For the next few days, it was safe to say my anxiety was through the roof. Every notification, email and slight noise from my laptop sent me into a frenzy of confusion and a little bit of horniness. Someone had been recording my dress-up sessions through my webcam.
I had taped over it now and made sure that nothing could be seen. Everything I did online was careful, and I began using a VPN just for extra security. Sarina. Mistress, apparently. She already knew, though. Fuck.
My days were wrought with anxiety and fright, the knowledge of someone having videos of me doing that to myself scared me stiff. At night, however, I revelled in it. I began sleeping in panties, and my clit throbbed and ached at the mental images of someone knowing about my fuck sessions.
I was being watched and I loved it. The thought of a mistress, my mistress now, enjoying me fucking myself and drinking cum. Quietly I had always fantasized about being owned, but I’d never sought it out.
The first few nights I couldn’t sleep and I’d masturbate until I passed out. With my panties stained and sweat coating my body I’d drift off to images of a latex-clad bombshell forcing a strap on into me. I’d usually coat my lips with my cum, falling asleep with the taste lingering for the next day. I was a slut for someone who was blackmailing me.
This cycle of worry and lust continued for a week or so – I don’t remember that well as it was such a blur. And then I received another email. Tentatively, ignoring the class I was late for, I opened it.
Dear Kai,
My little pet. I can’t believe you’ve covered your camera! You will be punished for that.
I have decided to put your mind at ease – I want to meet you, in the flesh.
Attached is my address, as well as some instructions. See you Friday – 8 pm.
Ta ta for now
– Mistress Sarina
My heart stopped. Meet? In-person? I began sweating profusely, I couldn’t handle this. My whole body began shaking, and my little cock was rock hard. I’d dreamed of being owned – fucked and held as someone’s toy. Now it was a possibility.
I opened the attachment and memorized the address. It was only a twenty-minute walk from my house. Pretty convenient. The instructions below sent me into a frenzy though.
I expect you to be shaved, clean (inside and out) and come plugged. Failure to do so will result in the immediate release of your videos.
Speaking of the videos, you will have a chance to take home the only copies of them. This will be explained when you arrive.
My worries seemed to melt away at that point. I could get my videos and possibly have a new sexual experience? Although still slightly anxious – I didn’t know this person or trust them – this gave me a bit of solace. It was Wednesday now, so I had a day or so to prepare.
Thursday flew by, being busy with classes and a rush of thoughts about my predicament. When Friday hit, I skipped class and spent all day preparing. First, I ran a nice warm bath, with bubblegum body wash and fizzing bath salts to freshen up my skin. I then shaved, everything. My legs, arms, chest and ass, all completely hairless – even though they normally are, I took care to not miss a single spot.
After relaxing in the bath I pulled the plug and got out. I spent a good hour or so cleaning my insides, making sure I was ready for whatever the hell was going to happen. After cleaning I inserted my small buttplug. As soon as it teased my hole, my little cock stood to attention, and a bead of precum began running from my tip. I scooped it up with a finger and sucked greedily.
Plug in and shaved I sat down at my desk and applied some red lipstick and black mascara – simple makeup again. I brushed my long hair and sprayed some perfume to smell a bit girlier. I opened my drawer and chose a pair of clean cotton panties with a bow – cute but still sexy. I threw over some skinny black jeans and a t-shirt (which I tied into a crop-top) and I was ready. I checked the clock and it was 7:20 pm. I decided to set off.
The walk to my destination wasn’t too bad. I didn’t encounter anyone and I’m certain no one recognized me in my slight makeup. My plug was noticeably teasing my prostate, and my clitty was leaking a little into my pants with every step. I ran through every scenario in my head, worrying, wondering, hoping until eventually, I found myself at the door of my destination.
It was a fairly standard suburban home, nothing out of the ordinary. It had a security video doorbell at the front door. I checked the time: 19:58. I rang the doorbell and the voice of a woman buzzed through.
“You’re early. Come inside and take off those clothes, Kai.”
She clicked off. I stood there, harder than I’d ever been at hearing my own name. This was real.
I pushed open the door and stepped inside, into a luxurious mahogany-panelled interior. A chandelier hung from the ceiling in the hallway and there were stairs directly in front of me. Closing the door, I snapped out of my daze and began undressing. I hadn’t even bothered looking up, I just had an urge to obey the orders given to me. I folded my clothing and placed them on a table to my left. It held only a vase. As I stood there, naked in a stranger’s house, butt plugged and hard, it dawned on me just how strange this scenario was. I began to doubt myself and made for my clothes, only to be stopped by her voice.
“Leaving so soon? I guess you want to be exposed then.”
My jaw dropped. Down the stairs walked who I assumed was Mistress Sarina. She was gorgeous. Her blonde hair curled and caressed her body as she moved, and she was wrapped in a tight black latex corset and thigh-high boots, with matching latex panties. She held a glass of wine in one hand and gestured to me with the other. “Stay. Good boy.”
My clit leaked another drop of precum at that.
“Follow me, Kai. I have a deal to strike with you.” She floated effortlessly into a room to my right, so I followed after her. “On your knees you idiot slave.” She called through as she heard my footsteps. Getting on my knees I crawled into the room, and thankfully it was carpeted. She sat on a red velvet chair and sipped at her wine as I entered, kneeling in front of her and waiting. Soon after, though, a large and very well-built man entered.
He was naked, save for a leather pouch around his genitals and a latex mask covering his face. He walked in behind me and stood attentively at my rear. “Don’t mind Cale, he’s my number one. Always good to have protection.” She looked him up and down and giggled as she took another sip. “It’s just a bonus if they’re eye candy too.”
