Pinky Surprise

The Joys of Modern Technology

I clicked the green button, and suddenly her video window was there on my desktop. She held up her phone for me to see, gave it a kiss, and then winked at me as she reached down between her legs with the phone.

She was sitting at her desk at work. I could see her office behind her, the window with a view of trees in the park, and a bookshelf full of binders. She was wearing a button-up white shirt with a camisole on under it, and a black skirt.

I couldn’t see it, but I knew that her desk was in a semi-private office near the entrance to her workplace. There was a large window next to her door, where she sat facing the hall. Anyone walking in or out had to walk past her office.

I tested our situation immediately by sending a text to her phone. After a second, I didn’t hear anything, but I saw her visibly startle and then blush and look at the camera.

“God, I nearly jumped out of my seat. I’m going to have to be careful,” she typed into our chat window.

“I’m going to keep you jumping all day,” I replied.

True to my word, I would send her a text every 15 or 20 minutes. She had agreed to keep her phone under her skirt, pressed against her clit all day. After awhile, she got pretty good at not reacting so that anyone but me would notice. But I could see the slight stiffening of her posture, or a momentary pause in her typing.

Once, I heard a coworker come in to start chatting with her and I quickly sent a text. She didn’t bat an eyelid, though I saw her reach over to grip the edge of her desk, and when her coworker left, she glared at me. I sent her three texts in a row for that.

She would have to leave her desk to talk to someone or go to the restroom, but she always put the phone back. I trusted her, but I still sent a test text shortly after she sat down each time, just for fun.

As the day progressed, I started upping the ante. I sent several texts in a row, or I would actually call and let her phone ring once or twice. The longer vibration from the calls would usually leave her slightly flushed and biting her lip.

Around 4, her boss walked in to discuss something. After a second, I sent a text.

No reaction. I sent two more texts.

Still no reaction. She was nodding patiently as her boss kept talking.

I dailed her phone and let it ring once… twice… three times… FOUR times… voice mail. I can’t be sure, but I think I saw her breathing quicken towards the end.

I wait a second and dial again. Once more, it rings four times and goes to voice mail. She seems to be trying even harder to avoid reacting, sitting primly, with her hands folded in her lap.

I give her a moment’s respite, and then dial again. While it’s ringing her boss walks out and she immediately turns to her computer and looks at me through the camera. “Please,” she mouths silently.

I hang up. She takes a ragged breath and closes her eyes, centering herself, and I dial again.

I small whimper escapes her lips and she grips the desk on either side of her keyboard tightly. Her eyes are closed and she breathes deeply as it rings and rings between her thighs.

As I hear her voice mail prompt start again, she stands, smooths her clothes down, grabs her phone and walks away.

10 minutes later, I get a text: “Had to go to the bathroom. Panties soaked. Took them off. Be home in 30 minutes.”

I grinned, closed my laptop and walked out of my office to follow her home.

Meeting Tease

The room was crowded, and the meeting was long and boring. I reclined in my chair and looked around the room. Most of my coworkers were seated at the long conference table along with me. There weren’t enough seats, so anyone who showed up too late to sit were standing around the perimeter of the conference room. A few had hopped up on the counter running the length of one wall.

As my eyes scanned across, I realized that I was looking straight up Tricia’s dress. She was wearing an orange sundress that ended above her knees. Her legs were just barely parted, and I couldn’t quite see anything, but I couldn’t help trying. As if she sensed me looking, she suddenly crossed her legs, and I looked away, continuing my sweep around the room, though I was no longer really looking.

As our boss droned on, my attention kept drifting back to her legs. I was praying she would shift, or cross her legs the other way, and I would catch a glimpse. For what seemed like an eternity, I kept stealing quick glances to my left… and it was perhaps inevitable I would get caught.

As I glanced over one more time, I realized she was looking straight at me. Quickly, guiltily, I met her eyes, expecting anger. Instead, I found an amused look on her face, and then she slowly, deliberately, uncrossed her legs. For a moment, before she recrossed them, her legs spread a bit wider than she needed to, and I saw all the way up her thighs to a pair of black mesh panties.

