Joe and the City Ch. 01

Here I was at the door of a friend of a cousin, and I had no choice but to take the plunge. I rang the doorbell, with a sense of foreboding. See, I was visiting the city, and my cousin says, "hey you should stay with me friend Kelly."

Having never seen Kelly, my mind conjured up a series of images. June Cleaver in black and white, or Elvira Mistress of the Dark were just a sample of what I had in mind. But primarily was an aging woman, living on her own in the city, eating TV dinners on a tray in front of Fox News and Wheel of Fortune.

"You must be Joe," she said as the door to her apartment opened. We were on th3e 23rd floor of a posh building, and I had a hard time reconciling my prior thoughts with the woman standing in front of me now.

She was - how do I say it? Hot. Very fucking HOT! Long blonde hair, gorgeous eyes, tight body with tits which stretched the limits of my racing imagination, all in a cropped loose sweatshirt and tight yoga pants. Damn.

"Uh, yeah. I'm Alex's friend and I just wanted to drop by and say hi," I stammered. "I'm not able to stay, thanks for the invite but I have a room downtown..."

"Nonsense," she said as she took my arm and pulled me into her apartment. "Alex said you'd try to weasel your way out of it, but I can tell you - you are staying here!"

Her eyes were mesmerizing. She was probably ten years older than me, but she had a confidence about her that was irresistible. Truth be told, I was planning to spend the night on a table I had seen near her building. To put it mildly, I was broke. Thus the trip to the city to try to find a good job.

Yet, I was overwhelmed with her sophistication and grace, not to mention that she was HOT! So I had chickened out and made that lame excuse of another place to stay - of course it was a big fat lie, and she just thrust it aside as she drew me into her living room.

The large windows gave a stunning view of downtown, but I could not pull my gaze away from her as she sat me down on the couch. "I'll bet you are a scotch man, right?" she asked.

"Um, sure," I stammered. I never had the pleasure of scotch, but what the hell?

"Glenlevett coming right up," she said as she literally bounced up to go to the kitchen.

What the hell was I doing? This gorgeous blonde would kick me to the curb in a second if she knew how broke and destitute I really was. I felt a fraud.

"So Joe," she called as she was preparing the drinks, "how do you like our city?"

"It's great," I said. "The Uber driver gave me a list of places to go for fun."

"Oh, no you don't," she said as she approached me with two tumblers of amber liquid. "Mu cousin's friend isn't taking cues from an Uber driver!" She laughed as she clinked her glass to mine. "Here is to the beginning of a beautiful friendship!"

I sipped the scotch (so good) and we continued to visit on the couch. She was a PR professional and worked from home for now (during the pandemic). She said flat out that she had a lot of contacts, and could get me an interview with some good firms.

"But, Joe..." she started looking hard at me. "I need you to be honest with me."

Gulping, I took another drink then unloaded my story on her. I had been laid off at the print shop six months ago when things slowed down, and now I was desperate for a job.

"Um, I see," she said looking at me clinically. "Tell me, what do you plan to wear to these interviews?"

I gestured to my bag by the door. "Just my nice shirt, tie, and my dad's suit coat."

"Hmmm. Let me see them on you," she said bouncing up and grabbing my lone, worn out bag. She ruffled around and procured the items I had mentioned. I was embarrassed to let her dig through my stuff, but I was so enthralled by her I did not say anything.

"Oh, honey," she said looking at my clothes. "This will never work. Not for a guy as attractive as you are. You need to show off a little. Not too much, you understand, but enough to make the girls on the floor perk up and take notice. Perhaps wet their panties just a little," she said with a giggle.

At that point I felt the first twitch of the evening from my cock. It would not be the last.

"Come with me," she said pulling me up. She took me into a bedroom and opened a giant closet. It was filled with mens clothes. "These are from my clients, who send me samples to promote their clothing lines. I take photos and post them on social media, and voila, they increase sales."

I was intimidated to say the least, but Kelly never slowed for a second. She began to hand me various shirts, holding them up to me and looking at me with that clinical gaze. "Um, not that one... let's see... here. Try this one on."

Taking a beat to gather my courage, I slowly took off my tee shirt, and began to put on the button down shirt she recommended.

