The Education of a Cuckold

by Alex Hathaway

  Then something happened that has never happened before or since. I started to squirt. Without any contact from my hand or anyone else’s. Just cumming … onto her back and shoulder and neck. I expected Kristen to freak out but she was too distracted by the remaining burst of her orgasms.

  She panted and sighed for a couple of minutes, letting that huge orgasm seep out of her body but never raising herself off his dick. I heard her giggle and motion me around to her left side.

  Then she took a good look at me.

  “Did your tiny dick squirt all over me?” she asked, giggling.

  “Yeah.” I could only confess. But I added quickly, “I wasn’t even touching it!”

  “Wait … you mean you came on me without even stroking?”

  “Yeah.”

  “Wow. You must really love watching me fuck!”

  “Yeah.” I was getting better at responding to her promptly. She seemed pleased.

  “Grab your shirt and clean me up!” she demanded.

  I grabbed the shirt off the Nautilus rack. I’m not sure why I didn’t get a towel from the towel bin, but for some reason it seemed right to use my shirt for this. Like the dirty boy you are, her voice rang out in my head.

  I lovingly cleaned the cum off her back.

  Jim had propped himself up on his right elbows, watching us like we were on a late night cable movie you probably shouldn’t be watching.

  “You really do love watching me fuck and cum, don’t you?”

  “Yes,” I said again.

  She made a hum of approval.

  “Well, here’s another great thing about Jim’s big cock. He’s not even hard anymore, and he’s still up inside me, giving me pleasure.” Kristen rotated a bit on his cock.

  “See that?” Kristen said.

  “Yeah,” I said.

  “You had trouble staying inside of me even when you were hard, didn’t you?”

  I nodded.

  “You’d have no chance if you were soft, would you?” she pressed.

  “No.” I admitted.

  “But then again, you’re not soft now, are you?” she said, smiling up.

  It was true. Something about this scene … I couldn’t stop looking at her fuck. My dick was ready for more, in record time.

  With that, she stepped off Jim’s cock and beckoned for him to stand across from me, angling us both toward her.

  “Let’s see who cums first,” Kristen said wickedly. Ugh, I could almost sense the pending humiliation. But I knew she wasn’t doing this out of curiosity; she was doing this for me. She knew exactly how to get me off. It was one of the things that convinced me I loved her—in that forbidden way cuckolds know so intimately.

  Even though I had already cum once, I didn’t see myself lasting long in this scenario. And that’s exactly what she had in mind. She carefully peeled the condom off Jim’s cock and tossed it aside, looking at his big hanging dick in appreciation.

  She put a hand on each of our cocks and started working them, sliding up and down.

  Just like the time in college with Zach, the difference was striking. Jim’s cock was almost bigger than her grip and she had to move her arm up and back to cover the distance.

  “I only need a couple fingers for yours,” Kristen said, smiling at me.

  Ugh. But my cock twitched hard.

  “It’s amazing,” Kristen said, pulling us a bit closer together. “It’s almost like you’re two different genders. Or,” she added, looking up at me cruelly. “You’re the boy, and he’s … the man,” she stroked us harder, “the man who gets to fuck my pussy … anytime he wants.” She looked up at him with utter devotion.

  “And you, Jason, you only got to fuck my pussy once, and that was to teach you a lesson.” She looked up at me sternly, as if scolding me for even attempting to fuck her. That was it for me. I started spurting all over this goddess of a woman who had put me in my place.

  “Tiny dicks cum first!” Kristen said, laughing. “Your tiny dick just squirted!” Jim forgot to be polite and started laughing his ass off too. He seemed so proud of his sexual advantage and what it did for him. I knew I was beet red. I wasn’t sure if she was going to laugh again. Now she almost looked disgusted.

  She immediately turned her attention to Jim’s cock, working both hands up and down on it. I started backing away, thinking this was a good time for me to exit. But Kristen had other ideas.

  “Oh no you don’t, little boy,” she said to me. “I want you to see this.”

