How I Spent My Summer Vacation

All characters in this story are completely fictional, and over the age of 18. If you are bothered by subjects like incest, or infidelity, or descriptions of graphic sexual encounters, this isn't the story for you and you should stop reading now.

This story is the second part of a multi-chapter story called How I Spent My Summer Vacation, so if you have not read the first chapter, you might want to do so now. This story is a continuation of a story called The Man of the House, and if you have not read that story yet, you might want to take a look at it too.

I greatly appreciate any feedback on my stories, so any comments on the story are always great to read. (okay, I appreciate the positive comments more that the negative comments, but either type is fine)

Thanks again to RM Dexter for getting me writing again, and for all his input and suggestions.

*****

After a long night of hot dirty sex with my MILF of a stepmother and my slut cheerleader stepsister you probably would have thought that I would have spent the next day sleeping in and maybe replenishing my precious vital bodily fluids, but actually I staggered out of bed at about six thirty, and had a taxi take me to the airport.

I did this because I was leaving to spend a two week vacation with my mom. This meant that I never got a chance to wax my dad's car for him. The one drawback of written stories is that you can't see that I was wearing my totally-doesn't-give-a-shit face when I wrote that last sentence.

Actually, even though I was dead tired when I got on the plane, I was in a great mood. After ten months away from her, I was going to get to spend two weeks with my mom. I know, pretty great, but it gets better. About six months ago my mom landed a really good job that paid a lot more money than her old job, so my mom had decided we were going to go on vacation together at some swanky resort in the Caribbean.

This was extra special for my mom, because this would be our first vacation as a family together. When my dad was around there was never time to go on vacation, because he was always working, or going to school, or probably banging barely legal strippers. After he left my mom, we barely had enough money for rent and groceries, let alone trips. Mom said this vacation was something she had wanted to give to me for a very long time.

The place sounded great. It was all secluded bungalows, centered around what looked from the pictures mom sent me to be a pretty awesome pool. There was a private beach, a gym, a day spa, a couple of bars, and a pretty spectacular restaurant, and well, you get the idea. The place sounded better than anywhere I'd ever been.

Not that it mattered to me. I was just excited to see my mom again. My whole life, she was always my best friend, and I always knew no matter what, that we would be there for each other. If that makes me a mama's boy then I don't have a problem with it.

Getting off the plane down there I realized that my sex life was about to take a complete nose dive. I mean I was going to be with my mom, and even if I found someone to hook up with, I was guessing that getting some private time where what I was doing wouldn't be painfully obvious to my mom might be a little tricky. Not that it mattered that much. It was only two weeks. I could survive, besides it might be fun to be a normal teenager for a while.

I looked for my mom when I got into the terminal but didn't see her. She had come down on an earlier flight and we were going to take a cab to the resort together. "She must be in the bathroom," I thought to myself as I walked over to pick up my luggage.

As I walked across the terminal, I couldn't help but notice the hot older woman standing by the luggage carousel. I'm sure she was probably an average sized woman, but the high heels she was wearing probably had her close to 5'10". They were borderline come-fuck-me pumps, much more appropriate for a nightclub then an airport terminal. Still they kind of went with the short little polka dot sundress she was wearing, and they really helped to show off the woman's long tanned legs.

I couldn't see what her face looked like—she was wearing a sun hat with those big black sunglasses that seemed to be in style for women at the time. Not that I would have been looking at her face. Her tits had my complete attention.

Look, just so you know, I don't routinely refer to all women's breasts as tits. Okay, as you've seen from me talking about Danielle, Stacy, and any other women I happen to be fucking, I refer to their breasts as tits, and yes, I am very aware that even in the best of situations, that is a slightly fucked-up attitude. Still, I did live with my mom for 18 years and try not to think and act like a typical male horndog with every woman walking the face of the planet.

That being said, the woman in the polka dot sundress didn't have breasts—she had what might have been the biggest, ripest set of tits I'd ever seen. They were almost too big for her frame, threatening to spill out over the sides of her chest. I was sure they were fake. 20 year-olds didn't have tits that rode that high, and were that firm, and while this woman didn't look old enough to be one of those 20-year-old's mother, she could very easily be a younger aunt.

