Chapter 1
As these things are measured, I have been quite a successful person in life, and I am often asked about the secret of my success. I would have to say that it’s my confidence with telling people the truth, being honest when you know that telling might hurt them but being considerate when you do which lies at the root of why I have found good fortune in the things that have interested me. I wasn’t always this confident though, and looking back, I can trace that turning point back to a 2-week period in my youth. But to illustrate my story better, I should start with a brief history of my life to that date.
I was born in 1928, in Windsor, just outside London and my parents could not be more different as people. My father was a labourer who had come back from the great war of 1914-1918 a broken man, according to my mother, and which made him a bit of a drinker. He was a few years older than my mother, she had known him as a young girl, before going onto marry him when he got back from service.
Now I am older I think it’s a miracle I was conceived at all as my memories from him an early age revolve around my mother alone with my father only occasionally appearing. When he did deem to make an appearance, he reeked of booze and was not really a nice guy to be around.
From my recollection he never beat my mother but she did do her best to shield me from him, particularly when he was in a sour mood, which was most of the time.
My mother could not be more different. She was a warm, very loving person and I felt her presence constantly. She was a homemaker but could turn her hand to most things and I think this was where I get my creative side from.
Our lives were to change in the winter of 1934. It was a particularly cold winter and things were pretty tight financially with work hard to come by. That didn’t stop my father from drinking though and it was a constant source of tension and arguments in the house.
One particular night, I heard my parents in a particularly vicious fight after I had been sent to bed.
“Stan, for god’s sake, did you take the housekeeping money out of the jar? I can’t believe you’ve left us nothing! Can’t you just stop?” I heard my mother shout at my father in the living room.
My father was drunk and therefore incoherent in his reply but I did understand the smash of something breaking against the wall after his response.
“I cant talk to you when you are like this, I am going to bed and you better sleep down here, I’m not sleeping with you when you’re like this but I will tell you this Sonny Jim, you had better have an idea of how we are going to replace this money by the morning because I am at the end of my tether!”
I heard a door slam and my mother coming upstairs. I pretended to be asleep, as I knew she would check on me before she retired to her room herself and once she had done that, she entered her own room and shut the door.
The following morning, I was awake early and went downstairs to get ready for school. I knew it was likely that I would be hungry until teatime and that we probably would have no food in the house, so I was thinking of how I might try and steal an apple off the greengrocers stall on the way to school to tide me over when I tripped over my father.
He was lying on the floor with an empty whisky bottle in his hand and at first I thought he had just passed out but then the smell hit me and as my eyes accustomed to the light in the room, I could see his face was in a pile of vomit. He was blue and cold to my touch, his glassy eyes telling me that this was no ordinary drunken stupor.
“Dad?” I said as I tried to shake him awake.
I knew I had to fetch my mother immediately and bounded upstairs to get her, “Mum, Mum! Come quick, something’s wrong with Dad!” I shouted
Her door opened and she appeared in her dressing gown, hurrying straight passed me and down the stairs.
“Stan? Stan!” she cried as she saw my father’s body but even then, she must have known it was too late.
My mother rushed me next door to our neighbours, Elizabeth and John Miller, who had moved in about 2 years previous. They were about 5 or 6 years younger than my parents but my mother, and Liz as she liked to be known, had struck up a strong friendship straight away and were always in each other’s kitchens.
I was bundled into the living room as my hysterical mother explained through sobs and hushed tones to Liz and John what had happened. John went with my mother and left me with Liz for the rest of the day. As a boy, you don’t really know what’s happening in the adult world around you, but I guess now that John helped my mother get a doctor and alert the authorities to my fathers demise.
The next few months were a bit of a blur if I am honest.
As my father hadn’t been a constant part of my life, I didn’t really feel any different other than knowing he wasn’t coming back. They say kids are more resilient than you think to this sort of thing and I guess that is the case as I went back into my routines pretty quickly. My mother on the other hand, was left in a right state.
