Crossing The Line


Before last night I could still pretend that it was the idea that attracted me. Claim that it was the tabooness of the act that attracted me, not the fact that I was dressing up in girl clothes and fantasizing about being used by a group of men.

Last night it became real.

I'd posted ads on craigslist before, hit up grindr, the whole shebang, but dudes would always go silent right when they had to commit. Which sucks, because this sissy thing is a big secret for me and I try to commit. I make sure I'm smooth, I get all dolled up, slip a plug in so that I'm ready if something happens. And shaving my legs is a big deal. It means that I have to wear pants for the next two weeks because I'm not at a place in my life where I can explain that away.

But last night was different. It wasn't even that big of a thing compared to some stories I've read on here, but for me it was huge.

I found him through reddit on a BDSM-Personals page. I was just fantasizing. Sometimes pretending that you're going to do something, going onto personal pages and imagining yourself typing out replies, sending pictures of yourself... It's is hotter than anything you could watch. I hadn't even gone there with any real intent of finding anything, but as soon as I saw the name of my little city I froze.

That might sound strange, but you have to understand the way but my fantasizing over the past year and a half has stated trickling out into reality. I started grad school in the fall, which meant that I finally had enough money to afford my own place. And since I've started living on my own I've spent the majority of my time alone dressed up like a girl. That might not surprise you; you are, after all, reading a sissy confessional, but a lot of the time it wasn't even sexual. I'd just come home, slip into a skirt, fishnet stockings, and a cute pair of panties and watch Netflix or write my papers.

So when I saw that ad I was already dolled up. I was shaved, wearing the slutty outfit I've come to think of as my comfort clothes. The ad was simple enough. 'Daddy looking for local sissy to own'. The cursor hung over the ad for what felt like ages, my mind blank and buzzing. Buzzing because I no longer had to fantasize. I could turn it into my new reality.

It took him an hour or two to reply to me, but as soon as he did we were chatting. His name was Mark, and he was almost a decade older than me, which I didn't think I'd be into, but we had chemistry right from the bat. I don't know what it was. I guess just a good blend of being respectful and forceful. Some people get off to the humiliation aspect of this fetish, but that's not really for me. I'm not knocking it, I just want to be treated like a girl and get some cock, not be made to feel badly about it.

And that's how Mark made me feel.

So when he asked me if I was free that night I said yes. I wish I could say I hesitated. I didn't. Not even for a moment

I went over to his place. That alone was terrifying. He told me that he wanted me to be already done up and ready to go when I got there, so I put my boy clothes on over my sissy clothes, did some of my make-up (couldn't bring myself to do the lipstick though), tucked a wig into my backpack and hopped in my car.

The whole time I was freaking out. It was the first time I'd even gone outside with panties on, let alone a buttplug and skirt on. And even though they were under my clothes, I was hyper aware of them. I was hugging the speed limit the whole time, imagining cops pulling me over and thinking I was some kind of pervert, or getting to an accident, being taken to the hospital and then having my family find out that I like to drive around in tight thongs.

My brain kept telling me to turn back, but before I knew it I was parking the car in front of a house in the wealthier part of town, gripping the steering wheel with white knuckles and hardly breathing.

That's when it first started becoming a reality for me. When it really started sinking in. I was going through with this. The backyard was dark, almost pitch black aside from these LED strip lights that lined the garden. I closed the gate behind me as quietly as I could and slipped my boy clothes off, straining my ears the whole time. The windows were dark, and the street was silent.

My outfit wasn't super slutty: fishnet stockings, a halter top and a stuffed bra, and a pleated skirt. I like wearing heels at home, but I'm really bad at actually walking in them, so I stuck with flats and shuffled my way over to the door. I knocked gently, but to me they sounded like gunshots, like they were loud enough to wake the neighbors, have them throw their lights on to see what all the ruckus was about.

I was straight up scared. Standing in the darkness dressed like a girl at a music festival, waiting for some random guy that for all I knew, just wanted to rob me. I heard the lock clacking and I put my wig on, tried to stand up a little straighter. Even though my heart was beating out of my chest, my cock was already hard, rubbing against my frilly panties.

He answered the door with the biggest smile on his face. Looking me up and down with these hungry eyes. I don't think I've ever had a woman stare at me like that before, because his face was all lust. He didn't even have to touch me or say anything. The fear was gone. I knew right then that I'd do what he told me to.

