Going Solo with Tina
Going Solo with Tina
It was a chilly Saturday afternoon and after chaining my bike to the drainpipe, I was glad to get inside the clubhouse of the fishing club.
“No dad today Tobias?” enquired Joe the club steward, with a smile as I reached the bar. “No, he got his new car yesterday and has taken my mum to see her aunt in East Grinstead,” I replied, adding, “Wants to clock up some miles to get the engine run in as fast as possible.”
Joe's wife Sadie looked up from polishing the shelves behind the bar. “He’ll certainly clock up a few miles going there and back, so what's dad got now, a Rolls?” said Sadie with a grin. “No, not quite,” I chuckled. “He's got a Rover, 3.5 litres, it's really nice, British Racing Green with a beige, vinyl roof.”
Although I was only sixteen and not old enough to legally drink alcohol, Joe poured me a half pint of shandy and I went over to one of the window tables and looked out at the bleak view of the ocean on this inclement, autumn afternoon. There was no shortage of white horses and as a result the club was quiet, it often was when the sea was rough, with most of the members owning small, glass fibre dinghies which weren't safe in bad weather.
I sat for a while sipping my drink thinking about what to do next. No point in hanging around in an empty clubhouse with no one to talk to, even Joe and Sadie had now disappeared from view.
Just as I picked up the glass to finish my shandy, the clubhouse door opened and in walked Roger Felsham, clad in a stylish sheepskin coat, natty scarf and looking very suave. Roger was in his early twenties and although he looked young, to me he seemed much older, his manner more mature than his years, very much one of the 'chaps' unlike me who often felt like little more than my father's sidekick, but then again, I was still two months shy of my s*******nth birthday.
I guess I was rather in awe of Roger, he was tall and good looking and I rather hoped that in a few years’ time I could be just like him.
“Hello Tobias,” said Roger cheerily as he walked towards the bar, “No dad, today?”
I repeated what I had told Joe and Sadie on my arrival.
“Nice those Rovers, wish I could afford one,” said Roger. “Mind you, my Hillman Avenger does everything I need it to and until my boss decides I can have a new car it'll have to do.”
I knew that Roger was some kind of travelling salesman, but had no idea what it was he actually sold.
Roger reached the bar and rang the old ship’s bell that was mounted on the wall to the side, prompting Joe to reappear. “Good afternoon Joseph, and how are you on this bleak and chilly afternoon?” enquired Roger.
“Oh, not so bad,” responded Joe. “A pint for me please, and whatever young, Master James is drinking,” added Roger, nodding in my direction.
Joining me at the window table, Roger placed another shandy in front of me and sat down opposite. “Bloody cold out there, decided to walk over and didn't realise how biting the wind is,” he said, whilst shrugging his shoulders in testimony to the outside temperature.
“Yes, it is really cold,” I responded. “I cycled over and I could hardly feel my fingers by the time I got here,” I added.
It was reasonably warm in the clubhouse and after we'd chatted for a few minutes Roger stood up and removed his coat, placing it over the back of one of the chairs along with his scarf.
“Fancy a game of bar billiards?” he suggested. I smiled and nodded in response.
“Go on then, set up the mushrooms, old chap,” he said. “I'll show you how it's done.”
I'd always enjoyed Roger's company, he was certainly fun to be around and I'd been lucky enough to go out fishing with him in his boat a couple of times while my dad was away.
Just as we were close to finishing our second game of bar billiards, the door to the clubhouse opened and in walked a young lady named Tina Grant. I hadn't seen Tina for a while as she didn't visit the club that often.
Tina's father, Henry Grant was what my dad referred to as a 'big noise' in the small, seaside town where we lived. He wasn't exactly the most popular of men and owned an engineering factory employing a lot of people in the area, most of whom seemed to dislike him intensely. He was also chairman of the fishing club, not that I'd ever known him to actually go fishing, but he was often in the clubhouse propping up the bar with plenty to say for himself.
Joe quite often had to 'phone Henry Grant's wife to come and collect him as he was prone to becoming drunk and argumentative and in no fit state to drive himself home. He did though, own a Rolls Royce.
Tina, or Miss Grant, as my father insisted I should call her, was no more than nineteen years old, I was fairly sure of this as it was only a year earlier that by chance, I had seen her in her school uniform at the railway station arriving home for the half-term holidays from the boarding school she attended. I had delighted in saying hello to her and had been thrilled when she smiled at me in return.
A few weeks after I'd seen Tina at the station, my father told me that he'd heard that she’d been expelled from school. He didn't know why, he just conjectured that it was probably because she was such an arrogant, naughty, little madam and knowing her, it was likely she'd been up to no good with boys. ‘That school should have given her a damned good caning on that backside of hers in my opinion,’ my father had said.
Like her father, Tina was not overly popular at the fishing club, but she was amazingly attractive with shoulder length, blonde hair and a delightful figure. Unbeknown to my father, his words had only served to increase my fascination for this delightful creature and had prompted me to keep a cutting of a picture of Tina from the local newspaper, taken when she had come runner up in a girls' competition at the local tennis club.
With our second game of bar billiards over it was obvious that Roger was far more interested in directing his attentions to Tina than to me and I certainly couldn't blame him for that. She had arrived in the clubhouse looking very ‘60’s Carnaby Street’, dressed in a very short multi-coloured hooped dress, white leather jacket and matching white, knee high Gogo boots. God, she looked totally stunning and I wondered what she would have thought if she'd known that the sight of her was making my cock begin to swell!
Tina certainly wasn't dressed for the weather, a fact that certainly pleased me and as I returned to my table in the window with my glass of shandy clutched firmly in my hands, my eyes cautiously scrutinised her every inch as she positioned herself on a bar stool with Roger alongside her.
Sat alone as I was, I considered going home, but with sightings of Tina something of a rarity, I decided to hang around and 'absorb' the view. Picking up a newspaper which had been left on an adjacent table, I feigned reading it so that I felt a little less self-conscious just sitting by myself.
The two remained chatting at the bar for some while, with Roger sipping at his beer and Tina drinking a gin and tonic. After a while though, they moved over to the fruit machine and began putting money in, laughing and joking loudly as they did so, Roger for once, appearing less mature than his years. Although the machine paid out a couple of times, it didn't seem long before they had run out of change and Tina decided to challenge Roger to a game of bar billiards instead.
Continuing to feign reading the newspaper, I occasionally glanced in their direction as Roger, it seemed, was in his element teaching Tina the rudiments of the game. She seemed to have little idea how to hold the cue and Roger certainly didn't seem to mind reaching around her waist to give her some guidance.
