Tutoring Adventures

There was a student named Nancy I always had a thing for. She was a petite brunette, shoulder length hair, a little wavy, not perfectly straight. Very cute face, eyes that seemed to have depths, cute little nose and small mouth. Just a very cute face. Her tits were not huge, B cup only, but were very pert and looked good on her figure. Her ass was a tight little thing that also seemed to suit her well. Looking at her you wouldn't think 18, but as a senior in high school and knowing when her birthday was, I knew she was 18.

While her looks were very attractive it was her personality that attracted me even more. She was kind, intelligent, and witty. 3 traits I highly regard. All of these combined with her being a little shy made her very desirable. She also had a boyfriend, seemed like it was steady, but you could tell she was focused more on her schooling than her love life.

I had fantasized about her often but figured there was no real potential. This all changed one evening in late May though. I showed up to our session as per usual at 7 pm. There was nothing unusual about anything at first. We worked through her homework and started to drill down into some problem areas she still had. Around 8 pm when we were wrapping up her demeanor changed slightly and she started to act a little nervous. Seeing this I asked her if she was ok. We had known each other for almost 2 years, tutoring her twice a week since the beginning of her junior year. Now at almost the end of her Senior year we had developed a decent relationship.

She looked at me, and I was a little surprised to see she had tears in her eyes. I asked her what was wrong. She explained to me she was having some problems with her boyfriend. Problems she really didn't want to talk to her mom about. Her dad wasn't in the picture much, and even if he was, she wasn't going to talk to him about this either. Kind of knowing where this was going, I offered to lend her my ear. We moved from the table in the dining room to the couch in the living room at this point to be more comfortable as we talked.

She and her boyfriend had been dating for about 6 months now. To her the relationship was moving at just the right speed. While they had kissed and a little petting, nothing too serious had happened physically. Lately he has been pressuring her to do more. Not necessarily sex she said, but more than making out, more than feeling her through her shirt, more than her feeling him through his pants.

I could tell she was nervous and was actually slightly surprised she was able to even discuss this with me. I told her it was only natural to be a little scared about this. This seemed to ease her anxiety a little and she seemed to relax. She explained she wasn't too worried about her body, she knew she had a nice body, albeit maybe a little small in the chest, but more about her experience. She mentioned she had other boyfriends in the past but had only kissed them, nothing more. The most amount of experience she had was with her current boyfriend.

Again, I explained it is only natural, everyone has to get experience from somewhere. Her boyfriend was much more experienced and was starting to get frustrated with her. While I can understand his frustration, if he really liked her, he could have approached things better. We continued to talk, more to relax her than anything else, at one point she looked at me and got a peculiar look on her face. I asked her what she was thinking. She kind of looked at me again and hesitantly asked if I could do her a favor. A little puzzled, I said sure. At this she seemed to find her courage and asked me flat out if I could teach her.

This caught me completely by surprise. While I had fantasized about this, never in a million years would I have imagined I might actually get a chance. I looked at her and asked her, just to be sure, are you asking me to teach you about sex? She nervously answered yes. I was shocked, but I have to admit, rather excited too. Who wouldn't be if an attractive 18 year old was asking you to teach them about sex. I told her I was a little shocked and why wouldn't she want to be taught by her boyfriend.

She seemed to be ready for this. Her response surprised me a little as it was much more of a grown-up answer. While she liked her boyfriend, she honestly didn't expect it to last much into college or even past the summer. While he was more experienced than her, he still wasn't as experienced as someone older. Someone that clearly had some experience, being married, kids, etc. I thought to myself, of course she would make a very logical decision about this. Her points were well thought out and very valid.

I looked at her, she shyly looked back, a look of hope on her face. I asked, are you sure? She nervously bit her lip, and nodded her head yes. At this I leaned in and we shared our first kiss together. Nothing too crazy yet. This kiss was testing the waters, seeing how much we both wanted this, seeing how eager we were. The kiss started out slow, our lips meeting, lips opening and feeling the heat of each other's breath as we kissed. It only took a few moments before the heat started to rise, the kiss becoming more intense. Hesitantly she started to probe the limits, licking his lips while they kissed. I responded with my own tongue, dancing it along hers. She moaned into my mouth, seemingly eager now that we had started. I continued to probe her mouth with my tongue, one hand was in her hair, pulling her closer, the other wrapped around her back.

