Janie's Confession

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Janie gets tangled up in Chatroom Bob's web.
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ptstewart
ptstewart
226 Followers

I'm writing this to say sorry to all the people I've hurt. My name is Jane Smithers; Janie to most of my friends. I graduated high school at eighteen and went straight to college. Big mistake! I wasn't ready and failed my courses and they chucked me out. The psychologist my parents sent me to said I was depressed, but really I just wasn't interested. I missed home and felt lonely. My folks freaked of course; Dad especially. Once I was home I just sat in my room. My friends were all off at college. The only job I could get was minimum wage slavery at the local diner. I hated it. When I got home from work I just went straight to my room; I hardly spoke to my folks at all. Everything was shit basically.

I remember the night I first went to the chatroom. We lived in a suburb and the only way to get anywhere was by bus because my Dad refused to let me use his car after dark. I was so fucking bored; I had nowhere to go and my friends were too busy with their own lives to listen to my endless complaints. I had the lights off and my music at minimum volume. I was surfing blogs and clicked my through links to a porno site. I admit I'd been to some before, just to check stuff out; more as a joke really. When the chat panel came up it was some, like, forty year-old guy which was totally weird. I guess I responded because I was so bored. I don't know what I expected but he seemed interested in me and I just complained and complained about my life. It felt so good. He wasn't pushy about the sex stuff. He did ask me about my boyfriends -- all ex-boyfriends actually. He asked me what I looked like and I explained that I was a redhead and was skinny and fairly tall. He said some very sweet things and I guess I'm as open to flattery as the next person; it seemed like someone was really listening to me, paying attention to me. I like being checked out by guys although I'm pretty shy and I have this horrible tendency to blush when guys look. He lived in Chicago, far from the Boston suburbs where I lived. I suppose that's what made it feel okay to email him a photograph -- just an ordinary one of me taken by my friend last summer in a local park. I felt flattered that he wanted to see me; I wanted to be seen and I felt this need for him to like me.

The next night he was waiting for me. I'd spent the day looking forward to chatting again. I suppose I did question myself but it all felt so safe then, so harmless. He asked about my day and seemed so interested in it, unlike my friends who were studying philosophy not serving greasy fries like me. He told me he was married but that his wife wasn't interested in sex anymore. He asked me how many guys I'd slept with. I'd only done it with two guys; my high school boyfriend and some guy at college who dumped me after just three weeks. It felt sort of weird to tell some stranger this stuff -- but also sexy.

Then he wanted to know the color of my panties. I remember pausing then, my heart beating, my face flushed. This was crazy I knew, but I told him. I told a forty-year-old man the color of my panties. He wanted to know what kind, whether I wore thongs, whether I ever went out without panties. I told him everything he wanted to know. He asked when I last masturbated. I told him. It felt exciting, exposing, exhilarating. He asked what I was wearing. I told him every detail. Then the word "pussy" arrived on my screen. I imagined him typing it out. "Do you shave your pussy?" he asked. Then he wanted to know whether my pussy was wet. "So wet, so squishy and fucky," I said. "You turn me on so much," I typed. He wanted me to touch myself, to masturbate for him.

I can't explain to you how it felt to have Bob (that was his name) in my life. It was like I had this huge secret, this specialness that only I knew about. I longed to get home from work, to get to the chatroom. I know most of you won't believe he cared about me but you weren't there. He was the only one who cared about me. I sent him more pictures of me. I was addicted to his praise and flattery I suppose. Then one night he asked me to get my Dad's digital camera and take a photograph and send it to him. I crept downstairs and lifted the camera from the office and snuck into the bathroom. I snapped the photos in mirror. In the first photo I'm fully dressed in my low-rider blue jeans and purple tank top. In the next one I've taken off my jeans and showing off my red thong. Then I took off my top and bra and show him my 36c breasts. In the next one I'm naked, my pussy exposed to him. He loved them. He was so proud of me.

I told him all about work; he seemed so interested in all my gossip and complaints, unlike everyone else. One night he asked me to go to work the next day without panties. I didn't -- I don't know why; I guess somewhere a voice was warning me. I had always been honest with Bob so when he asked that night I told him the truth. We'd been chatting for a few weeks by then. The chat panel disappeared and I waited up until three in the morning for him to come back; he didn't. I emailed him but he didn't reply. I was devastated -- even more devastated than when the college guy dumped me. I couldn't believe it. Three days went by without a word. On the third night I got a one line email: "Don't disappoint me again." I promised him I wouldn't. I was so scared I would lose him.