Obviously, she would have to find a job to help support us and had luckily found a position as a housekeeper in a well to do household about 30 minutes by bus from our house. This position however did come with its downsides as she would work long hours, which meant she couldn’t spend the time she used to with me.
She was constantly worried about me though so asked Liz if she would keep an eye on me after school until she got home and so I ended up spending quite a bit of time at the Millers.
During this period in my life, I naturally ended up getting quite close to John and I would often end up in his shed workshop with him showing me how to use certain tools and how to work with my hands on metal and wood, which is something I continued to love to do all through my life.
So, things started to settle down into a new routine and life seemed pretty good.
That was until Hitler decided to invade Poland.
Immediately in the aftermath of Britain declaring war in 1939, conscription started and as he was under 41 years of age, John was drafted into the forces. I sensed the shift in my environment immediately as Liz become much more quiet and often she would have this faraway look in her eyes, staring into space.
She was distraught when he left for basic training and then deployment. Naturally, I then became the centre of two women’s worlds as they needed to focus on something other than the nightmare of the world around them.
Again, for the next few years, things settled into a new pattern and the three of us spent a lot of time together in the evenings, keeping abreast of places where John was deployed, anxiously waiting for any titbit of news on the radio about where the conflict was at its heaviest.
One day in 1943, I came home from school to find my mother waiting at the gate for me.
“Hello Mum, why are you not in work?” I asked, “We had better go inside love.” she said
It was in that moment that I knew the worst had happened and that John wouldn’t be coming back.
It turned out that the ship he had been stationed on had been sunk by a German U boat and he had perished along with 148 of his comrades.
I felt desperately sorry for Liz, but also for myself as John had been the only real male presence in my life who had given me any kind of attention and direction. Once again, life for us was in turmoil.
Liz leaned on Mum quite a bit over the following couple of years and until once again, she learned to smile and laugh a bit like she used to. By that point in my life, I had just turned 18 at the time, girls and women seemed to suddenly be everywhere and impossible to ignore.
I had shot up quite a bit between my formative teenage years and now stood a good 6’2 and had filled out as well from my skinny youth. If you saw a picture now of me as I was then you would also say I was a good looking lad but at that time, I was painfully shy, a bit of a loner due to my quiet nature and oblivious of my impact on women.
Perhaps it was the lack of male influence or the fact that there was an over positive female presence around me but although I had grown normally I just didn’t know what to do to get to the next stage of even just talking to a woman.
Due to my natural abilities honed during those times working in the shed with John, I had found a part time position in the well to do household my mother worked in as a handyman. I was also undergoing an engineering course and apprenticeship, which I would eventually use as the basis to form an extremely successful business. At the time though, I had just hopes to pursue that as a career but my course did not start until that September, so I had to spend the summer working, as much that I didn’t have a social life than the need for extra money. Benefits of working all of the time though, was that it helped with my physical development and you could probably tell from my physique that I was a fit boy.
Not that this helped with the ladies though. Even in my work environment, if a female member of the household would speak to me, I would blush, turned red and mumble through a conversation. As such, I tended to avoid such engagements and therefore ended up with a bit of a reputation as a sullen character, which I did not make any effort of to dispel.
My ‘type’ as they say tended to veer towards the voluptuous, and women that were older than me held a particular fascination. I felt their ‘experience’ would be what I needed to help my progress from boy to man. Therefore, older, confident women with big tits and slimmer waists would hold my fantasies for some years but having no opportunity to venture outside of my social circles to meet new people, Liz, a few of the women at work and dare I say it, my own mother, were the subjects of my nightly masturbation sessions.
Soon after my birthday, I ventured home earlier than normal due to unexpectedly finishing my duties earlier than I thought I would. This wasn’t a normal occurrence, but it was the holiday season and the household were away, so were all of the small staff they employed, including my mother, who was at home.
