My Aunt's Best Friend

Our next stop was a nearby pub, the usual boozer seen around Sydney. Most have been renovated over the past few years, turning them from the dark, dank, smoke-stained pubs into places that are bright, vibrant and places where people would want to stop for a drink. Although it was my birthday, I approached the bar, eager to buy my first drink as an adult. I wasn't surprised that I was carded, and then offered to buy a drink for all the girls.

"Buy one for your mothers," Nancy stated, "We'll get the next few rounds anyway."

Mum gave me one hell of a kiss when I handed her a soft drink, as she'd been sober and teetotal for a few years. She knew she could have a drink if she wanted, as she could handle it, but didn't want to on my birthday. Cassandra happily took the glass of wine I'd bought her while I had an alcoholic ginger beer.

There wasn't any loud music, so it was easy to talk to all the women with me that evening. They were all interested to hear about my studies, my ambitions, my hopes for the future. When asked about any potential love interests, I definitely blushed again before I took a deep breath and admitted quite bluntly that I felt hopeless when it came to girls. I didn't expect to be hugged tightly by a pack of beautiful mature women.

"Tonight is your lucky night then," Emma stated, "Every man is going to be jealous when you rock up to the club with all of us in your company."

"And you haven't been that tongue-tied with us tonight," Isla added, "The perfect gentleman, John."

We enjoyed a couple of drinks, Mum eager to buy me a drink for the first time. I didn't force her to buy a drink for herself, aware of her struggles. She was happy to sip at a soft drink or a juice though no one missed that she spent most of the time sitting as closely to my right, holding my hand on occasion, as happy as I could remember. Cassandra would give me a hug every so often, making sure I was the centre of attention and conversation most of the time.

Leaving after a couple of drinks, there was only a short line to enter a nearby club. I was carded again before entering. After I was handed another drink, Cassandra told me that everyone would want at least one dance with the birthday boy, Wendy adding that they'd all been to this particular club numerous times as it played good music, the sort where they would generally play a lot of slow songs throughout the night.

Mum was the first one to drag me onto the dancefloor. When a slow song started to play, I wasn't exactly sure what to do, but when she pulled me closer and she hugged me as we swayed, I wrapped my arms around her, feeling her rest her head against my chest.

"I'm so glad you're in my life all the time, John," she whispered.

"I never blamed you, Mum. It's okay. Cassandra always explained things to ensure that I never blamed you."

"And your father?"

"Well, considering he hasn't been in my life for a number of years, I'm sure you can figure out my opinion of him. You never disappeared from me. You've done so much to turn your life around so we would still be as close as we could."

Cassandra was next to dance with me, unable to stop smiling the entire time as I managed to twirl her around the dancefloor a few times. I'd thanked her more than I could remember for giving me a safe and loving home when she adopted me, and I did so again. As soon as the next slow song started, she moulded into my body and I knew she was having a little cry, hearing her whisper how much she loved me, how proud she was... Almost enough to get me going.

Her friends were lining up to dance with me by now. Each of them smiled and laughed as we enjoyed at least two or three songs together. The number of compliments I received had me blushing constantly. I simply wasn't used to hearing such things. Sure, the girls at my school were all my friends and were always nice to me, but that was different from some very attractive, mature women.

Nancy was the last one to dance with me. I had a feeling she set it up that way as my crush on her had probably been obvious for the last couple of years. We enjoyed a couple of fast songs as we both laughed as were just being silly, but as soon as a slow song started, she looped her arms around the back of my neck and pulled herself as close to my body as possible.

"You can touch me, John," she said, her eyes gazing up into mine, "If you want to caress my bum, for instance."

"You serious?"

"John... I'm going to ask you a rather blunt question. Are you a virgin?" I know I blushed, but I still managed to nod that I was. "You know I've been single for a while now after everything that happened with Dave. Focused on my career, my friends and my family. And I've seen you develop into the wonderful young man who is now touching my butt."

"You offered..."

"Does it feel good?"

"Yeah."

"I like what I can feel right now."

I felt my cheeks grow ever so hot as I'd been getting harder and harder with each friend that I'd been dancing with. By the time Nancy was pressing her body against mine, to say I had a raging erection would be correct. But when I noticed she was smiling at me, and kept her body pressed against me and it, I figured that it wasn't anything I should be too embarrassed about.