I moved my hand down to her ass, squeezing it while we kissed. She seemed to enjoy this very much, moaning into my mouth. We continued like this for a minute until I moved my hand from her hair to her breasts. I started to massage her breasts through her shirt, feeling the resistance of her bra around her breasts. I used my thumb to start to rub where her nipple would be, trying to make it erect before removing her shirt and bra. Her kissing got more insistent with this attention, and within moments I could feel her nipple pushing against my thumb. Switching breasts, I made her other nipple hard as well.

I moved my lips from her mouth to her ear lobe, sucking on it and nibbling. My hand moved up under her shirt, feeling her tits still through her bra. I snaked my other hand behind her, unclasping her bra. Removing this constraint, my hand had much easier access to her breasts. My fingers found her hard nipples easily, rolling them between my fingers, making them even harder. While exploring her chest, my lips were busy kissing her neck as she arched her back. Reaching down I grabbed the bottom of her shirt and pulled it up over her head. I then pulled her bra off gently, fully exposing herself to me. Her small pert breasts are amazing, and just asking to be sucked on. I leaned down, and licked a nipple, making it quiver after my tongue flicked it.

She gasped from the attention, clearly liking it. I pulled a nipple into my mouth, sucking on it gently, flicking it repeatedly with my tongue. She was definitely enjoying this, her breaths were shallower and she moaned often. I used an unoccupied hand to reach down further and cup her pussy through her pants, rubbing her through her pants. She let out a guttural groan with this new assault on her. Taking that as a sign of approval I rubbed her a little more vigorously making her arch her back even further, clearly enjoying everything.

I moved my hand to the clasp of her pants, unclasped them and helped her work them off of her. She sat there in her panties and socks only now. Her panties were a light pink color, with some lacy material. Through these you can see she has left some hair, more trimmed up, than letting it be au naturel. There was also evidence of her arousal from the wet spot on the crotch. The smell of her arousal was intoxicating. I moved my way down her body while pulling her forward on the couch to allow me easier access to her pussy. As my lips finally reached her panties, I licked her through her panties, making sure to press against her clit as I dragged my tongue against her.

This made her buck her hips up, pressing herself against my face harder. I took this opportunity to pull her panties off of her as her ass was already off the couch. Fully exposing her pussy to me, I leaned in to lick her from stem to stern, making sure to flick her clit at the end. She arched her back again, gripping the edge of the couch. I leaned in again, this time swirling my tongue in her vagina, making sure to push it in her slightly. She groaned with this feeling, her breath quick and shallow, continuing to grip the couch with both hands with her head back and eyes closed. She was clearly enjoying herself.

Pushing my tongue out I pushed it into her, wiggling it when it was pushed in as far as I could. I used my right hand to find her clit with my thumb and softly rubbed it with my thumb while I fucked her with my tongue. This seemed to put her on a new level of pleasure, moving a hand from the couch to the back of my head, trying to pull me in further, holding me there. Sliding my tongue in and out of her, I could feel her excitement building more and more as I continued my double assault of her vagina and clit. Rubbing her clit a little more aggressively while I tongue fucker her, she had her first orgasm, gasping and groaning as her pussy exploded onto my face.

I stopped pleasuring her as she came, letting her ride her orgasm out without exhausting her and making her hypersensitive. When she came down from her high, she looked at me with a slightly dazed expression and told me that was the first time she had cum from anything but her own fingers. I moved up and kissed her again, taking it slow and deep. Probing her mouth with my tongue, letting her taste her own juices on my face. After a few minutes of this she pushed me away and then onto my butt on the couch.

