24 comments/ 152664 views/ 202 favorites Stepmom Needs Help By: TxAuthor All characters are over 18 ***** "Tommy!" I heard my name and woke with a start. I sat upright in bed, my heart racing, my ears straining to discern if what I heard was real, or a dream. I heard my name a second time, and I dashed out of bed and down the hall. It was my stepmom, Carrie, and she sounded in distress. "Carrie?" I asked through her door. "Tom," she said, her voice quiet. "I, um, I need some help." "Okay," I said, testing the doorknob. "It's locked." "I know," she said, her voice transmitting her distress. "Can you grab your tools and try to open it?" I told her I'd be back. It was odd that she needed my help to get out of a locked room, from the inside. Carrie married my dad when I was ten, and when he passed away three years later she was the only family I had left. We were very close, sharing everything. My mother had passed away when I was a baby, so I never really had a mother figure in my life. Carrie, from the start, had always been more like a friend, a confidant, rather than a mother. I was 22 and finishing my college degree. It may seem a little sad to still be living at home at that age but I was saving money and helping Carrie around the house. Besides, I didn't have a girlfriend, so it's not like living with my stepmom was hurting my chances. She had also been single since my dad died. "Alright," I said, returning to the door. "It will take a second to pop the lock open." "Okay," she said, sounding somewhat relieved. "But that's only part of the problem." "I'm all ears," I said, fishing for the smallest screwdriver. It was an older lock, with a small hole in the center of the knob. A good push on the pin behind that hole and the door would be open. Easy. "Well, I..." she said, pausing. "I'll have to just show you. I can't explain it." Her voice sounded odd, as if she were hiding something or stifling laughter, or both. Seconds later the lock unlatched and the door slowly opened. "Before you come in," she said, "no judging." I paused. When I was eighteen Carrie had walked in on me while I was having a private moment with a porn website. She had waltzed into my room, unannounced, with a stack of laundry. When she had opened the door she shrieked, as there I was, wearing only a t-shirt, my dick in my hand and stroking myself off. Her timing was perfect, or terrible, because just as she called out my name in shock I had started to come. I tried to hide my erection, to cover myself up, but my penis kept spurting cum like a fire hose. She averted her eyes, and started laughing. I kept coming, trying to apologize. Finally, my orgasm ruined, my shirt, chair, and floor covered in cum, she tossed me a towel over her shoulder. I covered myself and she turned around. She apologized for not knocking, and then looked at the mess, and had said 'no judging', and left the room. A few months later she caught me again, this time in a much more damning predicament. I was in her bathroom, erection in hand, stroking myself off. This time, however, I had already come. She had walked in, laughing in surprise and covering her mouth as she turned away. I was red with embarrassment, and as she turned around, she saw me blocking something from her view. "The latest Playboy?" she had asked, amused. I had already tucked my dick back into my shorts, my hands slick with lube and cum. She looked over my shoulder and saw what I was really hiding. On the counter was her black bikini, a small stringy thing she wore when she swam in our pool. It, and part of the counter, were splattered in cum. "So that's why I do so much laundry," she mused, then looked at me. "No judging, but please clean up my counter." And then she left the bathroom. Since then, 'no nudging' was a joke between us, but also a code that things of a sexual nature had or were about to transpire. This was the second time she had used "no judging" for herself. The first was about a year ago, when a box from an online retailer came to the house and, not noticing the label, I opened it before she could intercept it. It was a rabbit vibrator, and she fought off her embarrassment, took it from me, and said our code word and left the room. Now, as I unlocked her door and stepped into he dark room, I wondered what she had been up to. Carrie's room was too dark to see well, but I could see she was laying in bed, sitting up. I moved to turn on the lights and she stopped me. "Wait," she said. My finger hovered over the switch and she continued. "Seriously, no