Under Her Dress

Donned in her short black dress, her alluring legs were tempting me to just grab her waist down on my dick if there wasn’t anything under. But such a innocent lady like her would definitely protect her modesty from such minds like mine. We strolled through the wavy paths of the park leading to her place, and time was running out for me to break this girl in. The straps across her shoulders complimented her fair complexion and the boney structure showed me how thin she actually was. I had never seen her in a dress, but this one time she wore it, was sufficient to inspire the darker side of me.

Just in time as we walked passed a pavilion, her phone dropped onto the grass patch and she conveniently bent over to pick it up, allowing the laced knickers under her dress to greet me. Well, the shortness of the dress did seemed shorter after the upskirt, but what really turned me on was the pair of shorts-like protective knickers. It wasn’t skin tight, and appeared to be more of a pair of shorts than undergarment.

Casually, she turned to see if I was still behind, and I smiled at her.

Me: ‘Do you need to go home before a specific time?’

Her: ‘Nope. I was about to ask you that too.’

Me: ‘That pavilion?’

Her: ‘Okay.’

We walked over to the shelter and the single LED lamp provided an ambience so soothing and sensual, especially the warm yellow lights that bounced off her smooth skin.

Her: ‘I have something to tell you.’

Me: ‘Go on. Don’t scare me with any surprises k?’

Her face was turned towards her own hands on her lap as she blurted the secret she had been keeping, and to be frank, my heart was pounding real fast after she had something to say.

Her: ‘I.. actually liked you, but you’re my best friend’s boyfriend. So I didn’t dare to say anything.’

Well, she had asked me out that night cause I had an unexpected day off for an urgent meeting at the management level. Coincidentally, we were in contact to solve some of her laptop’s issues and we met up so she could thank me over a dinner. It was so last minute and sounded so casual that my t-shirt and shorts attire did no justice to her elegant outfit.

Me: ‘Is that why you wear this nice for a dinner at a shopping mall?’

Her: ‘Part of it?’ I wanted to know if this dress looked nice too.’

The shy lady sat closer to me and rested her head on my shoulders, while ‘accidentally’ showing her cleavage to me. I simply placed my arm around her waist and held her, as she kept her eyes on my shorts. Pervertedly, I moved my arm to her neck, and massaged her so she would feel more.. tempted – hopefully. My hand then slid down her collarbone, and poked my fingertips into her dress, pressing lightly onto her breast.

Me: ‘You know we can’t be together right?’

Her: ‘I know. But I don’t mind sharing even just for a moment. I want to know how she feels.’

I was still trying to figure out if she meant how her best friend (also my girlfriend) felt while I was inside, or being together with me. Still having no resistance to my naughty hand, I pushed my way into her top and felt the silky, soft padding holding her boobs. It went over my fingers and my hand was over her left breast, with her nipples between my digits.

From where I was, I couldn’t see her face and guessed she would be too shy to look at me too. As I fondled her nipple, her hand moved to my shorts and felt the bulge in her palm. I shifted to the other side of her chest and she slipped her hand under my shirt, wriggling her way into my pants. Expectedly, her manicured nails touched my manhood and it twitched excitedly. It was the thought of an innocent and ‘untouched’ girl advancing on me that was making me so crazy about the whole thing.

Right after her fingers went around my rod, I adjusted my position to let my other hand go under her dress, where her safety shorts protected.

Her: ‘You want me to remove it?’

Me: ‘Is it convenient?’

Her: ‘I don’t mind.’

She pulled the loose shorts off and placed it into her bag, before resuming with stroking me and giving my hand the space to come in contact with her privates. Right as I was about to probe down her slit to her clit, she gave the surrounding a quick glance, and raised one of her feet to the seat. Though it was still cramped between her legs, I could not care anymore and just went for her clit, rubbing it slowly so as not to disrupt her pace. There was something to check before I stuck my fingers up the wrong place.

Me: ‘Have you ever fingered yourself?’

Her: ‘Everytime I think of you.’

My hard on became harder from her reply and she felt it thickening slightly, before pulling the waistband wide to let it out into the earthly smelling fresh air. The petite girl’s head went down my chest and let a small amount of saliva drop over it, before pumping it with her hand faster.

Me: ‘Do you want to help me shoot?’

Her: ‘Yupp.’

A handjob is better than none right? I shoved one of my fingers into her and a tight grip on my arm signalled me to slow down. I went at low speed, pushing my fingers in and out of her, and felt her pussy tightening around me.

Her (whispering): ‘You can go faster if you want.’