I went to work without panties as ordered. I couldn't wait to tell him how good I had been. Bob was right; it was very sexy to be so open and so aware all day of myself sexually. There was a guy at work I always complained about who was a total creep. He was fat and greasy and everyone laughed about him behind his back. He would brush up against us girls in the kitchen and behind the counter. Bob wrote: "Let him touch you next time, don't move away." "Why?" I asked. "Because it will give me pleasure and because I want you to do it," he said.

I felt the fat and greasy one maneuver himself behind me late in the afternoon after the lunchtime rush. The manager was in the back office and the other girl was outside smoking. Instead of sliding away I stayed still, suddenly incapable of breathing. "How you doing Janie?" he asked in his weasely voice, cupping my ass and scrunching the fabric of my skirt. I was rigid and tried to blank my mind but his short, fat fingers soon found their grubby way beneath my skirt. He pressed closer, his odor overpowering, his poisonous breath on my neck. I found myself moving my legs further apart, opening myself up to his finger that probed and then found my hole. I told myself I was wet for Bob; that I was responding for Bob. He sunk his finger into me. I could feel his palm against my ass. His cock pressed against the zipper of his pants against my thigh. I reached back and touched him. His breath exploded from his mouth and I felt a surge of wetness ooze through his pants and onto my hand. It was over in a couple of minutes. The old man slumped over his coffee in the corner was oblivious.

I told Bob everything. He called it my "task" and said that there would be more. He was so proud of me and I felt desperate to please him, to keep him. I masturbated each night for him, took photographs of myself, close-ups, everything. Bob didn't say anything about more tasks for several days. I was scared I suppose but also excited, just waiting.

Next he wanted me to go to a bar and get picked up by an older guy. He gave me the name of a downtown hotel where businessmen stayed. He told me to wear a pair of tight jeans and to put my hair up in pigtails. The barman of course carded me and looked very suspiciously at my ID. I could feel all those suits behind me looking, staring at me. Eventually a guy, tallish, forty-ish, with a bit of belly in a charcoal suit and bright red tie swung onto the stool next to me. "You look like you're waiting for your Daddy," he said in a Southern accent. "No, sir," I said, staring at my drink. "Would you like me to be your Daddy?" he asked, grinning. "If you want to be," I said, blushing crimson.

When we got to his room on the sixth floor he insisted I call him 'Daddy'. It was weird. He undressed me slowly like I was something precious all the time talking to his 'little girl'. When I was naked he planted me on all fours on the bed and then, after stripping off himself, slid underneath me so that his hard cock stared up at me. He pulled my hips down so that he could run his tongue through the separation of my ass cheeks and across my asshole. Soon his mouth covered my pussy, his hard tongue penetrating the folds and finding my stiff clit. This was the first time anyone had done this to me. I quickly cummed, letting out a small yelp of intense pleasure before collapsing on him. He slipped out from beneath me and positioned himself behind me and quickly entered me, all the while talking; "Look at Daddy while he fucks you," he said. He pressed his thumb into my butt and then shot his full load deep into me. Less than an hour after entering the hotel lobby I left and was out on the street again.

Next Bob gave me the name of a sex shop downtown. He told me to accept the first approach made by a guy. I went straight from work. After I jumped off the bus I made my way through the dirty streets with shuttered, abandoned shops until I reached the dark entry way of "The Scene". I'd never been in one of these places before. Immediately I could smell the leather and plastic of the toys and clothes. Behind the glass-topped counter an old guy sat reading a novel. He looked up when I entered, didn't seemed surprised to see me and offered a gap-toothed smile. Above his head a porno played silently on a small TV. There were two other white middle-aged men browsing through the videos on the back wall. Both had a furtive look about them and avoided eye contact with each other. I made my way to the nearest display which happened to be of dildos and vibrators and feigned interest. In accordance with Bob's instructions I was wearing my short green wool skirt, a white stretch tank top that accentuated my boobs and exposed my tummy, and a black jean jacket. The panties and bra I wore to work were now stuffed into my locker at the back of the diner. From the corner of my eye I checked out the two men. The one nearest to me was older and hunched in a big grey coat. He was mostly bald with wisps of grey hair above his ears. The other one was younger, bearded, and dressed like a construction worker. I stared, without really seeing, at the array of devices in front of me. I could feel their eyes on me now. "See anything you like?" asked the counter-guy with a smirk in his voice. "I've got something she'll like," the construction worker said in a mean and challenging way. The counter-guy laughed and said "I bet you have, Ricky. Bigger than those plastic ones she's been eyeing." The office worker snorted with his own laughter at the counter-guy's wit. That's when I should've left but I didn't. This was Bob's fantasy -- for me to be sexy with these guys and we'd talked about it so much that it'd become my fantasy too. I smiled my little girl smile and shrugged my shoulders. "Come on show us your tits you whore," the construction worker snarled. The counter-guy stepped out and said "Calm down now, everyone's going to get a piece of her. Let's take it slowly." He walked over to the shop door and flipped the sign announcing to the dreary, dirty street that he was, temporarily, closed for business.

