Tutoring Adventures Ch. 01

I swear when I started tutoring it wasn't with the intention of hooking up with my students or their family members. I always had the best intentions as I really do enjoy the work. Teaching has always been a passion of mine, whether it be in a larger setting or one on one. But, given a choice I do prefer the one on one, giving individual attention to a struggling student and making a difference in their education and life.

Through the years I have tutored kids as young at 14 and parents as old as 48. I also always try to be very professional and respectful. I have also tried to take extra special care to not put myself into situations that could lead to accusations with female students specifically, especially the underage ones. Inevitably through the years there have been some slip ups of mine. Encounters that have led to experiences that were exciting, erotic and while legal, not something I could ever tell my wife about.

A little about me. Currently I am a 49-year-old engineer, still struggling to make ends meet, partly because both me and my wife have expensive tastes. But knowing this I keep tutoring on the side to help afford these extravagances. I have been tutoring for about 20 years now and have thoroughly enjoyed it mostly. There have been a couple of students I would rather have never met, but I learned from them to set up my expectations early with them. I am also married 22 years now and have 2 kids, the youngest being 14, oldest 20. While we are still in love, there has been a lack of passion in the relationship for a long time. These series of stories will follow my experiences that I could never share with my wife.

Before this first time there were times I was definitely tempted, but I never actually acted upon my temptations with students or parents. The first time will forever stick into my brain though, as they always do. She was 18 years old, in her senior year of high school, desperate to pass her math class that was required for graduation. Her name was Jen, a petite brunette with long hair, tight body with smaller B cup breasts. She was also a hard-working student that just couldn't seem to grasp some of the concepts. As I tell lots of people, my job as a tutor is to translate what their teacher says into language the students can understand, this was no exception. After the first few sessions I could see she was starting to be able to translate some of the instructions herself, starting to be able to grasp the concepts with less and less interaction from me.

Throughout our time tutoring she became more and more relaxed, able to joke around more with me, much more comfortable. Our conversations didn't always revolve around her homework, or the math test we were studying for. She was comfortable now to do the work, while starting to converse on a more personal note. This is the best part about being a tutor, when you get to see this amount of success from a student.

One particular session she started talking about her boyfriend and a recent fight they had. I could tell he was an asshole just from how she described him, and I once again wondered at how a lot of very attractive women dated men that were just complete assholes and never treated them with the respect they deserved. It turns out she had caught him flirting with another girl and rightfully she didn't appreciate this. I made a comment about how disrespectful that was and if I was him, I would never do that to her, and she could do so much better. She stopped what she was doing and looked at me with a quizzical expression, pencil at her lips and said, oh really?

I realized at that point I may have slipped up a little and torn down some barrier between us. I didn't really think anything about this as nothing transpired after this in that session. It was a week later during our next session that something happened I wouldn't have thought possible. When I arrived, she was wearing some athletic shorts and a t-shirt, nothing out of the ordinary although the t-shirt was a little more revealing than she normally wore around me. She seemed in very good spirits, and she did very well during that session. While we were working, we started talking as usual and she mentioned she broke up with her boyfriend over the weekend. I was a little surprised, but very happy for her. She told me it was thanks to me that she took that leap. My offhand comment that she could basically do better she took very seriously. As we were nearing the end of our session her mother stopped in to see how we were doing and informed us she needed to go out and run some errands. She paid me for my time and took off.

This is where everything changed. After we finished tutoring, we just started talking naturally as we have been doing for a while now. I noticed some subtle differences though like her playing with her hair, licking her lips more often and our conversation became more personal than normal for us. As we talked, she slowly got closer and closer to me. As we were wrapping up our conversation, I was packing up my bag to leave when she took a chance and leaned in to kiss me. I was surprised for sure, and very hesitant, but it felt so wonderful at the same time.

Slowly my lips parted and accepted her kiss, desiring more. The kiss started so timid as she was obviously nervous about initiating it. As I accepted it though, the kiss grew in need for both of us, the kiss became much more passionate, and I gently probed her lips with my tongue which she eagerly accepted. Her own tongue started to play with mine, flicking over each other. We continued to kiss, the passion building by the moment.

