Sweet Summer Fling: Must It End Already?

I don’t want my sweet summer fling to be over!

All of my girlfriends are so excited that it’s finally fall, officially starting today.  It’s all they are talking about.  My girls want their pumpkin spice lattes and cozy sweaters and group chats about sexy Halloween costume ideas.  And I just want to hang on to the sunny days, sweaty sex, and my sweet summer fling!

I met Jackson on the first day of June.  I was on a date, and my date happened to take me out on a sunset cruise around the bay.  Jackson was one of the cute deckhands.  And the second our eyes locked, I knew he was going to be my sweet summer fling!  He was tall, blonde, and very tan.  Add to that those amazing muscles from working on the boat.  I had to really focus on my date that afternoon.  Because I just kept shifting in my seat, hoping my wet pussy wasn’t soaking through my panties onto my sundress.

Quickly, I ditched my date.

As soon as the boat docked, I thanked my date for a wonderful time and told him to call me.  But I already knew he wasn’t going to be the sweet summer fling I was looking for.  Then I waited by the ramp hoping that Jackson might be getting off work.  Lucky for me, my timing was perfect.  And after only waiting a few minutes, he walked off the boat and directly toward me.  Ever the gentleman, he shook my hand and introduced himself.  And asked if I wanted to take a walk.  I suggested that we grab a drink instead.  But then he dropped the bomb.  He wasn’t quite twenty-one yet.  In fact, he was working on the boat over the summer to save money for his first year of college.

I didn’t expect my sweet summer fling to be that much younger than me.  But Jackson was just so sweet, and kissable, and ultimately fuck-able, so I refused to let it bother me.  After our walk, he took me back to my car.  Then he asked if he could kiss me.  His lips were soft, and his kisses even softer.  He pulled me closer, and I felt myself melt against his body as his hands gripped the back of my head.  I didn’t want the moment to end!

I was falling in love with my sweet summer fling!

Jackson also worked as a lifeguard at the community pool.  So I spent any free time I had soaking up the sun and watching my sweet summer fling hard at work.  I loved watching his tight, sweat-drenched body in his red swim trunks.  Most of my time was spent counting down the minutes until his shift was over and he could come over and give me the first kiss of the day, although the first kiss of many.  Since he still lived at home, I’d bring him back to my place for a hot make-out session.  But he would never try to go any further.

I was a little frustrated.  I wanted my sweet summer fling to fuck my brains out.  But he was just too sweet!  Finally, I took matters into my own hands.  Jackson was heading off to school soon, and my pussy ached for my sweet summer fling.  I couldn’t let him leave without feeling his dick inside of me.  So one night, after a delicious kissing session, I slipped my hands in between in legs and slowly unzipped his pants.  His body stiffened, and he grabbed my hands.

“I, uh, it’s just that… Well, uh, I, um,” Jackson stuttered.  I looked at him questioningly.  “Well, um, I’ve never done anything like that.  With anyone.  Ever.”

I couldn’t stop my mouth from falling open.  My sweet summer fling was a virgin?  Do you think I became his first?

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