I felt an immediate surge between my legs, and then the moment was over, as quickly as it had begun. Her eyes were back on our boss, her legs crossed as through nothing had happened. I shifted uncomfortably in my seat and tried to focus.

Cumming in the Dressing Room

While no one was looking, she grabbed my hand and pulled me into the dressing room with her. We were at one of the more upscale clothing stores at the mall, where the dressing rooms are in a little hallway, and have full-length doors. We weren’t exactly isolated, but no one could see us, and if we were quiet, probably no one would bother us. I had been following her around the mall all morning, and I had been getting pretty bored, but as she pushed me against the wall and kissed me, I realized that she had really just been looking for the right dressing room.

“You’re crafty,” I whispered, and in reply she told me to sit down and watch. I sat down on the bench, and she hung up the clothes she had grabbed to get us into the dressing room. Then she turned around and started slowly gyrating while she started undressing. She was wearing a blue button-up shirt that snugly fit around her c-cup breasts. Her tan skirt was flared at the bottom and came to just above her knees, and she was wearing her boots with the big heels that brought her almost to my height.

Unbuttoning her shirt all the way, she slipped it off, leaving her standing in a thin white tank-top, through which I could clearly see her bra. It was also white, mostly satin with some decorative lace bits on the straps. She turned around to hang up her shirt, and I admired the way her hips swayed back and forth in the skirt.

As she turned back around, she ran her hands up her sides to squeeze her breasts, grinning at me as she danced. She did a slow spin in place as she pulled the tank top up over her head, and I looked her up and down. Dropping the tank top to the floor, she cupped her tits again, this time biting her lip slightly as she slipped one hand inside her bra to tease her nipple.

I moved to stand up, and she shook her head, and then slowly, deliberately undid the buttons of her skirt. As it opened, I could see she was wearing a pair of panties that matched her bra. When she turned around and slipped her skirt off, I could see it was a thong. I reached down and rubbed my stiffening cock through my jeans. This was starting to turn me on.

Hanging her skirt on the hook with her shirt, she turned back to face me and smiled when she saw what I was doing. Wearing just her boots, bra and thong, she stepped forward and leaned down to kiss me deeply. Her hands reached for the bottom of my shirt, and then pulled it over my head. When she bent over to unbutton my pants, I kicked my shoes off, and helped her slide my pants down around my ankles, so I could kick them off too.

As she straightened up, she lightly ran her hand along my cock, straining against my boxers, and then stepped back, resuming her slow gyrations. I could see her nipples pressing through the thin fabric of her bra. As she turned away from me again, I stared at her ass while I quickly peeled my socks off.

Still facing away from me, she reached behind her and undid the clasp on her bra, which she slipped off and let fall to the floor. Turning back, she had her hands covering her breasts, squeezing and massaging them lightly. Then she ran her hands up into her hair, and I felt my cock get harder at the sight of her dark pink nipples, erect and rising from her areola, crinkled and contracted to the size of a quarter.

As she watched, I pulled my boxers down, and started slowly stroking my cock. She looked pleased, and quickly bent over, wrapping her lips around my head. The feel of her tongue on my skin and the sight of her breasts hanging free caused my erection to swell, and she moaned quietly in response.

With one final swirl of her tongue, apparently satisfied that I was hard enough, she stood up again. Turning away from me, she began sliding her thong down with exaggerated slowness. Bending over as she went, making sure I had a clear view of her ass and pussy. She was ready for me. Her lips were parted slightly, and I could see that she was soaking wet.

Before she could step out of her underwear, I stood up, still stroking my cock with one hand. I grabbed her hip with the other and with one quick movement, plunged deep into her cunt.

I heard a startled intake of breath from her, and then she grabbed her ankles and rocked back, pushing me deeper inside. I squeezed her hips, and holding her tightly, started fucking her in the dressing room.

Bent over like that, her pussy was tight around me, so it was hard to stay quiet. Judging from her ragged breathing, it wasn’t easy for her either, but other than a muffled squeak or moan every now and then, the only sound was a quiet slurping.

