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This is the next story in my admittedly slowly-developing quest to write at least one story in every Literotica category. All the characters are aged over 18 and all are fictional. Although the story is completely made up, this one just seemed to work best as a first person narrative. I hope you enjoy it and I hope you will vote and comment either publicly or via email.


“You want me to WHAT??!!” I spluttered into the froth on my coffee.

On the other side of the table Kelly grinned at my flustered reaction to her request.

“You heard me,” she replied calmly. “I want you to take my virginity.”

I simply stared at her — hearing, but still not really believing, what she’d said. My coffee cup was poised mid-air and she reached across to press my hand and the cup back down to the saucer.

She tilted her head and smiled at my stunned face. “Hello!” she teased. “Is the prospect of taking my virginity so revolting to you that you can’t even respond?”

I snapped out of my confusion and smiled back. “No, of course it’s not. You’ve just caught me completely off-guard. When you said you wanted to meet me to ask a favour I thought you just needed some financial help or maybe a job. The last thing that would have occurred to me was … well, what you’ve just asked!”

“Well, I’m sorry if I’ve shocked you Uncle David! But I am serious. I do really want this — although I sort of hoped I wouldn’t have to beg for it.”

“Jesus Kelly, I’m sure you’d never need to beg anyone for that privilege. And for God’s sake call me David — I’m not really your uncle after all and you’re certainly old enough now to use my first name.”

“Okay — David,” she replied. “So what do you say? Yes or no?”

“Holy crap young lady, I’m still trying to get my head around this! But I have to say my first instinct is definitely ‘NO’.” I silenced her protest with a raised hand. “Now hang on. It’s not because I think the idea is revolting — or that I think you’re not, well, you know, desirable or anything. And I’m more flattered than you could possibly know. But it’s just that it seems so inappropriate. For a start I’m more than twice your age — I’ve known you since you were a new-born — your father is my best friend for God’s sake — and, well, I suppose because — I don’t now — it just doesn’t feel right!”

Kelly slumped back in her seat, pouting, looking more like the child I’d known for two decades than the grown woman she’d now become.

“It’s not the response I was hoping for,” she mumbled. I glanced nervously round the café, worried that others might be eavesdropping on our conversation. But the general buzz of the café reassured me.

“Now, look,” I said to her as kindly as I could. “You’ve got to agree you’ve sprung this on me quite suddenly — so you can’t blame me for being surprised. I just think you need to think very seriously about what you’re asking. I doubt you’ve really thought it through.”

She leaned forward and looked hard into my eyes. “But that’s just it,” she insisted. “I HAVE thought it through. I’ve been thinking of nothing else for the past month or so.”

“Okay, okay, I accept that,” I said. “But tell me why.”

“Why I want to lose my virginity or why I want you to do it?”

“Well, both, obviously.”

“Okay but this is going to be a two coffee explanation. Do you have time?”

I glanced at my watch. “Sure, I can give you another half hour before I have to get back to work.”

Kelly signalled a passing waitress and ordered two more coffees — a skim latte for her and a regular one for me. Then she spread her hands on the table and looked down, clearly gathering her thoughts. When she began to speak her tone was calm and reasonable and her thoughts seemed clear and coherent.

“Okay — so — I’m 23 and I’m a virgin — probably the last 23 year old virgin in the world! But it’s not something I’ve striven to achieve — I’m not proud of my virginity but I’m not ashamed of it either. The fact is — it’s just getting in the way of my sex life.”

I raised my eyebrows at this.

“It’s true,” she insisted. “As you probably know I’ve never had a long-term boyfriend. I’m not sure why that is — I’ve certainly dated enough guys but for some reason it just doesn’t last. Maybe I intimidate guys a bit — or they just don’t find me attractive enough to want to screw me … oh don’t look so disapproving, I could have said “fuck”.

I laughed at this. “I’m not disapproving. I’ve just never seen you in this light before.”

