6 comments/ 113425 views/ 78 favorites How I Spent My Summer Vacation Ch. 01 By: BadPup This story is a work a fiction, and the characters are completely fictional. If you are offended by such themes as incest, or graphic sex, or are underage you should avoid reading any further. If you aren't familiar with the story The Man of the House, I'd suggest reading that one first, because it will help you know who all the naked people are at the beginning of this story. I'm planning on this being a multi-chapter story, so new chapters will be going up every one to two weeks. I'd like to thank RMDexter for encouraging me to finish this story and to post it on Literotica. He also provided some of his time for proofreading, and plot suggestions. (If there are any spelling or grammatical errors please be aware they are my fault and not his.) As always, any comments are greatly appreciated, and I hope you enjoy the story. ***** I let the phone call flip over to voice mail. There was no way in hell I was answering the phone right now. I heard the message start. "Hello Robbie, this is Harold, your father." You had to hand it to my old man—he made sure to clarify that, so I wouldn't confuse him with the vast legion of other middle aged men in my life named Harold. "I just want you to know I'll be home on Monday, and I expect my Porsche to be waxed when I get home. Oh, and try to do a better job this time. I found dried wax by the rear wheels the last time I came home. That can damage the car's finish. Jesus Robbie, would it kill you to be even slightly responsible? Also, mow the front and back lawn, and clean out the gutters. You know what? Never mind the yard work. Just try to have the car done right when I get home. We'll start with something simple, and you can work your way to to more complex tasks. I honestly don't understand you,Robbie; there are plenty of boys who would kill to be in your situation." The message clicked off. Well, my dear old dad had that last part right. I'm sure just about every 18 year old boy in America would have killed to be in the situation I was in at that given moment. In fact the situation I was in was so good I hadn't even bothered to open my eyes for my dad's message, I was too busy enjoying some amazing sensations. There was an audible pop from around where my belt buckle should have been, as a pouty pair of lips slipped of the mushroom head of my rock hard prick, and those sweet sensations came to an end. I opened one eye. "I can't believe that fat, little bastard didn't even congratulate you for graduating from high school today." My step-mother Danielle said as she crouched on her knees between my legs, holding my exposed cock in her hand. "I mean how many boys get a full football scholarship to State?" I looked down at my step-mom, a hot 40-something redhead with blonde highlights from the stylist to take out the gray that was creeping in. She was something to look at, with all the right curves in all the right places. The emerald green tank dress she was wearing showed off the miles of deep tanned cleavage of her huge breasts, and the bottom of it just barely skimmed her still amazingly tight ass. "Well I'm sure he's got a lot on his mind," I said with a contented sigh as I stroked her hair. Like I cared about my dad—the bastard had left me and my real mom when I was 13. I hadn't heard from the guy once in five years until he decided he needed me to fill out his little ersatz family earlier this year. "Mmmmm, well he's not half the man you are, baby," my step-mom said with a horny giggle as she slowly worked her tongue up and down the long hard shaft of my cock, like it was the world's juiciest lollipop. "And still I've always admired his taste in women," I said with a smirky grin as I watched my father's wife take first one of my huge over-sized testicles in her mouth, and then the other one. "That guy might know a pretty woman when he sees one, but you're the man who knows what to do with one when you catch her," Danielle said with a saucy wink as she moved up to cover the head of my rock-hard prick with tiny butterfly kisses. "God, I love this big fucking cock!" Danielle announced, and then with a hungry moan shoved my entire cock down her throat. Whatever semi-clever thing I had been planning on saying died on my lips, and was replaced by a low lusty groan. My step-mom was the only woman I had ever met who could deep-throat my cock. A pretty impressive feat when you considered that when my cock was fully erect the tip of the big mushroom head almost touched my sternum. Actually whenever she did this, I couldn't think of anything besides the incredible feeling of having every inch of my dick massaged by her mouth and throat. I vaguely heard the front door open and close, and the click, click, click of high heels walking down our long tile entry hall. "Wow, that looks like fun. Can I play too?" I looked up