Quickie: Coworker

"I wanted to give you something I know you've never had or will never have in your current situation," she said, opening her eyes.

"Umm, you already have," I said back.

"That may be, but something more... something really special."

"I can't think of anything better than what we've done and are doing," I said, sliding my cock in deep for emphasis.

"Oh... there is something and since you can't think of it, makes it all the more special and something you'll never get otherwise."

"Consider me intrigued," I said.

"I want you to take my ass... I want you to have anal sex with me."

My mouth literally dropped open. Never in a million years would I ever consider this with my wife and so it had never been even a thought on my brain... until now... with Jessica.

"I can see by your expression you've never even contemplated it."

"No... never," I said.

"Is it something you would want to do?" she asked.

I hesitated... I'd heard of anal sex. Actually seen an image or two and maybe once or twice in a porno when I was younger but like I said... it was never an option so I forgot about it entirely. The idea intrigued me though and I knew I'd never have another chance.

"It is... I just never thought it would ever happen."

"It can... it will if you want," she said.

"You'll have to teach me... I don't want to hurt you," I said.

"I will and it's good you brought that up. It's different than normal sex... you have to go really slow a first and let me adjust to you. Maybe you want to use your finger first... see what I mean."

I pulled out of her, my cock was rock hard and covered in her juices again. This idea she had, made me excited, made my heart race in my chest. I stuck my middle finger into her sex, getting it wet from her orgasmic juices and then lowered it to her puckered hole.

"Now, just go really slow... it will be tight," she said.

I could feel it, what she meant... as my middle finger started to press on her tight opening. The ring finally parted slightly and it went in but then her ass clenched, pushing me out.

"Sorry that was involuntary... you kind of have to push through the first time... I'll try not to do that again," she said.

I pressed in again and this time she opened up and my finger slid into her very tight and hot anus and I felt something I'd never felt before. Her tight ring of muscles just hugged my finger snug and my heart leaped in my chest thinking about what it would feel like on my cock. I inched more into her until the rest of my hand hit her butt and I was knuckles deep inside her anus.

"Mmm, that's nice... feel how tight?" she asked.

"Oh yeah... crazy... you sure I would fit?" I asked.

"You will... it expands but it takes time and patience," she said.

I pulled my digit out and moved it back in. This was when she started playing with her own clit as I finger fucked her ass.

"Playing with my clit really adds to the sensation," she said.

I could feel her loosening up the more I moved in and out... it was still really tight, though and I was skeptical my cock would fit.

"Add another finger," she said... "Slowly."

I did as she asked, pulling my middle finger out almost all the way and adding the index finger next to it, I pressed slowly in. Wow, it was tight on both fingers and she sped up playing with her clit. I paused for a second and then eased more into her tight ass. My heart was pounding. I had never done anything like this before and I couldn't believe the reaction my body was going through. My cock was just throbbing and oozing all down the underside of my shaft and that's when I got the idea to use that pre-cum, knowing how slick it is.

With my other hand, I wiped my cock clean and added it to my finger in her ass as I pulled them out and spread it around her tight ring as well. It really helped, they slid in the second time much easier.

"You're learning already," she said, watching me.

"Lube's important," I said.

"With anal especially," she returned.

I started moving both fingers in and out, feeling the tension ease as her ass adjusted to the width. She kept playing with her clit and her nipples were rock hard from excitement. I think she really like anal and was doing it for herself as well as for me. The effect it had on my body with just my fingers was crazy... I couldn't even imagine what my heart would do when it was my cocks turn. I was content to just kneel beneath her and fuck her ass with my fingers, having the time of my life. She had other plans.

"I think I'm ready," she said.

I knew what she meant and my hand froze mid thrust.

"Okay, you sure?" I asked, knowing my cock was much wider than two fingers.

"Yes, I'll be fine... just go slow."

I got closer to her before removing my fingers and smeared my new pre-cum around my cock head before taking my fingers out of her ass. When I did, her little hole stayed partially opened and I hesitated, enamored by the visual.

"Now... before it closes," she said.

Moving at her words, I began to press my shiny, rock hard head against her hot hole. I was shaking I was so excited and my heart was pounding so much I could scarcely hear it was so loud in my ears. I watched with wide eyes as my head slipped into her tight hole as slow as I could go. I paused, feeling the intense heat and grip her ass had on my shaft. She sped up on her clit and I waited for her 'okay to proceed look'. I was awestruck at the sensation on my cock and the excitement it produced.

"Mmm... wow... you are big... really... wide... actually," she said, panting a little.

I didn't move, letting her adjust and play. It took some time, maybe a couple of minutes before I felt her muscles relax slightly on my cock. I thought she might change her mind and tell me to take it out and go back to normal sex but she didn't. She adjusted and gave me the signal to continue.

That's when I really started freaking out... when I pressed further into her and felt her incredible hot and tight anus grab my shaft as each inch passed further into her. It is indescribable how good it felt and how I reacted. I'd never been that excited and worked up ever in my life before or after. I stared down at my cock, watching it disappear into her tight ass. Her skin around her anus was so stressed it turned white as my cock inched in. I stopped halfway, basking in a sensation I'll never forget. She was playing ferociously with her sex and had her eyes closed when I briefly looked up.

