Starting My Career
written by:
oppy-n-rose

I gathered a few papers and finished getting myself ready before heading off to my first day at my new job. I had applied for a teaching position in the local school system and was hired as an aide to a first grade teacher who would be leaving the class at the end of the school year. My job was to work under him and have him basically show me how to run the classroom. Hopefully, if all went well over the next several months, he would tell the school board that I was the one to take over his class. I was a nervous wreck heading into this, but knew that I had to do my best in order to achieve my goal of finally becoming a schoolteacher.

I arrived at the school a short time later and after being given a quick tour, I headed to the classroom to go over a few things with the teacher before the school day started. I walked in to the classroom and he was already there. His name was Tony and he looked to be in his mid-40s. He quickly walked over and greeted me and the two of us chatted for a few minutes as he asked me a couple of quick questions. He went over a few things with me and once everything was all set, we sat and waited for the kids to arrive. The school day eventually started and I sat off to the side and observed how Tony ran the classroom. I did this for the next couple of hours, before heading to lunch in the teachers lounge. Tony showed me around and even introduced me to some of the other teachers before we sat and had lunch. He seemed pretty friendly and told me that he was hoping to move on to the local high school after the school year. We discussed it for a bit while enjoying our lunch, before eventually heading back to the classroom. The rest of the day was spent in the same manner, with me sitting off to the side while he taught the class. I learned a few things right away that day and was excited to finally be given a chance.

The next several days were pretty much the same, where I would come in and observe as Tony taught the class. Every day was basically the same thing, as he would teach the class and then we would take a break for lunch before going back to the class once again. This essentially took place for a couple of weeks before I finally got a shot to teach. Tony came in that morning and said that he would like me to student teach the class so that I could get the feeling of being in charge. I was a bit nervous but did my best and the students were pretty receptive to me, which was a big help. I noticed Tony sitting off to the side, watching my every move and assumed that he was observing what I was doing. I was able to teach the class several times over the next couple of weeks and was very happy to be able to do so. As I did, Tony began complimenting me and telling me that I was doing a phenomenal job. He helped me build my self-esteem as I became more comfortable standing in front of the students. This was pretty much the way things went over the course of the next few months, as we would take turns teaching the class and Tony was always very helpful whenever I would teach.

One thing that I did notice over the course of that time was Tony becoming a bit friendlier with me. I guess it was normal, since we spent so much time together on a daily basis. We would always have lunch together in the teachers lounge and always engage in pleasant conversations. He complimented me often, which was a big ego booster for me. I wasn't getting many compliments at home nowadays, so it was nice to hear pleasant comments coming from someone else. I also noticed that Tony would playfully flirt from time to time and I really thought nothing of it. If anything, it was nice to hear. Every now and then, when I was in a good mood I would playfully flirt back with him and it helped make the days go by faster. I never really thought much of it and just figured that he was being nice. This all went on for several months and after a while, I noticed that he would always have his eyes glued to me whenever I was in the class. At first, I thought maybe that he was just watching my posture and to see how I handled the class, but after the flirting began, I started wondering if maybe he was checking me out instead. I knew that he was married, but I guess a guys going to look if he wants to. After all, that wasn't such a bad thing because like I said, I wasn't getting much attention at home lately and to have someone checking you out, especially after having a baby and not being able to get rid of the baby weight, it definitely made me feel good. I won't bore you with particular details, but this pretty much went on for the rest of the school year. We would come in to work, chat with each other whenever the opportunity presented itself and he would playfully flirt with me here and there. Overall, I was enjoying the teaching experience and Tony was making it that much more pleasant.

After several months of this, Tony and I were very comfortable around each other and often enjoyed each other's company. One afternoon as we were packing up after school had ended, we were chatting when Tony thanked me for making the year go by so quickly and easily. I thanked him for the opportunity and hoped that I had impressed him enough so that he could make his decision. He told me that I was doing a phenomenal job and really enjoyed having me in the classroom and with that, he was hoping that I would accept his invite to go out to dinner that following Friday night so that we could discuss it some more. I was caught a bit off guard by his invite, but quickly accepted it, thinking that it was probably a good idea if I went because I really wanted him to choose me as his successor. He seemed happy and gave me all the details about where dinner would be. After setting everything up, we finished up with our work and headed home.

