From Flashing to Fucking

The cool morning breeze hit my cheeks as I sprinted through the desolate streets of my town, which would've been packed with people and vehicles if I'd been there at noon instead of dawn.

My heart was racing with the effort, and sweat was glistening on my face like jewels. My muscles were straining but I kept pushing on.

That was when I rounded a curb and ran straight into someone racing towards me from the other side.

"Ow!" I yelped as I hit the road and the figure landed on top of me.

I was greeted by the wrinkly face of a middle-aged man nearing the dusk of his life.

"I'm sorry," he said in a deep fatherly voice, "Are you Ok?"

"I guess you could get off my breasts first..." I said, referring to his hands squeezing my boobs over my hoodie.

"Oh..." He blushed as he hastily got up to his feet and offered me a hand.

I took his hand and pulled myself up. He was almost 50, with a few strands of white hair and brown eyes. He was wearing a jacket and tights.

"Are you hurt?" He asked.

"I'm okay I guess... What about you?"

He simply nodded and eyed me up and down.

I noticed that he was looking at my grey hoodie, which had been dirtied due to the dirt on the road.

We stood there awkwardly before he introduced himself.

"Phil..." He extended a hand.

"Jessica..." We shook hands.

After a few more mutual apologies we started walking together and talking about ourselves. Basic stuff- education, family, hobbies etc.

I came to know that he was a manager in a local bank and had a family.

"My daughter's about as old as you..." He chuckled.

"How old is she?"

"19..."

"I'm 23..."

"Really? You look younger to me..." He said.

I blushed at his comment.

"Thank you," I said.

"You must have a lot of boys drooling after you..." He said. When I didn't respond, he hastily added, "Sorry that was a bit too personal..."

"I don't mind," I said, "But sadly, I'm a bit too fat to be considered attractive."

Although he was getting a bit too nosy, I was kind of enjoying the attention, which none of the jocks at college had spared me ever.

"Blokes these days have been watching too many of those models with fake tits on the internet. They can't appreciate real women..."

His rough mention of the word 'tits' created an awkward silence in the air but we continued walking.

"So? Are you exercising to impress those boys?"

"That's one of the reasons, yes..." I said, almost whispering.

"Is this your first day?" He asked

"Yes..."

"I've been jogging on these streets at this time daily for over four years. It's a refreshing experience but unfortunately I don't get company..."

"Well we could jog together from tomorrow..." I suggested.

"Wonderful!" He said almost a bit too excitedly.

Over the next few months, we got to know each other a lot better and developed a deep friendship. He started referring to me as "Jess", my nickname. He visited my home a couple of times after jogging for a cup of tea. During these winter months, I didn't ever consider engaging him sexually.

Even he didn't make any moves except the casual remarks about the prettiness of my blonde hair. Through our conversations I'd come to the conclusion that he was very devoted towards his family. I was sure that he could never cheat on his wife.

Gradually, the winter was coming to an end and I found it hard to jog in my woolen hoodie, and so I decided that it was time to break out my summer attire.

I thought that it would be a good surprise for Phil and I wanted to see how he would react.

I decided to go with a white sleeveless jersey and black shorts which covered my knees.

My perception of Phil was about to change that day.

As usual, I jogged to our meeting spot and waited for him there.

Soon enough, I saw his silhouette approaching me and pretended not to be aware of his arrival.

"Change in attire?" He said as he stopped next to me.

"Change in the weather..." I replied.

"You're right..." He said, wiping sweat off his brow as he opened the zip of his jacket, revealing a T-shirt beneath.

"Better..." He smiled.

We jogged as usual and I was far more comfortable today because of the change in clothing.

Even then, I was sweating profusely after the jog, and my white top was translucent due to being drenched.

Fortunately (or rather unfortunately) I was wearing a bra underneath, which concealed my nipples.

While walking me to my house, I noticed him stealing glances at my legs, which I'd waxed the day prior to avoid a fashion disaster.

"Nice legs Jess..." He commented, trying to sound polite.

"Why do you think so?"

"They're nicely toned and..."

"And?"

"They seem very smooth..."

"You like smooth legs?"

"I like groomed women who trim their body hair..."

I don't know why but this conversation was slightly arousing me.

"But I haven't shaved my armpits..." I said, my voice growing a bit huskier.

"Could you show me..." He said, slightly reluctant,

I lifted my arms above my head and we stopped walking.