After a few minutes, she let go of her ankles and turned around to lean against the bench. I swiveled with her, and resumed fucking her right away. Looking down, I could see some of her pussy cream around the base of my shaft, which turned me on even more. Looking in the mirror, I could see her tits sway back and forth with each thrust. Her head was hanging down, her lips open, breathing heavily. Her eyes were closed as she focused on the feeling of my cock sliding in and out of her body.

She was tightly gripping the bench with one hand, but was reaching up between her legs with the other hand to rub her clit. Her breathing sped up, and I tried to match my speed to her hand, which I could feel tickling my balls. I could feel my orgasm building, and I was hoping she was getting close when all of a sudden I felt her body tense. I looked in the mirror, and her eyes were wide open, staring right at me. I felt her pussy clench slightly around me, and she broke her silence to whisper my name.

That was all it took to push me over the edge, and then I was holding her tightly, pressed as deeply into her as I could. Just as her pussy stopped twitching, my cock started spasming, pumping my cum into her. My whole body shook with each spurt, and as the orgasm faded, I ran my hand up her back.

She slowly straightened, and turned to face me. I wrapped my arms around her, and we kissed desperately, pressing our bodies together. After a few moments, I sat back down on the bench to catch my breath, and I watched as she carefully got dressed again. After a minute I got dressed, too, but when we were done, there was still one article of clothing lying on the floor. Picking it up, I saw it was her thong. She grabbed it and put it in her purse, and whispered in my ear that she was going without panties so she could walk through the mall and enjoy the feeling of our cum all over her pussy and thighs. The fact that no one would know about the mess just under her skirt would turn her on even more, so she warned me I better be ready to fuck her again when we got home.

Taking Advantage of Her

She had too much to drink at the bar — hell, we both did — and I walked her home. More like carried her home, really. When we got inside, I walked her into her bedroom, intending to drop her there and then go home. But when she fell onto her bed, her legs were spread open and her skirt had ridden up a bit.

I figured, what’s the harm in a quick peek? I might never get a chance to see her panties again, so I leaned down and looked up her skirt. It looked like she was wearing some sort of dark blue panties, but I couldn’t really see very well. She looked thoroughly passed out, but I was still nervous as I lifted her skirt further up. Still not much of a view. Taking a deep breath, I slowly spread her legs further apart, and was rewarded with a nice view of her thong.

I was incredibly aroused by the situation. Some part of my brain knew this was a bad idea, but another part said “You’ve come this far, why not go a bit further?” So I pulled the straps of her tank-top down to get a look at her bra. It was also dark blue with a bit of lace on the cups to match her panties (planning on some action tonight, I thought). Watching her face for any sign of a reaction, I lightly ran my finger along her bra, tracing down her chest between her tits. When she didn’t respond at all, I slowly hooked one finger under the right cup and pulled it down. Her nipple was soft, with a large areola that gently faded in color to match the pale skin tone of the rest of her breast. I ran my finger around her nipple, and felt it harden slightly under my touch.

As if in reply, I felt a surge of blood in my cock as it hardened, and without thinking at all, I leaned forward and took her nipple into my mouth. I sucked deeply on her tit, running my tongue all over, feeling her areola pucker and contract as her nipple hardened between my lips.

I let go of her tit with a wet pop, and stood up. She was spread lewdly out on her bed, legs over the corner, skirt pull up over her waist, and one tit popped out of her bra. Her arms were spread at her side, and her lips were open a little. She let out a tiny little moan, as if she could sense my gaze, and shifted slightly on the bed.

I should have left at that point (I should have left much earlier, actually), but instead I slide my hands up her hips and found the waistband of her underwear. It wasn’t exactly graceful, sliding them off, since I had to pull them out from under her without her help, but I got it done without waking her, and then I was looking at her shaved pussy.

To be honest, I was shocked. I really never would have pegged for a clean-shaven type of girl. I assumed I would find a neatly trimmed bush, or a landing strip at most. But there was her bare cunt, glistening at me.

