“Hello Heather! It’s me, Lily!”
“Oh hello” she answered, yawning in the background.
“I’m sorry, am I calling too early? I’m not sure about your sleeping schedule and didn’t-“
“No it’s okay. It’s almost noon on a Sunday, so just because I’m still sleeping in doesn’t mean you would be too. Besides, I should thank you again for keeping an eye on Timmy yesterday anyways. You must’ve really worn him out because he hardly had any of his dinner, just going straight to his room afterwards too.”
“Oh, well we didn’t do anything special. Just had lunch and watched a movie” I giggled, remembering how the afternoon had ended with my tongue buried in his mouth. The image alone was getting my mouth watering for a second chance!
“Speaking of Timmy. He left his jacket here yesterday and I was hoping to get him help about computers? He mentioned something about installing a software…” I lied.
“Oh yeah, no problem. He’s really good with that stuff. I’ll send him right over” she answered.
“You know Heather, I could keep him here a little bit longer if you wanted to get some extra shut eye. I’m sure Timmy won’t mind”
“Oh could you? That would be so amazing! I was really not looking forward to leaving the warm coziness of my bed. I owe you one!”
“Oh don’t say that! It’s my pleasure!” I answered.
“Ok I’ll send him over now. Chat with you later!”
Despite my excitement, I wanted to tease his patience first, see how he would react to me after what happened yesterday. Of course, the sports bra and tight yoga pants I had on was designed to make it that much more difficult for him.
“Well that was quick!” I giggled, welcoming him in after hearing his footsteps sprint towards my apartment.
“My mom told me…I…ughhh” he moaned, upon seeing my outfit. His eyes darted from my ample cleavage to my exposed stomach and then down my legs, until it landed on my bare feet.
I just stood there for a second, letting him gawk over my body until his gaze returned to my face.
“I thought I would take you up on that offer to help me workout. I hope you weren’t joking when you said it” I smiled.
“No! no! I’d love to help!” he stammered.
In his haste to get started, he actually tripped over his own shoes, trying to get them off as quick as possible.
“Careful! Are you okay?!” I giggled, squatting down to help him up.
Timmy turned to answer me when his thought was interrupted, staring at my tits that were now at eye level. Wanting to tease him more, I subtly squeezed my arms inwards, presenting even more cleavage for him to look at.
“Let me help you up!” I smiled, leaning towards him and grabbing his wrist. I almost felt a little bad at how merciless I was at teasing him, but it was so fun!
“Are you Okay? Did you lose your voice too from that fall?” I giggled.
“Oh no! I’m fine! I’m fine!”
“Good! I wouldn’t want your mom to think I was hurting you! Then you wouldn’t be able to come over anymore” I winked. “We wouldn’t want that, would we?”
He didn’t know how to respond, just nodding his head and nervously chuckling with me.
“Let’s move over to the mat” I smiled, not wanting to embarrass him too much.
I carefully guided him over to my living room, sitting him down on my couch as I stood in front of him.
“I’m just going to do a few simple warm up stretches first before we get started!” I smiled.
I had moved my coffee table aside, ensuring that we had plenty of room later for him to “help” me. I started off with a couple of innocent exercises to help loosen my muscles, getting them warmed up before I began hitting him with the more provocative poses.
“I can never quite reach all the way down!” I giggled, as I tried to touch my toes standing up.
With me bending forward so much, I could feel my tits trying to pop out of my sports bra, fighting to be let free. Timmy wasn’t trying to hide it at all, his mouth gaped wide open as he tried to stare down my bra.
“Ughh!” I groaned playfully, trying to reach further without bending my legs. “Help make sure I don’t cheat!” I giggled.
“No, just stay there! I’ll come to you!” I said, seeing him get up.
I moved right in front of Timmy, but instead of standing face-to-face, I turned around, with my back towards him as I bent down again. And almost as soon as I did so, I heard his breathing get heavier from the site of my ass. I made sure to go down extra slow, even wiggling my ass slightly as my hands made my way towards the ground.
“Keep my legs straight!” I instructed, grabbing his wrist and guiding them towards my hamstring. I purposefully rubbed his fingers across my legs, letting him know it was okay if they wandered.
