Family Business

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Editor’s note: this story contains scenes of incest or incest content.


Laying on my bed in my room in my mom’s trailer, my laptop was set on the table beside me with my webcam aimed where I lay. White, satin, bikini panties were looped around my left ankle. The snug-fitting, stretchy crop top clung to my narrow, smooth chest and left my midriff bare. I was alternating between sliding a thin, lime-green, 6-inch dildo in and out of my little ass, and teasing my little pink penis with the pad of my index finger. I’d edge myself with my fingertip until I got close to squirting. The next time I’d slide the dildo in and out until I got close to a hands-free sissygasm. But I kept myself from squirting. The longer I lasted, the more generous my audience of 30 or so men became.

Hearing the flimsy screen door open and shut, I knew my Mom had returned from work. I whimpered a soft, ‘Hello’. She didn’t reply, instead, she came to my room and stood in the doorway and watched me perform.

With her arms crossed under her enormous breasts, she asked rather casually, “How long have you been at it, Leslie?”

I squirmed on the bed as I pulled my fingertip away from my trembling penis. Moaning softly, “Since before lunch.” After pausing for only a second, I began sliding the dildo in and out of myself at a very quick pace.

Mom stood there in the doorway where my audience couldn’t see her and asked, “What would you like for dinner? Anything special?”

The sissygasm built quickly inside of me and I released my hold on the dildo but left it inside. I lay there on the cusp of an orgasm, but just shy of it, writhing in frustration. While still dealing with the denial of my most recent release, I asked my audience what they thought I should have for dinner. The responses come back unanimously; I should have a big bowl of cum for dinner. My mom chuckled and said she’d see what she could find.

After I’d finished high school, my mom told me I’d need to start pitching-in if I was going to stay living within her trailer. I tried a few different jobs, but they weren’t right for me. When I was about to start searching for my 4th job, I ran into a boy I knew from school. He was gentle and feminine like me. While we were talking, I mentioned I was looking for a job. And that’s when I learned about webcamming. Since then, I’ve made more money than my mom most months.

After the first few weeks of camming, I learned my primary audience, middle-aged men, wanted me to look even more like a girl. I began shaving away my body hair until I could afford to get waxed. I let my dark brown hair grow out past my shoulders and I began to build a wardrobe of girl’s clothes.

Over time, I began to build a fanbase and those men would occasionally buy me things from a wishlist I had online. At first, I only had clothes, makeup, perfume, and even some jewelry on my list. But then I added naughty toys, butt-plugs, and dildos. While browsing for other things to add to my list on my phone one evening, my mom sat down beside me. She asked if she could pick something out. She wound up adding a metal chastity belt and a leather paddle. She even put a note on both items letting everyone know she’d picked them out for me.

It wasn’t surprising that the chastity belt and paddle were the next two gifts to arrive. The following camshow, I edged myself for more than an hour before I gave myself a hands-free sissygasm. While I was cleaning up, my mom walked into my room. As always, she stayed out of view of the camera while picking up the unopened chastity belt form my dresser. “Leslie, are you ever going to put this thing on?”

With my camera still on, I said, “I guess I could try it on now.”

Without any warning, my mom then moved into view of the camera and sat on the bed near my knees! After I’d introduced her to everyone, the comments began pouring in. Before having me, she was a petite girl. She was a cheerleader in high school. But after giving birth to me, she began struggling with her weight and has always struggled with her body image ever since. But the comments from our audience weren’t at all negative. Most were quite crude, but they were positive concerning her physical appearance. And I could see how much she appreciated hearing those things.

Together we read through the instructions for the chastity belt and figured out how it worked. I put it on, neither of us was overly comfortable with her touching my wilted, pink penis. But she did slip the lock through the pin and close it. I shivered and my penis began to swell having her hand so close to me. My little penis quickly filled the tiny space that extra-small chastity belt allowed.

Mom and I both couldn’t miss the money adding up so quickly in my little bank. Mom reached across to my dresser so she could grab the leather paddle. After holding it up so everyone could see, she slapped it against her hand making a loud slapping noise. I squirmed on my bed while my mom told my audience that if everyone donated bingöl escort $20, she would spank me with the leather paddle.

