1. “Oh, it’s so small.”
2. “Wait, you didn’t, um…already?”
I’ve been asked both those questions by Emily, both early in our relationship, and each time she asked them, I had to answer yes.
“Oh, it’s so small.”
She asked me the first question after we’d been dating for about a month—we were at my house, in my bed, naked, during the day, mid-morning, actually. We were hot for one another, hot like only a new couple can be, and so we met up, at my house, at about ten in the morning, instead of both heading to our offices after morning meetings. It was cold, I remember that, mid-February, and the heat was down on my house—it always went down to 62 during the day—so we were cuddling, petting, naked, under the down comforter.
Her hands were touching my neck, my chest, my stomach, teasing me, playing with me, moving lower, until they were wrapped around my penis. And that’s when she said it.
“Oh, it’s so small.” She said it in surprise, I assume expecting to find a throbbing erection between my legs, not a limp penis, a flaccid penis, a soft, tender, almost girlish organ.
“I…I’m sorry,” I mumbled, mortified to have my penis referred to as small, “it…it’s cold.”
“It’s okay,” she kissed me, “I like cute, soft things.” Now this was before she knew about Sara, before she knew that I was a sissy, before everything.
2. “Wait, you didn’t, um…already?”
Cum already. That’s what she was asking, that was the point of the other question. That one too was early in our relationship, naked, in bed, in my room, music in the background. I was horny that day, very much so, and literally, within seconds of entering her, I was splurting cum all over her, inside her, having an orgasm after ten, maybe fifteen seconds of fucking her.
She was polite about that too, stroking my hair, telling me it was okay, telling me that she enjoyed it, that it was okay, lots of guys just didn’t last very long.
Lie, lie, lie.
She didn’t enjoy it—the sex lasted about fifteen seconds!
It wasn’t okay—I exploded after barely entering her.
And dammit, almost ALL guys last longer than that!
Did her comments bother me? A little, yes, but you must remember something, deep inside, I’m a sissy. Even then, even when pretending to be a boy, even with a woman, who at the time had no idea, I was still a sissy, through and through.
Of course hearing that I’m small bothered me—but it also turned me on like nothing else.
Of course cumming so quickly, so prematurely, bothered me—but it did tip Emily off to an undeniable truth—THAT I AM NOT A MAN.
Why do I bring this up?
“It’s so small.”
Why do I want to tell you about this?
“Did you really cum already?”
Because of two recordings my friend Lisa Norman sent me.
You see, Lisa and I were chatting the other day about erotic hypnosis (remember she has that site, Clippette, that sells things like that. (Lisa also has Backseam and Backseam Extreme, two free Tumblr sites I adore.)
Anyway, Lisa didn’t know what one of the hypnosis MP3’s was about, one named “Hair Trigger Cock.”
“Um,” I told her, “Hair Trigger Cock plays on a sissy’s, um, often all too realistic fears, and I suppose fantasies, about premature ejaculation, you know, cumming too quickly to, um, please a woman like a real man does.”
“Oh,” she said, suddenly understanding. “That…that’s an issue?”
“Yea,” I said softly.
“For…for you guys,” she asked, sensing my tone.
“Sometimes,” I lied, quickly correcting myself. “Lots of times.
“Will you listen to it,” Lisa asked softly.
I looked it up on her website—Jenny DeMilo’s portion of it, scrolling down, saw another recording that caught my eye, too—Your Shrinking Cock. “God, Lisa, which one of you is TRYING to fuck with me?”
“What do you mean?”
“That’s like pushing my emasculation buttons…a small penis (I refuse to call my penis a cock), premature ejaculation, throw in feminization and that’s the trifecta of why I fantasize about Emily cuckolding me.”
“You…you want to listen to them,” Lisa asked.
“No,” I answered right away.
She didn’t respond. She didn’t need to. She knew better.
“Fine,” I said after thirty seconds of silence. “I’ll listen to them.”
“You don’t have to, Sara,” Lisa laughed, fucking knowing that I WAS going to listen to them, how could I not?
“Just email them to me…please…”
“Want to write a review, too,” Lisa asked, again knowing that once I got my hot little paws on something so kinky from Jenny DeMilo that I’d HAVE to write a review.
“Fine, fine,” I said, already refreshing my email ten times looking for the two MP3’s so I could listen to Ms. DeMilo’s nasty words, which I knew would tell me over and over again how small I was, how inadequate I was, and by implication, why my Emily wants, NEEDS to fuck a real man.
