The Education of a Cuckold

by Alex Hathaway

  “Yes …”

  “Why is it then?”

  “Because I’m too small,” I said. It felt so right to say it.

  “Yes, that’s right, you’re too small … too small for what?”

  “For filling up a girl’s pussy,” I confessed.

  “That’s true. But it’s more than that,” she said.

  “I’m too small to make a pussy cum … hard,” I said.

  She took her hand off my cock for a moment, likely sensing I was about to squirt all over her if she didn’t.

  “Yes, but there’s more,” she said. “This part isn’t going to be easy for you. You’re really too small to fuck at all.” She almost blurted it out. I could tell she didn’t want to say it, despite her love of the truth.

  “I am?” I asked.

  “Yeah, you are,” she said. “Well, except for virgins or abnormally tight girls.”

  I was so close to cumming.

  “Or maybe girls who are totally in love with you, before the love settles in.”

  I wanted to protest. Somehow her words didn’t seem right, and I know they didn’t seem fair. But then my life experience to this point could not contradict her.

  “You have a lot to offer a girl, you know that, right?”

  “Yeah.”

  “Just not fucking.”

  “No, not fucking.”

  “So you need to find other ways, right? To please a girl.”

  “Yes,” I admitted. Such a relief to admit it.

  “And I’m going to help you with that,” she said, stroking me calmly again.

  “Okay.”

  “But first, I think that little dick deserves to cum. Does it feel good?”

  “Yes!”

  “How good?”

  “It feels amazing!” I said. I was going to explode soon.

  “You know why?”

  “Why?”

  “Because I own that little cock.”

  Ohh …

  “How does it feel to know?”

  “Know?” I asked.

  “That your cock can’t make my pussy cum, but I can make you squirt whenever I want.”

  “Ohhhhh …”

  “Whenever I want!” she insisted, stroking harder, easily grasping me with a few fingers. Then she proved she could read my mind. “And it only takes a few fingers! Let me see that little dick squirt.” She was stroking me super-fast. “NOW!!”

  I squirted on command, spasming into the air, rocketing a few spurts up to my face and neck.

  “That’s it!” she said. “That’s a good little dick!”

  I bucked my hips up. The combination of her teasing and stimulation was way too much.

  “Nice,” she said. “You really did cum hard, huh?”

  “Yeah,” I said.

  “See, for you, with a small cock like that, a teasing hand job is one of the best orgasms you can have.”

  I couldn’t argue.

  “It’s a lot tighter around you than a pussy would be.”

  True.

  “Now, go get cleaned up, but don’t get dressed, and meet me in the massage room.”

  I did. I was still in obedience mode, feeling great from the cum. I wondered when my “The heck with her!” protest mode would return. I went to the restroom, washed and scrubbed off.

  When I opened the massage room door, the first thing I saw was her yellow sundress hanging from a towel rack. Then I saw her, totally nude on the table.

  “Come over here,” she said, before I could really think straight.

  I walked over next to her, totally in her command.

  “Now I want you to put your hand in my pussy,” she said. “I want you to feel how wet it is.”

  I put my fingers down inside her, admiring her perfection as her breasts and hips swayed to my touch. It was true; she was really wet.

  “Remember that feeling,” she said. “That’s what a pussy feels like when it’s really turned on.”

  “How did you get so turned on?”

  “Well, taking control over you, it got me wet. And then thinking about how badly I needed to be fucked.”

  No hesitation. I took advantage of the situation, moving my fingers in and out of her pussy as she grabbed a breast in each hand, as if she imagined her lover grabbing her roughly while he fucked her deeply.

  “Now it’s time for some lessons for you, some lessons that will help you.”

  Lessons? I was just happy to be moving my fingers in and out of her.

  “Look at me. You see that I’m ready to be fucked, right?”

  It was true. She was squirming on the mat. I was surprised she hadn’t fallen off. Her pussy was dripping all over my hand.

  “You probably want to fuck me right now, don’t you?”

  “Yes,” I said.

  “But you realize the problem, now, don’t you?”

  “Yes.”

  “I need a deep, crazy-hard fucking, and you don’t have the equipment for it—simple as that.”

  “I know.”

  “When I’m bucking all over the place like this, I need an animal pounding, and you’re not going to be able to keep it in me.”

  “I know!” I said, a little forcefully.

  She smiled with satisfaction, pleased at how quickly I had acknowledged the truth of what she said.

  “Exactly! If you put your tiny dick inside me now, we both know what would happen. It would tickle more than it would satisfy.”

  “Yeah,” I said, relieved to be admitting the truth.

  “So here’s what you need to do,” she said. “If you get a girl in this situation, where she’s dripping and hot like I am, don’t put your little dick inside her.”

  “Okay.”

  “Trying to fuck her when you know you can’t … will just take her out of the mood.”

  “So should I try a toy?”

  “No!” she said. “I know it seems like a big toy would be the best thing, but it usually isn’t.”

  “Why?” I said, continuing to move my fingers in and out while she talked and moaned.

  “Because toys … well, they just aren’t like the real thing.”

