The Education of a Cuckold Read online

  “Brace yourself,” she whispered grimly.

  I looked through the opening and saw Beth kneeling down about twenty feet away. She was sucking on the biggest cock I had ever seen. I hadn’t seen that many erect cocks, probably just my own and a few in pornos. This one was bigger, and it was black. With hindsight I realize now it was hardly a gargantuan penis, but it was the biggest I had seen. Beth was stroking it with both hands. No, she wasn’t just stroking it; she was sucking on it with abandon. Her hips were rotating as she kneeled, almost like she was in heat. Her gorgeous naked ass was moving around everywhere, as if in search of an invisible cock to fill it immediately.

  I felt a piercing betrayal unlike any I had known, albeit an irrational one. After all, Beth had never promised me anything romantically or sexually other than a tentative kiss I naively took as a promise.

  “That’s a big cock, isn’t it?” Jamie whispered into my ear.

  “Beth’s been fucking it for the last two hours at least. If you’d come in earlier, you would have heard her screams in your guest room.”

  Kneeling on the carpet squares in front of the sofa, Beth was saying something to the guy and staring up at him in admiration—a different kind of admiration than she had accorded me.

  I heard the guy laugh as he reached for his pants, fished out a fresh condom, and handed it to Beth, who unwrapped it.

  “That’s Billy,” Jamie said. “Billy and I used to date. I got him and Beth introduced earlier this summer, and she’s been thanking me ever since.”

  I was speechless.

  Jamie continued, “She begged me to stay up late tonight so if you got home early you wouldn’t run into them. She knows she should have waited until you left town, but she just couldn’t wait. She really needed to fuck.”

  As if on cue, Beth was rolling the condom over Billy’s penis. It looked like she was struggling to stretch it over the thickness. Once the condom was pushed up pretty far, Beth did something that really surprised me. With some urgency, she moved over to the edge of the couch and stuck her “best in school” ass in the air, held her hips up to him, and begged Billy to fuck her.

  Billy eased his big penis inside her, clearly enjoying the sight of her round ass begging for him like that. I was assuming it would be difficult for a big cock like that to get inside an eighteen-year-old like Beth, but she didn’t appear to be having too much difficulty. She started making a happy meowing sound when he was just hallway in. All the same, Billy moved in and out slowly, letting her get used to the rhythm.

  “This is why I wanted you to come down here,” whispered Jamie. “The girls in our family—we all started having sex when we were pretty young, and we cover for each other.”

  I watched the action in an improbable trance, with this “out of my league” blond goddess behind me whispering in my ear. It was like I had been fast-forwarded and dropped in the middle of a terrifying horror movie. My ego was in shock.

  “I wanted you to see Beth like this, because you’ve been trying to get in her pants for what, a year I think, right?”

  I was glad Jamie couldn’t see my face, which flashed red.

  “Get this: Beth fucked Billy the first night they met.”

  Billy was moving in and out a little faster now, getting into a groove with his thrusting. It didn’t look to me like he was all the way in yet, maybe halfway. Recalling the scene now, I believe his big dick was probably about eight inches long, a perfect size for a standing doggy-style fuck. Plenty of length to move in and out without actually slipping out.

  “So you see,” Jamie snarled, “You really need to let Beth go, because it’s not working out. She’s not spreading for you.”

  I guess you can see now why I think Jamie would have been a natural with a bullwhip and a man crawling on his knees. She just knew.

  Jamie had been resting her right hand on a box near my head. She moved it down for a different angle and ended up brushing over the tent in my pants.

  “Oh, I see you enjoy the show,” she laughed in hushed whispers, rubbing her hand over my crotch. “I don’t blame you,” she cooed. “Watching Beth get it on is … pretty awesome.”

  She rubbed the outside of my pants in vague circles. I was all the way hard, straining against my zipper, feeling so out of control.

  Jamie gave me a squeeze through my pants. I felt a jolt of sensation as I watched Beth start to move her hips in circles, getting into a groove with Billy. My only sexual experiences up to this point had been awkward—fun, but awkward. Beth and Billy were nothing like awkward. They were completely in tune, like two well-practiced dance partners.

