August 2000 Ch. 01

Story Info
Tutoring Mary's brother.
2.1k words
4.6
141.2k
35

Part 1 of the 6 part series

Updated 10/09/2022
Created 12/29/2003
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

What I’m about to tell you happened three years ago, toward the end of the summer of 2000. I was back at home after my first year at college. I worked a few hours each week at my dad’s office, but spent most of the time at the beach or at the pool at my girlfriend’s house. At the beginning of the summer, I had met Mary, a very sweet, very pretty girl. She worked for my dad in the accounts department and I met her my first day at work. She had been reluctant to date the boss’s son, but after a week or so of pestering her to go out with me, she agreed. It had been a wonderful summer. Most evenings, when she finished work, we drove the few miles to the local beach, and stayed there until dusk. I loved lying next to her on the beach, looking at her body and her pretty smile, getting more and more horny thinking about making love with her later in the evening.

I had spent so much time with Mary at her house that summer I had become very friendly with her family. Her parents were a nice couple, and her brother Mark, two years younger than Mary, was a good kid. When I told Mary’s parents I was studying math at college, they asked me if I would give Mark some math tutoring. Of course I agreed, and even turned down their offer to pay me (I guess I felt indebted to them for ignoring the fact that I fucked their daughter in their house most nights). So I spent a few hours a week working on math with Mark, usually on the two evenings Mary had classes at the local college. We’d spend an hour or two working on math, and I’d have dinner with Mark and his parents, then go meet Mary after her class.

I should tell you now what’s at the heart of this story: Mary and Mark looked alike. Let me describe Mary. She was blond, and had deep brown eyes. She had a pretty face, and a radiant smile. I loved her shoulders, and I could write poems about her tiny breasts -- I had only to picture them for a wave of pleasure to sweep through my body. Even now, three years later, I can vividly picture how her slim waist flowed out towards her hips and ass. How I loved that ass! Every opportunity I had, I walked behind her to watch her ass. She knew the effect her ass had on me: she would run up stairs ahead of me and look back to make sure I was watching her ass. Half way through the summer I bought her a black thong bikini. Buying it, I had been worried that she might think it too slutty. But no. I gave it to her on the beach one evening, and she looked at it, then, in plain view of anyone who might have been watching, took off the bikini she was wearing and put on the one I had given her. As I remember her undressing on the beach, I still get so excited. Let me finish my description: Mary’s legs were toned from her running, and as the summer progressed her body took on a golden glow from the hours we spent in the sun. She was beautiful, and sweet, and over the course of the summer I had fallen deeply for her.

Your probably see where this is leading. Mark, too, was blond, and his hair was long like Mary’s. He too was slim, and tanned. But, perhaps most of all, he had his sister’s smile. I hadn’t realized that at first -- perhaps he didn’t smile much when we were working together on math problems. But, at some point during the summer -- I don’t now recall when -- he had smiled his sister’s smile at me, and I had seen the resemblance. I saw it first in an abstract, theoretical way -- my, don’t they look alike. That was to change.

I’ll move my story along, for I know that I’m too much inclined towards scene-setting, and too slow to get to the point.

What you have foreseen happened on a hot August evening, two weeks before the summer was to end and I was to return to college. Mary was in class, and her parents were out of town visiting relatives in New Hampshire, or Vermont, or some such place – it doesn’t matter where. Mark and I had spent a couple of hours going over some math problems, and I was tired from the mental effort and the heat. When we had finished working, I took a dip in the pool, and came back inside with a towel wrapped around me. I sprawled on the couch and watched some television. Mark stretched out on the floor in front of me, also tired from the math. Whatever program was on, it didn’t hold my attention. I was thinking about Mary, and making love to her in her bedroom later that night. My gaze had rested on Mark’s legs. It struck me that they looked just like Mary’s -- slim, and tanned. My eyes moved up over body, and I imagined I could see his waist, his chest, and his shoulders though his shorts and t-shirt. Whether it was the heat, or my tiredness, I started to imagine it was Mary stretched out before me, and my anticipation of her undressing for me in her bedroom grew more acute. My cock grew under the towel as I thought about how Mary would turn away from me and slowly slide her panties down over her beautiful ass.

I don’t know how long I had been staring at Mark as my cock got stiff, but at some point I realized that he was looking back at me over his shoulder, smiling his sister’s smile.

“What are you thinking?,” he asked.

His question broke my reverie, and I was at once aware that I had been staring at him and that my cock was erect, and clearly so. I shuffled my body to try to disguise my erection.

“Nothing,” I replied. Then: “I was just thinking how much you look like your sister.”

Mark smiled back at me, not saying anything. I couldn’t meet his glance, and pretended to watch the television. After a couple of minutes, he stood up, and left the room.

I sat there a few more minutes, my cock and my embarrassment slowly subsiding. I should get up, I thought, and go meet Mary. A few more minutes, I told myself. Then Mark spoke from outside the room.

“Turn off the television and close your eyes.”

“Why?”

“I have a surprise for you.”

I reached for the remote and turned off the television.

“Now close your eyes.”

“Ok, they’re closed.”

I heard him walk into the room.

“Ok, you can open your eyes.”

I looked up. Mary was standing a few feet in front of the couch where I was sprawling. She was wearing her black leather miniskirt and her white silk blouse, through which I could see the outline of a black bra. Her blond hair was pulled back behind her ears, and her lips were red and her eyes made up. On her feet were the short white tennis socks that, at my pleading, were the only clothes she kept on when we made love.

