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Vacation sex
It started with my older step sister when she was a senior in high school. We were on a family vacation when she walked into my room and caught me with a penthouse magazine. She read the stories out loud and that lead to mutual masturbation.
She would put on these silky panties then straddle me when I was wearing thin running shorts. She would rub her pussy up and down my shaft until she would have an orgasm and I would cum in the shorts.
So this one time she said it would feel better for both of us if I would take my shorts off. It really did I could feel the warmth of her pussy and some wetness through her silky underwear. Often she would laugh when she would lift up just in time to see me squirt cum onto my stomach.
We were on what was likely our last family summer vacation. When our parents were asleep she would come into my room in the condo and we would do our thing. This one night she came into my room this time wearing a very short silky robe. I pulled down my boxers and as she straddled me I could see she didn't have underwear on this time. It felt so amazing to have her bare wet pussy lips sliding up and down my cock. The bare skin had us both having an orgasm rather quickly.
A few days after we got home she came into my room and had a condom with her. We were both quite excited at the prospect of actually having sex.
She rolled down a very thin slimy condom then straddled me. Up on one knee she guided my cock so the tip was parting her thick pussy lips. It felt so good to actually enter her warm snug pussy. She moaned a bit and wrinkled her nose when I was fully contained inside her vagina. My sister put her hands on my chest and rode up and down. I put my hands on her hips to hold her still, she would sometimes giggled when I would fill up the condom with cum.
We fucked just about every day for the rest of the summer. My favorite position turned out to be doggy style as I had a perfect view of my penis stretching open her pussy and going in and out. My sister liked it just as much as it was the only position the tip of my cock could touch the back of her pussy
Her last night she said she wanted to do something different, bare skin on skin with me, adding it would be ok for me to cum inside her.
It was a whole new and wonderful sensation slipping into her pussy, so very warm and wet, I could feel the texture of her tight pussy rubbing against the head of my cock. The most amazing part for both of us was when I came inside her. The warm cum surrounding my cock and leaking out. That caused her to have the most intense orgasm she had ever felt.
In college she got a boyfriend and we never had sex again.
I'm grateful for my older sister.
I was 15 and a virgin and it was the summer before her senior year. We had strict parents and her boyfriend/current husband was a year older. It was common for him to come over while our parents were not home. The'd go to her room and close the door. I never snitched.
He got a baseball scholarship at a college 4 hours away and moved to start summer courses and join the team early.
We lived near the beach so my sister and I would go in the morning and come home around noon. I admit, seeing my sister in a tiny bikini all day was nice. I couldn't wait to get in the shower and jack off. During the these trips, she asked if I had a girlfriend and I confessed being a virgin. She confessed her current boyfriend was number 5 for her. She told me who her first was and the others were one time hook ups at parties she went to when she was supposed to be spending the night with her friend.
One morning, my sister came to my room wearing her bikini and asked for a favor. I had just put on my shorts and asked what's up. To this day, her voice saying the following is forever etched in my mind.
She said, "I need to borrow dick. It's been 3 weeks and I'm horny." I was in shock. She sat next to me and rubbed my dick and said, "Oh come on, we can both have fun and I promise it will be OK because you're going to wear this." She held up a condom. That was the beginning of a very fun summer.
That was 25 years ago. We never had sex after that summer but to this day we are very close.
Bullshit story
You lucky dog!!!
Thanks! I'm not going to lie! It was the best summer I ever had!
She really helped prepare me for when I started having sex with girls.
After that summer, I had confidence and could control my orgasm to last longer.
I need to cum in your sister too!