judging." "You've caught me masturbating dozens of times, how embarrassing can this be?" I asked. We always spoke freely about self pleasure, as I was constantly up to it and she and I always talked about everything. "I mean, this can't be worse than the time..." "It's worse," she said, cutting me off. "How bad?" I asked. "Worse than vacation two years ago," she said. Two years beforehand Carrie and I had gone camping with some family friends. She and I shared a small tent, which was fine until, the second night of the trip, I got restless. I couldn't sleep, and as usual I decided to relieve my constant sexual tension. Carrie lay next to me, asleep. We lay on our sides facing each other, and her tight black t-shirt stained against her breasts. She wore short shorts that had ridden up her thighs, and the view was perfect. Making sure to move as little as possible, I slid off my shorts, freeing my erection. Slowly, carefully, I stroked myself. I had been fantasizing about every able-bodied woman I knew, and that included Carrie. She was, as my friends often pointed out to my embarrassment, incredibly hot for her age. My father had married young the second time. Carrie looked at age thirty as hot as any twenty-year-old woman, and I found myself stroking to orgasm thinking of her more and more often. In the tent, I slowly stroked, my eyes on her tits and legs, moving slowly to avoid waking her. The slow buildup intensified my orgasm, so that when I came, it was a relentless torrent of cum. I closed my eyes on instinct, and only when the first spurt of semen issued forth I remembered I was a foot away from my stepmom. I opened my eyes in terror as the second shot hit her shirt, followed by a third, then fourth. I tried to aim away but only ended up sending ropes of cum onto her bare thighs. She flinched in her sleep and I stopped breathing, waiting for her to wake up. She didn't move, and as my dick stopped spurting cum I rolled onto my back, exhausted, and fell asleep. I had woken up the next morning to see Carrie sitting up next to me, staring at me. With a jolt of terror I realized my pants were tossed into the corner. I was half-naked, the important half, right next to her. "Sleep well?" she said, smirking. "Oh, I, um, I just..." I said, trying to think of something as I reached down to grab my shorts. She put her hand on my wrist and stopped me. "Just jerking off next to your stepmom?" she asked. She then pointed to her shirt, which had the undeniable streaks of cum by her tits. "Listen, I..." I started, but she held up her hand and stopped me. "I was awake," she explained. "I was trying to sleep, and then I opened my eyes for a second and saw you, um, taking care of things, and then a few seconds later you came. Everywhere." She gestured to her legs as well. "I'm sorry," I said, sitting up and looking away from her. I had not felt that terrible since my dad had died. She patted my knee. "It's okay," she said. "It's a small tent. I knew you were trying to relieve a lot of built up tension, I've been there myself. I know you do that pretty much everyday. I mean, how many times have I walked in on you doing it?" "Lots," I said, laughing. "It's just a little embarrassing, sitting here, naked, talking about it. Especially when I got it all over you." "I don't think you intended to," she said simply, as if that settled everything. "I'm not mad. Hell, it's not the first time someone's come on me." I looked up and she laughed. "And as far as sitting here naked, I've already seen you naked from the waist down." "But it feels weird sitting here and talking like this," I said. "Usually I cover up and we laugh, and you say 'no judging.'" She laughed. "True. Well, if you're uncomfortable, you can always put your shorts back on. Or..." and without hesitation she grabbed the hem of her shirt and lifted. I watched as the shirt pulled up, then around her breasts, causing them to drop as her shirt cleared her shoulders. With a swift motion she tossed it by my shorts, and sat topless next to me. "Hold on," she added, and lifted her ass and wiggled out of her shorts. She sat next to me, naked, as if this was the most normal thing in the world. "See? Nothing to be embarrassed about. We're just sitting in a tent, naked." She looked down, and saw that my penis was hard, throbbing with each beat of my heart. "Sorry," I muttered, embarrassed by my arousal. "Oh good god," she said, laughing, "don't apologize. I hate to break it to you, but it's supposed to do that when a naked girl sits next to you. At least you