The Education of a Cuckold

by Alex Hathaway

  I put the paper down. It was a lot to absorb. That last point was the doozy. It was not easy to read, but I could tell she was right. With all the experiences we had shared … all the points hit home.

  “Do you understand?” Kristen asked me.

  She smiled. She could tell I was aroused by reading the list, but didn’t seem to let on, other than crossing and uncrossing her legs to give me a sense of how her power skirt clung to her body.

  “What we’re really talking about is small penis acceptance, but not shame,” Kristen said. “You get that, right?”

  “I got it.”

  “Most of the guys I know with small dicks are insecure in the bedroom and assholes outside of it, trying to prove something,” she said. “I’m giving you a totally different road. You understand?”

  “Yeah,” I said. She seemed to know where this was going and that it was turning me on, too. She always knew.

  “A lot of big guys, they just get cocky with it, and it gets old—inside and outside of bed,” Kristen said. “That’s where you can work it. Work your ass off to be a better man. And in most ways, you can be.”

  For some reason, this honest conversation about my sexual liabilities and what I could do about them was really turning me on. Kristen seemed a little flushed in the face as well. I realized later she must have truly enjoyed having this kind of brute naked power over me, without any pretense.

  “So, are you ready for your final lesson?” she said, putting a knowing hand on my erect dick under my pants.

  “Yeah,” I said, wondering what was in store for me.

  “C’mon,” she beckoned to me. But instead of leading me to the massage room, she led me to her bedroom—that bedroom I had fantasized about so often. She stopped me outside the door.

  “Let’s pretend you’re my co-worker, and my husband is out of town. I asked you to come over to help me with a deadline, but you could tell from the beginning something was up. The sexual tension has been building between us for a while. A tour of the house ends outside the bedroom. I couldn’t be more obvious …”

  She put her arms around me, kissed me once on the lips.

  With a confidence that surprised me, I not only kissed her back, but placed my hands on her ass and pulled her closer.

  “Ahhhh,” she said, smiling at me with surprised delight. “You know what I want?” She kissed me once more. “I wanna fuck.” She moved her hips against my crotch, rotating in a sensual manner. Damn she was a goddess.

  She grabbed my hand and pulled me into the bedroom. I was worried that I was falling into another humiliation trap. She had taught me how to please her, but I knew all too well what would happen if I tried to fuck her.

  She pulled off her sundress in one fluid motion, tossing it on the floor. I stared at her intimidating body with lust, she looked a bit like some pictures of a young pop diva I used to jack off to when she was younger but beginning to flesh out her hips.

  “Can you give me one of those massages you were telling me about?” she asked.

  Realizing she was still role playing, I said, “Sure, let’s get you down on the bed.” I guided her down and laid her on her stomach. Kneeling on top of her, still fully clothed myself, I worked on the massage moves she had taught me, starting with the more neutral parts of her body, neck, and shoulders. Working my way down to her back. But before I got to her ass, I started again on her feet.

  “Ohhhh,” she moaned as I pulled away. “You’re teasing me.” It’s about time you got some of that, I thought to myself as I worked her toes and calf muscles. Working my way up to her thighs, I could feel her trembling anticipation. I almost whipped off my pants and stuffed my cock inside her, but I knew better. I knew I had to pace myself. I kneaded her sexy leg muscles and hinted at going farther up her thigh, but always pulled back.

  She started pushing her ass up in response, clearly wanting my fingers to move up farther … up into her. And the more I withheld, the more she moaned.

  Finally I shoved three fingers directly inside her—hoping that was enough to make an impression but not enough to cause pain.

  “Oh my God!” she said. “Oh!!”

  It was great to feel her squirming, almost trying to get away from my hand as I pulled her closer. For perhaps the first time ever, she was in my rhythm. Without missing a beat, I flipped her over onto her back and moved up against her, working my fingers in and out of her. In this position, I could get at her clit a lot more easily, so I worked it.

