Tutoring Adventures

There was a student I tutored for a few years a while ago, her name was Yume. I started tutoring her during her Sophomore year in Geometry. She was a very good student, and she probably would have been fine without me, but her parents were pretty strict, especially her mom, and wanted to ensure she got the best grades she could.

A little about me if you haven't read any of my other adventures. I am an engineer by job, working as a part time tutor as well, married and kids, although a significant lack of passion in our relationship.

Yume's family dynamics were interesting. From Japanese descent, her parents were both 1st generation born in the United States and seemed to follow many traditional Japanese customs, but I will be the first to admit that I don't know a lot about them. I am only speaking from perception, not knowledge. Yume was caught in the middle between their world and her world as a teen growing up in the US.

I made sure to treat her parents with extreme respect but her mom always watched me like a hawk. That first year of tutoring had to be more stressful for her than Yume. Yume was a good kid, with a good head on her shoulders. What I couldn't figure out is if her mom didn't trust her or me.

As time went on, her mom did seem to get more comfortable. Her Junior year progressed through Algebra 2 and I continued to tutor her once or twice a week. I watched as Yume matured and developed into a gorgeous young woman with a very athletic figure. She did have a boyfriend throughout this year and perhaps her mom saved her energy to watch over them more than me, I don't know. By her senior year she had fully developed. She was an independent young woman of stunning beauty. Her long dark hair contrasted with her exotic green eyes. She still had her athletically trim body, about 5'6" and small tits. She portrayed herself with confidence too, it was very nice to see.

Throughout her senior year we seemed to get more and more freedom during our tutoring sessions. While last year her mom didn't watch us like a hawk, she was still around. This year it seemed she had changed a bit. Maybe deciding that as she had a boyfriend, I was probably safe, and also perhaps she was just comfortable with me being around. Either way it just tended to work to our benefit.

Later in the school year, we were kind of alone for one of our sessions. Her mom was home, but in a different room. We were studying as normal, she was doing some practice tests and needed to spread out some more. This was usual and as I had become very adept at reading upside down I sat opposite her at the table, watching her work. I do have to admit though, this seat definitely had some major advantages over sitting next to a student. With the right shirt, it could give me quite a show. Some of my students have realized this and purposefully teased me, others seemed quite oblivious to this.

It seemed at first that Yume had no idea she was teasing me. Granted, with her small tits, and there wasn't much cleavage, but there was enough to catch my attention. On this day she wore a loose fitting tank top with thin straps covered over with a loose fitting button up that was mainly just covering her arms. As she was concentrating she had a very enduring habit of biting on her lip to the side. I found myself focusing on her lips several times during the evening without realizing it. I managed to catch myself everytime without her noticing, or at least I thought I had. As the evening progressed, she got more and more comfortable, at one point sitting with her legs tucked under her, propping herself up more than usual.

As she continued to concentrate, and in her new vantage point, she was leaning over her work more than usual. At one point I looked up from her work and noticed I could look directly down her shirt. Her over shirt was open completely, allowing her tank top to drape down, allowing me a direct view of her tits. I know she rarely wore a bra as her tits were pretty small, and tonight I was glad of that. As I glanced, I could have sworn her nipples were hard. Now granted, I had never seen her nipples before, but I am sure, if this was their natural state, I would have seen evidence through her shirts' before today. I was captivated. As my focus was on her tits, it took me a second to realize she had stopped writing. Knowing I was probably in trouble I slowly let my eyes wander up to her face. She was looking directly at me, a smirk on her face, slightly sucking on the eraser on her pencil. I am sure my face must have turned beet red at this point as she laughed out loud at me. I tried to stammer out an apology but probably just made everything worse.

By this time I was also sporting a very hard erection in my shorts. As I have said before, tits are my weakness, large or small, doesn't matter. She must have had an inkling of what I was going through as she smiled broadly at me, but didn't say a word. She gave me a knowing smile and went back to work, getting more comfortable again, pulling her feet out from under her. I might have been sweating a little and was slightly devastated that she caught me. A moment later her mom came out and seeing my face asked if I needed some water, Yume covered up a laugh while I answered that would be great.

