Getting to know Emily Ch. 02

Well after our meeting in the parking lot nothing really happened, nothing of significance anyways. We did start talking regularly, something we had never done before. Our text conversations were innocent enough, maybe a little bit of flirting, but never any sexting. We were both too scared to get to that point, both of us worried our significant other might look at our phone, not that that happened often, but could. Our relationship was rather interesting, while we were obviously attracted to each other physically, her mind was just as interesting. We shared very similar political beliefs and were both well educated, granted on opposite sides of the spectrum, hers a liberal arts degree in government and me in engineering with a minor in math.

This new relationship continued through the summer and into the new school year. Both of us were a little too timid to escalate things again. Obviously alcohol had some influence on our encounter at the end of the last school year. Our two oldest kids were Seniors in high school this year and we were both rather more involved with the school district this year, or at least I was. Emily being president of the PTO seemed to always be busy. But when we were planning the Senior trip, we both jumped at the opportunity to help chaperone the trip. It was like a free vacation. This trip was to an amusement park about 4.5 hours from home and instead of making an extremely long day and getting home well after midnight, the trip was funded for 1.5 days at the park with a hotel room for the night. The kids would be packed in like sardines but us chaperones were given rooms by ourselves. They obviously couldn't ask us to double up like the kids, as we tend to have an issue with sharing a room, needing a little more privacy.

There were 4 chaperones in total, 2 men and 2 women. This allowed for the maximum coverage of kids as well. We were leaving very early and showed up at the school around 5:00 am. My wife dropped me and my son off and said our goodbyes until tomorrow and she headed back home to get ready for work for herself. A couple of minutes later Emily was dropped off with her son as well. We were both carting large travel mugs filled with what I can only assume is coffee for hers and definitely strong black coffee for myself. We were traveling in 2 large tour buses instead of school buses, making the trip much more comfortable and it helped keep the kids well behaved as well. There were also TV screens throughout the bus and iron man was put on as a first choice of the available movies. The kids stayed pretty well behaved and luckily Emily and I were selected to ride together on this bus while the other 2 tackled the other bus.

We found seats together at the front of the bus and settled in for the ride. We barely listened to the movie, more keeping an ear out for trouble from behind us. We had a very pleasant conversation, not really talking about anything significant for a long time on the trip, really just catching up on things we haven't texted about or would be way too challenging to text about with our old thumbs. A few hours into the trip I asked her if she ever thought about that night. It had become this taboo subject in our texts and was almost an unwritten law that we didn't talk about it. She looked at me and got a resigned expression on her face, sighed and said she thought about it too often. I shifted in my seat to face her better and admitted I had as well. At this point we started talking more intimately. I admitted that things had been very lacking in the bedroom at home as of late. I mentioned that this could have been a serious contributing factor to last year. She then basically admitted the same to me. Her and her husband were just not intimate anymore and last year seemed to open a gate inside her. She was thinking about our encounter all the time, reading erotica, maybe not on a daily basis, but often. She had even watched some porn on her phone. She seemed a little ashamed of this and I asked her why?

She kind of got a shy expression on her face and admitted she felt a little dirty doing it, but it also excited her. I put my hand in her lap, holding hers and said... you know, sex isn't something that is bad, it isn't something you have to feel ashamed for enjoying it. She looked up at me and said she knew that but couldn't help the way she felt. I winked at her and said, Well it gives me something to work on then. She kind of got a half smile on her face. We looked up at the movie that was playing now on the bus and realized that the kids had moved onto Iron Man 2. We sat there in silence for a few minutes just watching the movie. At one point she put her head on my shoulder and appeared to go to sleep. She must have been tired as the movie wasn't exactly quiet, and my shoulder can't be that comfortable.