  Jamie worked my zipper, feeling her way into my boxers. From there she easily pulled me out through the opening; I could feel the breeze on my dick as she continued to stroke it.

  “Now, doesn’t that feel good?” Jamie whispered in my ear.

  But then came the words that changed everything:

  “Oh! Your little dick likes it! Likes watching my sister get fucked while I stroke it.”

  I had fooled around with five girls, had sex with a couple of them. No one had ever taken charge of me like this, and no one had ever called my dick small. It was humiliating.

  “I just knew you had a tiny dick,” Jamie hissed triumphantly. “Little-dicked guys are always chasing girls like my sister around, trying to be nice to her, calling her too much, buying her concert tickets …” That last one hurt, because I had bought Beth tickets to several concerts over the years, even when I couldn’t go with her.

  “And yeah, she talks to you for hours on the phone … but only after she’s been fucked.”

  “Watch her get fucked!” Jamie whispered more loudly as she stroked her fingers up and down my cock. I had stroked myself off plenty of times, but never felt this kind of sensation.

  As Jamie picked up her intensity, Beth and Billy did too. With a harsh thrust he pulled back both her arms and jammed his cock all the way up in her—no more half thrusts.

  “Oh wow!” You could hear Beth easily now. “Wow!”

  Billy was getting cockier with each thrust. “That’s what you wanted, isn’t it bitch?”

  “Oh god, yes!” Beth said with abandon. “That feels so good!” The few times I called Beth a bitch we had gotten into fights. But when Billy said it, she seemed to love it.

  “You ready to get your pussy fucked, you fucking slut?”

  “Oh please!” Beth begged. I had never seen her beg for anything, or let a guy talk to her like this. But she begged for more, looking back to spur him on with an expression on her face I will never forget. Because I had never seen that expression before. Regardless of all the secrets we had shared, there were some she wouldn’t share with me. And here she was, desperate to share them with Billy. No, rather, he took them from her.

  Billy pounded her savagely. I had never heard such obscene sounds, like she was being plunged from the inside, her ass slapping up against him. Her legs were trembling and he had to prop up her waist to keep her from collapsing.

  Like Billy, Jamie was feeling her power. “You like it, don’t you? You like me jerking your little cock while you watch my sister get fucked.”

  “Yes!” I said helplessly, strangely comfortable in Jamie’s power, though scared of what she might do to me.

  “A little surprised, aren’t you? Surprised she’d give up her pussy like that?”

  “Yeah,” I admitted, still in a trance, eyes riveted to the scene.

  “That’s what girls do. We’re can’t help ourselves with a guy like Billy. Look!”

  Beth was screaming and sweating. You could see her legs shaking from top to bottom, violently to the point where you might have thought she was having a seizure.

  “You like that, bitch?”

  “Oh god I love it, Billy! Your dick is so big!!”

  “You needed this fuck, didn’t you?” he said, slamming into her, seeming to know the exact speed she needed.

  “Oh god, yes, you fuck me so well!”
r />   Billy stopped thrusting, just holding her deep, pulling her impossibly gorgeous ass up against him. I realized he was doing it to absorb her spasms. It was amazing to watch her ass shake and cum all over his cock. She may have been shy about kissing me, but I had to accept she knew how to fuck. This was hardly her first time.

  “You wish you were him,” Jamie said sexily in my ear. “You wish you were him making her scream like that right now … Don’t you?”

  “Yes,” I said helplessly. She increased the pace of her stroking. I realized with some embarrassment I was going to cum soon; I couldn’t help myself. It was probably a miracle I had held on as long as I did.

  By now, Beth and Jamie had slowed their pace, and she was doing most of the work. He stood there with his hands behind his head, smiling like a bandit as she desperately pushed her ass up and onto him.

  “That’s it, my little slutgirl, come get this cock you love …” Billy taunted her. Beth just moaned and backed up.

