Caught Napping

Posted in: Male Masturbation

Caught Napping

Generally security work is quiet, almost boring at times and especially on the midnight shift but every once in awhile there can be some excitement and not always security related. I was working the midnight shift at a fair sized post, it was a temporary post, the company was being bought out and this location was not going to be used any longer. We were there, essentially babysitting the building until everything was cleared out. All in all it was a very easy post; the main challenge was finding something to keep you awake through your eight hours.
I was the shift supervisor, there were two other guards under me, which allowed me a little freedom; I wasn’t stuck at one single spot during the shift, I could move about if I wanted to. The other two guards that I worked with was Tom, a cranky older man that was working just for something to do and possibly give his poor wife a break from him. The other guard was Sharon, an attractive young woman who was working security while her husband finished his schooling and she too was taking some classes. She was a nice girl, fun and easy to talk with and very nice looking. While the uniforms we wore weren’t exactly designed to show off someone’s features it was still, with a little imagination, easy to know that Sharon had a nice figure.
Sharon stood about five six and I guessed she weighed about one hundred and ten pounds. She had thick wavy chestnut brown hair that fell to her shoulders. The uniform consisted of a khaki colored button shirt, with dark brown epaulets and simple black slacks. While the slacks were on the simple and plain side I must admit that Sharon nicely filled hers out; they didn’t reveal an awful lot of her lower half but they weren’t bulging because of her either. Her top also concealed her chest, not completely, it was obvious that she had a nice sized bust; nothing overwhelming but nice for her stature. I will admit that on a few occasions while I was trying to find something to occupy my mind I allowed my thoughts to dwell on her; wondering what she looked like without that uniform on.
The incident that I most enjoyed happened one spring night. Sharon arrived a little bit before our scheduled start time and we all, the oncoming and the outgoing guards, were standing near the front door chatting. Sharon seemed a little sluggish as we stood there and I asked if she was okay. Stifling a heavy yawn she told me that her allergies were acting up and she had taken some different medicine for it and she was afraid it was making her very sleepy. I laughed and asked if she was going to make it through the shift. She laughed and shook her head saying she hoped so and then added that it might be a good idea to check up on her now and then just to make sure. I nodded and told her I would and I’m glad that I did.
There were three different spots throughout the building that we would occupy during our shift. Usually Tom took the desk at the front entrance, Sharon tended to sit back at the loading dock and I would usually park myself in what use to be the security office, from there I could monitor the exterior of the building with the video monitors that were posted around the building; seeing that there was less then a dozen employees still working there and that was during the daytime, there really wasn’t too much to watch for any of us. Actually one guard could have monitored the whole building from either the front desk or the office since there was computer monitor there. But the client wanted to have three guards there watching an almost empty building and it was easy work so we didn’t complain.
It was around three and I was feeling rather bored, I had forgotten to bring something to read and talking to myself was not that fun, so I decided to get up and stretch my legs. Being the shift supervisor I had the option to make occasional foot patrols so I decided that was what I would do.
Basically I just wandered around the building and then I recalled what Sharon had said about hoping she could remain awake and decided I would do as I had promised and check in on her. I also thought that I might spend some time with her just talking; would be a hell of lot more interesting then talking to myself or Tom.
The storeroom seemed a little creepy as I walked through it; it was dimly lit and pretty empty, the perfect setting for a good horror movie. The guard post was at the back of the storeroom where items were brought in or shipped out. There was a desk off to the side near the two bay doors and that was where the guards would usually sit. As I walked through the area I could hear a radio softly playing; while company policy was that there were to be no radios on any post, it was a rule that was frequently disobeyed. I wasn’t going to say anything to Sharon about it, for one reason I had a radio of my own in the office that I listened to so I wasn’t about to tell her she couldn’t.
