Freshman meets away Family

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Glen meets Mary-Louise, her sister and daughter.
6.6k words
4.38
26.7k
53

Part 1 of the 2 part series

Updated 06/11/2023
Created 01/03/2022
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I work part time at a local grocery store in our thriving little town, while attending my first year at a university in a larger city. My friendship with Mary-Louise, a divorced mother of one teenage daughter, blossomed over the past year. We were 17 years apart in age, yet we could share our most intimate, sensual desires with each other.

We flirted and often stole little kisses and, to my surprise; she enjoyed rubbing her lovely little ass against my crotch anytime the occasion presented itself. However, I never dreamed that our friendship would extend much beyond the shop floor. It heightened my astonishment when Mary-Louise asked me over for dinner to meet her older sister, Jessie, and her 18-year-old daughter, Ashley.

It was a warm fall evening. The stars were twinkling, and the moon was shining as I walked up the sidewalk to the front entrance of her apartment building. I hit the buzzer. Seconds later, she announced that she'd be right down. While I waited for her, I took a quick look around the area, noticing that her apartment building was in a nice, quiet neighbourhood.

"Hi Glen, please come on in."

My heart fluttered as Mary-Louise tossed her dark, wavy hair and smiled. She has a lip - smacking medium-sized body and stands about 5`6" tall and weighs 115 pounds. She wore a scarlet off-the-shoulder mini dress with a floral print. Her perfume was exquisite and delicately fresh.

She took my hand, leading me up the stairs to her apartment, then to the sofa. "Have a seat, Glen. Ashley and Jessie will be out in a minute."

Mary-Louise's nickel size areolas and her nipples caught my attention; thanks to a lamp next to the sofa, I could see the shape of her petite hips and her inner thighs through the sheer, silky fabric of her dress. I also saw that she wasn't wearing panties, and that she had a thick black bush. I developed a carnal, mind-blowing crush on her.

"Excuse me, I have to put something in the oven. Dinner will be ready in an hour."

While Mary-Louise went into the kitchen, I sat and looked around the living room. They cheerfully decorated it with some old Norman Rockwell style paintings on the wall. A small table with a white tablecloth stood next to the sliding glass door that leads to the balcony. On the table there were several photographs, perhaps of family and friends. A large television console stood along the wall opposite to me. A big plush, beige coloured chair sat next to the sofa off to the right, filled with soft, oversized pillows and stuffed animals. Cat toys littered the floor throughout the apartment, although I didn't see one that night.

After several minutes, Mary-Louise returned and sat herself down on the sofa next to me. We talked about her job, the store, and some of the upcoming sales. Soon, the conversation changed.

"How were classes today?"

"Okay, I guess, nothing too exciting."

"Is that sexy professor you like still around?"

"Yeah, she's still there. She's not teaching my course anymore. They moved her to another one."

"Aww, maybe someday, we could arrange something between us."

"Oh Mary, now you're getting me hard!"

"Good, a young man should always be hard. Especially around me." she snickered.

Mary-Louise stood up from the sofa to flaunt herself, turning around several times before facing me once again. "Do you like my new dress? It shows off my body really well, doesn't it!"

"It shows everything I want to see; I love it. You look so gorgeous in it."

"Aww... thanks! Do I look hot too?"

"Oh Shit, you're burning up in that dress!"

Mary-Louise grinned, then sort of flopped down on the sofa, putting her right arm underneath my left arm, then wrapping her hand inside mine and locking fingers. She gave me a long, fervent kiss on the lips. I was just about to push my luck and touch one of her medium-sized breasts when Ashley came out and gave her mother a hug and a long kiss. Her timing pissed me off a bit. But I did not know. However, that my luck would change for the better that evening.

"Glen, meet my daughter Ashley."

I responded with a big smile, "Hey Ashley, your mom talks about you all the time!"

"Uh-oh, Mom, you didn't tell him the cat story, did you?" Ashley looked at her mom, somewhat embarrassed.

"Oh Shit," Mary-Louise laughed and waved her hand in the air. "Glen, she's referring to the time about a year ago when she was taking a bath. Our cat was walking along the edge of the tub, slipped and fell into the soapy water. Fritz shot out, and Ashley tried to catch him to dry him off. But she left the apartment door open with just a crack, and the cat slipped through the opening. As I was walking up the stairs, the cat came running down, with Ashley hot on his tail, bare ass, tits swinging and everything. The cat raced down the stairs till it ran out of places to run. I spun around to follow them. The downstairs neighbours, an elderly couple, just stepped out of their apartment, saw her flying by in all her nudity, and followed them. Ashley caught the cat, stormed past the old couple, who looked at her, disgusted by her nakedness. To piss the old couple off, she told him he should come up for a quick fuck sometime, then she and the cat took off upstairs. I learned that day I had a slut for a daughter, a rude one, too."