  “Okay.”

  “Sometimes they work, but big dildos aren’t really what girls buy at sex shops. They buy little buzzing vibrators. That’s why, with a cock of your size, you need to focus on clit orgasms.”

  “Okay.”

  “It’s not the same as a deep vaginal orgasm, or that clit-vaginal double feature a big thick cock can pull out of you,”—Kristen seemed to be losing the point for a second, but she soon came back to reality—“but it’s still pretty awesome, and some girls don’t know any other kind.”

  Kristen proceeded to spend the next hour showing me how to work her clit with my hand, and then my tongue. She told me I had a natural talent for oral sex. She taught me how to rotate my tongue around the clit, backing off when she got too close.

  “Your technique could be better, but that’s due to your lack of experience.” She smiled, and my cock twitched. “You do have that passion,” she added. “You really go for it, like you love being down there. And that makes up for a lot.”

  But while I did Okay with my tongue, I did even better with my hand. And to be honest, I liked it better. I could really see her that way, see her squirming all over. I seemed to have a knack for knowing just when she needed more direct stimulation on her clit and when to pull away and rub the whole area, increasing the tempo to work with her own rhythm. I knew when to apply more pressure with the fingers. And I could see my hand had a huge advantage over my dick. I could stretch open her entrance or add as many fingers as I needed to get a reaction. I was really working her!

  Before I knew it, she was clutching my hand between her legs, squeezing and cumming. It wasn’t as intense as the body-shaking orgasms I saw her have a week ago, but it wasn’t shabby either. She called out “I’m cumming!” several times in a way that was gratifying.

  I was still jealous I couldn’t just pound he
r into submission with her legs wrapped desperately around me, but making her cum so good still did wonders for my ego.

  “Damn!” she said. “Your pussy-eating skills are decent, but your hand … your hand is brilliant. So this is what you need to do with girls.” Kristen was casually stroking her pussy. “The first time you get them undressed, you need to make them cum like that. Before you try to put your little dick inside them, before you try to cum yourself. Got that?” she demanded.

  “Got it.” I was starting to feel better about myself already. I could still be confident of making a woman feel awesome … if I knew my limitations and worked at what I could do.

  “For many girls, they won’t need anything more from you,” she said. “So when you fuck them, even it isn’t the best fuck ever, they are already satisfied.”

  “Got it.” This was making sense.

  “And they know you are attentive to them and put their needs first. Whereas, if you try to put your little dick inside them first, you’re likely to squirt really fast, right?”

  “Right,” I reluctantly admitted.

  “And either way, they will think you are selfish, putting your needs ahead of theirs.”

  “What about you?” I asked. “Are you completely satisfied?”

  I was scared to hear this particular answer. But I needed to. I had to.

  She put her fingers back inside her pussy, as if she was doing a quick gut check.

  “To be honest, yeah,” she said. “Of course, if you had a big thick cock it would be inside me right now, and that first big orgasm would have been the warm-up, but … I’m good.”

  I smiled.

  “And,” she went on, “I appreciate not having to pretend that I’m obligated to fuck your tiny cock.”

  I didn’t smile so much at that piece of ruthlessness, but I could see what she was getting at.

  “In my case, an orgasm like this, it sets me up to have a really good day,” she said. “It’s as if I had woken up and masturbated, but about five times more intense having someone else do it.”

  I did smile at that.

  “Okay,” Kristen said. “That was enough for today. Can you come back next week? We still have a little more to go.”

  Next week would not be a problem. For the first time, I was beginning to see a crack of light in the “break you down/build you back up” plan.

  I began to carry myself a bit different around attractive women. I felt … more confident again. But in a deeper way. Like I had a confidence that couldn’t be exposed. Even if I had to take my pants off. The shame and dread seemed to have faded in favor of a quiet kind of flow. I even had a woman ask me out on a pinball date. It wasn’t a romantic date, but I couldn’t help but think my relaxed style was part of the reason. I found myself looking forward to the next week with Kristen … and not just to the orgasm.

  Chapter 13

  The next week, Kristen greeted me at the door wearing a more professional outfit—a dressy skirt and jacket with heels. Her hair was pulled back, and she even had black glasses on, a sort of librarian fantasy. But the athleticism of her body made the outfit seem like a sexy contrast. Animal power and brains. I felt weak.

  She led me into the living room.

  “So, you like my outfit today?”

  “Yeah.”

  “I thought you might. It’s the kind of thing a girlfriend of yours might wear. You might see her like that as she comes home from work.”

  She sat down in a chair and pointed toward the couch across from her.

  “At first it’s hot to think about all the guys that must hit on her, because you’re feeling secure in the relationship,” Kristen laid it out, “but then, something shifts. You see that she is not paying as much attention to you after work. She isn’t in the mood for sex as often. She goes out more with her friends.”

  I wasn’t sure where Kristen was going with this.

  “Her indifference probably turns you on, just like me sitting over here, beyond your sexual reach.”

  Ugh. Twitch.

  “But you also know you’re losing her, that she’s drifting away. So … what do you do?

