there weren’t any hidden bugs in it and tossed it onto the bed. “I needed to be sure you weren’t wearing a wire,” I said. “It seems that you weren’t, so...” I dropped my shorts, leaving me as naked as Mrs. Roth. “Let’s get started. I think a long, slow blowjob would be an appropriate beginning. Get down on your knees, please.” Mrs. Roth did as she was told.
“Here’s the general plan for the morning,” I said as she stared to suck me. “First, you’ll blow me and I’ll nut in your mouth.” I pointed to my desk. “There’s a Big Gulp cup right there; you can spit into that if you don’t want to swallow. And yes, I appreciate the irony of you spitting a load of jissum into a Big Gulp cup. There’s mouthwash next to the cup. After you blow me, I’ll go down on you and give you some orgasms. I love getting girls off that way, so that’ll probably take us a while. I recommend you relax and let me eat you. I want you to cum as much as you can or until I get tired. Please try to enjoy yourself.” I pulled Mrs. Roth’s hair tight behind her head and fucked her face. “After we’re through with the pussy eating,” I continued, “you’ll suck my cock until I’m good and ready and then we’ll fuck. I want to do missionary and doggie and cowgirl. We’ll probably spoon, too. I’ll decide later what position we’ll use when I cum. I’m going to cum inside you and, as I told you yesterday, I won’t be wearing a condom. Are you on birth control?”
She pulled off my dick. “Yes, that’s not an issue. I had my tubes tied after Bill was born. Do what you want, you asshole.” She opened wide and I went in deep. At least Mrs. Roth wasn’t fighting me. She must have decided that her best bet was to make me happy, so I’d give her the files.
I let Mrs. Roth blow me for a good ten minutes before I was ready.
“Okay, you’re doing just fine. I’m going to cum any time now. Same drill as yesterday. Don’t stop till I tell you. Oh, shit, that’s perfect! Jerk fast, suck hard, fuuuuuck, ahhh, ahhh, suck, suck, mmmmm, yesssss!”
Mrs. Roth did exactly what I wanted and my orgasm was one of the best. When I released her, Mrs. Roth spat and rinsed while I wiped off my dick. I motioned her to the bed and had her sit on the edge.
“Just lie back and I’ll kneel right here. This should be fun for both of us.”
I stuck my face and fingers into her pussy and had her cumming in less than five minutes. I tried to count her orgasms, but after a while they all sort of ran together. Sucking her clit and flicking it with my tongue produced the most dramatic results. Whether she had taken my advice about relaxing and enjoying herself or she just loved being eaten, I couldn’t say. In any case, Mrs. Roth came more than any girl I’d known. When my neck began to cramp, I eased off with my mouth and just fingered her slowly until she recovered. I sat on the bed and flopped down next to her.
“How you doing?” I asked.
“Shit,” she breathed. “That was so good! I’ve never cum that much before.” She smiled a guilty smile. “I think the fact that you’re forcing me to do this adds spice and makes it better.” She shook her head. “Not that any of that makes it right. You’re still a son-of-a-bitch blackmailer.”
“While that may be true, I’m the son-of-a-bitch blackmailer whose dick you’re going to suck right now and the guy who’s going to fuck you in the very near future.” I ran my hands over her body. “You really are beautiful, you know. This is, by far, the best sex I’ve had in my short life.” I held Mrs. Roth’s face. “I am going to delete those files. I know you aren’t fool enough to trust me, but I’m going to do it. I’ll let you do it tomorrow when we’re finished if you want.”
“Bet your ass I want to! I definitely don’t trust you, but, as you said yesterday, my choices are limited.”
I scooted up to the center of the bed and Mrs. Roth took her place between my legs. I was just this side of completely flaccid, but she quickly had me standing tall. When I was ready, I pushed her onto her back and rubbed the head of my cock up and down her slit. “Any last words?” I asked. Mrs. Roth shook her head and raised her hips. I slid into her wet pussy.
I don’t care what anyone says, the feel of fucking with a condom and fucking without a condom is night and day. The sensation of gliding inside her slippery walls, feeling every inch, actually touching her instead of having a sheet of latex between us was a revelation.
“Goddamn, you feel good,” I said softly. I pushed myself in all the way and held still, soaking in the experience. Mrs. Roth surprised me then. She began squeezing me rhythmically with her interior muscles. “Mmmm, shit!” I said. “That’s a new one for me.”
“My ex-husband, the whore chasing bastard, used to love this.” She looked into my eyes and smiled. “It feels good to me, too!”
I enjoyed her ministrations for another couple of moments and then got down to the serious fucking. I’ve never had so much fun in my life! We fucked in one position until I got dangerously close to orgasm and then we took a short break before trying another one. Mrs. Roth came repeatedly in all of them. I found fucking her from behind while she was bent over the bed especially stimulating.
“Oh, shit, don’t move!” I flexed my cock as hard as I could, holding back my orgasm. “Fuck, that was close.” I took a couple of deep breaths. “Just hold still and I’ll pull out.” I backed out of her and we sat on the bed. My cock was rock-hard.
“Why are you fighting it?” asked Mrs. Roth. “If you need to cum, go ahead and cum. You’re young. Take ten minutes and I’ll suck you until you’re hard again.” She touched my balls lightly with her fingers. “To tell you the truth, Jake, I want to feel you cum inside me. It’s been two and a half years since I felt a man do that!” Mrs. Roth kissed me. That was a first! We hadn’t done any kissing, except on each other’s bodies. “You should be cumming inside me or in my mouth every half hour,” she said softly. “Come on, fuck me and cum in me.” She kissed me again. “What position do you want to use? What feels the best to you?”
“I want us to be face to face. I want to look into your eyes when I cum.” Mrs. Roth moved to the middle of the bed and opened herself to me. I rested her legs on my shoulders and she guided me in.
“Don’t worry about me,” she whispered. “This is all for you. Cum for me you blackmailing son-of-a-bitch!”
I started pumping her slowly, sped up until I was fucking her hard and then slowed down.
“I’m going to cum. Look into my eyes. See how good this is for me. So fucking good!” I came so hard that I couldn’t hold myself up any longer. I collapsed, thrusting into Mrs. Roth, feeling my seed fill her.
Mrs. Roth bucked against me and came. “Ah, I love that feeling! Ummm, so good, so warm!”
I fucked Mrs. Roth’s cum-slick pussy slowly, savoring the feeling as I gradually softened.
“See? You should have done that twenty minutes ago. If you had, you’d be hard again by now and we’d be fucking. You’d be thinking about cumming again.”