The money arrived quickly and I soon found myself face down, ass up on the bed. Mom moved the camera to allow everyone a better view. She then gave me five hard swats with the paddle. I jumped each time! They stung, but not bad enough to make me cry. The globes of my bottom were left a bright-red and a little tender.

After I’d rolled over and sat gingerly on my bottom, mom told me to spread my knees. Doing as I’d been told, I leaned back on hands giving our audience a clear view between my skinny, smooth legs. The metal chastity belt kept my poor little penis trapped and unable to get stiff. Mom asked the audience how long she should keep me locked up. The answers ranged from letting me out immediately to keeping locked up for the rest of my life. Mom decided she’d make me wait 3 days.

Considering it was her first time on camera, she got used to it very quickly. Much more quickly than I ever would have guessed. Not only did she take an active role, but she also began telling me what to do! That evening, we made more money than either of us had ever made in a single day before. I’m sure we both knew it wouldn’t be the last time she appeared with me on camera.

I was desperately horny that night and begged my mom to let me out, she flat-out refused. The next day was even worse, especially after I gave myself a very frustrating sissygasm, in my cage, online. But the next day was by far the worst. I was running around the trailer naked, begging her to let me out, but she was having none of it. She was with me when I went online that day and my audience listened while I begged her to let me out, she never did. After she left the room, I gave myself another caged, sissygasm that left me even hornier than I’d been before.

On the third day, I did my show in the living room, not my bedroom. I came online wearing a new string bikini a fan had bought for me. The bulge of the chastity belt was unmistakable. My mom sat on the couch and when I moved in front of her, she pulled the strings on my bottoms very slowly until they fell away. Wearing just a bikini top and my chastity belt, mom took my hand and had me sit on her knee.

Mom told my audience how horny I’d been since she locked me up. She told them I’d been begging her to let me out. She told them I’d cleaned our whole trailer in hopes that she’d take mercy on me. She told them about the several times she’d caught be clawing at my cage. She even told them how she’d caught me trying to break it off with a pair of pliers I’d found in our little toolbox. I confirmed everything she said as fact.

When she took the key of her pocket, I whimpered softly and squirmed my bare bottom against her knee. One of the men offered to pay $20 if she left me locked up for longer. A different man offered $50 for my mom to unlock me. Another man offered to match the $50 if mom unlocked me. She reached around my hip, picked up the lock, and slipped the key into it, being careful not to touch any part of my bare body. I was shivering and my little penis was desperate to become stiff. Mom then set the lock with the key in it, gently back down onto the cage.

The donations were adding up quickly while I was perched on my mom’s knee so horny after being kept chaste for three days. Mom reached up and slowly untied my bikini top leaving me naked except for the cage. I was about to go out of my mind I was so horny! We hadn’t planned this. The key was in the lock! All I needed to do was reach down, turn it and I’d be free! But that wasn’t how it was going to work. She needed to either grant me permission or turn the key herself.

One of my regular viewers offered $20 if we French kissed. My mom and I looked at each other and shook our heads. He asked if $25 would be enough. We turned him down again. He asked if $30 would do it. Mom nodded and said we’d do it. I looked at her, to make sure she was serious. Was she going to kiss me?

After our balance rose by $30, my mom had me turn a little bit before laying one hand on my lower back and the other on my neck. She pulled me toward her and I whimpered softly as I looped my arms around her neck. I tilted my head to the side and our audience had the perfect view of my mother’s tongue sliding into my mouth. It was a long, slow, wet kiss that made my toes curl and my poor penis cramp up painfully in its cage. I was moaning softly and trying to catch my breath when my lips left hers. But mom wasn’t finished. She sucked my lower lip into her mouth and then kissed me again. Until that moment, I’d never been kissed that passionately before. My whole body was tingling.

Looking at the monitor while trying to catch my breath from the kiss of my life, our audience had begun to ask my mom to take the cage off and make me squirt. Mom told them it was going to take a major donation for that to happen.