Tina was not overly tall, average height for a girl at best and as she stretched forward to cue the ball, the shortness of her dress caused it to rise up affording a most welcome view of the lower part of her delightful, peach of a bottom barely covered by the tight, white panties she was wearing. If my cock had shown signs of swelling at the sight of Tina as she arrived in the clubhouse, it had now reached the point of actually throbbing at the sight of her near naked bottom.
Thankful to be shielded by the newspaper, I continued to glance across each time Tina tried to cue the ball, carefully trying to ensure that Roger didn't notice me. She may have reached the final of a tennis competition, but from what I saw of her bar billiard’s skills, I doubted she would ever equal that success in any game involving a cue.
After only one game, it seemed that Tina had had enough of bar billiards and after returning their empty glasses to the bar, Roger retrieved his coat and scarf from the chair alongside me and with a telling smile, said he was off home.
As Roger and Tina left the clubhouse together, I gave it a few moments so as not to seem too obvious, before placing my own empty glass on the bar and heading out of the clubhouse.
After unlocking my bike from the drainpipe, I wheeled it up the steep path towards the road and was just in time to see Tina's powder blue, Triumph TR6 pull away with Roger in the passenger seat.
I knew that Roger lived in a basement flat in one of the many four storey houses along the sea front and as I cycled along that route on my way home it was of little surprise to see the Triumph parked in the street behind Roger's bronze Hillman Avenger estate outside his flat. Lucky old Roger I thought, if Tina's reputation was anything to go by, he was probably preparing to fuck her senseless at this very moment, further increasing my desire to one day be just like him.
With my parents and my older sister in East Grinstead, I delighted in having the house to myself when I returned home, and with the image of Tina so fresh in my mind I wasted little time in making my way upstairs to my bedroom.
Laying on my bed, the power of fantasy began to take hold and as I gently brushed my hand against my cock through my trousers, thoughts of Tina in the dark blue blazer, grey pleated skirt and the white, knee length socks she had been wearing when I'd seen her at the railway station, percolated through my mind. Oh my God, my cock was already rock hard and I hadn't even planned what was in store for Tina yet!
I didn't often have the house to myself and with this rare luxury afforded me, the perfect timing of having the image of the lovely Tina Grant so fresh in my mind just couldn't be allowed to go to waste.
I had masturbated to thoughts of Tina countless times before. The black and white photograph from the newspaper helping to restore her image in my mind each time her luscious body was the inspiration for my fantasy, but the view I'd had of Tina's near naked bottom on this very afternoon, meant that I so wanted to plan a very special scenario for this delicious young woman!
Less than a month before, I'd drooled at the sight of Denise Baker, a decent looking, dark haired girl in my year group who had been sent by Mr Taylor our English teacher, to the Headmistress, Mrs. Abbott.
Denise had failed to hand in her English homework for the second week in a row and returned to class some twenty minutes later with her eyes red and her face heavily tear-stained as she struggled to fight back her sobs. She informed Mr Taylor that she was unable to sit as she had been given the cane, making me so glad that my desk covered the view of the bulge that almost instantly developed in my trousers.
With permission granted by Mr Taylor for Denise to stand for the rest of the lesson, she positioned herself in front of her desk, two rows ahead of me and in the line to my left. For the remainder of the lesson I struggled to keep my eyes from being transfixed on the shapely and doubtless well-striped posterior that molded the back of her regulation grey, pleated skirt so admirably.
I can never be totally sure, but perhaps, just perhaps, Denise’s caning, combined with my father’s unwitting comment that Tina Grant needed her ‘backside’ caned, was what first opened my eyes to an alternative view of this much feared implement.
Kicking off my shoes, I lay on my bed and undid my trousers and along with my underpants slipped them down my legs before rolling over and rummaging to the side of the bed to retrieve one of my old socks from the floor. As I slipped the sock over my rigid member, I began to focus my mind on creating a worthy scenario for the gorgeous Tina Grant whilst slowly 'treading water' with my cock as I processed my thoughts.
Tina must have been caned at school, I was totally convinced of this, after all she had gone to an expensive, posh boarding school, no doubt extremely strict on discipline. At my own school, a mixed private school, the slipper or gym shoe were frequently used on the bottoms of those guilty of what sometimes seemed like relatively innocuous offences. For more serious offences though, it was likely to be the strap, a heavy leather strap which I knew from personal experience, imparted an agonising sting.
The cane wasn't used particularly often, but that in itself added to the fear of ever being on the receiving end of a caning. With the exception of being expelled, the cane was without doubt the ultimate punishment and instilled a level of fear in even the toughest and naughtiest of pupils.
With Tina having reached the point of expulsion, it must have been that all other measures had failed. Yes, Tina's beautiful bottom was probably slippered, strapped and caned again and again before the decision was made to expel her and having been privileged to get a view of that very bottom presented almost bare on that very afternoon, I had little doubt that it would make an appetising target for any implement chosen to be used on her.
Naturally, I had never seen the school that Tina had been expelled from, I wasn't even sure where it was, just that it was some distance away in another part of the country. In my mind, Tina was going to have to be a pupil at my own school and with the addition of some 'artistic licence' she would suffer for her transgressions at the hands of the teachers with whom I was familiar.
I gently teased my hand against my cock as Tina arrived late in the gymnasium dressed in her school uniform aware that the height of my arousal was already such that with very little effort I could so easily cum.
“I'm afraid I'm late Mr Phelps, because I can't find my PE kit anywhere, I think I must have left it at home,” announced Tina in seemingly unapologetic and haughty manner as if the matter was someone else’s fault.
Mr Phelps taught geography and PE and was probably in his late thirties, although diminutive in height he was of muscular build and was certainly not a teacher to trifle with.
“This is the third time you've forgotten your PE kit this term, Grant. You can do it in your underwear this time,” he barked.
Tina's beautiful, full lips, formed a near perfect circle as she processed the thought of stripping to her underwear. “But Sir,” she eventually retorted, “You simply can't make me do PE in my underwear, I totally refuse to do that.”
Mr Phelps was not a man to take no for an answer and moments later Tina was lying face down over the well-worn suede top of the vaulting box, gripping one of its horizontal side bars as Angela Rawlings, a plain and rather irritating girl in my class, was sent to requisition a senior sized plimsoll from lost property.
Gathered with the other members of the class to the side of the gymnasium, I watched in excited anticipation as Angela returned from her errand and handed Mr Phelps a large, shabby, off-white plimsoll, void of its lace.
I was all too aware of the unbearable sting this discarded item of footwear was about to impart on Tina's beautiful, young bottom having suffered the gym shoe on my own behind, on more than one occasion in the past. There was little doubt that the lovely Tina Grant may soon be regretting her decision not to strip to her underwear. Hell, I certainly hoped so!