at my 18-year-old step-sister. Stacy was standing in the doorway of our family room. Stacy was a younger looking version of her mother, with naturally red hair, slightly smaller boobs, and a tighter body than the woman who had brought her into the world. Not surprisingly I didn't have a problem with that, but then again how many men would have a problem with a hot mommy-daughter pair fighting over his cock? Sadly this situation didn't come about as Danielle pulled my cock out of her mouth again. "Now Stacy, you just got a complete makeover for graduation tonight, and you know how much Robbie cums. I don't want your makeup getting messed up before the ceremony," Danielle said as sternly as any mother could say in the middle of sucking off a big teenage cock. "Oh, and you just happen to get Robbie's cock all to yourself? God, you are such a slut!" Stacy said, stomping her foot. "Hey, don't talk to your mother that way!" I found myself snapping, which was kind of ridiculous, because Danielle would be the first to admit she was a slut of biblical proportions. "Keep that shit up, and I will paddle your ass again," I promised my bratty step-sister. "Oh like that will do any good," Danielle teased. "She was moaning like a little whore when you did it the other night." "Mom!" Stacy wailed. "Please, honey, just until we take pictures after the ceremony. You can suck Robbie's cock on the way to the restaurant for dinner," Danielle said, trying to placate her little girl. Then she added something mysterious. "Besides, you want to look your best for Robbie's surprise," she said to her daughter. Stacy stood there balanced up on four inch come-fuck-me pumps weighing what her mom said. Finally after a long while she grunted "Fine," and walked huffily out of the room. "What's this about a surprise?" I asked Danielle who had started rubbing my cock all over her face. "If I told you, then it would stop being a surprise," Danielle said with a giggle. Before I could press her for more details, she began sucking my cock in earnest, hollowing her cheeks out and rapidly moving her head up and down close to half of my cock. I happened to glance up at the clock on the wall. If I was going to make it through my high school graduation without smelling like dirty illicit step-mommy sex, I was going to need to cum in the next few minutes so I could take a shower, and change my clothes. I stood up, my big, well muscled looming over Danielle as she continued to bob her head up and down on my throbbing cock. "Yeah, that's it Mommy, suck that big cock." I snarled at Danielle, but I wasn't able to keep a faint grin off of my face. Danielle looked up at me while my cock slide easily in and out of her plump scarlet lips, her eyes dancing, as she moaned lustily around my cock. Danielle pulled my cock from her mouth and started rubbing over her face. "Yeah baby, Mommy loves this big fucking cock. Give it to me baby, feed Mommy your hot sticky cum. Mommy is so hungry." Danielle had a big grin on her face as she said this, and so did I. This slutty mommy bit was a recent addition to our sex routine. Even though we weren't really related, the whole thing made whatever sex act we were doing, just a bit more depraved and perverted, or as Danielle and I liked to this of it, more fun. Danielle's face was now smeared with my pre-cum and her spit, and I knew just how to treat that sort of a mommy. I pushed my cock back into her mouth and wrapped my big hands around her head. I started pumping my cock in and out of Danielle's greedy mouth. Danielle was easily taking more and more of my cock as I fucked her mouth harder, faster, and deeper. "Yeah, take it Mommy, take it all. Let your big strong son fuck his cock down his mommy's hot throat." Danielle gave me a saucy wink as my cock made her cheeks bulge. My cock was jackhammering her mouth, going so fast and so deep, my big balls were slapping against her chin. Danielle was whimpering and moaning around my big cock, and the vibrations were too much. I could feel my balls start to tighten. "Here it comes Mommy, get ready for your son's cream." I said through gritted teeth trying to hold out just a little bit longer. Danielle moaned even louder, and I winced as her nails dug into my ass to pull me in even closer, so she could get skull fucked with every inch of my big teen aged cock. It was too much I couldn't have held out another second, even if I had wanted to. I felt the cum explode out of the end of my cock and into my step-mother's cum hungry mouth. "Oh Fuck! I'm cumming Mommy!" I grunted as my cock kept spewing my thick potent teen baby batter, which Danielle was gulping down like it was the nectar of the gods. After three or four more ropes of cum flooded Danielle's mouth I was spent, but Danielle kept a tight seal on my cock as she sucked and teased every drop of my seed out of me. Finally when she was sure fun time was