risk-e-venture:Prom DatesIt all happened so fast… My whole family moved to a new town right
risk-e-venture: Prom DatesIt all happened so fast… My whole family moved to a new town right in the middle of the school year, and all of a sudden, I went from knowing everyone, to knowing nobody. At my new school, I made one or two new friends; but they were all guys, and the prom was just around the corner. It sucked, because at my old school, there were several girls that would have gone with me, and I would have gotten lucky too; but now…I was telling one of my new buddies this when he confessed to me that he found his date on a local hook-up site, and he suggested that I do the same. He linked me the web address, and, sure enough, I managed to secure a blind date of my own with a woman who promised to be flirty, wild, and fun. In the end, my buddy and I agreed to go halves on a car, and a hotel room. Quite frankly, we couldn’t afford two rooms, and when we told the girls, they teased us for thinking a lot of ourselves. They joked that we were getting a little ahead of ourselves in assuming that the night would end at a hotel… but then they both agreed, and it seemed like I had gone from having no one I knew, to having only 1 good friend, to having a date who was basically promising to have sex with me after spending the night at prom; and all in the course of a week or two. Things moved, SO fast. Then the big night came, and my date was gorgeous. Unfortunately, my friends date was both really hot… and my mom. I had met my date for dinner before hand, so when they picked us up in the car to go to the actual dance, mom was already sitting in the car with my new best friend, with her hand sitting on his lap. Her hair was the new darker shade that she adopted when our family moved her, and she was using the new accent she had been cultivating; but it was her. Needless to say, it was awkward as hell at first. But I sure as hell didn’t want to ruin my date by pointing out the taboo, or my new friendship by pointing out what was going on, and mom was apparently having similar thoughts. So, we exchanged a nervous, searching look, and then, after a minute, we both just kind of smiled, laughed, and then went about our night like nothing had happened. It was kind of fun actually. My date was a great time, and it was sort of surreal to see mom in a date setting. Making things even more interesting was the fact that, ever since we moved, mom had been trying to ditch her accent. Her family had some southern roots, and she’d always had a bit of southern drawl. Growing up all the local kids thought it was sexy as hell, but mom thought it was embarrassing after we moved. She called it her “dirty voice” because she didn’t like how it made her stand out. So, ever since we moved, she’d be trying to shake it. So, that whole night, mom used her new voice and accent, trying to sound like a sort-or upper crust business woman. Honestly she was succeeding, it was just kind of weird because when it was all put together it was like she was a totally different person. So, needless to say, I have no fucking foresight whatsoever. Because it wasn’t until hours later, when, a little buzzed from spiked punch, and happy as hell from, just a great fucking time, I headed back to the car with my date, and found my friend and his date already there. At first, it was just more of the fun from before. My date and I were kissing, she was seriously hot, and the car was driving to the hotel, but as her hand slid up my thigh and grabbed my crotch, I realized… we were driving to the hotel. Not just me and my date… but all four of us. Then was the first time I peeled my eyes off of my date, the little white top of hers that just kept sliding lower, and lower, and over to my friend and his “date”. I’d heard stories growing up about my mom “getting down on the farm”, but they were all told by adults in my general vicinity, and I never really had any context or details. Until now. My buddy had taken off his tux and tossed it into the row of seats behind him. His pants… were down around his ankles. His date had been wearing a short and low-cut dress to begin with. But seated across from me, it had been hiked up so far she may as well have not been wearing one. A single strap had slid down her shoulder to the elbow, and enough material had been pulled down that her tits now hung out in the open air. My buddy’s arm was around her, and had a big handful of one of her tits. It was the first time I had seen mom topless since I was a baby. He squeezed it and kneaded one of my mother’s large, beautiful tits as I watched, and my reaction was… very adult. The his dates hand reached over and, with long, painted white fingernails, began to stroke up and down the length of his cock. He was moaning, and saying things like “fuck yeah”, and “that feels so good babe”, and of course, he kept using my mom’s first name while he did it. But as I watched, transfixed, and my own date began to slide my pants down, so we could “join in”, I realized that my staring had not gone unnoticed. I looked up at my mom, while she was stroking off my best friend and her tits were being played with, and she looked right back at me, and, with a handful of teenaged dick, she gave me a playful wink. You would have thought, for just a second, that we were playing some kind of strange game. But then she leaned forward, licked her lips, and with a moan said, “mmmm…. Mommy’s hungry”. Then she turned her head, and my mother’s sweet, full lips wrapped themselves around the head of my friend’s dick. As my mom was stuffing the bloated purple head of my friend’s dick into her mouth, my own date slid down to her knees, just off to my side, and shot my mom a look. I honestly thought the gig was up and something terrible was about to happen when she gave my mom, who was still blowing my buddy, a huge and sinful smile. “You nasty little slut!” she exclaimed with a laugh, her tone obviously playful. “I Love It!”