** All characters in this story are 16 older **
A few weeks had passed since I had effectively blackmailed our babysitter Lilly into giving me a hand job and I thought about it every day, even when fucking my wife. I would imagine her wet pussy was Lilly's innocent, warm hand gripping my throbbing cock and slowly sliding up and down the shaft until I would cum on her young breasts.
Now as much as the memory of that night with the drunken Lilly was great, I still had much greater plans for her. Yes, seeing her topless and having her jack me off was great, but what I really wanted was to plow her tight teen ass. Just the thought of it would get me hard at random times during the day, but the fantasy was never going to be enough.
Driving this fantasy even further was the fact that my wife simply wasn't into anal. In fact she had never even let me try and fuck her ass so I resigned myself to finding a girl who did want her ass fucked...or at least could be convinced or perhaps even tricked into letting me fuck it.
Given our recently history, that girl was going to be Lilly. She just didn't know it yet.
Actually, since the hand job incident I hadn't seen Lilly at all, but given that I didn't get any angry visit from her parents meant that she had kept the whole thing quiet so I figured there was still an opportunity to push our 'relationship' much further.
Fortunately, I didn't have to wait too long to seize the opportunity.
That weekend I headed out to the local shopping mall to grab some new shirts for work when I spotted Lilly, by herself, coming out of the Victoria's Secret store. I quickly walked up behind her and followed casually for a few steps before getting her attention.
"Hey Lilly...is that you?"
She stopped and spun around, looking a little surprised but managed to stumble out a few words. "...oh umm Hi Mr. Andrews, how are you?"
"Well, I'm great now that I'm seeing you again" I beamed. "Are you here by yourself? What have you been shopping for?"
I asked this knowing exactly what store she had just come from, hoping for the details.
"Uh well I was just picking up some new underwear...nothing exciting really." Lilly blushed slightly and I noticed a slight tremble in her slim frame.
But I knew that nobody leaves Victoria's Secret with anything that's not exciting, so I pushed her for more details.
"Perhaps you treated yourself to something nice with the babysitting money I gave you a few weeks back?" I said as I leaned forward as if to look into the bag she was holding.
Lilly returned my comment with half a smile. "Actually, I've had my eye on some silky G-string underwear that was a bit too expensive so yeah I guess that money came in handy."
"That does sound nice, show me!" I'd love to see those I said, prompting Lilly to start reaching into the bag. "Oh I don't mean now Lilly. How about you come by the house later and show them to me...while you are wearing them."
"I'm not sure Mrs Andrews would like that" Lilly retorted, but in almost a questioning way.
I laughed quietly and grinned at Lilly again. "Don't worry, Mrs Andrews and the baby are away for the weekend. Come on over, have a few drinks and show me your new fancy underwear. Perhaps I can help out with some extra cash for some other things you want too?"
Well the moment I mentioned money Lilly's eyes lit up. Clearly this was a big motivator for her and something that could also help me get what I'm after.
"Great, it's a date then...drop by at around 9." With that I flashed a final smile and went on my way, thinking of how the evening may turn out.
Just after 9pm that night I was pleased to hear a quiet knock on the front door and even more pleased to find that it was Lilly.
Not only had she had to nerve to turn up but appeared to have dressed up for the occasion, wearing a clingy cotton dress that hugged her form perfectly, highlighting her lovely full breasts, tiny waist and firm, well-shaped ass that was clearly wrapped in the new Victoria's Secret purchase. Lilly also had let her hair hang down onto her back and exposed shoulders.
"So, you mentioned something about a drink?" Lilly said as she confidently strutted through the open door leaving me and the entrance to stare at her ass as she moved. Closing the door, I quickly followed her.
"Of course, whatever you want I've probably got it" I said as I moved towards the kitchen. "Make yourself at home on the couch in the living room...I think you know where that is" I added, recalling that was the location of our previous encounter.
"Surprise me" Lilly called out from around the corner in the living room, obviously having made herself comfortable on the couch.
"Only if you promise to surprise me" I laughed back at her as I poured her a glass of sparkling wine that promised to have her feeling lightheaded in no time.
Well as I turned the corner into the living room I WAS surprised. Lilly wasn't sitting on the couch as I expected she might be but instead was standing, facing away from me having removed her dress...exposing her teen body now just covered with a satin black G-string and Bra. I wasn't sure where this new found confidence was coming from but so far I was enjoying it.
"So what do you think of my new purchase Mr Andrews" Lilly said, turning around after I had taken in her rear view and now revealing her wonderful breasts held firmly up and out by the newly acquired bra.