over, Danielle let my softening cock slip out from between her bee stung lips. She gave my cock another nasty kiss, and looked up at me. "Did Mommy, make her sexy boy feel better?" She asked me in a breathless whisper. I just grabbed her hair and yanked her head back so I could give her a long hard open mouthed kiss. After a long moment, Danielle pulled away and looked up at me. "Okay baby, time to get dressed for school." Danielle's dirty mommy talk was already getting my cock hard again, but I knew she was right, so I helped her to her feet, so we could get cleaned up for the night's festivities. +++++++++++++++++++++++++++++++++++++++++ We got back from dinner at close to 9:00. Graduation had been nice but utterly forgettable. I got along well enough with everyone at school, but hadn't made any really close friends. Of course, having sluts for a step-mom and a step-sister meant I didn't spend a lot of time interacting with my peers. Anyway, I got a piece of paper that entitled me to make 40% less than a college graduate, shook a few hands, and that part of my life was over. Danielle was as good as her word, and Stacy rode inn the back seat with me to the restaurant, and my cock was out of my pants almost as soon as we cleared the parking lot. Still Danielle was pretty crafty, and must have run a couple of red lights, because before you knew it, we were pulling into the parking lot of the restaurant where we were having dinner before I got a chance to cum. Dinner was pretty much a blur. I'm pretty sure I had a steak, and that I liked it, but aside from that I don't really remember anything about the food of that meal. You see Danielle had arranged for us to get a very private booth in the back with me sitting between my step-sister and her mother. This meant at least one of their hands was running nimbly over my cock, while stocking-clad feet stroked along my legs under the table at all times. Add to that, the fact that they also spent most of the meal whispering the most filthy things into my ear, and well, I'm hoping you can now understand the reason for my incomplete restaurant review. By the time we'd finished dessert and paid the check, my cock felt like it was ready to rip its way out of my pants. We exited the building pretty quickly, and got back into the family sedan. Stacy was riding with me in the back seat again, and I was all over her. Pawing at her breasts, tweaking her nipples and working my big hand into those wispy little panties she was wearing. Stacy was obviously just as horny as her step-brother. That smooth little pussy of hers was like a swamp, and she was moaning like a bitch in heat around my mouth the entire trip home. We did finally make it home, and when the car pulled up into the garage without incident, I was completely ready for sex. I was in a rut, like a wild animal. If Danielle had joined Stacy and me in the backseat of the car I would have been happy. Hell, by that point in the evening I would have fucked those two sexy minxes on the front lawn of our local church. Somehow my two women were able to get me to come inside. Once Danielle mentioned my surprise, Stacy had slithered out from underneath me, and before I knew it, both of them had darted into the house giggling as they went. My cock was so hard and my pants were so tight that it was pretty much impossible for me to walk standing up. I hobbled into the house doubled over like I was looking for loose change along the way. My two sluts were nowhere to be seen. I made it as far as the stairs before Danielle called out to me. "Don't come upstairs, baby. We'll come down for you in just a minute. Just make yourself comfortable in the living room, stud," Danielle yelled down to me. This was followed by more giggling and the sound of footsteps running down to my folks' bedroom. By this point, my curiosity was aroused, and I decided to play along with whatever my girls had planned. I made my way into the living room. I could have got myself a beer. Thanks to Danielle, my favorite kind was in every refrigerator in the house (which my sharp-as-a- tack dad never noticed), but what with graduating and all I decided to be a little more grown up tonight, and poured myself a glass of that good scotch, that as far as I could tell, my dad had only ever offered to the company CEO when he came over to dinner that one night. I didn't and still really don't know the first thing about good scotch, or bad scotch, but I did have enough common sense not to pour it over ice, or cut it with water, or God forbid mix it with coke. This stuff was the real deal, so I poured just a little bit into a tumbler and settled down on the big overstuffed leather sofa. I took a small baby sip. At first there was kind of that bitter mediciny taste which is why I normally avoided hard liquor, but then it tasted, well pretty complex, and that flush of warmth through my chest at the end was