How the Hell Did I get Here?

I paused at the doorway as I glanced in and saw Helen spread out on the sofa, her body splattered with copious amounts of my cum. Eyes shut and looking somewhat flushed her right hand brushed her forehead. Her other arm was extended out over the side of the sofa with her cigarette dangling from her hand. A gentle plume of cigarette smoke hovered above her.

How the hell did I get here I thought to myself?

My morning had started innocently enough. With a full week's leave to take advantage of, day one had started with a few bits of business to care of. With a couple of those being in his area I thought I'd make an all too rare visit to my friend Dave's, son of Helen and Roy, long-term friends of my folks.

I must confess I had been seriously remiss in keeping in contact with my friend in recent years. A victim of a car crash some fifteen years previous Helen and Roy were devoted in attending to him in his debilitated state, running themselves into the ground and spending every penny they had to ensure he had the necessary care.

Helen and Roy had become friendly with my parents shortly before both Dave and I were born within a couple of months of one and another and had regularly been around our house as I grew up. Likewise we often visited their home and for around the first fifteen plus years of our lives Dave and I were constantly in each other's pockets.

As we grew older our paths took different different directions and whilst always retaining our friendship, we gained new, closer, friends from school and our own areas of interest and our paths crossed less and less.

Ironically though as the ties with Dave loosened and I saw less and less of him, my feelings for Helen his mother, became stronger and stronger.

When I hit that stage in my early teens as most boys do when suddenly a lustful attraction of girls and women arrives from nowhere, Helen, still a regular visitor to our house, was right at the forefront of my newly developing infatuation with females.

Looking back it must have all looked a bit pathetic, me a skinny little spotty teen, trying my utmost to impress this sexy thirty-something. Using any excuse to try to get into situations where I might end up in her company a bit more, trying to impress her with the latest jokes from school, trying to get dances with her at parties. Yet she humoured me all the way, never dented my confidence or made me feel small when she could have easily told me to sling my hook on any number of occasions.

Perhaps it was because she was one of the first women I ever wanked off to, she would always be special. Just fantasising about her would be enough to bring myself off. Even better if there were any photographs of her that happened to be taken at the most recent party or get-together - I would imagine it was me dancing with her, or sitting with her and fantasising about what we'd done together after the photo was taken.

Indeed on one such occasion when Helen and Roy were visiting my parents I was literally seconds away from being caught by my father, who was looking to re-unite Helen with her coat, wanking myself off whilst tightly pressing Helen's leather jacket to my body, imaging that she was of course inside the soft black leather coat and lying on top of me.

Much water had passed under the bridge since those teenage years and of course Helen had aged too. That said, now well into her fifties and despite the stresses and strains that had been placed upon her looking after Dave, a few wrinkles aside, Helen had retained the slender appearance and striking good looks that had attracted me all those years ago in my youth.

I rang the front doorbell and a few moments later was greeted with a surprised looking Helen. "Ohh!!!!!!!! Hiya honey. What a surprise to see you!!". She embraced me and gave me a peck on my cheek and ushered me inside.

Being called honey brought back a rush of warm feelings and reminded me of another aspect of my teenage crush on her. Helen had always used affectionate terms when addressing me things like honey, babe, flower and sweetheart those kind of things. It wasn't really a style of language that anyone else I knew really used so it felt really personal and turned me on to loads to be called babe or sweetheart by her knowing all the whole when in my teenage fantasies I really really wished I truly was her babe.

"Just thought I'd pay Dave a wee visit" I said as we made our way into the kitchen. "Ohh, no. You've not long missed him. He's away with Terry his carer for the day".

"But not to worry, you'll stay for a cuppa won't you.....?".

"Of course" I replied, much to her visible delight.

Helen stuck the kettle on and opened the back door, lighting up a cigarette, as she made her way out to the patio. We exchanged small talk about my parents, Roy and Dave before she returned and finished making the tea.

Moving through to the living room she sat down beside me on the sofa and we chatted some more. After chewing the fat for a good wee while and having our tea, Helen moved to get up to take the empty cups through to the kitchen. She gasped sharply and winced in some discomfort. "This bloody neck and back of mine. I think its just a tension knot, but I just can't seem to shake them off at the moment".

