Vertical Challenge

(Me panting) ‘I thought you said you did this before? And now you are the one stopping before me.’

The weekly climb up the tallest HDB in Singapore started about a month ago, when Michelle asked me along to accompany her to ‘get into shape’. I remembered the first time we scouted for a venue, and she did the climb in a maxi skirt. As we met over the weeks, I saw her in track pants, yoga tights, then running shorts, and now, yoga shorts – the type with a coloured band around the waist of a tight-fitting, ass-hugging short, shorts.

Just fifteen floors up the block and she could not pick her ass up anymore, quite unlike her usual performance levels.

‘Can I go ahead first? You can take your time.’

‘No no! Wait for me! Please.’

She immediately grabbed my shorts and tugged it dangerously hard, almost exposing my underwear-less state since I was in a netting-lined running shorts. Michelle didn’t let go even after I gave in, and kept pulling me to sit down with her. When she went too far and lowered my bottoms too much to reveal my pubes, I quickly joined her and let her hold my arms so I wouldn’t ‘run away’.

(She whispered) ‘Are you wearing any underwear?’

‘Umm no. You too right?’

‘Hey! How did you know?’

‘Your shorts are not usually this wet. So I suspected you didn’t wear it today.’

True enough, her thigh gap was in a darker shade of grey, but it wasn’t anything arousing since I knew it might appear even if she wore something below. The unnerving silence came and went, just as she began to lower her shorts to her ankles. Thinking that she was checking on ‘something’, I looked away until she took my hand and placed a finger on what felt like a string.

(She whispered) ‘I have Benwa balls inside me this time. I bought it from you.’

‘From me? No way.’

‘Yes way.. ‘

She looped the string around my finger and ‘used’ me to pull them out, dripping juices all over the floor as she forcefully kept them in my pockets. The next thing I knew, she was rubbing her clit with my fingers, to relief the temporary ache from the removal.

The moans from an athletic, tight young body got me hard in no time, and she saw exactly what she thought I would do – to adjust my erection.

‘Come up.’

She dragged me to the flat ground connecting two flights of stairs and sat me down. Without any baggage on us (save for her toy), a condom was out of the question. I was pinned onto the ground as she climbed onto me, placing her wet pussy right above the tip of where a drop of pre-cum had oozed from.

‘This is going to be my new exercise.’

A cheeky grin followed her words and we watched her vagina claiming what wasn’t hers. The slow penetration got the both of us groaning as pleasure overwhelmed our tired legs, blasting their way through our sweat-covered bodies. I lent her my hands to let her sit upright over my cock, and she was showing the most sexy, agonising look as she adjusted her hips on mine.

(I asked) ‘Are you sure?’

‘I didn’t ask you along for no reason right?’

So, she has been planning for this to happen? My thoughts couldn’t stay long in my head once she began grinding, lifting and dropping her ass on my dick that was sliding along her vaginal walls to give us the waves of dirty groans. Michelle’s eyes were locked on my face while she moved at different speeds, throwing me into tiny fits as I was pushed to my limits at her mercy.

In the diminishing light of the setting sun, the corner we were fucking in got as dark as it could get before the corridor lights came on. Somehow, her clit was really sensitive and she could climax within minutes of my teasing. The Benwa balls worked better than either of us had expected, driving, or forcing her to rock her waist harder and faster than what she could manage, like getting possessed by the most horny monster ever.

(She moaned) ‘Fuck fuck fuck! I’m coming!’

Her pussy slid against my groin harder and harder with her fingers furiously attacking her clit, until a load of juices started pouring out, and flowing all around the sides. Sensing her pace decreasing to the orgasm, I lifted my back off the ground and picked the both of us up in my arms, without so much disengaging our gentians for a second.

Michelle knew what position was I getting into at once and held me tighter around my neck as soon as her back touched a wall, legs wrapped on my back with some leeway for my dick to thrust.

(I whispered) ‘Your turn now.’

She said nothing and placed her head on my shoulder, allowing me to swing my hips at her, to shove my cock as deep as I could into her pussy, that had no escape with her ass against the wall.

The amount of wetness, tightness, willingness, moans, triggered something in me I couldn’t understand. My body automatically went into a constant rate of thrust, as if taking what it needed to survive – sex. I knew it wasn’t pleasure when her pleas for me to be gentler, turned me on even more.

I know how much she needed me to relax, and that was exactly what I didn’t want her to have. The contracting pussy only drove me wilder as I shifted to the steps, placing her down to pound her even harder.

(She moaned) ‘OH SHIT OH SHIT!’

Her nails dug into my neck and the widest eyes stared their hardest at me. Her jaws dropped to let the silent scream into my face, and then, a jet of juices splashed into my belly and diverted onto her abs.

My dick chose that very moment to cum, and the momentary ‘peak’ gave me time to yank my cock out of her. She instinctively pulled my thighs for me to go up to her and another jerk behind my knees caused me to fall forward, stopping my dick just right at her face.

One hand (of hers) let go and went down to her pussy, while the other kept pushing my butt to stick my cock into her mouth. I went in her direction and plunged it right between her lips, face-fucking her for a minute or so before I froze.

A single slide of her mouth along my shaft blew my cum into her mouth, filling her as much as I had to offer. The ‘s-experienced’ girl parted her jaws at times to let me have my weakest moments to myself, and proceeded to clean me up without sucking. She just squeezed her lips around my base, and relaxed her head away to get the last bits out of me.

My recovery took longer than usual after the strenuous ‘delivery’, and we sat quietly next to each other while we rested. During that time, I helped put her shorts back on, and she went down on me for another few separate times whenever she saw cum escaping my pee hole.

(She panted) ‘That’s my protein shake.’

‘And I’m the one who can’t move now.’

With the groin area of her shorts wetter than ever, we couldn’t go anywhere until she was dried.

After that night, our stair-runs were no longer the same, spending our break time doing another ‘exercise’ till we were too tired to continue. For half a year, she did enough cowgirl-style sex to get the figure she wanted, and then it was my turn to achieve the body she fantasised her man to have – through the ‘missionary’ and ‘doggystyle’ positions she read on dubious websites.

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