Crossing the Line

I was nervous already. This was definitely questionable. She was my student and I shouldn’t have offered her a ride.

She came from a broken family, and had developed a bit of a fixation on me and I knew it. Of course her fixation was probably more of a father figure thing, but she clung to me like my approval meant life or death for her. She had no real role models and was living with her grandmother who always criticized her. Apparently her real father had never shown her much affection and her mother had died when she was young. When her left the country for his company he sent her to live with her grandmother, and she had all kinds of issues.

Today was only a half day, which gave the students the rest of the day off. She had stayed after school to help with a project and the two of us ended up working alone for an hour. I didn’t really need her help, but she wanted to help so I let her. As we were alone together for awhile, I couldn’t help but notice how nice her figure was filling in. She was a petite girl, but her hips were shaping nicely, and her small breasts were quite shapely. If she hadn’t had the glasses and her hair tied up, she actually could have been quite hot, particularly if she had worn make-up. I knew I shouldn’t have been looking at her like that, but I just kept catching myself doing it. She just seemed to be thrilled to be spending time alone with me, even if it was helping with an event I was putting together. I could tell she was fantasizing maybe that this was some sort of date between her and I, and should have probably gotten out of there asap, but I was thinking about....well things I shouldn’t have been thinking about with a student. Instead of ending the awkward situation, I allowed it to continue.

As we left, I walked to my car and she followed. I should have used my head, should have said goodbye there and got into my car, but stupidly, I offered her a ride. As we drove I said I needed to drop some stuff off at my place before I dropped her off. I could have driven her home, but deep down I was playing a risky game. Deep down I wanted to take her home. I told myself I would just drop the stuff off and then drive her home, but the reality is that I could have just driven her home first.

As we pulled in to my driveway, I got out of the car and while I could have taken it all in myself, I asked her to help me carry the stuff in. Stupid. I was risking my career, and all kinds of trouble. I looked around, hoping that none of my neighbours saw me going into my place with a student. As we walked in, I had her help me carry the stuff into the basement. I think we could both feel the tension and awkwardness, but the fact was she was a student who trusted me, and that really put me in a position of advantage. As we put the stuff down I saw her stretching her neck, as though it was stiff. Almost as though I was on autopilot, I reached out.

“Hey, little sore there?”, as my hand touched her neck, and started rubbing gently as she reacted awkwardly, blushing yet turning so I could rub her neck. This was so wrong, I was already crossing a huge line, and every bit of common sense was screaming at me to stop and get her home, but I wasn’t listening. I felt.......driven, as I moved in close behind her, and rubbed her neck, and her shoulders, making small talk;

“You’re all tense; let’s see if we can work that out”

It was a pointless statement. The sexual tension in the room was literally vibrating. She was trembling, whether from excitement or fear...or both, she was shaking. My hand moved over her back, and started rubbing it as we stood there, her facing away from me, just accepting the massage from her older teacher. I was not one of the guys at her school; I was a man, and I was touching her like no-one had before. I started to work up her neck, and then made an excuse to let down her hair so I could massage her scalp. I asked her to remove the glasses just so I wouldn’t knock them off by accident. She was facing a mirror, and she looked beautiful with her hair down, and her glasses off. Her figure actually looked quite shapely.

It was not a matter of if at this time...just when. I turned her around to face me, and looked her in the eyes. She knew I was thinking of kissing her, and I could tell she was thinking of me doing that. Then I did it! I gently leaned forward, bringing my mouth towards hers as she looked with nervous excitement and awkwardness at me. Then our lips touched. The line had been crossed. There could be no pretence that this was merely a casual friendly if inappropriate exchange. I was now kissing my student on the lips, and she opened her mouth, allowing me access. I pulled her in close, holding her tight as my tongue probed her mouth. I could feel her heart pounding through her chest. Excitement? Nervousness? Fear of performing poorly due to having never kissed a guy? Fear of where this would go? It was hard to tell, but she was trembling and her heart was pounding as she tried to control her breathing.

I gently took her and lowered her to the floor as she accepted this passively. She had always adored me, and now she was in my basement, laying on the carpeted floor, kissing me. I started to undo her blouse as she lay there awkwardly in her nervousness. Seeing her flat belly, and her soft skin, I needed to remove the bra so as to see her tender mounds. Gently I reached behind her back, and undid the clasp, removing the bra and the shirt. Her upper body was nicely toned in it’s youthfulness. I touched her breast and started teasing it as we kissed. She was nervous and awkward, but she kissed back.