At one point I looked down and found my hand was now just in her lap, her hand now on top of mine. I smiled to myself at the opportunity I now had, squeezing her thigh to see if I got a reaction. When I got nothing more than a slight shift of weight, I pushed my luck further. I slid my hand down to her inner thigh and squeezed her thigh again. She signed this time and shifted in her seat slightly. In the process she slightly opened her legs a little more. This allowed me to slide my hand further up, my hand now on her upper inner thigh, just south of her pussy. I squeezed again and she sighed one more time, this time a little louder. Luckily, she was wearing some shorts as the weather was warm and my hands were mostly on her skin without the fabric of her shorts getting in the way, but if i were to go any higher, it certainly would be.

I tested things out and moved my hand to her pussy, rubbing it through her shorts. She softly moaned when I did this, so I continued rubbing her. During this she woke up, slowly at first then all at once all the way, realizing what I was doing to her. She clung to my arm for a moment, afraid of what I was doing, but excited as well. I spoke softly to her and asked if she was cold and needed a blanket? She got a kind of devilish look in her eyes and said yes. I stood up and got a blanket from a cubby and spread it out on her. I sat back down and proceeded to snake a hand back under the blanket where it was now safe from peeping eyes. To my surprise when I got there, I found her shorts undone and unzipped, and slightly pulled down giving me space to reach in. I pushed my hand under her panties, feeling her bush tickle my hand as I pushed deeper. Eventually my fingers were able to find her wet pussy.

As my hand enveloped her pussy, she groaned again on my shoulder, careful to not let herself get too loud and attract attention from the students. My hand curled up and started to rub her pussy, letting my fingers slide along her opening and drag across her clit. It didn't take long till she was responding very enthusiastically against me. She was thrusting her hips forward against my hand as I teased her. I could tell she was already close to cumming from only this little bit of stimulation, so I picked up the tempo, wanting to make her cum quickly with my fingers. To help things along, I let my fingers focus on her clit, wiggling my fingers against it, trying not to be too rough on it, but wanting to do more than just tickling it.

With this she groaned into my shoulder, barely keeping her volume below the movie. She bucked in her seat as her orgasm overtook her. She grasped my arm as she rode it out, digging her fingernails into my bicep. I carefully removed my hand from her pants and as I did, I made sure to bring my now wet fingers to my mouth to taste her. The taste was exactly as I remembered, and it made me hard just tasting it and the fact I was doing it in a crowded bus with teenagers on it, which included both of our son's.

I helped her get her shorts and underwear up without arousing any suspicion. After giving herself a minute to calm down, let her cheeks return to normal color, and her nipples to soften some and not be so obviously hard, she got up to freshen up in the bathroom on the bus. She came back a couple of minutes later, obviously refreshed and a little more put back together. She sat back down with me and whispered into my ear that her panties were completely soaked, with a little giggle at the end.

The rest of the trip went without incident and without any more touching. We got to the park shortly after it opened and re-explained the ground rules to the kids as we had already done it once on the bus. They each had money of their own, but the group already had arranged for a group lunch and dinner at the park. As it was about 10 am, lunch was arranged for 1 pm. The group dispersed and Emily and I paired off to go enjoy the park together as well. We chatted as we walked around about everything and nothing. We did ride a few rides that morning, but they were not the highlight of the trip. We met for lunch at 1 pm and the kids were well behaved, no issues with anyone. Our jobs as chaperones were actually pretty easy. We didn't have to do much, just make sure the kids stayed out of trouble, organize lunch, and get the kids to where they needed to be.

After lunch the temperature started to rise, so we focused on the water rides. This was always fun going with a woman as their shirts tend to cling to them much differently than men. The log ride was fun, we got a car to ourselves, but surprisingly, mostly our faces got wet and not the rest of our bodies. Switching gears, we hit the river ride. The one where 8 people get in a big tube and are strapped in and the tube bounces down the river, randomly hitting waterfalls and waterspouts. This ride was much more fun, although no drops or anything, the surprise spouts soaking us all and the waterfall that had a direct hit on Emily and I made the ride much more fun. Luckily all electronics are stored when you get on the ride, but she obviously wasn't dressed correctly for this. I had a tee shirt and athletic shorts on, she was similarly attired, but her shirt clung to her feminine figure, highlighting her breasts for all to see. The guys opposite her in the tube definitely enjoyed the show, but it wasn't until we were getting off that I was really able to appreciate it as well. The outline of her bra was clearly visible through her shirt as well as her hard nipples.

