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24
Sissy has an early morning escapade while jogging.
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I just moved to this new town. It's smaller and outside the city. I work remote from home each day, so I thought why not get out of the city and into the suburbs where it's cheaper?

My work provides a lot of time at home for me to dress up when the urge arises, which is often. No zoom meetings means I can really work on my hair, makeup, and outfits in the privacy of my apartment with only my cat to judge, lol.

Lately I've started jogging in the early morning hours, around 5am usually. It helps keep my small frame and I enjoy the cool and dark mornings. Most of the time I'm still in boy clothes when I go out, but the past few mornings I've gotten a little brave and started wearing a sports bra under my shirt or a pair of my satin panties under my shorts.

Around the corner from my apartment is a small college and they have a running track there. I feel safe running there and usually I'm there alone, save for the odd person out exercising as well. There has been a new guy recently though...an older gentlemen, maybe late 40s or early 50s, he has a little bit of the salt and pepper in his hair and he doesn't run all that fast. I've past him once or twice coming from or going to the track. I smiled and waved hello, he is a very handsome man.

Once, as we were passing, I caught him checking me out from behind and he quickly turned his head away and pretended to be looking at something else. At least I think that means he's into femine looking and sounding guys in their early 20s.

I went out the other morning hoping he'd be out there as well. I shaved my legs the night before, as well as the rest of my body hair. I put on my shortest running shorts and wore a sports bra under my shirt. If he was there, I was going to casually take off my shirt and see if there was any reaction. Just as I has hoped, he was there, doing his usual half jog and focused breathing. I pretended to stretch and warm up and just as he was coming around the turn, I lifted my shirt over my head and exposed my femine figure in the sports bra.

It definitely got his attention. His eyes widened and he gazed at me longer than normal. I just shyly smiled and gave him a little wave. He kept jogging. I did my usual run and without speaking to each other anymore, we both went our separate ways. There were more than a few glances sent between us while working out and I was so worked up when I got home, it was all I could do to not stop thinking about his muscular arms and legs, his mature face and subtle beard. I spent the day imagning all different encounters and fun things between us.

That night, I formulated a plan, and set things in motion for the next day. When morning came, I jumped out of bed. I took a shower and shaved my entire body smooth again. I rubbed lavendar and rose lotion over my smooth skin and misted myself with floral body spray. I put on a light covering of makeup...well, I thought it was light. I guess I have been practicing my club girl look a little much, so I went a bit heavy on the eye shadow and lip gloss. I pulled my wig out of the closet and tied it up into a pony tail and got dressed. A pair of pink short running shorts and a white crop top. Underneath I wore a pair of black lace panties and a black lace bra to match.

Completely impractical for running, but I had no intention of that kind of workout today anyway.

I strolled out in the early morning cool air. It was still dark and still would be for an hour or two. I made it to the track and I could hear him there, his familiar jogging pace made me excited for what might come. As I walked through the gate our eyes met and he stopped in his tracks. He just stood there for a second, looking at me, and I gave him the same shy smile and gentle wave as I did yesterday.

This seemed to encourage him as he made his way toward me. He was a little sweaty and still breathing heavily. I could feel his body heat the closer he got to me and I could smell his musky sweat. "Hi there" he said in a deep low voice. "Hi" I replied in my most soft femine voice I could manage. "Lovely morning" he said. "It is" I replied. "You aren't usually so dressed up for your run" he said to me. I smiled and hid my face a little "no, no I'm not. But I thought today might be different."

I tried to tilt my head, play with my hair a little, stand with my legs crossed... all the things I've seen nervous girls do when talking to a guy they liked. As our conversation continued, these physical cues must have worked because he slowly started standing closer and closer to me, until we weren't more than inches apart. "Might I say...you smell amazing" the gnetleman told me. "I like your smell as well" I told him in return. And with that he leaned in next to me, pressing his hips into mine and putting one of his hands around my waist. He pulled me closer into him and his face leaned into the side of my face and I felt his breath on my neck.

"Oh" I breathed and my body trembled. His sweaty chest was against my smooth skin and his warm body seemed to heat up my core. I found one of my hands balancing myself by touching his thigh. His other hand reached around and grabbed my ass. "Oh" I let out again and my other hand found its way to high tight abdomen. He continued to smell me and breath on my neck, as if he was trying to devour me. His face turn up and then he pressed his lips into mine, his hands still on my lower back and ass, he pulled me closer until our lips were firm against each other. I felt the pressure of his hips pressing into mine and then the hard bulge in his shorts poking against my pelvis.

I instinctively reached my hand in his shorts and took hold of his hot cock. I felt him grown harder in my hand and his breathing quickened as he kissed me harder. Then I felt his hand leave my ass and it settle on my shoulder. He pressed down and I took the cue to slowly fall to my knees. Once there, I reached up to pull down his shorts. His cock sprang free from his boxers and the hot sweaty smell of his stiff flesh ran over my face. I leaned forward and he pressed the head to my lips. I opened my mouth and he slowly slid it over my tongue and in my mouth. It was hot and hard and his course black pubic hair brushed against my soft cheecks and lips as he slowly fucked my mouth. I fondled his balls slightly and let my other hand squeeze his hairy ass. His fingers slipped through my hair and his hands were placed firmly on either side of my head, rythmically pulling my head up and down his hard shaft as my tongue washed over his cock. The pace increased and his thrusts grew harder. His grip on my head tightened and he let out a groan as he thrust hard. I felt the hot pulse of his cum enter my mouth and his cock throbbed between my lips as he continue to cum in my mouth.

When his grip looseded and I felt his body lose tension, I held his cock in my mouth and swallowed his cum down my throat. His legs trembled slightly and I felt his entire body relax. I pulled my head away from his cock and whipped the dribble of spit from the side of my face that had eaked out during the session. I composed myself for a second and then rose to my feet. As I did he pulled up his shorts and I brushed my fingers through my hair to set it back in place. He smiled at me with a sigh of relief across his face. "I have wanted to do that for weeks" he said. "It was all my pleasure" I replied with a shy smile. "Until we meet again my dear" he said as he began to walk past me. "Until we meet again" I said.

And as the sun had just began to come over the horizon, I picked up my water bottle and turned to head home. I had already started planning what to wear at our next encounter.

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1 month ago