Tag: Fantasy

“Well,” she asked, looking over her shoulder at me. “You coming upstairs?”
Emily had slipped the fuzzy robe off of her shoulders, and as it slid to her ankles, it revealed a tall, fit middle aged brunette woman, her skin toned dark from the shadows of the stairwell that she stood within, her legs tall and slender, her lovely ass even more shadowed and mysterious. Her hair was dark, and her eyes glinted in the low light. I noticed her tongue lightly emerging and licking her upper lip as she grinned at me.
I stood up, in shock. Definitely not what I was expecting.
Working my way through college, I had accepted a few babysitting gigs here and there, mostly from members of a community writing club that I had joined down at the YMCA, and from a few other couples that saw my advertisement, placed on the bulletin board in the YMCA lobby. I know it sounds a little odd for a 19 year old college junior, a male, with classes, intermural sports, fraternity hazing, campus parties, and all of the other distractions of collegiate life, to make some extra scratch as a babysitter. However, it was a good gig for me, since I usually could count on the last few hours to do homework, and didn’t mind if things went late. That endeared me with several couples who appreciated a sitter that didn’t turn into a pumpkin at 11. Hey, ten bucks and hour, and feel free to stay out all night while your kids sleep and I plug away at homework. Talk about a win/win.
Emily was a single mom, I think late 30’s, with a ten year old boy named Jacob. He was a fun, eager kid who loved to play board games and talk Star Trek with me, and it was more like having an annoying little brother than me being an actual babysitter. Emily hired me about once a month, and usually went out and came back from her dates, or wherever she went (I never was nosy about that) fairly early, by midnight. It had been highly regularly until tonight, formal. She was nice, kind of aloof, and seemed very motherly, in that she smiled and seemed to appreciate Jacob’s enthusiasm whenever I showed up.
Tonight she had dressed a little sluttier than before, a short blue cocktail dress that showed off her small perky breasts, clearly not fettered by a bra- and I saw no panty lines on her gorgeous aerobics-shaped ass. I tried not to stare, but it was hard not to as she explained what was in the fridge for food, and that she was probably going to be late. I think she caught me looking at her, because she gave me a wry look. “That all okay?” she asked. “Mmm hmmm.” I nodded. “Got it. Jacob in bed by 9. Casserole in the oven at 630, 45 minutes at 375. You might be late.”
She smiled warmly. “You pay attention handsomely. And such a cute young boy.”
I looked chagrined. The last thing a 19 year old college boy wants to hear from a hot woman is that he is “cute.”
“What are you doing?” I asked. “You look very nice tonight.”
“Thank you, Jay,” she said. “I’m going out with some of my girlfriends. And there is talk of a mysterious party later, which is why I might or might not be late tonight.”
“Be as late as you want,” I said. “If you’re not back by morning, I’ll send out a rescue party.”
She giggled. “No chance of that.” She gathered up her purse and keys and slid out of the house, while I covertly watched her fine long legs, and ass bouncing a bit in her tight dress.
Standard package of babysitting: Jacob and I watched a movie, hung out, and ate. I got him in bed by 9, and hunkered down at the kitchen table with text books open, and began working on an Aristotle essay. Time zipped by pretty quickly, and I was in good cheer, feeling like I was being paid to write my homework. I glanced up at the clock at one point and noted that it was almost midnight. I got up and peeked in at Jacob, and he was snoozing deeply, so I pulled a Coke out of the fridge and sat back down to my labors.
I was a little bleary eyed when I heard her key in the door, and looked up. 1:20 a.m. I stood up as Emily closed the door behind her and turned to face me. She looked a little worse for wear, skin flushed, hair kind of wild, and the vestige of a spilled drink on her right hip. She staggered a little, and I could smell alcohol. “I took a taxi home,” she said. “I imbibed a little too much.”
“It’s cool,” I said. “Did you have fun?” She looked at me, and as she was starting to answer, she was taking a step, and slipped a little on her tall high-heels. I darted forward and caught her with one hand on her arm, and the other around the waist, and kept her from falling. She felt slim, warm in my arms. I pulled her up to her feet, and she slipped an arm around my neck. I could feel her warm, sweet breath on my shoulder through my T-shirt.
“Thank you, Jay,” Emily whispered. “You have very strong hands.” Embarrassed, I pulled away. This woman might be old enough to be my mother.