  “You wish you could treat her like that … make her desperate to fuck you like that,” Jamie whispered savagely in my ear.”

  “Yes …” I said again, breathing more heavily. A diabolical, red hot sex thought was dawning on me, aided by Jamie’s stroking: much as I loved Beth, much as I adored her, I would have traded all that to make her feel the way she felt right now just once, to make her cum like she had with Billy … like she was cumming again, right now. Billy just stood there, relaxing, while Beth screamed and pushed her ass all over his cock. Without even doing any work, any thrusting, he had brought her to another orgasm, her beautiful ass shaking with happiness.

  Jamie could tell I was about to cum. “Don’t yell when you shoot. You don’t want her to know you’re up here, being such a dirty boy,” she whispered. Jamie was stroking me aggressively now. She had total control.

  “Squirt little dick, squirt!” And so, with the hands of Beth’s big sister clasped over my mouth, I squirted against a cardboard box while the girl I loved got her brains fucked out. How was this happening? I passed quickly from ecstasy to an unfamiliar shame. Beth stood up. I thought they were done, so I turned to leave, my post-orgasmic relief reminding me I had no business here.

  “Wait … they’re not done yet,” I heard Jamie whisper from behind as she continued to caress and stroke my balls. “He’s going to make her cum again, even harder. Just watch.” Jamie had figured out something I didn’t know … yet. When girls cum that hard, they usually have an even harder cum waiting.

  Beth was standing up against Billy, whispering in his ear and stroking his big cock. It halfway limp and running down her thigh, the condom still partly on. Watching her work her right hand up and down that arrogant shaft made me start to twitch again, but there was more. She wrapped her arms around him and starting kissing him, her hips smooshed up against his lanky strong body. He wasn’t muscle-bound or even lean like the swim guys, but there was something about him—a total confidence that unsettled me even from here.

  The passion of their embrace was startling. It was harder to watch this than the fucking had been. At least the fucking was impersonal; I could write it off as animalistic cravings. But this … this was intimate.

  “See, that’s how you make a girl love you,” Jamie said. And then she said something shocking that has cursed and haunted me ever since. “Once you own her pussy, her heart will follow.” She rubbed my balls gently, letting the words sink in. In less than a half hour, Jamie—on a six pack of beer—had utterly dismantled me. Afraid to go for the sexual jugular as guys like Billy did, I had conned myself into thinking I could “go sensitive,” take care of a girl emotionally. Win her heart, and her body would follow.

  But while you worked your game for a year, Billy owned her pussy the first night they met. Jamie’s nasty voice rang in my head. It was harsh, but it made my cock twitch.

  “Oh yeah,” Jamie cooed, “You really like this,” she said triumphantly. Crap, I was already hard again, already back into the scene. My whole “take the high road” romantic girl-chasing-game had been exposed as the desperate stalker-like charade I knew it was, deep down. And Jamie had always known. I could blame her for being mean, but was it mean to expose the farce behind my nice guy persona? Or was she doing the world a favor? In all the years since that improbable night, I have debated that question in my head. In that moment the debate was less important than the fallout; the consequences would be severe, but there was no time for that now. Beth pushed Billy back on the card table, leaning over and jacking his cock as it strained toward a full erection again. I could see her cooing nasty things to him but I couldn’t make out the words.

  Beth got up and pushed Billy onto the carpet, his cock sticking obscenely up in the air. She straightened out the condom so that it covered most of his cock again and eagerly mounted him. It was amazing to see his cock disappear inside her as her pussy strained to receive him. I was fascinated by a cock big enough to make it really difficult for a girl to sit down on it, and I wondered what that must feel like. I had only been inside a girl a few times and when she was riding me it was not at all difficult for her to get my cock inside her.

  “Oh that feels good,” Jamie said, as if responding to my thoughts. “That feels really good, having a man stretch you out like that. It’s nothing you would know about, is it?” She was working me back up to rock hard once again.