“Anyway,” she continued. “The whole virginity thing has gone on for so long that it’s becoming a bigger issue for me than it should be. Every time I date a guy now I’m thinking: is he the one? Do I want him to be the one? Does he deserve to be the one?” Kelly sighed and shrugged. “And the longer it goes on the harder it gets. Like I said, I don’t prize my virginity. It’s not like I’m saving canlı bahis myself for marriage or any of that crap. But it gets awkward even to talk about it. I can’t say anything to my girlfriends without them making a big deal of it, and how does a 23 year old woman tell some random guy: oh by the way — when you fuck me — it’s going to be my first time ok??”

I had to laugh at that and Kelly seemed to appreciate my understanding.

“So the long and short of it is that I’ve decided to take matters into my own hands — wait no, that’s completely the wrong expression here…”

I laughed again.

“… what I mean is: I’m taking control of my sex life. I want to get this whole thing over and done with so I can just get on with being a normal sexual woman. So yes, Uncle… er, David, I have thought it through very carefully.” She reached across the table and took both of my hands in hers. Then she looked me squarely in the eyes and said: “And after very careful consideration – I want it to be you that helps me out. Please.”

Whether it was the touch of her soft hands in my large ones, or the genuinely pleading look in her beautiful brown eyes, I don’t know, but for the first time since this conversation started I felt the tightening of sexual tension in my gut — and I actually visualised a possible coupling between me and this gorgeous young woman. I’d be lying if I said it wasn’t a very appealing thought.

“Wow,” I replied, warmly squeezing her hands. “I guess you really have thought this through. But the other question remains: why me of all people? You must know lots of age-appropriate men you could approach with this amazing offer.”

“Okay,” she said firmly, releasing my hands and taking a long sip of her coffee. “This part’s easy. First of all I want it to be someone I genuinely like and respect — and I’ve always liked and respected you.”

“Okay,” I said cautiously.

“Secondly, it has to be someone I can trust. As a professional sportswoman I’m somewhat in the public eye and I have to be a bit careful about my reputation. There are some general morality clauses in our contracts that have to be considered. I wouldn’t want to pick some arsehole who flashes inappropriate pictures or messages all over the internet.”

“Sure,” I concurred.

“Thirdly — it has to be someone who knows what they’re doing. I know you’ve been single for a while now — but I’m guessing you still date and haven’t forgotten how the basic parts fit together?”

“Yeah, yeah — go on.” I rolled my eyes and lifted my coffee cup to my lips.

“And finally…” she paused here, sat back in her seat and fixed me with a look that was completely inappropriate. “I want it to be someone I’m hot for.”

For the second time I spluttered into my coffee — spreading droplets onto the table and onto my tie. “Oh Jesus — now I know you’re bullshitting. Where are the candid cameras hidden?” I looked around with exaggerated motions while dabbing at my tie and the table with my napkin. Kelly merely smirked at me and leaned across the table to continue in a stage whisper.

“It’s true! I’ve had a teenage crush on you practically since puberty. You’ve always been a good-looking guy!”

“Yeah, yeah — I’m sure. I’m Brad Pitt and Johnny Depp all rolled into one!”

“Oh God,” she protested. “Don’t compare yourself to those douche bags! You’re much nicer — maybe in the class of David Tennant or Alan Rickman.”

I was still entirely sceptical. “Alan Rickman…” I reminded her. “…is dead! And I too have far more years behind me than I have in front of me!”

“Oh, rubbish! Don’t forget I know exactly how old you are because you started kindergarten with my dad.”

“Yes, exactly, and he’s been my best friend ever since. I can’t begin to imagine what he’d think if he was listening to this conversation.”

“Well, yeah, I suppose, but…” and again she reached across the table to grasp my hands and give me that oh so inappropriate look. “…doesn’t that make it even more appealing — you know, just that little bit wicked!”

I knew what she meant and again the thought of a naked Kelly in my bed crowded out any competing thoughts of prudence. Involuntarily my eyes flicked down to her breasts, encased in a completely unsexy tracksuit top, but still bulging invitingly over the edge of the table. She saw my glance and for the first time I saw a slight blush colour her cheeks.

“Come on David,” she pleaded, caressing my palms with her fingertips. “Won’t you do this for me?”