"Well, the blonde hair is not too visible on your fair skin tone..." He said, "but you'd look better if you get rid of it..."

"I'll think about it..." I said as lowered my arms and we continued walking and reached my home.

"Tea?" I asked.

"Maybe tomorrow..." He said.

After I entered my house, I felt very horny recollecting his recent behavior. Commenting on my smooth legs and advising me to shave my armpits was something I hadn't expected from him.

There was no love in my life, and so an old man ogling me was turning me on instead of disgusting me.

I masturbated that night as I fantasized about going completely nude the next day.

Of course that wasn't going to happen.

But I did decide to make a couple of changes.

I went to the bathroom and waxed my armpits. I also decided to wear something a bit more revealing.

I decided to go with a green low cut top which exposed plenty cleavage. The thin fabric was straining to contain my mammaries. I considered going braless but that was a bit too much.

I also decided on black shorts which exposed my thighs and knees and stuck to my legs. I didn't wear any panties. I had realized that he had a slight fetish for curvy and chubby women. Although I'd lost a lot of fat over these months, I had a naturally chubby build which I had come to accept and admire. I also appreciated how my breasts had grown over these months for mysterious reasons.

As I greeted him the next day, he stared at me for a good 10 seconds and didn't even greet me.

"Are you alright Phil?"

"Yeah..." He said, still in a trance-like state, "You're looking beautiful Jess..."

"Thanks..." I said.

Even he had changed into his summer attire which consisted of a T-shirt and shorts. I was noticing a bulge in his shorts.

He wasn't focused on his pace as he usually was and got tired easily.

We soon started walking again.

"Tired already?" I asked.

"Your beauty knocked my breath out of me..."

"That's an advantage for me..." I chuckled and raised my arms above my head, pretending to do my hair. He started staring at my armpits. I turned my head towards him and smiled.

Normally, he'd steal side glances but today he was staring intently.

"You shaved your armpits!"

"I did it for you..." I said, encouraging him to make further remarks which were turning me on.

"That's really sweet of you!" He said.

I lowered my arms and my apartment came into view.

"Care to join me for tea?"

"Yes please..."

I liked how I was arousing him. Like an obedient pup he followed me into my apartment.

I lived in a small apartment that had a drawing room, a kitchen, a bedroom and a single bathroom.

He sat on a sofa while I made us two cups of tea.

I sat down next to him and we started chatting. Casually, he brought up the topic of my dress.

"Did you like my dress?" I asked.

"Absolutely..." He said, "I like the fact that you're gradually getting confident about your looks." I realized his other hand was casually resting next to my bare thighs. His fingers would lightly graze my smooth skin affectionately which caused my heart to beat faster. I sighed lightly.

"There's just one bummer..." He said.

"What?" I asked.

"Your bra is visible outside your top." He said matter-of-factly as he sipped his tea.

"Oh!" I glanced downwards. Indeed, my top was so low-cut that my bra was visible.

"What should I do?" I asked him.

"You could either wear a top with a less deep neckline or you could simply get rid of the bra..."

I liked where this was going. I casually kept my cup on the table and declared, "I choose the latter..."

With that, I reached for the bra clasps under my top but pretended that I couldn't reach it.

"Could you help me Phil?"

"Sure baby doll..." He said.

He had never referred to me as baby doll before and it excited me even further.

I turned my back towards him and awaited his touch.

I felt his warm fingers on my neck, which slowly slid downwards towards my back. His mere touch sent shivers throughout my body and I sucked in a deep breath.

"Are my fingers cold?" He asked.

"No... It's just...." I searched for words.

"Never mind..." He chuckled. He continued rubbing my back looking for my bra straps. I'm sure he must have been pretending, but I played along.

Finally I felt his fingers unclasp my bra. Slowly, he pulled it out of my dress and my boobs relaxed under my dress.

Suddenly I felt a bit self-conscious due to the sag in my breasts.

Nonetheless, I turned around and faced him.

"Is it better now?" I asked.

"Yes..." He muttered as he looked at the outline of my nipples protruding from under the thin fabric.

"There is still scope of improvement though..." He commented sincerely.

"What do you mean?" I asked.

With shaking hands, he reached for the sides of my top. A part of me wanted to stop him, to establish limits, but my hormones prevailed over my senses.

