Tim’s First Time


The story of Tim’s first time is my first story. Many thanks to lindseymarsh who edited and polished this story.


It was just after eight o’clock on a warm, Sunday morning in early June and Tim and Jennie were spending the weekend at Jennie’s mother’s house. They usually didn’t stay overnight, but the previous evening all the family had gone to the annual ball at the local Golf Club and they had chosen to stay. Jennie had arisen first, leaving Tim asleep, his body still trying to assimilate the six or seven pints of beer he’d consumed the previous evening. After going to the bathroom, she had gone into her mother’s room to say good morning. Her step-father was already up and pottering around in the kitchen with her half-brother.

“Why is Gerald up so early?” she asked her mother.

“Why do you think? Richard and he are going to play golf. Sometimes I think he prefers golf to me.”

It was a refrain Jennie had heard before and had dismissed, but this time it was said with some degree of venom.

“Mum; boys will be boys. I’m sure he doesn’t worry about his swing when he’s in bed! Is he a good putter?”

“I wouldn’t be so sure and as to his putting…..”

It was meant as a joke, but her mother’s answer contained no hint she had taken it as a joke and Jennie didn’t want to be drawn into, what was likely to prove, a heavy conversation. Excusing herself, she returned to her room to find Tim in bed and apparently still asleep. As she leant down to get into bed, she heard the front door close and the crunch of feet on the gravel. She knew it was her step-father and half-brother, but, curious, went to the window and looked out. As there was a small table in front of the window and her step-father’s car was parked next to the house, it was difficult for her to see what was happening without leaning over the table and as she did her cotton nightdress, shortened by too many washes in hot water, ran up her legs giving, the now awake, Tim an unrestricted view of all her charms.

It was an opportunity he couldn’t resist and he slid quickly out of bed, moved over to where she was standing, wrapped his arms around her body, slipped his hands under the nightshirt and fondled her tits. He loved her tits, they weren’t big, just a good handful, but after twenty-four years of marriage, they were still reasonably pert with pink, pencil-eraser nipples and large, almost circular, areolas. She stood up and pushed back against him, wriggling her bum against his cock.

“Mmm, I guess you’re pleased to see me — or is it just morning wood?”

He laughed and replied, “Pleased to see you of course, my love.”

She jabbed her elbow into his ribs and turned to face him.

“You’d better be.”

He laughed again and was surprised when she put her hands on his chest and pushed him down onto the bed. With a gleam in her eye, she jumped on the bed and straddled him; her legs either side of his thighs, her cunt resting against his cock. It felt good and she started to rub her clit against him, sliding her cunt slowly and sensually, backwards and forwards. He watched; he knew what she was going do as she’d done it many times before and usually when she was feeling horny.

“Fancy it, do you?”

She nodded and took her nightshirt off, exposing her hard-nippled breasts. She cupped them in the palms of her hands, lifted them, bounced them up and down once or twice and flaunted them at him. He felt compelled to comment.

“Not bad.”

“I hope you weren’t going to add; ‘for a forty-four year old’.”

“I wouldn’t dream of it.”

She smiled at him and started once more to move against him. It didn’t take long for her to cum; and when she did, it was clear she was more excited than normal. She ground against his cock, her breath coming in gasps and when she came, in her usual manner invoking every Anglo-Saxon term she knew and imploring him to abuse her and her body.

When she had finished; she stayed mounted, playing with her tits, rubbing her cunt against him, coating his cock with her juices and trying, with little success, to entice him with her interpretation of a vamp. When she’d teased him enough, she dismounted, lay beside him, kissed him and reached for his cock.

“It’s your turn. Do you want me to blow or wank you – or both?’

It was an inviting offer, but after her performance, all he wanted was to fuck her.

“Neither, I’m going to fuck you — although you can start with a blow job.”

“Greedy bugger. My mouth not enough for you?”

“Shut up. Get on your knees and stick your bum in the air. It’s doggy fashion for you, young lady.”

The banter was good natured; humour with a strong sexual motif. She looked at him closely; she could see he was more excited than usual and she knew when that happened, she was in for a no-holds-barred fuck. Without waiting for further instructions she got onto her knees, stuck her bum as high as she could in the air, wiggled it seductively and waited for him, wondering istanbulescort.biz what he would do.