While the balance began to rise, Mom caressed bitlis escort my naked body with her fingertips. I was squirming like crazy and when I leaned toward her, she leaned in to meet me and we kissed some more, long, wet, passionate kisses. I wound up straddling her ample lap, my arms around her neck while she caressed my back as we kissed. I eventually withdrew my tongue from her mouth and mumbled incoherently, “Mom, I have to… I can’t keep… I’m so…”

We arranged the camera to provide the best view. She then had me turn around so I sat on her lap facing away from her. When we were all set, mom reached around me and held the lock between her finger and thumb. Her other hand drifted up from my belly button to my little pink nipples. She pinched each of them while watching the balance rise and learning what our audience wanted to see.

While looking over my shoulder, she turned the key, and lock popped open. Very slowly, she removed the lock from the chastity cage. Using both hands, she slowly and gently removed the cage from my little penis. By the time the cage slipped off of the little pink head, my penis was perfectly erect and throbbing wildly.

Mom set the cage aside before setting her hands on my naked hips. She asked my audience where they wanted her to touch me. Her hands slid slowly around my front until they framed my smooth, little, throbbing penis. My hips ground up against her hands, but she kept them clear of my desperate penis.

Leaning back against her, I moaned, “Mom!”

She kept her hands framing my frantic penis while asking, “Yes, Leslie?”

Reaching back to lay my hands on her hips behind me. “Mom, I’m so horny!”

She kissed my naked shoulder and asked, “I know, Baby. What do you want me to do about that?”

I moaned, “Touch me! Touch it! Please?”

She teased, “You want me, your mother, to touch your little-bitty penis that’s already leaking its juices?”

I ground my hips upward, but she never let her hands touch my penis or my little pouch. I whimpered, “Yes, please. Pretty please?”

Sitting on her lap, my legs straddling her knees, I was leaning back against my mom. Her hands moved closer to my throbbing prong. I rolled my head to the side and she leaned in and kissed me. At that same moment, the pad of her first finger touched the underside of my penis, just below the squishy pink head. My hips bucked up and moaned into her mouth while my penis squirted out a long line of my creamy love almost up to my neck.

Mom kept slowly rubbing her finger in that magical spot just beneath the head of my penis on the underside while our tongues danced together. I squealed into her mouth as the next line was launched from my little penis. This time ending just between my nipples. My hips bucked up hard and the third line ended near my belly button. Mom kept rubbing, slowly and gently, while I lay back against her coming back to earth from the orgasm she’d just given me. She held me on her lap, kissing my cheek, neck, and ear while my creamy love began dripping down my sides. When my penis had wilted to its normal tiny size, my heart was still pounding and I was exhausted. I lay against her while she put my penis back into the chastity cage and closed the lock once again.

Looking to the camera, my mom asked in a raspy voice, “How long should he be kept locked up this time? A week? Two? A month?”

After taking control of my orgasms with the chastity belt and beginning our taboo relationship, the income from the cam business was skyrocketing. Mom began appearing in every one of my shows. It became so profitable, she was soon able to quit her job. The more she appeared on camera, the sexier she began to dress. Her tops got deeply cut, showing off her gigantic boobs. She began paying more attention to her hair and spending more time on her make-up. My audience more than doubled in size after mom began joining me.

After appearing in several shows, mom started her own wishlist. Her lists were mostly composed of nightgowns, sexy tops, dresses, makeup, perfume, and jewelry. But after receiving several packages from our viewers, she added a few vibrators to her list. When our audience bought those for her, I began hearing them buzzing in the next room after most of our times on camera.

My stints in chastity began to regularly last for a week or two. In between orgasms, I relieved the pressure with daily sissygasms by rapidly humping one of my many dildos or vibrators. Stimulating myself in that manner was never like a real orgasm. I was left feeling cheated and denied. Yes, my juices would ooze and drip from my little penis, but it wasn’t like a real, full-blown orgasm. I came, but all the wonderful feelings and sensations associated with orgasm weren’t there. Or course, mom would be sitting nearby while I toyed with myself. At first, she just watched. One afternoon, after watching me struggle to keep hold of it, she began holding the dildo steady as I humped it. And eventually, she had bolu escort me lay face down across her lap and slid the dildo in and out of me until my orgasm drizzled from my cage, between her thick thighs.