know it works." "But you're my stepmom," I said, trying to rationalize it to myself more than anything. "Your stepmom with dried cum on her legs," she said. "Don't worry about it. I don't want you to feel weird about addressing your own needs. It's normal. So, listen, I'm kinda tired, and I don't want to do anything for a little bit this morning. So I'm going to lay here, like this..." she lay on her side, away from me. I looked at her ass and felt myself get even harder. "...and I'm going to relax and let you lay there and take care of that erection, so we can go hiking. So just do what you always do, and pretend I'm not here." "Um, kind of hard to do," I said. "I can leave," she said playfully, "or you can come with me here. Your choice." "Stay," I said, "please." I lay down next to her on my side, looking at her smooth back and her round ass. She had a tan line that framed her ass. Awkwardly, I grasped my swollen member and stroked it. She lay on her side, unmoving, as I silently stroked myself off next to her. "You know," she said quietly, not moving from her position, "the first time someone came on me, it was while they thought I was sleeping. It's pretty hot." I stroked faster, and she said, "and now that you've seen me completely naked, I guess I could go around like this at home more...it's so relaxing." I sped up, stroking faster, feeling my orgasm building. This time I planned on flipping onto my back and coming up my stomach, but before I did Carrie added, "and just this once, you can come on me with my permission." That sent me over the edge, and I exploded. Thick streams of semen shot out of my dick, spraying her ass. I aimed as I came, shooting cum all over her ass cheeks. It was a huge load, and when I finished I was amazed at the amount that ran down her ass cheeks onto the sleeping bag. "Alright," she said. "If I go around naked around the house sometimes, you can't go sneaking into my room and coming on me while I'm asleep. Last night was an accident, I know, but don't get any ideas." "Okay," I said, still panting. She got up, wiped the cum with her black t-shirt, and slipped on her shorts. She pulled on a sports bra and a new t-shirt, and then slipped out of the tent, leaving me exhausted and confused. That memory echoed in my mind as my hand hovered over the light switch. Whatever I was about to see was more than I had seen in that tent. Sure, since then, I had seen her naked plenty of times. Sometimes she swam naked, or slept naked, and I usually joined her. Each time I would dash off to jerk off, only to get hard again a few minutes later. I flipped on the lights and let my eyes adjust for a second. "Oh my god," I said. "Just help me, please," she implored. She was sitting up in bed, a sheet around her legs, but she was topless. A second later I realized why she was sitting up in bed. She was handcuffed to the headboard. "Carrie?" I said, puzzled. "Look, no judging," she said, her face red with embarrassment. "Yes, I am handcuffed to my own bed. And I lost the key. So, please enter this judgement-free zone and help your stepmom out." "How did you get handcuffed to your bed?" I asked. "I did it to myself, on purpose. But I usually have the key on a bracelet on my wrist...and it's gone." "Usually have the key?" I asked, smirking. I was also looking at her breasts, which as always commanded my attention. "Yes, usually," she sighed. "This is embarrassing." "Let me help you," I said, walking over to the bed. I looked at the handcuffs. Sure enough, she had a bracelet on her wrist, with enough slack that, with time, one could snag a key and unlock the cuffs. Her wrists were red from the handcuffs, and there was no key on the bracelet. "Maybe it fell behind the headboard?" I suggested. "That's my guess," she said, shrugging. I set my tools down and took a flashlight, looking under the bed. "So this is usual thing for you?" I asked. "No," she sighed. "It's just. I don't know...can we be honest here?" "Aren't we always?" I called from the floor, still searching for the key." "Well, do you ever get tired of...getting off the same way?" I knew Carrie had not been with a man since my dad died, and I knew she owned at least one vibrator. It was no secret that she masturbated, but just hearing her say that made my already-hard dick twitch. "Yeah, I like to change things up," I said. "Me too," she said. "So every so often, I do this." I stood up, "it's not on the ground. Do you think it fell into the sheets? I'd have to move them to look." "But, um, how do you actually do