Aunt Penny Pays a Visit Ch. 05

Monday: Day 5

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I could hear Cindy honking again, as I rushed out of the house and onto the driveway.

"Ah finally. There you are Penny! What took you so long? " Cindy yelled over the sound of her car's running engine.

"Sorry Cindy, I uh.. totally forgot about our catch up today." I said sheepishly.

"So, I take it things must have gone well with the nephew?" Cindy grinned.

Cindy and I have been best friends since highschool. So, needless to say, when I started crushing on my hot nephew, she was the first and only person to know about it.

I knew I could talk to Cindy about something so taboo. Her non judgmental and care-free personality naturally nudged me to pursue my relationship with Nick.

When she found out that Nick asked me on a date 3 days ago, she jumped at the opportunity to take me out shopping for an outfit for the night and multiple pieces of lingerie. She was definitely a woman with foresight.

As I closed the car door, Cindy was still looking at me, eagerly awaiting a response to her question.

I kept silent and simply gave her a shy smile.

"OH MY GOD YOU DID IT!!" Cindy celebrated.

"And you fucked on your first date?? What a slut!" she smirked.

"Sshhh, Yes we did, now lets get a move on before Nick hears us. We promised each other to keep our relationship a secret." I said sternly.

"Fine. Fine, you're telling me all about this over lunch." Cindy giggled.

On the way into the city, I told Cindy what a perfect date I had with Nick. The flowers he bought for me, my favourite food he ordered, and that canopy he built in his room specifically for our first romantic night together.

"My, my, my. It sounds that he really likes you! I thought you just wanted to fuck him but now it seems you've charmed him a bit too much. I'm soooo jealous!!" Cindy said as she weaved in and out of traffic in the busy cbd.

Cindy and I are both single mothers of daughters about the same age, and we lost our husbands shortly after marriage (I lost my husband to cancer while she lost hers to another woman).

After her divorce, Cindy focused on her career at a busy law firm and made partner on her 40th birthday 3 years ago.

She is a successful, intelligent and kind woman and a fantastic mother -always putting her child's interest above her own. Hence, she remained single after her divorce to juggle caring for her daughter, Jacky and focusing on her career.

It was only once Jacky enrolled into Uni did Cindy start to date but she's not been having too much luck so far as us older women do.

We now reached the mall and found a restaurant to have some lunch at.

"So how was the sex?" Cindy enquired, causing me to choke on my noodles.

"You couldn't wait any longer before asking me that could you??" I shook my head blushing.

"Well, all I can say is, the sex was ah-mazing Cindy!" I continued.

"Give me details!" Cindy sounded like we were back in high school.

I told Cindy about how my nephew couldn't take his eyes off me (or my boobs rather) during our date, how I performed a little lapdance for him, how I got so wet I had to change lingeries, and how my nephew made me orgasm so hard with his mouth that I squirted all over his face

Cindy's mouth was wide open as I dumped all the details on her.

"Omg how did he react..to you know...the squirting?" Cindy was curious. She knew I was squirter and how most of the guys I dated in high school did not like it and neither was my ex husband a huge fan. I used to cry my eyes out to her about it. About the fact my own orgasm scared men away (men who stupidly thought I was just peeing on them- which would have also turned me on too).

"Well...surprisingly, he seemed to enjoy it." I smiled, not wanting to go further and let Cindy know that Nick tried drinking every drop of my pussy juice.

"Yaaas!! Finally a man who enjoys the fruits of his labour!" Cindy winked.

"Oh Penny, I'm so happy for you. So what now? Are you guys gonna start seriously seeing each other?" she continued to bombard me with questions.

"We did have a chat about that actually.

Nick really wants to pursue a relationship with me and I said I shared the same sentiment. I also told him how I'm looking at buying a place in Sydney or Melbourne- as you already know- and he begged me to live in Melbourne so he can stay with me when he starts Uni."

