My Aunt's Best Friend

A/N - Hello all. To be honest, I was struggling to think of where to put this story as I didn't want to write a story in the same category as one of the previous four stories. However, while this does have an element of 'First Time', I've chosen this category as I simply think it fits better here. I think 'First Time' would have been more suitable if the ages of both people were similar.

Much like my 'Love Around the World' series, most of these stories will probably only be around 10k to 15k words. Well, that'll be the aim though they might go for longer, as long as the stories don't drone on unnecessarily!

Previous stories in this series:

My Brother's Best Friend (Transgender)

My Father's Best Friend (Gay Male)

My Mother's Best Friend (Mature)

My Sister's Best Friend (First Time)

Australian / British standard English. There is a good chance of reading the following: lots of profanity, characters drinking, typos, and bad grammar at times.

Proofreading and editing suggestions provided by OhDave1. Any mistakes are still mine.

Comments are appreciated as always.

Feedback by email is always welcome. Enjoy chatting with anyone who likes my work.

*****

A young man comes of age thanks to his aunt and her best friend.

*****

I was ten years old when my aunt was awarded custody of me. My mother was very young when she gave birth to me. My father wasn't much older, and they struggled as teenage parents. Mum didn't finish high school, my father barely managed to obtain his higher school certificate stating that he graduated, and from then on, things only got worse.

It's fair to say my parents were junkies. They were simply another statistic of young people in the western suburbs of Sydney, barely making enough to make ends meet, finding solace in alcohol, drugs and other vices. My father was little more than a sperm donor. I barely remember him showing any interest in me while I was growing up. I know my mother loved me, but while she might have tried her best, her addictions were getting the better of her.

When child services became involved, I remember my mother breaking down in tears, admitting she simply couldn't handle raising me. She said I was a good boy, but she wasn't cut out to be a mother. Her fun years as a teenager had been cut short thanks to falling pregnant, and she was finally forced to admit that she simply couldn't care for me any longer.

It was then a case of who would look after me. My grandparents were already well into their fifties by the time I was ten and didn't think of themselves capable of permanently looking after a ten-year-old boy. And they were also honest in that they'd already raised three children - my uncle, their oldest child, my aunt, the middle child, and then my mother, the youngest child - and didn't particularly want to help raise another child. My uncle was living his life to the full as a bachelor, and his one-bedroom apartment wasn't suitable for a child.

Then left my Aunt Cassandra. Child services talked to her about possibly taking me in. She didn't hesitate in stating she already had a bedroom available and ready to take me whenever they were happy that she was capable of looking after me. There were the usual checks, but it didn't take all that long for me to find myself living with my Aunt Cassandra full-time. Within a year of moving in with her, she had officially adopted me. I remember the day my mother signed the papers. She wept while hugging me, whispering she was sorry over and over again. But Mum was still struggling with her addictions and knew it wasn't going to be an easy road going forward for herself. Even my young mind understood that my mother had her demons and needed to focus on herself.

"She's doing her best," Cassandra said later that night when tucking me into bed, "Do you still love her?"

"Of course," I replied, "I'll never not love her. It's just... I won't miss living with her. And I definitely won't miss Dad."

She smiled before leaning over to kiss my forehead. "I love you, sweetheart," she said softly, "I don't expect you to call me Mum, even after today..."

"What if I want to?" I asked softly.

Aunt Cassandra had to look away for a moment, hearing her clear her throat before she looked back at me, her eyes glistening, a beautiful smile on her face. "If you want to call me some sort of title, John, I won't tell you not to..."

"Then I'm going to call you Mama from now on. Mum will always be Mum, but I should call you something too."

I found myself lifted up so she could hug me tightly, feeling her shaking as I looped my short arms around her body. "Thank you, sweetheart. I'll be the best mother I can be over the next few years."

I would love living with Cassandra and I knew how happy I made her the next morning when I walked out to the kitchen and asked, "What's for breakfast, Mama?"

She had to look away for a few seconds and I heard her sniffling. I walked over as she turned to give me a hug, making me smile as she kissed the top of my head. She said that since I was such a good boy I earned a big plate of pancakes.