“I tripped, “ she explained. “I’m a little lit right now, but not fall down and fuck me drunk.” She bent down and took off her high heels, and in the doing of it her dress front popped open a bit, and I could see one of her perky apple-size breasts, the nipple lying against her dress.
“No, you’re fine.” I said. “Jacob’s asleep. I checked him an hour ago. I’m just writing an essay on Aristotle’s world view. You could have stayed out later if you wanted.”
She made a dismissive sound. “Fucking friends tried to bring me to an orgy. You know how bad that is when you’re a single gal?”
I shook my head. She looked quizzically at me. “Of course you don’t. Sorry. I forget you aren’t a full adult yet. You’ve probably never been to an orgy I’m guessing?”
“Nope,” I said. “I’ve seen them on porn films.”
“Right. Well if the men were bona fide porn actors that would be one thing. But this particular party had like ten really creepy dirty guys. My girlfriends dragged me in. I took one look around, and bee-lined for the door. Fucking mattress on the floor in the middle of the living room and everything. Gross.”
“Did your girlfriends leave with you?”
She shook her head, and stepped toward me, swaying a little. “No, but they wanted dick so bad, they didn’t care what it was attached to. Me, I’m a little more picky with my dick.”
Emily put her arms around me. “You are a very handsome boy. Never noticed that before.”
“Thank you,” I said, just standing there, half in shock, half turned on by the way that something had completely dropped all of Emily’s pretension, her aloof mannerisms. She was actually TALKING to me about adult things. I was enraptured.
“Virgin?” she asked out of the blue.
I stepped back from her, suddenly not feeling so warm and fuzzy. “Seriously?” I asked. “I’m 19. Do I look like a virgin? Jesus.”
Her eyes flashed, and she reached up and pushed a lock of long black hair out of her face. “Sorry, that was shitty of me. And no, you don’t look like a virgin. How many girls have you fucked, Jay?”
“Oh, I don’t know if I’ve counted,” I started to mumble.
“Bullshit,” she laughed. “Tell me the truth and I’ll show you my tits. You like my tits?” Emily stepped forward, turned around in a slow swirl, and didn’t even wait for my answer. She pulled her dress top apart, and her perky breasts popped out as she faced me again.
“Yes, very nice,” I said. “And I’ve fucked six women so far. If blowjobs and handjobs count, add in three more.”
“But subtract one if any of those are family,” said Emily, pleased with herself at her clever response.
“Well step-sister should count,” I argued.
“Ok, but no step-moms,” she said. “Why aren’t you touching them?” I stepped forward and gently raised my hands up and squeezed her breasts, feeling the surprising weight, the soft hot skin, the dark burgeoning nipples. She moaned. After about 20 seconds, her eyes popped back open and she looked at me. “Wait here. Don’t go anywhere. I’ll be right back.” And she moved quickly away, headed up the stairwell and out of sight. I could hear the floor creak above me, as she moved around on the second floor.
“Fuck,” I breathed, talking to myself. “You fucked that shit up. She is NEVER going to hire you again. She fucking had to run away from you!”
Sure enough, when Emily came back downstairs about three minutes later, she was wearing a thick plush coral-colored robe. She was holding a handful of 20’s. “Here is your money, my dear. Sorry I molested you. I hope you can forgive me.”
“No, I’m sorry,” I said. “It was my fault.”
“Um, dear, no it wasn’t.” said Emily, a wry smile at my discomfort. She tossed the twenties on the table, and moved to the stairwell.
And the robe dropped. Her full nude body, so tall and slender, was slightly hidden in the shadows, but there was no hiding her intent.
“Well,” she asked, looking over her shoulder at me. “You coming upstairs?”
Gulping, I stepped forward, feeling the blood rushing into my cock. I was beside her, with her still facing away from me, and then she moved a step over, and I was right behind her warm body, my arms around her waist and rubbing her slim belly, her ass pushed against my turgid crotch, her head leaning back and obscuring everything with her wild black hair, and her intoxicating odor overwhelming my senses.
“It’s a good choice you just made,” Emily whispered. “You won’t find me in spirits like this very often. Shall I lead you upstairs into my bedroom?”
“Please,” I said.
“Come,” she ordered, and gently took my hand and led me up the stairs.