  I stood there dutifully as she proceeded to wank him off with both hands, faster and faster.

  I thought surely he would cum with that kind of intense rubbing, but no, he held out, moaning, eyes closed, enjoying the sensation. For another five minutes she worked both hands furiously up and down his cock, aggressively trying to make it cum. But it didn’t. His cock was dripping pre-cum the whole time, so she would wipe the cum from his mushroom head and lube the rest of his cock with it. Soon he was wet and slick and shiny.

  “God it’s so hard to make you cum!!” she said, working him faster. “That really turns me on, you know that?” She glanced over at me to compare us. Then she went back to her intense jerking motions.

  “Jeezus that’s a big fucking cock! So full of cum!!!” Kristen said. “I can’t believe how well you fuck!”

  Not even Jim was immune to such teasing talk. I thought I could see his dick twitching.

  With some authority, Kristen kneeled in front of Jim. She was back in sexual control again, no longer in his thrall. She reached her left hand under his dangling, heavy balls while continuing to stroke his cock with her right hand.

  “Oh!” Jim groaned. Kristen seemed to recognize the moment.

  “Look at this,” Kristen said, nodding me closer. “That’s it, baby,” she said to Jim. “Show him how a real man cums.” That one hurt.

  “Oh!!” Jim said.

  “That’s it,” Kristen said. Jim spurted a couple of times.

  “Oh!” he said again. And that was it.

  I was relieved. He had managed just a few small spurts, even more half-hearted than mine, which at least had landed on Kristen’s tits.

  As if reading my thoughts, Kristen said to me, “Keep watching.”

  Her stroking and rubbing was too much for Jim. Suddenly rope after rope of thick cum came spurting out of his cock, each one more vigorous than the last.

  I thought Kristen would think it was gross, but it seemed to really turn her on. Jim’s ass clenched as he kept on cumming. I couldn’t really count the ropes of cum, but it went on for a long time, with Kristen laughing and squealing as cum sprayed all over her face and tits.

  “Damn!” she said when it was over.

  “Get me something to clean myself up!” she demanded—of me, not Jim.

  I went over to the towel rack, grabbed a hand towel, and handed it to her. I felt shy now, wanting to cover up. My cock was soft and small. Jim’s still hung down aggressively, still half-hard. It was hard to blame him. Kristen looked almost better in her sweaty animal state that she did all dolled up.

  “I think … I think I should go,” I said. Ready to get out of here, resenting my kinky side and how it got me into so many emasculating situations.

  “Okay,” Kristen said, looking at me with kindness for the first time. As we locked eyes, I could see both her affection for me and the limits of that affection. It wasn’t the true love I craved, far from it. But it was a look free of bullshit, and that meant a lot.

  “I don’t think he should leave just yet,” Jim said, looking over at me with a different kind of look. As though he understood me better than I did myself.

  Jim took Kristen’s arm aggressively and guided her body to the ground. With intense aggression, he was on top of her.

  “Spread your legs for me, bitch!” he said, totally in command again.

  “No!” Kristen said. “No! I don’t think Jason should see this.”

  “Oh, I think he should … and you’re gonna sp
read your slutty legs for this cock!”

  Unable to help herself, she spread her legs wide. They were splayed out in both directions, feet poking into the sky.

  Why hadn’t she wanted me to see this?

  There wasn’t much gentleness to this fuck. Jim took a minute for her to get used to his fat mushroom head but then he was thrusting into her, hard.

  “Oh yes!!” Kristen cried.

  “Your pussy has some more cum for me, doesn’t it?”

  “Oh god yes!!” she screamed, so loud I instinctively looked around, but no one was anywhere near. She grabbed his ass, pulling him deeper inside. He was pushing in and out with intense power. I couldn’t believe how far he could thrust inside her.

  “Oh!” she kept calling as he hit bottom.

  “Who’s my slut?”

  “I am!” she called out.

  “Who’s your slut that needs to cum?”

  “I AM!!” she screamed again. “I’m your fucking slut!”