As we were getting off the ride, I gave her a little wink and looked down at her shirt. She gasped and pulled the shirt from her chest, pinching it between her fingers and holding it away from herself. Her hair soaking wet and pulled straight back just added to the allure. We found somewhere quiet to rest and give her shirt a chance to dry. I was laughing at her, which she seemed to take well. We took our time and rode a few more rides before dinner at 6 pm. The rest of the day passed without any other events of interest.

Everyone gathered at 9 pm to get to the hotel. The buses took us there and unloaded our luggage for everyone to grab. We looked like a mob attacking the lobby of the hotel. We were nice enough to give them a heads up that we would be there late and all at once. The chaperones went in to gather all the room keys. We had a total of 16 rooms, we pretty much took over an entire floor. All the rooms had 2 queen beds and the hotel was able to arrange things with the 2 sets of chaperones on each end, kind of like bookends.

We divided the kids into groups of 4, with only 1 room of girls and 1 room of guys being 2 and 3 students respectively. The sleeping arrangements were previously arranged, so there were no surprises for anyone. We had even arranged so Emily and I were on opposite sides of the hall on the same end. The other 2 chaperones were getting along as well, not sure how well, but this arrangement just seemed to work for everyone. We got everyone into their rooms, and settled down, by 11 pm, it sounded as if most were asleep. Kind of shocking for high school students, but it had been an early morning and an event filled, tiring day.

Emily and I kept our doors open during this time, just listening for trouble while we played cards in my room. We had a few drinks, careful not to have too many, we didn't want to get downright drunk while we were supposed to be watching the kids, but a little buzzed was nice. We decided to part company by 11:15 ish, with Emily retreating to her own room. I was a little disappointed that nothing more happened, but nevertheless, I was having a good time. The episode this morning and her wardrobe issue today had me slightly frustrated. I decided to freshen up for a minute. Brush my teeth and shave per my nightly ritual.

I then decided to chance things. I quietly opened my door, careful to not let it slam closed. At Emily's door, I texted her to open her door. It took her a minute, but when she did, I noticed she had changed into a long tee shirt, I didn't know what else as it was long enough to cover whatever else she may or may not have been wearing. When she opened her door, she had a quizzical look on her face and asked, what's up? I took this opportunity and moved in, letting the door close behind me. I wrapped my arms around her, pulling her in and kissing her deeply. She responded by moaning into my mouth. Her arms wrapped around me as well.

We kissed like this for a moment, and I pushed my tongue deep into her mouth as we kissed. I pinned her against the wall in the hallway of her room, not even making it to the living area. She responded to the kiss with more moans and sighs, obviously enjoying this. After a minute of this I pulled her away from the wall and walked her toward the first bed in her room. I broke the kiss for a moment pulling her shirt up and over her head exposing her naked breasts and black lace panties that covered her pussy. This was the first time I had seen her tits and I didn't miss the opportunity to pay ample attention to them.

As we reached the bed, I laid her back on it and followed her to the side so I could pay attention to her body. My mouth left hers and left a trail of kisses down her chest until my lips found her left nipple. My lips parted, allowing my tongue to tease her nipple, wiggling it quickly over her, making her nipple even harder than it was already getting. I started to suck on her nipple now, pulling it hard between my lips, making sure to continue to tease her nipples while I pulled harder into my mouth. She moaned louder when I did this, and slightly arched her back, seemingly pushing her breasts harder at my face. My right hand wasn't idle during this as and was pinching and teasing her right breast and nipple while I devoured her left. After a minute I switched breasts, leaning over her to suck on her right nipple that was already hard. I used my left hand now to tweak her left breast that my lips had just left. I sucked on her right breast now, drawing her nipple into my mouth, and teasing it with my tongue, flicking it repeatedly and swirling my tongue around it. I took a chance and brought my teeth down on it, not hard, but enough to make her jump and moan, her hands clutching the bed on both sides, and I continued my assault.