Yes, glistening. She was soaking wet. I have no idea why. She had been flirting with a guy back at the bar, maybe that’s what got her going. Or maybe on some level her body was responding to what I was doing. Hell, maybe she was dreaming about the guy at the bar, and my touches were just feeding into that. Whatever the reason, there was no mistaking it.

Hardly believing what I was seeing, I spread her legs further. Her pussy lips opened a little, and I could see her clit poking out from its hood. I ran a finger down the length of her lips, and then, without really realizing what I was doing, I leaned forward and took a taste.

I ran my tongue from the opening of her pussy up between her lips and over her clit. Then back down again, and I pushed my tongue as deep into her as I could. She tasted so good, like pure sex, and my cock was rock hard, straining at my pants.

Then suddenly I was standing, undoing my pants. I knew this was wrong, but at that point, nothing could have stopped me. It seemed like it was meant to be. I had one hand on her ankle, holding her leg up over my shoulder, and the other wrapped around my cock. I leaned into her, rubbing the head against her lips, which parted invitingly around me, and then I slid into her.

I could feel her pussy wrapped hotly around the length of my shaft, and I slid it back out. Then slowly back in, and quickly back out. Then I was pumping in and out of her. Her pussy seemed to contract, gripping me tightly. I looked at her one free tit moving back and forth as I fucked her. She was breathing deeply, completely unaware of what I was doing — but her body seemed to know exactly what was happening, and invited it.

There was a wet slurping sound as I continued to thrust into her, and the smell of her pussy filled the room. I was dizzy with the situation, and suddenly I realized I was about to cum. It was all I could do to reach down and grab my cock. I pulled out, but I had already spurted once inside her, despite my best efforts to hold off. My head was extremely sensitive, and I felt my hot cum on my fingers as they slid up, brushing over her clit. Realizing the damage was done, I slipped the head of my cock back into her cunt, stroking my shaft as I continued to pump my cum into her seemingly eager pussy.

When I was done, I stepped back, and looked at the mess I had left. Her discarded panties were lying on the floor, her top was tugged down over one tit, and her skirt was bunched up around her waist. My cum was everywhere. One spurt had shot upwards, running down her hip from her belly. Her pussy lips were spread apart, cum smeared across them where my hand had been rubbing as I jerked off inside her. As I watched, more cum silently dripped out of her, running over her ass and leaving a wet spot on her sheets.

Quietly, I buttoned my pants back up, and then pulled her panties back over her feet and up her legs. Again, it was tricky getting them over her hips, and when I was done, the dark blue fabric clung to her wet pussy. I did my best to straighten her clothes, and then slipped out the front door.

Morning Wood

She gasped when I brushed my hand over her nipple — As much from surprise as from pleasure, I think. We were both half-asleep, lounging in bed. She was an old friend from high school, visiting home for the weekend from her out-of-state college. We were planning to spend the day together, but she had shown up around 7am after her train got in, and I normally didn’t get up until noon on the weekends.

In high school, we had been pretty close, even though we never dated, and we had even slept in the same bed a few times before at all-night parties. So when I suggested we climb back into bed for a few hours, she didn’t seem to mind. She took off her sweater and corduroy pants and climbed under the blankets with me. She snuggled up against me for warmth, lying with her back to me, and my arm around her middle. I was wearing boxers, and she was just wearing her underwear and a thin tank top.

For a few hours, we did just sleep, but over time I became increasingly aware of her body. She was about the same height as me, just a little bit shorter, and very skinny with small boobs. I remembered in high school she didn’t even wear a bra most of the time. I remembered one time when I caught a peek down her shirt as she bent over in front of me in a loose-fitting shirt, and I could clearly see her nipple. Thinking about that, and with her body pressed up against me, I started to get hard.

I’m not sure if she could tell. It seemed pretty obvious to me, my erection pressed into her ass, between the swell of her cheeks. I tried not to move at all, afraid she would suddenly notice. So far, she hadn’t reacted at all, and her breathing was still deep and even.

