Anal

My name is Mike Martin. I’m 21 years old, 5′ 8″ tall and weigh 127 pounds. I have blue eyes and blonde hair I like to wear long. And I’m gay. I’ve known I was gay since I was 10 years old. I live in a small town in Missouri with my mother, a single mom. I never met my dad. Mom knows I’m gay, but nobody else does. I’ve always been too shy to tell any school friends. Obviously I’ve never hand any experience sexually with anyone, male or female. I do enjoy a, let’s say, healthy fantasy life.

When I was 16 I began working part-time at ‘Winslow’s’, a local store that had been in the same family for generations. Don Winslow, “Old Man Winslow” to the kids in town, ran the store now as his father and grandfather had before him. Mr. Winslow was about 60, slim, with graying black hair. He had never married, and never dated, to my knowledge. Some people in town whispered that Mr. Winslow was gay. I sometimes wonder if that’s why I applied for a job at the store back when I was in high school.

In a small town like ours, a good local store can be a life’s blood. The nearest chain store was over 50 miles away, the nearest shopping mall nearly 100. Winslow’s had grown and expanded over the years to provide nearly every thing our quiet little town needed. Clothing, dry goods, housewares, all found a place on our crowded shelves.

When I was first hired at the store I stocked shelves, swept up, and performed general duties. After graduating from high school, I was brought on full-time and was trained in all aspects of running the store. Mr. Winslow treated me as his protégé, and my responsibility grew as I learned. I had become quite fond of my boss, and feared I was developing a crush on him. I never said anything, worried that I would do or say something that would ruin our growing friendship. Mom said I had “daddy issues”. It was hard to disagree.

Today was the end of the fiscal year, time to do a complete inventory and close the books. Mr. Winslow dreaded doing the inventory as he’d been doing it for most of his life. I, on the other hand, enjoyed it immensely. We’d close the store early, and spend the evening together. We’d compare the shelf stock to our lists, remove items that weren’t selling, and introduce new items we thought would sell. It was the perfect chance for a fresh start, a new beginning.

Mr. Winslow came out of the back room carrying the inventory sheets.

“Ready to start the inventory Michael?”

“Yes sir, Mr. Winslow! Whenever you’re ready!”

Don Winslow sighed. “Don. I’ve asked you to call me ‘Don’ a hundred times!”

“Yes sir, Mr. Winslow. Whatever you want!”

I smiled as I walked over to lock the door. This was sort of a running gag between us. He had asked me to call him ‘Don’ years ago, but I just couldn’t seem to do it. I turned the old style key in the ancient lock and hung it on a hook by the door. I placed a sign in the window that was hand inked and considerably older than I. It said cheerfully ‘Closed for inventory – See you tomorrow!’. Everyone in town knew what this sign meant and we would be undisturbed.

Mr. Winslow placed a cd player on the counter and loaded it with his favorite cds. He had a preference for 60s rock music, something I had grown to love also. Working casino oyna together, we quickly flew around the store comparing our expected inventory to our shelf stock to the sounds of the Beatles, the Beach Boys, Cream and the Kinks. After just a couple of hours we had inventoried the entire floor.

“Well, that was fast!” Mr. Winslow looked pleased. “That used to take me all night when I had to do it alone. We make a good team, you and I. Let’s get started on the stockroom, and we’ll take a dinner break.”

We moved our music into the back room and set up there. Mr. Winslow stood there with his hands on his hips and looked around.

“I suppose I should get started on the shelves. Michael, why don’t you open the boxes of new inventory on the back wall and try to put them in some semblance of order?”

I began opening boxes and separating the merchandise by type and color. Opening one box I was surprised to find several pairs of lacy ladies underwear. Very sexy lacy ladies underwear. Not the kind of thing we usually carried in stock. I ran my fingers over the soft material. Black lace panties with a tiny thong backside. I looked over my shoulder at Mr. Winslow. He was humming along with the music and counting shirts on the shelves. I held the panties up in front of me and cleared my throat.

“Ahem. When did we start carrying these?”

Mr. Winslow looked over and saw me waving the panties back and forth, wiggling my eyebrows suggestively. He let out a small laugh.

“Those were a special request by Mrs. Foster. You know her, the newlywed? She wanted something more, erotic, than our usual fare. There should be a few more things in there. Im not sure if she’s trying to keep her husband interested, or kill him” he said with a chuckle.

“She definitely has the figure for it” I relied. “I bet she’d look incredible in these!”

“I think you’d look incredible in those.”

He had said it so softly I almost didn’t hear it. As it was, I couldn’t believe the words had come out of his mouth. My jaw dropped, and I gasped. Mr Winslow looked over at me, saw the shock on my face, and blanched.

“Oh my God! I can’t believe I said that! Michael, I’m so sorry! Please forgive me!”

“It’s ok.”

“I shouldn’t have said that. That was wrong. Please don’t hate me!”

Hate him? I looked at the face of this man, this dear dear man, now red with shame. All I wanted to do was take him in my arms and hold him. But I was frozen in my spot.

“It’s ok.”

“No, its not. I’m sorry…..you should go home. I’ll still pay you….”

“IT’S OK!”

He looked at me. I smiled.

“Really?”

“Really.”

He seemed to calm a little. The music had ended and the room was quiet. I could hear his ragged breathing.

“DINNER! I promised you dinner! I’ll run down to the diner. Hamburgers ok?”

“Hamburgers are fine. You go on now. I’ll keep working here.”

Mr. Winslow looked so relieved. He grabbed his jacket and headed for the door.

“Back in a jif!”

