by Jane Futa
If my initial expression toward Jessica had seemed to be one of shock, then my expression after leaning about her work-at-home gig must’ve been one of total horror. Though, to be honest, it was more from the fear of her finding out that I was in that very moment, trying to visualize just what that entailed.
Did she write blogs online pretending to have tested the latest dildo for some company that compensated her with ad revenue? Or was it something much more forbidden? I couldn’t help but imagine the tall, delicious blonde, spread eagle on her pink bedtop. Her smooth, tawny legs spread as she took a life-like rubber cock in her careful fingers and inched it toward her sweet, red juicy mound.
The image brought my cock to a lazy swell in my pants. It didn’t help that Jessica had bit her lip as the words left her dirty little mouth.
“I’m sorry,” she giggled with an expression of bashfulness. “Was that too much information?”
“What? Of course not,” I said.
“Are you sure? I wouldn’t have told you, but I don’t want there to be any secrets between us. I want to be totally honest with you, Mr. Stevens.”
Jessica puckered her juicy red lips and bit into the bottom one, before turning for the door.
“You’ll let me know if you decide to rent to me?” She asked.
“Wait, Jessica,” I said, stepping toward her. I instinctively reached for her hand, touching her silky skin with my own. She seemed taken aback by this, but certainly not for lack of want.
She took my hand and held it in her own as she turned to face me with an inviting smile.
“Yes?” She asked.
“Um,” I started, taking my hand from hers. “The room is yours. Really, it’s no business of mine what you do for work. In fact, I shouldn’t have asked.”
“Come on, Mr. Stevens. Everything I do in your house is naturally your business. I want to be the perfect tenant for you,” Jessica explained.
I should have turned back and told her I was going to think about it. I should have known the sort of trouble that would come with bringing a hot, eighteen year-old female into my house. But I couldn’t help myself; if for no other reason than to help her out, since she seemed down on her luck and temporarily without a place to call home.
I should have known it would come back to bite me in the ass; not just the fact that Jessica seemed a little too sneaky for my comfort, but because I was harboring a dirty little secret of my own.
I had gotten into the habit of perusing a porn site with amateur girls who stripped naked in from of their webcams. It was a little perversion of mine, and seeing as how it was my only real one, I didn’t place too much harm in it. After all, I still had plenty of success with women; it wasn’t as if I needed it or anything. But it eventually caught up with me.
Before I could even process what I had done, Jessica had been living with me for a couple of days. Her move-in was uneventful, considering her possessions were confined to everything that would fit in her 80’s hatchback.
It wasn’t until I heard her moaning from down the hallway one evening that I realized I had either made the worst or the best mistake of my life in renting my room out to her.
I had just finished a research topic on my laptop downstairs, when I closed up for the night and headed upstairs to my bedroom. I passed Jessica’s room, and noticed the light escape from the crack beneath the door. It was well past two a.m. when I heard her quiet sighs of delight, accompanied with a vibrating noise.
“Fuck,” I whispered. My dirty little imagination had proved correct. Jessica was doing more than blogging about dildos and vibrators. I couldn’t keep from listening, even as my heart sped wildly in the dark hallway. I knew I should move; what if she swung the door open as I was listening?
The sounds only left me horny and unfulfilled. I grabbed my laptop and left for my bedroom, shutting the door and locking it behind me, as I logged into the cam site I’d been frequenting. That’s when the first sign of something afoot manifested itself.
“Hey,” a message that had popped up in my inbox read. The cam site had a messaging system that delivered little notes to or from models and fans. I wasn’t a fan of any particular model, rather browsing casually when I had the urge. The reception of a message, especially that of a cam-girl, was a bit strange.
“Um, hi. Did you mean to message me?” I wrote, sending the message right back to the cam-girl named Lilcollegesecretslut92.
“Of course I did,” read the message that turned back in my inbox. “Want to watch me cum? I saw your profile pictures and um… you are super hot ;).”
