tagFirst TimeMy Teacher: The Arrangement

My Teacher: The Arrangement

byJim Stand©

I was a skinny, and shy college freshman when I met Ana, a blue-eyed, red-head with legs that never stopped.

I was in the adult section of a run down bookstore, reading what I had only imagined and beat off to during my adolescent years, a fold-out picture of a hot woman with a wet, shaven pussy and 36 C cup breasts! I licked my lips and dreamed what it would be like to play with tits like those. I was half-hard and leaking into my boxers, an activity I had come to thoroughly enjoy. Then suddenly someone from behind, tapped me on my shoulder, startling me so much I dropped the magazine. "Ever had that for real?"

Turning red I spun around to see what kind of prank was being pulled on me this time. My jaw dropped when I saw her. She was wearing stiletto heals that wrapped around her fine, slim ankles, a skirt that showed off her toned, long legs and a blouse that was cut to show off just a bit of her large breasts.

"Excuse me," I said, trying to regain my composure, but turning a deeper shade of red.

"I said have you ever had that for real? I have been watching you for over ten minutes and you have not moved a muscle, well except for your cock!"

"Um, a, well, I um, I, I, well, I guess, I mean, NO I have never had that."

"Would you like to?" she asked, grabbing my dick with her left hand.

My first thought was this was a dream and I would be waking any moment. Could this hot woman be asking me this, was it true, could it be? But for the first time in my life and with my second thought I said, "Yes."

"GREAT! My name is Ana, what is yours?"

"Jim." I swallowed hard.

"Then follow me Jim." she whispered turning to leave.

Ana led me to her car, opened the passenger side door and sat down on the seat facing me. She quickly unzipped my pants, pulled my hot dick out of my boxers and sucked me. Slowly at first, speeding up and then slowing down. She licked my shaft and kissed the tip of my dick, sampling the glaze that had leaked out. She went down again and engulfed my entire dick until it rammed into the back of her throat.

I was on fire and ready to come. I could not contain myself, my moaning was loud and intense and so was the pleasure. This was my first blow job ever and it beat-out any of the masturbation tricks I had tried time after time. Hell, my wet dreams could not hold a candle to what was happening this very moment either.

The blast from my first shot ran down Ana's throat, but for the second one she moved to just suck my head so I could fill her mouth. By the fourth shot, cum was spilling from her mouth and had started to run down towards her chin.

She swallowed every drop and licked my shaft clean. She then wiped my cum with her fingers and licked them clean, smiling as she gently bit down on the tip of her fingers one by one.

I was on the rise again watching her, but Ana was to have none of this. She ran her tongue up my shaft and kissed the top of my dick, then pulled away leaving me feel empty.

"You have to wait for more."

I secretly stroked my hard dick a few times before slipping it back into my pants.

"I can't believe my fucking luck!" she said as we got into her car. For over a year now I have been looking for someone to teach. I had given up and here you are, you just fall into my lap. This is your lucky day too. I am going to show you every way to please a woman. Does this arrangement please you?"

Still in shock but with a big smile I said, "Sure."

"What are your masturbation techniques?" she asked as we pulled out of the parking lot.

"Do you mean have I had a lot of practice?"

"No. I know you fuck yourself. I want to know how?" When and why did you start? Do you use any toys? Do you switch hands? Tell me."

I swallowed hard and began by telling her what brought me to start playing with myself.

"I was 14 when I caught my sister's boyfriend fucking one of her girlfriends from behind. It had been two in the morning and I had awakened because I was thirsty. I was heading downstairs to get a glass of milk and when I reached the landing and looked down.

I saw him enter her cunt from behind. She was bent over the coffee table and he rammed his thick dick into her, harder and harder with each stroke. Other than a few grunts and sighs they did not make much noise. Cum ran down the back of her legs when he pulled out. He scooped it up and fed it to her.