He got behind her, on his heels rather than his knees, took his cock in his right hand and pushed it gently against her other hole. She gasped, she wasn’t expecting anal sex, but if he wanted it, she was ready.

“Oops, missed.”

He laughed again and adjusted his cock so that it was rubbing against the lips of her cunt and laughed when she pushed against him; inviting him in. He rubbed the head of his cock against her cunt once more; he wanted to drive it into her, but he also wanted to tease her.

“Tim, if you don’t stick your cock into my cunt, you’re not getting any.”

“OK, but I need to get a condom.”

“Tim. I’m forty-four, I keep getting hot flashes and haven’t had a period for four months. Don’t bother.”

He laughed and without pausing thrust forward, slipping his cock between the lips of her wet cunt and surprising her. She gasped and pushed against him. She loved his cock in her cunt, loved the way he made love and in particular she loved the attention he gave to her needs. Fifteen years ago, when Tim had been working away from home for long spells, she’d taken a lover, but it hadn’t taken long for her to realise occasional sex with Tim was far more enjoyable than more frequent sex with her lover.

She had been expecting being fucked hard and she wasn’t disappointed. Tim drove into her, his cock driving to the bottom of her cunt; so deep she thought he would drive into her womb. She responded to his thrusts, she was as excited as him, she wanted to cum and she wanted to feel his cum flooding her cunt. It had been a long time since she’d been on the pill and since that time she’d not felt his cum leaking out of her cunt and for some, inexplicable reason she wanted to feel it again.

They came together; he’d been ready for some time but waited until he could tell by the sound of her breathing, the way she was responding to his thrusts and her unladylike urgings she was ready.

“Fuck me Tim. Fill me. Fill my cunt. Cum in me.”

It wasn’t literate, but described succinctly her needs. He obliged; his cum spurting inside her, bathing the inside of her cunt and spraying the entrance of her womb while she pushed against him, straining her cunt muscles in an attempt to milk his cock.

When they had finished, they lay together, kissing and enjoying a post-coital feeling of mild euphoria. For Jennie there was an added feeling of post-coital tryst occasioned by the sensation of his cum slipping languorously from her cunt and down her thighs. She had waited almost ten years for him to plant his cum inside her and she was happy; which was why she couldn’t understand why she felt like crying. She kissed him again; she loved him and was re-assured by her belief he loved her. For five minutes they lay unmoving, their breathing gradually returning to normal, his still slick cock gradually wilting. It was Jennie who broke the silence.

“I know this might sound an odd question, but you’re good in bed. I’d like to claim all the credit for teaching you, but you were good from the start. Where did you learn to fuck?”

The question was unexpected; in the twenty-four years since they had married, during which they’d had two children and enjoyed a good sex-life, she had never enquired about his prior sexual experience. Still, he couldn’t imagine her being jealous, but her comment on his performance in bed, had planted a seed of doubt about her fidelity in his mind.

“I was taught by an expert.”

If her question had been unexpected so was his response and based on what she knew about his girlfriends before they had married, an answer Jennie had not anticipated. She had always thought he’d had some prior experience, he’d certainly shown little sign of nerves when he had taken her virginity on the bed in her parent’s caravan in Skegness on a wet Sunday afternoon over twenty-six years ago, but had always assumed his prowess in bed came naturally; an adjunct to his prowess at sports.

“Tell me more!”

“Er, O.K. I’m not the type to kiss and tell, but as it’s you who’s asking and it isn’t likely to be broadcast to the world, I’ll tell you.

“Well I’ve always wondered, but I never dared ask. How did you start?”

“It’s quite a story and it took place on the weekend of my eighteenth birthday. You remember mum and dad lived in Shilton and I went to school there until the end of the fifth form?”

“Yes, that was where my grandmother lived when I was small. Mum and I lived with her for a couple of years just after my dad left us and just before she married Gerald. It was the time when mum had no money.”

