by John Dylena
I told him about my collar and the knock-off chastity cage I owned, and he told me how hot it was making him. I told him about my submission fetish and how I wanted to wear my slutty schoolgirl outfit and let him dominate me.
I felt the blood rush to my cheeks. I shifted in my seat, my cock hardening as I typed.
[Me]: I have this fantasy in my head.
[Monica]: oh? Do tell.
[Me]: I’m in my slutty schoolgirl outfit. Wearing my collar and chastity cage. I’m in a room with you. You’re wearing a sexy leather outfit and holding onto a chain leash that’s clipped to my collar.
User “Monica” has changed their name to “Mistress.”
[Mistress]: Oh I like that. And I’ll do more. I’d press you against a wall. Hold your hands above your head with my left hand as I slip my right into your panties.
I leaned back into my chair and bit my hand. My cock was fighting to burst through my jeans. It was so hard it hurt. My apartment was quiet, so I opened the door and silently snuck about, searching for any signs of my roommates.
Both their rooms were dark, and the apartment was empty. I called out to them, and there was no reply. It was a Friday night, and as such, they must have been out partying.
I ran back to my room. My friend hadn’t said anything else. I bent over my chair and quickly typed in a response.
[Me]: (hey, roommates are gone. Have the place to myself. Going to get dressed. Gimme a moment.)
I hovered over my keyboard and bit my lip. I saw the notification that my chat partner was writing.
[Mistress]: (hurry up slut! I’m already wearing my panties and I’m so fucking hard).
I slipped out of my pants and threw off my shirt. I pulled my boxers off and tossed my garments onto my bed. Looking down, I stared at my fully erect cock. I touched my finger to the tip and bit my lip as I watched a string of precum follow it as I pull it away.
I stepped into a pair of panties and my stockings and returned to the chat. Monica—or now “Mistress”—and I went back and forth until it got was too difficult to focus. I couldn’t touch my cock until I got permission to.
I looked down and saw pearls of precum form and slowly ooze down my shaft into my panties.
[Me]: please Mistress let me cum.
[Mistress]: not yet slut. You need to make me cum first.
I swallowed as I did my best to type out the scenario of me sucking his cock. I put as much detail as I could of how I would look up into his eyes as I licked his shaft and kiss the head; how I would slowly stroke it as I caressed his balls.
My fingers froze. I couldn’t type anymore. I stomped my feet and moaned loudly. My cock twitched and throbbed. I was so close. So very close.
[Mistress]: ahhh, that was nice. You’ve been a good slut and now you can touch yourself. Go ahead and cum as you scream my name.
I didn’t need to be told twice.
[Me]: Yes, Mistress. Thank you, Mistress.
I grabbed a couple tissues as I slouched in my chair and grabbed my cock. All it took was a couple strokes and a throaty moan before I orgasmed.
I closed my eyes and groaned loudly as my entire body shook. The orgasm was powerful, and I felt my cum surge out of my cock and splash onto my chest and stomach.
My heart pounded. My body was burning. Sweat poured down my brow. I was lightheaded and dizzy. I looked down at my now flaccid cock and I dragged my fingers across one of the streaks of sticky cum on my smooth, hairless chest.
Then I heard the sound I most dreaded hearing.
The color from my face vanished as I heard the front door open and close. I scrambled onto my feet to close my bedroom door, otherwise my roommates would’ve seen me sitting there in my panties and stockings, cock out and cum all over my chest and stomach.
I managed to close the door before they could see me and returned to my keyboard.
User “Mistress” has changed their name to “Monica.”
[Me:] Heh, blew my load all over my stomach and chest then I had to close my door before my roommates saw me.
[Monica]: I would love to catch you like that, so I could punish you for being naughty. ;)
I laughed as I wiped the cum from my body and stripped out of my clothes.
[Me]: Ugh, I’m wiped. Going to shower than go to bed.
[Monica]: Good night! *kiss*
I remained at my computer, staring at the black screen for another minute or two after turning it off. My mind raced. I had never had that powerful of an orgasm from masturbation.
I looked down at my hand and over at the area in my closet where I stashed my collection of lingerie, outfits, toys, and high heels. My sexuality was indeed changing. A year ago, I would’ve never considered having a roleplay sex session like that in a chatroom.
Then again, a year ago, I didn’t have any women’s clothes of my own. It was only a month after I started working that I began buying the clothes and hiding them in my closet. It was much harder back then, as I still lived with my parents.
My roommates were loud, and they weren’t alone. I heard the voices of two women and another man. I recognized them instantly, and as I dragged my tired body to the bathroom, I silently prayed that they would move the party elsewhere.
Things became quiet between me and Monica. After our night of rather intense erotic roleplay, our conversations were few and far between. Work kept me and him busy, and when I came home, he would either be offline or away. When I finally heard from him again, it was that he would be gone for a week on vacation and that he wouldn’t have internet where he was going.
The night before he was leaving, I was dragged away from my computer by my roommates. It was a Friday night, and they were intent on getting me out of the apartment and trying to hook me up with one of their lady friends. It was strange. As I opened my mouth to plead and protest my friends’ plan, I realized that I was fighting to stay in my room to have cybersex with not only another man, but a crossdresser, as well.