She stood up and took my shirt off, pulling it over my head with a smirk but still a slightly unsure look on her face. She was determined though, and pushed through her hesitance. After my shirt was off, she leaned in and kissed me again, reaching down with her hands to undo my belt and pants. I lifted myself from the couch to assist her removing my pants. Once my pants were off, my arousal was very evident, tenting my boxer briefs with my erection. She had a little bit of a glazed look on her face as she looked at my crotch. I told her she can take my underwear off too and gave me a slightly scared but excited look. In the end she reached out and pulled them down, freeing my erection for her to see.

She just looked at it, a little shocked and amazed. I asked her if this was her first cock she had seen in person. She meekly nodded her head. I then asked her if this was the first she had seen ever? She said she had seen some in the few porn scenes she had watched, but seeing it in person was completely different. Now I know I am not huge, about 6.5 inches or so and can just barely get my hand around it all, but I know I am not tiny.

She kneeled down in front of me, inspecting me closer, not really sure what to do so I asked her if she wanted to touch it. Timidly she said she did and reached out with her petit hand to touch my now fully erect cock. My cock kind of jumped at her first touch, scaring her. I told her not to worry, I was just very sensitive and excited. She proceeded to wrap her small hand around my cock, pulling it into a standing position and slowly pumping her hand up and down on my hard shaft. I put my head back, closing my eyes to fully appreciate this sensation.

She started out slowly at first, a little unsure of herself, but after a few moments seemed to get the hang of it and started to stroke me with more confidence. Her hand would move down to my base and all the way up to my head, sliding her smooth hand across me, making me feel amazing. She started to increase her tempo, sliding her hand a little more aggressively, adding a lot of friction to her stroking. I suggested using some spit to lubricate her hand as she stroked me. She looked a little unsure but licked her hand and tried again. With her hand more slippery now, she was able to stroke me faster, making me moan with appreciation. She started to realize when her hand was too dry and would pause to lick her hand again and resume her stroking.

After a few minutes of this she got brave enough to spit on my cock as she was stroking me. She started to really get into it, stroking me faster and faster, making me moan more often with pleasure. As she noticed some precum on my head she asked what it was. I told her and she was intrigued, but didn't want to taste it. She ran her hand over it, using it to further lubricate her hand, driving me closer and closer to cum. It told her I was getting close to cumming and asked her to keep going. She responded with eagerness, sliding her hand faster on my cock, driving me even closer to cumming. As she continued stroking me, I couldn't hold it any longer, it felt as if I was on the edge for so long, and I came hard. I seemed to erupt in her hand, spurting stream after stream of cum onto my chest and stomach. Her hand continued to stroke me while I came, not knowing what else to do, getting covered in my cum and adding to the heat and lubrication of my cock as she worked me up and down.

After I finished, I had to make her stop as I was too sensitive for her to continue to stroke. I took her hand in mine and pulled it off of my cock. I was completely spent, I don't think I could cum again that night if I wanted to. My cock continued to spasm after my orgasm while it began to soften. She looked at it in a kind of awe, not realizing how much of a mess it could make. We then realized how close we had been to destroying her mom's couch. She asked me if I always cum that much. I told her no, not typically that much, she had just gotten me very excited. She seemed pleased with this answer. She leaned in and kissed me with a long and lingering kiss. After a minute I excused myself to the bathroom with my clothes to get cleaned up and dressed before her mom got home. When I got out, she had dressed herself too, and managed to look respectable, although you couldn't disguise the glow on her face.

I came over to her and kissed her again, more than a peck, but much less than starting another make out session. I told her next time I get to focus more on her, which she readily agreed to. Only a few minutes later we heard her mom pull in the driveway. With both of us presentable we didn't worry too much at this point. We both sat down at the table again and pretended to wrap up our tutoring session as her mom walked in the door. We set up a time for the following Tuesday and I made my way home thoroughly satisfied, and prayed my wife wouldn't want to have sex tonight.