And as I bent down further, I could feel my yoga pants stretching against my ass, testing the strength of the fabric. And with every movement, it felt my ass would burst free, tearing through the thin material that kept Timmy’s eyes away from his most wanted possession. After all, in my current position, I knew he could only see the top of my blue thong and not the rest of it.
Timmy was silent, probably too focused on the opportunity to fondle my body to speak much. I glanced backwards to confirm my beliefs, seeing him inch his face closer and closer to my ass. I waited patiently, letting him get too greedy before all of a sudden scooting back, smashing my ass into his face!
Unfortunately the contact only lasted a split second as Timmy backed away instinctively. But because my calves were pinned against his knee, I had no sense of balance either, falling back with him until I landed on his lap. Right away, I could feel his hard on poking against my ass.
Timmy tried to fix it immediately, moving his lower body away as he pushed me off of him.
“I remember this position!” I giggled, now sitting glued next to him with one leg propped up on his lap.
“Did you like what we did yesterday?” I teased.
“Mhm” he nodded, his heart racing.
I seductively moved my hand up his shoulder and towards his cheek, turning his face towards me.
“Would you like to do it again?” I asked, noticing for the first time that he was actually chewing a piece of gum.
“Is that why you have that?” I giggled, nodding towards his mouth.
“Yes! I mean no! No, I didn’t expect that you- but I really wanted to – it was just in case you wanted to-” he stammered, his face turning scarlet red.
“What flavor is it?” I smiled.
“Oh, it’s –“
Before he finished his sentence, I had already planted my lips on his. I was aggressive, picking up right where we left off yesterday. Apparently, Timmy had more than just one piece, as his mouth was filled with a tingling mint feeling of the gum.
“Peppermint, huh?” I teased.
I had hardly pulled away for a second when his lips instantly found mine again, kissing me with even more enthusiasm.
“Ugghh! Mhm!” he grunted, kissing me wildly. I could tell he had been waiting restlessly for us to make out again.
His kissing was just as “bad” as our first time and was based off of pure desire. I loved how, unlike his usual self, he didn’t care about embarrassment or have any tact, succumbing fully to my seduction. He was actually licking, not kissing, but licking around my mouth! As if I was the top of an ice cream cone!
“Lily…could…could I suck on your tongue like yesterday?” he asked, his eyes begging me.
I smiled back at him, tilting his head towards me as I presented my tongue for his waiting lips.
“Oops! Let’s just put that aside!” I giggled, feeling his gum drop on my chin.
He went back to sucking passionately, digging his lips as far in my mouth as possible. And whether on purpose or not, his own tongue was massaging against mine as well, providing even more pleasure for the both of us.
In the mist of making out, I moved his hand to my right leg, letting him feel me up as I attempted to find his cock. But surprisingly, Timmy was still feeling shy, rotating his hips away from my hand. I didn’t mind too much, knowing that sooner or later he wouldn’t be able to resist.
“Did you enjoy the underwear I gave you yesterday?”
“Yes! Thank you so much! I…I used them three times last night” he stuttered.
“Three times huh?!” I teased. “What about my socks? Did you leave them out of the fun?” I pouted.
“No! I kept them near my nose when I jack…jacked off”
“Did you now?! And you didn’t tell your mom right?” I teased, putting my index finger on his lower lip.
“No! I didn’t say anything” he answered, with a hint of fear in his eyes.
“Good!” I answered, sticking it in and out of his mouth slowly.
“And where are they now? My underwear and socks?”
“They’re in my pillow case and I already cleaned my room. My mom won’t find it! I swear!”
His nervousness made me giggle. It seemed he was still scared that I would stop it all, cut it off if he didn’t follow my directions.
“Are you going to use them again today? Use my thong to jack off?” I smiled, lightly kissing his lips.
“I…I would, but I made too big of a mess. Your underwear’s covered in my…my cum”
The very thought of it sent pulses towards my pussy, making it even wetter! I desperately wanted to see just what this boy had done to just a piece of my clothing. How would he react when he got to experience the real thing!?
“Well maybe later you can pick out another pair” I said, seeing the excitement on his face.
“But! But! You have to help me finish working out” I answered, wanting to tease him a little more.
“Yes! Sure! Anything!”
“Good boy!” I smiled, tapping his head as I gave him another deep kiss.
“Come. I want to work on my stomach a little” I said, moving back towards the mat.
