The Office Boy Ch. 01

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School leaver learns more than his new job.
2.8k words
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Part 1 of the 8 part series

Updated 11/01/2022
Created 02/10/2005
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Zorro69
Zorro69
63 Followers

My name is Glenn and I have worked in a major insurance company since leaving school almost 16 years ago. All those years ago life was quite different, I was a young and single bloke, so I took advantage of the more laid back attitudes that seemed to prevail. There has been a fairly large turnover in staff and as I have moved from section to section I can look back on several experiences with colleagues.

When I left school I joined a major insurance company with my first day seeing me arrive wearing my new suit, freshly pressed shirt and silk tie specially brought by my parents. I felt certain that I was going to take the commercial world by storm but it took a matter of minutes for me to wonder just what the hell I was doing. I realised that life in an office would be very, very different from how life had been at school.

In addition to learning my new job, the computer systems and the seemingly endless duties and tasks for which I was responsible for was daunting. As if this were not bad enough there were numerous new faces and names to learn. The vast majority of names I forgot but the common factor linking those I could remember was that they were all females who had left an impression on this eighteen year old. Although I had lost my virginity that summer, which is a story for another time, I had little sexual experience but like any eighteen year old lad I was desperate for more. The problem was most of my former school friends were now at University so the girls I had grown up with in the main had moved away. In essence I was not only starting my working life anew but my social life was inhibited too. For the first few weeks there was a growing sense of isolation and loneliness was unwelcome.

The problem that soon became clear to me was that the female colleagues attracting my attention looked upon me as little more than a boy, which of course I virtually was! I had no idea how intimidating a group of women in the office would be and for weeks I had almost no way of being able to converse with them. On the rare occasion when I was in the company of a lone fanciable woman my face would turn scarlet. It became clear they were amused and were suppressing laughter and giggles watching my discomfort. As if this were not bad enough my thoughts were leaving me with regular hard-ons and when I was at home I took care of this thinking of various lady colleagues.

On a couple of occasions I had been in the staff rest area when a group of women were chatting amongst themselves the subject matter would turn to sex, what they, their husbands and partners had done at the weekend or the night before. This would be torture, as I could not leave due to my arousal at their chat, which would be evident, and in my mind they would crucify me were they to catch sight of the tent in my trousers!

Apart from this problem things went well and after about five months I was starting to fit in and stop being the "new boy". As I got to grips with the job so it became easier to chat with all colleagues, whilst I would imagine the various girls when I wanked, I became more at ease in their presence. Following a re-shuffle of staff it was decided that we would have a team meal. We all sat round chatting at the meal, with drink and the socialising the evening went very well. Towards the end of the evening a group of the girls were going clubbing and they asked me to come along. I was ashamed of myself when my confidence didn't support me and I made an excuse saying I had an early start the following morning so would call it a night but I said maybe next time.

As I walked up the road bracing myself against the cold cutting wind it became clear that weather was worsening. Reaching the bus shelter I cursed at seeing the lack of people waiting, clearly I had taken too long leaving the restaurant, missing a bus. The rain started and in no time at all the little drizzle was replaced by heavy rain that due to the rain was being driven forcibly into the shelter, which was belying its name, providing no cover. I cursed under my breath, as the 20 minute wait would really take a shine of what had been an enjoyable evening.

I became aware of a car slowing down and heard a familiar voice. "Glenn, you got long to wait?" It was my boss, Jenny.

I replied "20 minutes, that's if it's on time."

"Jump in, I'll give you a lift home you silly sod."

I quickly jogged over splashing through the puddles to Jenny's car. Climbing I was really glad to get out of the cold and wet. I thanked Jenny for offering me a lift and then it dawned on me that I hadn't really had much too do with Jenny. Apart from being my manager there was also the age gap with Jenny in her forties placing her more in my mother's generation. I was immediately comfortable but the warmth and now being dry and also the fact that Jenny's car is a nice new Ford Focus. As we pulled away I was aware of the silence becoming a little awkward.

"This is a very nice car Jenny."