  She spread her legs for me wantonly wide, and I worked my fingers in and out, bringing friction to her clit here and there but pacing it all, savoring the moment.

  “Damn that feels so good!!”

  “You’re damn right it does!” I said, taking control. “Guess what I’m gonna do next?” I asked her.

  “What?” she asked, squirming on my hand, looking at me helplessly.

  “I’m gonna make that pussy cum!”

  “Oh my god I want to fuck!!” she said, rubbing her clit while clenching her hand between her legs.

  She quickly rolled off the side of the bed and walked over to her dresser. She grabbed what looked to be a large clear dildo, with some kind of strap.

  She kneeled before me, unzipping me. Without breaking character, she took the plastic dildo and slipped it over my cock. Just her grip on my cock made me strain hard.

  “Oh wow your cock is really big!!” she said, looking at me with lust as she worked to secure the straps on my back.

  It was amazing to watch a big thick cock dangling from my body, almost hard.

  “My husband can’t please me,” she looked up at me expectantly. “God I need this!!!”

  I reached down and grabbed the clear soft plastic “cock” with my right hand, moving it up and down. It was amazing to feel the heaviness and extent of the thing in my hands. You could see my own cock a little more than halfway up the sleeve, with extra room around it. But she pretended it was all mine.

  “Oh yeah!” she said. “I can’t wait to fuck that big cock!” She lay back on her bed and spread her legs wide again, moving her hands up her thighs. “C’mon, get it in there!”

  Remembering her advice, I kneeled in front of her, but I stopped deferring to her. I pushed her legs even farther apart and immediately began working the large head of the dildo into her pussy.

  “Oh wow!” she said. “Be careful, I’m not used to such a big cock. My husband has a really tiny penis.”

  I was totally erect with this smack talk and the different position she had cleverly put me in. I pushed the dildo in about halfway and heard another gasp from Kristen.

  “Take your time,” she pleaded, “Let me get used to it.”

  I started working it back and forth inside her. The movement was a little awkward—I was getting used to the tug of the straps from behind me—but it did seem to come pretty naturally. It took focus, but I was able to start thrusting inside her faster.

  “Daaammn,” she said. “That feels gooood.”

  Thrusting into her was a weird experience. I couldn’t feel much sensation on my cock inside the sleeve, but I was rock hard. It was amazing to savor the pressure of the plastic cock up inside her. The in and out friction was like nothing I had experienced, and the resistance from her pussy on each thrust from being so filled up was just as novel. I felt a flash of jealousy for guys with cocks big enough to feel that kind of pressure all the time, and the way she seemed to work in rhythm with that pressure. Enough!

  I pushed her hands back while she fought with me in fake resistance, then I pushed the cock all the way into her.

  “Aaaaaah!” she said. I was so deep inside her. I started moving in and out in long strokes, pushing all the way into her each time.

  “Fuck!” she said. “Fuck me!”

  I kept on pushing. As I pulled in and out, I looked down to watch her pussy stretched wide around the dildo. I was able to push in pretty hard without losing the rhythm.

  Then I had an inspiration. />
  “Does this feel better than your husband’s little dick?”

  “Oh god! So much better!” she said. “Fuck!” she cried out for emphasis, as she started to rub her clit feverishly. “Keep going like that!”

  I was able to thrust in and out pretty quickly, not slamming her but with enough force. I could feel her pussy contract in rhythm along with me, a swelling sensation. I suddenly realized what that meant: she was going to cum all over me.

  “I just knew you’d know how to fuck me!!!” she cried out, pulling me in as hard as she could. The base of the dildo was jammed all the way in, and I could feel her tremors beginning.

  “Oh yeah,” I said, all cocky now. “Cum for me like a good little slut!”

  I could feel her body tense up and then spasm in release. “Cummmming!” she said.

  She pushed the cock out of her pussy with the force of her orgasm as her legs spasmed.

  It wasn’t the extreme kind of cum I had seen her experience at the gym, but it was a way harder cum than anything I had managed with my naked cock or even my hand in the past.

