Bye Bye Virginity

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

'That's better.' She told him, pushing her bikini bottoms down her legs and stepping neatly out of them. 'You're very well equipped, aren't you?'

He didn't think so, but he wasn't going to argue. He nodded silently, his eyes now roaming over her naked, and very beautiful, body, fastening finally on her closely trimmed pubes with the hint of her labia showing from between her legs. He groaned to himself and looked away, he wasn't supposed to be looking at any woman like that, let alone one twice his age.

'You can look, I'm not shy.' She'd told him before but his natural shyness rebelled against it. He forced himself to look her over again, wanting to feast his eyes, but still not really at ease with it yet.

She smiled and climbed back onto the bed, putting one leg over his to straddle him, and giving him a wonderful first sight of her pussy in the process.

'Ready?'

For a moment he wondered what for, but then he understood and he nodded eagerly. His moment had come at last. He nodded once more.

'Stay still.' She demanded.

Any other time and he would have burst out with nervous laughter at that. He was too tense, too apprehensive to move a muscle anyway. He lay there looking down as she positioned herself over him and then reached down for his cock, guiding it towards her. The moment his tip touched her thigh he let out his pent up breath in a whoosh, making her glance up at him.

'All right?' She asked, worried.

He gave his usual nod, unable to explain that he had been holding his breath in anticipation ever since her leg had straddled him.

She smiled again. 'Here we go then.'

She moved around slightly, adjusting her position more accurately above him so that she could guide him into her, and then lowered herself slowly and gently down onto him. He felt her pussy slowly engulf him as she slid onto him, his cock going deeper and deeper into her until finally she was sitting on him. He gazed up at her in wonder, seeing the look of concentration in her eyes and the smile of pleasure on her lips while he enjoyed the sensation of being inside a woman at last. She stayed there like that for a few seconds, smiling down at him, and then began riding him, lifting herself up and down on his cock.

He had been told how women became wet, but he had never realised just how nice such warm slippery wetness could be. God, it was wonderful, just to feel her lovely velvety tunnel sliding over him, enveloping him, a sleeve to keep his erection warm and safe. If that was sex, he wanted more, and more, and more. One thing was for sure, he didn't have to worry about being a virgin any longer, because he no longer belonged in that unhappy club.

Lori looked down at him. 'You're smiling.' She told him, smiling back as she rose and fell on his cock. 'That's good. Now enjoy it, I am.'

For a couple of minutes she carried on riding him like that, but then she changed her position, leaning forward to rest on her hands placed either side of his head, letting her breasts swing straight in front of him. He wasn't sure he was allowed, but he couldn't resist, his hands came up as if of their own accord and cupped her breasts. He felt the lovely soft weight in his hands and the firm feel of her nipples on his palms. He squeezed gently, cautiously, experimenting in his own uncertain way while she impaled herself on his cock. It felt wonderful and he hoped that it felt as good for her.

He looked u at her face, seeking some sign of her enjoyment and happy to see her smiling warmly down at him. But then, suddenly, her expression changed, her eyes closed and she began to make little noises. It worried him, he wasn't sure what was happening, but Lori's face said that she was very obviously happy and so he relaxed and let her carry on, squeezing her breasts a little more firmly, a little more confidently.

'Yes.' She hissed, her eyes popping open and a smile of pure delight spreading across her face. 'I'm going to come.'

He knew women orgasmed, but he'd never been quite sure what it entailed, perhaps that explained the little gasping noises she was making. Whatever it was, he knew he was about to find out. He felt abruptly proud, proud that he was able to give pleasure to a woman, and a mature, experienced woman at that. Not that he'd done very much himself towards her pleasure he acknowledged ruefully to himself.

She was moving more quickly now, lifting herself until just the tip of his cock remained inside her and then slamming herself down onto him, gasping and moaning her pleasure. He lay still, scared to move in case he interrupted her rhythm, even though his hips were yearning to move and thrust his cock hard up to meet her downward motion. And then, right at the back of his mind, came the knowledge that he could come again too. He grinned, ecstatic that he might actually come inside a woman's vagina, and ecstatic that he was doing this at all.