"Oh... oh... wow... oh... it's... its so big... Rob... so big..."

Instead of moving more in, I pulled about two inches back out and felt a new kind of sensation, as her ass clung the opposite direction on my cock, not letting me out. It was so different than normal sex, almost like she had much more control and ability to affect my cock. I moved back in the same amount I had taken out and added another inch along with it. I could feel her loosening again and I was amazed at how she adapted to the size. I felt myself sliding in easier and then when I couldn't go further I backed out, loving the withdrawal sensation of her ass grabbing and pulsing around my retreating cock.

With just the head in, I paused, stunned by the visual of my cock extending out of her ass and looking like it had been snipped off at the head she was so tight. She opened her eyes and looked at me.

"It's totally worth it isn't it?" she asked.

"Oh my hell, yes... I've never... never felt anything like this before."

"You're welcome... I told you it was special."

I only nodded and eased my cock back into her incredible ass all the way again. She had adjusted fully now... it was still tight but I knew I wasn't going to hurt her if I moved faster. She knew it too and told me so.

"I'm good now... fuck me and cum in my ass."

Word's I never ever thought I'd hear before sounded in my ears and my cock lurched in her ass as the excitement grew. I hadn't noticed until now, but my balls were already tight against my shaft and ready to burst at any time. Pulling out, I slid in and out... over and over, blown away at both the sensations and the stunning visual treat of my wide cock extending out and disappearing under her open, wet sex with her hand circling her clit rapidly. She was in to it as well, I could tell by her nipples and the amount of juices I could see in her open sex.

"Can you last a few more minutes...? I want you to cum with me," she asked.

"I don't know... it's so good," I said.

"Try... I'm close," she said.

It was going to be exceptionally difficult to not cum with how excited I was and what I was doing. I tried my best and knew if I let my mind wander it would help.

**

"Another week without sex?" she asked.

"Well... if you must know, yes," I said.

We had become really good friends by this conversation... two years after she started working with me. We talked about pretty much everything and one of the subjects that she would always bring up was my lacking wife. It drove her crazy.

"I'm furious... how can she do that to you...? how can she resist... I mean you're hot, Rob... she must see that and still she doesn't want you?"

"Apparently not," I said, ignoring the hot comment.

"Well, I'm at the point where something needs to be done. I'm going to talk to her."

"The hell you are?" I said.

"She's being so cruel, something has to be done."

"Talking to her would only make it worse, then she'd know I've told you a bunch of stuff I shouldn't have," I said.

"True, but maybe she needs to know."

"No... she doesn't."

"Well, then, I have another idea..."

**

I'm sure you can guess what her other idea was and you know what happened from there. It ended with my cock in her ass and the single most stunning sexual experience of my life.

The mind wandering helped. I hadn't blown my load yet but it was taking everything I had not to. She was working on her own orgasm, vigorously playing with her clit as I kept thrusting my cock into the first and only ass I'd ever fucked. I don't know how I held out... my balls were so tight and the sensation already cresting. There was no stopping my orgasm now... all I could do was try and hold it until my muscles gave way to the involuntary contractions. Somehow, I managed to hold out long enough for her to climax too.

"I'm... I'm... cumming!" she screamed.

My cock let loose inside her tight ass, which was now spasming on my cock as her orgasm took over. The effect multiplied my pleasure as my cock began to be milked by her contracting muscles, during my ejaculation. We both moaned, grunted and shook as we finished together. I swear it felt like I emptied a gallon of semen deep inside her bowels. My cock just kept contracting and shooting as her ass pulsed around it. I've never felt anything like it before or since.

When we finished she got up and went into the bathroom of the hotel. When she came out, she was already dressed.

"Well, my plane leaves in less than two hours... I've got to get to the airport," she said, walking to the edge of the bed.

She leaned down and kissed my forehead before saying, "I hope you'll remember me and this time we spent."

"I totally will and I'm happy for you and your new promotion... just wish you didn't have to change divisions," I said.

"Can't move up if I'm not willing to move," she said.

"I know that. Still I'm going to miss you."

"I'll miss you too, but I hope what we did was worth it... now you know what you're missing."

"Pretty sure I already did."

She smiled, grabbed her bags and left me in the hotel room. As the door closed my mind drifted back four hours earlier.

**

I was working in my office at the end of the day around 4:30. Jessica came in and sat down in the chair across from my desk.

"So... it's my last day," she said. "I'm heading out."

"Yeah, I know... crazy... I can't believe you're moving and leaving me here."

"I've got to do what's best for me and my future," she said.

"I know... it just sucks... you make coming to work fun and something I want to do," I said.

"That's because I'm so cool and we make fun of everyone else."

"True... so don't leave."

"Rob... I've got too, I've already accept the position... but there is something I want to do and you'll have to decide for yourself if you want to do it too," she said, standing up and handing me a folded piece of paper before walking out.

I opened it and read: Hilton downtown in an hour... ask for messages for John Smith at the front desk.

My heart jumped in my chest.

**

I never told anyone about that evening at the Hilton, I'll take it to my grave but just because I've never told anyone doesn't mean I could ever forget.

The end.