A moment later she came back with the water and went back to whatever she was doing. I figured I was in the clear at this point and started to get back to work. A moment later I felt her foot in my crotch and whatever control I had managed to get, I lost that instant. She started to slide her foot up and down my now completely hard cock. I looked across the table at her to find her staring at me, concentrating on what she was doing. I sat there, a bit dumbfounded to be honest, completely unprepared for this. It had honestly been several days since I had any action, by myself or with my wife, so I was beyond ready at this point. She deftly stroked me with her foot, seeming to flex her toes to grip me somehow. I could do nothing but sit there as she stroked me, partly out of shock, partly just enjoying the feeling of it. My face must have been amusing because she started to laugh out loud watching me. I was concentrating hard on enjoying the circumstances that I was pretty oblivious to everything else, I am lucky her mom didn't come around at that time.

She got serious then and started to stroke me faster with her foot, applying a little more pressure while biting her bottom lip. She was staring at me intently, her eyes seemingly on fire with desire and her foot expertly stroked me. I was already getting close to cumming, which surprised me. Not that I have a ton of stamina, but typically much more than this. I didn't dare make my enjoyment too obvious but she could tell I had to be close. She continued stroking me until I couldn't take it anymore, I kind of grunted as quietly as I could as I proceeded to fill my pants with cum. It was at this point I was very glad I was wearing boxer briefs, had I been wearing boxers I am sure my cum would have run down my leg. As it is, I am sure that given enough time the front of my shorts would be obviously wet.

As I calmed down, she casually withdrew her foot from my crotch, still with that evil grin on her face. I calmly excused myself to the bathroom, making her laugh. I had to admit, it was kind of funny. I got to the bathroom and locked myself in. I proceeded to clean myself up as much as I could, although I had seriously made a mess. I atleast made myself comfortable enough to finish our session and made my way back to her. I sat back down and we finished the session with only a minimum amount of awkwardness. As we finished we scheduled the next session as if she hadn't just made me cum in my shorts with just her foot. I shook my head as I walked to my car and drove home.

The next few days were uneventful, I didn't receive any texts from Yume or her mom, not that I really expected to. It was then the day before our next scheduled appointment and I got a text from Yume rescheduling our session out 1 further day. This wasn't common with her, but didn't really make me wonder why. It does happen with students and typically I am flexible enough to handle these late requests.

The day came and I showed up as usual at her place. I was let in with all the usual courtesy, slipped my shoes off and made my way to the usual table. Sitting down next to each other we got started with perhaps the only awkwardness in my head. She was her typical jovial self and her mom seemed talkative than usual as well. About 10 mins or so into the session her mom announced she had an appointment she had to go to, and would be gone at least an hour. With this announcement ideas started to trickle into my head, or maybe pour is a better term at this point. It wasn't 2 minutes after her mom drove off that Yume stopped what she was doing and got up. She pulled my chair away from the table and proceeded to straddle me, sitting on my lap and leaned in to kiss me.

We kissed for a couple of minutes, both of us savoring our first kiss, seemingly a little out of order after last week's footjob. Her lips felt soft but firm at the same time, forceful at one point and yielding the next. We explored each other's mouths with our tongues, while we wrapped our hands around each other, pulling each other even closer.

As we kissed she was grinding herself against me, the rubbing was driving me a little nuts, but thankfully I was going to have more stamina today than last week. I finally stood up, bringing her with me. She wrapped her legs around me and held on with her hands as we continued to kiss. I carefully walked down the hallway, choosing a door at random and plopped her down on the bed.

As she landed she pulled her shirt over her head, while I pulled her shorts and panties off. She laid there, fully exposed to me, her pert A cup breasts for me to devour, hard nipples and all, and a perfectly shaved pussy for my inspection as well. She was looking at me with a hungry expression that I am sure my face mirrored. I quickly removed my own clothes at this point as well. Pulling my shirt up and over my head and my shorts and boxer briefs down together. My cock sprang free, seemingly glad to escape the restrictions of my underwear.

