Blackmailed by Mr. B

ATTN: All characters are purely fictional. All characters are over the age of eighteen. This story contains elements of reluctance and non-consent.

A collar that said slut, hair tied in pigtails, nipple clamps, thigh high fishnets, a short pink skirt that didn't cover my ass. On my knees in front of a man three times my age ready to suck his cock to completion. That was our agreement anyway. Until he pulled out the blindfold, twirling it around his finger. I'm not an idiot, but I did feel comfortable with him, I might not try bondage but a blindfold? Sure.

This was a one time thing. Okay maybe not a one time thing as it was our second meeting but it wasn't something I planned on making a habit out of. I was straight, afterall, this was just something I needed to experience and get off my mind. I had already reasoned to myself that curiosities are okay to satisfy, especially while you're young. I was 18, and prom was just around the corner and although I didn't have a date yet, I was planning on asking my friend Sonya that lived only a few houses down. We had become close over the past couple years and I thought prom would be the perfect opportunity to grow our friendship into something else.

In the meantime, I wanted to satiate my curiosity for the same sex and as such I turned to an older man I had met on Grindr that seemed safe. I had some reservations about his age initially, but after some consideration I decided that it was a good thing. I imagined he'd be safer, and his experience would make it easier for me. Of course, this was a significant misjudgment.

The first meeting had went by easily enough, although I learned fast my skills were lacking. He still had fun and helped me along but I resolved to do my own research and return with more enthusiasm and proficiency. In our fated second meeting he had an added request. He talked me into wearing the outfit and although at first it felt silly, I agreed to it. To be honest I think it helped me get into character so to speak and seeing myself in the mirror had me feeling pretty confident, at least until the blindfold went on. I gave it my all nonetheless and imagined I must have looked like a porno actress moaning, spitting, and sucking him down.

When it was all said and done he was pulling the blindfold off to cum on my face and I had my eyes closed, smiling, moving my tongue around like a slut. Catching the of strand that landed over my mouth and licking my lips. Leaning in to give his cock a last quick suck I opened my eyes and saw that his phone was out and he was capturing a video.

"Wait a second man, that's not cool", I said leaning back again.

"It's okay boy, just for personal use, no one will see it." He reassured me.

I didn't like it but I let it go and left soon after reasoning that he did seem trustworthy. Besides, I wasn't planning on doing this again and I figured it was only right he get a souvenir to remember me.

As the next week drew to a close I realized I hadn't deleted the app yet. Curiosity got the better of me and I logged in one more time. He had messaged me a couple times trying to make plans. I felt I owed it to him to be straight forward and give him closure so I let him know I was just satiating my curiosity and wasn't interested in another meeting. He responded quickly by sending a dick pic and asking me if I would miss it. I responded in the affirmative but once again reassured him I wasn't interested. We went back and forth for a while and eventually I agreed to meet him one last time.

When I arrived he had me wear the same outfit as the previous visit however as I began to kneel down he stopped me. He said this time he wanted to try something new. He handed me a clear latex object that after a moment I recognized as a butt plug. I giggled at this and shook my head immediately, insisting it wasn't my thing however he walked around behind me giving me a slap on my ass and squeezing it and spoke in my ear.

"You almost ghosted me, you owe me. Are you afraid you'll like it?"

Believe it or not I didn't need much more convincing than the slap. Sex was one hundred percent off the table as I knew I wasn't gay but that didn't stop me from being curious about what something would feel like in there. I looked him in the eye as I took the plug from him and he handed me a small bottle of lubricant.

"This is it though. This is as far as I go, and once you come we are finished."

He held his hands up and responded convincingly.

"Absolutely."

After 15 minutes of uncomfortable stretching and trial and error the plug was snugly inside and the mix of slight pain from the stretching and pleasure from my prostate was undeniably intoxicating. He said he wanted to watch porn while I sucked him so I shrugged and complied sitting under his desk as he watched a video. I focused on my technique more than the previous week, trying to really give him something to miss. I was a little hurt that he had me go through all this trouble looking nice just to be watching porn and have me hidden away under his desk. I hear slurping and sucking and quiet moaning and assumed it was a blowjob video. Fitting. He tapped my head and I looked up, cock still in my mouth.

