The Education of a Cuckold

by Alex Hathaway

  Little by little, that soft cock got hard in her hands. To my surprise, it didn’t get much longer, but it sure as heck got harder. And thick. Kristen was spitting on it, rubbing it quickly. To be honest I was surprised Jim didn’t cum. I thought I saw him moan in pre-orgasm a couple of times, but he steadied himself on a Nautilus handle and she kept on working his dick, his ill-fitting white t-shirt still in place, his sweatpants around his legs.

  I had not seen an uncircumcised dick before. Kristen seemed to love messing with the head of it and working it back and forth.

  It had been a long time since I’d had the chance to watch a girl have sex in front of me. I was feeling a little weak in the knees at the prospect. I sat down on a bench near the bench press.

  I was chagrined, hoping that he would have trouble getting as hard as me, but no: his cock was not only hard, but it even pointed upward a bit, despite the weight. It looked pretty goddamn intimidating. Maybe to her, too?

  “Jim, I need to get fucked,” Kristen said. I don’t think I’ve ever seen a girl strip so fast. Kristen slipped out of her leotard in one quick movement and pulled her tights off so aggressively I thought they might rip.

  Jim kicked off his shoes and shrugged out of his shirt as well. It was weird to watch his transformation from big awkward oaf to “man in charge.” His cock jutted outward with authority—way more Mr. Big than George Costanza now.

  “Come here,” Jim called out to her, and she approached, obediently, putting his arms around her waist. “You’re not ready for this big cock yet,” he said to her in his gravelly voice.

  “Oh yes I am. I want it!” said Kristen.

  “We have to get you wetter first,” he said. With that, he started working a couple of his fingers inside her pussy. The look on her face was a jolt, like a light socket being switched on.

  “Oh god,” Kristen said. “Oh god.”

  It seemed like she had even forgotten I was here, rubbing my cock through my pants. No one cared what I did, at least for now.

  Kristen had grabbed Jim’s cock in her left hand and was stroking it, or attempting to, while she alternately thrust into and away from his hands, as if the pleasure was too intense.

  “God you know how to work me,” she cooed. Then she surprised me by quickly pulling him to her and kissing him hard.

  It was tough to watch that kiss. It wasn’t the rough quickie I was hoping for, but a real soulful kiss that made me feel more like I was watching a couple on their wedding night.

  God I wanted that kiss to end.

  After what seemed like a damned eternity, he finally pulled his mouth away from hers. But they stayed in a close embrace.

  “Oh god, I can feel your huge cock all up against my belly!” Kristen said, pulling him even closer with her strong arms around his back.

  “Yeah, that feels good to me too, Kristen,” Jim said seductively. “Just think how good it’s going to feel all up inside you.”

  “Oh god!” Kristen said. It seemed like she was thrusting up into him. No way could she take his cock from that angle, but she was clearly pushing her pussy right up onto it.

  “Oh yeah, you’re wet enough now,” Jim said. “Look!”

  And with that he stepped back. Even from ten feet away I could see the pussy juice running down her legs. His cock was also glistening, maybe not any longer but as hard as I had ever seen a cock. Damn that dick was thick. I couldn’t imagine a girl taking it without serious pain.

  But Kristen didn’t seem to care. She went over and leaned against a Nautilus shoulder press bench, bracing herself against the cushion. With the other hand, she opened up her pussy and leaned back, humping her ass in the air. Then something unexpected happened. She actually remembered I was there.

  “Come closer!” she ordered. I sat down on a weight bench about eight feet away, but with a better side angle, where I would really be able to see them.

  “No, Jason, pull the bench closer!” Kristen said. It was intense to hear her say my name in the middle of this. In a really bizarre way, I felt like I mattered to her. That I was being included. That I was lucky she was sharing this with me. From the first time I had seen her bedroom, I’d had horribly wicked dreams about what she got up to in there. I was about to find out.

  “Now, Jim!” She glared at him. He knew exactly what to do, moving in on her quickly.

  “Watch closely, Jason!” she told me.