Anyway, as I would be doing nothing, I was keen to earn some extra money and I had taken on a list of jobs to undertake whilst no one was around, so had used the opportunity to get them done. Without any distraction or worry that I would be faced with another person being there, I quickly completed what I needed to do and then managed to catch the early bus back home.
As I entered the house, I could hear Liz and my mother talking in the kitchen. I was about to enter when I heard my name mentioned and froze, curiosity getting the better of me, waiting to hear what they were talking about.
“Liz, I just don’t know what to do,” said my mother, concern in her voice “its just not normal is it?”
“Well I don’t know Margaret, as you know John and I couldn’t have kids but it must be, Trevor is such a normal boy.”
“It’s every day Liz! His sheets need changing every day and the amount of stains on them you couldn’t imagine!”
“Doesn’t he have a girlfriend or anything Margaret? He must have, he is very handsome.”
“I don’t think so, he is very quiet all of the time, doesn’t go out and hardly speaks to anyone in work, especially women.” said my mother
“Do you think he, you know, likes men?” said Liz
“No, I don’t think that’s it as I do catch him sometimes staring at various women in the village and at work. I think he is just different. I am so worried he will end up like Stan was.”
There was a silence and then, “Well, would you like me to talk to him? I don’t mind answering his questions and if he is curious, I can show him a thing or two. It’s an age since I’ve had one up me!”
At this point, I was frozen to the spot, heart racing and instantly pictured Liz and her big tits, my cock in her hand, showing me how to make love to her. I was instantly hard and it was actually quite painful.
After what seemed like and age, my mother said, “What are you saying! He is just a boy Liz and at your age, that’s disgusting!”
“Well, better to have him find out on me than him force himself on some poor girl or get her pregnant.” commented Liz matter-of-factly.
Unfortunately, I wasn’t able to hear the rest of the conversation as I realised almost too late that as Liz was saying this, her voice was louder, and she was obviously moving towards the door. Before she opened it, I escaped upstairs to my room whereby I instantly pulled my cock out and wanked off three times on the trot to thoughts of Liz.
That night at tea, it was just mother and myself, I didn’t ask where Liz was, as I guessed that she was probably avoiding us.
“You alright?” my mother asked
“Fine.” I responded and felt my mothers gaze linger on me as that one word disappeared in silence.
Not another word was said between us as I was petrified I would give my eavesdropping away, and as soon as we had finished the dishes, I made my excuses and left for my room.
Nothing was said the day after but it was a full week before Liz showed her face again, but I was relieved that relations between Liz and my mother seemed to have returned to normal.
About 2 months later, my mother informed me that she was needing to go into hospital for an operation.
“There is no need to worry,” she said, noting the concern on my face “it’s only tonsillitis and that’s a fairly routine thing but they do have to come out so I will be in hospital for about a week or so.”
“I have asked Liz to prepare a meal for you in the evenings but your 18 now so can stay here on your own.” she said
“Alright Mum, I am just a bit worried that’s all and I will come and visit every evening.”
“You’re a good boy Trevor,” she said “never forget that.”
Two weeks later my mother went in for her operation, which was a complete success. The doctor told me that she would need about a week in hospital for them to monitor her for infection and then spend some time at home afterwards convalescing.
The day of the operation, and after making sure my mother was alright, I went back to the house, pretty relieved so my mind wandered to that evening and the meal with Liz.
I hadn’t forgotten the conversation some months earlier and she had been the sole focus of my carnal thoughts ever since. I had tried to keep my behaviour around her the same as it always had been before that day but now everything about her seemed to have an effect on me and I was constantly daydreaming about fucking her.
A few of those times my mother or Liz had to almost shake me out of these situations and my mother was constantly shaking her head and commenting about how rude I was getting.
That night, after I had had a bath, I got dressed, went next door and knocked on Liz’s door and entered as I usually did.
“Its only me Liz!” I shouted as a I entered the door
“In the kitchen!” she said as I made my way through the house to the kitchen.
