Weird Wild Weekend Pt 02 Sexy Saturday

Find the first part here: https://www.literotica.com/s/weird-wild-weekend-freaky-friday

(Author's note: This is a work of fiction and, as such, does not reflect any actual events. Character resemblance to any persons, living or dead, is entirely coincidental.

The author does not condone any of his demented fantasies being played out in reality unless all parties involved are of legal age, sound mind and fully agreeable to the scenario beforehand. Please, remember it's just a story and try to not take it too seriously. Thanks for reading and happy fapping!)

*****

I awoke the next morning, not feeling very rested, and sat at my desk to think. The events of last night didn't seem quite real and I wasn't sure what I should do now. I idly drummed a rhythm on the wood with my fingertips and considered, 'at least it's my day off. I have all day to think of something. I just need a way to broach the subject so I can get her to tell me what she and dad were talking about last night. I've got to figure out how to get another go with her now I know she wants it. All I can really do is play it by ear and see what happens, I guess.' I nodded to myself, then got up, got dressed and went downstairs to see if either of them were awake yet.

"Hey, Jim," my dad said quietly. He was sitting on a stool at the end of the island right next to the coffee maker with a steaming mug in one hand and an ice pack held against his head with the other. "I think I hit my head on something last night."

"Ouch," I sympathized. I poured myself my usual half and half mix of hazelnut creamer and coffee, then asked, "mom up?"

"No, not yet. I have to go to work in about an hour, unfortunately, but it's her day off, so let her sleep in."

"Okay. I'll probably just spend the day playing on my computer. You two have fun last night? You must have got home real late. I didn't hear you come in."

"Yeah, it was nice. Your mom and me had a real good time." He looked at me for a long moment, then said, "you should maybe talk to her. Tell her what's been going on with you, how work is. You know how much she likes to hear about that stuff from you. We were talking last night and she's feeling a little sad about her baby boy growing up. She knows you've been thinking about moving away for college and she's worried you'll only come home to do laundry and ask for money."

I laughed gently, "I'll talk to her. I haven't given it too much serious thought yet, though. I'm kind of enjoying being free of school right now, and I think I might just work for a while and save up some money before I make real plans."

"Good. Good. Tell her that," he clapped me on the shoulder. "It'll make her feel a lot better to know that. You are welcome to stay here and take the time you need to figure it out. You know we like having you here. You just keep up making your car and insurance payments, we'll take care of the food and stuff."

"I know, dad. Thanks." I gave him a hug and took my coffee upstairs to my bedroom. A while later, I heard his voice out in the hall telling mom goodbye and I opened my door to wave at him. He kissed my mom, waved back and skipped down the stairs whistling as though he hadn't been knocked unconscious recently.

"Morning, kiddo," mom said, cinching the belt of her blue silken robe tight around her middle. "How you doing?"

"Hungry. You?" I was finding it difficult to act natural knowing she was still full of my cum from last night. A faint aroma of alcohol and sex tickled my nostrils every time she moved.

"Yeah, me too." She yawned and stretched, then put her arm around my shoulders to meander down the stairs with me. She set a skillet on the stove, twisted the knob for heat and asked, "what do you want for breakfast?"

I poured us both some coffee and sat on a stool. "Cheese omelet?"

She weighed my request against her hangover, "hmmm...yeah. I suppose that sounds alright. You're in charge of the toast, though."

"That's fair," I replied as I moved to get the bread. I couldn't think of a smooth way to ask her what I really wanted to, so i just blurted out, "dad said you and him were talking about me last night."

She paused cracking the eggs into a bowl and asked uneasily, "what did he say?"

I considered my words carefully as I spoke, gingerly picking what I hoped was the best path through this potential minefield. "Well, a lot of things. Like, you were worried about me moving away for college."

She went back to work slowly, responding warily, "I am worried. I'd rather you go to school near here so you can live with us. Save some money, help you out with laundry and things."

"I haven't decided, but I think I'm going to wait a semester or two before I do. Enjoy being free for a little while." I got out plates and forks and set us some places.

She clicked her tongue with irritation, "okay, but not too long, please. College is important."

"I know, mom. I know." I shrugged as I scraped butter onto the first slices of toasted bread. "I'm going to college. I just want to be a kid a little while longer. Being a grown-up will last the rest of my life."