"Yes, comes with the job Glenn. Company car was part of the package when I 'swapped' sides and joined the company."

"What, they give you this car for keeping us in line?"

Jenny looked at me and raised an eyebrow. "It makes all the grief I get due to the team worth it. See before I came to the company I was with a rival firm and to be blunt my predecessor could not organise a piss up in a brewery. Well you see I had a reputation for getting situations sorted so a friend of mine introduced me to our Area Manager. My mate told me to have bad things had got and that if they wanted me I could ask my price. Anyway to cut a long story short they were limited on the pay ceiling but offered a company car as part of the deal, I said a new car every year and the deal was sealed!"

I started to see myself in Jenny's place driving a car and being the boss. My expression must have betrayed my daydream as Jenny piped up by saying "Don't get ideas Glenn I want to keep this job." I laughed and felt that any ice between us had started to crack a little.

"I am pleased with your start Glenn, I know its difficult coming into the workplace from school. You will have loads to learn and as you grow up I can see you doing well for yourself. Be patient, learn from people and one day all this will be yours" Again she grinned and as I looked at her I realised that this Jenny was different to my boss. I realised that I couldn't remember her ever smiling at work yet now we were almost connecting and to be honest this was about the first non work related chat we had ever had.

"Did you have fun tonight?" she asked.

"Yes, I think I'm getting used to the girls" I blurted out a little to quickly. Immediately I felt I had looked a fool.

Jenny grinned and looked over at me. "They think you're cute, one or two have been overheard speaking about you"

"Which ones?"

Again Jenny laughed, "Now that would be telling wouldn't it! How could I as boss let slip a confidence like that? You're young Glenn, as you get older I am sure you will learn to spot the signs".

No sooner had she said this than I realised we were pulling in to a side road. Jenny parked the car; I noticed we were in a car park of a small deserted industrial estate. The wipers stopped and I remembered how the rain was lashing down, during our chat I had almost forgotten where we were.

"Don't worry," she said "I wanted to have a quiet chat with you away from the others and where there are no distractions. Don't look so worried we are getting on alright aren't we?"

"Sure....what have I done wrong" I said displaying my naivety perfectly!

"Nothing at all. It's just..... how can I put this..........you need to stand up to the girls a bit more, you know give as good as you get. Its bad enough that they know they are making you hard but until you are a bit cheeky back it will always be like this," she smiled as I went my usual crimson shade, "and for fuck's sake stop blushing all the time" at this I nearly had a heart attack.

"But, Jen....." I started to stammer as I wouldn't have dreamt she would use what my mum, who was her age, would politely call the 'F-word'.

"Look Glenn, I will be upfront with you one to one and not as a boss. Are you a virgin?"

"NO" I replied a little to quickly and forcibly. I quickly explained my dreadfully limited experience. Then I unburdened myself as to how I was keen gain more experience but felt to unsure of myself.

"Okay, relax" she said. "You'll not win the lottery without buying a ticket, so what will we do with you?" She unclicked her seatbelt and faced me. "Guess you need a little guidance from your boss that's not in the induction material!" with that I felt her hand on my cock. Despite my shock and surprise my dick started to harden as she fondled my crotch. "Now that feels very nice Glenn. I want to say now this obviously goes no further, breathe a word of this at work and I will nail you to the wall, not just figuratively. Also, do not read anymore into this. It is a bit of fun, if you want to stop just say the word" she then winked.

"I....I..p..prom.promise" was all I could say as I felt her unzip my trousers. Within a moment she was stroking my member, which was rigid.

"Very impressive Glenn. Now you know I am married so sorry but I can't fuck you. If you are disappointed I can assure that so am I, given your young firm cock. You are quite a reasonable size. I can offer you this however" she said as she gently stroked up and down. I sucked in a deep breath as I felt another person's hand on my penis for only the third time.

"Have you ever had oral before?" she asked as I shook my head Jenny smiled, dipping her head down she enveloped my cock in her mouth.