“Oh my mom has one of those!” he exclaimed, upon seeing my ab roller.
“Then you know how it works then?”
“Yeah!”
“Great! Get behind me and make sure I don’t hurt myself” I said, kneeling down on my yoga mat.
“Come closer!” I giggled, reaching back and making sure he was basically pressed up against my ass.
“Hold my hips so I don’t wobble” I said, holding onto the ab roller tightly and gliding forward until my back was straight and parallel to the floor.
After holding the position for a second, I retracted my body back, rocking my ass into Timmy before moving forwards again. There wasn’t much contact in the first few trips, but with each successive one, I could feel his hands grip my hips tighter, pulling me closer towards him on my way back. It didn’t take long before I felt the head of his cock, poking into my ass.
From that moment, both of us looked to duplicate the sensation. Each time I returned back, I let my ass linger longer and longer on his cock, teasing him mercilessly. And as shy as Timmy was, he was still a curious boy, unable to control the new hormones coursing through his growing body. He was now rhythmically thrusting his pelvis forward to meet me, almost fucking me without even knowing it! I soon abandoned the ab roller altogether, focusing on increasing the pace and the intensity of our contact until I was openly dry humping him. Each time my ass landed on his cock, I wriggled it against him, letting him feel my asscrack for a few seconds before repeating it all over again.
I had hoped he would last a bit longer, especially after hearing of his activities the previous night, but that was not the case. Timmy’s grunts grew louder until they fell silent of a sudden, his hands dropping away from the side of my hips.
“Ugghh” he moaned, trying to recover his breath.
I could actually feel his cum soak through the cotton and spandex fabric of our pants, landing on my ass cheeks.
“Looks like you’ve made quite a little mess” I giggled, pointing at the stain on his crotch.
Even though he had worn black sweatpants, the darkened patch was still evident, with the stench of his sex in the air even more unmistakable.
“You even got some on me!” I exclaimed, wiping off some of the wetness from my ass.
“I didn’t mean to! I just couldn’t stop myself. It…it felt too good” he stammered.
“Then it’s only right for you to help me put on a new pair. After all, I have to go out fairly soon” I smiled.
I led Timmy into my bedroom, where I showed no shame, dropping my yoga pants to my ankles in one motion.
“Do you know what the weather is like outside?” I asked casually, completely ignoring the fact that he had an open view of my ass, with only a thong covering it.
“It’s uhm cold. Mom…mom said there might a late snow storm coming tonight” he answered, looking up and down my body.
I smiled to myself, turning around towards my closet and pretending to look for something in my lower drawer. From the workout, my thong had slid in my ass crack and was probably barely covering up my pussy and asshole now, exactly what I wanted!
“I’ll have to wear my ugg boots then” I said to myself.
“Well are you going to help me?” I smiled, turning around and holding up a pair of black pantyhose.
I didn’t wait for him to answer, allowing Timmy to collect his thoughts as I sat down on my bed.
“Start from the bottom, by my feet” I instructed.
Timmy dropped to his knees, his hands just as nervous as the first time he touched me, trembling with fear. His fingers shook as he slowly slid the opening over my toes and gradually moved upwards toward my calf. He was smart, taking his sweet time so that he could enjoy the feeling of my flesh against his fingers and palm.
“Make sure it’s all the way up” I smiled, spreading my legs a little for him.
My pussy was absolutely soaked, making my thong nearly see-through. Timmy’s eyes had taken notice too, transfixed on my pussy as he slid my pantyhose to the middle of my thigh, marking the halfway point of his task.
As Timmy started over on my right foot, he stumbled on purpose, acting as if he was having difficulty getting all my toes inside as he continued to stare at my pussy. I could only giggle to myself, loving every second of it. Even when my eyes met his, I only smiled, making Timmy go red instantly.
“Make sure they don’t bunch up on my feet. It’s really uncomfortable to walk like that” I smiled.
Timmy nodded his head, sliding the pantyhose all the way up my leg before going back down to focus on the ends. He started off doing as I asked, making sure they were spread out evenly, but that didn’t take long. However, instead of stopping, he kept at it, pretending like he was still trying to fix the placement of the pantyhose. He looked even more lustful playing with my feet than when I saw him staring at my pussy earlier.