I was speechless for just a moment but managed to compose myself as I left my cock begin to twitch in my pants.
"Just perfect Lilly...and much better than you just showing me what was in your shopping bag" I added with a laugh while handing her the glass of sparkling.
Perhaps looking for some extra courage for this situation Lilly quickly grabbed the glass from me and made the bubbly contents disappear in her mouth in a few seconds, then placing the glass on the table.
"I'm glad you like what you see Mr Andrews, but did you ask me here to just look?" she said quite firmly. "Would you like me to use my hands on you while you with my tits again" she added, unclipping her bra and letting it fall to the floor.
"Actually, no Lilly. That's not what I want from you tonight". I could see that my statement had caught her off guard as she gave me a questioning and nervous look. "I'm looking for more than that...something I've been thinking about for a while".
"Sorry Mr Andrews...I can't let you fuck me."
She paused for a moment. "I want to save my pussy for when I have a real boyfriend but am happy to do stuff like before if you're giving me some spending money."
This came as something of a relief to me. Lilly was still willing but it was time to let her know what I wanted.
"That's ok Lilly. I completely understand but it's not your pussy I want anyway." I stepped forward up to her, close enough so her breasts where against me and reached around to her ass and gave it a light squeeze.
"I want to fuck your ASS Lilly."
The confidence that Lilly entered the house with suddenly vanished as clearly the evening wasn't proceeding the way she through it might.
"Ummm uh I'm not sure Mr Andrews...you want to put it in my Bum?"
"That right Lilly. You can keep your pussy for a boyfriend or what ever, I'll fuck your ass and you're still technically a virgin...plus you'll have a few more dollars in your purse" I said laying down a handful of hundred dollar bills on the coffee table next to her wine glass.
"I'll get you another drink while you think about it ok?".
Returning from the kitchen with a fresh glass of bubbles I was relieved to find that Lilly hadn't put her clothes back on, but was instead sitting on the couch and never eager to take the second drink from me.
Once again, Lilly make short work of the sparkling wine and placed the empty glass on the coffee table next to the couch. I could see in her eyes that the first glass of wine was starting to take effect.
Ok, I've decided that you can put it in my ass" She said at the same time putting her hands on the cash I'd placed on the table.
"But, you need to be slow and gentle and take it out if I say so...ok?".
My cock got just a little bit harder than the rock hard it already was.
"That sounds just great Lilly...shall we get started then?" I said motioning at the bulge in my pants.
"Ok, remember I've never done this...so ummm how does this work? Are you just gonna stick it in?" Lilly asked with the innocence of a true anal virgin.
Indeed, she did look a little nervous but the wine was also helping things along.
"Don't worry honey, I'm not just gonna shove it in there" I said, though I was thinking it may get to that at some stage.
"I'll help you get ready for it though. Let's start by having you take off that sexy G-string and letting me a a good close look at your tiny hole. Perhaps just lie over the end of the couch honey and let your legs hang down ok.".
"Ok Mr Andrews...like this?" Lilly asked as she lowered her G-string and lay over the edge of the couch pushing her ass out at me and revealing the wetness that was forming between her legs.
My gaze was locked on this perfect teen ass before me. I placed both hands on her ass cheeks to get my first feel of her wonderful bum. It was small and firm with each cheek fitting nicely into each hand as a spread them apart to get a better look at her small pink anus.
"Oh Lilly, your ass is simply wonderful. I'm really going to enjoy this...and I hope you do too" I whispered.
Lilly gasped as I ran my tongue over her tiny hole and poked at the entrance with the tip. Her breathing grew deeper as I continued the tight tongue fucking of her tiny ass, getting her used to the sensation.
"Oh Mr Andrews...that uh uh hmmm feels strange...but I think it's ok hmmm." It seemed that the second glass of wine was doing its job.
With that I added some lube to a finger and began to work it around the entrance to her ass hole, only just letting it push inside.
At this stage I was really showing self-control but I knew it would be worth it.
"Ohhh hmmm hehe..that feels funny" Lilly giggled as I continued the slow fingering.
Feeling Lilly relax I lubed up both my finger and then the entrance to her ass and began to push my index finger in further. Just short movements in and out but going just a little deeper into her warm, tight hole with every push until I was easily working my whole slippery finger in and out of this hot teen's ass while she panted with every push.
"Ohhhh Hmmmm owwww. Careful Mr Andrews, your finger feels so big in me...how will your cock fit in my ass?? ohhh hmmmm ahhh.".