"Maybe you can try to find a girl, have a few dates," she smiled at me and poured a couple glasses of milk. "Since you're trying to have some fun."

"I don't know, mom. Girls are...girls are...," I trailed off, uncertain how to finish that thought in a way that wouldn't sound awful.

"Girls are...what? Pretty? Fun? Difficult?" She leaned on the counter, squeezed her impressive tits together and looked comically serious, "you do like girls, don't you?"

"What? Yes! Definitely," I said getting flustered. My face was hot with embarrassment as I tried to tear my eyes off her mountainous cleavage. "I like girls."

She giggled and went back to the stove to finish cooking the eggs. "I'm glad to hear that. Not that it would bother me if you were gay, but you know how people are. I'd rather you didn't have to deal with all that."

I bit my tongue, trying to pick the right words to say. I wished I could just ask if she wanted to fuck, but that would be a disaster. I had to ease my way up to it, using my knowledge of what dad had said to her. Hesitantly, I croaked, "I...I'm not very good with girls, though. Dad suggested you could maybe help me out with that. He said he was talking to you about it last night, but you thought I would be embarrassed. I am, but I could use the help. If you don't think it would be weird."

"Help you with what, exactly?" She gave me a stern look. "What did your father tell you?"

I couldn't meet her gaze. I picked at my fingernails and stammered, "th-that you...you, um...you kind of...well, felt sorry for me because I was still a virgin, and that maybe you should teach me about...about...women."

"What about women?"

"About, you know," I looked up at her sheepishly. "About...what to do with a girl."

She didn't say a word, just stood there with a hip cocked to the side, her arms folded over her bosom, lips pursed tightly and narrowly slit eyes staring at me for a long while before she moved to grab the skillet. She served out our steaming food then sat quietly next to me. We ate in uncomfortable silence for several minutes and I poked at my eggs, worried I had messed something up. As the awkward tension hung like a swarm of gnats between us, she kept looking at me out of the corner of her eye and I could tell she was thinking seriously. There was no way she'd say yes, so I figured she must be trying to find a way to say no without hurting my feelings. She deliberately made her way through her whole breakfast before she spoke. Finally, she set her fork down, wiped her mouth on a napkin and said decisively, "okay. I will teach you."

My heart tripped and my ears tingled. Had I heard her correctly? "You'll teach me? Really?"

"Yes," she nodded, then wagged a warning finger at me while she cleared up our dishes. "But, I'm only helping you to get a girlfriend, right? This isn't some weirdo incest thing. We're a respectable family."

"Right, mom," I hopped up off my seat and agreed quickly. "A girlfriend."

She stared me down for several seconds, holding my gaze to make certain she was understood and in control, then her expression softened and she clapped her hands together. "My little boy is growing up. Time for you to learn how to be a man." She threw her arms around me and squeezed me tight. "We're going to have so much fun, baby! And we're going to start with a date. Enjoy your day, then clean up and get dressed. You're taking me out to dinner tonight. Make sure you pick a nice place and meet me at the front door at seven o'clock looking good."

"Yes, ma'am!" I kissed her cheek, then turned to go, but she grabbed my wrist and whirled me back to face her.

"Jim, honey, if you're going to kiss a girl when you ask her out on a date, do it right." She drew me close, her delicate fingertip curling under my chin, and planted a searing hot smooch on my lips. I felt my knees slowly melt out from under me as her tongue pressed its way into my mouth and my eyelids drooped closed as I gently sucked on it. I slid my hand down to cup her ass and bent her back as I held her kiss for what felt like hours. I was slightly dizzy when she pushed me away and barely heard her husky voice say, "that's much better. Remember, you need to impress a girl if you're going to get into her panties."

I floated up the stairs in a numb daze nothing more than a pair of damp, sizzling lips and a pulsing, stiff cock. The afternoon moved quickly at first as I called a well-reviewed restaurant for reservations, then took a shower. picked out my clothes and got dressed. But as I sat and played a game, trying to pass the time, everything slowed to a crawl. I watched the numbers on the display in the bottom corner of my monitor. 12:49...12:50. Every tick of the clock took a month and a half to tock by. 3:11...3:12. The afternoon crept by at a snail's pace. 5:37...5:38. It was excruciating sitting still, knowing what was coming, struggling to keep myself occupied. 6:03...6:04. My thoughts raced and my mind would not be still.