an interesting sensation. I realized that once I got past that medicine taste, expensive scotch might be a pretty fun bad habit to pick up. So I was just sitting there, minding my own business and starting to decide that even if I didn't like scotch now I could see myself liking it sometime in the future, when things started to get really good. The lights in my part of the room dimmed, making it like I was in the audience for a floor show. Then some pulsating techno beat started thumping out of our family's surround-sound system, and do you remember how I told you things got really good? Because this was the exact fucking moment that things got really fucking good. My step-mother and step-sister stepped out in front of me in matching slutty schoolgirl outfits. Tiny micro red plaid miniskirts that barely covered their pussies, let alone those two round bottoms of theirs. White halter tops had their firm ripe tits pushed up and on display, and sheer white thigh high stockings to match their tops. Some might have thought the frilly little ankle socks they were wearing would be overkill with the stockings, but those people would be morons. Add to that the fact both women were perched up on what had to be at least five inch black Mary Jane platform shoes, and they were just about the ultimate male fantasy come to life. Actually, the fact that my asshole dad's wife and his stepdaughter were obviously about to do a strip show for me, the ultimate fantasy come to life, and the super slutty outfits were just a bonus. I was so excited that my teeny tiny baby sip of expensive scotch went dribbling all over my shirt. Stacy came strutting into the room first, which made sense. My sister had been cheer leading since junior high, and taking dance classes since pretty much right about the time she started walking. So when it came to the actual dancing part of the night's festivities she was the natural one to do all the spins, kicks, and of course, the splits. Not that Danielle was a terrible dancer, I think she could have made the average stripper think about looking for a new place to work (and that's just on her dancing ability). It's just that Stacy was a great dancer, that's all. They both moved into the center of the room like they owned it, their hips rocking from side to side, and their round firm titties bouncing with each step. When they got in front of me, they did this little sort of dance fight thing that ended with Danielle tearing her daughter's top off of her body, exposing those sweet high-riding tits and Stacy's already pebble-like little nipples to my hungry gaze. Danielle pushed Stacy out in front of her and cupped her daughter's boobs pushing them together, allowing me to inspect the incredible cleavage she had made. Danielle's hands were all over her baby girl's body, rubbing and stroking the teenage girl as she nuzzled and licked at her long graceful neck. Stacy was lost in the bliss of her mother's hands. Her head lolling back, eyes closed, and her hips kept undulating in time to the hard driving beat of the music. Stacy may have been one of the biggest bitches in the history of our high school, a world class bathroom hog, and one of the worst brats I had ever come in contact with in my fairly short life, but at times like this even me, her 18-year-old step-brother, would admit she was one of the hottest little fuck toys to ever walk the face of the Earth. Danielle's hands moved down to her daughter's hips, and she gave me an evil smile as she oh so slowly pulled down the zipper on Stacy's belt-like skirt. Danielle knelt behind her sexy young daughter, still smiling at me and looking me right in the eye, when without warning she yanked Stacy's skirt to the floor, leaving the little teenage slut wearing only a tiny white silk thong, and those big sexy stripper shoes. Stacy didn't really seem to notice what was happening. She was still lost in her own little world, playing with her breasts as her hips went up and down, and around and around. Danielle gave her daughter a firm slap on her delectable heart-shaped ass that I could hear over the loud beat of the music. Stacy opened her eyes and looked at her mother, biting her lip. Danielle gave Stacy a gentle push in my direction, and got up behind her daughter to follow. It looked like we were about to begin the audience participation part of the night's festivities. Stacy walked up to me, turned around and planted her sweet little butt right in the middle of my lap. My hands moved up to wrap around Stacy's hips, but her mom stopped me. "Stripper rules tonight, baby. We touch you, but you can't touch us." She muttered in my ear and then she burst out giggling, "at least for right now, Daddy," I went along with her request. Hell, as horny as I was right then, I would have actually waxed my dad's car if she told me to. My step-sister got the crack of her ass directly over my hard