"Oh Joe, you are much too modest for this town," she said with a giggle. "The girls on the floor will just eat you up if you are not very careful." Saying this she rubbed her hand across my chest smoothing out the shirt. She lingered just a second or two on my pecs as she did this, looking into my eyes.

"Now for the trousers," she said. She selected a nice pair of pants, and my mind continued to race.

What the hell was going on here? Was she just helping out a cousin's friend? Or did she really like me? I was too confused to give direction to my cock, which continued to grow into a semi hardon.

"Put these on," she said, handing me the pants.

I stood for a moment as she looked at me expectantly, and then I gathered my courage and began to unbutton my jeans. She looked directly at my crotch as I unzipped, and never gave the slightest idea of what she was thinking. I pulled down my pants in a swift move, hoping to get the new trousers on quickly.

"Stop," she said quietly as my pants were around my ankles. "Please tell me that you are not planning to wear those?" She gestured at my tighty whities in disbelief. "That will not do at all," she said heading to a drawer.

She pulled out a series of mens underwear. From tight g-strings, to bikinis, to silky boxers, she had everything.

"Perfect," she said as she pulled out a pair of skimpy bikini briefs. "Put these on first."

Damn. I thought to myself what the hell? And then I proceeded to pull down my shorts to reveal my semi hard cock.

"Stop," she again commended. I was halfway down with my underwear and as fully exposed as possible, with my jeans still around my ankles, and now my underwear around my knees.

"Joe, I know you have razors in your state. So what the hell is that?" she pointed at my pubic hair which I admit I had never has the courage to trim.

"Um, I guess I didn't want they guys to laugh at me," I said - frozen in place.

"No, that's not good," she said. Never let others define yourself for you. I could tell you were more sophisticated than that when you came in. Now you just have to believe in yourself!"

She quickly grabbed by arm again, and I barely had time to kick off my shorts and jeans as she lead me to the bathroom.

"Come out when you are finished," she said slapping a razor and shaving cream into my hands.

(*)(*)

About twenty minutes later I came out in a towel. My dick was throbbing but I managed to conceal it with the fold of the towel. To be fair, I had never had so much excitement in the shower, shaving off all my pubes and stroking my cock. But I kept it under control and did not cum.

"Did you cum?" she asked as she looked down at my body.

"No," I said in a tone that suggested indignance, but probably came out as wimpy.

"Good," she said looking into my eyes. "That is for later."

What the hell? My mind was racing so much that I barely noticed as she pulled off my towel, leaving me buck-naked in the room. "Oh, that is much better," she purred as she looked at my penis.

Kelly then knelt down in front of me and my cock sprang up at the thought. But she already had the blue bikini shorts in hand and helped me step into them. She pulled them up, and gently slid my semi-hard cock down into the briefs.

Then she stood up, dangerously close to me, and slowly slid her hand up and down my shaft as she adjusted the briefs on me. The whole time she kept eye contact with me.

That is much better she whispered. I think you are ready.

Ready? For what? My mind conjoured up images of various sex scenes as she turned away from me.

But, to my disappointment, she handed me the clothing she had prepared for me.

I dressed in front of her. She made tiny adjustment along the way, tucking here, pulling there and running her hands through my hair. Damn, this woman was driving me crazy with lust for her.

"There," she announced, "you are now dressed to kill in your interviews."

I didn't know what to say as I looked in the mirror. She was right. I was professional. Not too overdressed like a bumpkin, but not a slob. Just right.

She gestured to the bed, and told me to make myself at home.

Of course, this was the last thing I had expected from the evening! Her hands on my dick were still running through my mind, and I kept imaging the sight of her as she knelt in front of my half-hard cock.

"Oh, okay," I stammered in confusion. What happened to "later"?

"Oh, Joe," she purred pulling up close to me. "I have some important calls to make, and you need your rest. I will see you tomorrow. Promise."

Then she kissed me. Just a light kiss on the lips with just enough pressure to let me know that she was interested.

"Goodnight," she said pulling away and closing the door behind her.

(*)(*)

Of course I was jerking my meat just minutes after she left. I was careful to fold the clothes for tomorrow, and then I jumped into the bed with my hard-on cock raging.

I was frustrated, and had a bad case of blue-balls as I stroked, but I did not want to hurry myself. I mean, if I had all night why hurry, right?