This was just so wrong! So wrong! The trouble I could get into for this was insane, yet here I was acting on autopilot. I was so fucking horny for this young student of mine I was just disregarding the warnings screaming in my head, and kept mauling her flesh, feeling her body up.

I needed to see her whole body naked! Part of me tried to convince myself that I would stop there, but deep down I knew I wouldn’t. I was intoxicated by her youth, her soft tender flesh, her innocence, and the fact that I was committing the ultimate taboo. I reached down to her jeans and undid her button. Then slowly I started undoing her zipper. She was looking up at the ceiling as I did this, nervously breathing rapidly, as I slid the jeans over her hips, and past her panties. Carefully I slid the jeans down her legs, taking them off one leg at a time, and removing her socks.

Now the beautiful young girl was laying on my floor with nothing but a pair of panties on as I admired her slender form. I undid my shirt and then my pants very quickly, leaving my underwear on I gently dropped on top of her, and kissed her some more, grinding my body against hers. Moving between her legs, I pressed my crotch against hers causing her to gasp at the feel. Pressed between her pussy lips and my erection was a thin layer of her panties, and a thin layer of my underwear. My heart was beating fast, as I knew this was a big mistake, but I still had to do it. I was driven by lust for the pretty little angel.
I started moving my mouth past her neck, and over her breasts, moving my way down her abdomen. Gently, I started kissing her flesh over her rib cage, then past her solar plexus as I kissed my way slowly down the young girls body. My kisses moved closer to her abdomen which was fluttering nervously, as I gently kissed and licked around the area. Slowly I moved down to her panties, working my mouth over the panty line as she gasped. I worked my mouth down to the outline of her pussy lips pressing through the material as she gasped even louder.

I needed to get to her pussy now. Grabbing the material, I pulled, gently lifting her butt off the floor as I pulled the panties off of her hips, and then quickly slid them off her legs and threw them aside. They were very plain looking panties, but then I doubt she got up this morning planning on having sex.

She closed her legs, but I gently parted them again, and looked between them at the treasure waiting there. It was so soft and tender looking. Everything you would expect from a young virgins pussy. I pulled my underwear off and moved over her as her eyes widened nervously. I wasn’t going to penetrate her just yet. I wanted to get her more aroused so it would be easier. As we kissed, I moved my hand between her legs and started gently stroking her soft little pussy as I kissed her. Her whole body was trembling, but she wasn’t resisting. This was good. She was afraid, but still willing to. She adored me, and wasn’t going to risk blowing this by acting afraid or asking me to slow down.

I took her hand and guided it to my erection. She looked at it and tentatively allowed her hand to be placed upon it, as I stroked her pussy. The look on her face was a mix of curiosity and fear. She had seen diagrams of the male penis in sex ed, but had never seen one for real, and was both intrigued and intimidated at the same time. She explored it with her hand, fascinated, yet I could see her mind working. She knew where this would be going next and had to be wondering if it would fit. She probably heard various things about first sex, including clinical terms like “hymen” while at the same time hearing slang terms such as “pop her cherry”. She may have heard some of her friends talk about sex, so she was undoubtedly nervous about pain, but at the same time she was still exploring it with intense curiosity.

She was plenty wet at this point, and I couldn’t wait any longer. Rolling completely on top of her, I moved her legs wide apart, and lowered myself between them as she looked up at the ceiling, her big eyes showing her nervousness and innocence. I grasped my manhood, and guided it to her flesh, causing her to gasp lightly as I made contact. She was breathing rapidly, trying to calm herself as she braced herself to be penetrated.

Moving my body foreword, I started pushing against her pussy lips as she tensed up in preparation. I was trying to be gentle, but at the same time, I was excited and wanted to deflower the beautiful young girl. Wiggling my hips, I rotated my cockhead around as I applied pressure, trying to open her up a bit and gain entrance. As I started to open her, and slide my head in, she gasped and then opened her mouth as though to cry out, but remained silent. As I pushed a bit more, sliding the head in, I felt her pussy stretching as my hardness pushed it apart, while she lay there gasping very small breaths, tensing, biting her lip as she tried to be brave about the whole thing. I slid in a bit further, and encountered resistance as her pussy clamped down on my cock head. I paused for a second as she started trying to catch her breath. I was hurting her but her crush on me would not allow her to ruin the moment by screaming or whining. She looked at me and mustered a nervous smile, trying to look like she was enjoying this.

