Unexpected Anal for Lilly's Friend

** All characters in this story are 18+ and all actions are consensual **

It was probably an understatement to say that I was very pleased with myself following the deep ass-plowing that I had subjected Lilly to a few days earlier. In fact I couldn't help but feel proud that Lilly's first ass fuck had clearly impacted her, after seeing her walk down the street yesterday in a way that suggested her tiny hole was a little raw from the experience.

So with the very fresh memory of having my full 8 inches fully swallowed up by Lilly's tight little ass, I was looking forward to when it might happen again.

Of course it did occur to me that Lilly may not be as keen if her anal sphincters where still feeling sore from the first cock workout, but as it turns out another great opportunity was about to present itself.

That Friday evening it was quite hot so I put off my usual evening walk until quite late. In fact it was after 10pm when I finally decided that it wasn't going to get any cooler so I should just go ahead an do it, expecting that my usual route would see me home at around midnight.

I had barely stepped out the front door when I heard the distant sound of splashing along with giggling female voices, and as I continued down the driveway I realised that this was coming from Lilly's backyard. Curiosity and perhaps just the thought of seeing Lilly's amazing tits and ass in a bikini got the better of me, so I walked across the street and down the pathway that ran along the side of her house.

At 18 years old Lilly still lived with her parents, but I noticed that their car wasn't in the drive. A quick look over the fence confirmed that the only souls in the yard were Lilly and another girl, who I couldn't see properly from my current vantage point.

I decided to invite myself in through the side gate and then casually strolled up to the pool decking and cleared my throat.

"Hi Lilly. It's a bit late to be making this much noise isn't it?" I said in an only half-serious tone.

Clearly the girls didn't see or hear me enter the yard. "Oh my God Mr Andrews!" Lilly almost screamed. "You scared the crap out of me!"

For a moment I smiled to myself and wondered if that was a reference to our recent encounter where I 'fucked' the crap out of her, almost literally.

"Oh sorry Lilly, I didn't mean to scare you and your friend. I was just out of a walk and heard you guys in the backyard, so thought I might come and say hi."

Lilly and her friend broke into laughter. "Oh that's ok Mr Andrews, but sorry my parents aren't home tonight at all."

It was at this point I realised that the girls had clearly been enjoying their evening with a few drinks so I turned my attention to Lilly's friend. She was standing in the middle of the pool wearing a pink bikini top that pushed out a perky set of breasts that where much smaller than Lilly's but still quite 'grab worthy'. Remembering to look up from her cute tits, I could see this girl had light brown hair that ran just past her shoulders and overall she appeared to be much smaller in stature that Lilly but more athletic.

"Oh well that's ok but ummm who's this?" I asked pointing to the pink bikini beauty in the water. Once again the girls giggled and I couldn't help but notice how Lilly's chest shifted in her blue bikini top.

"Oh sorry, how rude of me" Lilly said in a comical, over dramatic voice. "This is Jayde Mr Andrews. Oh and in case you're wondering she is the same age as me."

As Lilly finished her introduction Jayde stepped up out of the pool allowing me to take in a full view of her small but well built body, but as she moved towards me she suddenly stopped, turned around and bent over to pick something up.

My eyes nearly fell out of their sockets as I was presented with Jayde's tiny bum clad in a wet bikini. It was clear that her ass was even more petite that Lilly's and it looked very firm. I didn't ask but assumed that perhaps she was into dancing or running based on her ass alone and wondered if it would even be possible to invade it the same way I had with her friend.

Jayde stood back up, now with a towel in her hands and continued towards me wearing an alcohol inspired smile on her face.

"Nice to meet you Mr Andrews. Lilly has mentioned you to me a few times actually" Jayde said barely managing to not break into a giggle.

I wasn't really sure what this meant so played it safe in my response. "Well she's been helping out with some babysitting so I guess she's managed to get a few dollars out of me" I laughed.

"Sure that's good for Lilly" she laughed, "but how do I get a few dollars out of you?"

Again, I still wasn't sure if she was just being silly or if she knew of my recently activity with Lilly.

"Ahh well I'm afraid that I only need one babysitter" I said, motioning to Lilly. "But you know there are plenty of ways of earning a few dollars so I'm sure you'll do just fine when you find something."

I sensed that perhaps I'd saved the conversation from getting too awkward too soon as both girls giggled at my response and then invited me to join them beside the pool. Jayde momentarily stepped away to get some fresh drinks from inside the house and I quickly found myself alone with Lilly again.

"So Mr Andrews, speaking of making money. My ass it still kinda sore from the other night but ummm maybe you can help with that?"

Well that comment was enough to take Jayde's tiny ass of my mind and I didn't delay with my response.

"Hmmm well if your friend is going home soon I'm sure there's something we can do" I said, being mindful that my wife would be expecting me around midnight.

"Ohhh goody!" Lilly exclaimed excitedly. "Jayde was just going to stay for another drink and then shower and go home. How does that sound?"

"Perfect" I responded, momentarily imagining Jayde's firm little body naked in the shower.