My knees were shaking as I slipped out of my jean jacket. The office worker was rubbing his crotch where I could see the hardness of his erection. The other two stared at my chest. I let my jacket fall and then pulled my stretch top high over my head. I felt my breasts bounce back and heard the intake of breath in the stuffy room. The office worker cock was poking through his zipper. I moved towards him reaching for his dick. It felt smooth in my hand and his balls were hard. I slipped to my knees and licked the head. I heard his groan as I enveloped his shaft in the wet warmth of my mouth. "Her cunt's mine," the construction worker announced. I felt the office worker's balls tighten and he leaned into me. Without notice he exploded onto my tongue, shooting cum like fire to the back of my throat. The construction worker stood behind me and pulled me to my feet. He pushed me across to the counter where he bent me over and lifted my skirt. He unbuckled his pants and pulled down his shorts. Forcing himself between my legs he plunged his cock effortlessly into my ready, wet hole. He thrust angrily, deeply into me. My clit was trapped against the edge of the counter and raged with the stimulation. He fucked me with a vicious rhythm, using all his strength. Suddenly my own tension became too much to bear. A deep moan escaped my throat and my body convulsed. Seconds later the construction worker orgasmed powerfully, shuddering deeply.

I slipped to the floor exhausted. The counter-guy ushered the others out of the door. He helped me to my feet -- cum from the construction worker slid down my inner thigh. He handed me the remains of a can of soda and told me to get dressed. After I pulled on my jacket he stabbed the till and extracted four crisp fifty dollar notes. I tried to explain that I wasn't a prostitute but he laughed. "Come on Thursday, same time. I'll have a couple more guys for you -- we share the cash fifty-fifty." Again I tried to explain but he interrupted me with an announcement that knocked the breath from me. "Bob will be pleased with you. He wants you to have the money." I dropped the can of soda. I was stunned. "Here," the counter-guy said softly, gently, "take the money and come on Thursday." In a trance of disbelief I pocketed the cash and left.

I remember lying on my bed in the dark after I got home listening to the sound of my parents moving about the house, replaying the events of the evening over and over again. I couldn't believe what I had done, how easy it had been. I'd stopped off at the mall on the way home and bought some new clothes. It felt good to have some money to spend. I pretended to be angry with Bob when he came online later. After telling him all the details of what happened I admitted I was wet and as usual I masturbated for him, thinking of the construction worker.

On Thursday I sucked off two guys and had sex with another. After the counter-guy gave me my money he brought out a bottle of vodka and we sat there in the gloom drinking and talking. I asked him about Bob but he said very little. Instead he told me his life story; his broken marriages, his alcoholism and his child who died in a car accident. While he spoke he caressed my hair and face. Maybe it was the vodka but I felt warm and safe. He felt like a friend. Perhaps that's why I kept going back, week after week.

You know the rest of the story. I went to the 'Scene' after work for nearly two months before I was arrested. When they raided the shop they ushered the guys out except the counter-guy who burst into tears. They wouldn't let me get dressed but made me stand naked while they asked questions. It was only then that the enormity of what I'd done dawned on me. It turned out that the counter-guy was 'Bob'.

I don't know what to say. I know you're all devastated. I'm sorry, truly, deeply sorry.

ptstewart
ptstewart
226 Followers
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AnonymousAnonymousover 6 years ago
5! Another retarded comment from the asshole of LIT., annony

this fool reads all of these LW and cuck stories and then votes 1 and bitches about them and the writers. He's fucking insane.

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