But it didn't work out like that. Lori suddenly rammed herself down on him, groaning loudly as she ground her pussy against him with his cock all the way up inside her, and then collapsed on top of him, gasping and shaking, and giggling stupidly. He gazed up at her, vaguely aware that she had climaxed and alarmed at her reaction.

'God, that was wonderful.' She told him breathlessly after a minute or so, lifting herself onto her arms again.

He lay there silent and hazily disappointed, thinking that there should have been more to it. There had been no fireworks display, no thrashing about and no shouting dirty words like 'give it to me big boy' or even the long series of 'yes, yes, yes,' that he'd expected. Perhaps he'd been watching too much porn; perhaps real life was more restrained. But his biggest disappointment was that he hadn't come and deep inside he knew he couldn't say he'd had sex properly until he'd shot his load into a willing pussy.

She peered down at him, sudden realisation of his continuing erection and his frustration registering on her face. 'You didn't come, did you?'

He shook his head.

She smiled suddenly. 'Good, then we can keep going.'

He looked up happily at her and lat waiting for her to start moving again.

'But I'm not going to do all the work.' She chuckled, stretching out her legs to lie directly on top of him. Then, with his cock still inside her,, she wrapped her arms tightly around him and rolled, pulling him over with her until the positions were reversed and he lay on top of her. He looked down in astonishment at her smiling face, amazed that such a manoeuvre was possible. She spread her legs beneath him, pulling them back until she could wrap them around him, opening herself up to him.

'Now you do it.' She demanded.

He looked down at her, excited but anxious, knowing that this was it, he actually was about to fuck a woman properly. He savoured the thought 'I'm going to fuck a grown up woman' before he pushed himself home, his cock spearing deep into her.

Lori moaned quietly as he did so, her arms around him, pulling him close. 'Oh yes, that's fabulous.'

He began thrusting, slowly at first but picking up speed as he gained in confidence. His imminent climax had receded, but he knew that it would soon be back and that his dream of climaxing inside a woman would be granted. Very soon he was hammering into her as hard as he could, not quite out of control, but close to it, especially as she gasped words of encouragement into his ear and told him how much she was enjoying it.

Soon, instead of words, she was uttering the same little noises that she had made before, grunting and gasping into his ear, her nails digging into his shoulders. For a moment he thought she was teasing, he had no idea that a woman could come more than once, but then he realised that she wasn't pretending and they could.

He wondered who would come first; he knew he wasn't far away. He was plunging himself into her tunnel, feeling the warm moist walls surrounding his cock and bringing him closer. The same sensations were creeping up on him, starting at the base of his cock and spreading out all the way through him, becoming more intense as he got closer, almost making it impossible for him to thrust. He was nearly there, so nearly, and then, suddenly he felt her nails bite more fiercely into his shoulders and heard her groan into his ear. They were about to climax together. He couldn't quite prevent the grin that spread across his face at the thought, even though he was breathless from his exertions. He never thought it could happen, but it was.

They came absolutely simultaneously, bucking and squirming together as he emptied himself into her, spurt after spurt, and she held him tight, making sure she received everything he had to offer. Lost in his own little world of sensations and triumph he only vaguely registered her cries and movements as he came. He never believed it would feel so good, so overwhelming, to climax with a woman, especially knowing, even if only dimly, that he was giving her pleasure too. When it was over he slumped on top of her, panting and trembling, his mouth open and his eyes closed as he tried to hang on to the sensations, the new sensations of proper full sex with a woman. He felt her legs fall onto the bed and her hand under his shoulders easing him up as she too struggled to get her breath back.

He lay on top of her for a few moments, his chest heaving and his legs like jelly but feeling as pleased and proud as could be. He had done it; he'd got rid of his virginity and all its labels. He was now a man. Then he yielded to her gentle but insistent pressure and rolled to one side, his shrinking cock slipping from her and trailing wetly over her thigh as he moved away.

