Getting to know Emily

Although I am not officially associated with the school system, I am well known and well respected within the school district. The teachers knew that I was providing a necessary service and valued my contribution to the educational system. Beyond tutoring the students that needed help, I was also involved with several charity operations in town and volunteered with the PTO as well.

Through these activities I have kept a rather active social life. I got to see the families of those students I have tutored in the past, finding out how well they are doing as functioning adults now, and got to know other families that have never hired me for my services.

There was one family that I had gotten to know through these groups, but never had the privilege to work for them, the Levine's. The mom, Emily, was the president of the PTO and very active in the community. Never saw much of her husband, but her kids were bright and were top in their respective classes. Emily always looked, just so, hair done perfectly, never dressing too provocatively and never a hint of controversy around her or her family. Tonight she was dressed in a stunning black dress that seemed to cling to her body while not making her look slutty at all, in fact the exact opposite. She looked very sophisticated, she seemed to exude charm and class from her immaculately pedicured and painted toe nails, up to her very stylish hair. She had a take charge personality as well, something that always intrigued me with women. I have always been attracted to strong intelligent women and Emily was no exception.

Emily and I have always gotten along well, just never more than a professional relationship.

This changed one night in a way I would have never thought possible. This event was at the end of what seemed like a very long school year. It took place at a local restaurant that served nice food that wasn't overly priced. The drinks were flowing as usual and people all around were enjoying themselves. What didn't strike me as odd to begin with was that Emily had a drink.

I have seen her drink before, but very sparingly, rarely more than one, and certainly never to excess. This time was a little different, she seemed to be a little more chatty than usual and she was obviously on her second drink with an empty infront of her.

I made my way over to her to strike up a conversation and we started talking about everything and anything. As she finished her drink I offered to get her another which she readily accepted to my astonishment. I brought her another Long Island Ice Tea and we continued our conversation. Throughout the conversation some subtle changes had come about her. Several hairs had come undone from her normally pristine hair do. Her normally reserved manner had cracked some as well, while not overly loud, she was definitely louder than normal for her. She also seemed to be touching me more and more to emphasize points while talking. She was obviously enjoying herself immensely, and who was I to tell her she couldn't, especially since I was the focus of her attention.

We continued our conversation, probably the longest we have ever talked one on one ever. The rest of the get-together seemed to fizzle out after a while and we found ourselves alone as the rest of the group had left for their respective families and homes.

We were both a little buzzed at this point and we both found this actually amusing that we had lost track of time so much. While it wasn't late, only about 9 pm, we were now alone after the rest of our party had left. We continued to talk and learn more about each other and found we had a lot more in common than originally thought. We were both in long term marriages, all kids were at least of an age they could take care of themselves and we were both done having kids.

As we chatted, we got closer and closer, eventually her hand rested on my leg, mine on hers. As she continued to talk, I slid my hand further up her leg, making her catch her breath for a moment and then continue on as if nothing had happened. I took this as a challenge and proceeded to massage her thigh slowly, letting my hand slide further up and further between her legs with each knead. I could sense a little sparkle in her eyes as I continued this attention. She shifted her weight slightly, seeming to get more comfortable. She tried to continue talking as if nothing was amiss, but I could tell she was starting to struggle. She would pause to find words when I would squeeze her thigh, especially when my hand was on her inner thigh. At one point there was a line to be crossed, before then all i was doing was massaging her leg, the next step would be to be actively rubbing her pussy through her dress.

She seemed to sense this turning point as well and gave me a blazing look that portrayed all the passion, all the need I was feeling as well. All the lust for lack of a better word. I moved my hand slightly, letting just my finger tips graze over her crotch. She gasped involuntarily at this and her breath caught in her throat. She tried to continue what she was saying and pretend nothing was happening but failed miserably. I picked up the thread and started talking to her as if nothing was happening, as if I wasn't rubbing her pussy in a crowded restaurant. I continued talking to her, rubbing her pussy more and more, she was definitely aroused now, her nipples were poking against the fabric or her dress and I could see a fine sheen of sweat on her body. She seemed nervous but was doing nothing to stop my ministrations. After a few minutes of this she closed her eyes, and let out a small, obviously restrained moan and let her body relax. It seemed as if she had just had an orgasm in the restaurant, only to find out later it was indeed the first orgasm of the night that she had.