  “Daaammmn …” she said.

  I was amazed I hadn’t cum myself, not from the sensations but from the power rush, that I had ripped an orgasm out of her.

  “I needed that cum so bad!” Kristen said. I wasn’t sure if she was still role-playing or not, but I did know she had cum.

  I lay down next to her, happy that I had made her orgasm, happy that I had taken control of the situation.

  “You were great,” she said, reaching over and grabbing my plastic dildo cock, which was sticking up in the air, perpetually ready.

  “That’s a nice big cock you have,” she said.

  “Why, thank you!” I said. We both laughed.

  “So,” she said, “you see what I’m getting at, right?”

  “I think so,” I said. “You want me to … to always be ready, always have the confidence to take control of a woman’s body when I have to.”

  “That’s right!” she said. “And make sure to keep the toys around in case you need them. Just don’t get dildos that are too big. You see how this dildo is big, but not huge?”

  “Yeah,” I said as she stroked it.

  “That’s because toys are harder to take than real cocks,” she said. “My favorite real cocks are around eight inches. My favorite toys are about this size.”

  “Which is?”

  “Seven inches, pretty thick,” she said. “This is a good size for a strap-on toy for you. You can get it all the way inside most girls and push hard, but it’s still waaaay bigger than your little dick, see?” She continued to casually stroke the plastic cock.

  “Yeah,” I said. She laughed. It was true. My cock was only a small part of that bigger plastic toy. You’d have to grow my cock several times over to get to the outer edges of the plastic.

  “Of course, the only problem is that you won’t be able to feel much when you’re fucking a girl with this strap-on,” she said.

  “Right,” I said.

  “But that’s fair, because she won’t feel much when you’re NOT using the toy, will she?”

  “No,” I admitted. Kristen smiled.

  “And why is that?” she asked me sternly.

  “Because my cock is too small to fill up a pussy,” I said without hesitating.

  “Yes!” Kristen smiled with satisfaction. “But that doesn’t mean you can’t have loads of fun in the bedroom.” Her hand relaxed around the dildo. I found myself wishing she would grip it hard.

  “So if I have a toy, does that mean that I … have enough for a girl?” I asked, looking over at her.

  “Honestly?” she said.

  “When have you not been?” I asked.

  “Well, it’s a mixed bag,” she said. “Most guys think girls want a huge dildo, but if you can get them to try a toy, this size is really better. This bigger cock will make most girls feel really good, but it may awaken them further to the real thing … and to your shortcomings as far as penetration goes. They might start thinking, If this bigger toy cock feels so much better …”

  I finished the thought for her. “… Then how good would a real big one feel?”

  “Exactly,” Kristen said. “And it’s not quite the same, the toy. Some of the physical sensations are similar, but …”

  Once again I finished the sentence for her. “Not the psychological feeling of being totally taken.”

  “Exactly!” she said. I had almost surprised myself.

  “And you could see. It was a good cum, but it wasn’t …

  “A mind-blowing one,” I said.

  “Yeah,” she said, “and there are other things about big cocks … like the ones that are big squirters. And pulling down a guy’s pants and seeing a big pussy-killing cock flop out, it’s just so intense … It’s just …” She sighed and rubbed herself a bit. “You just have to be open to wherever a relationship takes you.” She paused. “But just don’t forget,” she added, “girls love a great fuck, and a part of you needs to be put in your place. You need to figure out how to be both dominant and submissive. I should have called that point number sixteen, now that I think of it!”

  “Hmmmm,” I said, contemplating my situation. I needed some time alone to process all this, but I didn’t feel depressed like I had in the past after our sessions. Something had shifted.

  “Ready for one more cum?” she said.

  She started gripping the plastic cock tighter as she stroked.

  “Let’s make that little dick squirt inside here!” she said, stroking me faster.

  I knew it wouldn’t take long. It felt so good with her gripping the dildo tight like that.

