The Education of a Cuckold

by Alex Hathaway

  I dutifully stuck in two fingers. They went right into her moistness. She was sopping wet.

  “You know why I’m so wet?” she asked.

  “Because you put me in my place?”

  “Exactly! But I have bigger plans for you.” With that, she took a look at my dick. It was rock hard solid again, as if it had never cum in the first place.

  She hopped off the mat, walked over to a small table in the corner and opened the drawer. She peered over her shoulder, checking to see if I was staring at her ass, which I was. I thought I saw a flash of anger, but then she smiled, walked back to the table holding something.

  It turned out to be a condom.

  “I got a package of small condoms today, for little guys,” she said.

  I felt a rush of heat suffuse my face.

  “Usually I buy large condoms, and the checkout girls seem jealous or at least interested in my purchase. This time I got a different look.”

  She smiled at me, slowly rolling the condom onto my erect cock.

  “But it was worth it, because this is the next phase in your education, and I couldn’t risk a condom falling off your little cock when you’re in my pussy,” she said wickedly.

  I found myself twitching in her hands, loving her touch. “In my pussy?” Hadn’t she told me before I would never, ever fuck her?

  “So are you ready to fuck me?” she asked.

  “Yes!” I said without any hesitation.

  “You really want inside this pussy, don’t you?”

  “Oh god, yes!”

  “Well, I haven’t had a dick that small inside my pussy for a very long time, and back then I was practically a virgin,” she teased. “So if you want to get inside this pussy, you’re going to have to beg me for it.”

  With that, she got on the table and straddled me, rubbing my cock to remind me who was in charge. Then she slid the condom onto my cock.

  “A nice, ‘snug’ fit—just like it says on the box!” she said, laughing.

  I was crazy hard, but she wouldn’t put me inside her. Instead she stroked me in front of her pussy, sometimes rubbing me against her lips.

  “Please … please let me fuck you!” I hated how desperate that sounded, but I wanted it so bad. I didn’t want to cum first and ruin this chance.

  Without missing a beat, she raised her pussy up above my cock, teasing it a bit, brushing past the opening and raising up again.

  “You really want to fuck me?”

  “God, yes!”

  “Then beg me to put that tiny dick inside me, since my pussy is used to so much more.”

  “Oh, please!” I said.

  She smiled and rubbed up against me, pressing my cock against her belly.

  “Only if you beg me,” she said.

  “God I’ll do anything!” I said, thrusting up toward her, but she had my cock pressed down against my belly. I wasn’t getting in without her approval.

  “Jason, you have to really beg me to put this substandard cock inside my beautiful pussy!”

  “Oh, please, put my little dick inside you!”

  “Getting closer.” Suddenly I knew what I had to say. And that I had to say it loud.

  “Please put my tiny dick inside you!” I practically yelled. A smug look of approval from Kristen.

  “Okay, but be careful what you wish for.”

  With that, she put my dick inside her and slid all the way down on it in one motion.

  She moved up and down to get the feel of it before removing her left hand from the base of my cock.

  “See how easily this fits inside me?” she asked.

  “Yeah …” I said.

  “This is a problem for girls. We want friction. What I feel with you inside me is … pleasant, but it’s subtle, more like a concentration exercise than a mind-blowing experience.”

  As she said it, she started to ride up and down. “Let’s see if I can feel you any better if we move faster.” She was quiet as she closed her eyes in concentration. “With a big dick inside me, at this point, I’m still struggling to get it in, to adjust to its thickness.”

  She started bouncing up and down more vigorously. I reached up and grabbed her tits, trying to caress them like she had taught me. But she pushed my hands away, as if distracted.

  Then she started slamming into me hard … but my cock slipped out. She guided it back in and got back into thrusting, but I slipped out again.