She looked at me after this, taking deep breaths, biting her bottom lip, something that was decidedly not a very sophisticated look. I asked her if she wanted to get out of here, which she enthusiastically said yes to. I paid the check and we left, her in front, me following. I had found a parking spot out front, fairly close to the entrance when I arrived, but her car was out back. I walked her to her car wondering what might happen next. Her car was in a rather secluded area of the parking lot, not well lit, which suited my needs nicely. As we got there I turned her towards me, and kissed her for the first time.

What happened next I can only describe as an explosion on her end. She seemed to come alive in my arms, kissing me back fervently. Her lips opened greedily and accepted my tongue as I kissed her. Our tongues danced with each other, teasing each other. Her hands were now on my back and ass as we kissed, pulling me into her. My hands were on her back as I pushed her against her car, making sure she could feel my arousal as we kissed. I reached down and cupped her ass with my hands as we continued to kiss. Our makeout session got more hot by the moment. After I massaged and groped her ass for a few minutes I let my hands work their way up to her tits, feeling them restrained in her dress and bra.

Her nipples were still hard, I could feel them through the fabric. I didn't spend too much time on her tits though as I really had other activities on my mind tonight. Looking around to make sure we were still alone I pushed back up against her car and proceeded to make my way down to her pussy with my mouth while my hands raised her dress. I found her pussy covered with a pair of black lacy panties that smelled delicious with her arousal. I paused for a moment, just to take the scent in. Her hands were on the back of my head, holding me, not sure what else to do. I leaned in and licked her pussy through the fabric of her panties. As I did this I could hear her moan from the pleasure and she put one hand on her car for support.

I pushed harder this time while licking her through her panties. Letting the rough material slide against my tongue. I reached up with a hand and slid her panties to the side, exposing her pussy to me for the first time. I renewed my assault on her pussy now that I had complete access to it, sliding my tongue completely up her pussy, making sure it hit her clit at the end. A groan escaped her lips at this point and I could feel her pussy get even wetter. I slid my tongue into her pussy this time, probing at her depths, and rubbed her clit with my thumb. She groaned again at this feeling and I felt the hand on my head squeeze and pull me closer. I started to tongue fuck her, thrusting it in and out the entire time, sliding it in and tasting her juices with each thrust. My thumb was drawing circles around her clit, occasionally rubbing against it, but trying to heighten her pleasure more than just make her cum. I moved my lips up to her clit as I pushed a finger into her pussy, making her moan again with the pleasure of it.

I pushed my finger into her hard and licked her clit at the same time, making her shudder this time. I started to fuck her with my finger, sliding it in and out, and redoubled my attention on her clit. I sucked it between my lips, and repeatedly flicked it with my tongue. With this she seemed to come alive, pulling me closer to her with her hand while thrusting her pussy hard against my hand and face. With each push into her she seemed to reach another level of pleasure. As I pushed a second finger into her, she seemed to explode and melt on my face. She started to moan and buck on me. She moaned much louder than previously and pulled her hand off my head to stifle her own sounds, and let out several grunts as she orgasmed hard on my fingers, squeezing them.

I stopped finger fucking her and let her come down off her high. I stood up and looked at her face, noticing the glazed look in her eyes as she focused on me. She had an hungry look in her eyes as she looked back at me. I leaned in and kissed her again. This kiss was a little different than the others. Gone was the initial lust we had earlier, it was now replaced by a feeling of need, a feeling of desire. She hungrily kissed me, seeming to love the taste of her juices on my face.

We kissed for a few minutes until she pushed away from the car and turned us around to push me back against it. Her hands reached down and undid my pants while we continued to kiss. She pushed them down, making sure to collect my boxers at the same time. After a moment when my hard cock wouldn't let go of my boxers she succeeded in pushing them to the ground. With a deft hand she grasped my cock, stroking it while we continued to kiss. After a minute of this she knelt down in front of me, admiring my cock for a moment and slowly licking my cock's underside from balls to tip. I definitely groaned as she did this, loving the feel of her tongue on my cock.

She got a kind of hungry look in her eyes as she looked up at me. Without breaking eye contact she proceeded to slide my entire cock into her mouth. While I am not huge, I am not small either. I guess somewhere around 6 inches, from what I have heard that is about average. But I still had never had this done to me. My wife did not like giving blow jobs at all, and this woman obviously enjoyed it. As her lips sealed around the base of my cock I could feel her tongue rubbing against the underside of it as she slowly slid her head back up my cock. As she pulled back so just the head was left in her mouth, she increased suction with her mouth and slid all the way back down again. I was in heaven.

