Alison Ch. 01

Story Info
Older woman fully interviews her suitor.
1.4k words
4.17
32.1k
1

Part 1 of the 2 part series

Updated 09/25/2022
Created 11/11/2005
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I work as a cog in the machine for a gigantic corporation, with thousands of people working on my campus. The long hours on the job required by corporate life, the late night coffee breaks provides opportunities to get close to women around campus. This is where I met Alison.

Alison is a group leader for department similar to mine but in a different sector of the campus. She is older about 30 years old I figure. She has bedroom brown eyes with dirty blond hair, which just make you melt at first site. I of coarse was lusting for her the moment we met. She would wear these tight fitting jean skirts, which flattered her slim yet athletic figure and showed off her tan thighs. I later learned that on the weekends she surfed at the local beaches and had very distinct tan lines.

I spent time meeting up with her during coffee breaks and lunches so she could "mentor" me. We got to know each other on a professional level and started to delve into personal matters. A few lunches after that I asked he out on a date.

Alison said, "Well Billy that doesn't come as a surprise, but I have certain rules and precautions when it comes to dating people from work." I said, "whatever precautions you want to take I think it's worth it.

Most of the precautions were standard office romance crap about not letting romance interfere with work and the like, but she did say, "I have a few rules to discuss over dinner before any commitments will be made." I took that as a yes and ran with it, only later did I discover what it meant to be committed.

The date was for later that week and the time seemed to drag on and on. Finally it was date night I got a haircut, dry-cleaned my suit, and waxed the car and I thought I was ready for the date. I pulled up to her house and she must have seen my coming because she was already walking down the steps to the drive.

She was dressed in a black silk cocktail dress with massive slits up the side. It showed off the tan, her pert A-cup breasts, and what I didn't notice at work a hard body. The silk dress just seemed to flow over her body, and I couldn't be sure because of the distance but it appeared she forgot to wear her bra and panties. I let out a sigh of excitement for the evening to begin and stopped the car in the drive.

Once we were off on our way to dinner Alison said, "Bill, let's discuss a few more of the rules." I shrugged and she immediately slapped me hard in the groin. The car skidded around the turn while I tried to get it under control "First rule is open communication I want to hear you speak!" She then laugh out loud and played it off as a joke. I was both pissed and turned on at the same time.

The next rule was honesty, then something about creativity, and finally that this date was an interview, if I excited her it would continue, if I played it cool and reserved tonight was the only night I'd see her out of work. It was a challenge and interviews are what us corporate types are all about, so I was excited to see where this night was headed.

We were seated at the dinner table in one of those trendy bistros with about six other tables in the place. The orders were placed and the "interview" begin once the drinks arrived.

She started by asking a bunch of internet dating website questions, do I have a dog, do I work out, and do I like long walks on the beach. I told her come on if this is an interview try something more in depth more challenging.

The next question floored me and I gasped for air, she asked "Have you ever fantasized about jacking off and cumming for a women?" I tried to play it off cool, and turned it around on her, "Why you ever fantasize about a man jacking off for you?" She smiled then looked furious a second later and said, "Remember the rules and this is a interview, I'm looking for someone who can honestly excite me. Waste my time and this will be a shortest date you ever been on."

I gulped, looked around and was saved by the food the waiter arrived and placed the over priced pasta in front of us. Mean while I thought about, all the time I spent as a kid jacking off in the shower did I fantasize about jacking off out of the shower and in front of another girl?

The waiter left she gave me a few more seconds then I said, "Yes, I have thought about it but mostly with other naked girls who were involved in the same activities." Then it was a whirlwind of questions and answers all pretty much about the same subject matter did I ever give head to another man, did I ever think about letting a woman fuck my ass with a strap on. It went on for over an hour.

All the time I noticed that I was getting turned on, across from me was Alison my dream girl visually, and was becoming my dream girl of fantastic sexual adventures. She seemed interested in everything and more. I wanted this girl more than you want a hot chick walking by more like you want a porn star in the movies because she's hot and is willing, a combination not to be taken lightly.

The night progressed and we were finally back at her place, and I was ready. All ready thought out what crazy shit I wanted to do I thought for sure I was finally going to get a girl to take it up the ass, already hard, and already in her spell.

On the front steps of here house she started to kiss me and I kissed back with everything I learned in French class. Things were heating up and I had my hands all over her and she was returning the favor. She then broke away from me flashed a smile batted her fuck me brown eyes and said, "Take off your shirt." My suit coat was already on the ground my tie was already half off and I worked the buttons of my dress shirt as fast as I could.

Alison meanwhile was caressing her body. The black silk cocktail dress danced across her body, the hem of her dress pulled up and my assumption was proved wrong, she was wearing panties. A quick half turn showed them off to be a g-string, the streetlights made the wet spot visible even from where I was standing.

My shirt off and said in a half chuckle, "Let's go inside, baby so I can do you right." She licked her lips and said, "Kiss me first." I walked over already half naked on the front steps of her house I noticed a car pass by and then felt lips touch mine. My attention was back totally on Alison. She started to lick and suck on one of my ears and I felt my belt unbuckle, by pants coming unzipped and then the cold night air on my bare ass.

Before I could offer a protest or say anything at all she moved around to my back and grab my rock hard cock with both hands. She pulled down by my cock and she put ear mouth close to my ear. All she said in sweet whisper, "Cum for me." Over and over she whispered that into my ear all the while tugging on my cock. She was rubbing me raw and I felt it.

I also felt all the pent up sexual tension over the meal and the trill of seeing another car drive by her house, while I stood completely bare ass except for my suit pants around my ankles. I could also feel the silk of her cocktail dress rubbing against my ass and back still while in he sweet whisper of a voice she said, "Cum for me." It didn't take too many more moments before I could feel my balls spasm and the cum flowing thru my hard cock. I shuddered while she milked the last bit of cum from my body and then she whispered into my ear, "Thanks, and call me tomorrow."

Next thing I heard was the door closing and locking behind me and then the realization that I am standing outside Alison's house completely naked and the fact I just came on my best suit coat.

I couldn't wait to call tomorrow.

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Jay DavisJay Davisover 18 years ago
More CFNM, please!

I love CFNM fantasies, and they are few and far between here. Can't wait to read more about Alison's control over the hapless but oh-so-fortunate narrator!

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