His First Time Almost Wasn’t Pt. 01

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After a long break, I’ve decided to post a few more stories from time to time. As stated in my profile, most of my stories start with a slow but erotic build-up of tension. If this isn’t your thing, you’ve been advised.

This is the first part of such a story that will be resolved in Part 2. The scenario, female character, and fixation are true, though the narrative sadly isn’t. That’s why I’ve included the reference to porn magazines rather than internet or movie porn.


On the outward journey his heart was thumping in anticipation of the journey home. His parents didn’t drive, and a friend of theirs, Brenda, had offered to take his grandparents back home after their brief stay. His mother had suggested that he tag along for the ride to keep Brenda company on the way back. He wasn’t sure of the distance, but the journey would take nearly an hour and a half each way.


Although not particularly attractive, though she wasn’t ugly either. She was in her late thirties (he was nineteen), and slightly plump, with fleshy legs and thighs. Her hair was fairly short and wavy, dark though flecked with a little grey. Her face was slightly plump, too, and she wore no makeup. Her average sized breasts looked shapely and inviting, and he guessed that they were probably B-cup in size.


She often gave him a lift to college, as her route to work took her past the bus stop where he was often waiting.


He was ashamed to admit to himself that, despite her having been a family friend for many years he had started to see her in a different light recently. He hated himself for ogling her – and hoped she didn’t notice. He sensed that his newly kindled desire for her probably came largely from being alone with her. It was unthinkable to make any kind of move, of course. Quite apart from the outraged reaction of his parents that it would provoke, she was a likeable lady whom he would not wish to offend.

And yet…

Each time he got into the car with her it was a kind of delicious torture. Her thighs were so close to his, and his hands were just inches from them, and from her breasts, too. She didn’t dress glamorously for work, but her skirts reached just short of her knees, and when she was driving it inevitably rode up. He found his gaze drawn repeatedly – though fleetingly – to her knees, her bared mid thighs, and to her breasts as she drove. She was good at making small talk and he was able to brood on his own thoughts and simply speak a few words when she paused.

He blushed to recall that the first time he had masturbated to a porn magazine his mind had somehow but powerfully called her to mind. Disturbingly yet exquisitely the breasts and parted legs on the quivering page over which his eyes roved had become hers. He had found himself thinking about her more and more until she became a fixation.

He LONGED to have sex with her. He could half imagine the two of them going at it. And he began to masturbate to the thought, calling to mind her face and her body, and imagining her soft, lisping voice as she spoke and whimpered her approval of his caresses, his penetration and his thrusting. She was fairly prim, and this added to the appeal; to his shame he imagined her being uncharacteristically wanton. As he thumbed through his porn magazines he asked himself which breasts hers would most resemble. And his imagination didn’t stop with her breasts.

One day he was sure she had caught him looking at her breasts. She said nothing but held his gaze for a few moments and he knew he was blushing deeply. For the next few days he made a point of catching an earlier bus to college to avoid her.

But of course, despite his embarrassment and shame he wanted to be next to her again, and after just over a week he resumed his usual time. And, as often as not, she would see him waiting there and pull in to give him a lift.

He had now resolved to ogle her far less, but was not surprised when he was unable to do so. He tried to be more discreet instead. And he was always glad of his holdall containing his college stuff. It hid his erection which came on within minutes of getting into her car. She made no reference to him looking at her, and her skirt continued to ride part way up her fleshy thighs without her attempting to stop it, so he told Escort Kız himself that either she had been unaware of his leers or that at least she wasn’t offended.

He was shocked to realise that barely a day now passed without him jacking off to the thought of her. And, to his shame, he now started to enjoy doing so in the morning – in the deliberate knowledge that he might soon afterwards be sitting beside her, alone in her car, without her having any clue to what he had been up to half an hour or so earlier. On the occasions when this happened, the perversity of it all made him feel embarrassed and guilty in her company.

However, it also excited him to have such a sordid secret from her, and to join in small talk as if butter wouldn’t melt in his mouth. So did the slight strain of trying to act casual and normal when his testosterone was filling his mind with other things than the weather or the proposal to build a new housing development nearby, and its likely impact on the traffic. He found himself taking increasing notice of her voice. It helped him to imagine her speaking lewdly when he was self-pleasuring.

Although he was nineteen years old, he was still a virgin. He’d had a casual girlfriend for a few weeks the previous year, but the nearest they had come to sex was mutual pleasuring. He’d fingered her a couple of times to climax while she’d jerked him of in her hand.

He thought of some of his friends and of their likely reaction if they knew. He thought of their derisory laughter and the names they would call him. But it didn’t curtail his fixation. Rather, it fed it. It was probably the knowledge that he was fantasising about something that his parents, his friends, everyone who knew him – and her, too – would disapprove of and would find either scandalous or sad.

