Confessions of a High School Whore: Chapter Four

Before I get back to writing about my time as a teenage prostitute I thought I’d write about one of my favorite experiences, the time my mom and I gave Robert a sex ed class he’d never forget.

My name is Gail Storm, and this story takes place on a Saturday in the fall of 1985. I was 16 and one of the most popular girls in our high school. I was also one of the hottest. I was 5’7. Weighed 110lbs. Beautiful 34C breasts. And at the time I had medium length, spiky blonde hair.

The day before, Robert, the biggest nerd in school, and I were paired-up in acting class. We went to his house to rehearse. In his bedroom I discovered his stash of porno mags. Just knowing that he stroked himself to these mags turned me on. So I persuaded him to play with himself for me. When he nervously showed me his cock it was the longest and fattest one I’d ever seen. I had to have it in me. Even though he had a gigantic cock he had no idea how to use it. When I got home, I told my mom all about it. She had a plan to turn Robert into a stud.

I woke-up the next morning to my mom eating my pussy. It felt so good as her tongue circled my clit.

Most people thought my mom was my sister. We looked a lot alike. She was 32 and was younger than any of my friend’s parents. They also thought that was an interior designer; in actuality she ran an escort agency in metro Detroit, where I was also employed. And if you haven’t figured it out by now, or read the other chapters in this series, my mom and I were also lovers.

She stopped licking my pussy momentarily that it was time to call Robert and invite him over. As she resumed eating me out, I picked-up the phone and dialed. It rang three times before Robert’s mom picked it up.

“Hello,” Robert’s mom said.

“Hello, is Robert home?” I asked trying to hide the pleasure I was getting from my mom’s tongue.

I then could hear her yell, “Robert, phone. It’s a girl.”

I tried not to laugh. While waiting for Robert I started to have an orgasm. As I was about to scream I bit my lip to be quiet. But it didn’t work.

“Is everything alright?” Robert’s mom asked, unaware what was going on in my house.

“Sorry a book fell on my toe,” I said trying not to laugh.

I then looked at my mom and mouthed, “Stop.”

Of course she didn’t listen.

As she continued licking and fingering me Robert finally picked-up the phone.

“Hello,” he said from the other end.

Just hearing his voice got me wetter.

“Hey Robert, it’s Gail. I know we didn’t get much rehearsing done yesterday, so I was wondering if you had time today?” I asked.

“Sure,” he replied

“Come over around 1,” I said. I then gave him my address and hung up.

My mom then told me to get on all fours. She pulled out two toys from her drawer and inserted one into my pussy and the other into my ass. She then fucked me with both of them until bringing me to another, but more intense orgasm.

I then collapsed into her arms. While my mom was stroking my hair she said, “You really like this boy, don’t you?”

“Robert Cohen? You’ve got to be kidding,” I exclaimed.

“Honey, the second you heard his voice your pussy got wetter. The body doesn’t lie,” she said.

“Mom, I like his cock but Robert Cohen is a loser nerd,” I said.

“Uh huh,” she replied.

“You’ll see what I mean when he gets here,” I said.

I then left, made some breakfast and watched TV. But all I could think about was Robert. Just the thought of him got me horny. I tried to think of all the other guys I’ve been with. They were better looking and knew how to fuck.

I went into my room, spread my legs and started to play with my pussy. The only face I could visualize was Robert’s. Why was he haunting me this way? I closed my eyes, rubbed and dreamed that Robert was the greatest lover in the world and brought me to the greatest orgasm my body ever experienced.

I then looked over at the clock and noticed it was noon. I went and took a shower. Masturbated some more. When I was done drying my hair and making myself prettier I walked back to my room to find my mom sitting on my bed holding a white nightie. She then handed it to me and told me to wear it.

My mom then said, “Wait in here and I’m going to send him in here.”

“Okay,” I said as I put the nightie on.

She left the room and I lied on the bed rubbing my pussy in anticipation of Robert’s arrival.

Promptly at 1 P.M. the doorbell rang. I furiously started rubbing faster.

I could hear Robert ask, “Is Gail here?”

I could then hear my mom give him directions to my room.

Seconds later there was a knock at my door.

“Come in,” I said seductively.

He opened the door and by the look on his face you could say that he was shocked to find me wearing a white nightie, lying on my bed, playing with my pussy.

“I can’t believe you’re this, your mom is out there talking to my mom,” he said with a stutter.

“She’s cool,” I said.

“Are you sure?” he asked while fixated on my pussy.

I could hear the front door slam shut. I then looked at Robert and said, “Yes.”

He just stood there dumbfounded, staring at me while I played with my pussy.

“Don’t I look pretty?” I asked.

He shook his head yes.

“Now get naked and join me,” I ordered.

At this point he started to let his cock do the thinking. He no longer cared that my mom was in the house and could walk in at any moment. Right now the only thing he cared about was getting his clothes off as fast as possible. When he was fully naked, he was no longer the nerdy 16-year-old boy that stood in my room, a 6’1 175 lb beautiful man now stood there with a gigantic hard cock sticking toward me.

