The Education of a Cuckold

by Alex Hathaway

  “The first time I met Lee,” she said, “our condom owner, “I felt a shock wave go up from my pussy, up through my body and out my nipples. I just knew what he could do to me.”

  “How did you know?” I asked her.

  “It was the way he looked at me,” she said. “It was as if he could see my pussy cumming all over his cock, whether or not I liked him. Like it was already decided he would one day get inside me and make me cum.”

  She was stroking; I was caressing her breasts, squeezing her nipples just like she showed me.

  “Two days later, I was flat on my back for him. His big cock was pounding into me, and my pussy was cumming all over it. I had a serious boyfriend at the time too, but I couldn’t help myself. I was lucky he had a big size condom with him, I wouldn’t have been able to stop myself from fucking him either way. He probably could have forced me out of my relationship and into his bed permanently if he had wanted.” Stroking me a bit more intensely, she added, “But you’re not like that.”

  “I’m not?” I asked, wanting but dreading her answer.

  “The first time you looked at me, I could tell how smart you were, how kind, how wise. But I could also tell I’d be able to conquer you easily. That I could have you whenever I wanted. And I was right, wasn’t I?” Another teasing smile.

  “Yes.” I had to admit it.

  “Deep down you’re not sure…” she said.

  “Sure?” I asked.

  “Not sure if you could really please me.”

  I was quiet.

  “Are you?”

  “No,” I admitted.

  “It’s good you feel that way,” she said. “Fucking my brains out … That’s not your job. That’s not a job your little dick could handle now is it? Not that you will ever find out,” she added firmly, locking eyes with me.

  With that last bit of brazen sexual truth I couldn’t take it anymore. I started bucking and cumming into the condom.

  “Uh–oh, you lost control!” she said, laughing with satisfaction.

  “Oh wow!” I said, spurting and spurting inside the condom. I felt like I came a ton. The orgasms welled up from some deep place only she had access to.

  “That’s it,” she said happily. “Empty that little dick for me.” She gripped it with her left hand while stroking my balls with her right. It felt amazing, but I was cleaned out, just a couple of drips left.

  “See, that’s really hot. You really turn me on when you do what you’re told,” she said. “Wanna see?”

  “Okay,” I said.

  She walked closer to my face, slid the jeans off her hips and her nude body came into focus. She had that devastating mix of athletic and curvy. If she had any insecurities about her body, she was perfectly clear about its power over me.

  She grabbed my right hand and pushed it toward her thighs with some urgency.

  “Get in there!” she said. “Get some fingers in my pussy and feel how fucking wet it is.”

  I reached under her panties and fit one, then two, then three fingers inside her, surrounded by wetness. “Damn!” she said. She had to lean one arm against the massage bed to keep her balance while I worked my fingers in and out.

  “See how wet I get?” she said?

  “Yes …”

  “Jerks who hit on me at bars can never make me wet like this, but a guy like you, who lets me put him in his place … hot damn!”

  I felt a flush of embarrassment but also realized my cock twitching to life again.

  “Of course, that’s nothing compared to how wet I get when”—she was speaking in fragments, as if in a dream—“take me over. Rip the orgasms right out of me!” she commanded, eyes closed, tits swaying. I could almost imagine her riding her lover in ecstasy, tits swaying happily over that lucky man’s face—his to touch anytime he wanted.

  But not for me. The pain was perfect in its truth.

  As if reading my mind, Kristen took my fingers out of her pussy and started putting her pants back on.

  “Dammit, I’m gonna be horny the rest of the day,” she said, “but it will be worth it.” She smiled.

  I started to clean up as well. Suddenly I wanted to leave.

  I got down from the table, putting my pants on quickly, not caring if I missed a belt loop.

  “Jason …” she started.

  “Yeah …”

  “You’re going to experience a lot of emotions after this session. You might even get angry with me. From here on out, the rules change. You make all the appointments, not me. And only when you’re ready.” She smiled as she put her tank top back on, with a kindness that shocked me given how brutally honest she had been.