“Timmy. Do you like my feet?” I asked, rubbing my left sole in his palm.
“They’re…they’re really pretty” he said, nodding his head.
“What do you like about them?” I teased more, moving my right foot up to his head now, gently touching his cheek.
“I like how soft they are. And how small your toes are. And how- “
“Do you like the smell? Do you like how my feet smell?” I said, pushing my right foot towards his nose.
“Augghh!” he moaned, gasping from the stench, nodding his head.
“You know Timmy, normally I always take a shower after a workout. But I don’t have time today. Do you think you could help me?” I asked innocently, tracing my big toe around his lips.
He looked at me with puppy dog eyes, almost in disbelief from what I had suggested.
“Open” I whispered, gently pushing my toes on his mouth.
When he finally did open, I gently slid my foot in, just the tip of my toes first.
“Ooooh! Good boy!” I giggled, reveling in the feeling.
I was just about to instruct him further when I felt Timmy’s tongue voluntarily start licking, covering the bottom of toes in his saliva. I watched as he lost himself more and more from the touch of my feet, sticking it deeper into his mouth. Soon he had all of my toes inside, sucking on them through the nylon of my pantyhose.
“Lily, I…I think I can do a better job if I take them off. I’ll put it right back on afterwards!” he exclaimed.
“Sure! That sounds good!” I smiled, reaching towards my thigh.
“I got it! You can just sit there! I should do this anyways for dirtying your pants earlier!” he stammered, pulling off both pairs quickly.
With both my feet free again, he reach for my ankles, holding both of them up towards his nose and inhaling deeply.
“Do they stink?!” I teased.
“Oh god! Yes!” he moaned, stuffing them at his nostrils, licking my soles at the same time.
I giggled loudly, both from his reaction and being ticklish.
Instead of killing the mood, my laughter only helped lighten it, causing Timmy to smile brighter as he licked up and down the bottom of my feet. The more I giggled, the more energize his tongue seemed to get, slobbering all over my soles before he began sucking on each one of my toes.
“Yes! Get in there! Make sure they’re all clean!” I instructed, spreading them out so that he could focus on each toe individually.
With Timmy so distracted on my right foot, I began creeping my left foot up his leg towards, the tent in his pants. And before I even met his hard on, I felt the wetness from his cum earlier, letting me know I was close. This time when my toes made contact, Timmy made no attempt to move away.
“That’s it! Don’t forget the top of my foot either!”
He was so focused on following my orders that Timmy didn’t even notice that I had guided him much closer to me than earlier, allowing for my left foot to reach his cock with ease. I began gently massaging it, feeling the shaft of his cock on my sole as I rubbed the head with my toes. Instead of fighting me off, he openly accepted it, the activity of his mouth decreasing as he came closer to climax.
It only took a few more wriggles before his cock erupted for a second time, dampening my toes with his cum. I waited patiently for his breathing to return to normal before putting my other foot up against his lips.
“You still haven’t cleaned this one yet” I said, tapping his mouth to open up.
And without him knowing, I slipped my cum-coated toes inside, letting him taste his own jizz! Timmy didn’t notice, probably believing the salty taste was nothing more than just the sweat that I had worked up from my workout.
“Don’t move! And stick your tongue out!” I smiled, temporarily pulling my foot aside.
“Good!” I giggled, wiping my sole up and down his tongue, cleaning his cum off.
“I think you did a good enough job” I smiled. “Now, gently put my pantyhose back on so I can go get dressed”
Timmy nodded, following my instructions perfectly.
“Uhm…Lily” he asked.
“Yes?” I answered, fixing the wrinkles in my dress.
“You…you said earlier that maybe I could pick out another pair of your…your underwear”
I smiled to myself, happy that he was showing at least some initiative.
“Hmm. I did say that, didn’t I” I answered, looking at my outfit in the mirror, not paying much attention to him.
“Well go pick a pair” I smiled, turning around and pointing towards my cabinet.
“I..uhm. I was hoping to have to one you have on now” he stammered.
“Did you now!” I gasped, slightly surprised at his forwardness.
“Come here” I signaled with my finger.
He approached cautiously, but any hesitation he had was quickly dispelled when I embraced him with a kiss again. When I felt his lips return the affection, I guided his hand towards my ass, pushing his fingers further and further down until he reached the hem of my dress.