She wrapped her hands around my body pulling me closer as we made out. My hands were in her hair and on her back, doing the same. After a few moments we broke apart for a moment to catch our breath. I looked into her eyes and saw her desire, mirroring my own. I leaned back in to continue the kiss, and moved my hands to her ass, lifting and squeezing it, pulling her closer to me as I did so, my hardening cock pressed against her.

My lips moved to her neck as my hands massaged her ass. Her body responded, arching her back, driving her crotch into mine harder, making me want her even more. My hand moved up to her shirt, grabbing the bottom of it I pulled it over her head, exposing her silky bra over her tight breasts. My hands moved to her back and unclasped her bra. She let it fall off her, exposing her young breasts. They barely moved when freed from the bra, staying upright with tight hard nipples protruding from them.

I leaned down and took a tentative lick of her breast, making sure my tongue flicked her nipple, feeling the stiffness of it with my tongue. I could hear her breath catch as I did this. I moved my hands to her tits and I started licking and sucking on her nipples, drawing them into my mouth and lightly nibbling on them to make them even harder. After I spent a few minutes on her tits, I grabbed her ass and lifted her, kissing her at the same time and put her down on the table we were just using to study on. I laid her back, pulling her shorts and panties off as I did so, exposing her beautiful pussy.

She had shaved bald recently and was open and wet. She was lying there on the table, arms up over her head, legs spread, waiting for me. I got a devilish smirk on my face and moved my face down to her pussy to taste her. I didn't waste any time, diving right in, tasting her for the first time. My tongue plunged into her wetness, savoring the taste, licking in her pussy. I moved my tongue up to her clit and slowly licked it, trying to be gentle to not make her jump too much. I flicked her clit with my tongue, and surrounded it with my lips, gently sucking it into my mouth. As I did this, I slid a finger into her pussy, pushing it all the way in slowly, feeling your body respond against my face and hand. While I slid my finger in and out of her pussy, I massaged her clit with my tongue. I picked up the pace while sliding a second finger into her pussy and continued to lick her clit. I heard her breathing pickup and her body responding and undulating on the table. After a couple of minutes of this I felt her legs clamp down on my head as she orgasmed for the first time with me. Her pussy clamped down on my fingers when she came and became very wet. I pulled my fingers from her now sopping pussy and replaced them with my tongue to taste her even more. She tasted amazing.

I reluctantly pulled my face from her pussy and shed my clothes quickly. My hard cock protruded in front of me, it seemed to lead the way to her pussy. Her legs were bent at the knees and spread to give better access to her pussy. I took her legs, holding her open and slowly pushed my cock into her pussy. I could feel how tight she was around me, squeezing my cock. I started to slide my cock in and out, trying to go as slowly as I could. Her pussy was so tight around my cock, I was sure it wouldn't take me long to cum and wanted to ensure I prolonged this fuck as long as I could. She felt amazing on my cock.

I was sliding my cock in and out of her driving her passion up as well. She was moaning with each thrust, her hands played with her tits as I fucked her. I slowly began to speed up and started to fuck her with more and more force. Eventually I was slamming into her. My balls were slapping against her with each thrust, pounding into her harder and harder with each thrust. I could tell she was close to cumming again and I wasn't far away myself.

I kept fucking her and started tweaking her clit with my thumb while I did so. This sent her over the edge, cumming extremely hard this time, clamping down on cock in the process. I continued to fuck her for a couple of seconds before this sensation took me over the edge as well, making me cum deep inside of her. We just stayed in that position for a minute or two, sweating and breathing heavily. Finally, my cock was limp inside her, I pulled out and a small amount of cum spilled out with me. She sighed as I pulled out as if the void was new to her without me in her.

I pulled her up to me, her face shined with her exertion and her expression was of pure satisfaction. I kissed her for a few minutes, loving the taste of her lips and letting her taste herself on my lips. We started to get dressed, knowing we had pressed our luck on time we had available before her mom showed back up, or worse yet, her dad.

We chatted for a few minutes and decided it was best if I left. We said our goodbyes, and I gave her another long kiss. To my knowledge her parents never got wind of what transpired between us, but unfortunately, we never got a chance for a repeat on any future sessions.