“Well, by the time I was eighteen, we had moved to Newbold and I was playing for the local rugby team there. We were playing the Shilton College Old Boys’ XV that weekend and as you might expect, I knew a lot of the Shilton squad because I’d been to school with them. On the Friday before the istanbul escort game there was an evening match between the Tigers and a South African side and most of players on both teams took the bus to Leicester for the game. On the bus my mate, Harry, told me that after the game both teams were going back to the Admiral in Shilton for a swift drink and food, but as we were playing each other the next afternoon, it wouldn’t be a long night. What he failed to add was the lads had a joint presentation for me to celebrate my birthday and to recognise my being the top scorer for the season.”

“I know the Admiral; it’s not far from where mum and I lived with granny.”

“Yes, well,” Tim continued, “we got back to the Admiral at about ten o’clock, had a couple of pies and two or three pints of beer. Just before closing the lads gathered round, sang ‘Happy Birthday’ and called to Joe, the landlord, to ask if the present was ready.

“You might remember, at that time, the Admiral was having bedrooms built upstairs at the back so they could do bed and breakfast? ” He waited until she nodded. “Well, Joe took me behind the bar, pointed me up the stairs to the new bedrooms and told me, ‘Your present’s up there.’ As I was going up the stairs one of the lads shouted, ‘Try it for size and tell us about it tomorrow’.

“When I got upstairs, I went down the still unfinished corridor until I got to the only room with a door, opened it and went in. The room was dim, but sitting on a chair next to the bed and reading a magazine was an attractive woman wearing a black cocktail dress and a matching short jacket which was draped around her shoulders. She was slim, her makeup was perfect and her blond hair immaculate; cut in the feathered, big hair style popular in the late seventies and early eighties. Although, at first glance, she looked quite young, when I looked more closely, I could see she was about ten to fifteen years older than me, perhaps in her mid-thirties, but definitely younger than my mother. When she saw me, she stood up, looked at me, lifted the jacket off her shoulders and put it over the back of the chair, smiled and wished me a happy birthday.

“I’d had no idea what was waiting in the room, but must admit I was not unhappy with my present. Apparently Harry had been the prime mover behind the choice of present and had approached the woman — she told me later her name was Felicity – through someone who knew her.”

He’d never been with a woman before and he hadn’t been expecting a whore for his present, but he wasn’t about to look a gift horse in the mouth, especially if the gift it was bearing was as attractive as Felicity. He knew she was a whore, but looking at her, he found it difficult to believe someone as attractive and well groomed as her could really be a practitioner of the oldest profession. For a moment they had stood looking at each other and then she had smiled once again, moved over and kissed him on the cheek and told him what he was getting for his birthday.

“Tim, I’ve been told it’s your eighteenth birthday and due to the good graces of your friends I’m going to be your birthday present. I’m going to be your lover for the night, a paid lover I know, but I expect you to treat me as a lover and that means with respect and care.”

Tim sank back onto the pillows and looked at Jennie.

“Go on,” she encouraged him, “tell me more.”

“She was good. I was naïve when it came to sex and that night — and into the morning I might add – she taught me everything about making love even how to kiss a woman and how to take off her clothes.”

“Sounds really interesting — carry on.”

“Do you want the blow-by-blow or the potted version?’

“The blow–by-blow.”

For the next ten minutes he described how Felicity had introduced him to sex, including the art of foreplay. It had started innocently enough; she had showed him how to kiss properly, but as he’d done it before she hadn’t really taught him much. When, however, it came to a lesson on the art of removing a woman’s clothing, something he’d never attempted, he’d listened intently to her instructions. The dress zip had been easy; when instructed to do so, he’d run it down her back in record time and then watched as she’d shrugged her shoulders and let it fall to the floor. She was orchestrating everything and he was only too pleased to follow her instructions.

Her next instructions sounded simple, but a combination of nerves and four pints of beer were enough to cause him confusion. Her instructions were explicit; he was told to put a finger of his left hand under the strap and lift it; take the side with the hooks on in his right hand, slide the hooks to his left and out of the eyes and remove the bra, but when he came to perform, he was all fingers and thumbs. Finding the hooks was easy enough, but unhooking them was a test of a dexterity he didn’t seem to possess. He pushed and pulled for what seemed like five minutes, becoming increasingly embarrassed as he continued to fail and when he somehow managed to separate the two sides, it was a welcome relief.