I climbed up onto her, hovering over her and kissed her again. This kiss was on another level from the previous, it was very deep and searching for lack of a better word. My hands found her tits and nipples while we continued to kissed. I pinched and pulled on her nipples until they were hard as rocks in my hands. I slowly moved my mouth from hers and found my way down to her tits. I made sure to leave lots of wet kisses all over her chest, everywhere except her nipples. Purposefully missing those sensitive spots making the anticipation drive her nuts. After what must have felt like an eternity I let my tongue reach out and flick her left nipple. She gasped with the attention and arched her back trying to force more contact. I snaked my tongue around that nipple, twirling it. She tried forcing my head down with her hands, wrapping them around the back of my head. Resisting her attempts I continued at my own torturous pace. I moved in closer eventually and sucked her nipple into my mouth, feeling the hardness on my lips and repeatedly flicked my tongue over her nipple.

After a minute of this I moved my mouth to her right nipple and repeated my actions on it. When I was done, her nipples were so hard they had to be painful. She was sweating and gasping for breath, obviously very excited, but hadn't cum yet. I didn't think she would from that, but it wouldn't have been the first time I had witnessed a woman cum from just playing with her tits if she had. I then pulled my mouth away from her nipple and slowly kissed a trail down her body until I reached her pussy. I had been waiting for this since last week. I used a hand to rub her pussy, making sure to dip my fingers inside briefly to get my fingers well lubricated with her wetness. Doing this I started to rub her entire pussy. Dipping in often to relubricate them and then moving them back up to her clit, giving her the necessary friction to really get her excited.

I continued this for a couple of minutes, sliding my fingers roughly over her clit and snaking them inside her on the downward stroke, to only pull them back out and over her clit again. She was grunting loudly at this point, gripping the comforter tightly with her hands as I continued to rub her. I finally leaned down and licked her clit when she wasn't expecting it. It was like I flipped a switch on her and she came instantly. Her pussy seemed to explode on my hand and face, and her groans got much louder. After a moment she calmed down and looked at me with an expression of wonder and hunger.

I didn't waste anymore time and dove into her pussy with my entire face. I pushed my tongue into her as far as i could. I proceeded to slide my tongue in and out of her while my right thumb started to rub her clit. This started the cycle over again, with her rocking her hips on the bed and grabbing my head pulling it in tight against her. I didn't resist this time, but let her do it. With my head trapped and my thumb repeatedly rubbing her clit I started to feel her excitement building again. I continued like this until I felt certain she was getting close to cumming. I pulled away to her disappointment, but quickly replaced my tongue with two fingers I pushed directly into her. At the same time I assaulted her clit with my tongue. I wasn't gentle, I lashed her clit with my tongue, wiggling it around it, swirling my tongue around it too. Finally I leaned further in and sucked her clit in between my lips. She kind of yelped in surprise as my fingers also plowed into her again. As my fingers probed her depths, I curled them upwards, aiming for her g-spot.

Whether I hit it or not I don't know, all I know is that she came at that point. I could feel her pussy pulsating around my fingers, squeezing them tight. I paused for a moment, letting her ride her orgasm out. As she calmed down she looked at me while I started to fuck her once again with my fingers. She laid back and just accepted my attention to her. I continued to slide my fingers in and out and started to rub my other thumb on her clit. I looked up at here while I fucked her with my fingers, I watched her as she surrendered to my touch. As I fucked her with my fingers, with each thrust in, she would tip her head back and open her mouth. As I picked up the pace, her head remained in a tipped back position, her lips were parted and she was grunting with every thrust.

