Night Tutor

During college, I tutored high school students for a few extra dollars. The subject I always excelled in was math, for some reason, it just came easy to me. It all started by accident really.

A couple summers before I had worked with a small construction company who needed a "grunt" while building a customhouse. The owner of the company, Robert, was a real nice guy and we became good friends. I continued to work for him every break I had from school and helped him build his own 3 story Victorian home. Shortly after moving in, his wife decided she wanted to leave and took his teenage daughter and son to live in a small house a couple of miles away. Robert was left with a huge empty house that was only occupied by his c***dren a few days a week.

Since I had recently moved out of an apartment I shared with my girlfriend, Robert asked if I would like to rent out the top of the house. I jumped at the chance, and moved in immediately. The top of the house was the very cool. It was a bedroom, bathroom with shower, huge closets, and a studying area. He had designed it for his daughter to have her privacy when she began her college classes. But for now, she was mommy's girl and still in high school. Lucky for me!

The house was a great place to bring women home to. The girls just loved it! On more than a couple occasions, we would have a huge breakfast together with our dates from the night before. Even though Robert was about 15 years older than I was, he still could bring home the young college babes. Sometimes we would hook each other up with friends of the girl we were with. It was like an endless supply of fun. Life was good!

One day, Robert's eighteen year old daughter Jaime was spending the weekend, and she asked me if I knew anything about algebra. Since I did, I sat down with her and helped her finish her homework. She mentioned that her teacher does not really explain it very well and can be mean if she asked too many questions. I assured her that if she ever needed any more help, I would be here. She smiled, gave me a big hug and said "thanks".

For the next few weeks after that day, Jaime asked for help several times. She would come over and we would sit at the dining room table, or on the couch and work on her algebra. She seemed very determined to get her grade up from her dismal "C minus". Finally, she did. She stormed in surprising me with a huge hug and her progress report with a big fat "B". She also said that she had a few friends who needed help. It was then that I realized I could actually be a tutor and make a little money. From then on I tutored 3 or 4 students a week making about $100 for just a few hours of my time. Easy money.

Then spring arrived. The cold winter months filled with snow and ice disappeared, giving way for the suns warm rays. With the warm days, brought problems. Some of the students I tutored where boys, but many were girls. Young, attractive girls who dressed for the weather. Gone were the thick sweaters and pants, replaced by short skirts and thin, tight revealing blouses. I was suddenly aware of how close the girls would sit next to me, the hugs, the sweet smiles and playful laughter. Not wanting to cross that line, I began counting down the days until the end of the semester.

Spring break arrived and a week of no tutoring for me. Robert's wife took their son on a camping trip, but Jaime did not want to go and stayed with us. Jaime had become almost like a little s****r to me and she often teased me about the other girls that I tutored, especially a hot little coed named Monica. Jaime herself was beautiful. Long brown hair, greenish blue eyes, pouty little smile and a body sculpted by many years of ballet. Monica however was pure sexkitten! Jet black hair spiraling down to the middle of her back, huge breasts that defied gravity, tiny waist, tight ass and always dressed to impress. She was dangerous for any man, any age.

I wasn't able to afford a big trip out of town like many of the others at the University, so the local pub was quiet, so was the nightclub, and even the hideaway bars. I returned home one night after playing some pool and drinking many beers to a dark house. Robert and his daughter must already be sl**ping I thought, and I walked as quietly as I could up the stairs to my room. I quickly stripped and fell into a d***ken slumber.

My dreams were crazy. First I am playing pool with Tom Cruise and Paul Newman, and then I am chased by a bunch of zombies that said I cheated at playing pool. Non-stop wackiness. Suddenly my dreams turned erotic. I felt myself floating in water watching naked girls splash all around me. My cock felt hard and I wanted to cum. I could feel the tickle of the waves on my dick and it was driving me insane. Feeling my hips thrusting upward, I woke myself up. My eyes focused on the ceiling above me and adjusted to the dim light of the street lamp peeking in the window. Funny thing was, I still felt the water on my genitals.

Of course, there was no water. Instead, looking up at me with my cock sliding in and out of her mouth was Jaime. I was stunned, not exactly sure of what to do. My mind said, "stop", but my lips could not make a sound. I watched in silent ecstasy as she devoured my hard flesh. Her hand gripped tightly around the base moving with short smooth strokes as her lips slid up and down my thick shaft. I simply could not hold out any longer. My head fell back onto the pillow and a low soft groan escaped my throat. Jaime held tight with her mouth and swallowed.

She continued to suck every drop of come from my pole before releasing her airtight lock. When I opened my eyes, she was standing beside the bed. She knelt down, gave me a quick kiss and left the room. I looked down at my wet limp cock. What the hell was that? Did that really happen? I starred out the window at the street lamp thinking. Finally, my eyes closed and I fell asl**p again.

The next morning I awoke feeling a bit uneasy. Partly from the shots of Jager, but mostly from the visit of Jaime in the middle of the night. She was my good friend's teen daughter and a girl I considered to be like a s****r to me. Last night she acted as neither, and worst of all, I let her. To my defense, she took me in her mouth when I was asl**p and slightly intoxicated. However, I did wake and I did not stop her unbelievable sucking technique. I showered quick and sneaked out the back door with my mountain bike avoid both her and her father.

I spent the entire day away from the house, yet my mind was constantly on her. Those young pouty lips engulfing my cock like no other. I called the house around six o'clock. Robert answered. He said he was just heading out the door taking Jaime out to pizza. Perfect. I could go home, shower and get out before they get back. Which is exactly what I did.

Not really in the mood for serious drinking, I met some friends at the pub for beers and pool. It was a mellow evening and other than my buddy's girlfriend there wasn't a good looking girl in the place. The night ended early and we all went our separate ways. They went to his place to fuck and I went home to think about it. The whole evening I had forgotten about Jaime, but as I pulled into the driveway, it all came back. I quietly stepped up to my room, put on an old Stevie Ray Vaughn CD real low and pulled off my clothes. For a brief moment I wished she would come up again, but a vision of her struggling over a algebra problem with her ponytail falling over her shoulder told me how wrong it was.

I am not sure how long I was out, but the CD had finished and the house was quiet. Quiet enough for me to hear another's breathing. As soon as I heard it, I knew. I opened my eyes towards the ceiling and then glanced downward toward the corner of my bed. There she was, standing naked staring at my own nakedness in the dark. Without a word, she knelt down and grasped my soft fleshy member. I reached out grabbing her arm and sat upward on the bed. "What are you doing," I asked?

"Please, I promise I won't tell anyone," she said. "I have never done this before, and I do not like any boys my age."

Is she telling me the truth? "You have never... you are a virgin? What about last night? Was that your first too?"

"Yes, and it was so great. It was all Monica said it would be, but I think you had more stuff than what she described. I even liked the taste. I didn't think I would."

I was shocked to hear all this from this innocent face. It isn't right, I kept telling myself. However, my dick wasn't listening and grew hard and fat in her hand. I searched my mind for words that I could say to make this girl understand that it could not happen again. Her hand began to slowly stroke my shaft. Her eyes pierced my defenses. I glanced down to her tight beautifully developed body. Her nipples like little erasers pointing towards me, begging for my tongue. She waited for no answer and took me once again in her mouth. That was it.

She slowly sucked and licked from the tip of my penis to soft fur on my balls. She was a natural and so delicate, never scr****g her teeth, never tugging too hard. She was perfect.

With her father downstairs, we were f***ed to be quiet, hence, slow. I pulled off my rod and motioned for her to join me on the bed. She laid down on her back next to me, the streetlight eliminating her smooth skin. When we kissed, it was as two adults who had known one another for years. There was no awkwardness; we both just flowed together. Her tongue gently swirled into my mouth; I could taste my saltiness. Her hands roamed over my skin as did mine on hers. I stroked her shoulders, her firm breasts, her tight young abs and sweet little ass.

I did not wanting to hurry anything, but Jaime had other plans. She f***ed my hand between her thighs upon her soaked sex. I parted the tiny folds with my fingers and caressed her button. She jumped and inhaled a huge amount of air. She quivered as I released her clit and locked her eyes upon mine. Her first orgasm by a man. She wanted more.

She reached behind my back and pulled my body onto her, spreading her legs and fondling my penis. She rubbed her slick pussy with my tip, sending shivers down my legs. She pushed the tip closer to her opening, but was unable to find the gap. I took over and found her small hole, not yet big enough to handle me. I began with the tip, sliding it in and out of her tight rim. Slowly, inch by inch, I pushed forward until about half of my cock was buried in her virgin walls. Her breathing was short and heavy each time I went further inward. I held that position and began pumping half of my cock in at a time in long slow strokes. Her pussy was loosening with the steady f***e and the amount of lube she was making. She began to slide her hips back at my every move, faster and faster. All at once, my entire length shot deep inside her causing her body to shake and her breathing to stop. Her first orgasm with a man inside her.

As she regained her breath, I never let her go of that feeling. I continued to thrust my long shaft into her fresh virgin pussy. Jaime bucked back time after time, faster and faster. Her velvet box gripped my cock each time, sending me closer and closer to my own orgasm. I slid her legs upward and locked each on my shoulder and continued my steady movements. This sent her once again over the edge. Looking down at her mouth, lips open silently gasping for air, her ample firm chest expanding, nipples erect and taunt stomach clenched... I exploded. With one fluid motion, I pulled back my thrust and removed my penis from her sex, sending shot after shot of white cum upon her neck, chest, and abs.

One of the most intense sexual encounters ever. We lay together in pools of our own sweat and orgasmic fluids. The streetlight gleamed on our skin. Our bodies relaxed and fulfilled. Jaime was no longer a virgin. I had lost some morals. We talked about it afterwards, and agreed that it was a perfect night, but one we should never talk about... nor do again.

92% (31/3)
Categories: First TimeTaboo
Posted by shane_orion
2 years ago    Views: 3,493
Comments (6)
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1 year ago
I appreciate the comments. However, the story really is true. And sorry, no, there was no sex with Monica. She came back to my bed a few more times, but I was falling for a co-ed my age and encouraged her to make a fuck friend of her neighbor--she did. She the memory is a good one...
2 years ago
2 years ago
great. Monicas next
2 years ago
great story...witty, sexy, well-written. Keep going, bro.
2 years ago
Very hot story, maybe the next one with Monica?
2 years ago
Very hot indeed,,thanks