As Mr Phelps flipped Tina's skirt across her back, I was once again treated to the mouth-watering view of her perfect peach of a bottom presented in tight, white panties which had all but disappeared into her cleft. With Tina’s feet unable to reach the floor, I drooled at the sight of her delicious bare thighs tapering down to her white, knee length socks as her legs hung freely against the side of the vaulting box.
Clasping the plimsoll by the toe end, Mr Phelps wasted little time in offering its heel to Tina's right buttock. Tina remained silent, for once it seemed her superior attitude, unable to find a way of challenging her current situation. Moments later, the simmering teacher began an onslaught of whacks, alternating from one cheek to another, the ample amount of bare flesh on offer his main target, as Tina writhed and contorted to each challenge.
As thud followed thud, the unforgiving, rugged rubber sole of the plimsoll driven by Mr Phelps’s muscular arm, began to take its toll and Tina began to cry out, her protests echoing wildly throughout the hollowness of the gymnasium.
As my arousal grew, I began to work myself ever more enthusiastically, and with my cock rock hard, my eyes became magnetised to the once creamy blank canvas of her beautiful, exposed cheeks as they now displayed an ever deepening, mottled hue.
As the plimsoll continued its challenge, Tina all but climbed headlong over the box, her shapely legs flailing wildly as the plimsoll continued its merciless onslaught.
Suddenly though, it was all over as I gave way to what comes naturally and released into my sock. I lay back on my bed breathing heavily, as the image of Tina’s gloriously reddened buttocks remained in my mind. I wallowed in my pleasure for a few moments before visiting the bathroom, peeing out the dregs of my cum, before rinsing my cock under the tap.
With the right incentive and the privilege of youth, I knew that I was able to masturbate multiple times in quick succession and with the luscious Tina Grant my ‘incentive’ on this day, I had little doubt that I would soon be ready to introduce her to the next phase of her punishment.
Returning to lay back on my bed and with a new sock retrieved from the floor, I began to once more work my cock to hardness. After achieving my goal, I lay there, once more ‘treading water’ as my mind wandered to thoughts of Tina in Roger’s flat. Whilst I was putting her through my fantasies, she was probably naked in his bed as lucky, old Roger Felsham was fucking her for real.
If my calculations were correct, I was only just over two years younger than Tina, reasonably tall for my age and often told I was good looking. The couple who lived a few doors down the street had a much bigger age gap, Joanne was twenty-nine and her husband Keith, only twenty-five.
Perhaps if Roger hadn’t been in the clubhouse when Tina arrived, it could have been me taking her home, she could have been here right now, naked in my bed as I slipped my swollen cock into her beckoning chasm, fucking her for real. After all, I wasn’t totally without experience, having lost my virginity to Kimberly Davis after the school’s beach barbecue at the end of the Summer Term.
As my fantasy built, Tina was again in my class, Mrs Henley’s history class to be precise. The sour and wizened, old history teacher began handing out text books to be shared one between two, pausing only to tell Tina off for turning around and whispering to the girl sat behind her. With the books handed out, instruction was given to read the chapter summarising the reign of Charles 1st.
As the whole class read in reasonable silence, Mrs Henley directed her attentions to writing ten questions in white chalk on the blackboard to be answered in our exercise books on completion of reading. As Mrs Henley advised us after twenty minutes or so that we should be ready to begin the questions, exercise books opened in unison.
A while later though, the silence of the room was broken; “God, this is bloody boring," Tina muttered to Sheila Parsons who was sat next to her, her voice perhaps louder than intended and attracting the attention of Mrs Henley. “Tina Grant, you’ve already been spoken to once, now come out to the front and show me your work.”
With her usual haughty expression, Tina made her way to Mrs Henley’s desk, strutting arrogantly whilst holding her open exercise book in front of her. With a brief glance at Tina’s book enough to deduce that she had done no more than copy the first question from the blackboard, Mrs Henley opened her desk drawer and produced a sturdy leather strap. “Bend over the desk young lady, it’s high time you learnt some respect and to do as you’re told,” growled the teacher.
With the sight of the strap causing Tina’s eyes to widen, she began to protest her pending punishment, my cock growing ever harder as she did so. Tina’s protests though, were to no avail as soon she was bent over the desk, her beautiful bottom poised towards the class as Mrs Henley flipped Tina’s skirt into the small of her back presenting a view reminiscent of the image I held of her bent over the bar billiards table. With her panties drawn tightly into her cleft, Tina, it seemed, was about to flavour the wrath of the strap on the ample bare flesh she inadvertently displayed!
Raising the strap, Mrs Henley brought it down firmly across Tina’s delightful cheeks, and as lick followed lick, Tina began to writhe and cry out in testimony, "OW, OW, OUCH," she yelled repeatedly to the agony that I knew from experience she must be suffering. Mrs. Henley may be wizened, but the ferocity of the onslaught belied the elderly teacher’s slender frame.
As the strapping continued, Tina’s once perfect, unblemished buttocks, began to display a veritable patchwork of red and purple, reminding me of my own bottom when Mr. Sherwood, the Deputy Headmaster had used a similar implement when I had been sent to him for messing about in a science lesson.
Yes, my bottom had hurt like hell and suffered marks which had lasted for ages after Mr. Sherwood’s onslaught and as my mind focused on a similar pattern building on Tina’s beautiful bottom, I once more felt the sweetness of my release into my sock as I could no longer delay the inevitable.
After using the sock to wipe my cock dry, I cast it onto the floor and lay still for a few moments, my arousal all but evaporated for the time being and my cock rapidly shrinking. Slowly but surely though, I began to rekindle my enthusiasm and began to consider the next phase of Tina’s punishment. The sight of her beautiful bottom so revealingly displayed at the fishing club reminding me that I just couldn’t allow this opportunity to go to waste.
Slowly I began to work my cock once more, my earlier exertions having dulled me just a little, but with my mind fixed on my perfect finale for Tina’s punishment I was to feel myself begin to once more rise to the occasion. With my cock erect, I retrieved another sock from the floor and slipped it in place.
I was now stood towards the back of the assembly hall as I struggled through the words in the hymn book I shared with my classmate Daniel Beresford. Ever since my voice had broken, my ability to sing in tune had completely forsaken me. As the whole school strained tunelessly through all five verses of Lord of the Dance, I did my best to join in, but had little option other than to avoid the high notes!
As the final chorus came to a welcome end, Miss Southwood, the music teacher, closed the lid of the piano and Mrs Abbott arose from the semicircle of seats at the back of the stage where all the teachers were sat. Positioning herself at the front of the stage, Mrs Abbott gave permission for hymn books to be closed, the middle-aged headmistress then beginning the spiel which I had heard many times before, about the displeasure of having to administer corporal punishment to any pupil at the school. With the ‘spiel’ over, Tina was ordered to face her punishment. “Tina Grant, please make your way up to the stage,” said Mrs Abbott, her voice solemn and commanding.
