A Teacher's Tryst Ch. 01

Nearing my 32 birthday and still being single I decided to peruse the personal classifieds on craigslist. I wasn't sure I was looking for anything in particular or even anything I would act on but what I found turned out to be something more than I could've imagined. I found an ad that seemed harmless and responded. The ad read:

"I'm a MWM, 65, 6', 200# ISO older lady with a vivid imagination and a great libido. I'd like to trade erotic thoughts, stories and fantasies with you. I have no desire to meet, but if writing naughty turns you on and you would like to share the amazing subject of se from your point of view I'd love to reciprocate. Please give me a try."

I had never been drawn to men that considerably older than myself. I never had daddy issues or fantasies of that nature but there was something in his ad that made me curious. Perhaps the line saying there was no desire to meet pushed me to hit reply. Whatever the case may be, I typed an email and pressed send anticipating it would never be answered but boy was I glad it was.

I found out his name was Bill and we started slow. He was stunned to learn I was younger than he had anticipated but it served as little deterrent. We began by asking and answering questions and feeling out how this would work. I told him I was a teacher as well as some other less personal things about me. I learned his wife was unable to satisfy him due to surgery she had had and that he had had some affairs. As we continued to talk I couldn't help but fantasize about my own affair with Bill. I wasn't expecting to feel that way, again what had drawn me to him was the fact that he didn't have the desire to meet, but reading his stories of the affairs he had, made my thoughts run wild. We continued to email for over a week when I sent him my first fantasy: "A Teacher's Tryst", where our affair begins. Below is a direct transcription of the email I sent.

I've talked you into meeting me for coffee because I want to talk to you in person (hear your voice, smell your cologne, make this experience real, etc.). In reality I have planned that I will convince you to fuck me.

We meet for coffee, you looking very distinguished in a button up shirt and blazer but still showing your youth in a pair of semi tight dark denim blue jeans. When I see you walk in I immediately squirm pressing my legs together as my pussy starts to leak a small bit. My arousal starts knowing it won't be an easy task getting you to agree but hoping you will.

You walk over to the table I'm sitting at and lean in giving me a small peck as though we've met a thousand times before. It's a small reassurance that maybe I can convince you.

I'm wearing a pair of mid thigh navy shorts and a pink off the shoulder top. My summer tan making my skin look delectable. I've curled my hair and it cascades in a way framing my breasts just so. I ask what you'd like to drink and casually walk up to order hoping you watch my ass as I walk by. I smirk devilishly as I glance back and see you looking.

When I return I let our hands touch slightly longer than need be as I hand you your coffee. The spark between us is electric and I could swear I see you shuffle in your seat as an attempt to conceal your growing bulge.

We talk aimlessly for a while. You ask how graduate classes are going, I ask if you've been golfing lately, small talk. Then you turn the subject to sex bringing up one of your affairs. I'm all too happy to listen. I picked a booth in the back corner just for this purpose; so we could be concealed from others trying to listen in. I inch closer to you however, becoming more and more turned on as you speak. At one point while you're talking I put a hand on your thigh and you seem to pull away at first pausing in our story, but then a wave of calm settles over you and you continue on. I decide to leave my hand there a second longer rubbing my thumb over your thigh. A seductive look fills my eyes.

When you finish I seize the moment and lean i to whisper that I chose to go commando. I know I'm in shorts but knowing I was going to see you I just had to. I wanted to make you happy. You glance down quickly as I tell you and then our eyes lock on mine. You can tell now what my plan is and for a second I fear you're going to get up and leave. It surprises me when you don't but you tell me sweetly that it can't happen. I understand but you can see the disappointment in my eyes and my head sinks. You slowly lift my head by chin stroking my lips with your thumb apologizing. I say there's no need that I should've known it couldn't happen from our conversations before.

We grab another cup of coffee and continue to talk. I tell you of fantasies of mine and you share yours. As we leave we hug and again you give me a peck on the lips that I wish would last longer. I tell you I will always be ready if you change your mind and you kiss me again. I let you know that I had booked a hotel in hopes that we could reenact one of your affairs and that I plan on going and making myself cum to the thought of you. You walk me to my car as a gentleman would and again kiss my lips this time a bit more fervently. I know you would love to come with me but you can't allow it. As I see you walk away in my rearview mirror a hand goes to my already wet pussy. I know I won't be able to make it to the hotel. I have to have release now.

That's when you turn around and it's too late for me to stop. You walk up and see me fingering myself and it's all you need to persuade you. Before I can say anything you've gotten into my car and replaced my fingers with your own covering my mouth with yours. You break free from our kiss long enough to say "I can't wait to feel your cunt around my cock you sweet little slut." I purr in anticipation and smile at the fact that I know I've become your third lover and I'll let you use me however and whenever you want.