One Night Stand Chronicles - Ashley

In the beginning there was me, not what you would expect as a Lothario, Jesse Henry.  My dad thought I was gay when I was a teenager because he never saw me go on a date or have a girlfriend. I just let him believe that so he would get off my back.  My mom tried to set me up but it never worked into anything with those girls.  They were worried. My dad worried that his only son was gay and my mom wished I were gay and not some weird recluse.

Now,  I am 35 and I have already had sex with over 40 women. That may not sound like a lot to you but for someone with my background…it’s a substantial number.

I grew up as a glasses wearing nerd that didn’t lose his virginity until he was 18.  I was terrified of getting close to women. I was sure that they would take one look at my 6 foot tall lanky frame, covered in lame clothes, with a bad case of acne and would run as fast as they could.  As you can see my self esteem was really low and so I avoided dates, prom and sex until I was 18.

However, once I lost my virginity…I became an entirely new man. I became the man I was meant to be. So many women wanting to have sex with me and I could not turn them down. I was smooth, good-looking and educated.

 I was irresistible.

Okay, that’s a lie. I am as clumsy and nerdy as I was when I was 18. That nerdiness however got me a great job and I met quite a few strange people and ended having more sex than I could ever dream of.  That could be the reason. That fact that I drive a really nice car could also be the reason.

Some of the situations were by chance and some were luck, but they happened and my friend thought I should write them down and document them. I am not very convinced that my stories will be all that interesting. I am no Don Juan and I am not a Casanova. I am just an extremely lucky guy.

So here you go.

Here is my story.

***

Ashley 

I was shocked when I entered her house. It was a mess. No wait…it was filthy. How did a woman that looked this good and smell so sensual have such a dirty nasty living space.  Her There was laundry everywhere, kids toys thrown about and it smelled like raw spoiled beef.  Yet, my goal wasn’t to clean her house. I just wanted to fuck and get the hell out of there. I just held my breath and followed her to her bedroom.

Her bedroom was no different from the rest of the house. The closets were so full of clothes the doors wouldn’t close.  The bed was unmade with piles of clothing on top. 

“Just let me move these clothes.” She said tossing pile after pile onto the floor. 

When she was done she began to undress.  She had an amazing body. I couldn’t wait to get my dick between her thighs. After she was done undressing, she undressed me.

“Oh look at that big dick.” She said dropping to her knees and taking it into her mouth. 

I wasn’t prepared for that. I stumbled back a little and she reached around and grabbed my ass pulling me closer. I looked down and watched her practically eat my dick. I heard of girls that could practically swallow your dick and looked like Ms. Peterson was one of those. She kept gagging on my dick.

The thought of how complicated this was. Those thoughts crept into my head as I watched her slurping and gagging.

Ashley was normally Ms. Peterson. She and my Mom had been friends for a long time and as I grew up I noticed she was looking at me differently. When I was outside cutting the grass she would compliment me on my muscles and how much I’ve grown. It slowly went from compliments to sexually harassing me under the dinner table when she came over to visit. She would stroke my dick and get me hard. Then she would stroke me.  

Now, Ashley was an incredible looking older woman. She has beautiful dark skin, with long micro braids in her hair.  She had a nice smile and a banging body.  She had nice breast but the best part was her massive ass.  I wondered what it would be like to fuck an ass like that.  I enjoyed it when she stroked me and I was eager to stroke her.

This evening, it was a couple of days after I graduated from high school and she insisted she had a graduation gift for me.  I knew what she wanted unlike my parents. They told me goodbye, they were going out for the night and don’t forget to stop by Ms. Peterson’s house.

“She has a graduation gift for you.”

So yes, she was my first. My mother’s friend was my first lover and who started me on my quest to fuck as many women as I could.

I felt like I was about to come when she pulled back .

“I want you to eat my pussy.” She said.

I was nervous for two reasons.  I had never eaten another woman’s pussy before and I was afraid her pussy might like her house…filthy.

She climbed on the bed and spread her legs.  I was happy that it was clean shaven. There was no hair at all and so it looked clean.  I climbed on the bed and just stared at her pussy. She sighed.

“Don’t stare at it. Eat It!”

Her words made me jump and so I bent down leading with my tongue and with my eyes closed I went for it. I just started licking which is what I thought you were supposed to do.  I heard her sigh again and opened my eyes.

I realized I was just licking her thigh. 

“Just forget it.” She said sitting up on the bed.

I was disappointed. I really thought this would be my moment. I climbed off the bed and began to find my clothes so I could get dressed.

“Where the hell are you going?” she questioned.

“I..uh. You told me to go.”

“I didn’t tell you to go. Take those clothes off and get on this bed.”

I obeyed taking my clothes and climbed back on the bed.

 “I want you to fuck me from behind.” She demanded.

She turned and threw her big ass in the air.

Shit she had a fat ass. I could not begin to comprehend what I was supposed to do with that. Each

cheek was the size of my head. I reached on her side table and grabbed a condom.

I began to fuck her. I felt like I was going crazy pounding her pussy.  Apparently I was not.

“Fuck me harder!”

I didn’t want to say that I was fucking her as hard as I could already.  I just propped my foot up and fucked her as hard as I could. 

“Slap my ass.” she demanded.

I did as I was told and slapped her ass.

She came and it was the first time I had ever felt a woman come on my penis. I could feel her juicy walls grip my dick and that was it. It was over for me. I came hard filling the condom with my gooey sticky cum.

I was breathing hard like I had just run a marathon.  I fell over on my back staring at the ceiling. Sex was good. I was determined to have more sex.

Ashley looked at me as if she were disappointed.

“It’s a shame. You got that big dick and don’t know how to use it.”