After some whispering from the girls stood closest to her, Tina eventually emerged from amidst the sea of blue blazers at the back of the hall and began to walk slowly down the centre aisle, even at this bleak moment her arrogance still evident in her step as the solid, block heels of her Gogo boots against the oak floor caused an echoing in the rafters of the high, vaulted ceiling of the hall with every step that she took. God, she looked utterly amazing!
All eyes were on Tina as she reached the stage and slowly climbed the wooden steps to the side, my own eyes focused on the roundness of her beautiful, peachy behind so deliciously packaged within the short, grey pleated skirt that barely covered the tops of her thighs.
After a few moments of verbal chastisement over the ‘insolence and disgraceful behaviour’ that Tina had displayed since arriving at the school, Mrs Abbott informed her she was ‘within an inch’ of being expelled and she had no alternative other than to cane her. My anticipation of the punishment she was about to endure causing my cock to grow ever harder.
As Tina stood centre stage with her back to her fellow pupils, my eyes began to focus on her bare, naked thighs, such beautiful thighs tapering down to those gloriously sexy Gogo boots that she had worn at the fishing club.
As I steadily worked my cock, I recalled being at my classmate Matthew Knight’s house after school one day. Francis Doubleday, another boy in my class, had been given the cane that afternoon for fighting in the playground and Matthew had told his mother about the caning. Mrs Knight’s response was to volunteer the story of when she had been caned at school, six strokes on the back of her bare thighs for flicking mashed potato in the dining hall at a girl she didn’t get on with. She had laughed about this, but admitted that it had been incredibly painful and had left her with the stripes on her thighs that lasted for almost a fortnight.
Matthew’s mum was very attractive and although in her late thirties, seemed much younger. I guess I had a bit of a crush on her and her story really aroused me. That very evening in the privacy of my bedroom, I had ashamedly masturbated to thoughts of Mrs Knight’s caning! Hell, whatever would Matthew have thought of me if he’d known I’d actually wanked about his mother?
“Bend over and grasp your ankles Grant,” ordered Mrs Abbott sternly, as my focus returned to Tina.
Despite her arrogance even Tina knew that not to do as instructed would only make matters worse and moments later with the back of her skirt raised and tucked into its own waistband, Mrs Abbott unceremoniously tugged Tina’s panties down to her knees as the whole school gasped in unison as Tina’s beautiful, naked bottom became so publicly displayed. As I hastily glanced around the hall, the expressions on the faces of my fellow pupils at this spectacle, displayed emotions which ranged from total amusement to absolute horror as well as somewhere in between.
With Tina in position, Mr Sherwood left his chair and handed the Headmistress the senior cane. “You’re going to receive a very hard caning Grant, and if there isn’t an immediate improvement in your behaviour and attitude, I will seriously have to consider your future at this school. Do I make myself clear?” growled Mrs Abbott.
“Yes Miss, perfectly clear,” responded Tina, her tone almost impudent, belying the fact that her bare bottom was on display to the entire school.
Offering the cane to the centre of Tina’s bottom, the Headmistress raised it high above her shoulder, bringing it down with a resounding crack across the centre of her glorious cheeks. “OH, AH, AH,” yelled Tina releasing the grip on her ankles and rising up slightly before quickly returning to position.
The second stroke was placed parallel to the first and slightly lower, landing with another ‘explosive’ crack just above the point where buttock meets thigh. Tina noisily drew in breath through her teeth before giving way to a cry of, “Eee-ow-ow-ow!” as she fought to stay in position.
There was little doubt that the Headmistress was determined to make Tina pay for her bad behaviour and as she got into her stride, stroke followed stroke as Tina wriggled, writhed and cried out to her anguish.
Tina was without doubt taking one hell of a caning and as the strokes continued to rain down on the very bottom with which I had become so totally obsessed, I worked my cock ever more enthusiastically, delighting in the image of the angry welts which now embossed Tina’s buttocks. At this time, they were the most perfect buttocks imaginable to me and as I held the image of her bent over the bar billiards table, I delighted in the thought of being alone with Tina in the clubhouse as it was me wielding the cane against those beautiful cheeks!
As Mrs Abbott continued her quest, the sound of the cane meeting Tina’s delicious flesh reverberated like a pistol shot high in the rafters of the school hall, interspersed with the echoing of her squeals and shrieks, bearing testimony to the agony she was enduring.
As each new stroke added yet another angry stripe, Tina’s buttocks became ravaged, the once perfect, creamy smooth contours of her cheeks now displaying a ragged mix of red and purple hues. With each new stroke compounding her agony, Tina’s grip on her ankles became an impossible task as her arms flailed wildly to her sides and her knees flexed and straightened causing her bottom to rise and fall as she attempted to quell her anguish. Working my cock ever more vigorously, I grew closer to the brink, but with one more task required of Tina, I slowed myself down to delay that inevitable outcome.
Suddenly, Tina was above me on my bed 69’ing with me, her knees astride my head as her beautiful, caned bottom in all its naked, colourful glory, was close to my face as she bore down on my throbbing cock.
As my tongue tasted the delicious juices which flowed from her vagina, my fingers traversed her wounded buttocks, delighting in the feel of the vivid, swollen ridges the cane had so mercilessly embossed on her. Tina groaned as my attentions reignited the pain of her torment and as she sucked me ever more vigorously, I gripped her pretty head between my thighs, manipulating my hips to drive my cock deep into her moist and eager mouth. The feel of her perfect teeth against my cock as I did so, slightly hurting, yet blissfully pleasurable as I rode within her.
With Tina’s neatly puckered anus beckoning my attention I offered the tip of my tongue to this enticing orifice, tasting its flavour as I poised my index finger ready to insert to the hilt. As my finger travelled through her sphincter, I reached the point of no return and although I wanted this fantasy to last forever, I once more felt myself release. Yes, in my fantasy, I had cum in the luscious Tina Grant’s glorious mouth with my finger in her arsehole!
With my fantasy over, I cast off the plain, black sock I had utilised for my purpose and lay back on my bed breathing heavily as I focused on my still swollen cock, imagining that one day perhaps, I may just get to fuck Tina for real. If Tina really was the easy lay her reputation suggested, I wondered how my own cock would compare to the ones that had gone before me!
Perhaps one day I would actually find out, only time would tell, but what I did know for sure was that until I was graced with seeing this luscious young woman again, I would be taking her on many more adventures in my fantasies before that time.
