So we were sitting on my futon chatting and drinking wine, Angelina now had no pants on and I could see her underwear sticking out from under her shirt. This was the new reality that I had adjusted to. Perhaps her removing her trousers was supposed to be the spark to ignite some fiery physicality, but she had been so matter of fact about taking them off as a means to make her more comfortable that I'd just continued with normal conversation.
At some point we transitioned to watching YouTube clips from obscure Puerto Rican cinema, and she transitioned to sitting on my lap. Having watched a scene about some pimps engaged in a knife fight over a particularly attractive hooker, I decided it was time to focus less on the computer screen and more on the ass perched on my crotch.
After some awkward kissing and groping on we slumped onto my bed. The rest of our clothes worked their way off and were flung back onto the recently vacated chair… or missed it and fell onto the floor.
Once Angelina was naked and I was down to my boxers, I rolled her over onto her front, exposing her bare ass ready for spanking. I struck her with my open hand and watched the impact rippling outwards and up into the rest of her body. It wasn't an exceptionally large ass, but there was enough junk in that trunk for it to show some good rebound, and a little bit of jello-like wobble.
"You're going to have to hit me harder than that!" she said, "I can barely feel it!"
With that invitation I didn't hold back and spanked her aggressively. She grunted and gasped with excitement, but then she retorted; "Is that the best you can do?"
I gave her a few more brutal swipes but even if her ass wasn't feeling it, my palms were starting to sting and curse me with each impact. She was really asking for it now. I decided to give my hands a rest and drew out a 30 cm plastic ruler from my stationary drawer. This made a sharper sound when it struck her buttocks, and the ripples moved faster and dissipated more quickly.
"Harder!" she said
I hit her harder.
"You don't have to hold back. I can take a lot of pain!" she added .
The problem was that I wasn't holding back.
I was surprised this wasn't hurting her more. I really put my back into it, striking her hard and fast, quickly switching between ass, back and thighs, then returning to her ass to give it a concentrated thwacking.
"Harder!" she grunted between gasps and moans. Suddenly, after one particularly furious thwack, there was a snapping noise and the last 0.6 inches of ruler broke off and flew through the air. It hit the wall and then fell down somewhere under my bed.
I had been pretty aroused since first groping Angelina on my lap, and I remained positively tumescent while exercising my ruler swinging arm. After a bit more tumbling and thumbling it seemed like an appropriate time to initiate intercourse.
This, however, is where I ran into problems.
It was safe to say that we weren't entirely sober at this point. Neither were we entirely drunk, but I wasn't in a place where I wanted to attempt any complex bondage, and rolling around on my bed with occasional spanking seemed like more than enough fun. Condom on I tried to locate my dick into the conventional dick accepting area. This proved more challenging than usual, and to begin with Angelina lay there submissively, expecting me to figure it out by myself. This is not something I would normally find difficult, but after the beer and wine there seemed to be a lot more folds and misleading crevices than usual. I double checked with my fingers. 'ok, I need to be aiming a bit further back, right... almost... no... Ok... There we go!'
At last, sex had commenced. Unfortunately though, my vagina locating difficulties were just the start of my problems. You see, somewhere in between the ruler breaking and intercourse making, my penis had started to get stage fright, and then when it had failed to find a receptive audience on the first attempt, the pressure had really started to get to it. Even though it had now found the way in, I could tell that my erection was in a nose dive, its wings shredded by 50 mm cannon and fiery black smoke spewing from the engines.
A miss-timed thrust and out it came. My plane-erection metaphor slammed into cold hard waters of the North Sea with a wet thud, sending up a plume of ocean spray and discombobulated metal before sinking down into the ocean depths, never to be seen again.
Ok, so in real un-metaphorical life there was no discombobulated metal or plume of ocean spray (ew). However what I had to deal with instead was one pissed off Puerto Rican.
"Afraid I'm having some problems here," I muttered.
"What? Unbelievable!" She said, in a less than encouraging tone.
I fiddled with the problem, and then Angelina fiddled with it AGGRESSIVELY (the image of her mouth tugging my right testicle out to its natural extent, while my penis remained stubbornly flaccid in the foreground is one that haunts me to this day). However all was for nought.
"Ergh... come on penis, you're letting me down here!" I said... to my penis... out loud.
"I’m so offended! Are you not turned on by me at all?" she questioned.
"What? No, of course I am! Did you not see that I was turned on earlier?"
"Whatever. You're clearly not turned on now!"
This added drama was not conducive to my erection's return, and now I had to expend significant energy convincing Angelina that 'It wasn't her, it was me'. Pointing out that I had drunk a fair amount of alcohol, which probably wasn't helping, and also informing her that this had happened to me once before with another perfectly attractive girl, seemed to placate her temporarily.
