Good Girl: Two Words That Got Me Into Feminizing Men

You know that moment when you realize something about another person, and you gain new insight into who they really are--as if the last piece of the puzzle fell into place and you finally understood what they truly wanted?

I had two of those moments with Tom, and the second one took our dynamic and my interests to a whole new level.

I met Tom on a dating app. I wasn't looking for anything serious, nor was I looking for a submissive, but I had just gotten out of a relationship and was horny.

Tom was 30, worked in finance, was attractive, and alluded to Succession in his profile--my favorite show; I "liked" him. A day or so later I noticed he matched with me and had sent me a message asking me to have lunch. I liked that he didn't waste time and wasn't trying to drag out text conversations. However, I was going out of town that day, but I told him to text me.

Moment One:

Our conversations had been flirty from the start--I mean, we were both looking for something casual, so why wait to size him up and see what he's into?

When he said, "I guess I'll have to wait to take you to lunch then," I smirked and replied, "Yep. Think you can handle waiting?"

He didn’t hesitate, "I can wait. I like being teased."

At that moment, I smiled and *just knew* he was submissive. But I wanted to push him further to *really* see if my assumption was correct.

I texted him back, "I like to tease. Can't wait to have you on your knees begging".

He didn't like it. He loved it. He was no longer just a hook up, he was *my* sub.

I knew he liked teasing, but what else? Over the next few months, I pushed him further, testing his limits and seeing just how far he'd go.

I remembered our first time having sex--squatting on his thick, at least 7 or 8 inch cock, with my feet at his side. His hands gripped my foot and pulled it toward his face to kiss. It probably seems trivial, but I knew. He liked feet.

The next time I saw him, the moment he walked in the door I had him on his knees, waiting for my next instruction. He looked up at me like a sad puppy dog. If you read about [the first time I dominated a man](https://fetlife.com/sissypegger/posts/12144191), I've seen this exact look before. A look of pure submission, eyes fixated on me, mouth hanging open in amazement. I had him kiss my feet, giving each one the attention they deserve. I then shoved my foot in his face, and later down his throat.

I remember asking him if he had been jerking off, as I had instructed him not to. I owned his cock and he couldn't cum unless I made him. He was a good boy and hadn’t. And it wasn't just talk, he would regularly share with me that he hadn't came in "X" amount of days; he had a goal. If there’s one quality I appreciate in a man, it’s discipline. Then he suggested that being locked away in a chastity cage with me holding the key might be a good idea.

I had him order one of my choosing.

Me agreeing to holding the keys to his ability to cum seemed to have unlocked something in him, and broke down any fear of judgement or hesitation he had about sharing his naughty desires with me.

I told him I wanted to peg him, unsure of how he would respond. He was submissive, but did he want me to penetrate his sacred-one-and-only man-hole?

He was texting me as he was walking home from work, and said he was so hard at the thought of it. From there, the floodgates opened:

He told me he wanted me to train him to cum from anal only.

He said he couldn’t wait for the day I could fist his asshole.

He wanted to be used and feel like a slut.

He agreed to me picking out his outfits for the day, and he sent photos of him at work wearing them.

He sent me a photo of all the toys he had:

-A gimp mask

-A milking table

-A sex machine

-Butt plugs

-A dildo

Most of it, he admitted, he had bought on impulse and never even used. I found it amusing that he had gone on a shopping spree for kinky toys but hadn’t actually explored half of it. But more than that, I was intrigued. His sexual openness and ability to spend money meant I could push him as far as I wanted. Now, he wasn’t just a hookup, and he wasn’t just a sub--he was an outlet for me to explore any sexual fantasy I desired.

My previous boyfriends and hookups had all been vanilla--predictable, routine, and devoid of the kind of power play that actually excited me.