I didn’t enjoy hurting her, but I knew I would eventually have to break through, and the longer I delayed it, the longer she would be in suspense, so I leaned in and applied pressure gently against her hymen. She clamped her mouth shut, breathing in rapidly through her nose as I pushed gently.
It did not yield easily, so I had to push a little harder. Leaning in to her, I pushed a bit harder, slowly increasing the pressure on her cherry as she gritted her teeth, and scrunched her eyes shut for a second, turning her head to one side as her breaths came in small erotic little gasps. I pushed a little harder, and suddenly it gave, tearing under my pressure as I slid several inches in before being stopped hy her tightness as she yelped from the pain, her eyes opening wide as she then opened her mouth wide, but did not scream. She started blinking rapidly, as though trying to prevent water from collecting in the corners of her eyes. She seemed to be trying desperately to control herself and not act like a frightened girl, but I could tell it wasn’t easy for her. Her little pussy was clenching fiercely on the part of my cock that was in her and it was the most delightful sensation. It even seemed to be pulsing, clamping repeatedly as though doing it with her heartbeat.

I needed to get the rest into the beautiful girl, and started working the rest in slowly as she lay beneath me, her legs spread wide, gasping, biting her lip, clenching her teeth, moving her head from side to side, and opening her mouth in little silent gasps as she felt my hardness pushing in deeper, opening her even wider until I got the whole thing in. I paused, because as horny as I was I still didn’t want to inflict more pain on her than was necessary. She was young virgin, very tight and I was reasonably well hung, so naturally this would hurt her, but there was no point in being deliberately cruel about it. I gave her a few seconds to adjust as she lay there beneath me, trying to get her breathing under control.

Pulling back slowly, I pulled almost all out, until only my cock head remained in, and then slowly, I leaned in, and in one slow thrust, pushed the whole thing in slowly as her mouth opened again in a silent gasp, as her innocent eyes betrayed the pain of the experience.

Then I started slowly making love to the little princess on my basement floor. Moving my body foreword and back, I started sliding my cock in and out of her tight grasping pussy. I tried to not go too fast as she was still in some pain, but at the same time, her inner flesh grasping me so tightly had me turned on insanely. I wanted to fuck her little body wildly, but still tried to exercise some constraint. It would hurt her, but if I went completely savage and really hurt her she might tell somebody, so as much as this would not be a physically pleasurable experience for her, I was not going to turn it into torture. That said, after awhile I was getting very excited and couldn’t help speeding up as I fucked the tender virginal beauty beneath me.

I’m not sure how long I fucked the little darling, but I must have gone for awhile, thrusting my hips between her legs as she lay there, biting her lip, gasping lightly, clenching her fists as I drove my hardness into her tight young flesh, pleasuring myself with her young body as she lay there enduring it. As I felt my orgasm coming, I started to speed up, thrusting faster as she clenched her teeth, scrunching her eyes shut and turning her head to one side as I thrust faster into her, driven towards my impending orgasm as my violation of my student started to speed towards climax. A few more thrusts was all it took to push me over the edge as I came with the most powerful orgasm I had experienced in years, my cock flexing inside her tight pussy as I pumped my semen into her body fiercely like a jet pump, as she lay there tensed up in discomfort with my body tensed on top of her until I had pumped all the semen I could into her, and then I relaxed on top of her, catching my breath.

She let out a loud breath of relief, as she looked up at me with her big beautiful eyes, imploring, showing her relief at the end of the ordeal, and her adoration of me as I looked back at her, as my cock softened inside of her. I pulled out as she gasped at the sensation of suddenly being empty. I lay there kissing her as she kissed back, and I held her in my arms.

My orgasm passed, my lust sated, common sense was creeping back in. I had just crossed a huge line. I had sex with a student. I needed to manage this situation carefully. An overt relationship would catch attention, but cutting her of right away might cause her to make a fuss. I needed to find a way to keep her happy, yet keep this discrete.

I convinced her that I had feelings for her, and explained that I really wanted to keep what was between us, but told her that if anyone found out we would be broken apart. She seemed to understand and agreed that we would keep this to ourselves. THANK FUCK!

We talked about ways we could meet discretely in the future. I would try to manage my way out of this gently at a later date but for now I had to keep her happy. She just lost her cherry to me, and suffered some pain in the process. I couldn’t let her feel dumped.

We dressed, and then I drove her home, dropping her off a block away from her home. She seemed to agree that this was sensible and got out, but first she leaned in and gave me a big kiss on the lips.

As I drove away, I pondered how I would manage this situation without losing everything.