#40: Ruby in the Rough

Whoosh! A hideous collection of snot and tube gunk washed out of my nose into the eager tissue held tightly in my hand. I looked down at what I had done, as I’m want to do, and saw blood spattered in amongst the mess. I was due a nose bleed and today it decided to make its long awaited comeback.

I tipped my head back to redirect the flow down my throat and lightly held a clean tissue in place. To any observing all they saw was a probable toff, turning his nose up at the surrounding world.

With a deft movement I freed one of my hands and reached down into my right jean pocket, retrieving my Oyster Card and tapping out of the Underground, then took a left and emerged onto Argyle Street.

The cold January air hit me immediately and I took a deep breath, drawing a small part of the street itself into my lungs and feeling its vibe. I moved it around my tongue, like a wine taster identifying the subtle flavour notes, then blew it back out.

The first thing I sensed once I let out that cold air was the pointed tap of heels on the cobbled street. I looked to my left and spotted the offending articles, clip clopping away, then as my gaze went up I was met by an incredibly long set of thin legs and then a furry, fuzzy coat and finally a wash of curly hair.

My feet started to move before all of these observations had hit home and I prayed that my nose wouldn’t show me up.

As I went level with her I locked into her big, brown eyes and got directly in front.


“Woah, woah, woah, stop, stop, stop”. She stopped.

“Right then… Hello. I saw you trotting down the street. I noticed that you have these sprightly gazelle legs. They’re very nice.” She giggled and smiled, I could tell that she was now rooted to the spot and certainly interested.

“My name’s Tom”, I said, offering my hand.

“Maria”, she smiled, offering her own.


I took Maria’s hand in mine, not planning for one moment to actually shake it, and held it there softly.


“Maria…hmmm… I suppose everyone else has Marias. In England we have Marys. But in England that’s an old woman’s name.” She giggled sweetly, and her eyes twitched in attraction.

“I’m actually Romanian”, she told me.


We chatted freely for about five minutes and Maria told me about her fashion course and what it was like moving to London. She was really enjoying the city and I could tell that it made her feel very grown-up, as she was taking her life in its own direction.

My eyes lazily drifted down to those long legs.


“My goodness I’m sorry!”, I said, snapping my attention back up, “I was distracted by your legs. They’re very nice”. More giggling. Classic Krauser.


I playfully teased her a bit more for how she pronounced certain things and slid into the number close with ease. It felt like sinking into a warm bath and toying at the bubbles with your feet.

We met three days later near Crown Plaza and she was bang on time. I’d told her to “dress rebellious, so we match”, and she’d done her very best to comply. I felt like a boss when she came up out of the tube station in those same heels and spray on jeans, with a sparkly top and leather jacket. Insta-boner.

I gave myself an inner-high-five and filed the scene away under “positive reference experiences”. Here was a girl who was undeniably hot and had so far proved very compliant. I was starting to feel more and more like a “hot guy”.


“Hmmm”, I looked her outfit up and down, “7.5”. I pretended to hold up one of those score cards they use in the Olympics.

“What?!”, she played along, pushing her lower lip out like a little girl.


I led Maria down the street and into my first venue, a pub, but it was packed and there were literally no seats free. Again I felt like a boss, bringing the hottest girl into the venue.

Not a problem, I thought to myself, and we instead went next door to a wine bar where we settled onto a couple of stools with two glasses of sweet white wine. It was quiet inside, a couple of friends sat sparsely at the tables. Not perfect. Not rock and roll. Not rebellious. But it would do. I knew I’d had to have balls and do all of my verbal escalation knowing that everyone else could hear me.


“How far did you come today?”, I asked, expecting her to tell me that she lived in university halls somewhere in London.

“From Watford. I’m staying in a house my mum bought but she’s away for two weeks”.

“Blimey!”. That was a green light. It as over an hour away and this was her little secret adventure.


Maria told me about her course a little more and then I steered the conversation onto the guys she was into, and her celebrity crush. Thankfully this time she said that it was guy.


“Be honest, what do you like about me?”.