Living with Cassandra gave me structure and discipline, and I think I surprised her by not going against her authority. She helped me focus on my schoolwork and was always available to help me with homework and assignments, particularly after I'd started high school. She encouraged me to play sports and loved standing on the sideline every Saturday morning in the winter.

By the time I was on the verge of turning eighteen, she'd supported me in getting my driver's licence as soon as I was legally allowed at the age of sixteen. Every weekend after I'd finished my game, she'd take me out driving and would let me drive to school each morning before she'd drive to work. When I suggested I get a part-time job to make a little pocket money, she assured me that my studies were far more important and that she made more than enough to give me a little cash whenever I wanted or needed it.

Mum wasn't in my life for a couple of years after Cassandra had adopted me. I did miss her, as despite her issues, Mum had never stopped showing love for me when I was growing up. Mum returned to my life when I was around fourteen years old. Cassandra warned Mum that she had to show a year of sobriety before she would allow our relationship to grow. To her credit, Mum showed her worth. She finished her schooling. Worked on gaining certificates, and by the time I was eighteen, she'd been in full-time employment for two years, had her own little apartment, and had long since dumped my father. She was happily single and was working on reconnecting with her family.

"Any ideas for what we should do on your eighteenth?" Cassandra asked one evening over dinner.

"Don't know. None of my friends are eighteen yet. I'm the oldest by a couple of months."

"You don't mention girls very often, John..."

I felt myself blushing as I knew that I was a little awkward around girls. I could never figure out why. I hadn't reached the much-coveted six-feet tall, but I did think five-ten was not too bad. I was certainly rather broad as I'd been a regular gym attendee since sixteen, focusing on strength and conditioning due to the physical nature of rugby league. And though I did struggle with girls, they seemed to like me as they were always nice and kind. But I didn't want to take their kindness as something more.

"I have girls as friends, just not a girlfriend," I said quietly.

"Well, if your friends aren't old enough, why don't we go out for dinner then hit a club, and maybe you'd like me to invite some of my friends? You know they all absolutely adore you, John."

I felt myself blushing again as I crushed on nearly all of Cassandra's friends. Hell, I crushed on my aunt through puberty as she was beautiful, intelligent and the endless love she showed me since the first night I'd slept in her house was something I could never thank her enough for.

"Can Mum come too?" I wondered.

Cassandra's smile was instantaneous. "Of course she can, sweetie. I wouldn't dream of heading out for your eighteenth without your mother. I'm glad you're as close as you are."

"You are?"

"She will always be your mother, John. Although I like to think that I do love you just as much."

"I love you too, Mama," I replied with a smile. Those words had her up on her feet and around the table to lay a big kiss on my cheek.

"And I love you, John," she whispered before hugging me as tightly as possible, "You're a wonderful young man. And I can't wait to enjoy many more years living together before you do spread your wings and fly."

Cassandra invited my mother to stay the night before my eighteenth birthday. I was woken up by a soft kiss on each cheek, opening my eyes to see my aunt and my mother smiling down at me, both wishing me a happy birthday before they snuggled into either side of me, making me chuckle as they continued to kiss my cheek and forehead. Cassandra announced she would go and start making some breakfast. As soon as she was gone, Mum needed a little cry, full of apologies for what happened years ago.

Turning to hug her, I'd long learned my mother was a tiny little thing compared to me, easily able to wrap my arms and hold her tight against my body. "It's okay, Mum," I assured her, "There's nothing to forgive. You had your demons and you've got over them. And we're now as close as ever."

"I'm just glad I've been with you for your past few birthdays," she whispered, feeling her snuggle against me, "I've loved seeing you mature." She paused before adding, "I am sorry about your father."

"I'm not. After everything you and Cassandra have told me, I'm glad he's disappeared."

"You don't miss having a male role model?"

"I have granddad for that. He's been a positive influence."

Cassandra cooked a full English breakfast for my birthday though I couldn't get out of going to school. I only had a couple of months left before my final exams, and I knew missing classes wouldn't be a good idea. She told me that she would make sure that she was home early, and Mum would be doing the same.