Without any further response on my part, I went to her cam window, only to find something I’d never looked at before. There, in the window, was a delicious, beautiful female body from neck down. The model’s face was hidden, but the bottom of her blonde hair was hanging over her shoulders. Only, beside her tight little frame, her big breasts and her long, lithe legs, was something completely unexpected.
The girl was stroking a long, hard cock that jut out from between her legs. She was spread eagle across the beige carpet and shoving a little vibrating toy of some sort, against her asshole. I watched, mesmerized as her ball sack flexed with her ass at every little jump of the toy.
“Fuck,” I whispered. The cam stranger’s delicate body was sheened with sweat as her hips rocked and she rubbed her breasts.
I had never been one to look at transsexual porn. In fact, I had never done so. Yet watching this young transsexual masturbate before the cam, left me rock hard, if only for the fact that her blonde hair made me immediately imagine Jessica in front of that webcam.
I pulled my cock from my pants and immediately started to stroke, moaning lightly as I doubled-checked to make sure my door was locked.
I stroked harder, just as the cam model stopped and reached over for her laptop keyboard. She typed something for a moment, and a message popped into my inbox.
“Are you having fun?” It read.
“Fuck yeah,” I replied.
“Will you show me?” She asked.
“What do you mean?” I wrote back.
“Do you have a webcam? I want to see IT,” she wrote back.
My mind flashed with a million conflicting thoughts. It was strange enough that I was masturbating to the image of a woman with a cock. Was she a woman, or a man? I honestly wasn’t sure what the proper orientation was. In that moment, I didn’t care, because more than anything else, this person performing for me was beautiful exactly as they were.
“I’m not gay or anything,” I wrote.
“I never said you were. Don’t you find me an attractive teen girl?” She wrote.
“Fuck yes I do,” I wrote back eagerly, stroking my cock with my other hand as I watched her tits hang over the screen.
“Show me how much you love it; it would make me cum more than anything,” she wrote, sending the message right back.
I gave in. I turned my webcam on and tilted the laptop screen toward my rock-hard cock. I was pleased to show off my large dick, knowing that the cam model wouldn’t expect as much. None of the women I had been with ever had, and their first impressions alone would always make my night. Luckily, I was considerably bigger than her – otherwise, I might have had more mixed feelings.
“Oh my… are you kidding me? ;)” she wrote, upon seeing my cock in the dim lighting of my laptop screen.
“It’s massive,” she wrote. The compliment made me eager to show her even more what I had to offer. I stroked my cock, and she did the same, watching me.
“What would you do with that thing?” She asked.
“I would sink it so far into you,” I wrote, before remembering that she had no pussy. What I was describing was more or less fucking a man, dressed as a girl. I was then fantasizing about fucking her asshole, all while I watched her cock and balls bounce with every hard thrust.
“Mmm, I want it so bad!” She wrote back, before returning to the cam and stroking. She sat atop a long dildo that she grabbed fro
m the side, and lined it up with her ass, before sliding it inside her with ease. The following moan from her left me ready to shoot my load all over the bed.
“Yes,” the cam model moaned in a delicate whisper.
The familiar chiming sound of tokens and “tips” rang off as the audience watching the cam model sent her money for her lewd act. The fact that I hadn’t ever supported the model with a tip or a gift, made it even stranger that she would randomly find my profile pictures and fawn over them. I didn’t think much of this, though. Instead, I stroked my cock until I felt the incredible tension in my balls. The power rocketed up my shaft and I exploded, shooting one long rope after another of my hot, white seed.
The cam model did just the same, cumming endlessly while the massive dildo had disappeared deep inside her tight little ass. I watched, hypnotized as her blonde hair bobbed along with her breasts and I imagined my cock in the place of that dildo. I wanted to punish the cam model for being such a naughty little whore. She walked around in public all day and night, leading everybody to believe that she was a woman. But she was hiding something very naughty, and the thought singed my mind.