  “This is the other problem,” she said. “Not only am I having trouble getting friction, but I can’t keep the motion going. With a nice big cock, I can ride up and down and still have a lot of cock to spare for long thrusts. That means I’m constantly getting massaged way up inside me, no matter where he is in the thrusting motion—no breaks, no slips, just pure fucking rhythm!” She licked her lips. “And that’s what makes a pussy cum. With a little dick like yours, it’s better just to grind, not to bounce. I’ll show you what I mean.”

  She took me all the way inside her and ground into me strongly, pubic bone on bone.

  “Ohh …” I said.

  “Does that feel good?” she asked.

  “Oh yeah!” I said.

  “See, that’s the problem,” she said, leaning over me, letting her hair cover my face and her breasts rest on my chest.

  “Problem?” I said. It felt incredible.

  “It feels amazing to you, but to me, well, I really don’t feel anything much. We could do this for an hour, and it would never make me cum,” she said. “Well, maybe not for an hour,” she said and laughed. “You’d cum way before then.”

  “But what if I worked your clit while we were fucking?” I asked hopefully.

  “Well, that might work, but that’s a different kind of cum,” She explained. “It’s a clit orgasm, not a deep vaginal body cum. Let’s see if your little dick can last five minutes inside my hot pussy.”

  She sat back upright, grinding on me in a circular motion, really letting her hips move around the base of my cock. So much so that I almost fell out again, but she pulled me right back inside her and kept moving.

  I couldn’t help myself. In just a couple minutes I was cumming, spurting up into the condom. She was totally in control. She started to laugh.

  As soon as I came, I felt this wave of despair and nausea sweep through me. Why was I subjecting myself to this? I felt like a virgin who had failed to please a princess and was now condemned to be locked in the stocks.

  A couple of tears welled up. Her face instantly softened …

  “Oh honey, that’s okay, that’s okay, let it out.” She kissed me on the lips and cheek, still holding my cock inside her. She had compassion for me, but she was not sorry. She was the furthest thing from sorry.

  “You’re a great man, a brave man. You just … have some sexual learning to do. I’m not just going to break you down, you’ll see.”

  I hate to write it, but I cried some more.

  “You do like fucking me, don’t you?”

  “Yes,” I said.

  “That’s good,” she said. “You’ll look back on this night, and you’ll remember how hot it was, not how sad.

  “Mmmm,” she added. “I haven’t had this much fun with a man in a long time.”

  “Fun?” I repeated.

  “Yeah … Usually guys are way too tied to their egos to let themselves go like you have. I love it!”

  With that, she stepped off the massage table. I assumed it was over, that she would be reaching for her clothes. But she didn’t.

  “How’s that little dick of yours doing?” she asked me playfully, teasing me with her right hand. I was rock hard again … already. Just talking about my predicament had brought my dick around again.

  “Okay, so I have to tell you, this next part isn’t going to be easy for you either, but it’s really important,” she said as she stroked. “If you go along with this, it will help you, and then I promise you a fantastic orgasm. Fair enough?”

  “Okay,” I said, unsure. But there was no looking
back.

  “Now, for the next few minutes, I’m going to act a little different, like a girl who is desperate to be fucked … okay?”

  “Okay,” I said again, wondering where this was headed.

  “Stand up now,” she said in that commanding voice that always put me in motion. I stood.

  With that, she leaned against the door and stuck her ass out at me, moving her fingers up and down her pussy lips.

  “Oh, god, I need a good fucking,” she said, moving fingers in and out while rotating her ass. I had never seen anything as hot as her gorgeous tan ass from behind. Or as demanding.

  “Get over here and fuck me!” she said, looking back at me almost angrily.

  I did as I was told, standing behind her, trying to work my cock in. But she was standing at a tough angle, and truth be told, she was taller than me. I moved the tip of my cock against her pussy lips, but her ass was moving, and I couldn’t get it in.

  “C’mon, fuck me!” she said, her voice loud and insistent.

  I tried again to get my cock up in her, but with her ass moving around, even though I was rock hard, she was just out of reach. I was starting to get embarrassed.