it?" I asked. "With your hands tied." She paused, then sighed, "there's no point in hiding it, since you need to check the bed anyway. Go ahead and remove the sheet." I put my hand on the thin sheet and pulled gently. I draped and slid off her like a serpent, slowly revealing her flat stomach, then, to my surprise, her rabbit vibrator, inserted deep inside her. "Whoa," I said as I completely removed the sheet. Carrie had strapped her legs together with a belt, and had slid her rabbit inside, and then handcuffed herself to the bed. "The belt keeps the rabbit from slipping out," she explained, her face red. "So you just turn it on..." "And ride it out until the batteries die, which takes hours," she said, her blush turning deep scarlet. I stared at the rabbit sticking out of her. Her labia were parted around it, and her pubic hair, which she normally kept trimmed, were completely gone. "Okay," she said, lifting herself up a little. "Find that key and get me out of here." I got out to bed, sliding my hands under her body. As I felt the sheet for the telltale sign of a key the top of my hands brushed her ass repeatedly. "No free feels," she joked. "I'm not trying," I said. "Well, I can see from the tent in your shorts you aren't minding," she said, laughing. "Hey, if you don't want my help," I joked back. "I can swap out your batteries and leave you in peace." "Don't even joke about that," she groaned. "There's such a thing as too much stimulation, and I think I passed that around two in the morning." "No key," said, standing up. "I can cut the cuffs, I think." "Okay," she said. "But, this is really uncomfortable, can you help me out." "Of course, I said, reaching for a pillow to help prop her up better, but she shook her head. "No, not that. I need you to, um, untie my belt and...and remove the rabbit." "Oh," I said, understanding her. She blushed even more, and averted her eyes. "This is the most embarrassing moment of my life. Handcuffed naked to a bed, a vibrator stuffed inside me, and my stepson coming to my rescue." "Well, no judging," I said. "Besides, it could be worse." "I don't know how," she said. "At least no one can easily tell if you're aroused." "Oh you know I don't care if you've got an erection," she said. "It's pretty damn uncomfortable to have one," I said, working to untie her belt. "Then take off your shorts," she said. "Let it out, because this is going to take a while." "Are you serious?" "I've seen it before, Tom, just get comfortable because I can't have you running off to take care of that erection while I'm stuck here. You're not going to go anywhere until I'm off this bed. "Alright," I said, shrugging. I slid off my shorts, letting my throbbing penis spring out. It stood, pulsing and red. "Now that you're not straining against those shorts, get this belt off me and take that thing out of me." She closed her eyes and leaned her head back as I removed the belt. As soon as I did she spread her legs wide and stretched. The rabbit slid an inch out of her, then another inch. "Do you need my help?" I asked. "Yeah," she said, "It's stuck, and I'm too tired to push it out." I reached forward, my dick pulsing, as my fingers made contact with the vibrator. She took a sharp breath inward, her head still thrown back. "So I just yank it out?" I asked. "Slowly, don't pull hard." I slowly pulled, but it didn't budge. "It's stuck," I said, my hand still on the base of the vibrator. "Should I try wiggling it around?" "Whatever it takes," she said, closing her eyes. Gently I moved the vibrator back and forth, only a few millimeters, and slowly it started to move more and more. Soon I was sliding it in and out, barely moving it. She gasped as she felt it slide slowly out of her. I watched her labia accommodate the changes in shape as it slowly exited her. When it was almost nearly out I paused, joking, "are you sure you don't want new batteries and some privacy?" She laughed, causing the rabbit to slip an inch back into her. She gasped, and I held it there, firm. She sank a little more on the bed, letting more of the rabbit penetrate her. I kept my hand steady and watched, with my eyes wide, and show slowly fucked the vibrator. Then, after a pause, she said, "take it all the way out, please." Her eyes were still closed as I slowly slid the rabbit out of her. As I did her vagina slowly closed, regaining its original shape. The rabbit was now slick and I touched it carefully as her eyes remained closed. Then I tossed the rabbit onto the bed next to her and stood up. "Okay, I'm