Would she actually let me get into her panties, or was she just going to tell me how things work like I didn't take sex ed at school? Was this just going to be a one-time thing? How could I get her to give me more "lessons"? I hoped I wouldn't say something stupid or spill something on her or fuck everything up somehow. And I didn't want to even consider the potential embarrassment of getting inside her and only lasting three or four strokes. This was the chance I'd been desperate for since I figured out why my dick would get hard every time she was around and I did not want to ruin it. I paced back and forth, reflexively straightening my tie over and over and trying to will myself to not sweat profusely. I was so nervous watching the last minutes count down, I decided I couldn't take it any more. I went downstairs and stepped out onto the front porch to cool off and get some fresh air.

Stringy white clouds skated across the sun and birds chirped in the nearby dogwood trees. Cars and trucks bustled merrily along the road at the bottom of the hill in a soothing woosh. The breeze gently blew away my anxiety and I focused on my breathing and heartbeat, trying to remind myself that most of the difficult part of asking a girl out was already done. After a while, I felt better. I checked my watch, then, in a fit of whimsy, rang the doorbell as though I were arriving to pick her up. A few moments later, she opened the door, looking confused.

She had her hair tied back with a thin, green ribbon in a simple ponytail and her loose, summery, floral-patterned dress was cut low to show her supple cleavage. The broad, brown belt about her waist accentuated the natural flare of her wide hips and the short skirt gently fluttered in the breeze, hugging and hinting at the hidden curves beneath. I looked her up and down, swallowing hard with a suddenly dry mouth. She smiled as she realized who was at the door, and said, "hey there, handsome. I wondered where you were. Ready to go?"

"Absolutely!" I offered my elbow to her and blushed hard as she slipped her arm along mine, snuggled up next to me and her soft boobs pressed against my bicep. "Y-you look beautiful, mom."

"Thank you, sweetie, but maybe you should call me Sharon for tonight." She looked at me coyly, "unless you want people to know you're on a hot date with your mom."

I laughed shakily. "Y-yeah, I...I guess so."

She prodded my side with her elbow, and chided, "hey, calm down, kiddo. It's just me. It's just dinner." She pulled me towards my car. "We're going to have a good time, so relax and enjoy yourself."

I inhaled, then exhaled. "Sorry, mo...I mean, Sharon. You're right."

"A little confidence can be very sexy, Jim," she instructed as we walked. "Act like you're in control and know what you're doing. Just don't get too arrogant and full of yourself. Be cool. Give a lady your arm and lead her like you know where you're going and what you're going to do when you get there."

"Be cool. Confident and in control." I nodded, then smiled as calmly as I could manage and said, "I made us reservations at 'Il Giardino'. Let's get going."

She licked her lips hungrily, her eyes getting wide. "Is that Italian? Good choice! A fancy meal at a nice restaurant can go a long way towards getting a girl to want to go back home with you."

I opened her door and stared in dumbfounded fascination at her long, smooth legs disappearing under her billowing skirt as she sat quickly and drew the seat-belt into place between her plump boobs. I thumped the door closed and walked around to my side, trying to get my brain to cooperate and be normal for a while. I had to be cool, I couldn't keep gawking at her like this, but that was so much easier said than done. Thankfully the needs of driving quickly soaked up my attention and I kept my eyes glued to the road, going through the motions in my head as deliberately as I could, as though I were taking the driving test and mom was my instructor.

As we merged into traffic at the end of our cul-de-sac, she leaned to turn on some music, saying, "here's a little trick. Let your girl control the radio on the way to your date. You can tell a lot about her mood and what she might be into that night by what she plays, if you're paying attention. She might play something sad or aggressive depending on how her day went, so that's a clue you can use to maybe steer the conversation a little. See if you can help her feel better." She flipped through stations as she talked, trying to find one playing something she liked. "If it's just safe office-variety pop music, well, that can be tricky to interpret and you'll have to find some other tells. What you're hoping for is that she'll pick some dance music or R&B, something a little more sexy. Yeah, like this." She turned up the volume on Marvin Gaye pleading for his woman to "get up, get up, get up, get up".