He led me right into the living room, offered me a beer and sat down. I freaked out a little bit then and went to the washroom just to compose myself, making sure all my clothing was set right and throwing on my lipstick.

The last thing I wanted to do was sit and chat. I wanted to get straight to it, but I didn't know how to make the right move. How to get things rolling. I knew what I wanted to do, but that meant admitting to another human that I was a sissy. That I actually wanted cock. I couldn't keep pretending that it was only a fantasy. It might seem silly, I mean, the guy had opened the door to find me dressed like a girl with a buttplug in my ass, but I still hadn't said it. That made a difference. I was getting closer to that line in the sand, but I wasn't there yet.

Thankfully, Mark made that easy for me. I walked into the living room and he walked right up to me, lifted my chin toward his, and kissed me. It took me by surprise, but I sank right into it. His stubble grinded against my cheek, his breath tasted like mint and whiskey. Slow and gentle at first. Probing, but not hesitant.

I never thought I'd be into that. If you asked me a week ago, I would have told you that I was only attracted to the idea of cock, not the man behind it. I couldn't even bring myself to watch bi porn, because you could see their faces. I thought that was because I only wanted the cock as a sexual object.

That's what I thought. But I melted into him. He pushed his tongue into my mouth, and I don't think I've ever felt my cock get so hard so quickly. It wasn't just the kiss, it was the way he pulled me into him, one hand on my hip, the other at the back of my neck. I could feel his cock pressing through his jeans, rubbing against my tummy. I think I even whimpered a bit.

Then he pulled back, held my head so that I was looking at him, and said "Are you going to be a good girl for me tonight?"

I don't know why I said it, but apparently everything I thought I knew about my sexual preferences was wrong. "Yes Daddy, I'll be good for you," I said. I never understood the allure of that word, but when I said it I even pitched my voice higher so that it would sound girly. It felt so naughty, so dirty. And I loved it.

But he just smiled and pulled me in for another kiss. A bit rougher this time, biting my lip playfully, the hand on my hip drifting down to my ass and under my skirt, feeling my smooth legs, stopping briefly to feel the outline of my buttplug pressing against my thong.

I decided to be a little rougher too. I leaned into him and went for his belt, unbuckling it quickly, trying to move faster than the tinge of doubt growing in my mind, plunging my hand into his pants and rubbing his cock. It was big, warm, and already rock hard. And it just felt so right in my hands.

He tilted his head back and groaned. "That's a good girl," he said, giving my ass a little spank. I almost came in my panties right then. I wasn't even touching my cock, but every little sensation was running through my body like jolts of electricity, thoughts going out of tune as I wrapped my hands tighter around his cock and leaned in closer, my lips parted, waiting for his tongue to push its way into my mouth. My back arched, I pressed myself into him and started biting gently at his neck as I stroked him with both hands.

He moved back to the couch, pulled his pants and boxers off and tossed them to the side. "Crawl over to me like a good slut," he said, leaning back on his elbows.

So I did. I got down on my knees and I crawled, sticking my ass in the air and biting my lip. The memory of it is so ridiculous that I'm cringing a bit even thinking of it, but at the time I was just so into it that I couldn't even question what I was doing. I felt so sexy, like my role had totally absorbed me. Because I had crossed that line. Committed myself to a new reality. I wasn't pretending to be a slut. I was one.

My eyes were fixed on his cock the whole time. The carpet bit into my knees, my cock strained against my panties, and I crawled. I wanted to feel him cumming in my mouth, pushing my face down all the way until I gagged and my mascara ran down my face. When I got to him he didn't grab my head, or even tell me what to do. Just looked at me with this sideways smile and let me figure it out on my own.

Sucking a real cock is nothing like practicing on a dildo. The real thing is so much warmer. The tastes, even the smells, the unpredictability of the way he'd move under me, it all just drove me wild. And I wasn't just sucking his cock, I was also licking his balls, kissing his stomach, working him with my hands.

I would have rimmed him if he asked me to. My tongue probed there a few times, each time hoping that he'd lift his hips just a little. I've masturbated four times since last night, and each time I've imagined him doing just that. Or just pushing my face lower and letting me figure out what he wanted, the whole time looking at me with that crooked smile of his.