Luckily Timmy had learned his lesson from yesterday, sliding his hands up my pantyhose and bare thighs until his fingers found the straps of my thong.
“Don’t wait too long” I giggled. “Otherwise it might dry” I whispered in his ear.
Hearing that sentence sprang his hand into action, roughly tugging my thong down my legs until he had it balled up in his hands. I grabbed it immediately, stuffing it against his mouth and nose.
“You like that don’t you, you little perv!” I giggled.
Timmy placed his own hands over mine, keeping my thong in his mouth. He was sucking loudly on it now, savoring the flavor of my pussy juices.
I laughed, leaving him on his own as I replaced my sports bra with a regular one and grabbed a pair of panties as well. I had taken my time to give him a chance to watch, but he was so caught up with my thong that he didn’t even notice. It was only after I had put on a sweater that he turned his attention back towards me.
“Alright Timmy. I’m afraid our time has come to an end for now” I smiled, planting a kiss on the top of his head.
“I have to go into work for a little bit”
“But it’s Sunday!” he retorted, noticeably sad to see me leave.
“I wish I didn’t have to go either” I said, telling the truth. “But unfortunately being an adult is not all it’s cracked up to be” I smiled.
“Can you come over for dinner again?! Please!” he asked.
“I dunno, that depends on your mother. I’m not sure –“
“I’ll ask her! I’m sure she’ll say yes!” he exclaimed.
“Ok. Well, if your mom’s okay with it, then maybe” I giggled, walking out of my room and towards the front door.
“Would you like to help me with one last thing?” I smiled, handing him my Ugg boots.
Timmy smiled widely, dropping to his knees to help put my boots on.
“I won’t say a word of this to my mom! Nothing!” he exclaimed, standing back up. “So…so can we do it again?”
“Sure can” I smiled.
“All…all of it?” he asked nervously, glancing towards my feet.
“All of it and more” I said, leaning down for a kiss on his cheek.
However Timmy surprised me, moving at the last second to meet my lips with his. I didn’t scold him, just kissing him back with the same intensity until I knew I had to leave.
“Ok. That’s enough for now” I giggled, wiping his drool from my chin. “I’ll be seeing you later then!”
I walked out with Timmy, dropping him by his apartment before leaving for my car.
Almost as soon as I entered the building of my lab, all happiness left my body; replaced by the gloomy feeling I had connected work with. The entire floor was expectedly empty, leaving me to do my tedious work on my own. I spent the first hour and a half setting up and running the experiment carefully, making sure each step was done without any error.
The last thing I wanted was my bitch of a boss to complain again and make me throw out this batch of data as well. “Oh, how I hated her so!”
I had often thought about getting her back, making life difficult for her as well, but nothing ever came of it. She was still the one in power, in control of everything, and I could only sit and take it. Not wanting to get even more flustered, I decided to take my half hour incubation time to do some online shopping.
I went with my go-to stress relieving solution, looking at pages and pages of designer shoes that I couldn’t afford. After my hopes had been adequately smashed by the insane prices, I moved on over to the website of the local shoe store at the mall. They were still overpriced, but at least began to fall somewhat into the range of what I was willing to spend. Most of them seemed fairly ordinary, but one pair of open-toed black high heels stood out, looking much sexier than its price would suggest.
The more I stared at them on my small phone screen, the more I wanted to go check them out. And soon my thoughts turned over to what Timmy had done earlier, giving me even more reason to go.
“I have to get a new pedicure anyways” I thought, remembering the chipped coloring of my toenails.
As I continued debating, my phone suddenly switched screens, going from my web browser over to the incoming call one.
“Hello Heather!” I exclaimed, happy to hear her voice. It wasn’t just the fact that she was Timmy’s mom that I was excited, but I really did like her personality. She was quickly growing on me.
“Hello! I think you know why I’m calling” she giggled. “I’ve been requested by my son to ask if you would like to join us for dinner”
I laughed with her, hearing how ridiculous it actually sounded. “Well you can inform your son that I would be happy to! I mean you’re okay with it, right?”
“Oh of course! I’d love to have you over!” she exclaimed. “I’m looking forward to that girl’s night out too!”
“That reminds me!” I exclaimed, switching over to my browser. “What do you think of these?”