  I suddenly realized the significance of this scene. She was setting herself up to get fucked in the exact same position that we had tried and failed at a month before. Jim leaned over her and she moved her hips wantonly. I heard a loud “plop” as his uncut mushroom head popped into her. I suddenly realized she had not made him wear a condom. If I was her boyfriend, I would have protested. But I was not. Not even close.

  “Wow!” she said. She tried to pull back instinctively, but before she could, he inserted another couple inches of cock inside her, keeping her impaled as he pulled her ass back toward him.

  “Wow!” she said.

  Slowly but surely, careful not to thrust too hard and give her too much length, he started moving a few inches in and out of her.

  “Damnnnnnn,” she said.

  “You’re really tight tonight, baby,” he said in her ear. She smiled and looked back at him.

  “It’s because I haven’t had your big dick inside me for three days,” she said, with a petulant look on her face.

  “I’ll make it up to you tonight, okay, sweetie?” he said softly, giving her a brief kiss.

  “Yeahhhh,” she said.

  Jim increased the pace of his thrusts, still just a few inches in and out, in and out. I found myself amazed she could take even that much, but then I remembered how wet she was.

  “Ohhhhh,” Kristen said, and I could see her pussy lips clinging to his cock outside her body on each thrust. I realized what Jim’s physical advantage was. In this position, he could work a few inches inside her, getting her warmed up, with almost no risk of falling out or interrupting the rhythm. What would that do to her?

  “You’re such a slut,” he teased.

  “No I’m not!” she objected. “I’m just a girl who gets what she wants.”

  “No, you’re a slut for my cock, and I’ll prove it to you.”

  With that, he rammed himself almost all the way inside her and grabbed her shoulders.

  “I’m fucking you now …” he said, and he meant it.

  He started moving in and out with determination, not slamming her, but leaving about an inch outside on each thrust.

  As I rubbed myself—now totally hard under my own pants—I could see Jim was at no risk of falling out even as Kristen moved her ass around. The best part, for her anyway, was that at least a few inches of his dick were in her pussy at all times, even as he pulled out. That must feel amazing to her, I thought.

  As if reading my mind, she said, “Oh baby, that feels so amazing.”

  It was awesome to watch her push that muscular back in the air and know she was getting exactly what she craved, even if it wasn’t from me.

  As for Jim, he appeared to be in no rush, just moving in and out of her strongly, but with no real urgency.

  “Oh Jim, if you keep doing that, you’re gonna make my pussy cum!” Kristen said.

  I looked more closely; I thought I could see the beginnings of a tremble or a ripple in her body as she moved.

  It must be incredible, I thought, letting yourself go into an orgasm. If the guy just keeps it up, your pleasure is inevitable.

  “Oh, you ain’t seen nothing yet,” Jim said.

  “Ohhhhhhh, she groaned as he thrust a little harder but still in rhythm.

  “That’s it,” Kristen said. “I’m cumming!” And she did. I could see her body shake and tremble as he pulled her ass back into him, keeping his cock buried inside her while her orgasms rippled through. Without even realizing it, I had pulled my own hard cock out of my zipper, stroking openly. Neither one of them had even noticed.


  “Oh baby, that was so good,” Kristen said, reaching back to brush his face and hair sweetly.

  They were still fucking, but very slowly, tenderly even. As Kristen caught her breath, she looked over at me.

  “Did you see that?” she said. I nodded.

  “I see you liked it,” she said. I stopped suddenly, ashamed, perhaps flashing back to the time I’d peeped on Beth.

  “No, don’t stop, Jason,” Kristen said. “I want you to stroke your little dick while you watch me fuck.” I thought I heard Jim laugh quietly.

  “You know why I wanted you to see this,” Kristen said.

  I nodded.

  “So stroke it,” she said. “Make it feel good.”

  Jim pulled his dick out of her, and her pussy exhaled with a loud obscene plop that made them both laugh again. He grabbed her hand and walked her over the side of a leg press. He placed both her hands at the top of the press and stood behind her, adjusting her ass outward. Without waiting for permission, he started easing his cock back inside her. I was amazed at how easy it was for him to insert his cock in this “standing up” position. When Kristen and I had tried that position, it had been a physical impossibility. I felt a surge of inadequacy and excitement, watching him bend her head down as she willingly complied.