After a minute on her right breast, I straddled her stomach, while kissing and licking between her tits, my hands pinching and pulling at her nipples. She was moaning continuously now as I moved my mouth up to her neck and sucked and kissed it. I moved my mouth up to her ear, sucking and nibbling on her lobe, knowing how I love it and assumed she did as well. She was clearly enjoying herself now as I groped her breasts, pinched her nipples and sucked on her ear lobe. I let my lips leave her ear and find the way to her lips again. She kissed me hungrily as she reached her hands down, trying to pull my shorts down and was getting frustrated that my hands were still on her tits. She did manage to reach into my shorts, finding my cock already hard, and desperately wanting attention. I let her stroke me for a moment as we continued to kiss, our tongues seeming to dance with each other.

After a minute of this I broke the kiss and started to slide down her body. I left a trail of kisses on her chest, between her tits, down her stomach to the line of her panties. I grabbed the 2 sides of her panties and pulled them down and off of her completely, leaving her completely naked for me. With my right hand I used my thumb to rub her pussy, starting at the bottom and ending at her clit, pulling back the hood, exposing it completely to me. I leaned in and licked her, making sure to drag my tongue across her clit at the end. Nothing too aggressive, but enough so she definitely felt it. I heard her groan as I did this and did it slowly again, loving to tease her like this. She clamped a hand on the back of my head, holding me in place as I tongue fucked her. I thrusted it in over and over again, sliding it in and out, wiggling it while I did so. My thumb rubbed her clit even more, rubbing it harder and faster. I continued like this for a little bit, driving her arousal higher and higher. I was debating edging her at this point, wanting to tease her, but I knew she was dying for release and gave in. I licked her pussy with more urgency now, rubbing and licking her pussy harder, taking her over the edge and letting her cum for the first time tonight.

I paused my efforts on her pussy as she climaxed, giving me a chance to breathe for a moment as well. As she came down, I switched and started to lick and suck on her clit as I pushed a finger into her pussy. I slid my finger deep inside her, only stopping when my palm was pressed against her pussy. I started to slide my finger in and out of her as I sucked and nibbled on her clit. As she got closer and closer to another orgasm, she held my face harder and harder against her pussy. After a couple of minutes, I replaced my single finger in her pussy with two instead. She let out a deepthroated groan with this and started to grunt with each thrust. My tongue enthusiastically licked her clit as I finger fucked her. She didn't last long from this attention and climaxed very hard, squeezing my fingers as I continued to slide them in and out of her.

I moved my face from her pussy now, her juices dripping off me, and moved back up to her face and kissed her again. By this time, I was extremely hard and desperately wanted to fuck her. I stood up and pushed my shorts and boxers down, exposing my cock to her. I then removed my tee shirt as well, leaving us both completely naked. She got a hungry look on her face looking at my cock, but I didn't give her a chance. I grabbed her legs and pulled them up. She got a surprised look on her face but seemed to enjoy me taking charge as well. I held her legs up with one hand and aimed my cock at her pussy with my other. I toyed with her for just a moment as I brushed my cock, wet with precum, against her pussy and clit.

She was begging with me now to fuck her. I pulled back just slightly and pushed in hard, burying myself in her. She groaned with the pleasure of it. She seemed to not know what to do with her hands, alternating between grabbing my ass, squeezing her breasts to holding onto the bed. I didn't wait for her to figure out what she wanted to do and started to fuck her. I repeatedly pulled back until I was almost out and slid back in until I was deep within her. With each thrust her arousal grew. With each thrust her frustration also grew that I wasn't going faster. I liked teasing her like this, sliding in and out purposely slowly. I grabbed her ankles at this point and put one over each shoulder and continued the excruciatingly slow pace. After what felt like forever, and even longer for her, I modified my pace. While continuing to slide out slowly, I started to push in fast and hard, surprising her the first time. While she had been almost sighing with each push before, she now let out a groan this time as I slammed into her.