"John, I'm going to be serious for a moment. I know you have a crush on me. I'll admit to being rather flattered that a young man your age would be that interested in a woman my age and with some of the baggage that I have..."

"You're not that old, Nancy."

"I'm closer to forty than thirty, John. I'm double your age and a bit."

I took a deep breath and said, "And I think you're beautiful."

Her face softened immediately, and a beautiful smile formed. I have no idea where I found the courage to say those words, but I was glad that I did. When she leaned up and left a soft kiss on my lips, I think she realised within a couple of seconds that I'd never been kissed before as I had no idea what to really do. She leaned back, that same smile on her face before she told me exactly what to do.

It took a couple of go's before I figured out what to do, but once I did, Nancy's hand was soon resting on the back of my head as I felt her tongue slide into my mouth. And I think I nearly creamed my underwear at the same time, I was so bloody excited. When we finally parted, I'm sure that I looked at her in a state of shock while she continued to smile rather happily at me.

"John, I'm not going to stand here right now and state that you will end your birthday no longer a virgin, but if you would like, I can do one or two things for you when you get home. Would you like to come home with me?" I think I nearly fainted as she immediately added, "I've already talked to Cassandra and your mother about this. They have no problem with the idea."

"You have? They don't?"

"No, they don't. And Cassandra is my best friend. I'd never do anything like this without her approval. She knows..." Nancy paused and lowered her eyes. "She knows that I've been a little lonely. She also knows that you have a wonderful heart, and she thinks that we might even be good for each other."

I met her eyes, and I leaned down to leave a soft kiss on her lips. "Okay," I whispered.

Taking my hand, she led me off the dancefloor back to everyone else. I was greeted by a sea of smiles as I'm sure every single one of them didn't miss the fact that I had my first ever make-out session. The fact it was with Nancy was nothing short of a dream come true.

"Are you coming home with us?" Cassandra asked once I had a new drink in hand.

"Um... No, Mama. Um... I think I'm going..."

Mum started to giggle next to me as Cassandra gave me a hug. "Have fun tonight," she whispered into my ear, "Just don't rush things, okay? I love you and I love Nancy. Age gaps mean nothing when I simply know that you're going to be right for each other. She'll show you the ropes and I know you're going to give her the love she needs in return."

We stayed for another hour and I enjoyed a couple more dances before we agreed to leave as it was getting late. Nancy made sure she was holding my hand as we walked out into the cool night air. After I was hugged and kissed by everyone else, including a very long cuddle with Cassandra and Mum, it left Nancy alone with me as we took one of the last taxis in line.

She didn't say too much on the way back to her place though her hand never let go of mine, occasionally glancing my way and smiling. I just felt nervous as I was wondering what she planned for me. I went over all the possibilities and knew it could be something simple like just seeing her naked, or I might even get a blowjob, or she'd want me to do something for her.

Leading me inside her house, which I'd visited before with Cassandra quite many times. It was tastefully decorated, and I knew it was a home that she'd bought with her ex-husband several years previously. She'd taken full ownership after their divorce. I still remember what happened and the fallout of his affairs. I remembered Nancy coming to visit Cassandra more than once, spending half the night in floods of tears on the couch.

I also remembered that I would sit next to her and occasionally give her a cuddle, and she would thank me each and every time that it made her feel a little better.

"Would you like a drink, John?"

"Sure, I'd love one."

"I noticed what you were drinking. Care for something a little different? I'm partial to a little whiskey and mixer."

"I'll give anything a try once."

She smiled and walked towards me, resting her hands on my chest before leaning up to leave a soft kiss on my lips. "Take a seat and I'll come back with a drink for us," she said softly.

She was gone for longer than I expected as she returned with a glass in each hand, wearing a silk robe that barely covered her arse and she had definitely tied it up in such a manner that showed off some of her cleavage. Taking the offered drink, I immediately took a sip, not missing the fact my hand was shaking. Nancy didn't miss that either.