  “Hey, Jason …” It was the first time Jim had spoken to me directly. “Do you want to see Kristen act like a total slut?”

  “Hey!” Kristen said, looking back at him, faux-angry.

  “You want to see what a dirty fucking whore she really is?”

  “Jim!” Kristen said, trying to pull away from him, but he was holding his cock inside her and her smaller body was pressed up against him. She had nowhere to go … not that she really wanted to.

  “Yeah,” I said without further hesitation.

  “Jason!” Kristen said to me in that mock angry tone that you didn’t want to hear from her, in case real anger was around the corner.

  “Okay, you asked for it,” Jim said. With that, he slammed his cock inside her.

  The next ten minutes are difficult to describe. It all happened so fast, with such mesmerizing intensity. What I can tell you is that I’ve never seen anyone get fucked so hard.

  Turns out the first standing position was more like foreplay. This was the real thing. Jim was slamming his cock inside her continuously. Her pussy was making crazy slushing sounds as her ass slapped up against his cock. He had her mostly by the shoulders, pulling her into him. It looked to me like she was coming continuously, bucking her ass all over the place. I envied his big cock. With my small one, there was no hope I could have kept it inside her while she was wildly bucking around like that. I don’t think the air was on in the gym after hours. Her hair was caked to her face and her back was glistening with sweat.

  Yeah, she looked pretty much like a slut. Of course for me that meant she looked beautiful, perfect. It was like they were born to please each other.

  Then a surprise: Jim took his cock out of her and slapped it a few times on her ass. It was amazing to see how much noise his big cock could make, all red and shiny and slick with her cum. It sounded like he was whopping her back with a paddle.

  “Oh, why’d you take it out?” she whined, bucking her ass in an effort to find his cock. “I was just about to cum …”

  Had she really said ‘just about to cum’? Then what was the body shaking she had been doing for the last few minutes?

  “Because if you want this, you have to beg for it.”

  “Oh pleeeeeease …” Kristen said, pushing her ass back up at him, “Please put it back inside me.”

  “Are you my slut?” he demanded.

  “Oh god, yes!” she said.

  “Tell Jason you’re my slut. Tell him you’re a slut for my big dick!”

  “Jason, yes,” she said, “sorry, but I just can’t help it. I’m such a fucking slut for his big cock!”

  That seemed to satisfy Jim. As he inserted his cock back inside her, she made happy moaning sounds. Her breasts swayed underneath her. As much as I wanted her to myself and felt the surge of jealousy to prove it, there was no denying that I loved watching her being conquered like this, all her brashness reduced to submission.

  Jim grabbed her hair roughly and just started pounding her. “Fuck me back!” he commanded.

  And she did, pushing her ass back on him whenever he pulled too far away. She quickly pulled a bench over to brace her legs up so she could steady herself, bending her knees as needed.

  “Oh fuck me!” she yelled. “Just fuck me!!!”

  Jim was working it. I couldn’t believe he was able to fuck so long without coming.

  “Cum for me,” Jim said. “Get what you need!”

  He slowed his thrusts but they didn’t miss a beat. She was pushing back at him so hard and screaming and yelling and I could see her body shaking from her ass up to her head.

  “Oh god, yeah, I’m gonna FUCKING CUM SO FUCKING HARD!! GOD, YOUR COCK IS SO FUCKING BIG!! OH MY GOOOODDD!!!

  I could understand now why she wanted a private space. It sounded like she was screaming for her life. But as I can attest, it was not agony but its flip side, rapture.

  At just the right time, Jim reached down to Kristen’s legs and pulled her to him. Her whole body trembled and shook for what seemed like a minute. Spit even fell from her chin as she gasped for breath.

  “Oh yeah, baby, your pussy’s gonna squirt!”

  “Oh fuck, IT IS!!” she screamed.