Jayde returned with drinks, still wearing only her bikini. Sitting across from her I enjoyed my beer with taking in the view of her cute breasts that barely moved when she laughed.

After around thirty minutes Lilly stood up and said she was going to go and have a shower and get changed. Jayde took this cue and said she should get going but would also go and have a shower before heading home.

After enjoying the view of the two girls' bums as they walked back towards the main house I was left alone to finish my drink. Deciding this wasn't much fun I waited a minute and then also walked back into Lilly's house thinking I might be able to pay attention to Lilly's ass a bit sooner than planned.

Having known Lilly's parents for quite a few years I was no stranger to this house. Figuring that Jayde would be taking her shower in the guest bathroom I headed towards the main bathroom, hoping to find Lilly naked somewhere along the way.

As I entered the bathroom the shower was already running and behind the frosted shower screen I could see Lilly under the water stream, facing the shower wall.

Seizing on this opportunity I slipped off my clothes and moved towards the shower, hoping to give Lilly an unexpected surprise. My cock had already risen to full standing attention in anticipation of having her tight teen rectum wrapped around it.

Opening the door to the shower I was greeted with an outstanding view of a wet teen body from behind...but it was Jayde, not Lilly!

As the shower door closed behind me I didn't have a moment to think, and before I knew it Jayde had turned around, her eyes moving directly to my 8 inch cock pointing at her cute bare tits.

If felt like a full minute went by without either of us saying anything...just staring.

Standing right in front of me this petite 18 year old's head was level with my chest, in fact I felt like I could have almost touched the nipples on her small breasts with my cock as I towered above her.

My hardness wasn't going to go away any time soon, so I moved to take advantage of the situation, hoping it wouldn't end with Jayde running from the bathroom screaming.

"Uhhhh ok so I was hoping to run into Lilly...but ummm wow Jayde...you're quite the perfect little package." It was the best I could do caught out in the moment but thought that it might be well received by the teen after a few drinks.

Jayde still stood quietly, her eyes moving quickly between mine and my rock hard cock, so I continued as the water ran over her body. "Well you asked before how you could get a few dollars out of me...and now that I'm standing her I have some ideas, so how about it?"

Jayde seemed to relax taking just half a step forward and looking directly at me. "Umm hehe I guess that might be ok but errr what it depends what you want to do."

I knew time wasn't on our side and had to be more direct to get things moving.

"Jayde you just have to do everything I want you to for the next fifteen minutes and I'll help you out with five hundred bucks ok?"

This girl may have been super cute, but I could see that she was also quite green and perhaps didn't think about may follow. She nodded her head. Lucky me.

With the water still running I placed by hands on Jayde's shoulders and directed her down. "Get on your knees and open your mouth. I'm going to fuck your throat first."

As Jayde knelt down in front of me I realised that I'd have to bend a little to bring my cock down to her waiting open mouth. I couldn't help but think how different she felt compared to Lilly as her mouth struggled to stretch around my swollen rod. It didn't take long for the head of my cock to find the back of her throat and cause her to gag.

"Hhhhhggggh huuurg heh aaack." I loved the sound of Jayde struggling with the throat fucking she was receiving. I almost served up a load of cum as I continued to pump her mouth while holding her roughly by her hair as she looked up at me was watery eyes, but her mouth was not the target I had in mind for my cum.

Satisfied that I'd done enough work on her little mouth and throat I took her by the hands and pulled her up to her feet again. "Turn around" I growled.

I took a brief moment to really appreciate the size and build of this willing 18 year old's body as I pulled her back against me so my cock rested on her back. I moved by hands up to cup her small, firm breasts and then moved down to hold her even firmer ass cheeks in my palms.

For my next move, the shower water was going to be in the way so I reached forward and turned it off, grabbing a jar of coconut oil from the shelf near the tap. This would be just what I needed to get the job done.

I felt Jayde tense up where she stood. "Ummm what are you going to do with that?" she asked. "My pussy is already pretty slippery if you want to put your dick in there Mr."

"No, that's not what I want Jayde. Reach back with your hands and show me your cute little asshole now please."

Not saying anything my new shower slut moved her hands down to her ass cheeks and spread them for me. I dropped to my knees for a closer inspection, opening the jar of coconut oil and coating a finger with it at the same time.

"You're going a great job Jayde" I said as I pushed my index finger into her rectum without and warning.

"ohhh hmmm owwwwww eeeeek hehe" she squeaked as my finger bottomed out at the second knuckle. "oh owwww ahhh eeeee my ass!"

Knowing that I didn't have much time I was going to have to move things along much quicker than when I look Lilly's ass.

"Are you ok to continue Jayde?" I asked as I quickly worked a second oil coated finger into her incredibly tight anal cavity.

Still wiggling somewhat in discomfort, Jayde remained compliant and consented to the advancement of my fingers. "Ohhhh jeeeez ugggghhh hmmm hmmm fuck fuck ...ohhhh kaaay uhhhggh."

Well my visit to Lilly's house was just about to get a whole lot better. just 10minutes earlier I was ecstatic at the thought of burying my hard dick in the bowels of Lilly again, but instead I was about to do the same to her smaller, tighter friend.