I then yelled, “Mom his cock is hard.”

My mom quickly entered the room also wearing a white nightie. A startled Robert picked-up his pants in an attempt to hide his boner. He looked freaked. All he could say, “But that’s your mom,” over and over.

“It’s okay,” I whispered into his ear.

My mom grabbed them away from him, smiled from ear to ear and said, “Gail, grab me a ruler from your desk.”

I eagerly ran to my desk, got a ruler and handed it to my mom. She then put it against his large member and said, “Fuck! Yours is shy of 11-inches, it’s one of the biggest I’ve ever seen.

She then turned to me and ordered me to jerk him off. She kept telling me to go faster as I frantically stroked his cock. As the tempo of my stroking increased she yelled, “I want to see him cum.”

As I increased my hands speed, I could feel Robert tremble. Seconds later he shot his load all over my room. As soon as that was over my mom started kissing him and said, “Good boy.”

She then turned to me and said, “Gail, get me a washcloth.”

As I ran to the hall closet I could hear my mom say, “Robert, you have a beautiful gift, you need to know how to use it. Today I’m going to teach you how to fuck. How does that sound?

I returned as Robert said, “That sounds good.”

I then handed my mom the washcloth. Before she cleaned him off she scooped up some of the cum that landed on Robert’s chest. “Mmmmmmmmmm,” she said before cleaning wiping the mess away.

I returned to my bed and started playing with my pussy. Even with my mom tugging away at his cock he couldn’t stop looking at me. “Do you think my daughter is pretty?” she asked him.

“Yes,” he said.

“Go join her on the bed,” she told Robert.

He walked over, sat next to me and just stared. My mom crouched on the floor in front of us, played with her pussy as she told Robert to start kissing me. As his lips touched mine, my hands moved down to caress his limp cock and bring it back to life. As I did that my mom walked over, removed one of the arms Robert was hugging me with and inserted it into my wet pussy. She guided his fingers onto my clit and said, “Rub it.”

She then had him stick his fingers in and said, “Move them in and out like you would your cock.”

I started moaning load. But before I got to used it my mother pulled him away and said, “My turn.”

Watching my mom make out with Robert as he finger fucked her was turning me on. I started rubbing my pussy as I watched the tempo of his finger thrusts increase. With every thrust my mom’s moaning got louder. Soon her body started to shake. She pulled his fingers out of her as she screamed, “I’m cumming.” She then started kissing him passionately.

I thought they forgot about me. To remind them that I was there I started moaning loudly as I rubbed my pussy. My plan worked perfectly, I was noticed. My mom stared at me approvingly. She nudged Robert and said, “Look at Gail.”

He glanced over and saw me masturbating.

My mom grabbed a hold of his hard cock, started stroking and asked, “When you fucked my daughter yesterday did you eat her pussy?”

“No,” he replied.

“Do you know how to eat pussy?” she asked.

“No,” he once again replied.

She looked at me and said, “Gail, get on your back and spread your legs.”

I did as I was told.

She looked at Robert and said, “I’m going to teach you how to eat pussy.”

My mom then spread my legs even wider. She pointed to my clit and said, “This is what you want to concentrate on.”

She then started rubbing my clit.

I started moaning.

My mom then told me to hush as she continued the lesson by saying, “I want you to kiss her clit and suck it. Your tongue can go anywhere, just as long as the clit is your bulls eye.”

She then demonstrated by eating me out. I looked at Robert stroking his cock as he intently watched my mom fuck my pussy with her tongue. His cock looked so massive his right hand moved up and down. I began to worry that Robert was going to enjoy watching my mom and me that he’d blow another load before letting me experience his large cock one more time. To make sure that didn’t happen I yelled, “Mom, stop him before he cums.”

She stopped pleasuring me, turned around, slapped him on the hands and said, “Don’t do that.”

Next she had Robert get on his knees between my legs to take his turn. It was obvious that not only was he paying attention to my mom’s lesson plan, but that he was also a natural. All of the boys and most of then men did not really know how to work it down there, but for some reason or another he was hitting my magic spots sending me into orgasmic bliss.

As I was screaming, “Don’t stop,” my mom whispered into my ear and told me that it was time to reward Robert.

We had him lay on his back on my bed. My mom sat on his face and I moved between his legs and put his massive cock into my mouth. As my lips slid up and down his 10 3/4 long, 4-inch wide unit, my mom leaned over and held my head, forcing my gag reflex to kick in. After she set my head free, her mouth joined mine on Robert’s shaft.

A few minutes later after out tongues worked their way up to the head of his cock, mom asked, “Do you want to sit on it?”

I smiled and replied, “Yes.”

My mom got off of his face, laid down next to him, started stroking and sucking his cock. I stood above him rubbing my pussy. My mom told me to slowly lower myself onto it. As I got close to putting it inside of me my mom teased my pussy with it. She made me beg for it.