  “Oh yeah!” she said. “Look at your tiny cock twitching inside here.” She worked it up and down. “Don’t you wish you had a cock this big?”

  “Oh god, yeah!” I said.

  “And to think, if you had a cock like this dildo, you’d be the smallest lover I’ve had in years,” she said, smiling wickedly at me and gripping the plastic hard around my cock. “C’mon, let me see that tiny dick squirt in there!!”

  That was all I could take. I started squirting into the dildo, bucking my hips off of the bed.

  “Oh GOD!!” I said.

  “That’s it,” she said with a smug smile.

  I was spent. I cleaned up in her bathroom while she got dressed.

  In the living room, she was waiting for me. She had cleaned the dildo and put it in a bag for me.

  “That’s for you to keep,” she said. “And use!!” She gave me her best teasing smile. “I’m really proud of you.” Wrapping her arms around me, she added, “Now go get yourself some more of this.” She kissed me sensuously on the lips.

  I grabbed her ass one more time.

  “Hey!” she said, looking at me disapprovingly.

  But I could tell she was impressed.

  I have not seen Kristen since.

  Chapter 14

  The next few years of my dating life were pretty darn good. My size insecurities didn’t plague me anymore. That probably sounds strange to you. But I just seemed to have a clear view of who I was. What I brought to the table, and what I lacked, only without the judgment.

  Yeah, I missed Kristen sometimes. This is what bothered me most: for every time I was sad, there were ten times when I missed our kinky games. Even though I knew those games were fleeting. Even though I knew deep down she didn’t love me. She loved me, but with a lower case “l.” Even if you’ve struggled to find love as much as I have, you sure as heck know the difference between the two. But yeah, I missed her. On the other hand, leaning forward into your life is not so bad either. And whatever Kristen’s failings, that’s where she came through.

  Asking girls out was a lot easier after Kristen. Enough of them said yes to make my life pretty interesting. One girl I dated—a medical technician who was used to being in charge—actually said, “I love how you made me your slut!” after I had brought her to countless orgasms with my tongue
, fingers, and then with her vibrator. Without asking for her permission to make her cum. Just, you know, taking it. In a way she completely and happily allowed, just like I had seen those big dicked alpha guys do.

  It turns out I was pretty good at playing an alpha male type role for certain girls. There was a fitness instructor who loved being tied down by someone stronger. No mean stuff, just restraint, then plenty of orgasms while she was living out that feeling of helplessness. Fortunately I had lifted enough weights after Kristen kicked me in the ass that I was pretty strong. I could tell that made a difference to Tina, my fitness instructor girlfriend.

  The fact I could hold her down even when she offered serious resistance was a big turn-on to her. I could tell that if I hadn’t been strong enough, she would have been turned off. But I was, and so was she. I was pretty good at understanding what made girls tick after all. I suppose the fact that I could afford to take them out to nice dinners and buy thoughtful gifts for them didn’t hurt either.

  So that was my late twenties—dating girls, not sure what I was looking for exactly, but enjoying my newfound ability to reel them in. The only real glitch was one woman, Nadine. Nadine was a black belt in karate, and while I was a bit stronger than her, she was not at all intimidated by me physically. We only tried to fool around once, and when she got me undressed and my cock hard, I could tell she was disappointed. I pretended not to notice and even dialed it up a notch.

  I did my oral thing on her instead and she was happy enough, but I could tell she wanted to be dominated and in this case, I didn’t feel like I had the touch she needed. We went our separate ways with no hard feelings. I put that experience behind me and hit the dating scene again. But deep down I realized there were some women my newfound confidence couldn’t reach. Trouble is, those were typically the girls I wanted most.

  The downside of my newfound confidence was that I wasn’t always fulfilled. Either I found myself in what I now call “vanilla” relationships where my taboo fantasies were not welcome, or else I was living out the girls’ fantasies without doing justice to my own. Maybe that’s why none of these late twenties girlfriends have lasted. I could see that at some point, one of them could become more serious. But what was I looking for? What was holding me back?