"Mmmmm...oh. God Jenny that's so good" I said. Her warm mouth clamped around the head of my member and I gasped as I felt her tongue swirl around the very tip.

She took her hands from my shaft then ran them down into my groin. I felt her fingers snake into my open fly and she encased my balls in both hands. She gently rubbed and kneaded my balls within the confines of my boxer shorts. At the same time she slowly inched her mouth down, then up again; with each fall she I went deeper and deeper into her warm mouth. Finally I was aware that the tip of my cock had touched the back of her mouth, she pulled up licking around the head of my penis before pushing her tongue under my foreskin.

I felt across and placed my hand on her left breast, she lifted her mouth from me and laughed saying "its rude to maul your boss, without permission! Would you like to take a look?

I nodded and she slowly unbuttoned her blouse staring into my eyes my gaze was held and as she touched me again my eyes fell to see her white lace bra, which held her small boobs.

"I am sorry to say my titties are very small." She apologised and before I could explain that this made no difference to me she said, "My nipples are extremely sensitive"

I guessed that I was being given a green light to go further I released my seatbelt and leant forward. Placing my fingers under the soft silky cups I gently eased Jenny's bra up and over her breasts. I noted that her boobs were very firm, as they still stayed perky despite my removing of the silk and lacy support. Jenny's nipples were stiffening slightly as I leaned forward and gently blew cold air onto them. The nipples darkened as the small bumpy flesh of her areola drew together and visibly began to extend out from the little fleshy mounds. I placed me mouth over her stiff pink bud and licked at the hard little rubbery nipple. Jenny moaned and I became of her perfume, which was sweet and would always stay in my memory.

I also became aware that her jerking of my cock was getting harder and faster. As I placed a nipple between my teeth I gave a very gentle and playful nip to her solid rosebud. My other hand began to roughly maul Jenny's right breast. I looked up to her face and noted that her head was back, her eyes closed and she face was flushing. Jenny started to breath deeply and she was biting lightly on her lower lip. I realised that only one hand was on me and that Jenny had the other inside the waist of her skirt and I could see the outline as it moved up and down at a frantic rate.

Then she started to gasp and pant, her breasts were coated in a light film of perspiration. I licked roughly at her boob roughly flicking backwards and forwards over her nipple. Jenny's body then tensed and she squeezed my cock roughly which was followed by frantic wanking movement; she let out gasp and moan.

She looked down into my eyes and said, "I haven't cum like that for a while." She said then asked "Do you want to cum in my mouth?" to which I could only nod.

As she dropped her mouth onto me once more I looked down at her blond hair bobbing and could not believe my boss, who I had thought was prim and proper and I had never thought of during my wanking sessions, was causing me to have a mind-blowing sexual experience. My hands felt round again to Jenny's tits rubbing her lovely breasts, which brought muffled moans from her. As her moans intensified the vibrations ran round my cock causing the movements of Jenny's tongue to get swifter and swifter.

I felt my balls tighten and knew that I could do nothing to prevent my orgasm. As I came my hands clamped on each of Jenny's tits, she let out a sigh. She drew her mouth almost away from my cockhead allowing my hot semen to flood her mouth. With her mouth seemed to tighten a seal over my cock she sucked and milked me taking all of my cum, I could hear swallowing and drying down the hot salty flood.

"My god! Jen that was unbelievable!" I said as she rose to face me.

She smiled "I am glad you liked it. Just don't expect every woman you are with to give you head, if they do don't take it as read that they will be happy for you to cum in their mouths, its always polite to ask or give a warning"

She re-buttoned her blouse, which I took as a sign to make myself decent. "We best be making our way, I want to get home because you have got me so hot and wet. My husband will be pleased as I will ride his cock tonight until I cum again, of course he will never know the full story!" She laughed and kissed me on the cheek. I made to kiss her mouth but she drew back "No Glenn, this isn't love or anything. We are back to Boss and worker. I am certain you won't say a word but I warn you, God help you if you do!" She smiled "Just promise that in the future we can have a little chat, you tell me about any fun you have had"

Zorro69
Zorro69
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