I pulled my fingers from Jayde's anus and then stood up, coating my hard, throbbing cock with a generous helping of the coconut oil. Pushing this tiny 18 year old slut hard against the shower wall I positioned my cock carefully against her virgin rosebud...and then pushed.

Unlike my anal encounter with Lilly days earlier I didn't give Jayde the opportunity to get used to the girth of my cock as her sphincters opened up around it, or allow her to take an inch or two or three deep and slowly work deeper. Instead I pushed into the tiny ass of this hot teen with no mercy, using my full weight against her petite wet body to bury the full 8 inches deep into her ass in one thust.

"ahhhheeeeeeeeeee!" Jayde screamed in surprise, and probably pain, just a little too loud. "Oh fuuuuuuuck...oh fuuuuuck my assssssssss!"

It wasn't what she meant but I was happy to oblige. "Yeah I'm gonna fuck your ass now honey" I grunted in her ear as I held her against the shower wall.

As I pulled almost the full length of my cock out of this girl and then shoved it back in roughly over and over again I almost couldn't believe how much tighter her ass was compared to Lilly's. Perhaps it was because her ass was still trying to come to terms with what was happening, but every thrust was a real effort, even with the extra oil I'd used. The tight, warm, vice-like grip of Jayde's teen ass was simply heaven.

After about only thirty seconds Jayde was clearly having trouble standing up under the anal attack she was receiving, but I wasn't yet finished wrecking her ass. With the girl fully impaled on my cock I spun her around and lifted her up and out of the shower recess and found a space for her to bend over the spacious bathroom sink.

With Jayde now face down, bent over the sink bench I continued her ass drilling, adding the last of the coconut oil I'd found in the shower. Moving more smoothly in and out of the teen's stretched back hole, she appeared to have grown more comfortable with my backdoor invasion, but for me her ass was still the tightest thing I'd ever wrapped around my cock.

Looking up from the view of my slick cock stretching her greasy tight asshole I realised that this position also came with the benefit of seeing the look on Jayde's face in bathroom mirror. Her eyes closed tightly each time my cock bottomed out deep in her bowels, and then opened widely as I pulled out all but the last inch.

"Ohhhhh ummmphhh uhh...fuuuuck" she quietly groaned as my gaze moved back to my cock engulfed by her cosy, swollen little ass.

I slowed the pace of my thrusts, enjoying the sound of Jayde's deep breathing and continued whispered grunts, accompanied by the juicy slurping and slapping noises caused by the repeated invasion of her oily, tight hole.

It had now been almost fifteen minutes since I'd embarked on my dirty bathroom adventure with Jayde and while I could have probably gone another fifteen with her bent over the sink, it was time for my final move.

Once again stopping with my cock completely swallowed by Jayde's smallest hole I pulled her up from her bent over position and dragged her back a few steps so I could sit on the stool by the sink. Closing my legs so hers dropped either side of mine she was now fully impaled on my cock under her own weight as she couldn't quite reach the floor.

"Uhhhggg hmmmpppffff" she grunted, taking a moment to take in her new uncomfortable position on my lap, with 8 inches of cock up her ass fixing her in position.

Which my rod now parked still deep in her ass, my hands were free and reached around to finding her tits and dripping pussy.

"I'm gonna cum in your ass now...but I want you to cum too" I whispered in her ear as I squeezed one of her small firm breasts.

My other hand went to work fingering her wet pussy and rubbing her clit, causing her to moan loudly and slightly relax the sphincter muscles gripping my cock.

"Hmmmm hmmmm fuck...owwww...hmmmm" cooed Jayde as I picked up the pace on her clit with my fingers and rocked a little forward and back to remind her of the blockage in her ass. "Hmmm ahhhhh yessssss eeeeeeee" she cried and I felt her ass clamp down even tighter around my cock.

This was my trigger point and I grabbed her tits with both hands and pulled her down hard on my already balls-deep cock in her teen bum, unloading a well deserved load of cum into her stretched out bowels.

Waiting a moment for her ass muscles to stop contracting from her climax I cupped her bum cheeks and lifted her off my still hard cock with a wet pop.

"Hmmm you'd better suck that clean honey" I said, quickly grabbing her hand and spinning her around to face me, guiding her mouth to my coconut oil covered hardness.

I wasn't going to cum again, but I did want to hear her choke on my cock once again while getting it clean so I could get dressed.

"Ackkk uhhhhhk...ugggghhh." Once again Jayde struggled with both the thickness and length of my cock in her mouth and if anything made even more of a mess with her drool after just a minute of throat fucking her again.

Having achieved more that I could have hoped that evening I pulled out of her mouth and promptly stood up to retrieve my clothes, leaving my new anal conquest now kneeling on the floor.

As I folded up some hundred dollar bills and placed them on the sink I said "Tell Lilly to let me know when you're around again. I'd like to get you two girls in the same room."

With that I walked out of the main bathroom and headed for the second bathroom to find Lilly.