“Hello Liz,” I said as I ventured through the kitchen door “How are you?”
“I am fine dear” she said “how is your mother? I’ve been worried sick all day.”
“Oh, she is very well thanks, Doctor Cooper said everything went really well and she had woken up and was good before I left, a bit sore but otherwise, fine. I will go back tomorrow.”
“Wonderful!” said Liz “I am so relieved.”
It was only now after this little conversation I started to take in the view that Liz was affording me. She was wearing a nice dress, which made full use of her cleavage and the skirt of which showed off her shapely legs. I must say, I was very hungry and not for the shepherds pie she had prepared for us for our meal.
We made small talk through dinner and when we got to the end of the meal the conversation lapsed into the usual silence that I found myself in when faced with talking to a member of the opposite sex.
“Is anything wrong Trevor?” she asked as I sat there with my usual neutral expression on my face “You don’t seem yourself.”
I didn’t know what to say. I knew what I wanted to discuss but I dare not breach the subject as she would know that I had overheard her conversation.
“You can talk to me you know.” she said. I met this comment by just staring at my now empty plate “Please say something.”
“Can’t.” I croaked, turning bright red
“Are you in trouble? Is it work? Have you got girl problems?” she asked which I followed with just a shrug.
“I’ve noticed that you seem different over the past couple of months, you’ve become even more quiet than you used to be, avoiding talking to me even, so I know something is wrong.” and she lifted my sunken chin up with her hand, so our eyes met
“It’s nothing,” I said “I…..well, I…..sort of….overheard your conversation with Mum a few months back.”
“Ahhh, oh my…” she said, the silence was now deafening
“It’s fine,” I said, “I know that you didn’t mean it or anything, but I just can’t get it off my mind.”
She didn’t say anything but instead got up and went to the sink, her back to me.
“I’m sorry,” I mumbled “I didn’t mean to overhear and shouldn’t have said anything.”
A heartbeat or two went by and then she turned and looked at me with a small smile on her face “I suspected you knew what me and your mum discussed. I thought back to your change in behaviour and put two and two together, that was the only thing it really could have been although I couldn’t ask for obvious reasons.”
My breathing had become a bit ragged and didn’t know what to say, so said nothing.
“How do you feel about what was said?” she asked, and I just shrugged.
“You have to do better than that Trevor, how do you feel?” she was now more insistent.
“Excited.” I mumbled.
“Have you had fantasies about me?” to which I nodded.
“Hhmmm, nice to know that I still have some effect on men.”
“Are you kidding, you are the sexiest woman I know!” I blurted out, summoning courage I didn’t know existed.
She laughed and said, “I’m not surprised that at your age you would think that Trevor but believe me, you will learn in time that your perceptions of sexy will change as you get older.”
“I really mean it!” I protested
She walked over to me and held my face in her hands “I know you do love.” she said
“Are you going to do what you said you would to Mum?” the yearning in me at fever pitch, “I’ll do anything!”
She let go and the smile disappeared a little “I don’t think so Trevor,” she said “After that conversation, me and your mum didn’t speak for a bit and it was only after promising her that I was joking and that I would never do such a thing that we started speaking again. I don’t want to lose your mum from my life Trevor, she has done so much for me and I can’t see her upset”
I was devastated and it showed. I got up and said, “I’ve got to go now, I hope you don’t mind me not helping with the dishes.” and turned and walked out.
The following day, I visited Mum and told her that everything back at the house was fine and that Liz had cooked me a meal as promised.
I got back to the house and there was a note on the mat as I entered. I opened it and it read “Please come over for tea tonight, I would hate for us to leave things as they are.” I thought about it and tried to deal with the maelstrom of emotions within me.
Anger, embarrassment, shame at my childish reaction to our conversation and my usual thoughts of inadequacy welled up inside and it took everything for me to decide that I should go over to Liz’s house. I concluded I should, as it wouldn’t be long before Mum was home and I needed things back to normal before she suspected anything had gone on.