  “Think of this as my gift to you and the other women in your life.”

  That line repeated in my head after I left, but the confusion only increased. A gift for the other women in my life? I had never felt more insecure about myself, never more inadequate. And I had to pay her for the privilege. How was this helping me?

  Chapter 10

  It was easy to hate Kristen a little bit, and so I did. I found myself whaling on the punching bag at the gym. I was so fucking pissed at her—hell, at all the women who had rejected me for reasons fair or unfair. I had been nothing but nice, decent, funny, attentive, everything women claimed they fucking wanted!

  I swore I would never call her. I felt even more certain of that vow a few days later after a couple more sessions on the punching bag. Who needed to live in a world of addiction and fetish? There had to be another way forward.

  A week went by. The horny memories faded; I hit the gym hard. Then, on Thursday morning before work, I saw a girl in the gym I hadn’t seen before. I’ve never been that attracted to “exercise mat” gym girls, but she was not that kind. She looked to be in her mid-twenties and had a black tattoo of a dragon snaking down her right arm. Her hair was short white blonde; the muscles in her arms and back rippled under her skin when she moved. She was half girl, half jungle cat, and she never went near the aerobics room. Yeah, I liked her.

  When she went over to the free weights and put twenty-five pounds on each side I kept an eye on her. She pumped out two reps no problem; then she started to slow. I watched her struggling with the last few repetitions, so I ran over, Mr. Helpful.

  “Need a spot?” Without waiting for an answer, I put my hands under the bar in case she needed it, but she didn’t. She extended her arms fully and racked the bar on her own. When she sat up and toweled her face, she smiled briefly. I was riveted. Later I made a point of walking over to her at the water cooler.

  “My name is Jason,” I said with my hand extended.

  “Hi Jason, I’m Lorrie.”

  She extended her hand and smiled again, but in a decisive way that made it clear she didn’t suffer any fools. I asked about her workout routine, how long she’d been coming to the gym.

  She interrupted me mid-sentence. “You know, Jason, I don’t do small talk. Let’s be clear … I’m not interested, okay?”

  I clammed up. She smiled kindly and said, “I’ll see you again, I’m sure,” before walking away.

  Never had I been shut down that efficiently. I felt my cheeks get hot and looked around the gym—casually, as if to survey the equipment, but also to see if anyone had seen me get slammed. Fortunately, it didn’t look like anyone had.

  The next day, I actually changed my routine in the hopes of not seeing her. Unfortunately she was there. This time she was being spotted by this muscular brown-skinned guy. His arms were pretty big, big enough to make me wonder if he was taking questionable supplements. I knew how hard it was to get to that point.

  I was hoping-hoping-HOPING they were just workout partners, but then I saw her bend down and peck him on the lips before grabbing her bag and heading to the locker room. He was shorter than her, so Lorrie had to lean into him. Her mystery man stuck around and lifted some more weights after she was gone, an impressive bench press of three forty-five pound plates on each side—far more reps than I could do. I coul
dn’t help but scan his crotch, wondering what he was giving her. I was relieved to see nothing out of the ordinary. It made me hopeful; maybe if I could bulk up and get in fantastic shape, she would find me as sexy as this guy.

  I moved on with my workout. Later, walking through the locker room, I ran into him again changing clothes. He was naked except for some kind of jock strap. Who wears jock straps when they work out? As he was peeling the strap off, a big soft cock flopped out. I didn’t want him to get the wrong idea, so I walked into the next section of lockers. He looked bigger soft than I was hard. Ugh. The clock on the wall caught my eye. I was about thirty minutes off on schedule. My damn watch must have stopped again. I would need to take a shower here.

  I stashed my stuff and walked to the shower. It was just me in the shower and one other older guy with his back to me. I dreaded the group showers here, but there was no time to go home. I soaped up quickly and rinsed, quickly moving to the shampoo and studying the cracks in the brick wall, trying hard not to look at the skinny old dude behind me or think about Lorrie’s boyfriend. I hoped like hell that he wouldn’t walk in while I was still showering.