But then reality hit him and he was suddenly apprehensive. He'd just had sex with a neighbour, a mature woman, someone old enough and experienced enough to be his mother. Would she be angry with him, would she tell his parents? More importantly, was his performance good enough, did he satisfy her as she had certainly satisfied him. He turned on his side and gazed into her face, searching for reassurance. He needn't have worried.

'You know?' She said breathlessly, smiling back at him. 'I find it hard to believe that was your first time. You're pretty damn good.' She shrugged. 'Okay, so your technique needs a little refining and you seem to never have heard of foreplay, but we can work on that next time.'

For a moment her meaning passed him by. He was too wound up in what she had pronounced as his faults, even though she seemed to have conveniently ignored the fact that she had given him no chance at any foreplay. But then it struck him. She had said 'next time'. She meant for them to do it at least once more and, he let himself believe, more than once, many more.

'Next time?' He asked hesitantly.

'Oh yes.' She grinned, a tiny giggle escaping her lips. 'The same time tomorrow would be good. But after Millie gets back we'll have to change it to Fridays when she has basketball practise. Is that okay?'

'Yes.' He croaked, nodding enthusiastically, his object of desire suddenly changing from daughter to mother. To hell with Millie, why have a novice when you can have an expert?


12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
9 Comments
OseekerOseeker11 months ago

I'm sure that even though it was his first fuck that he didn't need very much instruction...

Lucky lad having an older gal enthusiastically wanting to fuck him....and then....again soon!

4 Stars

AnonymousAnonymousalmost 3 years ago

Good short story!

DebPlays09DebPlays09about 4 years ago
Wickedly hot!

Love your stories. Keep them (and us) cumming!

SWT3SWT3about 4 years ago
How I lost my virginity

Thank you. This story took me back to the loss of my own virginity, both originally and as a fantasy right now.

I was hitchhiking from Richmond Virginia where I had been visiting my virgin girlfriend. I got picked up by a woman, maybe 5 years older than me just outside Washington DC. She took me to Blues Alley, a blues/jazz bar in DC. There we enjoyed the music and had a beer or two. It was my first time in a bar; I was about 18 at the time. Then, she took me to her apartment. There we began the sex dance. I am sure there was some kissing and petting which I don't remember. What I do remember so clearly is staring into her pussy and following her instructions on how to lick and love it. It was clear that was the gateway to our fucking which we did shortly thereafter. And then I was on my way again. We met one time after that when my same girlfriend was pregnant and we needed an abortion. All of this was in 1965, at the beginning of the great sexual awakening which for me continues today.

As I read this story, I came to appreciate that I am something of a virgin again. After that experience, I went on to have many intimate relationships, three of which progressed to marriage. The last marriage lasted for almost 19 years. One night we fought for about 5 minutes and then our marriage was over. That was almost 10 years ago. Since then, I have not had an intimate relationship and have only even been with a woman a few times. Hence, it was easy to fall into the fantasy of losing my virginity as I read your story and a very sweet fantasy it is too.

By the way, during the past 10 years, I have not been celibate. I have investigated porn with its lessons for technique, Tantra with its offer of connection to pleasure and ecstasy, some group sex and lots of gay sex.

Namaste

Wes

AnonymousAnonymousabout 4 years ago
Excellent.

You had a wonderful build-up, especially with the description of his nervousness. Having her take charge was perfect to move the story along.

Show More
Share this Story

Similar Stories

My Girlfriend's Neglected Mother Hot Mom, hot daughter, is anyone complaining?in Erotic Couplings
That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
After School Special Todd's mistake gets surprising results from Miss Ross.in Mature
Party with the Neighbor MILFs A teen joins his four mature women neighbors.in Mature
Ms. Jackson Ch. 01 Boy is torn between his longtime girlfriend and her sexy mom.in Mature
More Stories