So I stroked to the edge, then allowed my dick to relax - only to do it all again. This went on for some time. I was hearing Kelly moaning in my mind as my hand slid up and down my cock shaft. I could swear I heard her giggle in delight as I teased the tip of my penis. It was thrilling!

Then I stopped, in control and on the edge of cumming. But I could still hear Kelly's moans coming from the other bedroom.

I froze.

Wait a minute, was I hearing those sounds or was I imagining it?

What the fuck?

Frozen in the moment, I kept my hand off my rock hard dick and focused on listening in the still apartment. There. It was a moan coming from somewhere in the apartment I was certain. But, what if I was wrong? What if the sounds came from a neighbor?

I felt foolish, but I simply had to investigate. I conjured up a plausible story about needing a glass of water and then I slipped on the blue bikini briefs. They still felt amazing on my hard cock and I realised just how much I had missed out on during my sheltered life. No more, I decided. I was going to see what the real world held in store for the new, confident man I was becoming. But I had no idea...

(*)(*)

Into the kitchen I walked, wearing my tiny bikini. I thought "what if I am wrong and she finds me here in her kitchen?" That thought deflated me to about ¾ of a hard-on, so I reached down and tucked my cock into the pouch in the silky briefs.

I poured a glass of water, and saw the bottle of scotch on the counter. I took a healthy swig for courage, and proceeded down the hall. There was a tiny shaft of light coming from the bedroom door at the end of the hall. Kelly's room.

Pausing, so I did not make a sound, I began to slowly make my way towards the sliver of a crack in the dark hallway. My heart was beating fast. I was straining my ears to see if I hear anything at all close to the moans I thought I had heard before.

"Oh, God!" came from the room. I froze.

What if she had a visitor? I was not familiar enough with Kelly to know her schedule. Perhaps her boyfriend or lover only came over late in the evening? I'd be a real jackass to walk in on a couple having sex.

But my dick twitched at the thought, and that was enough I guess. I crept toward the crack of light.

Just then Kelly let out a low moan. I was getting harder as my eye came closer to the door.

I could see just a pair of legs stretched out onto a desk, which was filled with computer monitors. What the hell?

Kelly moaned again (by now I was sure it was her), and the legs spread out just a bit. I could not make out what was happening in the room, but it was making my hard dick stretch to the limits in the tiny briefs.

"Thank you Sam," she said in a breathless voice.

I looked closely at the computer stuff on the desk. I could only see part of it, but I looked like a woman who was fingering her pussy and rubbing her tits. Porn? Was Kelly into porn so much that she had such a setup?

Disbelieving my own courage, I gently pushed on the door to get a better view. To my surprise, the door was well oiled and did not make a sound as it pulled wide open to reveal a wonderful sight before my astonished eyes.

Kelly was in a chair, her legs on the desk, and her left hand was down at her pussy massaging with a passion. Her right hand was rubbing her tits, and though the view was blocked to me I could clearly see her in one of the three computer monitors.

What the fuck? She was performing on a webcam? I had NOT seen that coming at all!

She was so natural and in control as she interacted with her friends on the cam. She was moaning and saying thank you, which I gathered was for tips they were sending. I noticed I bell sound each tip, and figured it out.

As if lead by my throbbing dick, my feet moved me forward into the room.

Kelly turned to look at me with a mixture of surprise and lust. I was hooked. Anything she asked of me I was willing to do.

She put her finger to her lips in a "shhh" sign, and I waited.

I watched as she turned back to the monitors and continued to build herself to a climax for the viewers. Damn, she was so hot. Her tight body was writing on the screen as she moaned in appreciation for each and every tip.

Then, Kelly seemed to lose control as a cascade of bells chimed and her body began to thrash in the chair. She moaned and fingered her pussy as the tips of appreciation poured in. I could see in the monitor that she had a pink device shoved deep inside her wet pussy, and I guessed (correctly) it was giving her pleasure.

I was frozen. Just watching her work was such a pleasure. My cock was straining to burst free of the bikini, and I allowed my hand to slip inside my briefs to slowly massage my swollen balls. God, this was intense.

Finally, her thrashing stopped, and Kelly blew a kiss to the screen. She moved the mouse and a "be right back" screen took over her video feed.

Now was the moment. Now I had no excuse. I was caught watching my gracious hostesses in her most intimate acts.