And today Brenda was wearing his favourite skirt. It was white with a large check pattern in lilac. It almost reached her knees and was slightly flared. Below its hem her thighs and legs looked very appealing. On the outward journey, he sat in the back with his grandmother so that his grandfather could sit in the front (he had slight mobility problems, and it was easier to swing himself into the front seat than the back).


At last they reached his grandparents’ house. He and Brenda went in for the obligatory cup of tea. He fed his hungry gaze again and again, though furtively, on the object of his desire. An idea had come to him, and he tried to dismiss it, but with increasing difficulty. Again and again the thought resisted his silent objections. “Why not? Why THE HELL not?” And although he could think instantly of plenty of reasons not to, his desire for her threw a counter-objection against each. It was ridiculous, but he found himself debating whether she might even welcome his advances, or, even if she rebuffed them, whether she might at least be flattered enough not to tell his parents.

And although, of course, he could think instantly of plenty of reasons “why not”, his latent and rising desire for her threw up a counter-objection against each. It was ridiculous, but he found himself debating whether she might even welcome his advances, or, even if she rebuffed them, whether she might at least be willing not to tell his parents.

After all, he thought (as he had wondered many times previously), she had been single and not even in a relationship as long as he could remember. She was dedicated to her work as a carer of disabled children. Might it be – his heart skipped afresh at the thought, however unlikely – that this was in part a substitute, a way of coping with having no man in her life?

He had sometimes even wondered if she had ever had sex, or whether, like him, she was still a virgin. If so, he wondered if she was curious what it would be like to have sex. It seemed odd to think that maybe she was a virgin, like he was, and to think about them having sex together on a voyage of discovery for them both. Or, if she wasn’t a virgin (which seemed likelier) – did she miss sex? Did she miss being kissed, fondled, aroused – even entered? These thoughts had crossed his mind many times recently, but now they seemed to flood it and almost to sweep away everything else before them.

Was it even possible, however unlikely – that she missed these things enough to welcome his inexperienced advances or, if not to welcome them, to allow them, or if not, at least not to fulfil his greatest fear – informing his parents of their son’s perversity?

Such were the thoughts racing through his mind as he sat in the incongruous and innocent setting of drinking tea with her and his grandparents. At one point Brenda crossed her leg, and her skirt rode high up her thigh. He tried unsuccessfully not to look. To his horror he realised he was developing a hard-on. He forced himself to look away, but couldn’t resist glancing back again. Although she gave no sign of spotting his furtive but hungry glances, after a few minutes – despite him silently willing her not to – she tugged her skirt hem closer to her knee.

His glance now alternated between her thighs and her breasts. Despite the confines of her bra they rose and fell deliciously under her pale blue polo shirt. He ran his gaze over the half-discernible panels and straps of her bra under the cotton, and once more at her legs and fleshy thighs.

His grandparents’ presence made it all the more naughty, yet all the more arousing, too. So did the need, conscious of the burgeoning of his erection, to make himself think about other things, anything other than Brenda and the impending journey home alone with her. To his relief, his erection abated a little, at least hopefully enough for Brenda and for his grandparents not to notice.

At last, the half-dreaded, half longed-for moment arrived to depart, not his customary fifteen minutes’ or so duration alone with her, but one that would take nearly an hour and a half. Desire and dread rose as he anticipated it, and as he returned to his inner debate.

For his mind was now in overdrive. It was far from made up, but as well as “Should I or shouldn’t I?” he had begun to ask himself, though tentatively, “And if I were to – what would be the best way to make a move on her?”

He silently cursed his inexperience. Other dreads loomed in his thoughts and became a spectre almost as great as his parents discovering that he had made advances on their friend. It was the fear of making an idiot of himself, of having Brenda herself might at him. Still worse, she might be hurt and shaken, and, as a long-standing family friend, he genuinely didn’t want to alienate her. His crazy notions were driven into retreat. For now.

As he got into the car his heart was beating quickly. He glanced furtively down at her lap. Her check skirt had ridden high up her plump thighs, which looked very alluring. She started the car engine and, waving back to his grandparents, pulled out of the drive and drove off along the road. He glanced admiringly at her modest butnicely formed breasts under her polo shirt. He looked down again, at the high hem of her skirt. He felt a flush of embarrassment and excitement at being alone with her. It was not the first time that he had been given a lift in her car, of course, but he had never spent an hour on his own with her. It felt deliciously intimate.

“Your grandparents were very appreciative of being given a lift home.”

“Yes, it was very kind of you to offer, Brenda.”

She smiled. He thought she caught his gaze on her thigh. He made himself look away.