"Why don't you try riding me?" he proposed.

Although I was wearing the plug and it felt great, I didn't really want to take that leap. I always considered anal as a point of no return whereas with sucking I retained a shred of masculinity. Besides, I was a virgin and I intended on losing it to a girl like any other red blooded male. I shook my head softly and continued sucking him, hoping he wouldn't try again and make things awkward.

"Why don't you come sit on my lap for a second. No funny business, this is the best part of the video." he suggested.

I rolled my eyes and stood up, thinking to myself this was definitely my last visit with this guy. I was starting to get a bad vibe and fully expected him to try for sex now. I sat on his lap carefully to avoid his cock but he shifted and sandwiched it between my cheeks. The plug protected my hole well so I felt pretty secure about it. I finally looked at the screen and saw a pornhub window and the video was indeed a blowjob scene. A cock was pulling out of a mouth, a blindfold coming off, a feminine young man smiling and catching cum. I recognized the face immediately as my own. Without warning my nipples were pulled quickly and forcefully.

"I'm sure your co-workers will like this video too hmmm?" he asked and let them go.

Fuck. He knew where I worked too. He had come in to the cafe by chance after we met for the first time and recognized me. He played it cool thankfully and that's part of the reason I trusted him enough to meet another two times. Third time's the charm I guess because he showed his true colours. I pushed off his lap for a closer look at the frozen frame of the video trying to see if there was anyway I could be unrecognizable to anyone would know me. As I leaned forward I felt a tug at my plug, gentle at first and then with sudden force, popping it out. A drawer opened and I heard the ripping of plastic and his voice behind me,

"Don't worry I'll wear a condom."

His hands grabbed my hips and I felt a blunt, slightly wet fleshy object push against my hole. I didn't resist. He pushed into me with a slow deliberate motion until he was all the way in. I had mixed emotions about it to be honest. Part of me was angry, part scared of the implication, part turned on by not having a choice. It was painful but the discomfort was drown out by all the feelings it created inside me. I closed my eyes and began having an inner dialogue with myself while he began using me as a flesh light.

*He's wearing a condom, so it's no big deal. I'll just never come back again. But he has the video, he could blackmail me. Wait, is this on video to? Oh my god his cock is huge. I'm being fucked right now. I'm really being fucked.*

I was absentmindedly moaning and making wincing sounds and it was around that point that something was pushed in my mouth roughly and I began sucking it. There was an element of pleasure to the whole experience and my cock had gotten hard which troubled me greatly. He picked up his pace and I felt his cock twitch and swell a few times before he groaned and warmth flooded my asshole. He pulled out slowly and slapped my ass hard.

"Get the fuck out", he said as I was still ass up leaning on his desk.

My eyes opened and I pushed myself up, a little shaky on my feet. I finally realized the impromptu gag was in fact the plug I had been wearing previously and gagged a little. He chuckled at this and commented on my erection making me blush. I noticed an open condom wrapper and an unused condom beside it on the desk and my heart sank. When I looked at him he grinned and shrugged.

"How's it feel to be a cum dump?"

I said nothing and began to undress but he stopped me.

"No. Put on your clothes over the girly ones."

I was about to protest but didn't have anything in me except his cum so I dressed quickly and ran out of there. I ran home quickly and when I got in, my parents were setting the table for dinner. I had begun to feel his cum dripping out of me and down my leg on the walk and now was faced with a predicament. I ran to the bathroom and wiped it up quickly but it was apparent that there was much more inside me so in a moment of panic I grabbed the plug and pushed it back inside me. I was disgusted in myself.

After a sufficiently awkward dinner, albeit one-sidedly so, I spent almost an hour in the bathroom ejecting the semen and showering thoroughly. Against my better judgement I checked the chat I had with the man and he had sent a message.

*See you soon cumdump* it read.