I came around the end of a row of shelves and saw Sharon seated over at the desk. I chuckled when I saw her; she was leaning back in the chair with her head back. I tried to make as much noise as I could as I walked over towards her but there wasn’t anything that I could bump into or move to make noise with. I also coughed and clear my throat just to alert her to my approach but she didn’t stir. When I reached the desk I cleared my throat a shad louder then normal and she still didn’t respond.
A little concerned I stepped around and softly called her name. I frowned as I studied her as I moved around the desk, making sure she was still breathing and saw her chest rising and falling which eased my brief concern. Her eyes were closed and her head laid back and she was breathing steadily and deeply. While having the radio I would overlook being asleep while on duty was definitely not something I could overlook. Company policy called for any officer found asleep while on duty to be written up on the first offense and any further violations could and usually did result in termination. I wasn’t going to be so by-the-book for a couple of reasons; one, this wasn’t a premier account and two, because I rather liked her and didn’t want her to get in trouble.
I lightly touched her shoulder and again spoke her name and she still didn’t respond. She was most definitely out, sound asleep. I chuckled and shook my head as I sat down on the edge of the desk watching her. I had never met her husband and she had only spoken of him briefly during the few times we had actually spoken, but I thought what a lucky guy he was to have such a pretty woman for a wife. I allowed myself to let my eyes move over her figure as she sat there seeing that she wouldn’t know I was having a nice long look at her. That was something our employer always seemed to stress; what was sexual harassment and that it would not be tolerated. I was sure that my eyeing her would probably somehow violate the rules, but I decided to enjoy the view seeing that she was asleep and since there was no one else present no one would know.
As I stood there watching her I wondered if she would wake up on her own or if I should wake her. I chuckled as I imagined the good natured ribbing I could give her if she did wake up while I was there. Watching her was much more enjoyable then watching the video monitors back in the security office and I decided to enjoy it for as long as I could. This was the first time I really had had to look at her. As I ran my eyes along her figure I realized that I had never seen Sharon dressed in anything but her security uniform. While her uniform didn’t exactly display her figure it didn’t totally hide it either. As I looked at her, well okay her breasts, I found myself wondering what she looked like in things other then her uniform, such as jeans and a casual top, a nice dress, a bathing suit and a negligee. I had to admit that her husband was one lucky guy for he had probably seen her in all of those things and less. I told myself that he was either a fool or very serious about his schooling to let such an attractive women like her to be working at night while he was home asleep. Surely he couldn’t be tired of making love to such a fox as her; if he was he was definitely an odd fellow.
My eyes had become riveted on Sharon’s nice bust, I enjoyed watching it steadily rise and fall with each breath. Soon I found my thoughts locked onto her mounds, along with my eyes. I began to wonder how they looked and how she liked them fondled. The professional part of me was telling me that I should stop and go back to the security office before I did something wrong. The rest of me told that part of my mind to shut up that this was too good to walk away from.
Although I knew there was no one else, other then Tom, in the building I still nervously looked about the area. I licked my surprisingly very dry lips as I moved over next to Sharon. I was surprised to realize that I was holding my breath as I stood there watching her, waiting to see if she responded in anyway. When my chest muscles began to ache slightly I took a shaky breath fearful that I would somehow rouse Sharon but luckily I didn’t.
Once more the professional in me pointed out that I could get in a hell of a lot of trouble if I tried anything and that the best thing to do would be to go back to the security office or at least wake her. Luckily the rest of my brain told that part to shut the fuck up. I again licked my lips and hastily rubbed my hands together as I stared down at her.
Well, I knew if I got caught I would definitely be fired and would probably never work in private security again; but I decided what the hell, a chance like this would probably never present itself ever again. I leaned towards her and reached out, lightly touching my fingertips to her breast. I kept my eyes trained on her pretty face to watch for any kind of response, ready to pull my hand away and step away quickly. Luckily she remained fast asleep.
I took another shuddering deep breath as I lightly touched her breast, enjoying the feel of it lightly pressing against my fingertips when she breathed. Slowly I moved my fingertips over the front of her wonderful mound. As I did I wondered how many men had Sharon allowed the pleasure of playing with her breasts; besides her husband and now me. I knew I would never find out, but I couldn’t help but think about it.