throbbing pants-covered cock and proceeded to grind feverishly against me. "Hi Baby," Danielle whispered in my ear. How I Spent My Summer Vacation Ch. 01 When I turned to Danielle, she had managed to shed her top and my face collided with her oversized tits. Danielle giggled as her fingers slipped into my hair and pulled my face in even deeper. "That's right, baby, show Mommy just how much you like her big boobies." I eagerly complied with her request, licking, sucking, and nibbling over every inch of her chest, but paying special attention to her nipples until they were standing up like hard little rocks. We were like that for a while. Me, nursing on my step-mom's sweet tits, as her daughter, and my step-sister, worked her heart shaped ass in a figure 8 pattern over my cock. Eventually Danielle pulled away, pausing only to kiss me passionately and to push her hot, talented tongue into my mouth before she was gone. She stepped behind Stacy and I couldn't clearly see what she was up to, but it looked like she pulled something out of an inlaid box on the coffee table, and then she peeled off her naughty little schoolgirl skirt. Finally, after what seemed like a long time of her fiddling with her panties, she pulled Stacy out of my lap, and I got my surprise of the night. My step-mother Danielle was wearing a huge strap-on black latex dildo. I felt my jaw drop. I could see Danielle giggle at my reaction. She blew me a kiss, and the next part of the show started. Danielle took Stacy, and gently pushed the young girl to her knees. Danielle pushed that big latex satisfier up into her daughter's face. Stacy played the coy little school girl, and looked up at her mommy with big doe eyes as if to say, "Please, Mommy, no, it's too big." Danielle ignored her daughter's pleading and started to smack that big fake cock up against her daughter's face. After a while Stacy couldn't help but lick her lips. Danielle pulled her horny daughter's mouth up to that big fat dildo and pushed it into daughter's greedy mouth. God it was hot, dirty, and kinky. I tore at my clothes. Danielle may have said I couldn't touch them, but nobody said I couldn't touch myself. In a flash I had shed my shoes and clothes and was fisting my long hard cock as I watched the dirty women in my life perform for me. Stacy's little shy schoolgirl act was long over. She was frantically bobbing her head up and down on that dildo like the hot little cocksucker she was. My step-sister might have only been 18, but she had sucked a legion of cocks during her short time as a sexually active young woman so she knew what to do with a big one. She was getting that dildo nice and wet, as her mom held her head and pumped that fake cock even deeper down her little baby's throat. Finally Danielle pulled Stacy's mouth off of the dildo and pushed her head into my lap. Stacy scrambled for my cock, desperate for the real thing, and engulfed it almost immediately. Danielle crouched behind her daughter, and even though I couldn't see it from where I was sitting I knew the exact moment of penetration. Stacy pulled my cock from her mouth for a moment, and turned back towards Danielle. "Fuck me, Mommy. Fuck your little girl hard," she moaned almost deliriously. I looked at her mom, crouched behind Stacy, Danielle's big tits were bouncing each time she flexed her hips. I could see in my mind's eye that big black dildo slamming into my step-sister's tight little cunt, spearing that hot little pussy, again and again. I grabbed Stacy's head, and pulled her mouth back to my cock. My hips started working, almost on their own. It was like my body had a hot desperate need to fuck my step-sister's mouth as deep and as hard as her hot little snatch was getting worked over. It took me awhile, but soon my strokes were matching Danielle's, and we were spit-roasting that little teenage slut almost without mercy. Not that Stacy was complaining. She had a long shuddering orgasm almost as soon as her mother and I started using her, and when her mother worked that big dildo up into her tight little butt, the horny little slut started cumming buckets. Finally, I needed more. I'd been having my cock sucked all day, but right then I needed to fuck somebody. I slipped out from under Stacy and moved around behind her mother. It took a little prying, but I got that harness Danielle was wearing for the strap-on out of the way, sort of. I wasn't able to get a clear shot at her pussy, but Danielle's hot little butthole was just begging to be pounded. I sank my cock, which was dripping wet thanks to Stacy's talented mouth, into my Danielle's ass with one hard forceful lunge. Most women would have screamed bloody murder if somebody shoved a huge throbbing cock up their ass. Now you could say a lot of things about Danielle, but no one would lump her in with most women. My step-mother just looked back at me and groaned like the wanton whore