It was a chilly Saturday afternoon and after chaining my bike to the drainpipe, I was glad to get inside the clubhouse of the fishing club.
“No dad today Tobias?” enquired Joe the club steward, with a smile as I reached the bar. “No, he got his new car yesterday and has taken my mum to see her aunt in East Grinstead,” I replied, adding, “Wants to clock up some miles to get the engine run in as fast as possible.”
Joe's wife Sadie looked up from polishing the shelves behind the bar. “He’ll certainly clock up a few miles going there and back, so what's dad got now, a Rolls?” said Sadie with a grin. “No, not quite,” I chuckled. “He's got a Rover, 3.5 litres, it's really nice, British Racing Green with a beige, vinyl roof.”
Although I was only sixteen and not old enough to legally drink alcohol, Joe poured me a half pint of shandy and I went over to one of the window tables and looked out at the bleak view of the ocean on this inclement, autumn afternoon. There was no shortage of white horses and as a result the club was quiet, it often was when the sea was rough, with most of the members owning small, glass fibre dinghies which weren't safe in bad weather.
I sat for a while sipping my drink thinking about what to do next. No point in hanging around in an empty clubhouse with no one to talk to, even Joe and Sadie had now disappeared from view.
Just as I picked up the glass to finish my shandy, the clubhouse door opened and in walked Roger Felsham, clad in a stylish sheepskin coat, natty scarf and looking very suave. Roger was in his early twenties and although he looked young, to me he seemed much older, his manner more mature than his years, very much one of the 'chaps' unlike me who often felt like little more than my father's sidekick, but then again, I was still two months shy of my s*******nth birthday.
I guess I was rather in awe of Roger, he was tall and good looking and I rather hoped that in a few years’ time I could be just like him.
“Hello Tobias,” said Roger cheerily as he walked towards the bar, “No dad, today?”
I repeated what I had told Joe and Sadie on my arrival.
“Nice those Rovers, wish I could afford one,” said Roger. “Mind you, my Hillman Avenger does everything I need it to and until my boss decides I can have a new car it'll have to do.”
I knew that Roger was some kind of travelling salesman, but had no idea what it was he actually sold.
Roger reached the bar and rang the old ship’s bell that was mounted on the wall to the side, prompting Joe to reappear. “Good afternoon Joseph, and how are you on this bleak and chilly afternoon?” enquired Roger.
“Oh, not so bad,” responded Joe. “A pint for me please, and whatever young, Master James is drinking,” added Roger, nodding in my direction.
Joining me at the window table, Roger placed another shandy in front of me and sat down opposite. “Bloody cold out there, decided to walk over and didn't realise how biting the wind is,” he said, whilst shrugging his shoulders in testimony to the outside temperature.
“Yes, it is really cold,” I responded. “I cycled over and I could hardly feel my fingers by the time I got here,” I added.
It was reasonably warm in the clubhouse and after we'd chatted for a few minutes Roger stood up and removed his coat, placing it over the back of one of the chairs along with his scarf.
“Fancy a game of bar billiards?” he suggested. I smiled and nodded in response.
“Go on then, set up the mushrooms, old chap,” he said. “I'll show you how it's done.”
I'd always enjoyed Roger's company, he was certainly fun to be around and I'd been lucky enough to go out fishing with him in his boat a couple of times while my dad was away.
Just as we were close to finishing our second game of bar billiards, the door to the clubhouse opened and in walked a young lady named Tina Grant. I hadn't seen Tina for a while as she didn't visit the club that often.
Tina's father, Henry Grant was what my dad referred to as a 'big noise' in the small, seaside town where we lived. He wasn't exactly the most popular of men and owned an engineering factory employing a lot of people in the area, most of whom seemed to dislike him intensely. He was also chairman of the fishing club, not that I'd ever known him to actually go fishing, but he was often in the clubhouse propping up the bar with plenty to say for himself.
Joe quite often had to 'phone Henry Grant's wife to come and collect him as he was prone to becoming drunk and argumentative and in no fit state to drive himself home. He did though, own a Rolls Royce.
Tina, or Miss Grant, as my father insisted I should call her, was no more than nineteen years old, I was fairly sure of this as it was only a year earlier that by chance, I had seen her in her school uniform at the railway station arriving home for the half-term holidays from the boarding school she attended. I had delighted in saying hello to her and had been thrilled when she smiled at me in return.
A few weeks after I'd seen Tina at the station, my father told me that he'd heard that she’d been expelled from school. He didn't know why, he just conjectured that it was probably because she was such an arrogant, naughty, little madam and knowing her, it was likely she'd been up to no good with boys. ‘That school should have given her a damned good caning on that backside of hers in my opinion,’ my father had said.
Like her father, Tina was not overly popular at the fishing club, but she was amazingly attractive with shoulder length, blonde hair and a delightful figure. Unbeknown to my father, his words had only served to increase my fascination for this delightful creature and had prompted me to keep a cutting of a picture of Tina from the local newspaper, taken when she had come runner up in a girls' competition at the local tennis club.
With our second game of bar billiards over it was obvious that Roger was far more interested in directing his attentions to Tina than to me and I certainly couldn't blame him for that. She had arrived in the clubhouse looking very ‘60’s Carnaby Street’, dressed in a very short multi-coloured hooped dress, white leather jacket and matching white, knee high Gogo boots. God, she looked totally stunning and I wondered what she would have thought if she'd known that the sight of her was making my cock begin to swell!
Tina certainly wasn't dressed for the weather, a fact that certainly pleased me and as I returned to my table in the window with my glass of shandy clutched firmly in my hands, my eyes cautiously scrutinised her every inch as she positioned herself on a bar stool with Roger alongside her.
Sat alone as I was, I considered going home, but with sightings of Tina something of a rarity, I decided to hang around and 'absorb' the view. Picking up a newspaper which had been left on an adjacent table, I feigned reading it so that I felt a little less self-conscious just sitting by myself.
The two remained chatting at the bar for some while, with Roger sipping at his beer and Tina drinking a gin and tonic. After a while though, they moved over to the fruit machine and began putting money in, laughing and joking loudly as they did so, Roger for once, appearing less mature than his years. Although the machine paid out a couple of times, it didn't seem long before they had run out of change and Tina decided to challenge Roger to a game of bar billiards instead.
Continuing to feign reading the newspaper, I occasionally glanced in their direction as Roger, it seemed, was in his element teaching Tina the rudiments of the game. She seemed to have little idea how to hold the cue and Roger certainly didn't seem to mind reaching around her waist to give her some guidance.