Lilly seemed torn between pleasure and discomfort at this stage but wasn't fighting it so I continued the deep fingering of her ass by adding a second finger.
Lilly's short sharp breaths turned to grunts as my two fingers broke through her sphincter muscles, opening up her tiny, tight ass in preparation for the main event. I kept the lube flowing, enjoying the now glistening rosebud, wrapped around my penetrating fingers.
"Hhhhhmmmmpppffffttttt...ehhhhhh...ahhhhh...fuuuuck Mr Andrews...hmmmmpppffffttt" is all Lilly seemed to be able to respond with.
I wondered how Lilly would go with my full 8 inches buried deep in her ass with the way she was reacting to just two fingers.
It was time to find out.
"Ahhhhh" Lilly sighed with relief as I pulled my slippery warm fingers from her rectum. "Ohhhh Mr Andrews...that made my ass feel so full and strange. I don't think your dock is gonna fit" she said with her eyes fixed on my hardness.
"Hmm maybe you're right Lilly... but really it's up to you" I said as I picked her up off the couch and stood her up with her ass facing me as I sat down on the couch.
She looked back at me, perhaps wondering why she was standing, and I was sitting. "What do you mean Mr Andrews" Lilly said nervously.
I glanced down for a moment, admiring the lube running down her leg from her ass.
"Instead of me fucking your ass...I'm going to let you be in control...so you will fuck your own ass by moving up and down on my cock. That way you can decide how deep and how fast ok?"
It sounded like I was giving her the easy option, but I had more sinister plans in mind.
Lilly sighed with relief. "Oh ok...I guess that sounds ok...so I just sit on it like this?" she asked with an innocent tone as she moved back towards me and lowered her ass towards my now purple cock head.
"Yes that's it" I said, giving my cock an quick extra coating of lube as her tiny hole moved to swallow up my hardness.
I helped guide Lilly into a position where she could easily squat over my cock with my hands now supporting her for extra balance and she carefully pushed down.
With the finger work I'd done on Lilly the first inch slipped into her rectum easily and she moved up and down a few times with just a little more than the head of my cock in her ass. Of course, this felt and looked incredible.
I had convinced this stunning 16 year old let me open up her ass with my cock. But I knew she could do better than just an inch.
"That's it Lilly...now keep pushing down just a little more each time. You ass could easily take all of my cock, you just need to help it along by moving just a little deeper every few thrusts."
"Hmmm ugggh hhhmmmpppftt...I'll try Mr Andrews. It just feels so fucking big and full inside my bum" Lilly panted as she gave it her best effort to stuff my cock deeper into her teen bowels, getting to a point where she was moving easily up and down on about 5 inches.
It wasn't a bad effort, and it was so fucking tight that I don't know how I managed to not blow my load already, but we were so close to getting all 8 inches in I had to step in and help things along.
On her next push down Lilly paused for just a moment, struggling to lower herself any further onto my cock. I seized that moment to reach up and place both my hands on her shoulders and I pull her down on me, instantly burying the remaining 3 inches deep in her tiny ass.
I held Lilly there for a moment as she took in the reality of 8 inches of cock stretching out her teen bum and bowels.
"Aaaaaahhhhhh hmmmmpppttttfff...ohhhhhh Mr Andrewss...noooooo hmmmmmm aghhhhhh eeeeeeeeee fuuuuuck!" she screamed but stopped short of trying to get up, which to me was the signal to go for it.
With Lilly still sitting balls deep with my cock in her ass I pushed up and forward, down to the carpet, so she was now face down with me on top of her...giving me full control of the ass fucking.
Once again, the sound of the Teen's grunts filled the room.
"Uhhhgghh hmmmppppfftt...uh uh hmmmmohhhh fuuuuck" she squealed as I pumped the full length of my cock hard and fast in and out of her young, now stretched out rectum.
The feeling was better than I could have ever imagined. With just the right amount of lube I was now able to freely plow the entire length of my shaft in and out of Lilly's ass but it was still so incredibly tight with every thrust. Her groaning and grunting continued but still she did not try and break away from her current impalement.
"Uggghhhh Hmmmppptt...oooohhhuuhhhh...fuck, fuck fuck...hmmm yeahh!" It seemed that Lilly was now enjoying a bum full of cock, but I had to see this for myself.
Sitting up I moved back and slid my cock all the way out of the teen's ass, enjoying the gaping hole left behind. Lilly just lay there on her tummy still panting from my deep thrusts in her bum. I grabbed her arm and rolled her over onto her back revealing that her eyes were closed, and her mouth was wide open taking in deep breaths.