I glanced over to see her wiggling and bouncing to the music, lip syncing the familiar words, and grinned. My head swam in a heady mixture of embarrassment and pride. I wanted to show off the hot cougar milf going out with me, but my world would end if people knew it was my mom. This was going to be a strange date. I shook my head, sighed lightly and chuckled to myself. 'Relax and have fun, she said.' I gathered my courage along with my breath, then brashly sang along. "Makes me feel so fine. Helps me lose my mind."

She joined in. "Sexual healing, baby, is good for me..." She pulled my right hand off the wheel and put my palm firmly against her thick, warm thigh. "Sexual healing is something that's good for me."

Her silky, well-lotioned skin was buttery soft under my fingers and I fumbled through the words of the bridge, trying my best to at least maintain the melody with her as I split my brain up between driving and singing and fondling her leg. I had watched my dad do it a million times over the years and he had made it look so easy and cool. It was the most challenging drive I've ever made to anywhere. Somehow, I got us to the restaurant alive and only a couple of minutes late.

I rushed around to open her door when we got there and offered my hand so I could enjoy the show of her swinging her legs to the side to step out of the car. I was trying to play the total gentleman part tonight, thinking maybe she'd appreciate the old-fashioned chivalry. I held the restaurant's door open to watched the bouncy swish of her backside as she sashayed towards the cute hostess behind the counter. I followed in her wake, my eyes glued to her hypnotic bottom, helplessly gripped by my mindless libido.

"Welcome to Il Giardino Dei Piaceri," the petite blonde's practiced pronunciation greeted us as we approached. "Do you have reservations tonight?"

I spoke with her and got us seated, reminding myself to wait until mom's butt had touched the chair before dropping into my own, then smiled up at the slick-haired, black-suited waiter that sauntered over.

"Good evening, my name is Tony. I'll be taking care of you tonight." He flashed a brightly-polished bay window of a smile at us and leaned in to light the candle in the center of the round table, then set a little wicker basket of bread between us. "What may I get you to drink?"

"A glass of the house white wine for me, please," my mom answered, pulling out her driver's license with an impish grin. "But just a soda for my date, I think, since he's driving."

"Whatever cola you have is fine," I told him with a tight smile.

He handed back her card, winked knowingly at me, and crooned, "of course."

I gave my mom an evil glare as the waiter walked away. "Are you making fun of me?"

"Oh, honey. Don't be so thin-skinned." She drew electric patterns across the back of my hand with her fingernail, and her emerald eyes sparkled in the dancing fire-light as she pouted sweetly at me. "It's just a little harmless ribbing. The waiter doesn't care about our ages as long as you don't try to order any booze. I'm sure he gets all sorts of couples on dates in here. We're just another table of customers to him."

"Okay. I'm sorry." I toyed with her fingers, entwining them with mine and tracing their outlines gently against the white tablecloth. "It's really hard to not be nervous around a gorgeous woman like you, mo...," she squeezed my hand, shushed me and glanced around to see if anyone had heard. I continued hesitantly, "...um, Sharon. I want everything to go just right, you know?"

"I know," she caught my hand in both of hers and kissed my knuckles tenderly. "It's fine. Here, have some bread." She buttered a piece and passed it to me as the waiter returned with our glasses.

We ordered some salads and two different pastas and things were going very well. We talked. Or, rather, I stammered and struggled to find ways to make her laugh, hoping to win her with humor, taking any chance I could to touch her hand or stroke her arm. She scintillated. I didn't know what that word really meant before that night at that table. She had an effortless sensuality about her and she radiated an intoxicating aura of sophisticated allure and coy, feminine invitation. She played this mating game well and knew how to be chased, how to tease a man along behind her. She was right, confidence was very sexy and her years of experience lent her a sense of poise that was impossible to fake and quite arousing to someone like me who had spent so much time chasing chaste pixel princesses and rescuing digital damsels in distress.

Tony had cleared away our dinner dishes in preparation for bringing us a desert menu and my mom said, "I need to use the lady's room. I'll be right back."

In my haste to be a gentleman, I stood up too quickly and banged my thighs into the table, rattling the silverware and knocking my chair over backwards. I righted my chair, hoping I hadn't heard her cluck her tongue in annoyance as she walked away, then I sat down heavily and put my face in my hands, feeling rather disgusted with myself.