(M)y a(F)fair with a friend's mom--Family Vacation | 2016

So, not only was I good friends with her son and daughter, but she and her husband became fairly close with my parents. We all ended up going on vacation together one summer...to the beach.

I had put the thought out of mind as we drove over to the coast. We could manage to find some sneaky ways to fuck, but knew this situation would be different. The only problem with that idea began as soon as we actually got on the beach. My sunglasses helped hide my eyes as I scanned the girls walking the beach, but it also helped hide me staring at her tits as she'd bend over to get a drink from the cooler, offering everyone a round while she was there, including me as she handed me a beer and shot me a sexy "I want your cock" look that she had perfected with me when we were around others.

It was a couple of days into the trip before something happened. It was after lunch, and everyone was at the beach together when she excused herself to go up to the condo and make a sandwich. I nonchalantly waited a few minutes, then excused myself as well, knowing no one else was up there.

She was at the counter making her sandwich, and looked back at me as I walked in the door. "Just who I was hoping to see," she said. I walked up behind her, cock already hard from imagining what was about to happen on the elevator ride up, and pushed against her. She pushed her ass out a bit, putting her hands on the counter to brace against me, and wiggled against my dick. I started to pull down her one-piece bathing suit, and got her tits out when she stopped me. "Go get your dad's binoculars and make sure everyone is still down there," she told me, and that's exactly what I did. I shouted a head count to her and scurried back to the kitchen, where she still stood, tits out watching my cock move against the fabric of my trunks.

When I got beside her she reached down into my trunks and wrapped her hand around my cock. Looking me in the eyes, she started stroking, telling me how much she had been wanting to feel my cock the last couple days while watching me on the beach. She worked my shorts down and bent over, taking the head of my cock into her mouth, stroking the shaft and licking and sucking over the tip. I reached down and grabbed a handful of her tit, then started twisting and pulling one nipple, then the other, and both. It wasn't long before I had to get inside of her, and she knew. She stood up and turned around, leaning against the counter again while I pulled her bathing suit down. I went to the floor with it, looking up to see her pussy inches from my face. I leaned in and gave a long lick from clit to hole between her pussy lips, smelling ocean and pussy mix together. I stood up and lined my cock up, feeling her reach down between her legs and take me, rubbing me against her wetness, then guiding the head of my cock into her pussy. I pushed in slow, and held it there, then gave a couple of steady pumps before picking it up. Soon I was fucking her hard, the sound of our skin smacking together filling the tiled floor living room/kitchen area, with the faint sound of her wet pussy taking my cock mixed in there somewhere. I was ready to cum quick, and pulled her by the tits so she was up against me, asking her in her ear where she wanted it. "Pussy," was all she said. I immediately went into overdrive, thrusting in hard as I felt my cum release into her. I held her against me by the hips, not moving as my cum streamed into her.

Once I was done I popped my cock out and backed away. She pulled her suit up and went to the bathroom to clean up, and I pulled up mine and pushed my hard cock down so it was slightly less noticeable, and sat out on the balcony. Within minutes my little cousin came running in the door with her friend, looking for something to eat. She came out of the bathroom, and was talking to the girls as I said hey and that I was going back to the beach. The girls ignored me, but she looked at me and smiled that same, "I want your cock" smile.

LATER in the week: it wasn't necessarily planned, but late one night, we found ourselves on the balcony of the condo with everyone else asleep inside. The curtains were drawn since the moon was full, so we were concealed out there listening to the waves crash and watching the moon shine. She had a leg kicked up as she sat in a chair next to me. We were making small talk when I looked down and noticed her shorts loosely hanging to the side, and her bare pussy showing clearly in the moonlight. She smiled at me and said she couldn't believe I fucked her on the family vacation. I followed up with something like, "Play your cards right and it won't be the only time," to which she quickly reached over to see if my cock was already hard (it was, of course). I pulled my shorts down a bit and let my dick pop out for her to stroke, as I reached over with my near hand and started rubbing her clit. Her breathing deepened, and she would stroke me harder as she breathed heavier, slowing as I slowed. I asked her to take one of her tits out for me, and she obeyed, letting me lean over and suck the nipple, biting on it and flicking my tongue over and across it.

After so long it became obvious that I had to get inside of her, so we devised a plan where she would go inside, slipping into the bathroom quietly, and I would wait a couple minutes and go in, acting like I'm going the bathroom. I was so hard creeping through the darkness, stepping over friends and family that slept on pallets in the living room, thinking about nothing but the pussy I was about to be inside of, the wetness I going to feel all around my cock.

I stepped into the bathroom and she closed and locked the door behind me, then walked up to me and pulled my shorts down, getting on her knees as she started slowly sucking my cock the full length in and back out to the tip, lick it, and back down. I pulled out her tits and pulled on her nipples, pushing her head down on my cock now and then, but I couldn't take it long. I pulled out of her mouth and she stood up, bent over the sink so we could see each other in the mirror. I reach around and started rubbing her clit, causing her to jut her ass out. I parted her lips and watched my cock slowly disappear into her wet pussy. She let me pump into her a few times before she caught my eye in the mirror and told me she wanted me to fuck her ass. I pulled out my cock, using her pussy juice to lube her asshole with my finger. I pushed the head of my cock against her hole and tried to gently pop it in. It didn't take much, and soon I was halfway inside of her and pushing. After a couple minutes she was comfortable and I started thrusting, harder and harder. She looked me in the eyes in the mirror, her tits pushed out with my hand on one and hers on another, telling me to cum in her ass. I was so incredibly turned on, and would do whatever she told me to anyway, so I started fucking her faster and faster, forgetting about the noise and just pumping into her until I felt it rising. I looked at her and told her here it comes, and starting pumping my warm jizz into her ass. She closed her eyes and tried not to moan, smiling as she gave a little shimmy, me tugging her nipples one last time before popping out of her ass.

We cleaned up and went to bed. I woke up later than everyone else the next morning, needing the sleep and hoping I might find her alone in the condo with everyone else at the beach. Alas, those were our only two times in the family vacation, but we made them count.

Anyone else have good vacation stories/other stories this reminds you of? PM me :)