Soooo…I got them…and listened to them…and…
Your Shrinking Cock
Details: A professionally recorded, 12 minutes 58 second MP3 featuring erotic hypnosis with a focus on mentally transforming a pathetic penis into a girl clit. Ms. DeMilo uses her hypnotic voice and subliminal triggers to make you obsessed with having a small, penis, a clit.
Price: $15.99
Available here
My thoughts: A 2:15 or so induction, which uses multilayered voices and music to help put the listener into a hypnotic trance, to relax the listener for what’s to come. I love the layers, the subtle voices in the background, which, if properly listened to, do what they are supposed to—relax the listener for the true lesson.
It’s a fascinating start, one that rings true for me, one that rings true, I think for almost all cuckolds—worrying about whether we’re big enough (no) and whether we can please a woman (Ha!). Ms. DeMilo’s lovely voice tells you that you worry about your cock size all the time, whether it’s big enough, and that you can’t resist measuring yourself, all the time.
Okay, if ANY of you reading this say you have not measured yourselves, you’re a bunch of LYING BITCHES! Come on, I fucking KNOW you’ve done that, I KNOW you’ve gotten out a tape measure and figured out how long you are (I’m about five inches, erect) and how thick you are (um, I’m not), and tried to figure out how you measure up compared to the “average man” (um, I don’t).
Okay, at about 4:49 into the recording, Ms. DeMilo turns up the heat, hypnotically telling you that you get excited when your penis shrinks, that you get aroused seeing your penis shrinking, inch by inch, that you get excited as you slowly and deliberately shrink, getting small and smaller and smaller, that you become VERY excited and VERY aroused as your penis shrinks.
Well fuck me silly! What kind of guy gets excited at that? (um, sissies).
What kind of guy WANTS to have a smaller penis (didn’t you hear me—sissies).
What kind of guy gets aroused when his new girlfriend tells him his penis is small (yea, that was me).
What kind of guy (sissy, sissy, sissy), wants a small penis so he can wear the small chastity cage? (Me, yes, dammit, me, me, me!)
What kind of guy tucks his penis in his panties so his beautiful wife can ogle his small, little, soft, mound? (Sara does, Sara does.)
Watching it get smaller day by day, week by week.
Ms. DeMilo: The smaller your cock gets, the more excited you’ll become.
She hits it, right there, hits on the uniqueness of a sissy’s thoughts. Men WANT to have big, thick cocks to please women. I want that, too. I mean, not for me, of course, but for a man. Don’t you see, I want YOU to have a big, thick cock to please a woman, my woman.
“A cock so small, it’s not a cock at all, but a clit.”
Yea, that’s what Ms. DeMilo says, and when she does, that’s what gets me, that’s what grabs me, that’s what touches me, mentally, the thought of a small penis, a tiny penis, a boy clit, a penis that’s WORTHLESS for pleasing a woman.
I thought about that during the hypnosis, in my relaxed state. Do you know how often I think about the same thing when I’m with Emily? How often, you ask? Every. Single. Time.
Don’t you understand now why I bought her a dildo? Don’t you understand why I use it on her every time I’m in bed with her? Because it’s bigger than me, because I know it fills her better than I do, because I know it makes her cum harder—much harder—than I ever do.
Ms. DeMilo does. She know, she really knows how excited a sissy gets having not a cock, not a man’s cock, but a clit, a small nub, a tiny, useless, shrinking little thing.
Trust me, my pretty sissy girlfriends, like me, listening to Ms. DeMilo, you’ll get hot and excited and fucking turned on at the mere thought of having a tiny, worthless penis.
Which goes hand in hand with:
Hair Trigger Cock
Details: A professionally recorded, 15 minutes 8 second MP3 featuring erotic hypnosis with a focus on mentally transforming you so you can’t control your premature ejaculation.
Price: $19.99
Available here
My thoughts: Well, if you have a small penis, at least you can do something with it, at least you can please her if you can last a long time, last long enough to make her cum, right?
NOT AFTER YOU LISTEN TO THIS ONE, SISSY!
Right off the bat, right during the hypnotic induction, Ms. DeMilo makes you start thinking the many ways you’re inadequate, the many ways you can’t control your sexual impulses.
Thinking of them already? What are they, sissy? How are you inadequate? Can you count the ways with me?