going to cut the chain that holds the cuffs, that way you can get off the bed. Then I'll get the cuffs off of you." I got onto the bed, kneeling next to the headboard, inspecting the cuffs closely. "Good news, I think I can just pry the chain open. Should save us time." "Thank you," she sighed, her eyes still closed. I was grateful, because my throbbing penis was inches from her face, wagging back and forth as I tried to pry open the chain. "This is so weird," she said, her eyes still shut as she tried to relax. Removing the rabbit had loosened her up. "I'm glad you're so understanding." "Hey, with anyone who is so cool about everything as you are, how could I not be?" I asked, looking down at her breasts as I worked. "So, Carrie, why handcuffs?" "Oh, I'm not into bondage and stuff," she said, "but it's fun to get handcuffed sometimes. It's just a little bit of danger I supposed. But this is probably the last time, because you never start out a night thinking you're going to have your stepson bail you out of trouble." "I'm happy to help." "You're just happy to see me naked," she chided, opening her eyes. As she did they grew wide, for my penis was inches from them. "Oh..." "I'm sorry, I can go and..." "No," she said, "no, don't. I'm fine." She said nothing more as I worked, but her eyes were locked on my penis. A few times I felt her breath over my penis as I got close to her mouth. Stepmom Needs Help "The chain's giving," I said. "Another minute." She surprised me by darting her head forward and quickly licking the head of my penis. "Carrie!" I said in surprise. She looked surprised as well. "Sorry," she said. "Reflex. I've given a lot of blowjobs handcuffed like this." "I thought you said you weren't into bondage," I said, my hands shaking and my mind reeling. There was a look in Carrie's eyes that I had seen only once before, in that tent two years ago, and then she shocked me by licking it again. "But it's all hard, and you can't possibly focus on getting me out of these cuffs when you're hard like that." She licked again, and again, and my hands stopped working on the chain. Instinctively I nudged closer, and the head of my dick popped into her mouth. She didn't hesitate, and started sucking my dick. I was on autopilot, bucking my hips slightly to meet her mouth. I was fucking her mouth, and she was reciprocating. It was all so erotic. The handcuffs, her swaying tits, her guttural moaning as she sucked me. It was all I could do to last as long as I did, but soon I felt myself coming. I started to thrust harder, and came in her mouth. Cum gushed out from my penis and flooded her mouth. She swallowed, keeping me in her mouth as spasm after spasm filled her mouth with cum. It became too much for her, and suddenly cum spilled out of her mouth as she gasped for air, splashing her tits with it. Spent, I sat back on the bed. I looked at Carrie, splattered with spit and cum, her chest heaving, like some used slut. She looked at me and grinned. "Now get these cuffs off of me." I worked quickly, my spent penis dangling in her face, still dribbling the last drops of cum onto her shoulder. With a pop the chain gave way, and Carrie pulled her arms down and groaned. She lay on her side, her face sticky and streaked with cum. As she did, I saw a glint of metal on the sheet. "The key!" I said, snatching it up and unlocking the cuffs from her wrist. "I must have missed it..." "When you were feeling up my ass. Don't worry, I just sucked your dick, the time for modesty has passed." She rubbed her wrists. "My arms are sore, my wrists are raw, and my pussy's sore as hell from that rabbit. Help me to the shower." I helped her up. Her legs were unsteady, and I half walked, half carried her to the shower. "Help me," she said in my ear. I stepped into the shower with her, and cleaned her off as she instructed. Her pussy was so tender that she practically jumped any time I went near it. Finally, she had me help her towel off. "Are you going to be okay?" I asked. "Yeah, I'll be alright. I feel better already." She leaned forward and kissed me, her tongue finding mine. "In fact, I think things are going to be great around here." "How so," I asked, grinning. "Neither one of us is going to need to take matters into our hands. And this afternoon, let's go buy a new set of handcuffs." "Padded, this time?" I suggested. "Definitely padded," she laughed, "but right now, I'm so sore down there, will you settle for another blowjob from your stepmom?" I pulled her close to me, kissing her fiercely, "hey, no judging."