I composed myself outside of her front door, knocked and entered as usual and was met with the usual “I’m in the kitchen!” response. I walked into the kitchen and my eyes nearly popped out of my head.
Liz was standing there, in heels, stockings, a short skirt and tight top, which had been unbuttoned to the point where her tits were almost spilling out. She has also done her hair and make up and looked amazing.
She looked me up and down and my impression of her look was obvious as my hard on was raging. “I can see you approve.” she smirked as she raised an eyebrow and a nod towards my crutch. “Please sit down Trevor”
I sat down at the table and she took a seat beside me “I guess you are wondering why I am dressed up like this?”
Shocked, I didn’t say anything and let her go on “Well, after we spoke last night I didn’t really sleep. I was turning over in my mind what was said and how I felt about that and I finally decided this morning that I felt that I had been very unfair and had probably made your situation worse than it should have been.”
She took my hand tenderly “I was your age once and know what its like to have all of these feelings suddenly land on you and I also thought back to how the presence of these,” she hefted both of her gorgeous breasts in her hands “probably hasn’t helped.”
I gulped and looked downwards but she shifted my gaze up again so we were again looking at each other.
“So, what I decided was that if everyone wants you to act like an adult, then we should treat you like one. You are over 18 now and should be able to make your own decisions and talk to other adults in an equal basis.” and she stood up and walked to the kitchen door.
“Now, let’s go into the living room and we can discuss this properly.” she said
I stumbled through the door following her shapely ass as it walked sexily through to the living room, the intoxicating smell of perfume trailing behind her leading the way.
“Please sit.” she said, showing me a space on the couch where she expected me to sit down and she shut the curtains, then she sat beside me, on the edge of the couch.
She placed a hand on my thigh and then said, “I will speak first and when I am done, I want you to respond. Now, I don’t expect you to be all confident and suave but just speak honestly, that is very important.”
Her hand was moving up and down my thigh and I shifted uncomfortably in my seat, trying to adjust my cock so that I could get more comfortable.
“Are you uncomfortable?” she said, and I nodded my head. “Let me help you with that then.” and the hand that had been rubbing my leg gently moved its way up it and popped the top two buttons of my trousers “There, is that better?” and I nodded again.
“Now, I need to be firm here Trevor, and I cannot stress this enough. Anything, and I mean, anything that happens between you and I stays in this house. You must remain your usual self when we are around your mother as she would string me up if she found out I had broken my word and you must tell no one else about this, people would not understand, even though you are of legal age and we are both unattached.”
She touched my thigh again as I opened my mouth to say something “I haven’t finished yet Trevor.” and sensibly, I closed it as quickly as I had opened it to allow her to continue.
“I am willing to answer your questions and also take you through your first steps into how to please a woman, but I will not accept you being rude or abusive to me. I am also not a toy to be played with or have demands made of. I will set the pace and you will do what I say and when I say. In addition to this, our arrangement is only going to go on until Margaret is home as it’s too much of a risk for her to find out otherwise. Now, do you agree to those rules and how do you feel about it?”
“I can’t tell you how much I agree Liz!” I exclaimed “When can we start?” I was like a kid on Christmas morning knowing that the best present he had ever received was sitting in front of him, waiting to be unwrapped.
“Calm down love,” she said “we’ve got probably at least a week and we will be building things up slowly, so you can think again if you think I am sleeping with you tonight. But, I am happy to answer any questions you might have. Now, what would you like to know?”
I considered this for a second “Well, how do girls get well, you know, excited?” I said
“Good question,” she replied, “each woman is different and has different tastes but there are a few things which every woman tends to find gets her wet.”
“Wet?” I asked
“Well, we will get to that later on, but a woman needs to feel appreciated and sexy to get to that point, so you need to appreciate her, show her attention, that you’ve been thinking about her, warm her up in order to get the most out of the experience. For instance, come here.”