Eventually, it was too much for me. I lightly ran my hand up her chest, brushing my fingers over her nipple. I wasn’t sure what kind of reaction I would get, but the sudden intake of breath was followed by a slow exhale. Figuring that sounded like a positive reaction, I kept moving my hand up and wrapped it over her shoulder, pulling her closer to me. She responded by leaning back into me, putting more pressure on my cock.

Feeling more bold, I slid my hand back down her chest, teasing her nipple again. This time her reaction left me no doubt. She moaned softly, and reached up to grab my hand, cupping her breast. Pressing my hand firmly against her chest, I could feel her hardening nipple pressing against my palm through her shirt.

I pressed my hips forward, and she responded by grinding against me. My cotton boxers slid smoothly against her satin panties, and the feeling of my cock slipping up and down between her ass cheeks was turning me on even more.

I slid my hand out from beneath hers, giving her nipple one more tweak before I slid my hand down. Her tank top ended a few inches above her panties, and her skin was hot. I ran my hand along her hip, and then slipped my fingers under the elastic. Her breath quickened as I ran my fingers through her pubic hair, and she spread her legs slightly to let me reach further. Moving past her bush, I found she was already wet.

Her lips were already slick and my finger slid easily between them as she continued to grind against me. She moved her hips forward, stroking down my cock, and slipping my finger deep between her lips, teasing her opening, and then moved backwards, stroking back up my shaft, and sliding my finger up to her clit.

She moaned lightly and reached back to grab my head, pulling me forward where I started kissing her neck. I started moving with her, humping her ass while she rubbed her clit against my fingers. I had two of them now slipping between her lips, stroking along the smooth path to her pussy, rubbing her wetness all over.

She shivered and then pulled away from me slightly so she could slip her panties off. Quickly, I pulled my boxers off as well, and then we were pressed together again. One hand was under her body, touching her hip, and with the other I reached up and squeezed one of her nipples. Meanwhile, she reached between her legs, and positioned my cock at the entrance to her pussy.

She worked my head back and forth a few times, slipping it between her lips until it was coated in her juice, and then she slid down the length of my shaft. She was warm and wet, and I slipped easily into her. When I was buried to the hilt, we paused for a second, and then she started grinding her hips again, just like she had been doing before, only now, every move slid my cock in and out of her pussy.

The sensation was overwhelming, and I swear I’ve never been harder. It felt like my head was swollen larger than normal, and I could feel the texture changes as I plunged in and out of her cunt. Her lips were tight around my shaft, but around my head I could feel the smooth, velvety texture of her inner walls.

I groaned into her neck and grabbed her tightly. Her breath was coming in short, sharp gasps, and every few seconds she would reach between her legs to keep me from popping out. A few times I did, and she would run her hand down the length of my shaft before grabbing me firmly and putting me back inside her.

After a few minutes, she must have noticed my breath coming more rapidly, or felt my cock stiffen or something because suddenly she was whispering a frantic warning in my ear not to cum in her, because she wasn’t on the pill. She never stopped fucking me, she just said to tell her when I was about to cum.

It didn’t take long… A few seconds later, I gasped out a warning, and she suddenly rolled to the side, popping my cock out of her. I rolled onto my back, and reached down, figuring I would have to finish things up myself, but before I could, she had turned around and grabbed me, wrapping her lips around my head. She moaned impatiently and started swirling her tongue around while squeezing me. My initial shock passed quickly, and the sensation quickly brought me right back to the peak.

I groaned and then arched my back as I came in her mouth. She continued to make quiet little excited sounds as she sucked and ran her tongue around me. I had never cum in a girl’s mouth before, and the ongoing sensation as she sucked me off drew the orgasm out. She moaned happily as the last aftershocks hit me. I was staring at her as she let me slip out of her mouth, and she smiled as she reached up to wipe a bit of my cum from her lips.

“Well,” she said, “What are you gonna have for breakfast?”

Winning the Bet

“Remind me again why I’m doing this?” she asked as she leaned against the doorframe to her bedroom.