Tina was not overly tall, average height for a girl at best and as she stretched forward to cue the ball, the shortness of her dress caused it to rise up affording a most welcome view of the lower part of her delightful, peach of a bottom barely covered by the tight, white panties she was wearing. If my cock had shown signs of swelling at the sight of Tina as she arrived in the clubhouse, it had now reached the point of actually throbbing at the sight of her near naked bottom.
Thankful to be shielded by the newspaper, I continued to glance across each time Tina tried to cue the ball, carefully trying to ensure that Roger didn't notice me. She may have reached the final of a tennis competition, but from what I saw of her bar billiard’s skills, I doubted she would ever equal that success in any game involving a cue.
After only one game, it seemed that Tina had had enough of bar billiards and after returning their empty glasses to the bar, Roger retrieved his coat and scarf from the chair alongside me and with a telling smile, said he was off home.
As Roger and Tina left the clubhouse together, I gave it a few moments so as not to seem too obvious, before placing my own empty glass on the bar and heading out of the clubhouse.
After unlocking my bike from the drainpipe, I wheeled it up the steep path towards the road and was just in time to see Tina's powder blue, Triumph TR6 pull away with Roger in the passenger seat.
I knew that Roger lived in a basement flat in one of the many four storey houses along the sea front and as I cycled along that route on my way home it was of little surprise to see the Triumph parked in the street behind Roger's bronze Hillman Avenger estate outside his flat. Lucky old Roger I thought, if Tina's reputation was anything to go by, he was probably preparing to fuck her senseless at this very moment, further increasing my desire to one day be just like him.
With my parents and my older sister in East Grinstead, I delighted in having the house to myself when I returned home, and with the image of Tina so fresh in my mind I wasted little time in making my way upstairs to my bedroom.
Laying on my bed, the power of fantasy began to take hold and as I gently brushed my hand against my cock through my trousers, thoughts of Tina in the dark blue blazer, grey pleated skirt and the white, knee length socks she had been wearing when I'd seen her at the railway station, percolated through my mind. Oh my God, my cock was already rock hard and I hadn't even planned what was in store for Tina yet!
I didn't often have the house to myself and with this rare luxury afforded me, the perfect timing of having the image of the lovely Tina Grant so fresh in my mind just couldn't be allowed to go to waste.
I had masturbated to thoughts of Tina countless times before. The black and white photograph from the newspaper helping to restore her image in my mind each time her luscious body was the inspiration for my fantasy, but the view I'd had of Tina's near naked bottom on this very afternoon, meant that I so wanted to plan a very special scenario for this delicious young woman!
Less than a month before, I'd drooled at the sight of Denise Baker, a decent looking, dark haired girl in my year group who had been sent by Mr Taylor our English teacher, to the Headmistress, Mrs. Abbott.
Denise had failed to hand in her English homework for the second week in a row and returned to class some twenty minutes later with her eyes red and her face heavily tear-stained as she struggled to fight back her sobs. She informed Mr Taylor that she was unable to sit as she had been given the cane, making me so glad that my desk covered the view of the bulge that almost instantly developed in my trousers.
With permission granted by Mr Taylor for Denise to stand for the rest of the lesson, she positioned herself in front of her desk, two rows ahead of me and in the line to my left. For the remainder of the lesson I struggled to keep my eyes from being transfixed on the shapely and doubtless well-striped posterior that molded the back of her regulation grey, pleated skirt so admirably.
I can never be totally sure, but perhaps, just perhaps, Denise’s caning, combined with my father’s unwitting comment that Tina Grant needed her ‘backside’ caned, was what first opened my eyes to an alternative view of this much feared implement.
Kicking off my shoes, I lay on my bed and undid my trousers and along with my underpants slipped them down my legs before rolling over and rummaging to the side of the bed to retrieve one of my old socks from the floor. As I slipped the sock over my rigid member, I began to focus my mind on creating a worthy scenario for the gorgeous Tina Grant whilst slowly 'treading water' with my cock as I processed my thoughts.
Tina must have been caned at school, I was totally convinced of this, after all she had gone to an expensive, posh boarding school, no doubt extremely strict on discipline. At my own school, a mixed private school, the slipper or gym shoe were frequently used on the bottoms of those guilty of what sometimes seemed like relatively innocuous offences. For more serious offences though, it was likely to be the strap, a heavy leather strap which I knew from personal experience, imparted an agonising sting.
The cane wasn't used particularly often, but that in itself added to the fear of ever being on the receiving end of a caning. With the exception of being expelled, the cane was without doubt the ultimate punishment and instilled a level of fear in even the toughest and naughtiest of pupils.
With Tina having reached the point of expulsion, it must have been that all other measures had failed. Yes, Tina's beautiful bottom was probably slippered, strapped and caned again and again before the decision was made to expel her and having been privileged to get a view of that very bottom presented almost bare on that very afternoon, I had little doubt that it would make an appetising target for any implement chosen to be used on her.
Naturally, I had never seen the school that Tina had been expelled from, I wasn't even sure where it was, just that it was some distance away in another part of the country. In my mind, Tina was going to have to be a pupil at my own school and with the addition of some 'artistic licence' she would suffer for her transgressions at the hands of the teachers with whom I was familiar.
I gently teased my hand against my cock as Tina arrived late in the gymnasium dressed in her school uniform aware that the height of my arousal was already such that with very little effort I could so easily cum.
“I'm afraid I'm late Mr Phelps, because I can't find my PE kit anywhere, I think I must have left it at home,” announced Tina in seemingly unapologetic and haughty manner as if the matter was someone else’s fault.
Mr Phelps taught geography and PE and was probably in his late thirties, although diminutive in height he was of muscular build and was certainly not a teacher to trifle with.
“This is the third time you've forgotten your PE kit this term, Grant. You can do it in your underwear this time,” he barked.
Tina's beautiful, full lips, formed a near perfect circle as she processed the thought of stripping to her underwear. “But Sir,” she eventually retorted, “You simply can't make me do PE in my underwear, I totally refuse to do that.”
Mr Phelps was not a man to take no for an answer and moments later Tina was lying face down over the well-worn suede top of the vaulting box, gripping one of its horizontal side bars as Angela Rawlings, a plain and rather irritating girl in my class, was sent to requisition a senior sized plimsoll from lost property.
Gathered with the other members of the class to the side of the gymnasium, I watched in excited anticipation as Angela returned from her errand and handed Mr Phelps a large, shabby, off-white plimsoll, void of its lace.
I was all too aware of the unbearable sting this discarded item of footwear was about to impart on Tina's beautiful, young bottom having suffered the gym shoe on my own behind, on more than one occasion in the past. There was little doubt that the lovely Tina Grant may soon be regretting her decision not to strip to her underwear. Hell, I certainly hoped so!
