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.