"I know you're nervous, John," she said after placing her drink down and taking my hand, "I'll put it bluntly for you. We're not having sex tonight." She paused and leaned over to kiss my cheek. "But we'll be having sex later."

"Really?"

"I just want to have some fun with a young man who I know cares for me a great deal. Can you handle the fact I'm in my late thirties though? I'm not a slim, perky young girl, John. I haven't had kids, but I still, you know..."

"Are you naked under the robe, Nancy?"

"I am, sweetie. Want to see me?" Nodding eagerly made her chuckle as she stood up in front of me. Undoing the tie around her waist, she let the robe fall off her shoulders first, smiling at me as she let it slowly fall down until her breasts were exposed. I knew she was probably worried, but they were perfect in my eyes. Just a slight droop, very pink nipples, no missing her excitement as they looked rather hard. Letting the robe continue to fall down, her tummy wasn't toned but I thought she had nothing to worry about before she finally let the robe fall to the floor and I saw her pussy for the first time. She had a patch of blonde pubic hair above her pussy.

"What do you think?" she asked softly.

"I nearly came..." I admitted.

That made her chuckle as she lowered herself down to straddle me, resting a knee on either side of my body. Unsure what I should do with my hands, she took the drink from my right one to place that down, sitting down on my rather obvious erection and I couldn't help the groan. Taking both of my hands, she smiled as she placed them directly onto her breasts.

"Explore my body, John," she whispered, "I'm going to teach you everything you need to know about pleasuring a woman. Tonight, though... I'm going to give you a blowjob."

"I'll probably last a minute."

"You'll get more than one."

I met her eyes and I had to ask, "Why?"

She leaned down to kiss me as I moved my hands from her breasts to wrap my arms around her. I felt her snuggle and felt her sigh. "Because you are a wonderful young man. And Cassandra... She knows you're terribly shy at times. And she's never been oblivious to your crush on me. When she told me everything, I knew what I wanted to do." She paused and leaned back enough to meet my eyes. "And, I'll admit, there is an element of proving my own self-worth, the fact I have a handsome young man so eager to be with me."

My hands explored her body for a few minutes. I loved feeling up her breasts. I savoured how soft her skin was. I adored playing with her butt, making her giggle when I gave each cheek a good squeeze. And when she told me to touch her pussy, I met her eyes and she nodded firmly. Running my fingers through the tuft of pubic hair, I ran a finger along her slit and was surprised to feel that she was wet. Sex education was good enough to explain everything that happens to a man and woman when aroused, but theory is one thing, practice is another.

"I'm a little horny," she whispered, "I'm going to blow you, John, then I'm going to put on a little show and masturbate for you. We're going to take things nice and slow because I want to make sure that you learn." She then leaned down to kiss me. "And while I teach you about sex, I want to take you out on dates as well."

"What if, you know, I wanted to date you for real?"

A beautiful smile formed. "John, we will be dating for real."

"Oh..."

"It's just... When you attend university, and you're surrounded by all these beautiful young girls, will you really want an old woman like me?"

"Um... Nancy... When I watch, you know, porn... I prefer the mature women..."

She gazed at me in silence for a few seconds before she chuckled. "I know about your crush on me. I'm guessing you think all of Cassandra's other friends are hot too?"

"You were always my favourite, Nancy. But I won't lie and say that I don't think they're all hot."

Sliding off my lap, I knew I stared at her naked body though Nancy didn't appear to be self-conscious at all. Offering her hand, she helped me up and started the slow process of helping me undress. First was my dress shirt, not missing how her fingers caressed my naked back and chest. I was no muscle-bound jock, but I kept fit and ate right. Lowering herself to her knees, she slid my shoes and socks off before running her hands up my legs to the belt around my trousers, then undid the button and lowered the zipper.

Standing in front of her in just my boxer briefs, it was obvious how hard I was as her fingers softly ran over the tent. I groaned and nearly came again as she slowly lowered my underwear, so I was left as naked as she was.

"Oooh, that's a nice one, John," she whispered, "And it's so hard for me too. I don't think my ex-husband was ever this hard for me. Now, I do wonder if I wrap my hand around it that you're probably going to cum, right?"

"Probably," I murmured, "Sorry if I cum quickly."