that she was and said, "Oh yeah Daddy, fuck my slut ass hard." I started taking Danielle's ass with hard deep strokes that actually drove her and that strap-on into her own daughter. It was probably as close as I am ever going to get to fucking two women at the exact same time, which is to say it was pretty fucking awesome. Danielle started moaning and breathing harder as soon as my cock sunk into her butt. She had the stimulation of a big throbbing cock pistoning in and out of her tight little back door, and every time her strap-on bottomed out in Stacy's round ass, that harness she was wearing would rub up against Danielle's hard little clit. She was right on the edge of an orgasm, sobbing, and babbling for "Daddy to plow her bitch ass," but it wasn't until I started pinching and twisting her nipples that she went over the falls. Danielle came with a banshee scream. Thank God we had storm windows, and were on a big lot, or every one of our neighbors would have known my step-mother was getting her ass royally fucked by her teenage step-son and his monster cock. Not that either of us would have cared at that moment. Right then the only thing that mattered was what our bodies were feeling. I didn't give Danielle a second to catch her breath. I knew from experience that if I just keep fucking her hard, she would come again and again, so that's exactly what I did. Danielle's orgasms went off like a long string of fire crackers, and Stacy wasn't out of the picture either. The horny little bitch was rubbing her clit as her mommy kept humping her tight little cheerleader butt, so she was cumming almost as often as her slut mother. For I don't know how long the only sounds in the room were bodies colliding, moans, whimpers, gasps, and the occasional muttered obscenity. It stayed like that until I had fucked the two women I lived with into complete and utter submission. Finally, I couldn't hold out any longer. My balls were throbbing and I knew I was going to unload them. I pulled my cock out of Danielle's now gaping asshole and announced I was ready to cum. Stacy and Danielle disentangled themselves and flew to my cock, licking and stroking it, begging their man to give them all that hot sticky cum. I threw back my head and roared as my cock started going off like a fire hose. That first rope of cum splattered both of their faces, but Danielle being the mom quickly took control. She grabbed my cock and pointed it at her daughter as two more ropes of thick white cum coated her baby's face. Danielle then pointed my cock at herself, letting her face get splattered with my teenage seed, but also directing one rope directly into her mouth (the greedy bitch). Danielle kept jacking and stroking my cock as I came like a fright train, and the stimulation paid off. I covered my step-sister's tits with two thick ropes of jizz that were almost as strong as my first one, and finally to milk out every last drop of my cum, Danielle wrapped her big tits around my cock and slowly fucked it until I was completely drained. I felt lightheaded and collapsed to the floor. Danielle moved my cock from her tits to her mouth, supposedly to clean it, but mainly to keep that big monster hard. Stacy got something to suck on too. She was busy cleaning off her mom's strap-on which had up until moments ago been packed deep in her own little butt. Even before I got my breath back, I could feel my cock getting ready for another go-round. I looked down at Danielle who had her red lips stretched wide around my cock and she gave me a lewd wink to let me know that what had happened was only Round 1. It turned out Danielle was right; we ended up fucking until the sun came up, and now you know how I spent my last day of high school. How I Spent My Summer Vacation Ch. 02 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. How I Spent My Summer Vacation Ch. 02 I reached up, and undid the knot on her halter top. That bit of thin white material fell to the floor, exposing my step-mother's firm tanned tits, and her large mature brown nipples. I reached around her and cupped both breasts from behind, kneading those store bought funbags as I rubbed and teased her rapidly hardening nipples. "Yessssssss," Danielle quietly hissed, as her hand moved up and down the shaft of my cock, pausing only to occasionally rub the pre-cum oozing from my piss hole to help lubricate my big prick. There were some waist-high cabinets built into the side of the wall in the room. I bent Danielle over, so her arms were resting on the cabinets. She knew what was coming next. She spread her long, hot mommy legs, and got up on her toes. I moved the oversized head of my cock up to her pussy. I could feel the heat pouring off of her body. I couldn't help myself. I teased my hungry step-mom by rubbing the mushroom head of my cock in lazy circles around her hungry hole. She moved that wonderful ass of hers in