I moved closer to her on the couch and she moved her face in towards mine. I felt her lips brush mine and our kiss grew. As I had never even kissed a girl before, I let Liz control it and just followed her lead, just happy to be kissing this gorgeous woman. I wasn’t prepared for what Liz did next.
She took my hand and moved it up to her breast and I got my first feel of a woman’s body. I gently squeezed and Liz elicited a moan into my mouth.
This went on for a couple of minutes and then Liz pulled back a bit “How are you feeling?” she said. “Fantastic!” I replied through a grin.
“So, back to the questions.” she said
“May I put my hand inside?” I asked, looking at her top.
“Well, as I said, you need to build up to that, why don’t you see how you go and if you haven’t got to that point, I will let you know.”
Emboldened, I leaned in again and started to kiss her, again gently squeezing her breast over her top. I could feel her nipple poking through her underwear and when she started to moan again, I took that as my cue.
I started to slowly slip my hand between the soft flesh and material holding this amazing orb in place.
“Hhhmmmm,” she purred “you are a quick learner, aren’t you? Kiss my neck, its another place that really turns me on.”
I moved my lips towards her neck and she arched her face upwards, giving me room and space to plant small soft kisses along it. At the same time, my hand now fully inserted itself within her top and bra, I now felt her hard nipple under my hand for the first time.
Liz’s own hand then started a journey I didn’t expect as it moved up my thigh towards my lap.
Even though I know now we were only engaged in heavy petting, at the time this was the most erotic experience of my life and my cock was poking through the top of my trousers where she had released some of the tension earlier.
Suddenly, I could feel her fingertips graze the skin on my cock and her light, feminine touch felt wonderful.
“Stand up Trevor.” and I immediately obeyed her.
Standing, my crotch was at the height of her head and she started to undo the remain buttons and pulled my trousers down. I saw her open her mouth a little as my cock sprang forth in front of her, resplendent in its newfound freedom.
“My, my,” she cooed “you are a big boy, now sit.”
I returned to the position I had been in and immediately went back to massaging her neck with my mouth and tit with my hand. She went straight for my cock taking it in a firm grip. Her hand felt wonderful as it enveloped my now raging penis at the base and she started to move her hand up and down. I moaned myself as I felt the delights of Liz’s hand as she worked her magic, building up a tempo until a familiar feeling started to form in my groin.
“Nnnnnnnggggghhhhhhhh!” I cried as I suddenly came, large ropes of my semen arching through the air and landing on my legs, Liz’s skirt and top, the couch and floor.
“You must have needed that.’ she said as she looked at me in the eyes which were only coming back into focus now following the intensity of my orgasm. “Let’s get you tidied up.”
With that she stood, fetched a cloth and then wiped the come off me. “You can pull your trousers up now.” she said when she had finished. I could see a glob of cum on her finger though and she saw this at the same time. Looking me dead in the eyes she inserted the finger into her mouth and sucked it clean “Hhhhmmmm, yummy.” she sighed.
“Now, Trevor,” she said in response to my open mouth “not every woman likes the taste of a mans cum. Some, like me, love it, which is lucky for you by the way. Some dislike the thought and taste and will refuse to even think about such a thing. What I am saying is that you cannot treat all women the same. Each woman is a different adventure, with their own likes and dislikes, and its up to you to find out what those are so that she in turn will give you everything.”
She paused for a second and then continued “I think our lessons are concluded for the evening. How do you feel?”
“Amazing!” I replied, still coming to terms with the evening’s events.
“Wonderful, me too,” she said “tomorrow, you can ask me different questions and we can explore new things together, but I want you to think about what you learned here tonight as its important that these first steps are not forgotten.”
With that she went back into the kitchen “Don’t forget to take some of the stew that’s on the stove with you,” she said. “You will need to keep your strength up! I am going to get changed, I’ll expect you will be gone by the time I get downstairs so I will see you tomorrow.” and with that, she was gone.