It didn't hurt matters that the sundress she was wearing had a scooped neck that put all that cleavage on display for every man in the airport to lust after. My dick started pushing its way down the leg of my pants, and I'm sure I wasn't the only guy in the airport who was dealing with that situation. That woman was built to be fucked.

That woman was something else all right. Not that I was in a position to do anything about it. I just filed away a mental image for masturbating to sometime over the next couple of days and kept walking to the luggage carousel which was beginning to spit out suitcases. I started watching the bags waiting for mine to come up.

"Robbie?" I heard a voice behind me. Well it wasn't just any voice, it was my mom's. I turned around, anxious to see my mom in the flesh for the first time in almost a year.

The only thing was that my mom wasn't behind me. It was that hot older woman. I was looking behind her for my mom when she took off her sunglasses.

"Mom?" I asked in disbelief. The eyes and smile were definitely my mom's, but I had never seen that body before. What the hell happened while I was gone?

Mom threw herself at me and wrapped her arms around me. Those big tits were pressed up against me, and the smell of her perfume was intoxicating. I had to stop myself from grabbing that meaty ass of hers.

Mom kissed me too, but it wasn't like any kiss we had ever had. Those plump ripe lips of hers were pressed up against mine in a ripe opened-mouth kiss. It was almost like she was begging me to slide my tongue in her mouth, or to slip hers into mine.

Mom eventually broke our kiss so she could nuzzle my neck. I swear to God I didn't do it on purpose, but my cock was inching its way down my jeans, and with her body pressed up against mine, mom just had to know.

"God, Baby, I've missed you so much," she cooed in a breathy little voice I'd never heard my mom use before. She looked at me with a playful smile that I actually could remember from my childhood. "Well, we can't stand here all night. Your flight got in so late, and we still need to check in at the hotel."

"Yeah, sorry Mom, but my flight got delayed in Miami for four hours," I said, grimacing. Not having flown a lot at this point in my life, I thought a flight delay was out of the ordinary.

"Oh, it's not your fault, Robbie, but get your bag. You have no idea what your mother had to do to get us a cab to take us to the hotel," Mom said with a giggle.

I was so stunned by this whole situation, that what my mom had just said didn't sink in until I was picking up my bag. Given how my mom was dressed, and how she was acting, an image formed in my mind of my mother sucking some strange guy's dick. Needless to say, this mental picture didn't do a thing for getting my cock to go down. As soon as I had my suitcase, Mom took my arm and we walked out of the airport to the waiting cab.

Almost as soon as the door was closed, Mom was snuggled up against me, her big breasts pressed up against my chest, and her leg thrown over mine. That sundress rode up so far you could almost see her panties—assuming she was wearing any panties. An evil little voice in my head was betting my mom's naked pussy was covered by just a couple of inches of dress fabric.

Like I said, my mom was pressed right up against my body, her leg right up against my cock. Jesus, she had to know I was hard as a rock, but she just kept nuzzling my neck and telling me how much she had missed me.

For some reason I happened to glance up and saw the cab driver's eyes in the rear view mirror. He was trying to look up my mom's skirt. Get a panty shot, maybe more if she wasn't wearing panties. Without even thinking about it I put my hand on her bare thigh, and felt my mom shiver at my touch. The cab driver's eyes looked up and met mine. My eyes narrowed and his hastily darted away. There wouldn't be any more peeking for the rest of the trip. Still, for some reason I didn't take my hand off my mom's thigh. I don't know why, but it just felt right there.

We got to the hotel and got checked in without too much fuss. The guy behind the counter did make sure my mom and I put on some green wristbands, but aside from that we got settled into our suite without any complications.

Now I don't know anything about hotel suites, but I was pretty impressed by this one. A big sitting room with an overstuffed leather sofa, a couple of comfortable chairs, and for some reason, a surprising number of ottomans. There was a huge flat-screen TV on the wall, and a killer sound system. My room was almost as big as Dad and Danielle's back home, and I'd been to parties in places smaller than my mom's room. The only thing weird thing I noticed about the suite was there were a ton of mirrors in it, on the walls, the ceilings, everywhere. But aside from that one oddity, it was definitely the swankiest place I had ever stayed in at that point in my life.