The next couple of days went by as usual before Friday arrived. After work, I headed home to get ready for that night's dinner with Tony. I told my husband that I would be heading out to dinner in order to discuss my future teaching position and he just told me to go have fun and wished me luck. I took a shower before heading into my bedroom to decide on an outfit. After looking at a few things over, I settled on a skirt and dressy blouse. I dressed myself up before putting on some makeup. Once I was ready, I headed out to meet up with Tony. I was a bit nervous and wasn't really sure as to what I should expect. I assumed we were going to discuss the teaching position over dinner, but in the back of my mind I also reminded myself that Tony had flirted with me often. I know that it never evolved into any serious flirting, but was still in the back of my mind. I made my way to the restaurant, arriving a short time later and was impressed by the place. It was a very elegant establishment and I looked forward to enjoying a nice meal along with a night out. I headed inside, and Tony had already reserved a table for us. We were seated and he quickly ordered a bottle of wine when the waitress came over to our table.

The wine arrived and the two of us began to chat as we enjoyed a glass of it. Eventually, we ordered our dinners and once they arrived, we ate and enjoyed them as well. Throughout dinner, we chatted about many different subjects and I was really enjoying the evening. Tony was being quite the gentleman and I found myself enjoying his company. As he had done in the past, he flirted with me while we chatted and complimented me as well. I enjoyed all of it as it made me feel great. We had a wonderful dinner together and it was a very pleasant experience as I hadn't been out to eat in quite a while. After finishing dinner, I went to use the restroom while Tony took care of the bill. When I exited the restroom, Tony was standing nearby and I noticed that he had a bag in his hand. He quickly reached his arm out to me and I decided to wrap my around his as we walked arm in arm out to the parking lot.

He walked me to my car as we continued to chat. Once we arrived at my car, we stood face to face as he thanked me for coming out to dinner. I thanked him for treating me and told him that I had a great time. He responded by telling me that he had a great time as well and was wondering if we really needed to end the night already. I told him that I wasn't in a big rush and asked what he had in mind. With that, he reached into the bag and pulled out a bottle of wine, just like the one we had been drinking at dinner. He held it up and told me that his wife was out of town with the kids and wondered if I was interested in stopping by for a little while and having another glass of wine, so we could discuss his decision. At the moment, I wasn't sure how to react and wondered if this was a very good idea. I knew that if I said no, I would probably be hurting my chances of taking over the classroom. At the same time, if I said yes, I might be putting myself in a regrettable situation. After all, he had flirted with me all night throughout dinner and going back to his house with him was probably not the best of ideas. I only had a split second to make a decision and against my better judgment, I decided to go. Hopefully, it would benefit me and work out for the best. Then again, maybe I was just looking way too far into this and he was just being nice and inviting me over for a glass of wine. Either way, I was nervous as I got into my car and started it up. He headed over to his car and after starting it up, he began to drive as I followed.

As I drove along behind him, I began thinking about a bunch of different things. First thing was me asking myself what the heck I was doing, following him to his house. I continued to be naïve and tell myself that he was just being nice and inviting me over for some wine, but the other part of me kept saying that there was more to it than just wine. My mind was racing but before I really had time to react and think any further of it, we were pulling up at his house. He pulled into the garage and had me park in the driveway behind him. After parking my car, I got out and headed over to where he was standing. He had a very nice-looking home and I was pretty impressed. He unlocked the front door and invited me in. I followed him and we made our way into his living room. Once inside, he gave me a tour of the house before we ended up back in the living room.

I stood and admired a painting that was hanging on the wall as he headed off to the kitchen to grab a couple of glasses for the wine. He returned a minute later and filled the glasses before handing me one. He then held his up and toasted to a wonderful evening. After toasting, we each sipped the wine as we stood in the living room. As I stood and continued to admire the painting, Tony walked over to his radio and put some music on before walking back over to where I was. As he walked towards me, he came behind me and started rubbing my shoulders while telling me to relax. He told me that I looked tense as he gently rubbed my shoulders. I took another sip of my wine before closing my eyes and enjoying the feel of his fingers as they worked my shoulders. He did this for a few minutes before I felt his lips kissing the back of my neck. It quickly dawned on me that this was really happening. Just like that, without any romance or anything else for that matter. At that moment, I had a very important decision to make. I either stopped this dead in its tracks, and probably throw away an opportunity at a teaching career, or I stand there and let him do whatever he wanted to do and hopefully it worked out for the best.