"And? What did you say??" Cindy asked.

"Well, I said I would. On the condition he dates women while at uni and not be held back because of me. I also assured him I won't date anyone, not as though I really want to anyways. Nick was a bit hesitant but said ok in the end. I guess he'll do anything to live with me hehe"

"Aww, Penny. I'm really glad things are going in the direction that both of you want. Aren't you gonna get jealous though? With him seeing other women?" I could see that Cindy was struggling to comprehend our arrangement.

"I'm really unsure. I just want him to not miss out on his youth. But what i'm sure about is, no matter what, I'll always be his aunt and I'll love him till the day I die and that won't change. Besides, we just started taking our relationship to a whole new level. Who knows what's in store for us."

Cindy looked happy for me but sad at the same time. I could tell she badly wished she was in my position and it's not as though she wasn't attractive. Cindy is a stunning asian lady. She's about 5ft 5inches tall, petite and is always well presented. She has straight black hair that stops halfway down her neck, and C cup boobs that look huge compared to her small frame. However, she has been on a few bad dates with creeps and struggled to find a decent guy to be with, or to have sex with.

"So when am I meeting Nick?" Cindy asked anxiously.

"Like I said Cindy, I made him promise to not tell a single soul about us so I wonder how he'd react if he found out I told you."

"Well, you don't have to tell him that. You can just say your best friend is inviting the both of you to her place." Cindy winked again.

"Alright, lets do something tomorrow. I might actually just speak to Nick first and be honest with him. He's not a dumb kid, he'll figure it out if he sees the way you react around us."

"Yay, I'll fire up the bbq and get some beer. We can go for a swim in my pool too!" Cindy now sounding extremely excited.

"Let me speak to Nick first and I'll confirm with you tonight." I tried to calm Cindy down.

"So Nick really liked the lingerie huh? I'm glad I picked them out for you. I knew no teenager could resist the sight of a full breasted and round assed woman like you in the ones I picked. They really accentuated your assets." Cindy giggled, still fixated on the topic of my sex session.

"Oh yes, Nick really loved them. He didn't say how much but I guess he showed me how much." I winked.

"So, do you think you're gonna expose your nephew to your all time favourite fetish- watersports?" Cindy giggled.

I really did love squirting on men, and years ago when we were drinking, I told Cindy about my ability to do so and how it turned me on. I also took it a bit further and told her that I was curious about watersports and I may even want to try peeing on a guy if he was open to it. However, I immediately changed topics as I couldn't believe I told her that and we never spoke about it till now.

"Cindy! I can't believe you still remember that. Look I was drunk that night, and...erm, I haven't thought about doing that with Nick yet." I lied.

There was something about peeing on a man that turns me on. I'm not sure if it's due to the feeling of power over another person that I derive from doing so or simply that immense feeling of pleasure I experience when releasing my urine after ressisting the urge to do so.

"You know Cindy, after you told me about your little fetish, I did some research about golden showers and it can be extremely kinky. Heck, I'd give it a go if the right opportunity arises." Cindy reassured, attempting to get me to open up to her a bit more.

"Yeah, it is. I mean, I find it kinky if only I had drunk lots of water to ensure my pee is clear and odourless. And in no way am I going to pee in a guy's mouth and kiss him later." I laughed.

"But yes, I think I can speak to Nick about it. However, I wanted to try something with him which you're an expert in." I smirked.

"Aaaah, someone wants to try anal eh?" Cindy gave me a cheeky look.

"Yes! I know you and Greg were actively into anal. Could you, you know give me some tips? I had a shower with Nick yesterday and it seemed like he was into that." I sought guidance from Cindy.

"Wait what makes you say he was into it?" Cindy cautiously asked.

"Well, he teased my anus with the tip of his penis before ploughing me in my pussy."

"That doesn't mean his into anal, but there's a few things you can do beforehand if that's the case. Follow me." with that, Cindy paid for our lunch and we were on the way to the pharmacy.