I was hooked after that. Though, I couldn’t help but feel a small pang of tension each time I saw Jessica after this, which admittedly, was only once in the following few days.
She seemed to be the busy type; always gone here or there. Each time I came home, her beat-up little car was nowhere to be found. It was only in the late hours of the evening that I saw the light beneath her door.
I wondered if I would ever run into her until one evening, I did.
It was late, and I had just started to get a little too liberal in my downstairs office; a few sips of vodka will do that to you. I knew I couldn’t just pull out my cock and start stroking right there, for fear that Jessica might come down into the kitchen and hear me. So I told the cam girl I would be back, and decided to head upstairs. This worked well, as she was about to restart her computer, which had apparently been giving her issues.
I shut my laptop and started through the dark kitchen, with the computer beneath my arm. I was just coming around the counter in the middle of the kitchen when I saw the fridge open and reveal Jessica standing in front of it. She was completely topless and nude, with her incredible breasts hanging out in the cool fluorescent light. If the obvious tent in my pants hadn’t been hidden behind the kitchen island counter, she would have undoubtedly seen my cock rip a hole right through them upon seeing her perfect breasts.
“Holy fuck,” I uttered, upon seeing her gorgeous naked body.
“Oh shit,” Jessica gasped as she grabbed a beer from the fridge and slammed it shut. The kitchen was dark again, but I could hear her laughing in embarrassment.
“Shit, Jessica. I’m sorry, I really didn’t mean to…” I started frantically.
Jessica only giggled, though.
“Mr. Stevens, don’t worry about it. I doubt it’s the first time you’ve seen boobs,” she laughed.
I was admittedly surprised by this nonchalance. The women I’d known would not have been so careless if they had been caught naked. Though I didn’t see all of her body, I figured catching full glimpse of her naked breasts and nipples – hard from the cool air of the fridge – would have left her quite unsettled.
“Hope you liked what you saw,” she said before hurrying off out of the kitchen. In the dim light, I could barely make out her perky naked ass bounce with each step as she covered her crotch and made up the stairs.
“Fuck,” I whispered and shook my head in total disbelief.
The next morning I ran into Jessica again. She was clothed this time, but wasted little time in reminding me of what had happened the evening before.
“Sorry about last night,” she said in a cool and casual tone.
“What? Oh, don’t worry about it,” I said, as I hurried through the kitchen, grabbing my coffee and trying to make an early meeting.
“I um… I hope I didn’t make anything too weird,” she said. I couldn’t help but notice her skimpy little outfit; a tight (as usual) cute cotton shirt with a low neck line and a pair of tight denim shorts.
I shook my head and laughed. “No problems here,” I said. “This is your house, too, and I’m pretty laid back. You can do what you like. If you’re a nudist or whatever, well, I’m not going to stop you.”
Jessica laughed at this, before pointing against her lips and giving a small hum. “I never thought about that, but maybe I’ll take you up on your offer.”
After a moment, she appeared a bit more serious and came around toward me by the fridge.
“I um… I’m not a nudist, per se. But sometimes my work requires me to be naked, so if you happen to run into me again, I’m sorry in advance.”
“You don’t need to apologize,” I assured her.
“So you liked what you saw, huh?” Jessica asked.
I couldn’t believe that a stunning, knockout of a college girl like Jessica had decided to rent out my bedroom. But more than that, I couldn’t believe that she seemed to drop flirty little hints here and there that she was greatly enjoying my company. It all seemed too good to be true, and had to have come with some kind of a catch. I brushed down my blue, long-sleeve shirt and adjusted the dark-blue tie that had been giving me issues ever since I bought it a few days before.
Jessica, without warning, came over and re-tied it. Her quiet concentration was sexier than anything she had ever done; her crystal green eyes shimmered as they darted here and there, matching her pursed lips in her quiet concentration.
After a moment, she tugged the tie down and brushed my shirt. “There,” she said with an enthused sigh.
