Keith

Story Info
Have you ever been attracted AND repelled by someone?
2.4k words
4.59
17.6k
22

Part 1 of the 2 part series

Updated 06/09/2023
Created 01/19/2019
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Have you ever been attracted to someone and repelled by them at the same time? I didn't think it was possible until I met Keith. He'd transferred in to our office from another city, and immediately became the alpha dog. He was in his mid 40's, loud, obnoxious, crude, rude...and oh so goddamn handsome. And built. He was a head taller than six foot, a muscular 270 pounds. He looked like he could pick up a car.

The women in the office looked at him with dreamy eyes. Unfortunately, so did I...although quietly and from a distance. I was 19, and still so deep in the closet that nobody would ever figure out that I was gay, or so I hoped. I'd been attracted to men my whole life and recently had discovered those wonderful little holes between the bathroom stalls at a run-down, decrepit mall a short distance from my apartment.

I don't know if Keith somehow picked up my attraction or he just singled me out because of my size. I was a small guy, barely 5'5" and about 100 pounds. Plus, I was the only male working in the department. From the first day he teased me mercilessly, referring to me using names like "sweet cheeks" and "hot stuff" as he did with the women in the office. At some point, he started calling me "Mary" instead of "Martin". At first, I bristled and was going to report him to management but word spread that he was a close, personal friend of the owner and complaints wouldn't go anywhere...except maybe to the unemployment line for the person that complained.

So I tolerated his abuse, all the while secretly lusting after him. I sated my hunger for his cock by nightly trips to the mall. I imagined that every cock I sucked was his and was both thrilled and disgusted with myself about it.

This lasted for about four months until the mall finally closed down. It had been a long time coming, and when it finally did close there was only a few stores left open in it. My wonderful place to find relief was gone, and I had no place else to go.

I slowly went crazy for the next few weeks. I wanted COCK. I wanted to hear men grunt as they ejaculated into my waiting mouth. I wanted big gobs of cum sliding down my throat

I stayed late at work one Friday. I'd spent too much time daydreaming about men and what I wanted them to do to me, and had gotten behind on several tasks. Also, I didn't really want to go home. Here at work, at least, there were things that would take my mind off of cocks when I wasn't daydreaming about them.

I was just finishing up when someone spoke behind me.

"Why are you still here, sweet-cheeks?" Keith's voice rumbled. "Everyone else left an hour ago."

i jumped at the unexpected sound, then turned around. "I was supposed to have these forms finished today," I explained.

"Very conscientious of you, Mary," he said. His pet name for me rolled easily off his lips, and a shiver ran down my spine. He set a soda can on my desk, then lowered himself into a chair. "So, Mary, tell me about yourself. I know most everyone's stories here except yours. You always seem to scamper away when there's an opportunity for you and I to talk."

"Uh...like what?" I stammered.

"Oh, I don't know. Are you from here? Brothers and sisters? Life plans? How long have you worked here?" he said casually, pulling out a pack of cigarettes. He put one to his lips, then proffered the open pack to me. God, he looked so masculine right then, so manly, sitting there casually with the cigarette dangling from his mouth. Our building was supposed to be "smoke free", but he didn't seem to care. I shook my head "no", and started putting the forms on my desk into a neat pile as he lit his cigarette.

He laughed, exhaling smoke. "See? You're trying to get away right now. Sit back, and talk a while."

I wanted to run away, to flee from him despite being so damn turned on by him. I forced myself to sit back in my chair. "Well," I started nervously, "I was born and raised here, no brothers or sisters, and I hadn't really thought much beyond this job. I started here right after high school a year ago. What else would you like to know?"

He nodded, then his smile turned into a lazy grin, "That's more like it! So, when did you discover that you got turned on by guys?"

I choked. "Wha...what...I'm not..." I stammered.

"You didn't think I can see the way you look at me?" he chuckled. "You've got the biggest moon-eyes for me of anyone in this office. Hell, half the girls here pointed it out to me. They almost think of you as competition."

"I...I...I..." I stuttered. I didn't realize that I was being that obvious.

"Hell, I bet if I pulled my cock out right now, you'd gobble it down like the little faggot that you are," he said, interrupting me.

"No, I..." I stammered. I wanted to object and continue my masquerade, but I knew if he DID pull his dick out, I WOULD suck it. Hell, I'd let him do anything to me that he wanted to.