“Hmmm, I dunno!”, she giggled a little bit but I pressed onwards.

“Come on, there must have been something you liked for you to be here tonight”.

“Well I really liked your beard, and your blue eyes”. She said as she looked deep into the aforementioned.

“Thank you”, I said graciously and nodded.


Spotting a couple of seats next to our stools I told her we should move into them, and again we sat at right angles to each other. She said something in her accent but I couldn’t pick it out.


“Come a bit closer, I can’t hear you properly”. I said earnestly.


Maria shifted closer and now her knee was directly touching mine. She sat thigh over thigh, leaning forwards, which her hands clasped together on her knee so that when she moved them, her fingertips flicked my legs.

That was a signal, so the next time I made a point I took her hand in mine gently, and when I was done I let it go. No resistance there, so when I made my next point I took her hand and left it in mine, gently stroking her fingers, which she returned.


“Do you think I’m more serious or silly”. I held out both my hands to indicate a spectrum. “If this is fully serious”, I brought my left finger up, “and this is fully silly”, I held my right finger up, “where am I?”.

She thought about her answer before plonking her finger down at about 60% silly. “Here!”, she claimed triumphantly.


I took both of her hands and made the same spectrum but then I chose for her.

“I reckon… you’re about here”. I gave her a 70% silliness rating.


Taking both of her hands in mine, I looked at her and we established deep eye contact. “If I don’t do this now, I’ll be kicking myself in five minutes time”, I thought, before pulling her in and kissing her.

Something exploded between us and it was a full makeout straight away. Some of the other patrons looked up from their wine but then settled back into their conversations.

I took stock of the green lights that Maria had given me so far and decided there was going to be no venue two, it was time to brass neck it back to my place. And brass neck it I did.

We got to my front door, no problems so far, but I could tell that Maria was reticent to come in. She stood on the precipice of the doorway and I had to gesture to her to move forwards. The same thing happened when I unlocked my front door. She stood there, not knowing what to do, and again I ushered her in and sat her down. Indicated that she should take off her shoes and her jacket, which I popped to one side.


“I just need to check my emails, I’ll be back in a sec”.


When I returned I got us a couple of drinks from my fridge and we sat down on my sofa. The warm glow of my red lampshade casting us both in a seductive light. Slow and sexy rock music purred in the background.

I pulled her into me, and reestablished the kiss. Straight into a makeout again. This was looking to be a slam dunk.

I squeezed her tits through her top and her breath came quicker. I kissed her neck and bit her earlobe and she moaned in pleasure. Taking my right hand I drew up her top and undid her bra. Small tits, but nice.

I went to undo her jeans and got the first resistance.


“We can’t do this”, she said.

“It’s okay, I understand how it is for girls”.

“No, but I don’t think you understand”.

“It’s fine”.

“Do you know what the issue is?”.

“Girls get scared before sex, but that’s all fine and expected”.

“No, and yes, but no”.

“Alright, are you on your period?”.


It could only be one more thing.

“You’re a virgin”. She nodded sheepishly and looked away.


I took her hand and soothed her, leading her into my bedroom because “it was more comfortable”, where we lied down and continued kissing.

I started to play with her clit, but when I tried to go right into her pussy she grabbed my hand.


“No, if you do that I won’t be a virgin anymore”.


Two steps forward, one step back. The current aim was for us to just be naked together, so we kissed a bit more and I got her jeans off, saying that they were hurting my hand. Next I got her underwear off for “easy access”. There was actually an unblemished Tampax in there… four in a row: the streak continues. 

As I played with her clit her whole body would shake, and soon enough we were both lying there completely naked, but whenever I tried to actually finger her she would block my route off.


“How far have you ever gone with a guy?”, I asked.

“This is the furthest”. She was 19.


I put her hand on my dick but she just left it there on top, not grasping it or anything. I had to put her hand around it and wank myself off vicariously.

I was still getting the same resistance, and knew at this point I had to push her away. That and cum, so I spanked her and fired a warning shot across her belly.


“I’m feeling tired, let’s go to sleep”. She acquiesced.