After a few minutes of this, I was finger fucking her very fast and her grunts had turned to moans. I wanted to make her cum one more time before I fucked her so I continued to fuck her with my fingers. I continued thrusting them deep inside her but momentarily withdrew my thumb from her clit, only to replace it with my tongue. I wiggled my tongue around on her clit while my fingers probed her depths, trying to make her cum. Finally I detected a change in her moaning, a slight sense of desperation. I picked up the pace one final time and it took only a moment for Yume to reach another orgasm. I paused my thrusting and removed my tongue from her clit letting her ride her orgasm out. I waited as her body seemed to spasm and she grunted with each wave of pleasure. Finally she calmed down, her breathing finally returned to normal and she opened her eyes and looked at me.

Her eyes were filled with desire, pleasure, wonder and contentment. I crawled up her body to find her lips. We shared another deep kiss, our tongues darting into each other's mouth, probing each other's depth. I am absolutely sure she could taste herself on me as my face had to be covered with her juices. This didn't deter her though, she kissed me just as hungrily as before. As we continued kissing, she put her hands in my hair, pulling me closer, my hands supporting me more than anything so I didn't crush her.

I moved one of my hands down and attempted to position my cock at her pussy to start fucking her. She stopped kissing at once and told me no and to lay down. I obviously complied, waiting for her to do what she wished. As I laid there, she got on all fours over me, and leaned down to kiss me one more time, this time just as a tease more than anything. She broke the kiss after only a moment and slowly moved down my body, licking my nipples and planting kisses all the way down to my cock. When she got there she gave it a proper inspection for the first time and smiled. She noticed my cock head was already wet with precum and quickly licked that up. I sucked in my breath through my teeth at the unexpected contact. I heard her giggle at this and then proceeded to take me completely in her mouth without any other warning.

I groaned with pleasure as she started to bob her head up and down on my cock. I told her to go easy otherwise I would end up cumming in her mouth, ruining the main attraction for the day. She got the point and seemed to ease up a little bit, but still enjoyed pleasuring me. She stopped after a couple of minutes, enough to ensure I was rock hard, but not enough to make me cum.

I went to push her off of me and she shook her head no again and started to climb on me, straddling me. She leaned down and we kissed again, a long savory kiss with lots of tongue. After a minute she sat up, and lifted her ass off me. She reached down, grasping my cock and positioned it at her pussy and slowly sat down on me, sliding my cock deep within her. Pausing for a moment to get accustomed to me, she started to slide up and down on me, revelling in the feeling and the control. As she continued she started to pick up the pace. Her ass started to bob up and down on me, her tits giggled a little as she fucked me and her hair cascaded down around her face.

Her groaning was rising in intensity, her thrusts were harder as well. I started to meet her thrusts with upward ones of my own. She groaned even louder with this and I could feel her pussy starting to constrict on my cock. We continued to fuck like this for another minute until I felt her pussy clamp down on me. Her orgasm hit her hard. She groaned loudly as she rode out her orgasm, her pussy convulsing on my cock, seeming to spasm.

I sat still as she came down from her high. When it finally subsided she looked at me with a little bit of a sheepish grin and leaned down and kissed me again. I took this opportunity and flipped us over. She squealed in laughter for a moment before I started to thrust into her. She tipped her head back as I started to fuck her. Her legs spread wide and wrapped around me, encouraging me to fuck her deep. I leaned down and kissed her deep as I continued to fuck her. My hips thrusting down and in continuously, my cock buried deep inside of her.

After a couple minutes of this I stopped and positioned myself on my knees between her legs, her legs over my shoulders, my cock positioned at her pussy again. I slid in slowly, loving that feeling. Once I was fully in, I didn't waste any more time and started to fuck her hard. I started to piston in and out, loving the way our bodies slapped against each other, loving how my balls would slap her too with every thrust in. I kept this up for a while, slamming into her, both of our arousal levels increasing with each stroke.

I wanted to prolong everything but was failing miserably. I could feel my orgasm rapidly approaching and hoped she was close too. I could feel her pussy tightening up around me again, a good sign. As I continued to fuck her, her pussy was tightening even more around me, increasing both of our pleasure. The friction was amazing, sending me to a new high. I continued to thrust in and out, picking up the pace with each thrust. Soon I was fucking hard, slamming in and out.