Tight Trouser Trouble

Leaving university I found it difficult to get a job with the degree I had, in need of income mainly to ease my mounting debt I took a job as an office junior working for a large local construction company. The offices themselves were just a series of portacabins and were always located at the company's current site; which at this time was the building of a new supermarket. The main offices were located towards the back of the site consisting of three linked cabins, while the MDs office and the reception cabins were located towards the front. Whenever something had to be taken or received from either of these cabins it was my job, being the lowest ranking employee at the time, to go to the opposite side of the site as an errand boy.

For a large company it ran its offices with predominantly male staff, which some would say was against equal opportunities, I just thought it was unfair that there were no office girls around to ogle. The only female on site was the receptionist who doubled as our MDs secretary, a late forty year old with dark greying hair, Hillary.

As I was frequently visiting or calling her office I had gotten to know Hillary quite well and I found her to have quite a risqué sense of humour with the ability to flirt well. It must have been her twenty years' experience in construction working constantly alongside, builders, plumbers and sparkys that corrupted her mind so.

It was after I had been with the company for six months that I was given an important project to do by the director who noticed that I was wasted as a simple go getter. Although, despite him selling it as an important challenging task, I found that most of the work involved locating documents and photocopying them. To add to the "challenge" the copier in my office had packed up and so I had to use the one in reception, which meant picking my way around a building site on a daily basis back and forth carrying folders.

I was really pissed off on this particular day as I had received a visit from an ex demanding items from my flat, things turned nasty and she destroyed some of my clothes and possessions. So I was wearing an old ill-fitting unfashionable shirt and a pair of old trousers to work that day, I also had no underwear on; my ex had got at all the clean ones, what can you do when the bitch is armed with scissors. The trousers were far too tight, and were dangerously restrictive around the crotch area, if only I'd had gone to the gym more often I thought to myself through the chafing. Walking through the site I was greeted with catcalls and hollers from the workmen, poking fun at me because of the tightness of my pants and the way I was struggling to walk drawing attention to myself, I must have looked like an overweight Italian Romeo.

As I made it red faced to reception two builders came out of it both making jokes at my blatantly too tight trousers, I was cursing furiously at my ex inside my head and vowing to go shopping after work to buy some new clothes. When I walked into the office Hillary had her back to me and was bent at the waist reading something, I had not really seen her from behind her desk in all this time and noted that she had a nice ass for her age. In fact she had quite a nice figure for her age, not slim but rounded, her ass looked firm and her waist the right proportions for her size. As she turned I then passed a glance over her breasts something I had done often. I reckoned they had to be a 32DD and I must have stared directly at them because a slight forced cough brought me back from my reverie. I jumped out of my breast trance, smiled lightly at Hillary, saying hello and put my things on a desk that had been allocated to me for my task.

As I started to sort through the folders Hillary came over to and started removing some folders and documents of her own that were on the desk, apologising for the mess saying that the builders had had them. As she lent over to pick them up my eyes focussed on her cleavage which came into view beneath her smart unbuttoned blouse, I was mesmerised and then I felt danger brewing in my tightly packed loins. I had not had sex for at least two weeks and my balls were practically bursting for release, I had been coming home from work recently and crashing straight out, thus not relieving myself manually so I was a time bomb. Plus the tight trousers and friction from the walking had been gently massaging me all morning, this added visual stimuli was now sending me into critical.

My cock started to harden, and with no room to grow it was painful in these pants, realising what was going to be on show and I grabbed some documents and darted to the copier. Hillary oblivious to my predicament finished her tidying and went and sat back at her desk idly chatting to me while I was concentrating on un-sexy thoughts. After a while she must have noticed my discomfort because she asked if I was all right, I told her about the night before and that I was wearing trousers two sizes too small and she asked me to step back so she could see with a grin. Hesitating I did, but turning so that my ass pointed in her direction, my buttocks outlined perfectly by the skin-tight trousers. Hillary being true to form wolf whistled and jokingly said "easy tiger" chuckling. I laughed; relieved that I had managed not to clothes flash the boss's secretary my bulge. I waited until Hillary was engrossed in a task and I resumed my photocopying, finishing the batch I had I went to grab some new documents but as I did so I banged my constricted bulge onto the side of the copier, I let out a yelp doubling over slightly.

Hillary quickly stood up asked if everything was Ok, I managed to mumble an answer still half doubled up and holding my crotch, I painfully smiled and stood up slowly. She looked at where I was holding and with a knowing look, mouthed an "oh dear" and laughed a little before sitting back down and carrying on with her task. Now the photocopier was positioned directly to the opposite side of Hillary's desk and as she sat she crossed her legs and the slit in the side of her skirt parted to reveal her stocking tops. This proved too much sensory overload to my mini dumb brain and my cock lurched again straining painfully inside its tight confines, I felt some pre-cum ooze from its tip and start to stick onto my leg and I was in panic stations in case it showed. I had to wipe it and give it some room I thought to myself, but if I try to leave I will have to walk past her to get out the office, plus the toilets were outside in portables and I could bump into workmen. Quick thinking I turned, positioning myself with my back towards Hillary, looking at her stocking clad thigh was the cause of this situation so stopping the view might help. Once my back was turned I undid the top button of my trousers, they were so tight that there was no way they could fall down, pausing to cast a glance back at the receptionist who was thankfully oblivious to my actions, I then slowly undid my zip a little.