Slowly I slid my fingertips over her breast until I felt the edge of her bra through her top. I then followed the edge of her bra up to where the shoulder strap attached to the cup and then slid my fingers down along the cup into her cleavage. As I did, I muttered a soft prayer that she remain asleep for at least for a little bit longer. I pushed my finger forward so I was touching, through her blouse, the smooth skin between her breasts, my finger resting on the small piece of material that connected the cups of her bra. I paused for a long second and then traced the edges of the other cup of her bra with my fingertip. I moved my finger along the lower edge of her bra, enjoying how my finger lightly rubbed against the underside of her breast as I did. I thought it would have been a pleasant discovery to find out she wasn’t wearing a bra and wondered if she ever did go braless. I would not have objected if she had, but I also knew that I couldn’t suggest it.
Reaching the spot between her breasts I again slid my fingers up onto her breast and rubbed my fingertips over the front of her mound hoping to locate her nipple. The material of her blouse and bra effectively concealed the location of her nipple, but I definitely attempted to find it. I made sure that I moved my fingertips over ever inch of her nice mound, across the gentle swell of her upper breast to the nice full underside and along both the inside and out side. I then slid my fingers over and gave a similar thorough examination of her other breast.
I chuckled softly as I continued to rub Sharon’s breast wondering how her husband would react if he found out what had happened to his wife while she was at work; not pleasantly I’m sure. There was something wickedly exciting about fondling Sharon, another man’s wife, without his knowledge or approval, but then again I didn’t have Sharon’s consent or knowledge either. That somehow made it even more exciting that I was playing with her wonderful boobs and she didn’t know anything about it and probably wouldn’t. It would be my little secret and one I was quite happy with.
Gaining some confidence I cupped my hand fully against Sharon’s breast, enjoying the way it filled my hand. I gave it a slow gentle squeeze, grunting softly as I did. Again I couldn’t help but wonder just how many men Sharon had allowed to play with her boobs. That and how did she liked these lovely mounds of hers played with; did she liked them to be gently fondled and caressed or did she like them to be manhandled, at least slightly. I knew I would probably never know but I would have been quite willing to have her tell me how she liked them treated and then do as she wanted.
I gripped her mound for a long moment, warning myself to not be too rough; I definitely did not want to wake her up. I gently pressed her mound up on her chest and then released it, letting it settle back down. I shifted around so I was standing in front of her and reached out and took hold of both of her breasts. I gripped them firmly and then slid my hands to the outsides of them. I slowly, firmly pressed her mounds together in the middle of her chest and held them there. Slowly I rubbed her firm mounds against each other and then let them slip back to their normal position. I then firmly pressed my fingertips against her breasts and began to rub them again, hoping that I was near her nipples.
As I rubbed her tits I wished that she had been given one of the newer styles of shirts; the ones that had the buttons sown on and a zipper front with a Velcro strip along the shirt so it looked like it was buttoned when actual it was zippered. It would have made opening her top a lot easier. I stared at the buttons on her blouse debating on whether I could unbutton them and no one, well Sharon, not know I had. I knew I should stop now, but this was such a fantastic opportunity that I couldn’t let it pass. I gave Sharon’s boobs one more quick squeeze and then released them.
Shifting closer I reached up and began to fumble with the top button on Sharon’s uniform. I shook my head as I fumbled with the damn thing, I had never had such trouble undoing a button before, I told myself. Immediately my mind responded with, yeah but this was different. I cast an angry glance at Sharon whispering a mild oath at the office for not giving her a better top; one that was easier to open. My mildly aching chest reminded me again that breathing was a good thing to do regularly. As I took a shuddering breath I couldn’t help but chuckle at how embarrassing that would be to pass out because I held my breath too long while I was feeling up Sharon.