As Mr Phelps flipped Tina's skirt across her back, I was once again treated to the mouth-watering view of her perfect peach of a bottom presented in tight, white panties which had all but disappeared into her cleft. With Tina’s feet unable to reach the floor, I drooled at the sight of her delicious bare thighs tapering down to her white, knee length socks as her legs hung freely against the side of the vaulting box.
Clasping the plimsoll by the toe end, Mr Phelps wasted little time in offering its heel to Tina's right buttock. Tina remained silent, for once it seemed her superior attitude, unable to find a way of challenging her current situation. Moments later, the simmering teacher began an onslaught of whacks, alternating from one cheek to another, the ample amount of bare flesh on offer his main target, as Tina writhed and contorted to each challenge.
As thud followed thud, the unforgiving, rugged rubber sole of the plimsoll driven by Mr Phelps’s muscular arm, began to take its toll and Tina began to cry out, her protests echoing wildly throughout the hollowness of the gymnasium.
As my arousal grew, I began to work myself ever more enthusiastically, and with my cock rock hard, my eyes became magnetised to the once creamy blank canvas of her beautiful, exposed cheeks as they now displayed an ever deepening, mottled hue.
As the plimsoll continued its challenge, Tina all but climbed headlong over the box, her shapely legs flailing wildly as the plimsoll continued its merciless onslaught.
Suddenly though, it was all over as I gave way to what comes naturally and released into my sock. I lay back on my bed breathing heavily, as the image of Tina’s gloriously reddened buttocks remained in my mind. I wallowed in my pleasure for a few moments before visiting the bathroom, peeing out the dregs of my cum, before rinsing my cock under the tap.
With the right incentive and the privilege of youth, I knew that I was able to masturbate multiple times in quick succession and with the luscious Tina Grant my ‘incentive’ on this day, I had little doubt that I would soon be ready to introduce her to the next phase of her punishment.
Returning to lay back on my bed and with a new sock retrieved from the floor, I began to once more work my cock to hardness. After achieving my goal, I lay there, once more ‘treading water’ as my mind wandered to thoughts of Tina in Roger’s flat. Whilst I was putting her through my fantasies, she was probably naked in his bed as lucky, old Roger Felsham was fucking her for real.
If my calculations were correct, I was only just over two years younger than Tina, reasonably tall for my age and often told I was good looking. The couple who lived a few doors down the street had a much bigger age gap, Joanne was twenty-nine and her husband Keith, only twenty-five.
Perhaps if Roger hadn’t been in the clubhouse when Tina arrived, it could have been me taking her home, she could have been here right now, naked in my bed as I slipped my swollen cock into her beckoning chasm, fucking her for real. After all, I wasn’t totally without experience, having lost my virginity to Kimberly Davis after the school’s beach barbecue at the end of the Summer Term.
As my fantasy built, Tina was again in my class, Mrs Henley’s history class to be precise. The sour and wizened, old history teacher began handing out text books to be shared one between two, pausing only to tell Tina off for turning around and whispering to the girl sat behind her. With the books handed out, instruction was given to read the chapter summarising the reign of Charles 1st.
As the whole class read in reasonable silence, Mrs Henley directed her attentions to writing ten questions in white chalk on the blackboard to be answered in our exercise books on completion of reading. As Mrs Henley advised us after twenty minutes or so that we should be ready to begin the questions, exercise books opened in unison.
A while later though, the silence of the room was broken; “God, this is bloody boring," Tina muttered to Sheila Parsons who was sat next to her, her voice perhaps louder than intended and attracting the attention of Mrs Henley. “Tina Grant, you’ve already been spoken to once, now come out to the front and show me your work.”
With her usual haughty expression, Tina made her way to Mrs Henley’s desk, strutting arrogantly whilst holding her open exercise book in front of her. With a brief glance at Tina’s book enough to deduce that she had done no more than copy the first question from the blackboard, Mrs Henley opened her desk drawer and produced a sturdy leather strap. “Bend over the desk young lady, it’s high time you learnt some respect and to do as you’re told,” growled the teacher.
With the sight of the strap causing Tina’s eyes to widen, she began to protest her pending punishment, my cock growing ever harder as she did so. Tina’s protests though, were to no avail as soon she was bent over the desk, her beautiful bottom poised towards the class as Mrs Henley flipped Tina’s skirt into the small of her back presenting a view reminiscent of the image I held of her bent over the bar billiards table. With her panties drawn tightly into her cleft, Tina, it seemed, was about to flavour the wrath of the strap on the ample bare flesh she inadvertently displayed!
Raising the strap, Mrs Henley brought it down firmly across Tina’s delightful cheeks, and as lick followed lick, Tina began to writhe and cry out in testimony, "OW, OW, OUCH," she yelled repeatedly to the agony that I knew from experience she must be suffering. Mrs. Henley may be wizened, but the ferocity of the onslaught belied the elderly teacher’s slender frame.
As the strapping continued, Tina’s once perfect, unblemished buttocks, began to display a veritable patchwork of red and purple, reminding me of my own bottom when Mr. Sherwood, the Deputy Headmaster had used a similar implement when I had been sent to him for messing about in a science lesson.
Yes, my bottom had hurt like hell and suffered marks which had lasted for ages after Mr. Sherwood’s onslaught and as my mind focused on a similar pattern building on Tina’s beautiful bottom, I once more felt the sweetness of my release into my sock as I could no longer delay the inevitable.
After using the sock to wipe my cock dry, I cast it onto the floor and lay still for a few moments, my arousal all but evaporated for the time being and my cock rapidly shrinking. Slowly but surely though, I began to rekindle my enthusiasm and began to consider the next phase of Tina’s punishment. The sight of her beautiful bottom so revealingly displayed at the fishing club reminding me that I just couldn’t allow this opportunity to go to waste.
Slowly I began to work my cock once more, my earlier exertions having dulled me just a little, but with my mind fixed on my perfect finale for Tina’s punishment I was to feel myself begin to once more rise to the occasion. With my cock erect, I retrieved another sock from the floor and slipped it in place.
I was now stood towards the back of the assembly hall as I struggled through the words in the hymn book I shared with my classmate Daniel Beresford. Ever since my voice had broken, my ability to sing in tune had completely forsaken me. As the whole school strained tunelessly through all five verses of Lord of the Dance, I did my best to join in, but had little option other than to avoid the high notes!
As the final chorus came to a welcome end, Miss Southwood, the music teacher, closed the lid of the piano and Mrs Abbott arose from the semicircle of seats at the back of the stage where all the teachers were sat. Positioning herself at the front of the stage, Mrs Abbott gave permission for hymn books to be closed, the middle-aged headmistress then beginning the spiel which I had heard many times before, about the displeasure of having to administer corporal punishment to any pupil at the school. With the ‘spiel’ over, Tina was ordered to face her punishment. “Tina Grant, please make your way up to the stage,” said Mrs Abbott, her voice solemn and commanding.