What used to be my little show had become a family affair with my mom calling all the shots. She was deciding what we’d do and when we’d it. I appeared online each day not having any idea what was in store for me. We never kissed or did anything more when we weren’t on camera. However, I did spend the majority of my time running around our little trailer in panties or naked except for my chastity cage.

After appearing together for several months, my mom delayed my release from chastity for several days so it would land on her birthday. Our audience loved the idea. I’d been laying across her lap while she slid my thickest dildo in and out of my bottom. The balance in our bank had been climbing sharply all day. As I neared my sissygasm, one of our longest and most faithful viewers offered to provide something special for my mom’s birthday. Mom left me writhing on her lap while she DM’ed with him, not allowing me to see anything they discussed.

When a package arrived less than a week before her birthday, she kept the box in her room and did not allow me to see what was inside. Those next days leading to her birthday were torture. We appeared online every single day. And everyday mom would tease both our audience and me about what she had planned! I was going crazy both from the frustration of being kept chaste and the burning curiosity of what the surprise would be.

On her special day, just before we were to go online, I stepped out of the bathroom after taking a long shower. I found her sitting in the middle of our couch in the living room. Her hair and makeup were perfect. She was wearing a light pink, thigh-length, satin robe I’d never seen before. Beneath that, I saw hints of lace of a nightie I’d never seen before either. She looked radiant, very pretty, and excited. The fat nubs of her nipples were poking lewdly against her nightie and robe and the scent of her arousal was unmistakable.

Laying on the coffee table, which had been pushed off to one side of the small room, were the contents of the box she’d kept hidden. A blindfold, thigh-wrist cuffs, and a chin-mounted dildo that would cover the lower half of my face. Beside those items lay my earbuds and a nose-plug I used in a swimming class I’d taken the year before.

I stood there naked, except for my chastity cage and my whole body shivered uncontrollably. I whimpered softly, “Mom?”

She sat there grinning at me. “Run back into the bathroom and get your brush and hairbands. I want you in pigtails today.”

After racing back to the bathroom, I returned with the things she’d asked for. Kneeling on the floor at her feet, facing away from her, she parted my hair down the middle and pulled each side into a long, brown pigtail on the sides of my head. While she worked, she explained, “Leslie, Honey, this is my birthday. And we’re going to do something special for me. In the past, our cam shows have always been about your pleasure. Today, this show will be about mine.”

I didn’t respond to the statement, I didn’t feel it was necessary. I knelt there silently on the floor while she tightened up my pigtails. After all, we’d done together, my feelings for my mom had changed. She was still my mom and I loved her for that reason alone. But she had become the star of all my fantasies. Laying naked across her lap while she milked me with a dildo had become my all-time favorite thing to do. It didn’t matter that I wore a chastity belt at the time. Having her perform that act was incredibly sexy and made me feel extremely close to her. And those rare occasions when she touched my desperate penis after it had been kept locked up for a while, those encounters were what my dreams were made of. Her touch was always feathery, like a breeze, barely touching me at all. But making enough contact so my denied penis would erupt all of its pent-up frustrations.

Mom had already positioned the camera and after finishing with my hair, we went online. The first thing our audience saw was me kneeling naked on the floor at my mom’s feet. It had been the longest I’d gone without an orgasm to date, 22 days. I was a frustrated mess. My hips were squirming around lewdly while mom greeted everyone online by their screen name. While she did that, she wasted no time and began preparing me for her birthday surprise.

The thigh-wrist cuffs went on first. Kneeling on the floor, my forearms were forced to lay parallel beside my thighs. I was hunched over and the bindings made it difficult to move around much at all. The blindfold covered my eyes and left me in complete darkness. Unlike other blindfolds that let some light through, this one left me without even a hint of sight. The chin-mounted dildo that strapped behind my head with two sturdy straps was next. It took mom some time to get it in place, but when she was done, it covered me from beneath my chin to the just below my nose. The noseplug was next and she was careful to ensure it held both my nostrils firmly closed. Last, but not least, she slipped my earbuds in and used my phone to turn on some loud music.

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