“Hm, thanks,” I said. “I didn’t expect you to know how to do that.”
“Well, I…” Jessica started, before stopping herself for a moment. “Uh, I used to work in a suit store.”
“I’ll bet you sold your share of suits,” I said with a wink. I felt as though I was growing a bit too casual with the young woman, though, and retracted. I made sure to let Jessica know right then, that I would be home late that evening.
“I’ve got a date tonight, so it’ll be like… ten or eleven. Just remember to lock the front door behind you if you get back before I do.”
“A date?” She asked. “Who’s the lucky girl?”
“No clue, actually. I’m being set up with by a couple of my buddies,” I said, and loathed to admit.
“I’m not exactly hurting for women or anything. They decided a few weeks ago though, that I need to get hitched ASAP. That’s what happens when all of your friends have recently gotten married. You start looking like the odd one out, and they want to drag you into their little club,” I explained with a laugh.
“Hm,” Jessica said with a cocked brow.
“What?” I asked, taking a quick sip of my coffee.
“I didn’t figure you for the domesticated type. You seem like you have some sort of… suppressed… I don’t know. I can’t put my finger on it,” she started. “Oh well. I’m being way too weird right now.”
Jessica ran off up the stairs and our next few interactions grew increasingly risqué in this way. She didn’t seem to have any boyfriends or guys around that I was aware of, which felt really strange. A girl as gorgeous as her and as charismatic as her would normally be fighting them off with a stick.
The final sign that I was in over my head arrived a few days after my blind date, which, compared to the fun I was getting from my sexy stranger on the cam-site, ended up boring me more than anything. As weird as it was, I was becoming increasing bored by the fact that the girls I was hooking up with, didn’t possess that little extra something that I was starting to expect.
I would hook up with women and eat out their tight little cunt happily, but it wasn’t the same as the fantasy I had built with my transsexual slut on the cam-site. It didn’t help that she was now sending me flirty little texts here and there. I knew that I shouldn’t give away my phone number like that, but
I couldn’t help it; she held a spell over me.
When I walked lazily to my mailbox the following Saturday morning and opened it up, I found something quite unexpected. I then realized that Jessica had something up her sleeve, but I wasn’t sure.
“Uh, is this yours?” I said, setting the sex-sleeve toy down on the counter. The mail had done a terrible job of delivery, leaving half of the toy sticking out of its packaging. The name on the package was Jessica S., which had already indicted her to the ownership.
“Oh, um… Yes, that is mine,” she said, slightly taken aback. This was a bit confusing, given her usual carefree approach to all things sexual, especially when they concerned her naïve landlord.
I looked down and studied the toy; it was a tubular silicone toy, mimicking anal sex. The end had an opening at the end that was detailed like a real asshole. I looked back up, and simply hoped that the fire in my eyes hadn’t come across as too obvious. I couldn’t help but think of fucking my new, dirty little cam-slut in her ass as I saw the toy.
Jessica was unusually quiet, and after a moment finally took the toy in her hand and whispered, “I’ll take that. You probably won’t need that.”
I wasn’t sure what she had meant, until I logged into the cam-site later that evening, and there it was. My cam-stranger transsexual was stroking her cock with that very same toy. My heart raced and my breath grew short. There was no way, was there? It all came together.
I turned off my cam and headed downstairs to the kitchen to make a drink, hoping it would help me process what was going on. As I passed Jessica’s door, I heard the faintest whispers of pleasure.
Within moments of grabbing a drink, Jessica came downstairs with a smile that told me everything I needed to know. The cat was out of the bag. My dirt little cam slut just so happened to be the girl renting my bedroom, and she knew it long before I did.
I set my drink on the counter and shook my head as we shared one of those rare moments where nothing needed to be said; eye glances were enough to tell a novel’s worth of revelation.
“So…” I started, trying not to feel too guilty that I’d been strung along in secret by my own housemate.