"I don't care, sweetie," she said with a smile, "You're young, virile, and I bet you'll probably stay hard all night no matter how many times I help you cum. Why don't I get your first lot of cum out of the way before I give you a blowjob?"

"How do you mean?"

"I'm going to stroke you off so you cum on my tits. I'll get a washcloth to clean up, then I'll give you a blowjob. And I'll swallow what you give me, John, because that's what I want to do for you." She stood up for a moment and kissed me softly. "Want me to be your girlfriend?"

"Seriously?" I asked, unable to hide the excitement in my voice.

"Until you tell me that you've met a girl your age, I'll be your girlfriend. I want to do this for you, but also for me, John."

What I didn't expect was for her to spit on her hand before wrapping it around my cock. I groaned straight away as she talked dirty about how big my cock was, how much she wanted to take it in her mouth, how much she wanted to taste my cum, how she knew it was going to feel when I buried it in her hot, tight pussy...

I probably came within sixty seconds, coating her breasts in so much cum, she couldn't help but giggle as she milked my cock dry before she sat back and smiled up at me.

"Take a photo, John. It's okay."

"Really?"

"I want your phone to be full of photos of me. But you cannot, and I repeat cannot, show any of your friends."

"I'd never..."

"I know you wouldn't because you're a sweet young man, but your friends will probably figure out that you're seeing someone in the end. Keep any naughty photos hidden. I'll send you some other non-naked selfies though so you can show off your mature girlfriend."

After allowing me a couple of photos, she disappeared to grab a wet washcloth, handing it to me so I could wipe off the cum all over her breasts. We then shared one hell of a kiss, her body pressing into mine, and I don't think either of us was particularly surprised that my cock remained rock hard.

"I'll get on my knees for you again now, baby," she said softly, "Do you want to stand up or be sitting on the couch?"

"What will be better for you?"

"On the couch so it's easier for me to gaze into your eyes. And you should use your hands to play with my hair. Tell me what you're thinking and feeling. Let me know how good it is. Tell me what you're otherwise imagining."

Sitting back on the couch, I spread my legs wide enough so Nancy could comfortably sit between them. She leaned up to give me a soft kiss before she kissed down my chest and down towards my cock. I kept my groin neat and tidy, her fingers wrapping around the base as she ran her tongue up the underside of my cock, her eyes never leaving mine as she continued to lick it for a little while.

"Ready, handsome?" she asked.

"Hope I last longer!"

"You will. And you're going to love it. I promise you."

Feeling her soft lips wrap around my cock had me groaning and moving my hips almost involuntarily. She ever so slowly lowered her mouth until she had a few inches inside it, not wasting time in slowly bobbing her head up and down. One hand worked the rest of my shaft while her other hand caressed my chest, making her smile when I took her free hand and gave it a kiss before I held onto it.

Watching Nancy with my cock in her mouth was the stuff dreams are made of. Only one of many fantasies I'd had about her. Her eyes continued to gaze lovingly up at me as her head bobbed faster and faster, running my fingers through her hair just as she asked.

"Good boy," she said with humour, "Just let me know when you're going to cum so I'm ready for it."

"Okay," I murmured.

One hell of a birthday present, having the older woman I'd been crushing on for a couple of years to be sucking my dick. And I knew that I would want to return the favour eventually. I'd always thought about going down on her, tasting her pussy for the first time. And I'd often closed my eyes when jerking off and thought about making love with her in various positions.

It didn't take too long before I felt those familiar sensations that suggested an orgasm was imminent. What I didn't expect was to see that Nancy really seemed to be enjoying herself. I'd always been told that most women hated giving blowjobs, but there was a look of near delight in Nancy's eyes. I told her how beautiful I thought she was. How hot it was what she was doing for me. What I wanted to do to her later. How much I wanted to eat her pussy. How much I wanted to just kiss and lick her body. How much I wanted to lie her down and make love to her.

Then I warned her that I was about to cum, and it was only a few seconds later that I groaned and exploded in her mouth. Nancy hummed happily as I felt her tongue working my shaft and I could hear her swallowing down my cum. Again, I'd been told that most women hated taking cum in their mouth and swallowing, but Nancy seemed to be ever so eager.