I began to stroke myself as I watched them fuck. When they finished I raced back to my room to see what I could produce. It did not take long. My cum plastered the bedroom door a few times before I even felt how warm it was.

The next day I discovered scratch marks on the table where she had been bent over. I guess she really got nailed. The thought excited me so I started to stroke myself again, but stopped as I heard my sisters open the front door.

A few weeks later I found a copy of my dad's Playboy and got hard just looking at the cover of a woman with 44 D breasts and legs that went on forever. I knew what I needed to do for release and went to my room, sat down and rubbed like mad until I shot into the air.

As time went on masturbation became an experiment for me. I switched from using my right hand to using my left to get a different feel. The loss of control by using my left hand kept me harder, longer. I could now go for over 45 minutes without coming, if I took it slow.

This provided the best cum shots ever. Sometimes I could make it fly into the air or hit a wall from over 8 feet away while other times I just let it melt all over my dick and used it as a lotion.

Then one day I decided I should taste myself.

As I told my childhood story to Ana she slowly hiked her skirt up higher and higher.

"Put your hand here!" she pointed to her upper thigh after I mentioned I had tasted my own cum.

I put my hand where she had specified. She was warm and wet. I started to go up higher. I reached her lips and started to rub my finger over them just as we stopped at a traffic light.

A truck pulled up next to us and two guys inside the truck looked down at us with interest.

"Stick your finger in now!" she instructed.

I gladly did as I did as told.

"Let me help" and she used a finger from her left hand to join mine.

Her pussy swallowed my finger until the base of my hand reached her lips.

"I love to be watched." she sighed as she started to gently rub herself.

The two guys dropped their jaws and started to drool. Their eyes misted over and my guess was they were probably jerking off while watching.

As quickly as we got into the action the stop light turned green.

"Enough for now, were almost there" as she jerked my fingers out.

I licked her juices off my digits, enjoying her sweet taste as she smiled at me.

We arrived at her loft and entered the lobby.

While waiting for the elevator my eyes locked onto her sexy body. I did not notice how fine her ass was before. Not huge, but it was perfectly round and I could see the outline of her G-sting because her ass poked out through her skirt. "Do you like anything in particular?" she sighed turning her head to see me.

"You have a terrific ass" and I reached out to slap it. My hand remained there longer than it should have. I could barley cup her ass with my hand, but wow, was it ever tight. I quickly imagined prodding that with my dick like I had seen in so many movies.

We walked into the elevator. She pushed the 3rd floor button but then pushed the stop button after it went up half a floor. The alarm sounded as she turned towards me with a big grin, dropping to her knees.

She pulled my pants and boxers down around my knees and began to suck me again. Being exposed with a sexy woman ready to suck my dick caused it to rise in an instant.

I really could not believe this was happening to me. Less than 30 minutes earlier my dream of a woman sucking me off in public happened and now another dream of getting blown in an elevator was about to get started.

My knees weakened as she blew on my dick. When she started to suck by cock I could not stop from smiling.

Ana worked my dick like her favorite popsicle. The heat was welling inside of my balls and the pressure was mounting like a volcano ready to burst. I moaned louder and longer, louder each time she licked. She twisted her tongue around my shaft and I let out an excited cry.

She could tell I was getting closer to unloading and the second before I came; she stopped sucking and just licked the tip.

I exploded spraying onto Ana's outstretched tongue, on her check and on her chin. My second shot hit her forehead and the third nailed her chin with so much cum and my potion dripped down between her breasts.

She looked up and smiled as cum dribbled down her face.

"I love fucking cum. It fills me up and fires me up" and she grabbed my hand to feel how wet her panties were.

What I got was more than a wet hand. My hand brushed against her lips and she moaned so I grabbed a little more and she moaned louder.

For some reason the stop button released and the force sent my fingers into her wet pussy. She moaned very loudly but quickly regained her awareness.

"Wait!" she ordered, slapping my hand away.