Of course I knew it wasn’t Mary, and if I had had time to collect my thoughts, perhaps things would have been different. But, maybe, things would have turned out the same even had I thought about it.

“So, what do you think?,” he asked.

“Amazing,” I muttered, “really amazing.”

He twirled around so I could see his ass tight in his sister’s miniskirt, and he lifted his arms above his head to accentuate his slim waist. Then he stood still, looking at me with that irresistible smile.

“What if I were Mary?” he asked.

“What do you mean?”

“You know. If I were Mary, what would you do?”

I looked at him for what seemed to me a long time. It might have appeared that I was thinking about my answer. In reality there was no thought going on. Rather, as I looked at him, the inevitability of my response was swelling inside me. I stood up and stepped toward him. My hands reached up and gently drew his face towards mine, and I kissed him softly on the lips. His eyes closed as our lips met. I kissed him again, this time our tongues touching. His eyes opened and met mine, and he smiled at me. “Pretend I’m Mary,” he whispered. My hands slid down to his waist, and I drew his body against mine, and we kissed again, deeper than before.

“Undress for me,” I said. He started to unbutton Mary’s blouse. I watched avidly as each undone button revealed more of his smooth chest. He slipped the blouse from his shoulders, and stood there looking at me. I recognized the bra as the top of the bikini I had bought Mary, and my cock grew harder as I realized what he had on under Mary’s skirt.

Mark turned away from me, and undid the clasp on the skirt. As he released the skirt to fall to the floor, he leaned over so that his ass, dressed only in Mary’s black thong, was toward me. He turned back me and my hands went round his naked waist, and pulled him to me, only Mary’s thong and the towel around my waist separating our bodies. I reached around his back and unclasped the top of the bikini, and my mouth moved from his lips to his nipples. He sighed, as Mary did when I sucked her nipples, and with that sigh I was lost. I lead Mark to the couch, and he sat down facing me. I kneeled between his legs and reached up for his panties. Slowly I pulled them down over his cock. His cock pointed up at my face, and, as though I had done this before, I leaned over to take him in my mouth. Do I have to describe what it was like? I couldn’t begin to do justice to the sublime taste and feel of that hard, warm cock in my mouth, to its smoothness as I ran my tongue over it, to the sound of Mark’s breathing as I sucked him, my hand now between his legs, rubbing his balls. As I sucked his cock, I had a vivid picture of him lying back on the couch, naked except for the Mary's little white socks, with his legs spread, and me between them, and that image excited me even more.

I took the towel from around my waist, freeing my cock, which I stroked as I sucked my girlfriend’s brother’s cock. With a loud moan, Mark’s body tensed as he came. I felt his cum shoot into my mouth, and I ran my tongue around his cock, licking his cum against it. I stayed kneeling there between his legs, caressing his cock with my tongue as it softened and his body relaxed.

I let his cock slip from my mouth and sat back to look at him sprawled on the couch. I took in his long tanned legs stretched out towards me, his sister’s black thong still around his ankle; his cock, glistening with his cum, and his small, tight balls; his slim waist, and his delicious red nipples; and his face with that amazing smile. Our eyes met, and we looked at each other, neither speaking. My hand moved back to my cock and I masturbated as Mark watched me. He slid off the couch and sat in front of me, his face close to mine. He kissed me, and his hand slipped between my legs, and I gasped as he touched my balls as I rubbed my cock faster and harder. As my excitement built, his finger moved further back to explore my ass. I gasped, as I did when Mary fucked my ass with her finger. He pushed his finger into my ass, at the same time kissing me again. I came at once, so hard, shooting streams of cum over his chest.

We sat there silently. I watched my cum slip down over his stomach to his cock. “Lie down,” I said. As he sprawled on his back, I traced the line of my cum with my tongue, down to his cock, which started to harden again as my lips slipped over it.

“No,” Mark said. “Not now. You’re going to be late for Mary.”

I stood up and dressed. Mark, still naked except for Mary's socks, walked with me to the door. Just before I opened the door, we kissed again. Mark whispered in my ear, “Next time, I want you to fuck me like you fuck my sister.”

“Yes,” I replied.

TO BE CONTNUED.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
smoothed273smoothed273about 1 year ago

👍👍💖💖💋💋💋

AnonymousAnonymousover 13 years ago

dude thats hot!!!!!

Bridget69Bridget69almost 19 years ago
As hot...

as a late summer's day.

AnonymousAnonymousalmost 20 years ago
Wish I were Mark

I can imagine being Mark in that story and can only hope you write a sequel where Mark gets what I would want in the situation

AnonymousAnonymousover 20 years ago
Give Mark some DICK!!!

My prick got HARD reading this story, as well as, fantancizing about it. Give me some MORE!!!

Show More
Share this Story

READ MORE OF THIS SERIES

August Series Info

Similar Stories

My Big Sister His older sister has a few surprises.in Transgender & Crossdressers
Sweet, Young Stephanie Delicious girl next door has a big surprise.in Transgender & Crossdressers
My Brother's Panties A twin finds himself drawn to his transexual brother.in Transgender & Crossdressers
His Teacher, The Transsexual A young man ends up very close to a teacher with a secret.in Transgender & Crossdressers
The Babysitter's Secret The pretty 18-year-old sitter has a special surprise.in Transgender & Crossdressers
More Stories