My friends did ask about my birthday plans. I told them that I'd likely have dinner with my family before heading out with my aunt, my mother and perhaps some of my aunt's friends. All my friends knew of my very close relationship with Cassandra considering the adoption. Knew the name of endearment I called her. And they'd also seen my aunt and some of her friends around the pool in our backyard during the summer.

Let's just say that our backyard proved popular from time to time during the summer when a gaggle of thirty- and forty-something women would happily prance around in some revealing bikinis.

I was always home first as school finished at least a couple of hours before Cassandra finished for the day. And given that she'd given me a used car as a present after passing my driving test, getting home was even quicker, even if I stopped to drop off a few of my friends first. I was busy studying when I heard her call out when arriving home, walking out to greet her with the hug and kiss on the cheek I gave her every day. Mum and Cassandra had raised me to never be shy in showing my love and appreciation for them.

"Are you looking forward to tonight, sweetie?" she asked after setting down her bag and following her into the kitchen.

"I'm looking forward to legally buying beer!"

That made her laugh out loud as she pulled a bottle of wine from the fridge. She also grabbed a bottle of beer that had been sitting in the fridge since the weekend when we'd gone shopping together. I couldn't legally buy them on the day, and she warned me that I would have to wait, but she let me select the four beers I wanted.

"Your mother will be here in around an hour, and we'll get a taxi together to the restaurant," she told me, "She's so excited about tonight."

"I'm just glad she's coming with us."

"She wouldn't have missed this for the world, John. She loves you so much."

"I love you both just as much. I've always considered myself fortunate to have two mothers."

Cassandra looked at me and then burst into tears. I knew my turning eighteen was a big moment as I was now an adult, and I knew she worried about our future relationship. Holding her in my arms, I leaned down and whispered into her ear that she would always be 'Mama' and that I loved her with all my heart. That just caused her to cry even more, feeling her clutch me tightly.

"Sorry," she finally whispered after sobbing for a couple of minutes, "It's just seeing you grow up these past few years..."

"You know how much I love you, Mama. As much as Mum. I love you both equally. I will always be thankful for the fact you adopted me."

"You're my son," she whispered, "I share you with my sister."

Sitting down on the couch in the living room, she cuddled into me and I couldn't help smiling. Our relationship had always been close, and I hoped it would continue. We discussed my upcoming exams and my hopes and dreams for afterwards. I knew I wanted to go to university as my ambition was still to be an engineer.

"Who is coming along tonight?" I asked as I knew none of my friends would be coming.

"Well, apart from me and your mother, I've invited some of my friends that you know. Is that okay? I know you're rather shy sometimes." I felt myself blushing as she leaned back, and I knew my cheeks were a little red. "I know you have a little crush on some of my friends, and that's okay. But you never mention any girls... You know..."

"I'm hopeless," I admitted, "I have lots of girls as friends, but I can't even ask one of them out without being all tongue-tied and nervous. And then... I mean, when your friends are here and parading around the pool..."

"It's okay, sweetie," she said softly, "Well, apart from me and your mother, I'm inviting Charlotte, Emma, Wendy, Isla and... Nancy..."

I felt my eyes light up at the mention of the last name and Cassandra would have known why. Out of every woman I knew in my life, I had the biggest crush on Nancy. I'd met her barely days after Cassandra had adopted me. She was a couple of years younger than Mama though they'd worked together for over a decade.

Gorgeous golden blonde hair. A tight, toned body that I couldn't help but gaze at every single time she wore a bikini by the pool. Long, luscious legs. A pair of breasts that were not large but were just perfect for her frame. Gorgeous blue eyes that were often covered by the lenses of her thin black frames of her glasses whenever she wasn't by the pool. A cute little nose and a mouth that I'd dreamed about kissing for years.

To be honest, she'd been the cause of more than one wet dream over the years. And Cassandra was definitely more than aware of the serious crush I'd had on Nancy since the first day that I'd met her.

"Okay," I managed to squeak.