the same lazy circles as my cock for awhile, but eventually her lust won out, and she turned her head back to look at me. "Don't tease me, stud. Give Mommy's cunt what it needs," she whispered with a nasty look in her eye. I smiled at Danielle as I slowly pushed my cock into her dripping pussy, feeling it open up for my long, stiff cock. She closed her eyes and moaned. She was a little loud—I mean considering we were less than 20 feet from her husband. I put a finger up to her lips and mouthed "shush," at her. She nodded that she understood as she slowly kept rocking her hips to work more of my dick up inside her. Usually, when Danielle and I had sex, it was hard, sharp, and noisy. The kind of sex you read about in nasty stories. This sex was different: quiet, and slow, wringing every ounce of pleasure from every movement, but I dare anyone to tell me it was any less nasty. I slowly worked my cock in and out of that tight little middle aged pussy, as she bit her lip to keep from making noise. This went on for a while, the teenaged boy fucking the hot mature woman from behind. We were completely lost in our own world. Right up until my dad turned the TV off. We froze, and looked up with what I am sure were the kind of guilty looks only a stepson and his stepmother can get when they think they are about to get caught in mid-fuck. We could hear my dad moving around in the other room, and for a minute we just stood there, Danielle naked from the waist up, and me with my pants around my ankles and my cock lodged deep in my stepmother's cunt. Finally we heard my dad call out from the bottom of the stairs. "Danielle, I'm going to bed." Danielle and I looked at each other, wondering if we were really going to get away with this. "Danielle, are you coming?" My dad asked in a peeved voice, I guess from being ignored. She got an evil grin on her face. "Soon, Darling, very soon. I just want to finish my phone call with Betty," Danielle said, winking at me. Bringing up Betty was a master stroke on her part. Betty was a friend of hers my dad couldn't stand. I think it had something to do with Betty's nickname for my dad, "that little asshole." To be honest, I always had a soft spot for Betty because of that nickname. Once the B-word entered the conversation, my dad just grunted and started waddling up the stairs. Danielle didn't say anything until she heard my dad close the door to their bedroom. Then she looked me right in the eye, and said, "Okay stud, cum for Mommy. I want to feel a real man's sperm in in my cunt when I'm in bed with your dad." My stepmother may have sucked at monogamy, but that woman could turn a phrase. I did my best to give her what she was asking for. I pushed her head down, and wrapped one of my big arms around her waist, and the other across her tits, as I started to give her pussy the pounding it needed. My big bloated balls slapped against her ass faster and faster as I got ready to whitewash Danielle's married cunt. I was getting ready to cum in my bed too. My breath was getting shorter and shorter as my hand flew up and down my cock faster and faster. Right when I was ready to cum, I noticed that the woman I was fantasizing about no longer look like Danielle. She was shorter, and her ass was definitely more meaty. Her tits were huge, and instead of red hair, this woman had platinum blonde hair. I realized I was thinking about fucking my mom—and that is when my cock exploded. That first big slimy rope of cum felt like it must have gone three feet in the air, before it came down, splattering across my rock-hard abs. Two more bolts of cum followed, drenching my body in my thick white seed. I kept milking my cock as my orgasm rolled over me like a fucking tank. I didn't stop until I stopped seeing stars, and by that time my big teenaged prick had finally started to soften. It felt amazing, it was one of the hardest orgasms I'd ever had. The guilt didn't kick in until I went to get a wash cloth to clean up all that cum dripping off of my body. I'd never thought about my mom that way before, and my relationship with my mom was about the only thing that approached normal and/or pure in my life. Eventually I was able to convince myself it had been a one-time thing, and that people thought about a lot of weird shit right before they came. And yes, I know that was a cheap rationalization, but it was late and I was ready to sleep. I finally drifted off to sleep, but despite my resolve, pictures of my mom kept flashing in my mind. My mom in that fucking sexy dress from earlier in the day. My mom in the various skimpy bikinis that a woman like her would wear on a tropical vacation, and of course, nude. My mom gloriously naked, and ready for hot nasty sex. As I drifted off to sleep I knew that even though I was trying my damndest to be a good son, my already semi-hard cock was proof that my mom was going to be in my dreams that night.