He put his cigarette out in the soda can, then stood up. "I'll prove it to you," he smiled, then unzipped his pants and fished his half-hard dick out. "Just TRY to ignore it. If you can keep your lips off my dick for two minutes, I'll believe that you're not gay."

I sat there like a deer in headlights. It was RIGHT THERE, waiting for my mouth. And I so desperately wanted it. The craving kept coming in stronger and stronger waves until I finally slid out of my chair and kneeled before him.

"That's a good girl," he said, putting his hands around my head and pulling my face closer and closer to his groin. The head of his cock touched my lips, and I opened my mouth. He slid into it easily.

"Yeah," he breathed heavily. "Be a good cocksucker and suck me dry, Mary. I've got a huge load waiting for you."

I sucked hard and starting stroking his cock with my mouth. I was scared shitless, but in heaven at the same time. I couldn't believe I was doing this, realizing my fantasy about him. At one point, I was afraid it WAS a fantasy just playing out in my mind.

My lips and tongue made love to his cock with a passion I'd never experienced before. I wanted him down my throat, wanted him to proclaim that I was the best cocksucker he'd ever met. I wanted to suck the cum from his balls, swallow his load, then suck him hard again. I was lost in lust of this man, tasting his manliness, feeling the strength of his hardon in my mouth.

He started breathing hard, and thrusting slightly into my mouth...I knew he was about to blow his load. I sucked his cock in a frenzy, oblivious to anything except the overwhelming desire to taste his eruption. Seconds later, I was rewarded. He grunted, and my mouth filled with his creamy, salty essence. I was so turned on that if I had touched my dick at that point, I would have cum in my pants.

I swallowed most of it, but some squelched out past my lips. He slowly pulled his cock out of my mouth, then tilted my head up towards him. Smiling, he said, "That's a good look for you, you know, with my cum all over your lips." Embarrassed, I stayed on my knees and looked at the floor as he stood up, put his dick back in his pants, and zipped up.

"You'll be working late again, I trust?" he asked with a smile. "Dedicated employees are rewarded around here. I plan on giving you LOTS of rewards from now on."

I nodded, but kept staring at the floor. He reached down and tilted my head back up. "Don't be like that, Mary," he said. "You're better than most women I know. Be proud of it. It's an asset that will let you go far in this company." With that said, he patted my head and ambled off. It took me a few minutes to get up off my knees and back in my chair. Kleenex took care of the cum still on my lips, and caught the huge load after I jerked off in my chair, reliving the memory of his cock in my mouth.

I must have jerked off a dozen times that weekend, remembering being on my knees in front of him.

I didn't see him until late Monday afternoon. When he ambled up to my desk, my hands trembled and my dick got hard in my pants. He walked up next to me and put his hand on my shoulder. I damn near creamed my pants.

"Do you have any panties, Mary?" he asked me quietly.

Startled, I looked around. Everyone except Suzie had already left, and her desk was far enough away from mine that she couldn't hear him. "What?" I asked.

"Panties," he said patiently. "Women's underwear."

"Uh, no," I stammered.

"Get some," he said. "The frillier, the better. And wear them tomorrow."

"I can't do that!" I exclaimed softly, glancing towards Suzie's desk. Thankfully, she was oblivious to our conversation.

"Sure you can," he grinned. "And you will." Without another word, he walked away from me. He went by Suzie's desk and talked with her for a moment, sending glances my way every so often.

Panties? Was he serious? There was no way I was going to wear panties, much less at work. I waited until after Suzie left for the day, but he never came back to my desk. When I went by his office on my way out, the lights were off and the door closed. He'd already left.

An hour later, I stepped out of the clothing store, clutching the bag that held three pair against my chest. I knew the saleslady didn't believe that they were for "my girlfriend", but she went with it long enough to make the sale. It probably helped that I picked out the most expensive ones I could find.

I had half a hard-on all the next day. The panties DID feel good, their silkiness making each movement a caress of my dick. I liked the way they felt against my ass too. But I didn't see Keith all day. At 5:00, the last of the girls left while I dawdled at my desk.

Bing. My computer announced that I had an email, and I looked at it. It was from Keith, and there was no subject line.