"Mom..." Ashley whined. "Damn you Mom!"

Ashley loves it when her mother tells that story. She stood in front of me with an embarrassed smile, giggling.

Ashley is a year younger than me, and she looks like a younger version of her mother, except she has beautiful light blonde hair that curls inwards at the shoulders.

She's dressed in a flimsy white tube top that came to an abrupt halt, exposing the bottom of her tiny boobs. Her washed black denim shorts at the top were unbuttoned, and the bottom rode high up her ass cheeks. Ashley was four foot-eleven inches tall and weighed 95 to a 100 pounds. It was no surprise to see her in bare feet with bright red toenails.

Ashley gave me a brief smile before bending down and giving me a sizzling embrace and a kiss, the kiss that a good girlfriend would give. I wrapped my arms around her perfect little waist and slid my palms up and down her back, feeling her warm, soft, pale flesh. As Ashley drew back, her top slid up, revealing her long brownish nipples. She pulled her top back down as if nothing happened. The material of her top did nothing to hide anything. In short, she may as well have gone topless.

"Damn, she's my kind of girl," I thought to myself as she seemed unconcerned about anyone seeing her naughty bits.

Her mother didn't appear to be bothered by her dress, which in a way surprised me at first. But, then again, Mary-Louise's dress showed almost as much of her body as Ashley's. In the store, I've seen young girls chastised or scoffed at for wearing far more clothing than what either of them wore that evening. To say I was hot and bothered that night would be a vast understatement.

Mary-Louise moved over to allow Ashley to sit next to me. Ashley and I connected; within minutes, she cuddled up to me on the sofa.

Jessie appeared just as Mary-Louise was ready to say something. Her hair was black with greyish streaks, and parted in the middle, falling to her ribs. Jessie looked every bit as attractive as the other two females. She had on a brown mesh top with a wavy design that showed off her puffy nipples. Her white pants were thin and silky, highlighting a rather large camel toe. She looked to be the same height as Mary-Louise, but was a couple of pounds heavier. It took everything I had not to jump her.

"Glen, I want you to meet my sister, Jessie." Mary-Louise laughed. "She's the slut of the family."

"She's right about me being a slut. My mind is always on sex all day. How about you, Glen? Do you think about sex too?" Jessie smiled and gave me a hug and a quick kiss. "It's nice to meet you."

"Hi, I guess I do too." I replied with some shyness.

"You sure don't talk much, do you?" Ashley said, her voice breaking with laughter.

Mary-Louise kidded, "Let him get to know you better. He never shuts up any other time."

"Thanks, Mary," I joked. "I'll remember that next time you want some extra beef."

"Ahh... temper, temper!" she teased.

The four of us sat and joked around for a moment, then Mary-Louise announced dinner was ready. We took our seats at a tiny, intimate table for four. Because it was dark outside and the lights were dim, it cast a dark shadow throughout the dining room. All it needed was a few candles and it would've felt romantic.

There was a brief period of silence. The only sounds you could hear were the clanking of dishes filled with food and cutlery as they were being passed around the table.

"So, Glen, do you have a girlfriend or anyone to fuck?" Aunt Jessie asked bluntly.

"No, I don't have anyone." I replied.

"Why don't you?" I realized I was on the hot seat at that point, and they put aside the niceties; they were measuring me up. Mmm... why would this be? I wondered?

"Guess I'm not good looking enough." I shrugged. Aunt Jessie is not one to mince her words. Her approach to questioning may intimidate some people. However, I didn't mind her open questions.

"Mmm... I dunno. You're cute enough. Maybe you chase after the wrong type of girls." She said as she took a bite of her celery stick.

"I'm not interested in the glamour type, if that's what's on your mind. I'm attracted to personalities over huge boobs."

After a few more targeted inquiries, Jessie responded with one last question. "Does nudity worry you, or would letting your cock hang out in front of a group of girls bother you?"

"Hell no, a female seeing me naked doesn't bother me at all," I sighed. "I'm more concerned about the prudes who get offended and want to call the cops."

Jessie whispered to her sister. "Don't let this one get away. He could be fun."