She continued like this for a few moments, using the full length of my cock in her mouth, pleasuring every inch of it. After a few minutes though she picked up the pace. With her right hand she grasped the base of my cock, with the other she started to massage my balls. She used her hand on my cock to stroke me in rhythm with her mouth. As she slid down my cock her hand would go down as well, as she ascended, my hand would as well, all the while her other hand massaging my balls, driving me nuts.

She got a rhythm of this going and started to pick up the pace, sliding her head up and down my shaft with increasing speed. Her saliva let her hand slide freely on my shaft as well, allowing her to grip more tightly and milk my cock of any precum I had available. I let her continue this for a couple of minutes, loving the feel of it, but I really didn't want to cum like this. While it would be fantastic, I had something else in mind. It got to a point when I had to stop her, and pulled her up. She had a slightly disappointed look in her eyes but let me pull her up. I turned us around again and leaned in to kiss her pushing her against her car again.

This kiss was yet again different than the previous one, this one exuded passion, need, desire. My cock was rubbing against her stomach, making her dress sticky with her saliva and my precum. I turned her around this time, letting her ass rub against my cock, with her dress bunched up around her waist where it didn't encumber my efforts. She pushed her ass back against my cock, making it slide between her cheeks and up, making me feel incredible. I pulled back for a moment, taking charge of the situation, and pointed my cock forward, pushing forward until I was at the entrance to her pussy. I paused there for a moment, letting her know what was coming. She looked back at me, that hungry look still in her eyes.

Grabbing her hips, I pushed my cock into her pussy in one shot. Sliding it in until I was fully inserted, the feeling was amazing. She was so tight on my cock, and the look on her face as I pushed into her was pure heaven. I took a moment to acclimate myself to her pussy before I started to move. It felt so amazing I didn't want to cum immediately, and if I wasn't careful, that is exactly what would have happened. We both waited for a moment, her leaning forward, holding onto the car, me buried full hilt in her pussy from behind. After I collected my self, I started to fuck her. Sliding my cock out, left me feeling wanting and couldn't wait to push it back in.

I started out slow, sliding my cock in and out of her at a measured pace, not going too fast. After a minute of this though I lost my cool and started to pick up the pace. I started to slide in and out of her faster and faster. My cock seemed to fly into her. Her pussy clenched me so tightly as i fucked her. I slide it in repeatedly, over and over again, pushing harder with each thrust. I could hear her panting with pleasure and I was grunting with each thrust. I continued to fuck her, all sense of time and space lost. I was slamming into her now, oblivious that anyone might see us. This continued for a couple of minutes and finally it was too much.

My cock seemed to swell inside of her as I neared my orgasm. She seemed to sense this as well and started moaning even louder, thrusting her ass back at me while I pushed in. After only a few thrusts like this I felt her pussy clamp down on me as she came for a 3rd time. This sensation was too much for me. I slammed into her a few more times, feeling my balls slap against her pussy with each thrust. I told her I needed to cum and she begged me to cum inside her. I finally reached my climax and slammed into her, holding her against me as my cock erupted into her repeatedly. My cock seemed to be spasming inside of her, twitching with each pump of cum deep inside her.

As we came down off our climaxes we both kind of looked at each other and were like, what the hell just happened. I leaned in and kissed her again, this kiss passionate, maybe with a promise of more to come, but also seemed content for the moment. We kissed for a few minutes and then kind of came to our senses... we were rather exposed, me more than her with my pants around my ankles. We both composed ourselves quickly, me pulling my pants up,she just needed to pull down her dress.

We talked for a few minutes, neither really sure what to say, realizing that a line had been crossed we would never be able to get back. We talked for a few more minutes and then again another startling discovery was that it was almost 11 pm. We decided we had pushed our luck enough and departed for our separate houses after exchanging numbers. I couldn't believe the way the night had progressed, I would never have thought we would have hooked up like that. There was something rather exciting about it. Both the fact we had just had sex in public and the fact that this prim and proper woman and had just let me fuck her and cum inside her.

I headed home, knowing that tonight might only be the first occurrence, and wondering when and where we could possibly repeat that.