I recollected the initiative we had at work sometime back where someone came in once a month and did fully clothed massages for you. I suggested to Helen she should maybe try something similar. I remembered how much it had benefited me and began to rabbit on about how good it was and that it wasn't that expensive etc. etc.

Suddenly it hit me whilst in full flow that with the amount of money that Helen and Roy needed to spend on Dave's care that there would be little in the way of expendable income for what I'm sure Roy would have viewed as trivialities such as fully clothed massages.

Without even considering the more erotic side of offering to massage the woman of my teenage dreams, my thoughts were more of redeeming the awkward situation I felt I had got myself into and how I could try to help. I tailed off my talk about my massage experiences at work and suggested : "You know though there's probably still nothing to beat having your shoulders done and relaxing in the comfort of your own home....If it would help, I'd give your neck a wee rub.....?"

It was the sentence that would spark off an eventful and lust filled few months.

Any hint of awkwardness that might have been there on my part, as it dawned on me what I had just offered, was immediately blown away by the enthusiasm of her response. "Would you do that for me....? Really....? That would be fantastic".

Helen wasted no time in sliding down off the sofa to the floor and nestled herself between my now outstretched legs. "Roy sometimes gives my neck a rub, but to be honest he's not that great at it. Am I OK here for you honey?" she asked.

Honey. I shuddered a little as the first erotic thoughts of what might transpire began to cross my mind.

"You just lie back and enjoy and I'll try to get rid of the tension in your neck. Just tell me if I'm too hard or rough."

"OK sweetheart"

Our chat recommenced as I got to work. Lying against the couch her neck and above her shoulder blades were in reach and I worked those areas intensely to begin with. Soon the chat would be punctuated by the occasional an occasional sharp intake of breath and an "ohh" or "ahh" as I hit a particularly tender spot.

"Harder there", "Up a bit", "Down a bit" began to follow as I was directed to the points she wanted attended to most. I must have learned something from those massages at work as my hands were clearly having the desired effect on Helen.

I began to expand the area I was working on. I rolled her head back and forth a few times and then ran my fingers tenderly through her her and down her cheeks. Her tone had notably changed when she almost whimpered at me "Oh honey, that is nice. I do love my hair being played with".

We both seemed to have moved on to another level from innocently getting rid of a tension knot in her neck. For the next few minutes I alternated between her neck, the top of her back and her head, each time drawing a little shudder when I caressed her hair and face softly.

We weren't saying much now. I glanced down and Helen's eyes were closed and as I peered over her I could visibly see her nipples erect and protruding out her t-shirt.

I suggested that she might want me to do her lower back: "Oh that would be good" was the immediate response and Helen took up position flat out on the carpet in front of the fireplace.

"In fact......" she said as she sprang back up "It would probably be easier for you if I took this t-shirt off wouldn't it....and you could probably just unsnap my bra too when I'm lying down. That would help wouldn't it. I'm really enjoying this sweetheart".

"Sure" was as much as I could offer in response as I momentarily got an eyeful of her bra as she pulled her t-shirt over her head, then her titties as she took it upon herself to remove the bra of her own accord.

I resumed the massage and worked on her spine and the bottom of her back. Occasionally I'd go for her sides and attempt to sneak a touch or brush of her boobs which were squashed beneath her. She'd let out a little giggle as I stroked the general area, suggesting "that's tickly". More and more relaxed she was becoming all the while.

By this stage I don't think either of the two of us had thoughts which remained entirely innocent and we seemed to be at a point where we were testing how far we would take he the pretence of the massage being purely therapeutic.

I next suggested that perhaps she might want to let me loose on her legs and her bum, that they too could have a lot of tension in them. Once again the staple response: "Oh that would be nice babe" and she raised up and shuffled pulling her joggers down and kicking them off giving me my first uninterrupted view of her tight tits.

Helen raised the stakes higher immediately turning to me and sliding off the white cotton pants I had been staring at for the past few seconds leaving her completely naked before me.

I could almost feel my mouth go dry at the sight before me. Helen, she merely smiled, spread herself out on the floor before me. Stretching out her toes and arms she gave false sigh: "Ahh, now this is relaxation".