He held on to the arm-holes of my top and gave it a tug downwards. He applied a constant touch and soon I heard a tearing sound.

I noticed that the arm-holes in my dress were so wide that my side boobs spilled out of them.

"Better..." He smiled.

I smiled but said nothing. Sensing my approval, his hands again reached shakily, this time for the neck-hole. The top was already very low-cut, the deepest I had; but he apparently had plans to make it deeper.

He tugged at the neck-hole and the feeble fabric gave in to his forceful tugs and started tearing apart.

He tore it all the way down to just above my navel.

All my breasts were visible now except my nipples which were covered by the straps of the dress. The neck-hole wasn't even a neck-hole anymore.

I moaned with excitement.

Now he reached for my black shorts and started sliding them upwards. Remember I wasn't wearing any panties and was very wet due to the arousal. He slid it so high that my pubic hair would have been visible if I hadn't trimmed it.

Finally, he stopped and looked at me like I was some sort of a masterpiece(or a "masturpiece"?)

His hand was still on my thigh and he was stroking it continuously.

"What do you think Jess?"

"Wonderful ideas..." I said as I looked into his eyes. He still had that caring look, but I saw a tinge of lust in his eyes.

However, it was getting a bit too much. I bid him farewell for the day and he departed, beaming at me as he left.

I looked at myself in the mirror. My breasts were completely exposed except for my nipples, which were hard and were still visible under the thin strap. I was practically topless. My shorts had been rolled up higher than my panties and all my legs were exposed.

I was so horny that I masturbated at night imagining what the next day had in store. How far enough was I ready to go? It was clear that we had crossed a line. I had allowed him to feel me up and tear my clothes.

It was clear that my top was ruined and I'd have to wear something else tomorrow. I was kind of in a dilemma as this had been my deepest top and now I couldn't wear it.

That was when I had a wicked idea. I would expose even more of myself to him but also tease him a lot at the same time.

So the next morning I jogged to our meeting spot.

Phil was waiting for me eagerly but was disappointed to see me in my older hoodie and full pants. His disappointment was visible from several feet away.

"Good morning," I said, cheerful as always.

"Morning," he replied unenthusiastically.

"Ready to jog?" I asked, taunting him.

"Yes of course..." He replied.

We jogged for 2-3 kilometers as usual and started walking towards my house.

"I'm starting something new today..." I said.

"What?"

"I want to do some skipping, will you join me?" I said.

"Sure... I don't know how to skip though; so I'll watch and learn."

I admired the fact that he still had love for me. A guy who was only interested in abusing my holes wasn't my type.

We entered my house and I immediately fetched the skipping rope.

We cleared some space for me.

I took the rope and started skipping while he sat and looked at me.

After a couple jumps I said, "I'm sweating..." and pulled down the zip of my hoodie almost half-way.

His eyes lit up with excitement and a small smile spread across his lips as he noticed my bare flesh beneath the heavy hoodie.

"Keep going!" He cheered.

I was aware of my boobs bouncing naked and unhindered underneath my hoodie.

After a few seconds he said, "You're sweating heavily, why not get rid of this hoodie and continue?"

I didn't say anything but unzipped it all the way down.

My navel was visible and so were the inner sides of my boobs. The hoodie covered my nipples and side boob.

As I was jumping, I risked exposing my nipples but they stayed in.

I could notice that he had a huge bulge beneath his shorts as he continued to stare gleefully.

Finally I got tired and stopped jumping.

I flopped down on the sofa next to him but made no attempts to zip it up.

"How was I?" I asked.

"Wonderful!" He said.

"And that's a wonderful way to dress!" He said.

"Thank you!"

"It's sexier than what I'd proposed." He said.

His finger reached for my chest and wiped a drop of sweat from the middle of my breasts. I quivered at his touch.

"It's a shame that it hides your arms though..." He said.

"I'll see what I can improve." I said.

He said goodbye and left with an erection.

It was time to take things to the final level; I wanted him to fuck me.

I rummaged through my closet and found my final weapon.

It was a sleeveless cropped jacket which was meant to be worn over other clothing. I had other plans however.

I put it on over my naked body and looked at myself in the mirror. Indeed I was quite exposed. My arms were visible and so was my stomach. Then I made a few changes...

I managed to break its zip and tossed it in the bin. Then I tugged at the arm-holes and pulled them down so deep that my side-boob was clearly visible.