Cindy was on autopilot now, I watched her buy an enema kit- which contained a little bottle with a long tube attached to it, a pack of lube, and condoms. She seemed to have already memorised where all these items were located within the pharmacy.

Back in her car, she gave me a little tutorial.

"So, just before you have sex with your nephew next, I want you to apply a bit of lube to the tip of this tube here which is attached to this enema." she pointed at the tube.

"You're gonna squeeze the bottle and you'll feel cold liquid travel up your anus. You're gonna hold it in for about 10 minutes then use the toilet as you normally would. Next, you'll obviously want to take a shower and wash yourself up.

This is just so that when he inserts his dick in you and pulls out after he finishes he wouldn't encounter any 'surprises' on his cock. Trust me, I wished I'd known this the first time I tried it with Greg.

So, If Nick tries teasing you again, you're gonna apply a generous amount of lube around the rim of your ass and inside it. Then put the condom on him and let him penetrate you." Cindy sounded like an expert.

"But whatever you do, make sure he uses a condom cos it's freaking gross to do anal without it. And never ever let him fuck your pussy with the same condom on. Make sure he either goes from pussy to ass or or takes it off if going from ass to pussy." Cindy warned.

It made sense to me, I didn't wanna get any infections either.

"By the way, are you on birth control Penny?" Cindy sounded concerned.

"No I'm not." I giggled.

"Oh Penny, you're such a risk taker! Are you at least using protection?" she scolded.

"Look Cindy, I've got so much time on my hands now especially since my business is running on its own, with little input from me. If I do get pregnant then so be it. Besides, I would kill to have Nick's kid, the boy has good genes." I responded.

"If that's what you want Penny, I'll leave that to you then. I, on the other hand, am done with parenting. I know I won't be able to take the sound of a crying baby."

Cindy pulled up at my driveway and gave me a hug, "Alright Penny, best of luck with the enema and hopefully anal. Keep me posted about tomorrow ok hun?" She winked and gave me a kiss on my cheek.

I got out of the car and entered the house. It sounded like Nick was taking a shower.

I seized the opportunity to perform the enema on myself in my room and began the process by first getting out of my white dress and underwear.

I could hear Cindy's voice in my head as I recalled her instructions. I proceeded to apply lube on the tip of the tube and very slowly inserted it in my ass.

It was tight at first, but once I learned to relax it slid deeper into my anus. I squeezed the bottle and felt the cold liquid fill my rectum.

The urge to expel it was immediate but I held it in like Cindy instructed. Ten minutes later I headed to the toilet with a towel wrapped around me. I noticed Nick was in his room now, done with the shower.

After using the toilet and a quick shower I was now back in my room.

I reached for my phone to send Nick a text: "Hey darling, my back is a bit sore from all that walking around today. Do you mind coming to my room and giving me a back rub? The massage oil's in the bathroom."

Moments later, "Hi Aunt Penny, I've got the massage oil. Can I come in?"Nick asked as he knocked on the door.

I hid the condoms and lube in the drawer of the bedside table and spread my towel on the bed so as to not get it wet.

Lying face down and naked on the bed, I invited Nick to come in. I was already starting to get wet in anticipation of what's about to happen.

"Oh, I see that you're ready for me" my darling nephew said, as he straddled my ass and applied a generous amount of oil on my back. I could feel his 6 and a half inch penis touching my lower back and realised he was also naked.

"Oh and ditto." I said, turning my head to look at him and his scuplted biceps as he gave me a firm back massage.

Nick moved lower and now straddled my thighs to focus on my lower back. I could feel the tip of his throbbing member pressing against my anus now.

"Ohhh that feels so sexy when you do that." I moaned.

"You like that Aunt Penny?"

"Mmm hmmm. Just wait a second." I said as I reached out for the lube and condoms.

"I want you to penetrate my ass." I said bluntly.