"Well, you can come over, pull your pecker out and hang out with us anytime you want." Mary-Louise said as she rose to get the dessert from the kitchen.

"Thanks Mary." I chuckled, but I didn't really believe that she meant it.

After dinner, Aunt Jessie and Mary-Louise each lit up cigarettes, and we loitered around the table, chatting. After a while, the two sisters stood up and cleared the table.

Ashley grabbed and squeezed my hand and motioned for me to follow her. We strolled into the living area and sat down on the couch. She sat next to me, feet on the sofa, legs spread, and grabbed the remote, which she used to turn on the television. She put her hand between her legs and began caressing herself through her denim shorts after a few quiet moments of watching television.

"Mmm, Glen, will you put your arm around me?"

Without hesitation, I encircled Ashley and held her firmly against my chest while she rested her head on my shoulder. Her hand moved from playing with her clit to caressing my thigh. I could feel my rocket getting ready to launch.

"Do you think I'm attractive?" Ashley asked, her gaze still fixed on the television.

"Oh geez, you look incredible!"

"Would I be the type of girl you'd just whip your dick out and bang without a second thought.?"

"Oh Shit, oh yeah!."

Ashley looked up without lifting her head, and with a brief glance, she giggled, then returned to rubbing herself and watching the show.

"Do you think my mom and Aunt Jessie are attractive too?" she asked.

"Are you kidding? Damn right they are... they're gorgeous!"

"Could you fuck them too?"

"In a heartbeat!" I fired back.

"Does it disgust you if we like to play together sexually, I mean?" Ashley asked.

"Nope, not at all... in fact, it sounds great."

"Would you hang out with us sometime?"

"Oh yeah, I'd love to. Is this line of questioning going somewhere?" I asked inquisitively.

"MMm... mm... It's going everywhere." Ashley said, laughing.

Ashley laid her head back on the sofa and continued watching television and fingering herself. A few moments later, she stuck two fingers in my mouth. "Mmm... how do my fingers taste?"

"I dunno, I may need another sample to confirm my thoughts." I flirted.

"You know where to get more. There's more than enough for you. But, you know what, I've got a better idea." She said as she ran the tip of her index finger over my shorts, along my now hardened shaft.

"As long as the well doesn't dry up. I'll take all I can get." I teased.

"Does it bother you if I play with your pecker?"

I simply nodded no, as if I would've had a choice with her, anyway.

She slid her tiny hand between my legs and the material of my shorts, then gently grasped my stiff penis, pulling it out and cradling it in her silky soft hand. Her face was alight as her eyes twinkled, and her pearly white teeth formed the most beautiful smile I'd ever seen.

"As long as I get to play with those perfect tits," I expressed.

Ashley busted up laughing and flashed a grin. "Glen, you've seen my boobies at least a hundred times already tonight, every time my top cropped up.

Ashley added. "Believe me when I say I will not stop you. You are free to do anything you want with whatever you want."

Ashley jumped up and stood with one foot on the floor and a knee on the sofa. As she pulled her little tube top over her head, her silky light blonde hair clung to it like a tangled knot. Ashley threw her black shorts and her pink panties on the floor by the coffee table. Then she quickly adjusted her hair. Ashley had a small, single rose tattooed on the crease between her bare pussy and her upper leg. Her labia looked stunning, with just a hint of blackness at the margins. She stood in front of me, and with her fingers she separated her lips, revealing her beautiful pink hole.

She smiled and looked me in the eye. "Does my pussy look nice, Glen?"

"Damn, it's so hard not to fall in love with you, Ash. You've got an amazing body." I said as my eyes wandered over her tiny frame, taking in her heavenly beauty.

Ashley wrapped her arms around my neck and laid on top of me, peppering me with kisses. My hands were all over her body and through her lustrous, blonde hair. She slipped my shorts off, then I removed my t-shirt, socks and tossed them to the floor as well.

"Wow... you've got a huge boner there, Glen!" Ashley exclaimed as she placed her soft, pert lips against my hard shaft before she swallowed it whole. Someone who was well-versed in the technique of fellatio taught her well. I wonder who it was, her mom or Aunt Jessie.

"Trust me, it's easy to get a boner around you."

"Aww... thank you, that's lovely!" She said as she continued taming my manhood with her tongue.

"Would you like to finger my pussy and eat me now, Glen?"

"You bet I would. Lay on your back and spread wide."

As I drew my nose closer to Ashley's inner thigh, her aroma reminded me of damp cut grass and white wine. Her bodily secretions, however, had the flavour of a great red wine.