As I stood there with everything running through my mind, Tony continued rubbing my shoulders and kissing my neck. Slowly, I felt his hands go from my shoulders down over my blouse, where he began to unbutton the top button. I didn't move or react and I guess he took that as a go-ahead. He slowly worked his fingers down to my next button and after undoing that one, he went to the next one and continued that until he had fully unbuttoned my blouse. After undoing all the buttons, he slowly slid my blouse off before working on my bra. He unclasped it and slowly slid it off, leaving me topless in front of him. After taking it off, he reached around from behind me and squeezed both of my tits as I continued to stand with my eyes closed. He did this for a few minutes before reaching down to my skirt and lifting it up around my waist. With one hand on my tits, he slid his other hand into my panties and began to softly rub my pussy. I couldn't help but respond to his touches as his fingers found their way inside of me. It had been a little while since I had been touched, and this was really starting to feel good. As wrong as it was, I wanted him to go further.

He stood behind me and slowly fingered me for a little bit as he continued squeezing my tits with his free hand while still kissing and sucking on the side and back of my neck. After doing this for a little while, he took his fingers out of me and led me by the hand, out of the living room. We made our way through the house, to his bedroom where he laid me on the bed before undressing himself. As he took off his clothes, I noticed his cock spring free from his boxers. It wasn't the biggest cock that I had seen, but was still somewhat impressive. After undressing himself, he climbed back onto the bed and positioned himself between my legs. Slowly, he lowered his mouth to my nipples and began to kiss and suck each of them while squeezing my tits. As he was doing that, I could feel his cock rubbing against my pussy. I began to get a feeling of excitement, as I knew he would be inside of me at any moment. This was it and there was no turning back now. He was going to get what he wanted and hopefully after all was said and done, I would get what I wanted.

After licking and sucking my nipples for a little while, I felt him reach down and grab his cock. He rubbed the tip against my opening, getting it nice and wet. Once he was wet enough, he slowly pushed forward, penetrating my pussy and burying his cock inside of me. At first, he didn't move as he laid and enjoyed the feel of his cock inside of my pussy. After a few moments of this, he slowly began to thrust, driving his cock in and out of my pussy as I gripped the bed tightly. I won't lie, his cock working its way in and out of me felt very good and I found myself enjoying the moment. I figured if I had gone this far, then I might as well enjoy it.

He took his time, fucking me slowly as we both enjoyed the feeling of what was happening. As he thrust his cock deeper and deeper into me, I began to get a feeling that I haven't felt in quite a while. Whatever he was doing, felt great as I could feel an orgasm coming on. It had been months since I had experienced one and I couldn't believe that it was this easy. Usually, it took my husband a while, using my toys in order for me to experience one. Tony managed to do it by just slowly fucking me. He continued to thrust as I wrapped my arms around him and tried to pull him in tighter. This caused him to pick up his pace a bit and that brought me even closer to my orgasm. Within a few moments of him increasing his speed, I tensed up and held him tightly as I began to cum. I let out a loud moan as I convulsed and came hard all over his cock. He continued fucking me as wave after wave of bliss shot through my body.

After a little while, I finally came down off my high and loosened up my grip a bit on him. He continued thrusting into me and I knew it was only a matter of time before he climaxed as well. I closed my eyes and enjoyed the feeling of his cock as he pushed it deeper and deeper into me. He did this for another minute or so before finally tensing up and exploding deep inside of me. He continued to thrust as he shot wave after wave of his hot seed deep into my pussy. It felt amazing to have another man's hot cum inside of me as I used my pussy muscles to milk him up every drop. Once he was done, he climbed off of me and laid by my side as we both tried to catch our breaths.

After lying for a little while, I noticed his cock starting to come back to life and decided to take over. I reached out and began to stroke it, getting it back to full hardness before climbing up on top of him and straddling his cock. I lowered myself onto him and his cock easily penetrated my cum soaked pussy. After lowering myself onto him, I began to slowly ride his cock, taking my time and enjoying the feeling yet again. This time around, he lasted much longer as I rode him for quite a while. I enjoyed the feeling as I bounced on his cock and as I was doing that, he reached up and played with my flailing tits. We were both into the moment and fully enjoying what was happening as we both experienced the pleasure of pleasing each other. He eventually erupted inside of me yet again, flooding my pussy with even more of his hot seed. I made sure to ride him until he had shot off the last of his load and then climbed off of him, and collapsed onto the bed as I tried to catch my breath.

We ended up spending a couple more hours together that night, as I made sure to let him fuck me as much as he could. Even though I did what I had to do to secure my job, I enjoyed the experience. Tony knew how to fuck a woman properly and he showed me that night. I ended up getting the job as I had hoped and even though the classroom was mine, Tony and I continued to go out to dinner whenever his wife was out of town...