After she thought I begged enough, she held it still and I lowered myself onto it. My mom watched in awe as his gigantic cock stretched out my tight 16-year-old pussy.

“Do you love his cock baby?” my mom asked.

“Oh yes,” I replied as I was riding it to Heaven.

I leaned down to kiss Robert. As our tongues used each other’s mouth as a playground, his cock came out of pussy. My mom grabbed it and started sucking it. She selfishly did not want to return it. After making me beg for a few moments she returned it to its rightful place—my pussy.

A few minutes later he started thrusting faster, his body started shaking. Then it happened, his cock exploded and cum squirted out filling my pussy. As soon as his penis exited me, my mom bent me over and licked his juices out of my cunt.

As my body laid on top of Robert’s, my ass was now perched in the air with my mom’s tongue inside of it and my pussy. My moans brought his cock back to life. As it once again became erect, it stabbed me in my stomach.

I’ll admit that wasn’t the most comfortable position. I had to get-up. I then decided to sit against the wall. I spread my legs and invited my mom to once again pleasure me with her tongue.

Robert stroked his cock watching my mom eat me out. I looked at him and said, “Isn’t this better than all of your issues of Hustler?”

He smiled.

I then asked, “What would the guys in those magazines do?”

He appeared to be thinking about my question as he continued to stroke his cock, and then the light bulb in his brain finally went off. He stood-up, walked behind my mom and entered her pussy from behind. As he did that she squealed with delight.

“Fuck my mommy,” I yelled as he rammed her from behind.

I then got-up off the bed moved closer to Robert and started kissing him. I looked down and watched his large cock pound my mother. I needed and wanted it so bad that I cried out, “I want to taste mommy’s pussy on your cock.”

He pulled out. I then got to my knees and put it in my mouth. Seconds later my mom dropped to her knees and we were both playing his cock as if it were an old harmonica.

My mom then had me kneel on the bed. My mom stood on it. Robert started fucking me from behind as I fingered my mom.

As Robert’s cock continued to ram me I realized that this was the longest he’s ever lasted. And I prayed that I didn’t jinx that by thinking about it.

A few minutes later my mom had me lay on my back. She got on top of me, with her ass and pussy sticking right in my face, Robert stood above me. As his cock went in and out of my mother’s pussy I was licking my balls. At the same time my mom was once again eating me out.

Soon my mom and I were sitting next to each other on my bed. Our legs were crossed and Robert’s love missile went from pussy to pussy. Soon he started shaking. My mom could tell that he was ready to explode. She removed his cock from my pussy and then he blew his load all over us. He then plopped on the bed between us.

As we laid there kissing my mom went and got a hot washcloth to clean us up. She then looked Robert right in the eyes and asked, “Think you can go again?”

“I think so,” he said as his limp dick was coming back to life.

She looked at me, then back at him and said, “You two have fun.”

She then left the room.

“Your mom is so cool,” Robert said.

“Shut-up,” I said as I lunged at him and immediately started kissing him.

His mouth moved down and started kissing my neck.

Both of my hands wrapped around his massive member and started stroking it.

He moved down to my nipples. This brought an even bigger smile to my face.

“Pinch them,” I asked.

He did as he was told.

“Mmmmmm,” I said as his fingers squeezed them.

He then had lay on my back. He then spread my legs and put his head between then. As his tongue circled my clit, I closed my eyes as he once again hit my magic spots.

I then had him lay on his back. I sat on his face, leaned down to suck his cock as he continued to eat and finger my pussy. As much as I enjoyed his cock in my mouth and his tongue in my vagina, I’d much rather have his large unit in there.

I got on my back and spread my legs He stood between them. I had him enter me slowly; I wanted to savor watching it go in. I rubbed my clit after it was fully inside and he started fucking me. Watching his gigantic cock move in and out of my wet pussy was getting me wetter,

After I was tired of that position I got on all fours. I told Robert to tease my asshole with the tip of his cock before putting it back in my pussy, His cock was moving at a snails pace. I wanted to get fucked, so I screamed, “Fuck me harder.”

He did. And to reward him for that I wiggled my ass and moved up and down his large cock. A few minutes later he pulled out of my pussy and ordered me to suck his cock. I have to admit that this was the first time he showed any sort of dominance in the bedroom. I’ll admit it turned me on. So I repositioned myself on the bed and put his pussy soaked penis into my mouth.

After a few minutes of oral bliss he laid on his back and I climbed on top. I rode his cock as if it was the last one on Earth. I might have been going a little too crazy, because not even 5 minutes later he said, “I’m going to cum.”

“Fill me up,” I cried second before his pulsing cock exploded and his hot load shot into my pussy.

I collapsed into his arms and we started kissing. As I looked into his eyes it dawned on me how much I actually liked him. And how would I explain to my friends that I was falling for the biggest dork in school.