Finally I got the damn button undone and quickly moved to the next one. As I fumbled with that one, my fingers seemed strangely stiff and clumsy, I briefly thought about just ripping her blouse open, but I knew that would be a little too hard to explain. As I messed with the button I continually alternated my eyes between that button and her face watching for any sign that she was beginning to wake up. A small voice pointed out that I would also have to button her top back up but I quickly dismissed that; I would worry about that when I had to. After I got the first two buttons undone I paused to quickly open her top a little and uncovered her upper middle chest. Again I couldn’t help but wonder about her husband and the idea that while he was home asleep I was unbuttoning his wife’s top so I could continue playing with her breasts. Sweet dreams.
I got her blouse unbuttoned down to the spot between her breasts and again I paused to spread her blouse a little more and uncover more of her chest and part of her bra. She was wearing a plain flesh toned bra; I muttered a soft complaint asking why she couldn’t have been wearing a front latch one, just to make things a little easier. I held the edges of her blouse in my fingers and lifted it a little ways from her chest and gazed inside of her top at her bra-covered boobs. Yes they looked delicious, not too big and definitely not too small; yes she probably looked fucking fantastic in a bathing suit, probably even better out of it.
Quickly I unbuttoned her blouse down to her waist and eagerly forced her top open and uncovered her upper body. I sat back and let my eyes soak in this wonderful view of her upper half, almost completely bare to my view. I leaned back towards her and hooked a finger inside one of the cups of her bra and pulled it forward. I then placed my other hand flat against her chest and slipped my hand inside the cup of her bra. Again I couldn’t help but think of how many men Sharon had ever allowed to play with her boobs.
I groaned softly when my fingertips found her nipple. Tenderly I began to toy with it, rubbing it about and lightly pinching it between my thumb and middle finger. I was pleased as I felt her nipple begin to stiffen; she might be asleep, but her body was responding appropriately. I knew I couldn’t pass the chance to get a look at her breast, I intended to play with it as much as I could but I also wanted to see them.
Again I muttered a complaint to Sharon that she should have worn a front latch bra and wishing there was some way I could get her bra off of her. I pulled my hand from inside the cup of her bra and ran my finger up along the strap and worked it over off her shoulder. I then hooked my finger just inside the cup of her bra and drew it over and uncovered most of her boob.
I stared at her bare pale mound for a long moment, again forgetting to breathe. Her breast looked full and firm, I doubted she really needed to wear a bra, at least not for support. Her semi-erect nipple looked to be about the size of the tip of her little finger and was surrounded by a small areola. Carefully I placed my fingertip on her nipple and rubbed it, causing her to moan softly and nearly causing me to swallow my tongue. I froze as I stared at her, mentally telling her to stay asleep. When she made no further noises I resumed rubbing her nipple, tracing the dark circle of skin that surrounded it. After a few seconds I gently pinched her erect cone of flesh. She again moaned sleepily but made no other sounds. I again pinched her nipple and this time slowly rolled it back and forth between my thumb and index finger. Sharon again moaned softly but this was a soft almost contented moan.
After a few more seconds I released her nipple and quickly uncovered her other breast. I again sat back to enjoy the view I had created. I mentally kicked myself for not having my cell phone with me; I would have loved to have been able to have taken a few pictures to remember this. Sharon was absolute fantastic vision sitting there; her head back, eyes closed, her blouse unbuttoned to her waist and her bra cups pulled aside.
As I stared at her I couldn’t help but chuckle as I thought about her talking to her husband after she got off, “Gee honey how was work last night?”
“Oh okay.”
“Anything happen?”
“No, nothing exciting happened.”
Yeah well maybe she wouldn’t think anything exciting had happened but little did she know or at least I hoped she wouldn’t.
Shifting next to her I leaned over and lightly kissed her stiff nipple. I then traced her nipple with the tip of my tongue. Gently I kissed her breast, occasionally licking her nipple. As I did I cautioned myself to not leave any marks; that would definitely be rather hard to explain. I enjoyed kissing all over her pale smooth breast. I eagerly sucked on her erect nipple.
