Cruising with My Sister and Friends

My twin brother and I got an apartment together shortly after we turned 18. When our little sister Mary turned 18 a year and a half later, she still lived at our parents' place, though she began hanging out at our place many hours of the day and night since it wasn't out in the middle of nowhere. She kept some clothes there, and several of her friends began hanging out there as well.

An apartment full of teenage girls that just graduated from high school and had a tendency to leave the kitchen and living room very messy can be rather annoying. On the other hand, an apartment full of teenage girls that just graduated from high school presents many visual treats. Especially when the apartment complex has a pool and the apartment only has a small air conditioning unit, just powerful enough to stave off heat stroke on a hot day, it didn't really get comfortable inside on the hottest days of summer. So there was plenty of eye candy using our bathroom as a changing room before heading out to the pool in skimpy bikinis.

Some days, my sister had almost a dozen friends over, and I was almost constantly erect from all the delectable female flesh walking around. Judging by the look on my brother's face, and the way he shifted in his chair, I suspect he was as well. My sister was a cheerleader in high school, and was still friends with many of her squad mates. I was in the marching band, and got to know some of them from working together for pep rallies or at school sports events.

Most often, it was just my sister's two best friends, in addition to her. Janet was about 5'2", a very petite blonde with perky little breasts and an ass that could give a statue an erection. Janet was the one they threw high into the air at football games, and I think she sometimes forgot to wear anything under her little skirt, at least it looked like that from my seat in the band section at the games.

Sarah was a tall blonde, 5'10", with legs that seemed to go on forever. The kind of legs you could suck on for days. She had good sized breasts, and seemed to dislike wearing bras, since her nipples were often noticeably through her tops.

My sister was the hottest girl at school, and I don't feel any shame admitting that during high school, visions of her sent as many loads of jizz into a towel or down the shower drain as all the other girls at school combined. 5'5", long dark brown hair, spectacular C cup tits (I checked the size on her bra while pulling her laundry out of the dryer recently), with perfectly sculpted legs and ass. Mary ran a lot to keep in shape, and could have been on the varsity track team, if she wasn't so busy with cheerleading.

One night, I was settling in to watch my favorite show on TV, and my sister, Janet, and Sarah wanted to go out. My sister's car was in the shop, so they were bugging me to drive them. If it was a simple matter of dropping them off somewhere, I would have said yes. They wanted to go cruising, driving up and down the two one-way streets that pass through the entire town. I had plenty of gas, so the only issue was my time. They were dressed up to pick up guys, and I didn't want to spend my night watching three babes who weren't planning to sleep with me pick up random dudes. My brother was out of town for a couple of weeks for his annual National Guard training, so they couldn't ask him. They offered cash, future favors, and anything they could think of to try and get me to drive them. My sister even offered to find a chick for me to have fun with that night. I doubted how well it would work, though Janet seemed to realize that might be the motivation to get me to drive them, based on what she said next.

"C'mon Jake, we'll have sex with you if you drive us." Mary and Sarah just nodded their heads at this idea.

"All three of you? Actual sex, not just a quick feel, making out, and a hand-job?" Which perfectly described most of my dates, the few I got in high school and since. I wasn't a virgin, but I didn't get laid as much as I would like.

The girls looked at each other, and there seemed to be some non-verbal communication before they turned back to me.

"Yes, all three of us will have sex with you," my sister said.

I couldn't believe what I had just heard. My sister who I had lusted for since shortly after puberty was actually saying she would have sex with me, and in a group setting. As my dick quickly swelled in my pants at the idea of fucking my sister and her two hot friends, I slowly took a longer look at each of them, letting my gaze travel full-length over each girl's body. Janet had a cute little black dress on, not skin-tight, though it clung to her figure in all the right places. It was long enough to prevent charges of public lewdness, but just barely. Up top, her little tits must've been in a push-up bra, since I've never seen that much cleavage on her. Sarah was wearing a slinky red dress that almost looked painted on. The hem was just above her knees, with a slit in the side going almost all the way to her hip. I couldn't see any panty line where the dress clung to her hips and showed off the shape of her ass. The top of it was very low-cut, and with the open back it was clear she was not wearing a bra, and her tits looked like they were about to pop out of the dress. My sister was a stunner as usual. She was wearing a tight, dark blue skirt to mid-thigh that really showed her delightful curves. She was wearing a silvery loose-fitting top that was low-cut with an open back and oversized arm holes so it was clear she also was not wearing a bra, and plenty of side-boob was visible, and even hints of her dark areola as she moved.

