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.