I kissed my way across her chest to her other breast and gave it a similar work over; kissing, licking and sucking on it for sometime. It was only my aching lower back that made me stop. I stretched and stepped back over in front of her, staring down at her. It definitely was going to be difficult to look her in the face after this and not recall this wonderful event, even if she wouldn’t.
Leaning back towards her once more I locked my thumbs and index fingers to her stiff nipples. Slowly, steadily I began to pinch her nipples and at the same time I slowly drew my hands back. She groaned after a few seconds, I had pulled her breasts forward somewhat so the weight of them was being supported by her nipples. I then released them and enjoyed the way they heavily settled back to their normal position of her chest.
I stood there with my hands on my hips watching her and allowed my eyes to move down from her breasts, over her partly visible belly, across her waist to her crotch. Again that damn voice of reason urged restraint as I stared at the area between her partly spread legs but I quickly decided that I had gone this far, I couldn’t stop now.
Leaning forward I carefully slipped a hand underneath one of her knees and moved her leg over and then did the same to her other leg, spreading them nicely but not too much. After I had, I ran both of my hands along the inside of her thighs, enjoying the feel of her shapely thighs. I wished there was some way I could remove her slacks completely, so I could get a look at her lower half, but I knew that would be too difficult a maneuver. Would have been enjoyable, but a bitch to achieve. Shaking my head with a little feeling of regret I again stepped to her side and resting one hand on the back of the chair I reached down with my other one.
As quietly as I possibly could I slid the metal slide clasp on her belt buckle over. I kept my eyes on her face watching for any kind of response as I carefully worked the end of her belt through the slide clasp. The occasional clanking of the clasp seemed incredibly loud and kept expecting her to open her eyes and scream bloody murder; luckily she didn’t. I laid the ends of her now undone belt aside and reached for the slide clasp on her black slacks. I then searched and finally located the small metal tab on her zipper. Slowly I began to work the zipper down on her slacks. Occasionally I had to reached won with my other hand and adjust her slacks so I could continue working her zipper down, her slacks was bunched slightly since she was seated. Finally I had worked her zipper down far enough, I laid her slacks open as much as I could and was rewarded with a small view of the baby blue panties she was wearing.
I grunted and shook my head as I gazed at that small piece of panty material again wishing I could completely remove Sharon’s slacks and find out the style of her panties; that is before I pulled them off of her too. Briefly I wondered if they were bikini cut or possibly a thong. Again I regretted not being able to remove her slacks; I would have loved to get an unobstructed view of her ass. The slacks the company issued definitely did not provide a flattering display of any of the women’s asses, unless they were very big. While they weren’t exactly baggy they left a lot of room for imagination.
Well, I decided, while I may not get a look at her ass I would at least get the chance to enjoy another part of her wonderful body. Placing my arm along the back of the chair I placed my other hand flat against her abdomen. I kept my eyes on her peaceful looking face as I slid my hand down along the warm smooth skin of her lower belly. I paused when the tips of my fingers touched the waistband of her panties and I pressed them into her flesh so I could work them underneath the waistband. I slowly moved my hand from hip to hip once I had wormed my fingertips inside the waistband of her panties.
I moved my hand back to the middle of her lower abdomen and then pushed my hand down deeper into her panties and between her legs. As my hand slid across the smooth skin of her crotch I realized that she was shaved smooth which made me wonder just what kind of a bikini she wore, probably a very skimpy one, but that would only be a guess. She moaned longingly as my hand moved between her parted legs and I stopped watching her closely. I could feel the moist warmth of her pussy and when she made no further movement I pushed my hand the last distance, feeling my fingers sliding along her pussy slit.