Turning away from her I fell into a nap for about thirty minutes and when I awoke, craftily let my hand stray down her body and back to her pussy. However, this time, she let me put the first digit of my index finger inside. We were making headway.

We kissed more, I got my finger a little bit further inside, but eventually, again, her hand came in and pulled me out.


“Why are you not giving up?”, she stressed.

“Because I find you attractive”.


This game went on for another ten minutes or so, but I was getting tired of it. I wanted to fuck her, but maybe her pussy wasn’t going to be the proud recipient this day…


“Has anyone ever fucked you in the ass?”, I asked somewhat pointlessly.


“Turn over”.


I rolled her onto her front and straddled her from behind while I got some lube out of my sex drawer. Lathering some onto my finger, I slowly pushed it into her butt.


“How does that feel?”.

“It hurts, but it’s good”.


I felt her relax, and then put my dick in too.


“It hurts! Am I not virgin anymore?”, she asked. I reached down and checked. Nope, it had definitely gone in her ass.

“Yep, it’s okay, it’s just in your ass”.


I went back and forth a little then drew it out. Fucking hell she had a great body. Those long, slimline legs, spankable ass and tiny waist.

I went to put my dick back in her ass but it was so tight. I slipped and it went straight into her pussy.


“Ahh!”, she cried, “what have you done?”.

“Shhhh”, I soothed her, “breathe with me”.

“Am I not virgin anymore?”, she asked.

I sent a hand down to check. “Nope”.


I slowly, very slowly, thrust in and out and eased her into it.


“Turn around, let’s do this properly”, I said, turning her over, looking deep into her eyes and kissing her.


I got a condom out and put in on, and inch by inch slid my dick into her.

“Breathe”, I continued, calming her down, and made deep and purposeful breaths for her to follow. She took it like a champ, though, and after a couple of minutes I asked her how it felt. She thought for a moment, and said it was good, so I went a little harder and deeper. I started playing with her clit as well and her whole body shook, her head tossing from side to side.

I showed her a few positions then went back to missionary and came, before quickly retreating to the toilet where I jumped up and down on the spot like a giddy school girl and gave myself an enormous inner high-five.

I returned and she looked contemplative so I pulled her in, kissed her a little more.


“Why did you do this to me?”. She was trying to shift all responsibility to me, absolutely expected behaviour and totally fine.


A lot of introspection was due on her part. I could tell that she had a lot to think about so I held her there and didn’t say much, just absentmindedly playing with her hair drawing my fingers up her back.

It was a special moment for both of us. She was the first virgin I had ever fucked and I could tick that off of my player goals, which felt good.

But the more impactful change was at a deeper level of identity. This was clearly a hot girl and I felt like a hot guy. I hadn’t need twirly PUA magic to get her, I just had stay calm and show my intent covertly. 

On her part, I’ll always be her first. For good or ill, I’ll always be in her mind and have permanent residence in that corner of her memories. Whenever she has sex, she will at some point think of me.

I didn’t want her to feel bad about it, though, I wanted her first time to be a good memory, so as well as holding her, I told her that it was good that she had lost it to someone who knew what they were doing.

“With an older guy as well, you’re friends will be jealous”, I winked. She giggled and started to run the scenario through her head.

Like I said, she had a lot to think about. Am I a slut? I enjoyed it too, does that make me a bad girl? Did I make the right choice? Can I trust this guy? Will we date and become boyfriend and girlfriend? What will my friends think? What would my family think if they knew?

I’m sure she had more questions but I let her mull them over herself. That was something for her and her friends to debate endlessly, not me.

Yours unfaithfully,

Thomas Crown


5 thoughts on “#40: Ruby in the Rough

    1. Yeh this Friday we’re scheduled to meet again. It’s weird though, because normally after sex I’ll present the frame of FBs. With this one I feel like I need to wrap her in cotton wool. Don’t know if this is good or not.


  1. Impressive.

    “With an older guy as well, you’re friends will be jealous”, I winked.
    Thank you for that line, absolutely great and well specifically appreciated, as you know 😉


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