The head of my cock protruded a little, the pressure off it I checked for a stain on my trouser front and was glad it had not seeped through, I reached in and wiped up the pre-cum with the bottom of my shirt, it would be tucked in anyway. Relieved that the most dangerous part was over I pushed my cock back down and tried to fasten my trousers back up. To my horror my cock was unmoving rigid, now free to be fully erect and rock hard it was making it impossible for me to get the top button fastened let alone do up my zip.

The office phone rang causing me to startle, and after a few moments to my dread I heard Hillary say the words "how many copies" and then add "right away Sir", the MD must have asked her to photocopy something. She hung up and started to jot something down on a post it and I started to panic, my heart racing I made another failed attempt to cram my cock down and redo my top button but my cock was not going to get back in without a fight and I was causing myself pain forcing it. Noticing movement I looked back and tried not to act suspicious as Hillary stood up and moved to a cabinet close by to take out some files cursing myself for giving her ass a once over as she did, which was not helping the situation. She glanced over her shoulder and asked if it was OK if she could use the copier for a moment, I told her it was fine but could wait just a few seconds and I started to recopy work I had already done, willing my cock to go down. Hillary was now stood less than three feet away, one hand on her hip, tapping her stocking clad leg with a file, waiting, I was trapped.

Panic stricken hoping she would not notice I tried to cram my cock down my trouser leg but it would simply not go in, Hillary noticed me fumbling around and to my building horror she came close behind me, I panicked and turned myself into the copier mashing my cock against its front just as she was next to me. With a curious look she asked what I was doing, so much for not looking suspicious, I could feel myself going red and I babbled that I was having problems with the copier. In one fluid moment it felt like everything came crashing down, Hillary made a tutting sound and said why didn't you say and she pulled me away from the machine. My eyes wide and face terrified as my cock now completely free from the pressure of being crushed against the copier sprang up and down pointing directly at Hillary. I wanted the ground to open up and swallow me; I frantically tried to rectify the problem stammering nonsense when a hand on my cock stopped me completely.

"Is this giving you trouble?" Hillary said placing the file onto the table and kneeling down in front of me, her head inches from my dick. I was dumbstruck, I could not say anything, and I wasn't given a chance as her bright rep lipped mouth enclosed around my cock sucking my length into its depths. I had to grab the side of the side of the copier as my knees went week at the unexpected action I was receiving and I watched as her head bobbed back and forth, she was sucking like a woman possessed and I could feel an impending orgasm. I clasped the back of her head as my legs began to buckle and I started to groan shooting burst after burst of my seed down her throat, Hillary expertly swallowed it all and then resumed sucking on my semi erect cock not surprisingly breathing new life into it.

Hillary stopped sucking and stood up pressing her chest into mine stating, "It's been a long time since I have had a young studs dick" I could feel her nipples erect under her flimsy blouse and I could smell my cum on her breath, I hurriedly groped one of her breasts and she started to wank me slowly staring hungrily at my cock. After a few minutes in this position she was breathing heavily and let out a little moan as I assaulted her large breasts, sitting back onto my desk and looking right at me she slowly opened her legs, displaying her black stocking tops outlining her milky white thighs and to my utter surprise a panty less bald cunt, glistening and puffy and clearly ready for a good pounding.

Hillary still holding my now fully revived cock pulled me between her legs directing me straight into her, it slipped right up her with ease and I felt amazing pleasure as her wet warmth surrounded me. I did not move for a moment enjoying the sensation of her warmth before I began slowly building up a motion, eventually building up to a full speed ram wildly slamming into her. I pulled open her blouse and released her massive breasts over the top of her flimsy bra pawing and sucking on them as her stocking clad legs wrapped around my waist. The table rocked and shifted position at the force of our furious fucking, Hilary through her moans told me to hurry, the MD was expecting his copies soon, I thrust faster and harder and despite having had an amazing blowjob I quickly felt another eruption building and after a minute or so of frantic pounding I felt my head engorge, Hillary must have felt it also looking at me and gasped "Inside, it's OK, inside me" this sent me over the edge and I shot my second load deep into her, causing her to have a simultaneous orgasm.

I lay on top of her exhausted, panting with sweat dripping from my brow; Hillary adjusted herself and pulled my deflating problem causer from inside her. I stood up and in a haze finally managed to pull my tight pants on. Hillary grinned at me and handed me the file asking me to quickly photocopy the contents, she had to go freshen up in the toilets before taking it in to the MD. When she came back I handed her the copies I had done for her, I asked her what it was and she told me it was the paperwork for my transfer into reception and that I was to become PA to the MD and her trainee. I was to learn a lot more than shorthand over the next two years.