The suite also had a small breakfast nook, with a table and two chairs that were perfect for room service, which is what my mom and I had for dinner that night. While I had settled

into my room, my mom had ordered us cheeseburgers, and before I knew it, I was sitting down to a big grilled burger with a huge side of fries.

Mom fussed around with my plate. She made sure I had ketchup for my fries, and my burger was exactly the way I liked it. It was just like old times. Of course those four inch heels and the huge breasts were new, and my God, when did my mom dye her hair platinum blonde?

"What do you think of my new look, Baby?" Mom asked me, almost as if she was reading my mind. "Is your mommy pretty?"

"You've always been pretty, Mom," I said, and it was pretty much true. When you're a little kid, your mom is the prettiest woman in the world. The only thing is as you get older, your mom turns into, well, a mom, and my mom was no different. Right up until now—now my mom was different as hell, and my cock really seemed to like it.

"So you don't like how your old mother looks?" Mom mock pouted, with a long sigh.

I couldn't help myself, my eyes were glued to her cleavage when she inhaled. In that tight dress she was wearing, it was a tit man's wet dream.

"God no, Mom". I heard myself say without thinking. "You look hot." Oh shit, did I just tell my own mother she was hot? Sons weren't supposed to tell their mothers they were hot. Hell, sons weren't supposed to think their mothers were hot. I quickly tried to backtrack.

"I mean you look great, Mom," I said, going with the more socially acceptable compliment.

Mom beamed back at me. "I think I like hot better. Nice to know an old broad can get a young guy's attention."

"You've always had my attention, Mom. You're my best girl, remember?" I said, bringing up the nickname I had for my mom since I started high school. It had always made her smile when I called her that, and it worked here too.

"Aw, thank you, Sweetie, you always know how to make me happy."

"So, what happened?" I asked. I was more than curious to know how and when this change had happened.

"Well, you did, Baby," my mom said with a little grin, and then went on to elaborate. "When you left to live with your father, I was on my own and only working three days a week. I had nothing else to do, so I joined a gym and started working out."

"Wow, Mom, you did that all by yourself?" I asked, impressed by the results sitting across the table from me.

"For the first month, Baby, then I met Derrick, my personal trainer. Now that young man knows how to put an older girl through her paces."

I pictured a guy my age, who kind of looked like me, putting his hands all over my mom as she worked out. I noticed my cock was starting to get hard again. This was when my mom dropped the bombshell of the night.

"I worked out with Derick for a couple of months until I got everything tight, and then decided to spring for the sluts."

Huh, what, who? My jaw must have hit the table because my mom went on to explain that last part to me.

"The sluts are what I call these," my mom said, cupping her breasts and giving them a playful hoist. "Some women have girls, or twins—I have sluts," she said with a playful giggle, like it was the cutest joke in the world. "What do you think of them, Baby?"

"Uh, they're great, Mom," I said, feeling a flush creep up my neck. I'm sorry there is no way to discuss your mom's tits with her, and not feel like a perv.

"Oh thank you, Robbie. Steve thought they might be too big for my frame." Mom must have noticed that I wasn't really tracking on that last sentence, because she clarified it. "Steve is my plastic surgeon."

My mom was my den mother in Cub Scouts, and now she not only had a plastic surgeon, but they were on a first name basis? This was getting more bizarre by the second.

"Steve told me I wanted stripper tits. These aren't too big, are they, Robbie?"

Did somebody say my mom looked like a stripper? Well, she had the body of one. Hell, most porn stars didn't have the body my mom did now. Then I looked at my mom's face and knew that she didn't look like a stripper. Most strippers, even the young ones, looked hard, and my mom with her sweet smile and kind loving eyes looked like, well, my mom.

"They look great, Mom," I said, smiling back at her, "and if they make you happy, then they make me happy."

"Oh Robbie, you're the best son in the world."

"Yeah," I said with a little half grin, "I know."

My mom and I both had a good laugh, and then she started asking me about my plans for college in the fall, and just like that, we went back to being a normal family.