“You lost the bet,” I said, taking another swig of my drink. The cheap whiskey in the cola made me grimace as I finished speaking. I was sitting on the sofa in the living room of her apartment, with a nice buzz going.

“It just doesn’t seem right that I have to parade around in my underwear while you sit there fully dressed.” She stood up as she said this, swaying just a little bit.

“Hey, you lost the bet fair and square. If I had lost you would have made me run naked through the bar, now take your clothes off!”

“I’m not stripping for you!” she laughed, sounding insulted. “I agreed to model the contents of my underwear drawer, not do a striptease.”

“Fine, have it your way. First thing, I want to see what you were wearing at work today. I’ve always wondered what kind of underwear you have on.”

She raised an eyebrow at that and walked into her bedroom. I mentally kicked myself for coming on too strong. At the bar, we’d been flirting heavily, and she’d laughed when she agreed to my terms for the bet. Now that we were in her apartment, though, the mood had shifted slightly, and I was afraid she’d suddenly change her mind and decide I was a creep.

As I was thinking that, she walked back out of her room. The fitted white polo shirt was gone, as were her jeans. She was skinnier than I’d thought, with good-sized breasts. Her white cotton panties rode low on her narrow hips. She leaned against the wall with her arms folded beneath her bra, also white, but with a simple floral texture. She seemed amused and uncertain what to do next.

“Come on, don’t just stand over there, you said you’d model them for me. You’ve gotta at least walk over here and turn around so I can get a look at you,” I said.

She rolled her eyes, and launched into an exaggerated runway walk, stopping and turning a full circle in front of me, and striking a model pose at the end.

We made eye contact, and for a moment it was awkward, but then we both burst out laughing. Maybe it was the alcohol, but the whole situation was too strange to take seriously. I made a show of looking her over from head to toe, and she turned around and shook her ass at me as she walked back into her room.

“What should I put on next?” she called from the bedroom.

“Well, I don’t know what the options are… Why don’t you put on something you’d wear on a day when you’re feeling a little sexy?”

I heard her rustling around, and after a few minutes she came back out. She paused for a moment in her doorway, and then walked over to me. The white cotton had been replaced by black satin. The bra pushed her breasts together and up, giving some nice cleavage. The matching panties were cut high and rose over her hip bones. As she turned around in front of me, I looked down her flat stomach, along her smooth thighs, and up along the small of her back to her neck, where her hair was still tied in a simple ponytail. As she finished turning, she caught my eye and said “Is this what you were looking for?”

“Very nice,” I agreed. “Now why don’t you show me something you’d wear on a date?”

I watched as she walked back into her room, and quickly adjusted myself. I was starting to get hard, and I was hoping it wasn’t totally obvious. I took another sip of my drink and fidgeted uncomfortably on the couch.

When she emerged from the bedroom a few minutes later, I forgot all about trying not to be obvious. She was wearing a white mesh thong and matching bra. As she walked slowly towards me, my eyes roamed over her body. The bra was mesh on top and satin on the bottom, and I could just see the tops of her nipples. Through the mesh of the thong, I could clearly see her neatly trimmed landing strip of pubic hair.

She didn’t seem to mind the way I was gawking at her, and she turned slowly around in front of me. Stopping with her hands on her hips, she asked “What do you think?”

“Um, it’s very, uh, very attractive. I particularly like the mesh bits.”

“I can tell,” she said, with a quick glance at my crotch. I looked down and mentally cursed at the now obvious erection tenting my pants. I was terrified that at any minute, she would decide this game had gone too far and kick me out. Before I could say anything, though, she had turned her back on me and was striding out of the room.

I shifted around on the couch, trying to find a way to sit that would make my hard-on slightly less noticeable.

“So, what now?” she asked from the other room.

“Well, why don’t you show me what you would wear for a guy you were going to bring back to your place?”

Silence. Some part of my brain was screaming at me for being too pushy. Any second now, I thought, she’s going to say that’s too much, and get rid of me.

Then suddenly she was walking towards me again. But this time she wasn’t wearing anything at all.