. Then my date turned to me and with her hand wrapped around my shaft, and her red lips moving ever closer to it she asked, “So, how about it my little teenaged stud? You game too?” I was so horny, and so turned on, and so torn and confused, and I had no fucking idea what she was talking about! It must have shown in my face, because she gave another wicked little laugh. “I mean…” she started to say, but then she paused and leaned forward to give the head of my cock a teasing little lick before looking back up at me. Then, in the purest, most caring, most maternal voice that she could manage, she asked me, “do you want to stuff your big cock down your mommy’s throat?” And a split second later, she wrapped her lips around the head of my cock, and in a long, painfully slow motion, she began to moan, and slide my cock along her tongue, to the back of her mouth, and then all the way down her throat. I looked over at my mom who was looking at me with wide eyes, and as I watched her suck of my buddy. Right in that moment I lost it. I grabbed my dates hair, and fucked my “Mommy’s” pretty little face until I came down her throat. Of course while I was doing that, so was my friend… Later, at the hotel, we learned that there had been a mix-up and that our room had one bed instead of two, but our dates not only didn’t seem to mind, they were both into it. We went upstairs and talked, and made out, and danced, and had a little more to drink. It turned out that my friend had found mom on the dating site by looking for people with similar fetishes, and he had actually been seeking someone who would “play mommy” for him. We then figured out that since it was my buddy who linked me the invite to the site, that it had paired me with similar matches, and so we both ended up with older women with incest fantasies. Of course, as he said it, I shot my mom a look and she had the decency to blush and look away. As the night rolled on, things only got more daring. Mom’s refined voice slipped more and more as her “dirty voice” made more frequent appearances. Little touches of her famously sexy southern drawl, kept slipping out as the night wore on. We made out with our dates, getting gropey as hell, and I tried not to stare at my mom getting fondled by a high school buddy. The girls both made out with each other when, like a couple of high school boneheads, we asked them too. But they insisted that we let them pretend to be our mom’s while they did it, and they got more than a little heated as we let them play out, what we now knew, was one of their biggest fantasies. My friend actually came again, just jerking off as he watched our dates gently lapping at one another, and occasionally glancing at to spare some teasing dialogue, like, “do you like that son”, or “don’t look baby, mommy shouldn’t be doing this”. But then later, when it was time for bed and we all looked to the looming king size mattress, my date said “you know, you could be brothers… or something”. She said it so coyly, and yet so suggestively. But my buddy and I just kind of glanced at one another confused, not really seeing how that was a sex thing, and our confusion made the girls laugh again. A moment later, my mom walked up to me and grabbed me by the shirt. She pulled me over towards the bed, and pushed me down onto it, then she began to crawl towards me, and I found myself scooting back until she caught my leg with one hand, and pulled my underwear down and off, leaving me in nothing but my t-shirt. Then, she looked back over her shoulder and signaled for my buddy. The only thing she was still wearing was a pair of white stockings that she had brought special for the hotel room.I could feel an intense heat rising up in my chest and filling me, and my heart was starting to hammer a little faster. I still didn’t know what was going on, but it was already incredibly intense. Then, as my friend walked up behind her, mom turned back to me and crawled closer, but this time, her rather large tits fell on either side of my cock. She reached down with one hand, and very gently wrapped it around my hard-on, touching me for the first time. Then she pulled my hard up up into her cleavage, and snuggling it into position there. As my friend got on the bed behind her, her tits rocked and stroked both sides of my cock against the soft flesh of her breasts forcing a small moan from me. He commented that he loved “that Georgia peach thing that she did”, referring to mom’s slipping accent, as he tapped the head of his cock into position. I wanted to tell my friend no, that he was going too far, that that was my real mom… But then mom took my chin in her hand, a loving and familiar gesture, and