My pants were around my ankles when the elevator door opened. Nobody was around, but for some reason I wished there would have been.

Somehow I stumbled into Ana's loft.

As soon as the door closed she went down and began sucking my balls and running her hands slowly up and down my wet, limp dick.

She paused to take off her blouse and then put my cock between her cum filled cleavage. I instantly hardened as cum mixed into my dick.

Ana moved up, starting to suck me again but quickly switched giving me a hand job instead.

She tightly squeezed my dick then ran her hand over it really slow. She got her finger right under my bulb and worked it slow, like I had done so many times before. This put me over the edge and I came again.

Ana aimed my dick at her breasts and I shot into them. The first blow landed right in the middle and the second hit her throat. The third spray landed right on her left breast's big, brown nipple. The next shot went array and somehow hit her right ear.

"Smear your cum into my breasts and feed some to me!"

I did as I was told.

There was so much cum on Ana. She decided it was a good time for me to taste my own potion and ordered me to suck her left tit clean.

I dropped to my knees and cupped her breast. I stared for a bit, admiring her 36 C, sexy and now very hard breasts. My mouth was getting moist just thinking of the taste so I went for a sample.

My mouth clasped around her nipple as I gently bit it. I licked her tits like an ice cream cone. The salty taste of my own cum mixed in with the rose smell of her breasts was pure heaven.

I ate and ate. Again, I could not believe this was happening.

When I finished, she walked over and cleaned herself up with a dish towel, leaving off her blouse.

She then got two glasses of water from the kitchen and beckoned me to sit with her. My god, her breasts were so damn perky even without the bra and they gently bounced with every step.

I tucked my wet dick inside my shorts and pulled my pants back on, then went to sit with her.

"Let's talk about us and the arrangement I mentioned, before we continue."

Ana was 31, divorced, had no kids and worked as a dental hygienist by day. When younger she was a dancer and used the money to pay for school. Her favorite hobby was sex and just about any kind.

"What do you mean?" I asked her.

"You already know I like to be watched by others but I also like to film myself too."

She went on telling me how she loved swapping partners, group sex, oral sex and toys like tit claps, dildos and eggs. She regularly went to sex dinners and was starting to get into role playing as well.

"I like to dominate but love being dominated as well."

Her eyes lit like fire when she said this.

"What don't you like?" I stuttered.

"Only one thing, I won't fuck my family and don't want to know if someone else does either. It makes me sick!"

I was relieved. At least she had some boundaries. I told her a brief synopsis of my life. I was a 19 year old, college freshman studying environmental health. I was born and raised in Boston, had two older sisters that treated me like the younger brother and was never and still am not, in the popular crowd.

"What do you mean?" she asked.

"I was always very shy around woman and my sisters' knew it. They knew I dreamed about fucking their friends but also knew I would never do anything.

They would invite their friends over and make sure I would catch them undressing. If I was by the pool when they were out tanning with their friends, they would rub each other down with oil, but rubbing in places they knew would send me to my room in a hurry.

At school I was always ignored, not beaten or anything, just ignored. Everybody in school knew I was the brother of the most popular girls, so they left me alone. I was a tall, skinny kid with no muscle and shy, a mixture that did not work and my sisters, Kate and Kelly and their popular girlfriends made sure it never would." "That will change!" "Now about our arrangement. As I told you before, I will teach you how to totally please a woman and show you how to experience sexual fantasies with both men and women. I will see you socially. We will be a couple, going out to dinner and parties. I will teach you things that books cannot. You don't need to worry about money. When we go out, I can buy if you can not. For this I expect you to please me sexually and you will also be pleased. At times I will tell you to go test your new found learning and come back with a report, but that will not be for some time as I can tell you need some molding. Is this agreeable to you?"

"YES!" I almost screamed.

"By the way all that sucking made me hot and wet as you witnessed earlier."

She pulled a large, purple dildo out from under the coffee table.

"Let's explore my pussy!"

Of course I followed.

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