I continued unpacking the boxes. Besides the panties there were several other pieces of sexy lingerie. Bras, teddies, stockings, and pantyhose, all in black. I set the panties to the side. I held of the bra in front of me slot oyna and looked in the mirror on the wall. The bra was lovely, but I didn’t have the chest for it. I dropped it back in the box and pulled out a silky black teddy top. Leafing through the box I found a pair of sheer black pull up stockings that would stay up without garters. I put these aside with the panties and began undressing.

When I was completely naked, I looked in the mirror. Not too impressive. Leaning against the wall, I slid one silky stocking up my right leg. It felt cool and smooth. I had never worn ladies garments before and this was a new, exciting feeling. I put on the second stocking, then slid the teddy over my head. I looked at my reflection in the mirror. Better. I saw my penis begin to swell with excitement.

Finally I slid the panties up my legs and stuffed my stiff cock inside. I glanced over my shoulder at my reflection and saw the thong framing my ass cheeks. Yes, that’s what I was going for. I padded over to the shoe shelf. I wore a men’s size 8 shoe, so I selected a ladies size 7, black, with 3″ heels. I stepped into them, and practiced walking in them. Ready for Mr. Winslow’s return, I continued the inventory.

A few minutes later, I heard the front door unlocked, opened, and locked again. Mr. Winslow’s footsteps echoed in the empty store as he walked to the back room. I heard him walk into the storeroom, stop, and gasp. The bags he was carrying slipped from his fingers and fell to the floor. I didn’t turn around. I let him look as long as he wanted. A full minute passed before he spoke.

“Michael?”

“Oh. Welcome back Mr. Winslow. Well, what do you think? Do I look…..incredible?”

“Yes…you look…..perfect” he practically whispered.

I heard his footsteps crossing the room. I sensed, rather than felt him, as he came right up behind me. I leaned slightly backwards and felt his warm breath on the back of my neck. Taking a half step back my body came in contact with his. His hard cock strained against the front of his pants, poking against my naked ass cheeks in the thong. His arms came up and wrapped around my waist. I sighed, and leaned my head back on his shoulder.

“I just wanted to look pretty for you” I whispered. “I just want to make you happy.”

He moaned, and kissed my neck. His left hand slid up my chest under my teddy and brushed across my nipple. His right slid down across my stomach and pulled down the front of my panties, freeing my throbbing cock. He took my hard member gently in his hand and stroked it. Now it was my turn to moan.

I turned to face him. In my heels we were about the same height. I wrapped my hands around his neck. He cupped ny ass in his hands and lifted me to his mouth. Our lips met and we both moaned. We kissed hungrily, holding each other tightly. He finally put me down, and we stared into each others eyes, gasping for breath.

“What now?” he whispered.

I kissed him gently on the lips. “I want you. Do you want me?”

“Oh yes!” he moaned.

“Let’s go to your office……”

I turned on my high heels and clipped out of the storeroom. Mr. Winslow followed, his eyes glued to my swaying ass. I stopped in the pharmaceutical section and grabbed a tube canlı casino siteleri of lubricant. We walked into his office and straight to his couch. I knew it had a pullout bed in it for late nights or quick naps. We pulled it open.

I turned back to him and took him in my arms again. I sighed and rested my head on his chest as his hands roamed all over my body. I pulled away, and began unbuttoning his shirt. I ran my hands across his hairy chest and kissed his nipples. I unbuckled his belt and lowered his zipper. I dropped to my knees, and in one motion, pulled his pants and underpants down to his ankles. I slid his shoes and socks off and he stepped out of his pants. He stood before me, stark naked, his hard cock pointing at me and dripping.

I stood up and gazed at him in all his glory. He seemed embarrassed and held his hands over his slightly flabby stomach.

“I’m sorry I dont have a better body for you.” he mumbled.

“Don’t be silly. I’ve never seen anything sexier in my entire life. I’ve been dreaming about this for years.”

He took me in his arms with a tear in his eye.

“Me too baby, me too.”

I pushed him back onto the bed and he laid down. I pulled the teddy over my head, and slid my panties to the floor. Taking a handful of the lube, I gently stroked his cock and balls until they were nice and slick. I squirted a substantial amount onto his hand and asked him to lube me. I lay next to him on the bed and he slid a greasy finger in my asshole and slid it around until I was covered. He worked 2 fingers into me, then 3, until I was ready for his cock.

I pushed him back down on the bed and straddled him, one stocking clad leg on either side of his hips. Taking his cock in my hand I placed it against my hole and eased down on it. It hurt a lot, at first, but I took a deep breath and relaxed. He was very gentle with me and didn’t force it. I moved slowly, easing the tip of his cock into me a bit at a time. First a half inch, then an inch, then 2 inches. We rocked gently together in perfect rhythm. I started to feel really good! I began to rock harder and suddenly I slid all the way down on the length of his cock and he was inside me. He pulled my mouth to his and we kissed sweatily as he fucked my ass harder and harder. I began to moan loudly as my stomach and ass began to clench. I threw my head back and groaned loudly, then came in the most intense orgasm I’d ever felt in my life. I shot sperm all over his face and chest as my entire body shook. He stopped and stared at me in wonder as I came. I looked down at him.

“Why did you stop baby? I don’t want you to stop! I want you to fuck me silly!”

With a grin he began sliding his cock in and out of me again. Damn! It still felt so good! A couple of more minutes and he began to grunt.

“I’m coming……should I pull out?”

“No honey! Fuck me! I want to feel you cum inside me!”

He began moaning and bucking and suddenly, like a dam broke, he came. He filled me with his cum until I overflowed, his excess spilling out of me ans coating the sheets. I slid off of him and we snuggled together, his arm around my shoulder, my head on his chest. We were silent except for our heavy breathing which gradually eased. He finally broke the silence.

“This was the greatest night of my life.”

I smiled.

“Mine too Mr. Winslow.”

“Don! After what we just did you better call me Don!”

“Yes, sir, Mr………Don.

(: 🙂

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