+++++++++++++++++++++++++++++++.

After our dinner, we turned in. It had been a long day, and we were both pretty wiped out. Still I had a hard time getting to sleep. I was antsy, and just couldn't seem to nod off. Eventually I decided to masturbate—that would settle me down.

I slid my hand inside my underwear and started to rub my cock as I thought of something to inspire a quick, hot, sticky orgasm. I settled on a little adventure I'd had with Danielle about two weeks before.

It was a school night, and I'd gotten home late from studying at the library. My dad was home that night in the living room watching his favorite show. It was some show where people brought old things from their garages and attics, so appraisers could tell them how much they were worth. My dad was watching this on a 72 inch flat-screen TV. Sometimes I think the only reason my old man exists is to prove you don't have to be that smart to be rich in this country.

Anyway, my dad took time out of this to interact with me, his only child. He decided to give me a ration of shit about me taking the car to go hang out with my friends at the mall. Please keep in mind that at this point my dad knew I had a 3.8 GPA, and that in the last year there had been several stories on the local news about how since everybody bought everything online now that the mall had been pretty much abandoned and taken over by a colony of angry squirrels.

None of this mattered. The whole point of this little conversation was for my dad to remind me it was his house, and his rules. I was able to get this point, because as my dad cleverly told me; "My house, Robbie, my rules."

I told him sure thing, Pops, and I could tell he didn't like being called "Pops", which was the main reason I did it, but he let me go because on his show they were about to find out how much this three-foot-tall ceramic cat was worth.

I walked away from my dad, but on my way out of our giant living room, I saw Danielle sitting in a small room playing on her phone. She looked up, blew me a kiss, and motioned for me to join her.

I glanced back at my dad. I was behind him, so he couldn't see me. I quietly slid into the room to see what his wife wanted me for.

As I walked up to Danielle, in one smooth motion she put down her phone, and ran her French manicured nails up the front of my pants.

"Hi Daddy," Danielle said, coyly licking her lips.

I looked down at my horny stepmother, her perfect red hair, that perfect white halter top that was only there to draw attention to her big, tanned breasts. The little white tennis skirt, that while being way too short for actual tennis, was just the right size to give any teenage boy an erection you could cut a diamond with, her long smooth legs that seemed to go on for miles, and all that perched on a pair of lavender four inch pumps. I took in that amazing view, and my run in with my dad was completely forgotten.

I pushed one of my fingers past Danielle's scarlet shaded lips. She blissfully closed her eyes, and sucked my finger like it was the sweetest treat in the world. I slid another finger in besides the first, stretching her mouth a little wider. She took it like a champ, and just looked up at me, with doe eyes, almost managing to look innocent as she pretended to suck a cock, and massaged my real one in my pants.

Speaking of my cock, it was hard as steel now, thanks to Danielle's skillful fingers, and the sight of her acting like the hot middle-aged slut wife we both knew her to be.

Danielle undid my belt with her free hand, and undid the button on my jeans. She purposely took her time pulling down my zipper, the click of each link being freed seemed like the loudest sound in the world.

When she finally pulled my underwear down, and my cock slapped against my stomach, it was ready for anything, that big blue vein that ran down the shaft almost seemed to be pulsing, because so much blood had flooded into my hard teenaged mommy-fucker. She wrapped her hand around it, her long sensuous fingers barely able to wrap around the shaft, and started to slowly, and shamelessly, jack her stepson's big throbbing prick.

It would have been so easy then just to have my rod take my fingers place in her mouth, and I suppose that maybe if I hadn't woken up that morning to find my stepmother in my bed wearing a wispy red teddy, and greedily bobbing her head on my cock, that would have been enough to satisfy me. But it wasn't. This was one of those times when a young man needs the satisfaction he can only find in a hot mature woman's pussy.

I quietly closed the door to the room, so as not to disturb my father watching his TV show, and then gently pulled his wife to her feet. Danielle smiled at me; she knew what was coming next.

I positioned her in front of me, and began nuzzling her neck, my big hands roaming all over her tight sexy body. She leaned back, melting into my caresses, giving herself over to whatever I wanted to do with her.