Cassandra chuckled as she leaned into me. "I know how you feel about all of them, sweetie. Nothing wrong with having a crush on an older woman or two." She paused and kissed my cheek. "And I've never been blind to your feelings for Nancy."

"I'm still awkward around her," I admitted.

"And she knows exactly why. She's never thought you were anything but incredibly cute, and when you finally get over that awkwardness, you can talk to her like anyone else. She's looking forward to tonight, John. She adores you."

"She does?"

"She's a single woman who has had more than one terrible relationship. Her focus for years has just been her career. Why do you think she enjoys coming to visit? My friendship, but... To be honest, she's always loved spending time with you. And not because she thinks of you as a child. She's always considered you a wonderful young man."

"I had no idea she cared."

"All my friends do. They all adore you, John."

"That's... That's nice to know. Thanks, Mama."

"You're welcome, sweetie. Now... It's time to get ready and your mother will be here soon. Head off to the bathroom and get ready. We'll head out soon."

I did as she asked. A hot shower. I shaved and put on some deodorant and a little cologne. Selected a nice dress shirt and pair of trousers. Good pair of shoes. Standing in front of the mirror, I thought I looked pretty good. Walking out into the living room, Cassandra wasn't ready yet which is something I did expect. There was a knock at the door, answering it to see my mother looking as resplendent as I'd ever seen her.

"Happy birthday, baby!" she exclaimed before I opened my arms, Mum giggling as I held her tightly to my chest, "My little boy is now a man."

"I love you, Mum," I whispered. That made her cry for a few seconds as it had taken me a long time to tell her that I still loved her even after everything. I'd never blamed her for the issues she faced. I knew signing those papers had broken her heart, but it was the best thing for both of us.

"I love you too, baby," she whispered back, feeling her fingers caress my back, "I'm so happy now that you're in my life all the time."

"I love knowing that you're now in a good place, Mum. I'll stay with you next week like I always do."

"Is it weird that I want to snuggle when we go to sleep?"

"I think it's just making up for the years we were apart, Mum."

Cassandra walked out and I couldn't help whistling as she was looking as sexy as ever. She blushed slightly before I hugged her, feeling her body mould against mine. She then greeted Mum with a hug. and I adored seeing the two sisters were still so close. Cassandra had never been negative towards my mother, explaining over the years her issues. She certainly helped keep the flame of love alive for my mother. Another reason why I loved Cassandra so much.

"What about your friends?" I wondered.

"We'll be meeting them at the restaurant. We'll have dinner, wander towards a nearby bar, then we'll hit up a club for the first time in your life. And if you play your cards right, you'll have over half a dozen middle-aged women eager to dance with you."

"Definitely dancing with my handsome young man," Mum stated, looking at me with the unconditional love that had always been evident in her eyes, even during those dark days.

"There's going to be a line, that's for sure," Cassandra added with a chuckle.

Dinner was at an Italian restaurant. As far as I was concerned, you could never go wrong with Italian food. There would always be something on the menu for everyone. The other women were waiting for us to arrive, all of them looking as beautiful as I could imagine. They all greeted me with a tight hug and kiss on the cheek. By the time Nancy was ready to greet me, I was already hard. When she pressed her body against mine, I just knew she felt it. When she leaned back and met my eyes, a smirk appeared, and I felt myself blushing.

"Just remember that I'm a single woman when we hit the dancefloor tonight, John," she told me, "And dancing with a woman can be considered foreplay."

"Behave, Nancy!" Mum exclaimed though she was laughing, "That's my little boy."

"He's far from a little boy now!" Charlotte retorted, "It's why we're here, right?"

"He is definitely not the little boy I remember adopting," Cassandra stated with pride, immediately wrapping an arm around the waist of her little sister, "And he's fortunate enough that he has two mothers that love him more than anything."

Dinner was as fantastic as I expected as it was somewhere Cassandra would take me for a treat, particularly if I'd performed well in classes, and more than once she'd taken me after my rugby league team had pulled off a fantastic result. It was also the same restaurant I had dinner with my mother for the first time after my adoption. I had a lot of good memories of the place and was glad Cassandra knew me so well.