Kelly stood up, and wrapped herself in a silky throw that barely covered her body. Not at all self conscious she walked directly over to me and stood just a few inches away.

Then... she kissed me. Not like before, with a light touch. No, this was a I want to fuck you kiss. I was in heaven.

She continued to kiss me, her tongue running wild in my mouth. My hands reached up on their own any began to massage her fabulous tits. Her hand reached down into my briefs and grasped my throbbing dick.

We did this for about an eternity. Or two.

Or three, I lost count as my eyes glazed over and my body began to tingle.

This was, by far, the most sensuous woman I had ever been with. I felt elation at the fact of being here and now. If I died, at least I'd die fully satisfied.

"Joe," she said between kissies...

"Um?"

"Will you do something for me?"

"Mmmm, yes"

"Good," she said pulling back. "Come over here." She took my hand and led me to the chair. She then sat down and wrapped her arm around my waist, pulling me close to her side.

It is a good thing she did not tell me what was next. I'd probably freak out. Instead, with my head swimming in testosterone, she clicked the mouse and we were live on screen.

I freaked out just a little anyway.

"Oh shit," I exclaimed, "Someone I know might be watching this!"

"Relax Joe," she whispered. "It is all in fun, and what happens online stays online."

That seemed to settle my brain. But I was still freaked out to see myself standing by her side in bright blue bikini briefs and with my face fully visible on camera.

"He is a bit shy everyone," she said into the camera. I thought that to be the understatement of the year. I was petrified.

"Joe, say hi to the world," she said as her hand slid up to lightly rub my balls.

"Um, hello," I stammered.

"Such a nice, shy boy," she purred as she rubbed her had up my throbbing penis. "What should I do with him?"

The bells began to chime and she squirmed in delight as suggestions poured across the screen.

"You want me to pull down his shorts?" she whispered as her hand tugged at the top of my briefs. "That is an excellent idea!"

Then Kelly pulled on my bikini and out sprang my raging cock. I was watching it on screen, while feeling it happen below. I was beyond enthralled at this point. I was in total ecstasy.

"What Sam, you think should suck his dick?" She pulled me over, so my cock was directly in front of her mouth. "I may have to think about that," she said in a sexy voice. "It is such a nice cock, don't you think?" The chimes went wild.

"Perhaps just a taste," she said as her lips bruised against my tip. I felt a shock of electricity shoot through my penis at this point, and I twiched my cock visabally on screen.

It was a visceral sensation watching my penis as it drifted toward her mouth. Of course, I felt the sensation of her lips as they encircled my penis tip, but I was also out-of-body watching it on screen.

Kelly must have decided that sucking on my penis was a good idea. I certainly did not argue. She proceeded to lick, stroke, and suck my cock with a skill level I did not believe possible. With every slurp of her mouth, and every lick of her tongue I was cresting up to the edge of an enormous climax. Never in my life had I experienced such pleasure.

And the thing was, it was all being broadcast for the entire world to see. I alternated my view from looking down directly at her giving me a blowjob, to looking at the screen where I was fully on display as she devoured my cock. It was unreal.

Then, she stopped. She slipped my rock hard dick out of her mouth and turned to the camera.

"I think Joe has had enough," she said to the viewers.

I was crushed. I had this enormous hard on, clearly seen on camera, and I was desperate for release.

The bells began to chime again. "What," she asked in a mock surprise. "You want Joe to fuck me? I will need to think about that. Maybe Joe can give me some encouragement."

I needed no prompting from our viewers. Immediately, I reached down and opened her silk throw to expose those huge tits. I knelt down and took her breast into my wet mouth. She tasted exactly as I imagined, just a slight salty bit of sweat and a great deal of clean flesh. Her nipples grew hard as I alternated between her tits.

Kelly moaned in appreciation as I sucked on those luscious mounds. Her hand went to my dick and she stroked me as I sucked. I groaned in pleasure as I slid my hand down to her shaved pussy.

She gasped in pleasure as I slid a finger into her wet opening. I began to suck and finger her in a building rhythm. Forgotten was the camera, the audience, and everything else. This was what I had wanted from the moment I entered her apartment.

Suddenly, she sprang up, and swiveled her chair around. She kissed me then slid off her silky throw to the floor. Nude, she mounted the chair facing away from me and presented her shaved pusssy to me, and to the audience.