Anything I wanted to do, Tom loved:

-Choking him

-Restraining him to my bed

-Riding his face--with a strap on

-Spitting in his mouth and on his face

-Having him eat his cum

-Slapping his face

-Squishing and pulling on his balls--the harder, the better

-Riding his cock with a dildo also in my pussy, as he held a vibrator on my clit

Moment 2:

I saw Tom at least once a week, sometimes more if I wanted. And when I wanted to see him, he'd be at my place at the time I told him to be. The first time I saw him after our intense conversation I was ready to fill his ass up with my strap on--and so was he.

We had a routine: he would enter my apartment, wash his nasty little hands and strip naked. He walked over in front of my floor length mirror, ass plugged, and got on all fours.

I kicked his big, cum filled balls.

Spanked them with my paddle.

Sat on his back, making him watch me use him like the object he was--and desperately wanted to be.

I got up and went into my room to grab the strap on.

He confessed before that other women had kicked his balls and choked him before, but he had never sucked on a strap-on or been pegged. I had already instructed him to practice deep-throating and work his way up to larger butt plugs. Now, it was time for the test.

I walked over, him still on all-fours, standing in front of my mirror. I moved to the side so we could both see each other in the mirror; I like to watch. I told him to spit on it, because what's a blow job if it isn't wet and sloppy? He spit on it like he knew what he was doing. I told him to lick it up and down like a good whore. Then I went deep in his mouth.

He had a small mouth, but I knew he liked being stuffed. He wanted to be *my* slut, and sluts take every inch they're given; they're cock-hungry. And more importantly, I wanted him to take every inch. He gagged on that big, fat strap on but always went back for it. I think he even threw up in his mouth a little, but I kept thrusting and he kept sucking like the good whore I knew he aspired to be.

When I was satisfied, I led him to my bedroom. Restraints secured to my bed and my little submissive slut's wrists and ankles attached, I had him right where I wanted him: on his back, legs spread, and unable to move.

I took out the butt plug, and slowly crawled up his body until we were face-to-face. My pussy resting on his hard cock, I kissed and licked his lips slowly while gently grazing my fingers over his nipples, teasing him more than I ever had before.

I was so wet.

I asked him if he was ready for this cock.

He said he was.

I told him to beg for it.

He pleaded with me to fuck him, and I couldn't help but smile at his helplessness being tied up, hard, and eager to be filled up.

I pressed the tip of the strap on against his tight little hole, teasing him, making him wait. I even stopped to spit and lick his cock, knowing he wished I would suck it, just once.

When I finally starting fucking him, he couldn't help but moan. But halfway through pounding him and owning his ass, I asked him if he was going to be a good boy for me. His response?

**"I'm going to be a good girl".**

I kept fucking like nothing was out of the ordinary, but I thought, *A good girl?*. in that moment I knew he was a sissy.

He never alluded to wanting to be a sissy, but with him calling himself "a good girl" and wanting me to treat him like a slut, I knew I could push him further.

I had never even thought about a man wearing lingerie, let alone me being attracted to that. But one thing I did know, was that I was turned on by emasculating men, and what better way to do that than to have them look and act like a woman?

I loved the idea of this former hockey player--muscular, thick thighs, and by all means "dominant" in his *vanilla* life--stuffed in a bra, panties, and wearing stockings.

I texted him telling him I wanted him to get himself some lingerie so I could turn him into a true slut, and the next time I saw him I wanted him to give me a lap dance.

Not only did he respond asking what type of lingerie I wanted to see him in, he sent me a photo of him in silky panties he already owned, suggested he get waxed so he could be hair-free and "really girly", and thanked me for "leveling him up".

I was always one step ahead, and he fell right into place, just like I knew he would.

I loved turning a masculine man into a sissy--the power of stripping away his current identity and molding him into *my* perfect plaything. It ignited a deeper desire to explore that dynamic further.

Men who want to be sissies may have a deep desire to explore their feminine side, while some seek to project their own desires onto themselves. They don’t just want to lust; they want to *be* lusted after and become the object of desire. For others, it’s simply a dynamic of submission: a deep-seated need to give up control and feel used--and what better way to do that than by stripping away their masculinity, and breaking them down, and turning them into a slut whose only purpose is to please?

What was it that first sparked your interest in exploring your sissy side?