  Beth was done being quiet. “God I love your big black dick!” she goaded Billy, her back muscles rippling. As she started riding him hard, I could see the advantages of a longer cock: she could work her pussy all around his shaft without slipping out. Meanwhile, Billy could just relax, help her out with some casual thrusting. The one time I’d had sex in that position, I had struggled to stay inside the girl. Billy was giving Beth intense friction, and without much effort.

  This was a great position for Beth because she didn’t have to worry about controlling anything. Her weight provided a natural resistance. Each time she landed on him, she didn’t take him all the way in—only as much as her body weight could handle. It seemed like she was cumming almost continuously, trembling, losing control, letting Billy take over the thrusting when she needed a break, sweat dripping down her back. When they fucked hard, you could hear the nasty squelching noises of a very filled up pussy.

  Jamie seemed to sense me tensing up; she moved in for the kill. “You like watching Beth fuck, don’t you?” she teased, expertly stroking me while whispering in my ear. “Don’t you?!”

  “Yes …” I whispered helplessly, almost too loud. The girl I loved was getting seen to by an expert right in front of me, and I couldn’t have been more turned on. It hurt like hell watching her slipping away from me like that; it would sting even more later. But for now …

  “You love it; your little dick loves it!” Jamie whispered triumphantly. “Get used to it. Girls love fucking big dicks!” By way of illustration, Beth surged even higher on Billy’s cock, bouncing violently. Watching her move with such passion, with Jamie stroking me from behind, was just too much to take. I spurted helplessly in Jamie’s hand as I watched Beth scream and twitch and thrust like a madwoman.

  “That’s it,” Jamie said soothingly, cruelly. She leaned over me, her breasts landing comfortably on my back through her shirt while she looked over at my shoulder.

  Beth seemed to be done fucking for now. She lifted her ass up, forcing Billy’s cock out with a loud plop. Then she leaned over and kissed him, lovingly, soulfully. I hated that he knew how to be sweet to her afterwards. Savage, then sweet. That made the implications so much worse. She kissed him again, then laid herself down on his chest. He wrapped his arms around her and ran his fingers through her hair.

  Jamie pulled at me from behind. “We should get out of here. Now that they aren’t screwing they might hear us up here.”

  I zipped up and Jamie pulled me into the back hallway, pointing me toward the end of the hall. I found the door to the backyard and walked out through the wooden gate. I wouldn’t return u
ntil well after midnight.

  Chapter 3

  I spent most of the night walking around, head full of crazy thoughts about what I had just seen. When I came back, all the lights were out. I made my way to bed through the glow of the moon.

  What happened the next day is hard to write about, even today, though I have masturbated while recalling the incident many times. When I manage to focus in on the sex, the emotional violence fades.

  I slept in, hoping that Jamie would have gone to work and maybe Beth as well. I lay in bed, thinking about finding somewhere else to crash. I was torn between getting the hell out and unspeakable desires. I guess I hoped it was just a terrible wet dream. I think that was fair, given I have never experienced a scene like that in all the years since, even when I looked for it.

  I still could not believe the sexual screams from this girl I had put on a pedestal. I started stroking again. Then: a knock on the door. It was Jamie and Beth. Beth was wearing these tight cutoffs she sometimes tortured the world with, along with an old Ramones t-shirt. Jamie had on a sundress that clung dangerously to her body. It was a lot of estrogen for anyone, much less a guy stroking himself under the covers. I quickly moved my hands away before they came in, hoping they wouldn’t make the connection, though my cock twitching under the covers wasn’t a big help.

  Beth had a strange look on her face. Jamie meanwhile looked like she had more evil plans in store. I sat up in the bed, suddenly vulnerable.

  “Jason,” Jamie said, “do you have something to tell Beth?”

  “About what”? I asked, worried about where she was going with this.

  “About … last night.”

  I didn’t know what to say. Everything seemed to be happening in slow motion.

  “Is it true?” Beth asked. “Did you really, you know, watch me?”

  I was taken off guard.

  “Yes,” I said with some resignation. So this was Jamie’s end game. She had twisted her particular knife perfectly.