I shifted slightly, and she placed the glass down and leaned forward, face to face with me. Her smell was alluring, a mixture of roses and lust and I couldn’t help but take a deep breath of her in. She sat back and smiled.
“So, Kai. This must be a shock to you.” She gestured around. “I mean, I’m very glad you came. I’ve watched you for a while.”
“I.. I…” I began to stutter but she hushed me.
“No. No talking.” She licked her painted violet lips and smiled again. “I have an offer for you. I must admit I am very sorry for blackmailing you to be here, I just fell very deeply in love with you and I needed a way to meet you, even if it wasn’t your choice.” I stared at her, a mixture of lust, anger, and confusion on my face.
“You see, those videos of you I recorded without your consent, I have them here.” She reached for a solid metal box on the table next to her and waved it in front of my face. “The only copies of your escapades.” She licked her lips and bit her tongue. “I enjoyed these, almost as much as you did.” She giggled.
As she teased, my mind ran back to those nights. Fucking myself to sleep and feeding on my cum. I realized my little cock had stood to attention this entire time.
“I offer you these videos. This hard drive of you, and you can leave. You will never hear from me again.” She stood up, dominating the space in front of me. I whimpered. “If you take this hard drive, I will leave you alone forever. You will not be owned or cared for by me or my associates. However…” She placed the hard drive down, next to her now empty wine glass on the table. “Should you wish to be owned I will keep this.” She tapped on the hard drive with her long nails. “And you will be mine.” She laughed, causing me to leak another drop of precum and squirm in place.
Did she really want to own me? Kai, the sissy. The crossdressing bedroom-whore? My mind ran, and I began to speak but she cut me off quickly.
“You don’t use words here. Should you decide to be my slave, your limits and interests will be respected. I take no pleasure in forcing someone to do something.” Both of our eyes flicked over to the hard drive. “If you choose to leave then take the videos and go, dress yourself and never come back. But if you want to stay…” She picked up the empty wine glass and handed it to me. “Fill this halfway with cum. Good luck.” With that, and a purse of her lips she left the room and closed the door.
I looked at the glass, and back to the hard drive. Could I be her slave? She was gorgeous – way out of my league and more stunning than anything I’d seen online. Did I want to be her slave? My tiny erection answered that for me. I stared at the glass for a while, deliberating. After a while, and a finally soft cock, I had decided. I’d do it. I had nothing left to lose and I’d dreamed about being owned for years.
As I looked at the glass and back to my excuse for a cock, there was no way I could fill it halfway. I grabbed my cock in my right hand and began to stroke, making it pathetically hard. As I stroked I realized I had forgotten. Cale was still in the room.
I whimpered a bit as I turned, to see the hooded muscle man stood still. His eyes looked at me, drinking me in. I could see something stirring in his leather pouch. I brought the glass up to my face and it dawned on me. It wasn’t my cum that was needed, it was his. I scooted myself over to him, careful to stay on my knees and tentatively grabbed at his pouch.
His cock was thick. Much bigger than my excuse for a dick. I could feel it’s warmth emanating from outside of its leather entrapment. His defined muscles glistened slightly as I pressed a hand on his lower abs, tracing them gently with my fingers. Snatching my hand back I reeled.
I’d never been with a man. I couldn’t, could I?
Staring up at him, I could see his dark brown eyes looking straight forward now. If this was a test, I must be on the right track.
Taking a deep breath I yanked down his leather pouch and his magnificent cock sprouted free, semi-hard. It too glistened, much like his body. It was almost as big too. Thick, veiny and it looked delicious to a fledgeling sissy to me. Delicious and scary. I grasped it in one hand and quickly realized I might need two, but how could I hold the glass?
Then it hit me: my mouth.
I could use that to help, and I’m sure it would feel better than a struggled handjob. I began stroking, my hand gliding up and down his hardening shaft. His veins pulsed under my hand as his cock grew larger and larger. Eventually, the tip of his cock was in front of my lips. He was hard and it was much bigger than I anticipated.
Here goes, I thought to myself.
Holding the wine glass underneath me, I opened up my mouth and flicked my tongue over his cock head. His precum was salty but incredible. It was already thicker than my full cum loads and I couldn’t help but suckle and tongue his cock head while I stroked him.
I honestly can’t remember how long I sucked on the tip of this strange man’s cock. I couldn’t tell you how much precum I leaked into the puddle on the floor. But what I can tell you: is that I loved it. Tasting his cock and worshipping him, making him hard and working at the foot of a real man opened something inside of me – this was better than I’d ever imagined.
Suddenly he grunted. A warning. I quickly moved the tip of his cock into the wine glass and continued stroking. He grunted again and began to orgasm. Thick ropes of warm, salty cum began filling the glass as he buckled slightly and began breathing deeply. After the last spurts left his cock, I circled my tongue over the tip to clean him up and pulled up his leather pouch.
He recovered and then left the room. I sat there, having just made a man orgasm, in a small puddle of my precum. Looking at the glass, I realized it was just short of halfway. My own cock then stirred to attention, glistening with precum and ready to be stroked. It didn’t take long, I massaged my plug into me as I stroked over the wine glass that was on the floor. Three pumps of my hand had me squirting my pathetic load into the pool of ambrosia Cale had left there. Phew. The glass was half full.
As I recovered, catching my breath and trying to take in my surroundings, the door opened and Mistress Sarina walked in.
“Good girl.” She said, sneering at me as I was on the floor. “I think you and I both know what you need to do now.” She gestured to the glass, and without any hesitation, I drank it all.
“Good. You did well, I’m impressed.” She moved over to the hard drive and picked it up. “I think we’re going to have a lot of fun together, Kai.”
To be continued…