  “Who owns this pussy?!” he called out as he slammed into her.

  “Oh god, you do, Jim! ONLY YOU!!”

  With that, I could see her body trembling and wracking underneath him, almost as if she were having a seizure. He was pushing her hands down and just letting her pussy spasm all over him. Only it wasn’t just her pussy, it was a full body spasm.

  I thought she was dying. Maybe a part of her was. “Oh fuuuuck!!” she cried out.

  I realized I had cum again, stroking unconsciously to this amazing fuck. It almost hurt that time, but I was helpless not to. It was almost a dry cum; only a couple of drops came out.

  After that orgasm, he stayed inside her. She casually wrapped her legs around his back, pushing him in and out slowly, making happy mewing noises almost like a cat.

  It was then that I realized the scene had shifted. They were no longer fucking like animals whose bodies were perfect for each other. They were making love. She was kissing him, whispering to him. I thought I even heard her weeping.

  I suddenly realized why she didn’t want me there. Maybe because she knew that would hurt me more than all the small penis teasing.

  I wrapped a towel around me and walked out. I thought I could hear her calling out to me. Maybe I was dreaming it or just irrationally hoping for something that couldn’t be. I had to fight my own tears as I zipped up my pants and left. I thought about vowing never to see her again but I had been down that road before. I felt trapped.

  Chapter 12

  The days that followed were as brutal as you would expect. I kept waiting for Kristen to call, hating that she didn’t, knowing that I would eventually call her, and hating that she knew it.

  The time with Kristen had damaged my sexual confidence even more. If she cared about me, then why had she done that? Whenever I met compelling girls my own age, my awareness of my own inadequacy ruled out any romantic approaches. And yet Kristen had given me some of the best orgasms of my life. Of that, there was no doubt. Didn’t that count for something? If it hadn’t been for her, my only orgasms during that time would have been by my own hand, nothing like the body draining ones she could pull out of me. But should you spend your life chasing orgasms, or does that just make you an addict?

  A week went by, and still no call from her. On Saturday, I biked to the park and played ultimate Frisbee with my pals. I felt athletic, confident, a normal red blooded American male—free of my fetishes and insecurities. Out drinking after the game, I could feel the comfort in my own skin returning. The only problem was interacting with a few of the girls that were there. They were cute and hot and funny and smart. I could sense they wouldn’t begin to understand or accept my desires. When they joked at chatted at me, it was like they were looking right through me. I couldn’t figure out how to reclaim the cocky persona that would draw them to me.

  Alone in my own bed, I felt my mind wander back to Kristen. The taboo and naughty things we had done. How much she had aroused me. The buttons she knew how to push. But more than that: how she had put me in my sexual place. And how much I had loved that. No, I didn’t just love her interaction with me; it gave me relief, as if the charade of being someone else was over. And yet I felt shattered inside. If women arrived at romantic intimacy via sexual ecstasy, where did that leave me? Where did she leave me? What about building me up on the other side of tearing me down? What happened to that?

  On Sunday, I knew I was going to call her. I could rationalize it by saying I was continuing my therapy, but I knew the truth: I wanted to cum that hard again. Well, and one other thing: I wanted to be seen and truly known—for all my inadequacies. If some humiliation was the price of not pretending around a girl, I would happily pay that price.

  She was home when I called.

  “I was waiting for your call,” she said happily.

  “I wasn’t sure if I was going to call or not,” I said, trying to sound more indifferent than I felt. My heart was pounding.

  “Well, I’m glad you did … because I’m not quite done with you.”

  I didn’t know how to take that.

  “We’re not finished with you yet … I put you through something pretty rough, but there’s more to do.”

  “What?” I asked, filled with curiosity and dread.

  “Well, I’ll let that be a surprise … but I think you want to see this one through.”

  No hope restraining myself. Two days later, I was there. She was wearing an impossible little green sundress, one that she cut from a longer dress. The frayed edges lingered on her muscular thighs, as if her body was asking me if it was worthy. We both knew the answer to that.