I ended up spending a lot of time playing with her wootsie. If Ashley's attitude is any indicator, I doubt she would be happy with plain vanilla sex; instead, I imagined she'd want it spicy and rough. In my perspective, Ashley grew up in not only a loving home, but one that didn't have limits or view sex just as means of reproduction, a money grab or as a taboo. Mary-Louise and Jessie emanated sensuality and Ashley grew up loving to look her best and having sex with none of society's guilt.

I upped the ante a tad higher, but the ulterior motive was that I became smitten with her adorable little starfish. I've got a feeling it's going to be a part of my most intimate fantasies for a while.

"Okay Ashley, I'm going to poke my finger into your pretty asshole."

"Oh... go for it, Glen," Ashley said, but stressed I should do it slowly. "At first it hurts a lot, because I haven't grown used to doing this yet. But once my ass muscles loosen up, I enjoy having my asshole fingered and sucked by other people. You could be the first person to shove your cock in there if you're good."

I took my sweet time taking turns shoving my finger into her behind and licking her. "Would you like me to slip my cock in there now?"

"No, let's do it later when Mom and Aunt Jessie can see us. They'd be proud of me having my first anal. You don't mind, do you?"

"No... of course not!" I shook my head and assured her, but I couldn't help but feel a little disappointed.

Despite my repeated licking and kissing her clit, she had no noticeable response at first. I worked my way down between her knees to her tiny little feet, meticulously sucking each toe. I made my way up to her flat stomach, running my tongue around her belly button as I went. Her apricot-sized breasts, brownish nipples and areolas were the most beautiful I'd ever seen. Her nipples were long and hard.

Ashley's lips looked and felt like a delicate red rose pedal. Her being the more aggressive kisser this time, she pressed her tongue into my mouth. Our two tongues danced like fairies on the point of a needle. Her saliva tasted like a mountain stream. She could get a guy off with just a simple, passionate kiss.

I inserted my stiff shaft into her tight little twat, and she let out a slight moan. Her teenage pussy didn't require any lubrication; it was fine on its own.

We established our rhythm of kissing and making love after a couple of strokes. I had reached the purest state of bliss. Mary-Louise walked into the room with a nonchalant air about her, picking up our clothing from the floor and stacking them on the coffee table while she watched us having intercourse.

"Wow Ashley, it's amazing to see you and Glen getting along so well."

"Here, let me climb on top and you can relax for a bit." Ashley instructed as she straddled her legs over me on both sides, then crouched down. I watched as my hard cock disappeared inside her.

As Ashley rode me, Mary-Louise stood by, a smile on her face, her hands brushing Ashley's back and shoulders. Then we changed positions. I shagged her in a doggie fashion as she leaned over the back of the sofa. I began slamming Ashley as hard as I could, increasing the intensity of my blows with each passing moment.

"Holy Shit Glen, not so fucking hard." Ashley snapped.

"Don't cum inside her, please Glen." Mary-Louise pleaded.

After I heard Mary-Louise, I quickly pulled out. She stood with her head beside my hip and put both arms around my waist. With one hand, she finished me with a hand-job. I unloaded over Ashley's gorgeous round ass. Mary-Louise stood smiling beside Ashley, who was still in the doggy position, took a couple of fingers and smeared my sperm all over her daughter's perfectly round bootie.

Aunt Jessie walked into the living room and detected sex in the air. "Whoa, someone just got laid, Did you just get laid Ashley?"

Ashley took another seat on the sofa, flushed and panting heavily. She leaned her head back and momentarily closed her eyes. Her hot, sticky skin pressed against me as she regained her composure.

Seconds later, she answered. "Yeah, Aunt Jessie, I just got a proper fucking... Holy Shit! Glen, you're incredible!"

Aunt Jessie appeared to be happy with her niece's success. She turned and walked out of the room, then returned seconds later with towels, which she handed to us. "Here, you two better dry yourselves off."

We took Aunt Jessie's suggestion and did just that. Ashley snuggled up to me once again. Mary-Louise sat up straight and proper in the big chair, hands on her lap, legs crossed, while Aunt Jessie perched on the armrest of the sofa, arms crossed and smiling; all the while, the four of us engaged in some light-hearted and sexy conversations.

After a while, Mary-Louise stood up and headed into the kitchen. Shortly after, I followed her.

Aunt Jessie looked at Ashley, a bit perplexed. "Where's Glen going?"

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