I decided to start with her feet first which afforded me the opportunity to take in her full rear whilst rubbing and caressing the soles of her feet. I slowly worked my way up to the top of her thighs finally reaching her bum. We were in delicate territory now. I worked her bum in a circular motion spreading the cheeks and sliding what was at first a rogue finger down between the crack.

Then one became two. Then three fingers and very soon all my forefingers were rubbing pushing up and around her ass hole, each time being met with a moan and a shudder.

Helen continued to take the lead and quite matter of factly informed that: "I think its probably time you took care of my front now honey, don't you?" and wheeled herself over presenting me with a smile, her lovely boobs with nipples standing pert and glistening pussy.

I moved close to the top of her body and said: "You know, if I've to take care of all your front, you're going to have let me rub those lovely boobs of yours Helen". "I'd be very upset if you didn't babe" came the instant reply quickly followed by "you know, I think it's not just me who could do with some tension being released eh?" and placed a hand on my cock, only being held back from extending out towards her by my boxers and denims.

She continued to rub at my zip before popping a button and pulling the zip downwards. I responded by caressing her right breast and teasing the extended nipple. My cock burst forth towards her, as the zip was fully pulled down and I slid my denims down shaking them off behind me as I continued to play with what was now both her both her tits.

The pretence was completely over as she hauled my boxers down and I tore my shirt over my head and flicked off my socks. Now we were both naked on her living room floor.

She wrapped her arms around my neck and pulled me towards her where, eyes closed, our lips locked and we kissed passionately. My hands reached between her legs and I started to finger her pussy. Like her ass hole before, first one, then two and then I forced three inside in her soaking cunt. She pushed towards me and I toyed her pussy, groaning between sharp intakes of breath.

Suddenly she broke from the embrace: "Oh just fuck me now honey. Fuck me hard. Fuck me so hard honey".

I slid on top of her. We were already sweating from our earlier embrace and I moved between her legs and slid my cock deep inside her. She moaned her approval. I did as she asked and forcibly thrust my dick in and out of her pussy faster and faster. Helen writhed in pleasure, her moaning becoming louder and louder.

Our highly enjoyable but long-lasting foreplay ensured that it wouldn't be long before either of us would cum. As I pumped at her pussy the idea grew in my head that having touched, fondled and caressed her almost all of body for the best part of an hour that I rather fancied revisiting those spots and covering them once more, this time with my cum.

Still hammering away at her, this idea manifested itself in a somewhat heavy-breathed: "Can I cum on your tits Helen". The idea met with disapproval. "No, inside...Fill me inside....I'm cumming....Inside....Oahhhhhahhhhhh!!!!!!"

Again I followed her instructions. Soon I came close to reaching my own climax and with one final forceful thrust I spurted waves of my hot cum inside her pussy.

I lay beside her on the carpet, both of us red faced and panting heavily. Again our lips locked in a passionate kiss that last sometime. As the adrenalin continued to wash over me I couldn't help but tell her that I bet she didn't know she helped me achieve my childhood fantasy. "Oh I know honey, I know" she smiled at me.

All the while her hand been gently encouraging my seemingly spent cock to awaken from its slumber and it had become rigid once more thanks to her caressing.

"Your massage" she said with a grin and began wanking me with some increased vigour. Faster, harder she pulled at my again stiff shaft. Helen used her years of experience to quickly bring me to close to cumming before getting on to her knees and motioning to me to stand before her. She stared upwards at me she paused sucked my cock before letting it slide from her mouth. "My tits. Cover them" she ordered and resumed her handy work on my dick.

Little time passed before I was only too happy to follow her command and splashed my second load of cum on the day on to her tight tits.

I stood above admiring the sight of her below me, cum dribbling down her boobs and onto her tight belly while she smiled pleasingly at me.

After a few moments I kissed her forehead and made for the bathroom to go for a pee and Helen did likewise only going to the kitchen for her cigarettes. I heard the click of her lighter as I did my business then washed my hands.

I paused at the doorway as I glanced in and saw Helen spread out on the sofa, her body splattered with copious amounts of my cum. Eyes shut and looking somewhat flushed her right hand brushed her forehead. Her other arm was extended out over the side of the sofa with her cigarette dangling from her hand. A gentle plume of cigarette smoke hovered above her.

How the hell did I get here I thought to myself?