  I walked to the massage room, but she stopped me.

  “Let’s talk in the living room for a while,” she said.

  She saw my look.

  “My roommate said she would be gone most of the day, and with the sun coming in, it feels good out here.”

  She sat across from me in a futon chair. I sat on the couch. The sun lit up her face. I couldn’t help wondering if she was wearing anything under the sundress.

  “So …” she said.

  “So …”

  “It was kind of a rough time for you when we last met up, I bet.”

  “Yeah.”

  “Sorry,” she said. “I knew that would hurt, but there’s a reason for it …”

  I wasn’t quite sure of the reason. All I knew was that I was desperately drawn to her and what she did for me.

  She looked at me demandingly. It was amazing how easily she could shift from friendly affection to total control.

  “What will you remember most?” she asked. “Be honest.”

  It took me a minute to answer, but then I said, “Watching you cum so hard. It was … beautiful.”

  “What else did you like?” she asked.

  No more hesitating, I thought, just brutal honesty.

  “I liked it when he took you from behind and made you scream and yell that you were a slut for his cock.”

  “Oh you liked that, huh?” she smiled, but in a stern way, expecting me to treat her secrets as such.

  “Yeah.”

  “You like talking about it with me now, don’t you?” she asked.

  “Yeah.”

  “Here’s what I want to do, Jason,” she said. “I want to take your little dick out now and stroke it while you tell me all about what you saw.”

  “But your roommate …”

  “Well, she shouldn’t be back anytime soon. And if she does come in, well, you need to be free enough to let it happen, let whatever it is happen. No more shame.”

  I was beyond obedience at this point. I was either chasing my fetish or chasing the truth, tomorrow be damned either way. I reached inside, pulled my already hard dick out, and started stroking.

  “That’s it,” she said, “but I don’t want you to cum right away. Stroke it, bring yourself to the edge, stroke a bit slower. But don’t cum.” After watching me follow her instructions, she said, “Yes, good. Now, tell me all about what yo
u saw.”

  And I did. As I stroked, I told her what it was like to watch her fuck. How intense it was to watch. What it was like to see her cum that hard, her whole body shaking. Especially since I had failed to make her feel the same way. I didn’t tell her how much it hurt. That was the one part I kept to myself and maybe the one part she didn’t need to be told.

  Each time I was close to cumming, I would hold back, releasing the tension while she guided me through it. My balls and cock ached from not cumming, but I held on.

  She could tell I was close. She got up and sat down next to me.

  We both had our legs up on the table. I could feel the scrape of stubble on her brown calves. I almost shot just from that sensation. She moved my hands off my cock. It was standing straight up, red and hard and dripping with precum.

  “So, you did good. You held out for a really long time.”

  “Yeah, maybe for not much longer.”

  “That’s okay,” she said. “You need to be able to hold out. This will help you in some sexual situations. I want you to keep practicing, keep going right on the edge and coming back.”

  “Okay,” I said.

  “This is different than jacking off at home. The desire to cum is way more intense, right? With me watching, I mean.” She looked at my wickedly and down at my cock as well. I almost shot again.

  “Yes.”

  “That’s right,” she said. “It’s like it would be in a real sexual situation. And, inside a sexy woman’s pussy, you don’t want to squirt right away, now do you?”

  “No.”

  “Are you ready to cum now? Shall I release you?”

  “Yes!” I said, ashamed of my eagerness. I could tell from her quick smile how pleased she was. Yeah, she pretty much owned me. After all the indignities, somehow I trusted her. Because she’s the only woman who has been one hundred percent honest with you …

  She wrapped her hand around my dick, squeezing it softly.

  “Ohhhhhh!” I exhaled.

  “So you understand now, right?” she said.

  “Yes,” I said.

  “You understand why my pussy needs a big cock, right?”

  “Yeah …”

  “It’s not because I’m loose down there. You’ve had your fingers in, and you know it’s plenty tight.”