“That’s fine. It was good of your mum to suggest that you come along for the ride – to keep me company on the ride back.”

She made small talk but all the time he was highly aroused, torn between looking at her fleetingly and forcing himself not to. He joined in, glancing furtively at that retreated skirt hem and the fleshy thighs below it. When she pressed on one or other of the car pedals his eye was drawn to the way the muscle of her leg or thigh tensed. His arousal was heightened by shame, by fear of being spotted, and by her being twice his age.

Part of him wanted the journey to end; part of him wanted it to last for hours. All the time he was painfully conscious that the legs and breasts he had wanted to touch for a long time were just inches from his hand.

He had been in this situation many times before and had toyed fleetingly with the idea of making a move. Fear had always held him back, fear of offending her and of whether she would tell his mother. Today, though, on the outward journey, the idea had grown, and he was already half-decided, despite his nervousness. It was just a question of plucking up the courage and doing it.

“Are you all right, Stephen?”

“Yes. Yes, why?”

“You just seem… I don’t know, distracted…”

“No, sorry.”

“If something’s on your mind I’d be happy to listen.”

His nerves were almost at screaming point, but he decided to risk all.

“Well, Brenda… I’ve been… er… wanting to do this…”

He placed his trembling hand just above her knee & stroked her thigh. She gave a low intake of breath and laughed nervously.

“I see.”

She pushed his hand away. For a few agonising moments, he fought with himself as he tried to decide what to do next. After all she had pushed his hand away. But then again, she had not gone crazy at him, or even sounded offended or shocked.

“Sorry, Brenda. But you wanted to know what I was thinking. I was… being driven crazy by the fact that your legs are just inches from my hands…”

He placed his finger on her warm thigh again and caressed her plumpness, thrilling in the soft smooth skin. She thrust his hand from her.

“No, Stephen. That’s enough. You mustn’t… you shouldn’t even be thinking like that…!”

“I know you’re a lot older than me, Brenda, but I can’t help it…”

She felt herself flush with shock, and with fear. She was alone with him, and his forthrightness and sudden change in his behaviour alarmed her. She saw his eyes rest on her thighs again.

“You CAN help it. And you MUST. I… I’m flattered that you find me attractive. But… but that’s enough now. I MEAN it…”

She knew that her voice tremored slightly, and hoped that he didn’t mistake it for excitement. He was torn for a few moments, but he knew that if he delayed any further now it would be hard to make a further move.

“Okay, Brenda. Sorry if I shocked you. But you asked me to share what was on my mind. I told you.”

He placed his hand just below the hem of her skirt now, and stroked her inner thigh. She grabbed his hand and pushed it away from her. She glared at him.

“Keep your damn hands off me, Stephen. I mean it! YOU might think it’s funny but I damn well don’t!”

She was shouting now, and her words were racing from her. He glanced at her face; it was flushed and her small eyes flashed. He wanted the ground to swallow him up. He silently cursed his stupidity and wished he could turn back the clock five minutes.

“Twice you’ve touched me, and twice times I’ve pushed your hand away and told you to stop, but you grope me again. Which… which bloody part of ‘NO’ don’t you understand? In fact…”

To his horror, she slowed the car down and pulled in.

“In fact, you can damn well make your own way home from here. There’s a bus stop just ahead. And touch me one more time EVER again and I’ll tell your parents! I… I’m disappointed and shocked, Stephen. I’d always thought what a nice young lad you were. And all the time… you’ve been thinking about me like… THAT! And thinking I might even welcome your touching me!”

He felt himself flush with embarrassment and shame.

“I… I’m sorry, Brenda. I…”

“Get out of my damn car, Stephen… I mean it!”

“Okay. Okay. I’ve said I’m sorry. But…”

“Never mind ‘but’. Get… get the hell out!”

He swung the car door open.

“Okay. Sorry if I misunderstood. But… I didn’t THINK it was funny. I was quite serious about finding you sexy, Brenda. Very serious in fact… b-but I’m really sorry…”

He almost stumbled out of the car. He couldn’t bear to look back and headed slowly towards the bus stop with his head down. He had no idea when the next bus was due, and knew as well that the journey would take far longer than by car.

He wondered whether Brenda would tell his parents. Even if she didn’t, he felt ashamed of himself for upsetting her. Sure, she was one of his abiding sexual fantasies, but she was, after all, a friend of his parents. She was a genuinely nice woman, too. He wondered how he could ever look her in the face again.

He expected to see her car pass him, but the minutes passed and there was no sign of her. He imagined her in tears, confused, angry, and upset. He felt terrible.

Another thought crowded in on him. If he was late back, what should he tell his parents? Even if Brenda didn’t tell them, his story may not be corroborated by hers if they were to speak to her!


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