"Okay girls, I'll drive you, but I want payment up front. I don't want you changing your minds later because you're too tired or going home with some other guy to get out of your part of the deal," I stated as I stood up, the tent in my pants now very noticeable. The girls gasped slightly when they saw how aroused I was, and I saw my sister lick her lips quickly before speaking.

"We can't do that. You'll fall asleep after, and we won't get to go."

"What about a compromise? Partial payment, the rest after we cruise?" asked Sarah.

"That might be acceptable. Let's figure out the terms," I agreed. We settled on all of us stripping so each of us could see what was waiting for us at the end of the night. As they got undressed, I was able to confirm that only Janet was wearing any undergarments, and only the push-up bra. Mary and Sarah were indeed not wearing bras, and none of the girls wore panties. Janet had shaved or waxed her pussy completely bald. With her petite size, tiny tits, and bald pussy, she looked younger than she was. If I hadn't been to her high school graduation, I wouldn't have known she was over 18. Sarah had also shaved her pussy, though with her figure and more mature face, she could've passed for over 21. My sister just about made me cum without even touching my dick. Her perfect tits seemed to defy gravity, sitting perky on her chest with no sagging or drooping, despite their size. She had cleared all but a little landing strip above her pussy, and with her aroused state, her pussy lips were slightly open, almost inviting me in.

I then got to kiss each of the girls, and not just a quick peck. Each kiss was accompanied by a tits-to-toenails full body hug, and plenty of tongue action. Being naked really ramped up the arousal, and the end of my dick was practically dripping with pre-cum and each girl's pussy was leaking juices down their thighs. The girls then had me lay down while my sister put one of my ties around my head as a blindfold. She reached over me from in front of me, and her tits were dangling in my face as she tied a quick knot to hold it in place. While she did that, I managed to get my mouth around one of her nipples and heard her moan while she finished the tie. I was pushed down onto the bed, and I felt some shifting on and off the bed and footsteps around the bed. As we agreed, the girls randomly chose one of them to hop on and ride me for a little bit, but I wouldn't know which one. My hands were tied to the headboard with two more of my ties, to prevent me from grabbing the girl and figuring out who she was by feeling for what I had just seen. I felt the bed sag on both sides of me, and then a pair of legs outside my own, kneeling on the bed just above my crotch. Apparently all three girls had gotten on the bed to make it harder to guess who it was by the weight of the girl riding me.

I soon felt a hand hold my dick pointing straight up, and a wet pussy touched the head of my cock, before slowly impaling herself and wrapping me in a velvety vice. After a brief pause, she lifted herself off till just the head was still in her, and then she came back down quickly. She repeated this for a few minutes while speeding up, and I felt her freeze and shudder while her pussy went wild around my dick. I heard a muffled scream of ecstasy at the same time that I couldn't hold back anymore and unloaded inside her, firing jet after jet of thick semen into the mystery pussy impaled on my dick. The girls got off the bed, and I heard my sister's voice saying they would be back in a second, they just have to clean up a little.

I heard running water in the bathroom, and what sounded like two more muffled shouts of ecstasy, possibly from the other two girls rubbing themselves or each other to orgasm. I was feeling a little drowsy as I usually do after a good orgasm, when I felt hands releasing my hands and removing the blindfold. The three girls were still naked, and they were smiling in post-orgasmic bliss. I couldn't see any jizz running down anyone's leg, so they must've cleaned that up. Mary was carrying a damp towel, and quickly cleaned the cum and pussy juice off my dick and out of my pubes.

"Okay, let's get dressed and hit the town. We'll be back to finish this up without the blindfold, unless you really want it," my sister said with a wink.