  With a loud squish, Jim’s cock was out of Kristen’s pussy as if she’d expelled it. Expertly, Jim reached between Kristen’s legs and worked her pussy lips, as if to empty them, and while Kristen held her hips up, I could see spurts of her fluid surging out of her pussy onto Jim’s hand, onto the ground, everywhere.

  “We got a squirter!!” Jim called over to me triumphantly, claiming it like he would a trophy. Clearly he had seen this kind of thing before. I had never seen a pussy squirt at all, much less jets of fluid the way a cock did.

  “Now we’re gonna fuck!” Jim said, moving Kristen gently off him and lying down on the bench. She straddled him and lowered himself down, inch by inch, totally focused on her primal urge. I was fascinated by how her pussy lips extended and gripped his thick cock, struggling to accommodate him before finally working most of it in. Her happy sighs told me all I needed to know about how that kind of fullness must have felt. They fucked for a few minutes that way before Jim sat up and, without pulling his cock out, stood and started bouncing her around on him.

  “Let me give you a good view, Jason,” Jim said generously, walking a few steps as she held onto his shoulders. When her back was a few feet in front of me, he raised her up and down, and you could see again what an advantage his long dick had. He moved her up and down and never came close to flopping out. From this angle, her weight could slam into him, taking him deeply but not deeper than she could handle. The advantage of his thickness was undeniable as well; you could hear the loud plunging sounds caused by so much deep friction.

  It was inevitable she would cum with that kind of fucking, and cum she did, shaking and trembling and sweating while he held her tight, letting her get all the cum out of her body.

  It may sound crazy, but I felt a debt of gratitude to him. I was so happy to see her so blissful. You have to understand. I knew her struggles, her hard times growing up, some of her ups and downs in her personal life. She might have been a force in the world but it didn’t mean her life had been easy. She needed this. She deserved it. When Jim released her, she stood on wobbly legs, propping herself against him. Kristen looked so relieved and so … fucked out.

  But Jim wanted to show me a little more. He seemed to understand why I was here as much as she did. He sat down again on the bench and guided Kristen to sit down on him, facing me. It was stunning to watch the look on her face as she sank down onto his dick. You could see even after all this sex that it still wasn’t easy for her to take him in.

  Kristen cont
rolled the action this time, riding slowly up and down on his cock, obviously a bit weary from the intense sex she had already received, enjoying a pleasurable but relaxing fuck. I realized she was now paying more attention to me. Smiling in a knowing way, kind of mean, as if I was lucky to be there. Maybe I was. She beckoned me over.

  “Come closer,” she motioned.

  I did.

  “Hold me up so I can really fuck him,” she demanded, motioning for me to stand behind her. I did as I was told.

  “My legs are too weak from fucking,” Kristen said. Then she tilted her chin upward and smiled firmly at me. “Help me move up and down on his huge cock so I can cum again.”

  I had never felt anything quite so humiliating … or erotic. I braced her with my arms and started moving her up and down. It seemed to help, as she started fucking him faster, leaning a bit on my side but still angled well enough to fuck. I’m not sure I ever felt more certain of my sexual place. It was here. With her. Helping her cum so damn hard. Feeling her lean on me while she fucked, trusting me to hold her. It was one of the more intimate things I had ever done with a woman, and certainly the most taboo.

  Damn! I kept trying to pull her higher, higher than his dick could reach, but Jim expertly adjusted his thrusts to match. He seemed to be enjoying my efforts. I could see him grin over at me before he went back to thrusting.

  Thanks to my arm strength, Kristen was able to use what was left of her shaky leg muscles, rising up and letting her weight fall. Suddenly I felt a slight tremor go through her, then another.

  “Did you feel that?” She twisted and looked up at me with urgency.

  “Yeah!” I said. It was amazing to feel that vibration, like the first ripples of a massive earthquake.

  The earthquake hit. “Oh my god!!” Kristen said, sitting down on him and rocking her way through an orgasm. She held my hands down to prevent me from pulling her up while she shook all over. His dick was still entirely inside her. I was so happy for her, and unbelievably jealous. And hard as a fucking rock.