  Luck wasn’t with me.

  “Holy shit that’s a big dick!” It was the older guy behind me. I knew he wasn’t talking to me.

  “You like it?” I took a quick glance to my right to see Lorrie’s boyfriend entering the showers and hanging his towel up. His dick seemed even a little bigger, maybe enjoying the attention.

  I looked away quickly, surprised this guy was so willing to talk to another man about his cock.

  “How big does it get?” the older guy asked.

  “It’s been measured at ten inches,” Lorrie’s boyfriend said proudly.

  I snuck another quick glance at him. I didn’t see ten inches but I did see something huge jutting off his body, poking this way and that as he turned the shower on.

  “I’d invite you to touch it, but I don’t think that’s allowed here,” Lorrie’s boyfriend said.

  I thought I heard the older man moan. Oh boy did I want the hell out of here! But I’d have to walk past both of them to do it, and I’d hung my towel on the other side of them to avoid getting it wet. Doh!

  I stared hard as ever at the crack that ran between the brown bricks above the shower head.

  “I’ll bet you’ve fucked a lot of girls with that big thing,” the older guy said.

  Lorrie’s boyfriend laughed. “I get plenty,” he said. “A couple of guys too.”

  I heard more panting from the older guy’s direction. I was afraid to look at him.

  “Once I fucked a guy’s girlfriend right in front of him, and then I fucked him!” Lorrie’s boyfriend said.

  I heard some weird slapping noise behind me so I took a quick glance over my left shoulder and saw that the older guy was spanking his own not-small cock.

  “Jeezus!” the old guy said. A quick glance to the right, and a view of Lorrie’s boyfriend soaping up his nearly-erect cock—by far the biggest I have seen before or since. Most of the cocks I have been impressed are firmly in the “big” category, but this one was enormous.

  I was out of there. I walked past them in a hurry clutching my towel, laughter chasing me from behind. It wasn’t till I wrapped the towel around me that I realized I was completely erect, which may have been the source of their laughter as they saw me getting the hell out of there but unable to deny … well, I don’t know.

  I went home with a lot on my mind. Here I was killing myself to work out, trying to become the kind of hot guy girls wanted. But I couldn’t seem to get the attention of the girls I was drawn to. Meantime a guy with a big swinging dick seemed to have no problem getting the sex he needed. My rebellion against Kristen suddenly felt like hot air. What other options did I have?

  For the first time all week, I thought about her. About how she seemed to have an appreciation for me, and yes—compassion. And I thought about how she teased me. And how much I liked it. Checkmate.

  “I knew you’d call,” she said, happy and cocky in that way I loved and hated.

  “Can I … make another appointment?”

  “Sure,” she said, “I’d love that.”

  The next afternoon, I was over at her place.

  Kristen opened the door dressed in an outfit that was an obvious attempt to torture me—cut-off jeans with a bandana for a belt, sweatshirt with the zipper mostly up and the sleeves cut off. The way her breasts seemed to move inside, I wasn’t sure if she had anything on underneath.

  She asked me to get ready on the table, no towel. “Lie on your back,” she called out. I knew the routine.

  As usual I tried like hell to stay calm after I undressed, but it was not to be. Just thinking about the swinging breasts under her sweatshirt was too much.

  I had to let it go. She knocked, came in, and immediately started laughing.

  “Oh! You’re already hard. You must really be looking forward to this appointment.” She gave me a stern smile.

  “Yeah,” I had to admit.

  She started with a conventional massage, kneading her way up my legs. As she approached my upper thighs, my cock twitched and hardened further.

  She reached for me. “I can never get over how much smaller this dick is than the ones I usually touch. It feels so different in my hand.” Her smile was teasing.

  “Oh,” I said helplessly, moaning with the pleasure. I knew I wouldn’t be able to hold out long, even with this casually stroking.