"My office. Now." That's all it said. My legs were weak as I stood up, and for a moment I wasn't sure I would be ABLE to stand up. Shakily, I walked over to his office. Taking a deep breath, I walked in.

"Close the door," he said, motioning with his hand. I turned around and closed it, then stood in front of his desk.

"Let me see," he smiled.

"See what?" I stammered.

"Your panties," he said.

Despite my nervousness and horniness, I got a bit indignant. "How do you know I'm wearing any?" I asked. Dammit, he was so arrogant, cocksure that I'd followed his instructions.

"Because I told you to," he said. "Now, off with the clothes."

I took a deep breath, and unbelted my pants. I dropped them down enough for him to see that, yes, I was wearing panties.

"All of it," he commanded.

"What?"

"All of your clothes...except your panties, of course," he said.

I glanced at the closed door, then pulled my shirt off. My shoes, socks, and pants became a pile on the floor.

"Turn around," he said, twirling his finger in the air.

I did a slow pirouette.

"Very nice," he said. "Grow out your hair and get some tits, and you'd be an attractive woman. You've got a hell of an ass on you, Mary."

My face turned red.

He pushed back from his desk. I could see that his pants were already open, and his hard cock was jutting obscenely in the air. My mouth watered.

"I'm going out tonight with one of the girls in the office tonight," he said. "But it's difficult to have a good time with a constant hard-on. So come over here and take the edge off."

A flash of anger shot through me. He was going out on a date with a woman, but wanted me to suck his cock beforehand. What the fuck?

In my mind, I saw myself putting my clothes back on and storming out of his office. What my body did, however, was walk over to him. His hand caressed my panty-clad ass once before slipping up to my shoulder and pushing me down to my knees.

"Good girl," he murmured as my lips found his cockhead and I drew him into my mouth deep. I gave my all sucking him, trying to take him deep before gagging and failing. I don't know whether it was my enthusiasm or that he was ready to cum, but after only a minute he exploded in my mouth. I savored his cum, not swallowing his load until I felt him start to soften and pull out of my mouth.

"A little more practice," he said, "and you'll be a championship level cocksucker, Mary. Make sure you got it all."

I licked his now-soft dick, my tongue making sure it was spotless. I kept going, hoping that he'd harden again, but he gently pulled me away from him before tucking his dick back into his pants. He grabbed my arm and urged me to my feet.

"Tomorrow, nylons," he said. His finger went up, as if a warning. "NOT pantyhose. Nylons, with garter belts to hold them up." He stood up, then walked to the office door and opened it.

"Be a dear and lock up on your way out," he said, then stepped out.

I stood there, fuming stupidly, for a minute before collecting my clothes from the floor and dressing. I blow him and on his way out the door for a date with someone else, he told me to lock up his office. The arrogance! Well, fuck him, I thought.

But I turned off the lights and locked his office on my way out.

I found the same saleslady as the night before. She was nice about it, even showing me how to put them on without making a run in them, but I knew inside she was laughing at me.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
MichaelfantasiesMichaelfantasiesover 1 year ago

This story is a scenario that always scared me. Could this really happen to me? Would some guy find out that I liked to suck cock and blackmail me? As a fantasy, this story is HOT! In real life, this is something that I fear, as I've been very discreet about my sexuality and interests. Also, being alone for some time now, a persistent, confident man would make me weak and give in.

SparkyMark1961SparkyMark1961over 5 years ago

Hope more is coming soon. I like the way this story is going.

CarrieQCarrieQover 5 years ago

Can't wait to read more!

AnonymousAnonymousover 5 years ago
LOVED IT!

Your story has everything going, dominance, sissy, crossdressing, cocksucking and humiliation. I can hardly wait for the next chapter!

Share this Story

READ MORE OF THIS SERIES

Keith Series Info

Similar Stories

Homecoming Queen A high schooler helps a friend who doesn't have a date.in Transgender & Crossdressers
Shemale Step-Sister Teen boy spies on his shemale step-sister and gets a treat.in Transgender & Crossdressers
A Taste of Step-Cock A young gurl meets her new step-father.in Transgender & Crossdressers
The Deal Freddy's wife convinces him to dress up and go clubbing.in Transgender & Crossdressers
The Feminisation Initiative A new world order of forced feminisation begins...in Transgender & Crossdressers
More Stories