Could this “relationship” be more than that I thought it was? Could I actually have feelings for the stranger who didn’t even live in the same state as me and was almost ten years older than I? Though you wouldn’t have known that from looking at his pictures. For someone in their mid-thirties, Monica looked damn good.
[Me]: Sorry Monica, but I can’t chat tonight. Going out with my roommates. :(
I could feel my heart pounding in my chest as I waited for his reply. For a good minute, there was nothing but silence. I bit my hand as I panicked. Had I said something that offended him? Did I totally ruin the relationship we had?
At length, the notification appeared and his reply shortly after.
[Monica]: That’s fine. You have fun okay? I’ll email you something fun later. Good bye! *kiss*
Before I could wish him goodbye, he logged off, and my heart sank.
The thought stuck with me as I followed my roommates out of the apartment and over to their friend’s place. The house was packed, and liquor of every brand and type was being served. Despite the extravagance of the event, I couldn’t bring myself to enjoy it. The women were beautiful and wore high heels and short dresses. Even so, none of them showed any interest in me. Any attempt at a conversation ended with a friend of theirs would pull them away to the dance floor or they saw someone else.
With my roommates nowhere to be found and my attempts at engaging with one of the many gorgeous women shot down fast and hard, I made my way out of the mansion and into a cab back to my place.
Even though I was alone for quite possibly the rest of the night, I had no desire to dress up, no desire to look up some porn and masturbate. I totally forgot about the email that Monica said would be in my inbox as I took a six pack of beer out of the fridge and watched Netflix until I fell asleep on the couch.
When I woke up, I was still alone. There were four empty beers and a half-drunk fifth. My phone was silent. The sun was shining bright, and without even looking at the clock, I got up and stumbled out of the
apartment to the diner across the street. I wasn’t hung-over, but a greasy breakfast with a hot cup of coffee still sounded really good.
I woke my computer from its sleep and opened up my email. There waiting for me at the very top was the letter from Monica. I bit my lip as I opened it, worried that it would be him saying goodbye and ending our relationship because I had done something wrong.
It was the total opposite.
Monica opened up to me. He told me about himself, his sexuality, his interests. He told me about his history and past partners. He told me how much fun he’d had chatting with me and how much pleasure it brought him. He also told me how torturous this vacation would be because he wouldn’t be able to chat with me directly.
He also gave me instructions.
In the past, I had told him about how I had a PO Box, and when he asked me for the address, I gave it to him without thinking anything about it. In this email, he told me that he was sending me a package and not to open it until he returned from his trip. My cock hardened instantly as I read the final instructions.
You are not allowed to cum. The first day I am gone, you are to edge completely naked. The second day, you are to edge wearing panties. Third day is panties and stockings. Fourth is previous day plus heels. Then bra. Sixth day, you put on a miniskirt. Seventh day, everything including your collar and hot pink lipstick. I want pictures with timestamps.
I repeat. You are not allowed to cum. Not until the eighth day when I return and you open your package.
— Mistress
“Holy shit,” I said as I slouched in my chair. I bit my fist and groaned as my cock pressed against the material of my jeans. I grabbed my phone and texted my roommates. It was still early, and I doubt they would even be awake, but I wanted to make sure.
The response I got was barely legible, and after deciphering it, I learned what I already knew: they wouldn’t be back for hours. Monica’s letter got me aroused, and I just had to do it now. I’d edged before, but this… this was something entirely new. Would I be able to pull it off and edge for a week? How bad would the blue balls get?
I immediately stripped naked. My body was still silky smooth from when I’d shaved last, and I scribbled the time and date and took a picture of me from the chest down on my phone. It was the only camera I had. My webcam, as much of a piece of crap as it was, broke a month ago, and I had yet to get a replacement.
It was strange seeing myself naked on my phone. Even more so when I realized how rock hard I was when I took the picture. Pushing the thoughts aside, I put a little dollop of baby oil on my hand and started stroking.
It was harder and harder each day, especially on the fourth day when I fapped in my pink panties, white stockings, and pink heels. Edging only temporarily relieves the lust that builds up inside you, and when it comes back, it’s hotter and stronger than ever. For days now, I’d been edging, and my thoughts were overrun by my lust. All day, I had to fight the urge to let myself go.
There was a slip in my PO Box, as there always was when I got a package. As I stood in line waiting to get whatever it was that Monica had sent to me, my eyes focused on the woman ahead of me in line. She was tall, with long blonde hair and a black skirt suit. She wore shiny black pumps, and I could smell her perfume.
It was intoxicating, and I lost control. My mind’s eye was filled with fantasies involving this not much older woman. I was tied up and gagged as she spanked me. Then she dressed me up like a slut and pegged me. Then her strap-on magically turned into a real cock and she made me suck it, and as I did, my body became female.
“Next!”
I shook my head and came back to Earth. I walked in a daze toward the counter as the blonde went to the other side. I shifted my pants to hide the erection as I handed the lady behind the counter the slip and told her my box number. She returned with a medium-sized box, and when I went to leave, I saw that the blonde was nowhere to be found.