Of course, I rammed my hand into her faster and she responded by opening and closing her thighs. I messed up the tempo she had on my dick but I was determined to give her an orgasm before anything else. Sinking two fingers into her pussy, I went at my fastest till her head fell backwards and both her feet went onto the seat, widened. A few minutes later, she abruptly hugged me and a slight shiver went through her body, while juices leaked calmly out of her lovely slit.

Her (whispering): ‘I like it when it flows down your fingers.’

Me: ‘Did you do this with your ex too?’

A sense of guilt overcame her and she nodded, but quickly adding on that he was more concerned about ejaculating and only helped her after he had unloaded. True or not, it didn’t matter to me, cause he was the past. I had won her heart and perhaps her body with this move and my slow moving fingers kept her jerking me.

Her (whispering): ‘I want you inside me. Can?’

Me: ‘But you’re supposed to save it for your boyfriend, or future husband.’

Her: ‘I don’t mind giving it to you. I won’t regret.’

Me: ‘You sure you want it?’

The determined face nodded and I made her stand, between my opened feet. She peeled her dress upwards and sat over my raw dick with her legs together, leaving the guidance to me. I held my rod upright to let it in and her pair of hands on my knees grabbed tightly. Her pussy was wet enough, but I was already at my maximum length, so it would definitely hurt. She did not take any breaks and just lowered herself until her butt was on me.

Me: ‘Why don’t you stand? I’ll do the work.’

She stood up with me and I turned her over to the seats, so she could rest her body on her arms. Once I tided her dress to cover up our interconnected genitals, I began moving gently at her, giving her time to accommodate my size. She groaned softly, while her pussy stretched and remained at that width as I pumped.

Soon, whispers of ‘faster’ came from her and I picked up speed, moving in small motions, keeping most of my shaft inside her. The virgin hole was definitely small and suffocating, but her attempts to relax paid off and I could last much longer. Although we were doing it in a public park, the high concrete backrest hid us well and any passer-by would be spotted before they could see us in the dim pavilion.

Thrusting faster, the petite girl was trying her best to keep quiet, but moans were still coming from her. In under five, another stream of wetness coated my balls and I knew she came. There was no change in tightness as she was already squeezing me so hard, and I just kept going. This was a time when minutes felt like hours, often suspecting that we had been spotted. She was already urging me to hurry, since it was getting late.

I listened to her commands and went in longer strokes, triggering an orgasm that lasted for the last lap of my race. With a non-stop flowing pussy, the extra lubrication was easing the strokes and I used it to my advantage, driving my rod so deep and hard into her that her knees had to rest on the seats instead of standing.

After another three minutes, my dick was screaming all the warnings into my head and I slowed down, enough to let her know that the delivery was arriving.

Her: ‘Shooting?’

Me: ‘Yeah.’

Her: ‘Take it out? I’ll help you shoot, just not inside me.’

I stepped away and she tapped on the wooden seats. I took my spot and she shifted away from me, lying her sides and facing my dick. She took my dick into her mouth and pressed her lips together, gracefully gliding her mouth up and down my rod. I laid back and enjoyed the view of the untrained girl sucking me off, until my load came knocking at the pee hole.

Me (whispering): ‘Shooting!’

She sank her mouth deep twice and held my hood between her lips, pumping with her hand for the last stroke. It finally came and I exploded into her mouth, giving me one of the most intense cumshot ever that kept my rod pumping despite being empty. Her mouth filled up quickly and she took another few trips along my shaft, before removing her mouth from my wasted rod.

Giving her lips a tongue lick (pushing a little of her tongue out between her lips), she gulped without a flinch of an eyelid and tucked herself into my arms after. A simple tug of my waistband hid my ‘childhood’ (cause the man had became small) and she raised one of her feet to the seat, hand disappearing under her dress.

Me: ‘Still horny?’

Her: ‘Just a little sore.’

We hugged for a while more without kissing once and she had to leave for home. A quick pat of her dress straightened everything and I picked up our belongings, ready to split for the night.

Her: ‘Thanks for tonight.’

Me: ‘I should be the one thanking you. I enjoyed myself a lot.’

Her: ‘Me too. Let me know when you want to meet again?’

Me: ‘Yupp.’

She reached into her bag and took her knickers out, giving her pussy a wipe in an unglamorous manner under her skirt and handed it to me.

Her: ‘Use it when she and I are not free to help you?’

I took it with thanks and we parted under the stars, leaving me a small gift which was made dirtier the moment I reached home, using the thoughts earlier to truly tire myself out for a good night’s sleep.

Her (Whatsapp): ‘I masturbated again thinking of you.’

Me (Whatsapp): ‘So did I. :)’

And that was how an underground relationship came about.

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