She didn’t know it — but she had totally convinced me, and now I really wanted to have first time sex with my best friend’s youngest daughter. I held her gaze for a long moment trying not to let the growing bulge in my trousers distract me from my thoughts.

“Ok, listen,” I told her. “I’m not saying ‘yes’ — but I’m not saying ‘no’ either. I really am very flattered but I just need a bit of time to think about it: whether I could — or should — go through with this.” I fished out my phone. bahis siteleri “Give me your number, it didn’t come up when you rang me to ask for this meeting.”

“Oh sure,” said Kelly. “Let me text it to you then you can save it in contacts. We have to be very careful with our phone numbers — you wouldn’t believe how some players get either stalked or trolled by loony fans.” She fiddled with her phone and the text beeped almost immediately.

“Great, I’ll call you in a day or two after I’ve had some time to digest all this. Now I need to get back to work.” I drained my coffee and stood up. Kelly stood, too, and gave me what looked like a platonic hug and kiss on the cheek. But after the conversation we’d just had the contact was anything but platonic. It lingered a moment too long and I felt the distinct pressure of Kelly’s breasts against my chest and her pubic mound against the bulge in my trousers.

“Hear from you soon,” she whispered in my ear. I gave her one last searching look and with a deep sigh I headed to the counter to pay the bill.


I climbed into my car on the street but just sat there looking back at the café — still trying to digest what had just happened. A few minutes went by before I saw Kelly emerge and walked briskly away along the footpath. I watched her out of sight — a confident, fit young woman in the prime of life. I smiled to myself and shook my head in wonder. By then of course I’d all but decided that I would do as she’d asked. I’d fuck her. I’d fuck Kelly. Beautiful Kelly Benson.

And she was damn beautiful too. She had what I considered to be the perfect sportswoman’s physique: medium height, compact and sleekly muscular, with taut breasts, a slim waist and straight shapely legs. Add to that her clear complexion, brown eyes, flashing white smile and long dark hair and … well you get the picture.

I continue to sit there considering the girl I’d nursed in my arms as a baby and had watched grow up. If the beautiful Kelly had faced any problem at all in her life, it was growing up in the shadow of her even more beautiful twin sisters, Emily and Laura. Those two had been capturing hearts — and all the attention of family and friends — since the day they were born. They’d grown up tall, tanned, blonde and startlingly beautiful. On top of all that they were identical twins, so they’d been in demand from photographers since pre-school and it was no surprise that they’d capitalised on their natural talents by becoming photographic and catwalk models from the age of 15. At 26 they were highly successful and moderately wealthy. It was also no surprise that their shorter, less-photogenic, little sister was often relegated to the background. Not that Kelly seemed to mind. She had found her own modest celebrity status on the sports field. A natural at any sport she tried, she eventually settled on field hockey as her sport of choice. She loved the fast pace of the game and the team camaraderie. She was now playing at state level and was knocking on the door of national selection where, these days, you could actually earn some good money. Her sisters had helped her find some sponsorships, too. So, although Emily and Laura tended to hog the limelight, Kelly had carved out her own small measure of fame. All three girls were close; though naturally the twins were closer. Emily and Laura lived with their boyfriends in neighbouring apartments and often worked together on modelling assignments. Kelly loved them dearly but always declined to appear in celebrity family photo-spreads because, next to her sisters, she felt like a complete plain Jane.

All this was running through my mind as I sat in the car, overrunning my lunch hour. Eventually, I grabbed my phone and texted Kelly.

“I have a few more question. Can we chat online tonight?”

The answer came immediately: “Sure, I’ll be home all night. Just dial me up when you’re ready. And thanks again! ? xx”

Jesus Christ, I thought to myself. She’s thanking me when she’s offering me every middle-aged man’s dream. Finally I started the car and headed back to the office — though work was the furthest thing from my mind.


Me: Hi Kelly

Kelly: Hi David xx. Why aren’t we just talking about this on the phone?

Me: This is just a bit easier for me — less embarrassing perhaps. Shouldn’t take long.

Kelly: OK sure — I can go with it.

Me: OK so having thought about it my provisional answer to your request is “yes”.

Kelly: OH YAY!!! But provisional????

Me: Yes. I have a few more questions and depending on your answers — a few conditions.