  “So … we’re going to have some fun today,” Kristen said. “But it’s not going to be an easy session for you. The next stages in your education are going to be difficult, I have to warn you now.” She spoke forcefully, stroking me more firmly.

  With those sensations running through my cock, I was hardly going to leave. I couldn’t imagine why the session would be so bad. After all, I was going to cum and come hard.

  “I want to start by asking you why, after our last appointment, you made this one.”

  I almost made up some story about how I missed her, but I knew I had to tell her the truth. So I told her about the gym and the hot tattooed blond girl, how she shut me down so completely. And how she showed up the next day with a stud.

  “And how did that make you feel?” she asked, continuing to stroke me.

  “Small,” I said.

  “What else?” Kristen asked.

  I hesitated. “Inadequate.”

  “Good. You’re being brutally honest with yourself right now. This is really going to help us. What else?”

  I thought for a minute.

  “Desperate.”

  “Yeah, she said,” stroking me casually. “That’s a good word for it.”

  “Does it bother you that he probably hit on her like you did, or even if he did, that she probably gave in?”

  “Yeah.”

  “You realize she probably hit on him, right? Either because she saw his big dick, heard about it, or because there was just, you know, something about him?”

  “Yeah.”

  “You saw how confident he was, right?”

  “Yeah.”

  “Girls can’t resist that. We say we hate cocky guys, but what we hate is false bravado”

  “But some guys, there’s a … vibe. When you can sense he can back it up—that kind of guy—he makes us sooo wet. The first time I had that experience was right after high school,” she continued, always stroking, as if her touching me sexually was completely natural. “I was playing hard to get with my boyfriend. I had dated him three months and only let him finger me. Then one night we went to a college party and I fucked a frat boy that same night. It was incredible. I couldn’t help myself. Something about him, the way he moved, the way he looked at me. Like he knew he could make my pussy cum because he had made a lot of other pussies cum. All he gave me was a chance to be his slut for one night … and I took it. I got my brains fucked out by his big cock.”

  Her smile was dreamy now, nostalgic. “He was so much bigger than my
boyfriend,” she went on. “My boyfriend was sweet and considerate, but tentative. This guy … he just ravaged my pussy, completely owned it. Took it over!”

  I didn’t want to cum yet, but I couldn’t help myself, thinking about a guy who could get Kristen on her back that fast, spreading her legs wantonly, cheating without much, if any, regret. I started cumming all over my belly.

  “Ha!” Kristen said. “Tiny dicks come so quickly!”

  I felt shame when she said that, but the orgasm felt so good it was more than worth it.

  “We’re going to have to keep working on that,” Kristen said, reaching for a towel.

  “What?” I asked.

  “Your staying power,” she said. “Or what you can do when you cum fast.”

  I was red-faced, but could offer no argument. Clearly it was a lesson I hadn’t learned yet.

  She used a towel to remove all traces of cum.

  “We’re not done yet, so I want you cleaned up for the next part,” she said.

  Not done yet? What else?

  After she dried me off, she looked at my cock as if inspecting it.

  “It’s really fucking tiny when it’s small, huh? We need to get it hard again somehow.”

  Somehow, as it turned out, involved her slowly unzipping and removing her sweatshirt—yes, there was a bra after all—and then her cutoffs. Her black lace bra and panties were all that that was left, and she was quite a sight. She sat down on the table with her back to me.

  “Unsnap my bra,” she commanded. I struggled with the zipper, causing her to giggle. But then it came off. When she turned around, I could see her breasts hanging confidently in front of her. I was torn between wanting to fuck her brains out and fearing she was way too much woman for me.

  I got the sense she was looking at my face the whole time, gauging my reaction.

  “What do you think?” she asked, standing before me for inspection like a goddess consulting her slave.

  “Oh my god,” I said helplessly. “You’re so beautiful.”

  She kneeled toward me, thigh muscles rippling, aware of the power of her hips.

  “Put your fingers in my pussy. Feel how wet I am.”