  “Dammit! Your cock is too small to fuck me like that. I really need it, too… Let’s try something else.”

  This time she leaned over the edge of the massage table, sticking her ass up in the air for me.

  “Fuck it! Pleeeasssse.” She looked back at me, in heat but angry.

  I got behind her. From this angle I was able to kind of get my cock head in after a few false starts and more sighs of impatience from her.

  Not wanting to risk falling out, I pushed myself up into her until I was at the base.

  “That’s it. Put it in deeper, give me more …”

  I knew I was in all the way, so I tried to ignore that and concentrate on the effortless sway of her body. I started pounding her.

  “Yes,” she said, “give it to me harder!”

  Gaining confidence, I grabbed her waist and started pounding her as hard as I could. I was really in a rhythm and could hear her moaning loader as the base of my dick slapped against her ass. I was really doing it!

  But then she started pushing her ass out at me harder and moving it around a bit, trying to get in deeper. Even concentrating on my strokes, I slipped out. I reached down and got it back in and started pounding again, but she was really getting into the motion and I quickly fell out.

  “Put it back in there!” she said insistently. I tried, but I was starting to get nervous and I couldn’t find her entrance easily with her ass moving in the air. I tried, and failed. Tried and failed.

  Sighing again, she reached back and guided it in herself. I started pounding again, but again when she bucked her hips against me, I fell out.

  “Damnit!” she said. “It’s no use.”

  She rolled over again, rubbing her pussy. “And I needed to get fucked so bad.”

  “I can do it to you on here!” I said, climbing on the bed. She pushed me off.

  “I don’t think you understand,” she said. “I needed to get fucked, really taken, taken by force from behind. But your tiny dick kept falling out.”

  “I know I can fuck you from the top position,” I said insistently.

  “Okay,” she said with a bit of resignation.

  I got on top of her, amazed at the view from above, the sweat rolling off her breasts and face.

  I put myself inside her and started pushing.

  “Yeah,” I said, unable to help myself.

  “Does that feel good?” she said, almost glaring up at me.

  “Yeah!” I said, stroking inside her amazing pussy, not believing my good fortune.

  “Because I can’t really feel much,” she said. “Oh well, I’m glad you feel something.”

  I started pounding her harder, but she reached up and grabbed my waist and slowed me down again.

  “Don’t bother,” Kristen said. “It’s not going to make me cum, and that wasn’t really the point of this anyhow.”

  “So what was the point?”

  “I’ll show you next week,” Kristen said, unceremoniously taking my dick out of her. All of a sudden, she was uninterested in me and my orgasm.

  “Go ahead and get dressed, and I’ll see you next week. I’m going to take a shower,” she added matter-of-factly. Then she turned toward me. “I want to remember exactly what we did today, how it made me feel, how it made you feel.” She wrapped her body in a towel and walked out. I could hear her shower sputter up in the distance.

  After she left the massage room, I stood there alone, my cock rock hard, my balls aching. I put my erection back in my jeans, feeling mad at her and also humiliated. I honestly wasn’t sure I would call her again. In that moment, I thought, Probably never.

  Chapter 11

  I did call Kristen again. Eventually.

  Truth is I struggled with this, asked myself if it was self-destructive, asked myself if it was a hopeless addiction fed by the most confused parts of myself. To this day I can’t tell you with any certainty it wasn’t one of those things, all those things. What I will say in my defense is that I continued to try to find something better. I had started to fundamentally question whether Kristen had my best interests at heart. She had promised to break me down and she was well on the way. But to what end?

  So I tried. I asked out a few girls I kind of liked. I had to force the issue a bit, as I didn’t have a huge crush on these women. Years ago, my grandfather of all people had advised me that sometimes you “fall in like” with someone first, and then you fall in love. That love was more about being there, companionship, and the other feelings that grow over time. “Quit looking for Mrs. Perfect while other guys go marry Mrs. Good Enough,” was how he unromantically put it.