I almost came on the seventh day.
I had gotten so riled up as I got dressed that I almost came instantly from touching my cock. Instead of my schoolgirl miniskirt, I went with a baby-pink ruffled skirt to go with my high heels and white stockings. I wore my pink panties from before, with a white bra and my black leather collar. My body was trembling as I stood in the bathroom and painted my lips that hot, slutty pink.
I had to sit there and stare at the computer screen and wait for my body to relax before I started stroking. I looked down at my slowly softening cock and took a deep breath. I had come so close. If I hadn’t bit into my hand, I would’ve cum right then and there. I had to finish this challenge. I looked over at the still sealed box. When enough time had passed, I grabbed my cock and edged for the seventh time.
Monica emailed me on day eight. I had been sending him the pictures every day like he’d told me to, but I had yet to hear from him until now. My entire body shook with nervous anticipation as I waited for him to log into Skype.
[Monica]: You were a good little slut, I see. I liked your pictures. They made me cum several times. I loved knowing that you were suffering. ;)
[Me]: Yeah, it was hard. Almost came one time, got pretty close most days and had to really distract myself to stop.
[Monica]: Good girl. Are you ready for your presents?
[Me]: Presents?! There’s more than one thing in that box?
[Monica]: A couple things. Go ahead and open it and tell me what you got.
My heart pounded in my chest and my fingers shook as I cut open the package and typed out what my friend had sent me: a brand new HD webcam, a silicone butt plug, lube, a gold heart collar that had “Monica’s Slut” etched into it, and a black fishnet bodystocking.
I was in disbelief. I couldn’t believe the stuff he had sent me. I was confused, turned on, excited… so many different emotions all at once.
[Monica]: You okay?
[Me]: Yeah just… little overwhelmed, that’s all.
[Monica]: Too much? I was afraid of that when I sent the stuff to you. I’m sorry. You can send it back if you’d like.
[Me]: No, don’t worry. I love it. Even the heart tag. ;)
[Monica]: Good, ‘cause there’s something I want you to do for me.
[Me]: what?
[Monica]: I got a matching webcam. I want to have a video chat session. No sound—unless you want to. Don’t have to show your face either. Just the neck down.
[Me]: Oh… oh wow that actually sounds really hot. But yeah, no face. Not yet. :(
[Monica]: That’s fine. But I have some orders for you.
I bit my lip as I read what he wrote. Monica wanted me to put on the bodystocking, along with my schoolgirl skirt, my red heels, and collar with the new tag added. Then he wanted to watch me insert the plug, and after that, we were going to have cybersex, and I’d finally be allowed to cum.
It must have been fate that this would happen on the same day that my roommates were both out of town. I would have the place all to myself until tomorrow. I told Monica this.
[Monica]: Hurry up and get dressed slut. I can’t wait to watch you cum.
I didn’t need to be told twice. I quickly stripped out of my clothes and put on the bodystocking, skirt, heels and collar—after attaching the new tag. Then I installed the new webcam, and once I’d positioned it so that it would only show my body, I sent Monica a video invite.
I had never been so nervous before. It felt like hours watching and waiting for him to accept, and the dial tone went straight to my brain. I tapped my fingers on the desk and let out a relived sigh when the video popped up.
Then I gasped and my dick hardened instantly.
Monica sat at his desk in the same manner as me. His webcam was also turned down. He waved before spreading his legs and showing me his cock, which was as hard as mine. He wore a matching bodystocking with black thigh-high boots and a corset.
User “Monica” has changed their name to “Mistress.”
[Mistress]: Looking good, slut.
[Me]
: Thank you, Mistress.
[Mistress]: Show me that collar.
I bent forward and brought the collar with the tag close to the camera so that he could see it.
[Mistress]: Very good. Are you ready to have some fun?
[Me]: I am!
[Mistress]: Then you know what to do. Show me that ass of yours and let’s see that plug disappear.
I let out a moan as the plug slowly slid in. I turned around and put my ass up by the webcam. Monica gave me the approval and I watched him slowly stroke his cock as we chatted some more. Our conversation quickly turned dirty and I masturbated for him.
I watched the screen and followed his orders. Speeding up and slowing down when told; stopping as well as starting back up. It was agonizing. I was so close to cumming for the first time in a week. But just as I was about to, he had me stop, and I wasn’t allowed to touch myself until he came.
Monica took his time. I could tell he was prolonging it, making me suffer. He told me afterward that he liked watching me squirm and seeing my cock twitch as he typed all kinds of dirty things into the chat, things like how he was picturing my lips around his cock as he stroked.
I leaned forward in my chair and watched his body spasm and the cum ooze out of his cock and splash onto his stomach and chest. He just sat there, reveling in the feeling that washed over him. I looked down at my own cock. It was twitching and throbbing, glistening precum oozing out of the tip.
He gave me the order, and I stroked until it hit me like a freight train. The force of his orgasm threw me back into my chair. My mind swam, and I became dizzy. A fog rolled over my eyes as I moaned and a week’s worth of cum erupted out of my dick. It flowed down the shaft and streaks of it went flying onto my chest and stomach.