The weekend went by way too slow as I knew next Tuesday would bring even more fun with Nancy. I actually did manage to get things done around the house over the weekend and didn't make any additional work for myself because I was distracted. When Tuesday finally arrived, I left as usual, hoping my excitement wasn't overly obvious. I may have spent a little more time getting ready than usual. Making sure I was clean shaven, smelled decent, etc. Not that I didn't do that normally, just spent more time than normal for a tutoring session. Probably dressed a little nicer than normally as well.

When I got to Nancy's house, I found she had put the same amount of effort into herself. She was wearing a very cute, tight shirt, shorts that seemed to be painted on, sandals and I realized, no bra. The nipples were already hard, pointing against her shirt. She had some makeup on as well, accentuating her beauty.

She let me in with a rush of excitement. The excitement was palpable. I found myself getting more excited, just being in her presence. Once I was in and she shut the door behind me I found she hadn't even pretended to get things out to study with today. I smirked knowing I probably would have been pretty useless if she did really need any assistance today. I turned around from looking at the table to find her very close to me, looking at me with longing in her eyes, biting her bottom lip.

I pulled her to me, squeezing her body against mine and leaned down to kiss her. Our lips met, much less timid than last week. We seemed to pick up right where we left off. Her lips parted immediately, accepting my tongue into her mouth. The kiss quickly grew in intensity and our hands could no longer remain stationary on each other. My hands quickly worked their way down to her ass, lifting her up to kiss her better. In response she wrapped her legs around me, as her hands were both on the back of my head, pulling me in closer for kisses.

We kissed like this for a minute or so and even though she was petite, and supporting herself, she tended to get heavy! I wasted no time and carried her down to the bedrooms. I let her direct me to the first door on the right. She reached back and opened the door for us. I walked into her room viewing it for the first time to find a neat and organized room that wasn't too girly, but obviously had some female touches to it. I laid her back onto her full bed, and followed her on the bed, where she found me on top of her, her legs still wrapped around me, holding me there.

We kissed passionately like this for a moment until I slowly pulled away. She kind of got a sad look on her face while also a longing expression. I understood... she didn't want to stop kissing, but longed for what would come soon. As I separated myself from her, I reached down and pulled her shirt off of her, or rather peeled it off of her it was so tight. When it was finally removed, her tits were free to explore with my mouth and hands. I leaned down sucking on one nipple, nibbling it between my teeth as I my other hand pinched gently and pulled at the other nipple.

She was squirming under me now, her hands seemed to be everywhere. Roving from my hair, to my back, to cupping her own tits for me to access better. I switched tits with my mouth after a few minutes, wanting to make sure I split my attention between the 2 of them. When I finished, I had both of her nipples so hard it must have been slightly uncomfortable. I reached down, unbuttoned her shorts and pulled them off of her. Today she had on some white panties, nothing too crazy, but definitely sexy with the cut, tapering way down, just shy of a G string.

I could smell her arousal again, and see the evidence. She definitely got wet when she was excited. I got a smile on my face as I lowered myself between her thighs, inhaling her arousal more closely now. I was getting uncomfortably hard in my pants now as well. I stopped and removed my clothing, while she watched me with excitement visible in her eyes. Once I was free of all my clothes, I kneeled down between her legs again and pulled her panties to the side so I could more easily access her pussy.

I used my thumb to rub her clit as I started to explore her with my tongue. I snaked my tongue around her entire pussy teasing her. Eventually I worked my tongue in towards her opening and parted her with it as I pushed it into her. I heard her gasp at the intrusion and applied more pressure to her clit with my thumb and rubbed more vigorously. She groaned in delight as I continued to probe her and rub her clit. After a few minutes I switched my hand and mouth and slowly slid in 2 fingers deep inside her as my tongue concentrated on her clit. I could now feel a new urgency with her as she started to respond more and more to my attention.

She started to buck her hips up and out into my hand as I fucked her with my fingers. I could feel her pussy start to clamp down on my fingers as they pounded into her. After a minute of this she lifted her hips off the bed and groaned as her pussy seemed to grip my fingers with a hand and pulsate on them. I left my hand stationary and let her ride her orgasm out, bucking her hips and groaning in delight.