lifted my eyes to hers. All pretense of her new accent fell away then. Her slow southern accent was rich, sweet, and singularly familiar. If her new lover like it, then she would use her “dirty voice” for the rest of the night. Then, with what was both the sexiest and the most familiar voice I had ever known, she said “What your date means sweetie, is that we all seem to be kinkier than we originally let on, and well…” The bed rocked a little more, and she bit her lip for a moment, looking like she was being sexually pleased as her tits stroked my cock a little more. I heard my buddy let out a small moan of his own, and what sounded like him saying “so tight”. After the moment had passed, mom’s eyes fluttered back open, and she made sure she was looking right into my eyes. I vaguely understood that my buddy was settled inside of her, his dick stretching her pussy open; when she said, “I don’t know how else to say this slugger… Do you want to get sucked off by your mom while one of your little friends slams his cock into her from behind?” Then there was a quick violent movement behind her, and mom jerked forward, her tits sliding up the length of my cock as a cock invaded deeper into her pussy and forced a moan from her. She looked up at me with her mouth open, and her eyes filled with pleasure, as her body began to rock, and buck, and jerk with from the fucking she was getting. Her tits were stroking me off, my date was masturbating in the corner, and I was watching in the hotel mirror as my friends dick slid into my mother’s pussy and made her moan. His balls started slapping up against her, her tits were rocking, my dick kept sliding up the line of her cleavage and popping out from between her tits; and just when I thought it couldn’t get any hotter she looked back up at me and moaned “Oh god baby! He’s fuckin’ your momma!” Then she turned her face back towards the bed and in one smooth gesture, she slid the full length of my cock down her throat. Even though I had already cum once, and he had already cum twice, we still didn’t last but 10 minutes after that point. Mom bucked, and slid, and moaned, and occasionally freed up her mouth to spout some nasty encouragement. Until finally my friend started saying that he was so close, and asking where he should cum. That was when mom took me out of her mouth long enough to tell him to “go balls deep sugar! You just dump that load in momma’s womb and let me worry about the rest hun!”. That set me over the edge, and forcibly grabbed her by her hair, shoved my cock down her throat, and started fucking her face. She obviously didn’t mine either, because a few second later we were all screaming and cumming and moaning. Even my date in the corner joined in, her fingers a blur as she screamed and came right along with us. It didn’t even end there. We fucked for hours. Changing partners and tag teaming our “moms”. But once again, I had no thought for the consequences, and no thoughts of the future until it was too late. As we were leaving the next day, and the girls grabbed a cab together, my friend came over to me and told me that his date had made one last proposal before she left. She had asked him if he liked the roleplays, and when he said yes, she slipped him a piece of paper with her address on it. She told him that if he thought the incest was hot, he should bring 5 or 6 friends over next Saturday, and she would let him watch while his sweet southern “momma”, get “defiled”. “Isn’t that fucking hot?!?” he asked me, obviously exited and going to take her up on the offer.But I knew there was more to it than that. Because her address was MY house. All my new friends, were the friends he was going to invite. So basically, every friend I had was going to walk into the house of a busty milf, thinking they were going to engage in some hot, nasty, role play. Then they would walk passed the dozens of pictures of me growing up, of my parents, and more specifically, my mom, raising me from a baby, to a teenager. They would see her smiling face as she raised her little boy. They would know, for a fact, that she was my real mother, and that they were looking at my mother’s smile… and then they would ask her to wrap that beautiful smile around their teenaged hard-ons… and she would. She actually would! “Oh my god”, I thought. They are going to gangbang my mom… But then I realized that my friend was inviting me, and that, whether I accepted or not, Saturday was my day off too. So, I realized the truth. It wasn’t “them”, it was “us”. There were only so many options now. So few choices were left. I could be in my room playing a video game this Saturday, trying to pretend that I didn’t hear a half dozen friends as they spent the day loudly fucking my mother’s every hole. Or, I could play along with the fantasy she proposed. I could hang back, and watch them. Forced to watch my real, “sweet southern mamma” get “defiled” by high school boys, as they used her body in every room in the house; maybe even on my own bed. Or… I was going to join in. But not matter what, I would see those guys at school two days later, and every day after that; and we would know. One thing was certain, no matter what happened from this point forward, my life at home, my life at school, and my life in our new town, was never going to be the same. -- source link