After some whispering from the girls stood closest to her, Tina eventually emerged from amidst the sea of blue blazers at the back of the hall and began to walk slowly down the centre aisle, even at this bleak moment her arrogance still evident in her step as the solid, block heels of her Gogo boots against the oak floor caused an echoing in the rafters of the high, vaulted ceiling of the hall with every step that she took. God, she looked utterly amazing!
All eyes were on Tina as she reached the stage and slowly climbed the wooden steps to the side, my own eyes focused on the roundness of her beautiful, peachy behind so deliciously packaged within the short, grey pleated skirt that barely covered the tops of her thighs.
After a few moments of verbal chastisement over the ‘insolence and disgraceful behaviour’ that Tina had displayed since arriving at the school, Mrs Abbott informed her she was ‘within an inch’ of being expelled and she had no alternative other than to cane her. My anticipation of the punishment she was about to endure causing my cock to grow ever harder.
As Tina stood centre stage with her back to her fellow pupils, my eyes began to focus on her bare, naked thighs, such beautiful thighs tapering down to those gloriously sexy Gogo boots that she had worn at the fishing club.
As I steadily worked my cock, I recalled being at my classmate Matthew Knight’s house after school one day. Francis Doubleday, another boy in my class, had been given the cane that afternoon for fighting in the playground and Matthew had told his mother about the caning. Mrs Knight’s response was to volunteer the story of when she had been caned at school, six strokes on the back of her bare thighs for flicking mashed potato in the dining hall at a girl she didn’t get on with. She had laughed about this, but admitted that it had been incredibly painful and had left her with the stripes on her thighs that lasted for almost a fortnight.
Matthew’s mum was very attractive and although in her late thirties, seemed much younger. I guess I had a bit of a crush on her and her story really aroused me. That very evening in the privacy of my bedroom, I had ashamedly masturbated to thoughts of Mrs Knight’s caning! Hell, whatever would Matthew have thought of me if he’d known I’d actually wanked about his mother?
“Bend over and grasp your ankles Grant,” ordered Mrs Abbott sternly, as my focus returned to Tina.
Despite her arrogance even Tina knew that not to do as instructed would only make matters worse and moments later with the back of her skirt raised and tucked into its own waistband, Mrs Abbott unceremoniously tugged Tina’s panties down to her knees as the whole school gasped in unison as Tina’s beautiful, naked bottom became so publicly displayed. As I hastily glanced around the hall, the expressions on the faces of my fellow pupils at this spectacle, displayed emotions which ranged from total amusement to absolute horror as well as somewhere in between.
With Tina in position, Mr Sherwood left his chair and handed the Headmistress the senior cane. “You’re going to receive a very hard caning Grant, and if there isn’t an immediate improvement in your behaviour and attitude, I will seriously have to consider your future at this school. Do I make myself clear?” growled Mrs Abbott.
“Yes Miss, perfectly clear,” responded Tina, her tone almost impudent, belying the fact that her bare bottom was on display to the entire school.
Offering the cane to the centre of Tina’s bottom, the Headmistress raised it high above her shoulder, bringing it down with a resounding crack across the centre of her glorious cheeks. “OH, AH, AH,” yelled Tina releasing the grip on her ankles and rising up slightly before quickly returning to position.
The second stroke was placed parallel to the first and slightly lower, landing with another ‘explosive’ crack just above the point where buttock meets thigh. Tina noisily drew in breath through her teeth before giving way to a cry of, “Eee-ow-ow-ow!” as she fought to stay in position.
There was little doubt that the Headmistress was determined to make Tina pay for her bad behaviour and as she got into her stride, stroke followed stroke as Tina wriggled, writhed and cried out to her anguish.
Tina was without doubt taking one hell of a caning and as the strokes continued to rain down on the very bottom with which I had become so totally obsessed, I worked my cock ever more enthusiastically, delighting in the image of the angry welts which now embossed Tina’s buttocks. At this time, they were the most perfect buttocks imaginable to me and as I held the image of her bent over the bar billiards table, I delighted in the thought of being alone with Tina in the clubhouse as it was me wielding the cane against those beautiful cheeks!
As Mrs Abbott continued her quest, the sound of the cane meeting Tina’s delicious flesh reverberated like a pistol shot high in the rafters of the school hall, interspersed with the echoing of her squeals and shrieks, bearing testimony to the agony she was enduring.
As each new stroke added yet another angry stripe, Tina’s buttocks became ravaged, the once perfect, creamy smooth contours of her cheeks now displaying a ragged mix of red and purple hues. With each new stroke compounding her agony, Tina’s grip on her ankles became an impossible task as her arms flailed wildly to her sides and her knees flexed and straightened causing her bottom to rise and fall as she attempted to quell her anguish. Working my cock ever more vigorously, I grew closer to the brink, but with one more task required of Tina, I slowed myself down to delay that inevitable outcome.
Suddenly, Tina was above me on my bed 69’ing with me, her knees astride my head as her beautiful, caned bottom in all its naked, colourful glory, was close to my face as she bore down on my throbbing cock.
As my tongue tasted the delicious juices which flowed from her vagina, my fingers traversed her wounded buttocks, delighting in the feel of the vivid, swollen ridges the cane had so mercilessly embossed on her. Tina groaned as my attentions reignited the pain of her torment and as she sucked me ever more vigorously, I gripped her pretty head between my thighs, manipulating my hips to drive my cock deep into her moist and eager mouth. The feel of her perfect teeth against my cock as I did so, slightly hurting, yet blissfully pleasurable as I rode within her.
With Tina’s neatly puckered anus beckoning my attention I offered the tip of my tongue to this enticing orifice, tasting its flavour as I poised my index finger ready to insert to the hilt. As my finger travelled through her sphincter, I reached the point of no return and although I wanted this fantasy to last forever, I once more felt myself release. Yes, in my fantasy, I had cum in the luscious Tina Grant’s glorious mouth with my finger in her arsehole!
With my fantasy over, I cast off the plain, black sock I had utilised for my purpose and lay back on my bed breathing heavily as I focused on my still swollen cock, imagining that one day perhaps, I may just get to fuck Tina for real. If Tina really was the easy lay her reputation suggested, I wondered how my own cock would compare to the ones that had gone before me!
Perhaps one day I would actually find out, only time would tell, but what I did know for sure was that until I was graced with seeing this luscious young woman again, I would be taking her on many more adventures in my fantasies before that time.
5 years ago