Kelly: OK shoot! ?

Me: First of all is everything you told me today the truth? You really are still a virgin?

Kelly: OMG David!! Why the fuck would I make up something like that???

Me: Yeah, I guess. Just wanted bahis şirketleri to be sure. But I do have some much more personal questions. I hope that’s ok?

Kelly: Of course

Me: Do you still have a hymen?

Kelly: Ha ha — wow you’re getting really scientific now. Does it matter?

Me: Yes it matters.

Kelly: OK — the answer is I don’t really know — since no-one has actually tested it.

Me: So you haven’t been penetrated? Even by sex toys or anything?

Kelly: Not really. I’ve used them but only for — shall we say — external stimulation.

Me: Do you masturbate?

Kelly: Of course!

Me: Do you orgasm?

Kelly: Sometimes

Me: Sometimes?

Kelly: Well … I don’t seem to cum very easily. All the planets need to align, you know: my mood, my hormones, my mode of stimulation, my particular fantasies. It can be a bit tricky.

Me: OK – I understand. Next question — are you using any contraception?

Kelly: No — I thought you might take care of that.

Me: Sure — no problem. And finally — please don’t take offence — but are you sure you’re batting for the right team?

Kelly: You mean am I actually a closet lesbian?

Me: Um — yes???

Kelly: Jesus — what is it with you men? You think any woman who plays professional sport must be minge munching every other woman in the dressing room!

Me: Come on — you know I don’t think like that. It’s just I want to be sure you’ve considered that possibility.

Kelly: OK — yes — I’ve considered it. And no, I’m not batting for the wrong side. I’m straight. I’m pretty sure I love cock — I just haven’t got close enough to one yet!

Me: OK thanks — I just needed to cover all the bases.

Kelly: LOL — it’s ok. Any more deeply personal and politically incorrect questions???

Me: LOL — no I think that covers it. But now for the conditions, OK?

Kelly: Sure Mr Romantic — fire away!

Me: If we go ahead with this, no-one — and I mean NO-ONE — can ever know about it! OK?

Kelly: What? Not even my parents?

Me: That is not funny!

Kelly: Sure — no-one but us will ever know. Promise.

Me: OK. Next — we’ll do this on neutral ground. Not at your place and not at my place.

Kelly: Sure. So will I book the sleazy flea-pit motel or will you?

Me: Very funny. I will book us a hotel room — maybe somewhere one step above sleazy.

Kelly: Phew!

Me: Finally — you know I do love you — like an uncle or much older brother. But I’m not “in love” with you and don’t intend to be. This would be just sex okay?

Kelly: Jeez David — don’t sweep me off my feet with romance or anything!

Me: Come on — you know what I mean. After this is over we have to go back to our very affectionate but platonic relationship.

Kelly: Of course — but FFS you’re making it sound like a form of torture you just have to grit your teeth and get through.

Me: You know I don’t think that. The truth is I’m really looking forward to it now I’ve got used to the idea. You are beautiful and sexy and right now I feel like the luckiest man alive. But we can’t afford to lose perspective.

Kelly: Well, thank you for those lovely words and you’re not the only one looking forward to it. So, when do we do this?

Me: As soon as possible before I get cold feet. What’s your playing schedule?

Kelly: Home games for the next two weeks so any evening should be ok.

Me: Ok — how about Saturday night? Three days from now.

Kelly: Perfect — and thank you so much for this!

Me: LOL — you’re thanking me!! This is any old man’s dream! I’ll text you the hotel details and meeting time when I get things sorted.

Kelly: Ooooh lovely!!

Me: And one more thing…

Kelly: Yes?

Me: I want this to be a very special and memorable adventure for you — as it will be for me — so wear something elegant and sexy!

Kelly: HOT DAMN!!!!!


So it was fixed for Saturday night.

But as the time drew nearer I found I was getting quite nervous about the whole affair. I became fully conscious that Kelly was depending on me to ease her into — well, “womanhood” — if such an old-fashioned term could even be applied anymore – and I resolved to make the whole thing as smooth and pleasurable for her as possible. And that would involve thorough preparation.

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