While he was fumbling, she had said nothing and when she spoke again, merely continued with her instructions, telling him to lift the straps off her shoulders and let them fall onto her arms. Later he found it difficult to describe how intently he’d watched as the silky red fabric slipped down her arms to reveal her tits. They were magnificent — not a match for his wife of course, but pretty outstanding.

“And just how outstanding?” Jennie smiled at her double entendre.

“Well her nipples were pretty outstanding, a similar colour to yours and really long.”

“Nicer than mine?”

He looked at her; if he was going to be quizzed like this every time he described Felicity; he’d better be a little less enthusiastic.

“No; but quite good.”

It was a lie; they were much longer and sexier than Jennie’s, but he knew if he even hinted they were superior to hers, he was in for trouble.

“So what happened next?”

“I took her knickers off. They were red silk and matched her bra, but, thank God, were much easier to remove. He paused for a second as he recalled the moment her had first seen a woman almost completely naked. She’d been a vision, standing there in her red suspender belt, black, seamed stockings, four inch, red high heels and, incongruously, a single-strand pearl necklace. She’d posed for a moment, almost model-like, with her hands on her hips and her hips thrust forward slightly as if to emphasise her cunt. She’d had almost blond pubic hair, almost the same colour as Jennie’s. She’d let him look for a few moments — drool was probably a more accurate description – and then held her hands up with her palms facing away from him, giving him the opportunity to notice her lipstick colour, pink, almost matched the colour of her nail varnish and was a similar colour to her nipples and areolas.


Jennie’s voice interrupted his reverie and he returned to his narrative, although providing her with a more prosaic description of the unveiling. He ended with a description of her tits.

“They were perfect.”

It was the wrong word.

“And mine aren’t?”

“I didn’t say that. In fact they were so similar to yours, she might have been your sister.”

“Older or younger?”

“Why, older of course.”

She smiled and added, “Go on.”

“She asked me if I liked what saw and when I nodded, she started to remove my clothes. It was abundantly clear, from the way she removed them, she’d done it many times before and by the time she pulled my trousers down my cock was as hard as it had ever been; so much so she had to wrestle my underwear past it. Once I was naked, she looked at me and said something to the effect, ‘My, aren’t we a big boy.’ I suppose she said the same to all her men, but it made me feel good. What she did next made me feel even better.”

“And just what was that?”

“She blew me. Without saying a word, she got hold of my cock, pulled back my foreskin and started to play with it. I can’t describe everything she did, but suffice it to say it took only a minute at the most before I was pumping my spunk into her mouth and then watching her swallow it without batting an eye.”

“Was that a dig at me?”

“No, not at all.”

Another lie. Jennie was a good blow job artiste, but for some reason, wouldn’t swallow his cum. She would hold it in her mouth, show him, even stick out a cum-laden tongue, but would never swallow it.

“Go on.”

“OK — and then what happened?”

“You can have one guess — after all, she was a whore.”

“You fucked her.”

“I did.”

“Was it good?”

Another question with only a hiding-to-nothing answer and so he ignored it and continued with his narrative.

“We got into bed. Well we got into bed after she told me she would only remove the rest of her clothes if we got into bed. By the time we’d got into bed my cock was starting to get hard again.”

“Hmmm, I guess the performance has dropped off since then.”

“Stop taking the mickey. Wait until I’ve finished this story and I’ll show you performance.”

“Promises, promises.”

“I think she only had to wank me twice and it was hard. I tried to mount her, but she was having none of it. She might have been a whore, but it was clear she wanted to participate fully in the action. I’d never given head to a girl, the most I’d ever done was finger-fuck, and not very expertly, my sister’s best friend and I’d no idea how to play with a woman’s cunt. By the time she’d finished with me, I’d been given the Cook’s tour of her private parts, had sucked and licked her to her climax and had my face coated in her cum.

“What was her cunt like?”

Another odd question, but he ought to answer. He thought for a moment; if he compared it to cunts in general it might give her the idea he’d had experience of cunts other than hers; his answer had to be specific.

“Well; actually, it was similar to yours. Her clit was about the same size, her labia were similar and when I managed, with her help, to find her G-spot, she turned on almost as quickly as you.”

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