"A-are you sure Aunt Penny? Have you done it before?" Nick nervously asked.

"Nope, and i'm sure you haven't either."

Nick shook his head.

"Good, we can learn as we go then." I smiled.

I handed Nick the lube and a condom, got on my knees and bent forward. My face pressed against the bed and arms outstretched.

Without a word, Nick proceeded to lick around the rims of my anus. "Aahh ffuck." I let out a faint moan. I was in a state of ecstacy.

His saliva dripped down to my pussy and onto the towel covered bed.

Nick then gave some attention to my pussy, giving me one of the best oral sex ever by adopting the method I taught him post date night. He licked the outer sides of labia back and forth before giving all his attention to my swollen clit.

"Fuck my ass Nick. I've been waiting too long already." I commanded him, in between breaths.

I could now hear Nick open the tube of lube.

My heart rate increasing in anticipation.

Nick squeezed a generous amount right above my anus and the cold jelly like substance dripped all the way to my pussy.

He used his index finger to spread it around my anus before gently applying some pressure to penetrate my ass with his finger.

I relaxed and could feel about an inch of his finger in me.

I heard the unwrapping of the condom and the sound of him putting it on him.

His thick 6 and a half inch cock was now begging to enter me and he pressed against my ass hard.

I relaxed a bit further and could only take maybe a centimeter of his member.

"More lube baby." I said to him and he obediently applied more.

On the second try, Nick slid all the way in me. My ass sucked him all the way in and he slowly thrusted.

"Wooww it feels soo good Aunt Penny.

Hmmm you're soo tight!" Nick exclaimed.

"Oh yes nephew, keep that pace." I moaned.

I could feel my pussy getting wet by the second. Nick started increasing the pace and before we knew it, I let out a gushing orgasm.

"Aaahhhhh...oohhh" I moaned as Nick held his position. My anal muscles contracted.

"Woah, my first anal orgasm" I was shocked to have only discovered this at 43.

"Damn, I wanted you to squirt all over my face Aunt Penny." Nick said as he withdrew his dick from my ass so that he could lap up all the juices dripping from my pussy..

"Oh yess baby clean me up." I said, turning around to lie on my back.

Nick did such a good job with my pussy and I was now ready to be penetrated.

Nick pulled the condom off and wiped his dick with the wet wipes I had in my bedside drawer.

He then penetrated my wet vagina and fucked me hard in a missionary position.

My hands roamed around his chest and biceps. Squeezing them made me even wetter. This boy was such a hunk.

Nick collapsed to my side after filling me up with his hot cum.

We were both panting heavily and turned to my side so Nick could spoon me.

His dick was semi hard and throbbing in sync with his heartbeat.

"I hope you enjoyed your first anal as I did honey." I exhaled.

"I sure did aunty." Nick said as he kissed the nape of my neck.

"By the way dear. I have something to tell you." I turned to face him.

"I know how we said we'll keep our relationship a secret. I just want you to know that I told Cindy, my best friend about us." I confessed.

"How did she react?" Nick asked.

"Cindy is the sort of person that doesn't judge Nick. Lets just say she was...very encouraging." I winked.

"Hmm..ok...As long as you can trust her, I guess I'm fine with that." Nick shrugged nonchalantly.

"Really? Oh phew! I thought you might be upset."

"Well there's nothing to be upset about. Cindy sounds pretty chill and if she's not judging us and can keep a secret, why not? I know none of my friends will understand our relationship let alone keep it a secret if I told them." Nick laughed.

"Good then, we're heading to hers tomorrow. She wants to meet my handsome hunk of a boyfriend." I said as my fingers trailing the veins on his arms.

"Yeah, I'm good with that. I look forward to meeting her. She sounds fun."

"She is, and she's a lawyer so you two might have heaps to talk about given you about to enrol into law school and all!" I was getting excited for both of them to meet each other.

"And oh, bring along your swimming trunks, she has a pool." I winked.

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