"Will it turn you on if I use the ruler on you?" she asked
"Could give it a try," I replied, doubtful anything could bring my erection back onto the stage after its first performance had been so disastrous.
I lay on my front, naked and supine, and she slapped the WHSmiths "Shatter resistant" (but clearly not that shatter resistant) plastic rule across both my ass cheeks.
She did it again, and again. I grunted and gasped accordingly. It certainly hurt. This was the sort of thing I had spent countless nights of young adulthood fantasising about, one of many ideas that would percolate through into my consciousness uninvited when I was trying to sleep, and then force me to address my rock solid member just so I would stand a chance of dozing off afterwards.
There I lay. Getting spanked. One of many dark fantasies materialised... and yet instead of being overcome with arousal I was wondering how many stinging blows I should take before I'd tell Angelina that this really wasn't doing anything for me. I mean, it was still doing something for some part of my brain, but all the important bits of my subconscious that controlled the valves and pressure gauges had long since shut themselves away with a 'do not disturb' sign on the door handle.
Frustrated with my failure to respond to the ruler, Angelina resorted to sitting on top of me and humping me for a while. She ran her nails down my chest, digging in HARD.
"Mnnhhh!" I winced.
After a while she looked down.
"Shit, I really scratched you!"
"It's fine. It did feel pretty intense though."
"I've left some major red lines there. Sorry."
"That's ok. I guess I deserved it," I said with a smile.
Accepting that my penis had nothing more to contribute to proceedings, I had a new idea to potentially satisfy her and at least entertain me. I fetched a banana from the kitchen.
"I'm going to fuck you with this instead," I said.
"Are you serious?"
I slowly slid it inside her. It seemed to be a pretty good fit, and I worked it backwards and forwards… "No... It just feels weird!" she said after a few minutes of being violated by my 19c grocery from Trader Joes.
Abandoning the soft fruit approach I tried to pleasure her orally. This was a failure as well. She discouraged me almost immediately by impersonating my expression with tongue distended, and claiming I looked grossed out and totally unsexy.
In the face of this unrelenting and un-constructive criticism I gave up completely. We turned in, but I consoled Angelina: "The last time this happened I woke up in the night with a raging hard on so I'll ravage you then."
Later in the night I awoke and my erection had returned in full force. I lay there motionless under the duvet pondering. ‘On the one hand there is an attractive girl in bed with me who a few hours ago had been eagerly awaiting the return of this creature,’ I thought. ‘On the other hand she is asleep. There is also a chance that if I wake her to do what this organ is craving it might suddenly change its mind again.’
I decided I couldn't deal with the emotional fallout of waking her up for sex only to risk another return to flaccidity. And besides, I was sleepy!
The next morning, after some ablutions, I found myself sitting in my desk chair while Angelina emerged from under the duvet. Working herself upright, she retrieved and donned her underwear, then swung her feet out and down onto the floor. She sat motionless on the edge of my bed in her purple bra and turquoise panties and stared silently at me for what seemed like a soul questioningly long time.
“No? Nothing?” she asked.
Figuring she was referring to my erection I replied: “No, sorry… I think I’m just in a weird place right now.”
As I walked her out I half expected her to leave in a huff but instead she said “Well if you just want to hang out as friends sometime let me know. I know some cool places downtown we could go.”
“Cool, yeah. I’m not saying I wouldn't want to try this sort of thing again. I guess I'm just not in the right place at the moment. Let’s stay in touch though!”
We didn't stay in touch though. Part of me wanted to message her just to see how she was doing but the other part was concerned that drawing out our connection could be somehow damaging to both of us. It seemed like drama was an intractable element of our interactions and, as other less dramatic things were working out for me, I left Angelina to figure out her own thing. I hope she did.
 On reflection my belt might have better satisfied her lust for pain, but it had fallen down somewhere and I didn't want to have to go look for it.
And by 'audience' I mean 'vaginal opening'... but you know... it's nice to keep some shreds of class.
 The first metaphor I was going to go with was "Like a bratty child unable to cope with the frustration of its tower of bricks falling over, my penis had thrown a tantrum and left the room, slamming the door behind it." However I wasn't sure if there were laws against putting children and naked penises in the same metaphor....
 She fell asleep pretty quickly, and I could tell she had drifted off by her snoring. I had just dozed off myself when I was suddenly jolted back into consciousness by a terrifying growling-gargling noise. After a few fear-stricken moments I realised that it wasn't the sound of some blood-thirsty werewolf baring its teeth over me, but instead was coming from the unconscious girl I was sharing my bed with. I looked at her trying to figure out how a human could simultaneously make such a terrifying guttural sound and yet look so peaceful… Perhaps some kind of sleep apnoea? Was it a medical thing? Should I do something to prevent her from expiring? Fortunately after I made a coughing noise and poked her a bit with my knee she shifted position and the deathly growling changed back to annoying snoring.