1. We’re not men
2. We’re sissies
3. We have small penises
4. We can’t please a woman, sexually, like a man
5. We masturbate way too often
6. We cum way, way too quickly
Starting to see a theme, here?
Are you like me? Do you get aroused by pretty women? Uncontrollably excited? Like, beta male, babbling, hopelessly excited?
Yea, that’s what I thought.
Ms. DeMilo knows this and takes you farther into humiliation, takes you deeper into a dark, scary place, somewhere where just seeing a pretty girl makes you spontaneously cum in your pants (or panties).
Imagine, sissy, cumming just thinking of a pretty woman’s lips wrapped around your tiny clit. Women look for strong, masculine, men that can fuck them like a dog, and you, sissy, you’re so weak and feminine and pathetic, you cum just looking, you cum before she kisses you, let alone before she touches you, and good heavens, before she could fuck you.
What’s she think about you? You’re small and you cum without even being touched? Do you blame her for fantasizing about a real man, for fantasizing about a REAL MAN fucking her. Why would you? If you love her, you should WANT her to find sexual satisfaction.
Understand, I don’t want Emily to become EMOTIONALLY attached to a guy, no, no, her love, her feelings, those are mutually exclusive to us. But physical attachment is another matter altogether. I can’t make her cum when I fuck her, why wouldn’t I want her to find that with a man. Don’t you see, I want that BECAUSE I LOVE HER!
Every time I cum inside her I KNOW I’m being selfish because I cum at the expense of her pleasure. But you know what? She’s okay with that. Seriously. She’s okay because she loves me as much as I love her. As long as I can pleasure her with my mouth and with a dildo, she’s okay.
“Don’t you miss it,” I used to ask her.
“No,” she would answer, lying. Until one day she told the truth.
“Don’t you miss it?”
“Yes,” she whispered, looking away.
And then I knew, instantly, one day I’d be her cuckold.
At about 6:00 minutes into the recording, Ms. DeMilo tells you that you know what women think about you, what they can sense about you, that you’re a loser, that you’re inept, sexually, that you’re not a man, that they can smell what a loser you are.
Have truer words ever been spoken???
Listen, I’m not saying that there is no hope for a small, sexually inadequate, sissy. I’m not saying that at all. What I’m saying is that do an experiment, approach a group of women, a group of pretty, sexy, available women, and tell me if it isn’t obvious on their faces, every one of them, that they KNOW you’re not an alpha man.
Go ahead.
They know, sissy, they know you have a hair trigger cock.
They. Just. Know.
So fucking embrace it, sissy, you’re not a real man, you’re a cum leaking loser.
Maybe that sounds harsh—I know, it does. But imagine it whispered in your ear from the woman you’re married to, the woman who truly loves you, imagine her whispering it in your ear as she takes your panty covered clit in her hands and strokes you and speaks. “It’s okay, cum for me pretty girl, don’t worry about fucking me, that’s what he’s for, just be my soft, pretty girl.”
Guess what? Every fucking one of you would cum in an instant! Just like me. Just like I do in Emily’s hands.
Ms. DeMilo reinforces this throughout the MP3, remaining you that you’ll do that, you’ll cum early, cum fast, cum before it’s over, time and time again, every time, every single time.
Here’s a line that really, really got me: As the excitement and anticipation builds, you know it’s over before it even starts, you know you can’t control yourself, and you will cum early.
I know this. I. Know. This. I think about this every time I’m intimate with Emily. I think about how quickly it will be over, so I do something men don’t do. I don’t worry about it. Odd, huh? Knowing how quickly I will cum, I instead focus on Emily exclusively. I lick her for hours. I touch her. I massage her. And I use the dildo on her. I do this to make her cum again and again and again. I want her to find pleasure—and if she can’t with my little penis, she sure can with my hand, mouth, and toys.
So you see how these go together? You see how they reinforce my notions of being a sissy, my emasculation, my feminization.
Men have hard, thick, long lasting cocks.
Sissies have soft, small, hair trigger clots.
It’s time you really come to understand that, because every woman you meet understands it, judges you on it. You’ll never be a long-lasting lover, no, you’ll always be that feminized guy with the small penis who cubs too soon.
So embrace it. Let her embrace it, too.
After all, we all have our roles to play, sissies!
Emily is the love of my life.
I'm her sissy cuckold.
And Evan is the man who fucks her.
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