My lips were tingling, tears were welling in my eyes, I felt my face flushing as I bobbed up and down. I balanced myself on one hand, the other drifting between my legs. I didn't take my cock out of my panties (even hard, I'm only around 5 inches, so it wasn't that hard), but I did stroke myself. Rubbing in small circles just like I would if I had a clit.

After a few minutes he got me to turn around. My heart stopped. I thought he was going to fuck me. We hadn't talked about that, but he might be taking the buttplug as a sign that I wanted it. And I didn't know if he was wrong. I turned slowly, some growing part of my hoping that he'd pull my panties aside, that I'd feel him grinding against my ass.

But he didn't move from the couch. He just pulled me closer so that my ass was in the air toward him, and slowly pushed my head back toward his cock. I took him back in my mouth eagerly. Like I couldn't wait another second for it, and while I sucked him off he spanked my ass, played with my buttplug. He eve rubbed my balls through my panties. But he never touched my cock. For some reason that was so hot.

It didn't last long. After a few more minutes, when my lips were tingling so bad that half my face was numb and my tongue felt like it had ran a marathon, he grabbed my head and slowed me down, twisting my head gently so that I was looking him in the eye.

"You ever taste cum before?" he asked. His face was flushed, that crooked smile still there.

"No Daddy," I said, trying to use that high pitched voice. It wasn't really true; I'd eaten my own cum a few times before, but that wasn't the same. And it wasn't really me. I was an alter ego. A girl. A slut. And she'd never tasted cum before.

But she was about to.

"I'm gunna cum soon," he said with a strained voice. Crackly. Like each word took effort. "Are you going to keep being a good girl?"

I nodded, keeping his cock in my mouth the whole time, drool running from the corners of my mouth.

"Say it."

I took his cock out, holding it, right in front of my mouth. "Please Daddy, cum in my slutty mouth. I want it so bad."

He grabbed my head again, pushing me down on his cock. Soon he was grunting, holding my head in place and pounding my face.

I told myself that I'd swallow it all. And I really wanted to, but I just wasn't ready for it. It was way thicker than I thought it would be, but the taste drove me wild. And there was so much, spurting into my mouth, overflowing, spilling out onto my red lips. I was bucking my hips as he came in my mouth, grinding my cock against the side of his couch like a girl in heat. Most of his cum spilled out my mouth before I could swallow, dribbling down my shirt and onto the sofa, but I did get some.

That was okay. I'll do better next time.

I felt his entire body relax as he groaned, and I licked his cock gently as the last of his orgasm convulsed out of him. Then I surprised myself again. I crawled up on the couch beside him, him half naked, me wearing ruffled girl clothes, and cuddled up next to him. He put his arm around me and pulled me close. I could feel his heart beating, feel the deep breaths coming out of him, and my cock was still throbbing hard, pressing up against his warm thigh.

It only lasted a few minutes. I wanted this to be a casual thing, and I needed some time to think about what had happened, so I told him that I was leaving. I think he would have let me stay, but that was too much. As fun as this was, I still wanted to take things one step at a time.

But I think the sluttiest thing I did that night came right there at the end.

He offered to let me clean myself up. I said no. I kept my girl clothes on, kept the remnants of his cum on my face, and I walked to my car. It was almost four in the morning, and the entire drive home I was rubbing my cock, smearing the remnants of his cum on my cheeks, remembering how it felt when he first took me.

I was still imagining cops pulling me over, but this time they liked what they saw.

When I finally got home I jacked off three times in a row, and I still haven't gotten back into boy clothes. I'll have to change for my shift at work tomorrow, but I might keep the panties on.

No one will know.

Report Story

bygroundhogsarethebest© 4 comments/ 27147 views/ 22 favorites

Share the love

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Favorite Author Favorite Story

heartflubatty88, cmoney637 and 20 other people favorited this story! 

by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by MarieJoanne10/03/18


I too have had similar fantasies xxx Marie

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by mm3221710/03/18

Hope to see the next installment!!!

Great job. Your writing style is easy to read. As it progressed, you seem to have touched on many of the inner feelings that harmonize with my own limited experiences. I am very much looking forwardmore...

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by cdmonica08/13/18

Lucky girl

A great beginning. I have felt many of the same emotions and I love it every time. I hope to read more from you and I hope you can expand on your journey to girlhood.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by 300bowler30008/09/18



If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All 4 User Comments  or
Click here to leave your own comment on this submission!

Add a

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

Refresh ImageYou may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar: