Crossing the Line

As a male high school gym teacher I had enjoyed many fantasies about "crossing the line" with one of my hot female students. At just 25 years old and still in ripped shape I often overheard the girls discussing "wanting to fuck Coach Anderson." Hearing this talk just fueled my fantasies even more. However, I was happily married and not near perverted or dumb enough to risk ever trying to act on these fantasies. That all went out the window when I met Jessica.

Jessica wasn't a traditional babe, but she kinda oozed "sexuality." She was pale with long brunette hair. She already hand the curves of a woman on her athletic 5'7 frame. Her tits were full and her ass was round and she was always running afoul of the dress code showing them off.

She was a senior and as mature as most adults. I had went to school with her older sister, who looked a lot like Jessica, and had always wanted to fuck her, but never did. Jessica and I were both free spirits and hit it off from the start. Eventually, conversation evolved into flirting and flirting created a lot of sexual tension between us.

Rarely a day passed that I didn't think about sneaking in the shower with Jessica after class and showing her what it's like to be fucked by a man instead of a boy. The thought of picking her up, wrapping her legs around me, and using my 8" cock to pound her against the shower wall was the most popular fantasy in my masturbation rotation.

A fantasy was all I thought it would ever be until Jessica looked at her sister's phone to get my cell number.

"Make sure you look at the birthdays on the morning announcements" was all the text said.

I responded by asking "Who is this?"

When I didn't get a response I figured it was a wrong number and didn't think another thing of it.

The next day as I awaited the start of 1st Block I thought I heard the principal say Jessica's name when running through the day's student birthdays. Curious and remembering the text, I checked the announcements email and sure enough today was Jessica's 18th birthday.

Was it Jessica that sent me the text and, if so, why? I was puzzled and became even more puzzled once Jessica never mentioned the text after I wished her happy birthday. In fact, she even acted nervous around me and was obviously avoiding me. Finally, as I was sitting on the bleachers in between classes Jessica and I stared at one another as she strode out of the gym.

She looked at me differently than before and I felt the blood begin to rush to my cock. As soon as the school day was over, I went to my desk where I had confiscated about 6 cell phones from students who had them out during gym class and never reclaimed them. One belonged to one of Jessica's friends and I used it to verify that the number which texted me the night before was in fact Jessica's.

As I drove home, I accepted the logical conclusion that Jessica's text was meant as a means to start down a dangerous path. I decided I wouldn't respond as she was still a student.

That night as I was taking a shower I heard the familiar bell sound alerting me that I had received a text message. After drying off, I checked my phone and was startled to see a selfie video of Jessica nude and spread eagle on the bed aggressively rubbing her clit as she said,

"Coach Anderson, I have wanted to fuck you for a long time. I have fucked several guys but have never fucked a man. I get turned on just thinking of the big cock I always stare at as it bulges out of your gym shorts. I don't want things to be weird. I am not looking for a relationship. I just want to fuck you until I go off to college. I decided I would wait to make my move when it was legal. I will never tell so don't worry about your wife finding out. If you want it you can have it...The balls in your court."

By the end of the video my cock was hard and sticking out from the towel around my waist. As I looked at my big cock in the mirror I imagined it tearing Jessica's teenage pussy apart. If my wife hadn't been out of town for the week at a conference I would have jerked off, watched tv, and went to bed.

However, my wife was gone for the week and I sent Jessica a text saying "I want it, when and where?"

Her reply came so quickly it's like she already had it ready to send when she received my text. It read "my parents are gone for the week and I have the house to myself. Why don't you come over here?"

Shocked at our good luck I replied "My wife is gone for the week as well. Why don't you come over here since I live off the beaten path away from neighbors and prying eyes?"

"Ok I remember where you live. Be about 30 minutes. I can't believe this is finally going to happen!" she texted back.

To give her a glimpse of what she would be getting later on I sent her a picture of my fully erect manhood with the caption "I'll be waiting."

"My God" was all the last text she sent me said.

I smoked a little weed while I waited on Jessica. My cock never lost its hardness and was ready to fuck anything it could get in.

After what seemed like an eternity I heard a car pull up my gravel drive. It was almost dark but I could still make out Jessica's red accord pulling up in front of my house.

Opening the door in just my gym shorts, Jessica was standing before me wearing tight blue jeans and a white halter top without a bra. Her hair was pulled back and she had on nerd glasses that only made me want to fuck her more.

"Hey Jessica, come on in." I said nervously.

She seemed nervous as she was standing in the doorway but that all changed once she was inside and the door closed.

When I closed the door and turned around, she immediately was grabbing at my cock forcing me back against the door.

"I want to see it" she pleaded

In attempt to not disappoint her, I stepped out of my shorts and stood before her completely naked with my cock pressing against her belly.

"I have never seen a cock that big" she said as she struggled to get her hand around it as she slowly began to milk my cock.

Instinctively, I put my hands on her shoulders and forced her down on her knees.

Taking the cue she engulfed my cock with her mouth and began to suck it slowly taking a little more down her throat each time. I had been with girl's who could get most of my cock in their mouth, but I had never been with a girl who could take all of it down her throat.

"I am gonna fuck that beautiful face with my cock" I said in an authoritative tone.

I put each of my hands on the side of her head and held her head in place as I slowly began to ram my cock down her throat. Once I got about 6 inches in Jessica began to gag. I could feel her gagging on my cock and noticed small tears beginning to smear the mascara on her face.

I lost control and flipped her around and pinned her head against the door as my cock reached new depths down her throat. Once I finally got my cock buried to the hilt I felt the cum leaving my balls. I slammed my cock violently all the way down Jessica's throat and shot load after load of my cum down her throat.

Her face was a mess and she was still gagging on my cum when I pulled my cock from her throat.

"Sorry about that Jessica. I kind of lost control for a bit" I said hoping I hadn't scared her away.

"That was the hottest thing I have ever done. I just hope you have more left in the tank"

"There is plenty left in the tank. Come with me."

I took her tiny hand and led her down the hallway and into my bedroom. Just as I was getting ready to start tearing her clothes off the phone rang.

It was my wife.

"Hey honey, I was just calling to let you know I am going to bed early tonight."

"Ok, is everything allright?" I asked

"Yeah, I am just tired. These all day conferences wear me out." She replied

We then told each other good night and hung up. My wife had a strange tone in her voice and I swore I heard a man's voice in the background. Whenever, I turned back around I completely forgot what I was thinking about.

Jessica's naked body was amazing. She had an athletic build with just enough cushion to make some bounce in all the right places. She had a smooth pussy and perky tits that were in the 34c range. Her pale skin and brunette hair gave her that innocent girl look.

As I watched her use three fingers to fuck her little pussy my cock shot back up like it had been stabbed with adrenaline.

"I need your cock inside me" Jessica begged

I wasted little time in making my way to the bed. The fact that Jessica was staring at my cock instead of my face turned me on even more.

I was past the point of foreplay. I crawled up between her legs and began working the length of my cock up and down between the folds of her pussy. As I would slide my cock down her slit she would thrust her needy pussy at it trying to meet its need to be filled.

I wanted to bury myself in her, but I knew I needed to give her tight pussy time to lubricant itself with our juices as my cock slid between her lips.

When Jessica couldn't take it no more she reached down and grabbed my cock with both hands and began to force it inside her.

I couldn't wait any longer. I sat up and placed both legs around my head and leaned forward sending her knees towards her head.

"You want my cock?" I mocked

"I want you to fuck me with your big cock and show me what its like to be fucked by a man"

I moved my hips down and angled my cock towards the entrance to her pussy. As the head penetrated her outer lips I could feel her legs tense up against my body.

Not wanting to hurt her, I began to pull back.

"Don't Stop, just go slow" she instructed me as she pulled me in her with each of her hands on the cheeks of my ass.

I put all of my weight down on Jessica and slide my arms under her tense body.

Slowly I began inching my cock in her. She was experienced, but I could tell I was stretching her pussy to places it hadn't been before.

I would move my cock back a little and then forward a little more. Her pussy had a vice grip around my cock. It was so tight that when I would start to pull back it felt like her pussy was sucking my dick back in.

Once I got about ¾ of the length in, she had adjusted to the thickness and began to relax. I knew I could finally begin to fuck her.

Her hips were meeting my thrusts wanting more of my cock inside her. I finally changed my rhythm and met her thrust with one of my own and buried every bit of my cock inside her.

I could feel her body tense up and I decided to leave my cock planted still deep inside her to give her pussy time to adjust to accommodate my manhood.

"Are you ok?" I asked, only pretending to care.

"Oh yeah, I have never felt anything like this before" she moaned relaxing her body

"You haven't felt anything yet" I warned her as I began to set a rhythm of slowly pulling my cock out of her wet hole and slamming it back in her tightness.

"Pound me with your man cock" she demanded

The image of Jessica with messed up hair and mascara from the face fucking earlier coupled with her dirty talk brought out the animal in me.

I began thrusting deeply and furiously inside Jessica's worn pussy.

"Fuck me from behind. Make me feel like your little young whore"

Wasting little time, I pulled out of her and flipped her over on all fours with her head down and ass up.

The view of her shapely ass spread before me revealing her tight pink ass hole and moist pussy made my cock jump to attention.

I lined my member up with her entrance and immediately began fucking her as hard as possible. It was tough to discern moans of pleasure from pain as I was launching my length inside her.

I gathered up her long brunette hair and wrapped it around my wrist and pulled it back towards me as I impaled her repeatedly.

"Use me Coach. I'm your little whore. You can do anything you want" she said in a way that let me know she meant it.

I was about to cum inside her pussy, but I couldn't pass up the opportunity before me.

"Anything I want?" I asked as I removed my cock from her pussy and cushioned it up with the entrance of her tight pink ass hole.

She knew exactly what I meant.

"Anything" she slyly said as she popped her ass back at my cock.

I reached over and grabbed the lube off the nightstand and squirted a liberal amount at the junction of my cock and her ass.

"You need to try to relax Jessica and it will feel much better" I instructed her as I noticed her cinch up as the head of my cock began to open her back door.

"Ok, I have always wanted to be fucked in ass"

She finally trusted me and began to relax her body allowing my cock to slowly worm it way down her anal cavity.

With every inch her body would tense up and then relax alerting me to when she was ready for more.

As the last inch of cock entered her ass I noticed Jessica reach her hand back between her legs and begin working her clit.

I began methodically removing half my length from her ass and then smoothly forcing it back up her ass.

I watched her hand circling her clit and matched my pace to hers.

When she sped up her clitoral stimulation up I sped up my fucking of her ass.

By the time she maxed out her hand speed I was violently trying to split her ass in two with my cock.

"Oh God, I am about to cum" she screamed as she tightened her pelvic muscles

I felt the sperm awaken in my balls signaling it was time.

I buried my cock deep inside her ass and could feel the walls of her pussy contracting as she began having a powerful orgasm.

I frantically began fucking her ass and slammed it all the way in as I felt the sperm jolting from my cock.

My cock continued pulsing for 15 seconds shooting my seed in her ass.

When I finished it I slowly pulled my cock out of her ass and watched the cum sputter out and work its way down her leg.

"That was amazing" Jessica said to no one in particular.

Feeling proud I asked her if she liked being fucked by a man.

"I loved it and plan to fuck that man several times before I leave for college" she said as she flipped over on her back.

I told her I liked that plan, knowing things were beyond the point of no return.

To Be Continued