Sharon moaned longingly when I pushed my middle finger into her warm, moist and snug pussy. I groaned softly myself as my finger slid into her, enjoying the snug grasp of her pussy. I could imagine how wonderful it must feel wrapped tightly around a cock. Again I would have to imagine how wonderful it would feel. I briefly considered how I might get her slacks removed and her flat on her back, but the risk was just too great, although the reward would have been fantastic too.
Slowly I began to finger her and to my pleasant surprise she began to mildly grind her hips against my finger and groaned sleepily. Apparently, although she was asleep, I was getting her aroused. Well she was definitely getting me turned on too and luckily I was wide awake; at least one of us was going to remember this event. With a deliberate pace I fingered her increasingly wet pussy and making her occasional moan and roll her head side to side.
Stay asleep, I urged her as I continued to finger her. My pumping finger was making a soft squishing noise as it slipped in and out of her. I worked another finger into her and received a long, satisfied moan when I did. I watched her pretty face as her breathing began to pick up and her hips were grinding a little harder against my fingers. Suddenly she inhaled sharply and tensed and I felt her pussy quiver and then felt her warm, thick cream flowing down my fingers. I had gotten her off. I continued to finger her as she shuddered and let out a long moaning sigh and then went limp. After a few more wonderful moments of fingering her pussy I pulled my hand from between her legs.
Now it was my turn, I decided as I moved back in front of her. There was no way I could wait until the shift was over and I got to my apartment. And definitely not with her sound asleep in front of me and partly undressed. Quickly I fumbled with my pants and pulled my stiff cock out. I scooted closer to her as I began to jack off, while I’m sure it would have been more enjoyable to cum in her this was going to be incredible. I eagerly pumped my cock, pointing my cock at her as she sat there.
The fact that Sharon was someone else’s wife and the fact that I was going to cum on her and no one but myself would know it only made it more fantastic. Her husband would not know that while she was here at work and also sound asleep I had seen, fondled and sucked her breasts and then had also fingered her, bringing her to a climax and then shoot my wad on her. Oh yeah it had been a great night at work.
I groaned as I felt my balls beginning to tighten; I hastily muttered a silent plea that she stay asleep for a little longer and that Tom didn’t holler for me over the PA system. I tensed as I pumped my cock frantically, my eyes glued to Sharon’s lovely breasts. I groaned longingly as I felt my cum surging through my shaft. I shuddered bodily as the first huge glob shot out; it flew away and splattered on Sharon’s chest, right between her pretty breasts.
Not to brag but it was one of the largest loads I had ever shot, not that I really keep track of these things. I sprayed a good sized amount on her chest, getting a good amount on one of her bare boobs and some on her bra. I also directed some down at her belly, really hoping to hit her partly visible panties. I left a nice amount on her smooth lower belly and some did land on her panties and also a little on her pant legs. I sat there, leaning back against the edge of the desk trying to catch my breath and watching the thick whitish cum slowly sliding down over her skin.
As I watched my cum slowly sliding down her chest to between her boobs and over one of her boobs I considered leaving her as she was; a little perverted justice, instead of writing her for being asleep on the job. I decided that wasn’t a good idea, it might even get me into a hell of a lot of trouble. Still she looked very nice the way she was but I knew I had best not leave her this way.
After a few more moments I stuffed my now limp cock back in my pants. Shakily I pushed off from the desk and a little reluctantly fixed Sharon’s clothes. Well I fixed then as best as I could. Fixing her bra so her breasts were again covered and rebuttoning her blouse. I redid her belt but tightened it only slightly since I didn’t recall just how snug she had had it. I was also only able to work her zipper about two thirds of the way back up and decided that would just have to do. Besides what could she say; while she was asleep at the post one of the two guards that were there had come, undid her clothes and shoot their wad on her. Well it was the truth but it would be hard to prove; at least I hoped it would be.

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Caught Napping, 8.9 out of 10 based on 7 ratings

One Response to “Caught Napping”

  1. masterhank

    Well, if you’ve got to stroke it, it definitely helps to have a hot, sleeping babe to look at and touch while you pull your pud.

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