  “I take her on a special night out,” I said. “Give her a chance to tell me if anything’s wrong.”

  “And what else?” Kristen asked.

  “After dinner, I take her out dancing.”

  “Okay, that’s a good start,” Kristen said. “But what about when you get her home? Do you try to fuck her?”

  “Not right off the bat. I focus on tender lovemaking, giving her great oral sex.”

  “Not bad,” Kristen said. “I’ve taught you well. But there’s one more thing you need to do.”

  “What’s that?”

  “Let her in on your fantasies … all of them.”

  “Okay.”

  “And you know what that means, don’t you?”

  “I think so.”

  “It means telling her you fantasize about her with other guys.”

  Even hearing her say it, it was a little bit hard, and not in a sexually arousing way.

  “So, do I bring up the fantasies right away?”

  “No,” Kristen said. “At first you focus on the best sex you can give her. You never want to impose your fetishes on a girl. But at the first sign of problems, at the first sign she is bored sexually, start bringing up the fantasies … and ask about hers.”

  “Okay.”

  “You’ll want to have a couple of toys handy, like a big fleshy dildo, so you can share with her what you want, and see her reaction.”

  “Okay.”

  “So here’s the bad news, Jason,” she said. “This is the last time we are going to play together … for a while.”

  I’m sure I looked disappointed. Maybe relieved, but also disappointed.

  “You’ve learned a lot, and there’s more to do, but it doesn’t involve me.”

  I was quiet. I had a sinking feeling she didn’t mean a while. She meant forever.

  “The thing is, you need to get out there, get some confidence with other girls.”

  I felt bad, but somehow it felt right too. I could finally admit it to myself: the relationship was too unequal.

  “I’m going to give you some homework, some things to work on.”

  “What are those?” I asked.

  “Well, it’s a fourteen point plan.”

  “A what?”

  She handed me a piece of paper.

  “Go ahead and read it.”

  She had titled the piece, “Sexual Success for the Small Penis Man.” It was funny to see all this written out in her masculine, jagged scrawl. Penmanship was not her subject.

  The instructions were numbered, just as she said.

  “Read it to me,” she said, putting her beautiful hose-encased legs next to mine.

  So I did:

  1. Do everything you can to improve your overall sexual skills, including oral sex, finger sex, nipple caressing, sensual massage, and teaching yourself to last longer before you cum.

  2. Do not let your inadequacies affect you outside the bedroom. Become as successful as possible in your field, including financially. Stay physically fit.

  3. Work on your emotional and intimate relationship skills. Always remain humble and try to be the best partner you can be.

  4. Work on being naturally assertive so that you are not seen as a nice guy who can be pushed around or exploited.

  5. Cultivate a bit of wild side outside of work. Pursue creative passions, keep an edge to your personality.

  6. Focus your sexual energy less on women and more on accomplishing things that give you an authentic sense of power and status.

  7. Remember to stay true to your own integrity. Use your power to raise others up. That kind of power makes women swoon.

  8. Never let your manhood outside of the bedroom be defined by your smallness inside of it. Be a strong, brave man who has a reputation for looking out for those you love.

  9. Never, ever, try to pretend to girl
s that you can make them feel the way a true alpha stud can make them feel. Know and respect your sexual place, but remember you can still make a girl feel VERY good.

  10. Don’t impose your cuckold and submissive fantasies on a girl. When you’re first dating, focus on making her happy and don’t draw attention to any submissive fantasies until she brings them up. Don’t forget anal sex, which can be a great option for a smaller guy if she is into it. Perhaps when she is drunk.

  We both laughed out loud at the way that last line came out. Years later I would remember it as vintage Kristen.

  11. The second you sense there is a problem satisfying your girlfriend, whether it’s the first date or the tenth, you MUST start dropping hints that you are open to fantasies, role playing, and open discussions about any sexual topics that turn her on. Be ready. Even when she seems totally in love with you, be ready.

  12. Remember that being painfully honest and open when the sex gets stale, as it often will if you are under-endowed, is very important to avoid cheating and deception.

  13. If by some chance you do meet a girl who is perfectly fulfilled by you, despite your size, you may still have to eventually bring up your size inadequacy feelings and cuckold fantasies in order to tap into your own desires.

  14. Many attractive women are not fully aware of how vulnerable they are to cheating on their mates until they are unexpectedly seduced. You must prepare her for this possibility even if she is resistant or if it is hard to talk about. This will plant the seed that she can bring you into the fantasy (or reality) instead of cheating on you.

  15. Don’t make her feel slutty and ashamed if she admits to being unsatisfied or even having cheated on you. Let her know that getting deeply fucked by a real man is a primal need for most women, and she has nothing to be ashamed of for craving total submission and ECSTASY, just as you have nothing to be ashamed of for not being able to do that to her. These needs have nothing to do with her love for you or fidelity. Like it or not, they are deeper than love. Be able to talk about them openly in fantasy, but don’t assume you will need to make them a reality. At the same time, be prepared to make them a reality if that is what’s necessary.