I twirled and looked at myself from all angles. I looked ready to be fucked. My upper body was completely exposed except for my nipples and back.

I got creative for my lower. I put on a thin string on my naked belly. Then I took two handkerchiefs. I tugged both of them in the string- at the front and back. The one in the front barely covered my pussy while the other one covered my ass. However, a bit of my crack was still visible. The string was so weak that it could break at the slightest tug and I'd be naked from the bottom down. From the sides I was virtually naked head to toe. I was ready...

The next day I jogged up to our spot and found Phil waiting for me.

He opened his mouth wide and mouthed a 'wow!'

We jogged as usual and I stole glances at the old man who now had raw lust in his eyes. His eyes were focused on my ass swaying beneath the handkerchief.

As we slowed down to walk, I initiated the conversation.

"So, how's the new style?" I asked.

"You look like... an angel..." He said, awestruck.

As my house came into view, I asked, "Care for some extra exercise?"

"Of course!" He said and followed me inside.

I shut the door behind us and declared that I was interested in some stretching.

"Will you help me?"

"Yes babe..." He said.

He stood behind me and lifted my hands.

"Stretch your toes and inhale..." He said.

As I inhaled, he slid his hands down my arms and rested them on my armpits. He started rubbing my armpits and whispered, "exhale..."

I could feel his hard cock against my ass.

He lowered his hands further and touched my boobs from the side.

"Inhale again and let me feel your lung capacity..."

As I inhaled he put his hands just inches above my naked nipples.

"I can't judge your lung capacity due to this jacket..." He said.

I didn't say a word but reached for my jacket and removed it.

The jacket was on the floor now, and his cock grew harder. He still couldn't see my nipples but I knew he was dying to.

"Let's try this again..." I inhaled and he placed his hands on my breasts above my nipples.

His hands moved up and down with my breasts as I continued inhaling and exhaling.

I was so wet that my fluids flowed down the inner sides of my legs and reached the floor. I was dripping my pussy juices like a tap that hasn't been properly closed.

He now brought his hands under my breasts and cupped them.

"You are beautiful Jess..." He whispered as he squeezed one tit.

I was dying for him to graze my nipple but he continued teasing me.

A drop of sweat fell down on his hands.

"You're sweating!" He said and pulled the handkerchief on the back. This tug was sufficient to break the string and the one on the front fell down on the floor.

I was now completely naked except for my sports shoes and socks.

He brought the hanky and wiped my forehead. He then wiped my breasts and I moaned.

It was then that he noticed my pussy juices dripping on the floor.

"Oh! Is that sweat?" He whispered as he brought the hanky down and started wiping my pussy lips. He then brought it up to his nose and sniffed it, "Smells better than sweat..."

He dropped the hanky and brought one of his hands down to my pussy.

Slowly he started rubbing my inner thighs circling around my pussy.

With his other hand, he suddenly pinched my nipple.

"I've wanted you for so long babe!" He whispered seductively.

I simply continued moaning.

That was when his finger suddenly touched my clitoris and I moaned even louder.

"Your body is so smooth, soft and chubby, just the way I like..." He said as he started rubbing my clit vigorously. "You're so wet..."

"I want you to fuck me daddy!"

"That I will..." He said as he squeezed my tits harder.

"I want to plant my seed inside you and fill your soft tits with milk. When they'll get milky I'll love to suck them dry. And your armpits are so fragrant..."

His words turned me on more.

I felt a torrent of juices inside me as I moaned, "Oh my God!" I screamed as I squirted all over his hand.

I heard him lick his fingers.

"Delicious!"

Finally he turned me around and locked his lips with mine. He held my cheek with one hand and a breast in another.

I reached down and squeezed his erection with my hand. I could feel a damp spot on it.

Daddy lifted me in his strong arms and lay me down on my back on the sofa.

He bent over and kissed my pussy lips. I sighed.

Finally he took off his T-shirt.

He had a slim body with a little body hair. The wrinkles of old age were slightly visible on his chest and neck.

"Does baby girl want this?" He said, pointing to his erection.

"Yess..." I hissed.

"Have it then..." He said and dropped his shorts to the floor. Surprisingly, he didn't have any boxers on. I took in the sight of a wrinkly dick that was very thick and veiny and over 6 inches long. His balls were huge and sagged due to age.