I had not paid much attention to her tits up to this point, but now I was in a better position to see and feel them during the next part of my dominance of her ass.
What I really wanted to do was look into her eyes and see the look on her face with my full 8 inches buried deep in her young ass. Taking hold of her legs I pushed Lilly's knees back towards her shoulders, then took her hands and motioned for her to take hold of her legs. Once again not only did I have a magnificent view of Lilly's glistening anus, but It now came with the added bonus of her holding her legs up as if to invite me back into her greasy tight hole.
"Hmmmmppphhh uhhhh" Lilly groaned as I pushed the entire length of my shaft past her sphincters and deep into her bowels once again.
Her eyes flicked open and her gaze was now locked to mine.
As I continued with steady deep thrusts into my young lover's ass I could see a few tears forming then falling from the corner of her eyes and she bit her lip and winced every time I bottomed out in the deepest recess of her bowels. I reached forward and cupped a breast in each hand, giving me an anchor point as I picked up the pace of my thrusts.
I had officially converted the young Lilly into my anal slut as she cried "ahhhhghhh yes...hmmmmm...yeeeesssssss!" with every balls-deep slam into her ass at an ever-increasing pace.
Her eyes had closed again, and she now wore a serious expression on her face as if she was concentrating on a difficult task.
Suddenly her eyes flicked open and she cried out once again. "Fuck meeee...Fuck my ass Mr Andrews...fuck it...fuck it...fuck it hard...pleeeeasseeee."
Well, that was enough to send me over the edge. On top of the fact that I was deeply fucking the perfect 16 year old ass of my babysitter, the daughter of my neighbor, she was on the floor in front of me, legs in the air screaming for me to fuck her tiny hole HARD. With one final push with all my body weight behind it I bottomed out once again, balls deep in Lilly's ass and unloaded what felt like a coffee cup of cum into her bowels, the pulsing of my ejaculation stretching her anus just a little more for a few seconds.
Wanting to savor the feeling of Lilly's tight back passage I pulled my cock out very, very slowly enjoying her squirming with some discomfort at the pace of the withdrawal.
"Ohhhhh hmmmpppfff...yesssss" she sighed.
After about 20 seconds my still hard cock popped out along with a steady stream of my cum from Lilly's ass. It was quite a mess...but a good one to make.
I stood up and pulled my new teen anal slut up by the arms, so she was now on her knees, looking somewhat dazed from her deep ass fucking experience. With one hand I grabbed a handful her hair at the back and gently pushed her face towards my cock, which was coated with a mix of lube, sweat, cum and juices from her ass. Though she had no experience in this area, Lilly instinctively let her mouth open and presented her tongue to my cock that was just starting to soften.
As the teen took a few inches of my dirty cock into her mouth and let her tongue dance around the base I felt my cock come to life again. Her warm lips and mouth sealed around my hardness as I gently thrust in and out with just a few inches, letting Lilly get used to the thickness.
She looked up at me with slightly watery eyes and hummed "Hmmmmm mmmmm mmmmmm" and I watched her drop a hand to her pussy and start to rub. It looked like were were both going to get off this time.
While I loved the sight of my cock disappearing into this young girl's ass, watching it move it and out of her mouth as her innocent eyes looked up at me was really getting me going so I picked up the pace and tested getting more of myself into her mouth and throat.
Lilly started to gag "Uhh oooof...ack...ack...ack" and momentarily pulled back, but with some persuasion from my hand on the back of her head she continued working my cock a little further into her mouth while still madly rubbing her clit.
After only a few minutes of having this teen slut sucking and choking on my cock still wet with her anal juices I was ready to cum again, so I made my finishing move shoving the rest of my cock, quite expectedly for Lilly, into her throat.
"Uhh ack...ack...bwoooah...ack eeeeehhh" Lilly gagged as I held my throbbing 8 inches balls deep in her little mouth and unloaded another helping of my cum directly down her throat.
I held for just a few seconds then pulled all the way out, allowing Lilly to breathe and compose herself.
Lilly sat back down on the floor for a few moments, then realising that we were done stood up, grabbing the fist full of hundred dollar bills I'd slapped down earlier along with the sexy underwear she came to show off.
Just as Lilly was pulling up her Victoria's Secret G-string again I walked up behind her and firmly pushed a finger back in her unsuspecting ass and she sucked in a quick breath of surprise.
"Come over again soon and we'll do this again ok?" I said, withdrawing my finger from her sphincters.
Lilly finished putter her underwear and clothes on then looked again at the cash in her hand.
"Uh ok...maybe next week."