  In my mid-twenties now, I was starting to see his point. More women that I had some kind of interest in were either engaged or married. For the first time I could see how you pay a price for waiting for the perfect situation. Although I wasn’t really waiting for perfect. I just wanted someone who could reach inside my heart and shake me. Maybe that was a search for perfection. Kristen had no problem doing that to me. But with her I faced a different challenge—mutuality of feeling. She loved me but I LOVED her. That discrepancy was brutal.

  So after that last meeting, I tried to date. Tried. But my heart wasn’t in it. I found myself staring across a dinner table listening to an attractive woman talk about her career plans—law versus business, corporate law versus advertising if you really want to know—and I just couldn’t see myself in her life. Each woman was nice in her own way but none of them grabbed me by the jugular.

  I suppose on some level I had outgrown nice. I had come to crave truth. Nice felt phony and truth was a relief. Truth I could work with. Speaking of which, while Marilyn (our career planner) was talking, I found myself looking forward to being back in bed alone, where my thoughts often turned to … Kristen.

  A full month had gone by since our last “incident”, which is how I had taken to referring to these encounters. The flat-out truth is that I was worried to let too much time pass, to let whatever strange opportunity I had with her pass me by. I called her, left a voicemail. “I want to continue.” I liked that —cryptic and mysterious.

  I didn’t hear back for two days. Three. I was starting to wonder if that particular train had left. But on the third day, she called.

  “Can you meet me at Regina’s gym, ten p.m. tonight?”

  The time was odd. So was the place. Regina was a friend of hers who had a small gym she used for her clients who were rehabilitating from workplace injuries. I guess they had some kind of “client swap” thing going with the massage work.

  Of course I said yes.

  Regina’s gym was in the basement of a small shopping complex. It was a dark, private location with no windows. In fact, about three months after this particular story, she ended up moving it to a storefront with way more light. But the privacy was what Krist
en was looking for, I guess.

  When I arrived, I had to knock a few times to be heard from the back entrance. Kristen came out, wearing a tight-fitting spandex outfit and leotard. She looked as hot as you would expect, though to be honest it was the dresses that really knocked me out. But anytime someone is completely at ease in their own physicality, you have to take notice.

  Walking into the door of the gym, a big surprise awaited me. We were not alone.

  “This is Jim,” Kristen said. I gave Jim a once-over. He was a big strapping guy, but kind of a lunk, a cross between Mr. Big on Sex and the City with George Costanza on Seinfeld. He was taller than me but kind of awkward, and certainly out of place in a gym. Jim was not in particularly good shape. If anything he had a pot belly and the physical look of a guy who would rather suck down a six pack with his pals than get up the next morning and jog with co-workers. Jim seemed like a bit of a creep, and he gave me a funny look.

  What was I supposed to do, shake his hand? It looked like Jim was about to extend his hand to break the awkwardness.

  “Jim’s going to be fucking me today,” Kristen said. “And you’re going to be watching … well, mostly watching.” They both snickered at this inside joke and looked over at me, standing awkwardly, unsure of what to do.

  “We picked this gym because no one is here at this time of night and, well, I’m going to be making a lot of noise,” Kristen said, smiling knowingly at Jim. They both laughed and looked at me.

  “Oh and yes, this is very much part of your instruction,” she added. My cheeks flamed.

  And with that, she kneeled submissively before him and started massaging and rubbing a growing bulge in his sweatpants.

  “Wait till you see this,” she said, looking at me.

  She struggled to get out whatever was underneath. Then she pulled out this long, thick rope of a cock, which hung down obscenely. To this day, I have never seen a bigger soft cock. It was maybe seven inches, thick and arrogant. And uncut. Kristen sighed audibly when she saw it, and she had seen it plenty of times before.

  When I first saw Jim’s penis, I imagined it must be a foot long erect. With Kristen kneeling in front of him stroking it, I was about to find out. What surprised me was how she behaved with him. She was actually whacking her face with his soft cock, playing with it carelessly as she looked up at him admiringly.