“Ugh, sexy! I hope I’m not too old to say that!” she giggled, reviewing the shoes I was looking at.
“I’m thinking of checking them out after I’m done in the lab”
“Definitely do it! And if you get them, wear them over! I want to see them!”
“Sure thing! Oh, I gotta go. My incubation time’s almost over!”
“See you tonight then?”
“Yeah! Oh, what time?”
“Just as soon as you can! We can have a little wine too!” she exclaimed.
“Awesome! I’ll see you then!”
The conversation with Heather definitely cheered me up, allowing me to painlessly finish my experiment and make a hasty exit for my car.
As I went to check for the time, I was pleasantly surprised to see a text message from Timmy.
“I heard my mom say you’re coming tonight after going to the mall. Awesome!”
“Are you excited?!”
“Should I be? : )”
It was the first time he had so obviously flirted back with me, catching me a little off guard. I then realized that it was because we weren’t facing each other. It seemed Timmy gained a little more confidence behind the screen of his phone.
“That depends on you! ; )”
“Could I see the shoes you’re getting?”
“I’ll send a picture to you after I try them on. Ok, gotta go, talk to you later!”
The first thing I did was head for the nail salon, deciding on getting the pedicure first before moving onto the heels.
The shoe section was packed as expected on a weekend afternoon, ranging from old ladies to young teenage girls alike. I didn’t think much of it until I found the high heel I was interested in, with another customer looking over it as well. Surprisingly, it wasn’t a woman, but a teenager. He was stooped over, looking at his phone while matching it to the shoe in front of him.
I didn’t pay much attention to him, only looking at the shoe long enough to confirm that it indeed was the one I was looking for.
“Hello! Do you have this one in size 6.5?” I asked a clerk.
“Oh. I’m afraid this gentleman has just purchased the last one” he answered, pointing to the teenager beside me. “We’re having another shipment coming in the next few days though.”
“Oh. Thanks” I said, realizing that he indeed did have a box of new shoes next to him.
“Sorry about that” he said, overhearing my conversation.
“It’s no problem” I answered. “For you girlfriend?”
“Uh yeah. Valentine’s Day coming up” he answered.
“I see. How did you know what to pick?”
“She..uh…she told me”
“Okay” I said, giggling a little.
“Is that what teenage girls were doing nowadays? Making their boyfriends buy them things that they probably couldn’t really afford” I thought. “Poor sap, he definitely looks like the type that would be easily pushed around too”
“I don’t mean to be rude, but do you mind if I try them on? I just want to see how it will fit. I have clean feet, I swear!” I smiled.
His eyes understandably went to my legs and Ugg boots, but they did linger a bit.
“Sure” he said sheepishly.
“Awesome!” I said, taking a seat on the bench.
He handed the box over to me and stood to the side, trying not to stare but taking the occasional glance.
The heels were about 4 inch tall, with a sleek black design that looked very sexy. The front was also open toed, allowing for plenty of opportunities to tease Timmy later!
I quickly grabbed my phone, snapping a picture of them and sending them off to him.
“They look good!”
“Just good?” I joked.
“I mean sexy! They look really sexy!”
“Better, lol. Tell your mom, I’ll be there in about 45 minutes” I typed.
I was feeling down about having to wait and get them when I realized that while I was busy fiddling over my phone, the teen had taken the chance to check me out more.
“This could work to my advantage!” I thought.
“How does it look?” I asked innocently, getting up and propping my leg on the bench.
I head him distinctively gulp from nervousness.
“Good. They look good” he said.
It was quite hilarious to hear him describe it in the exact same way as Timmy did just seconds earlier.
“You think so? Oh Whoops!” I shrieked, pretending to fall as I grabbed his shoulders.
I leaned into him on purpose, pushing my chest into his.
“Why thank you!” I smiled, stabilizing myself as I continued to hold onto his arm.
“You’re…you’re welcome” he stammered.
The way he was looking at me told me everything I needed to know; those heels were coming home with me today!
“You must workout?! I can feel your muscles!” I giggled flirtatiously, grabbing his bicep.
He chuckled nervously, looking into my eyes.
“You know” I said, moving closer to him. “Valentine’s day isn’t for another week and a half. You could always come back and get the heels later”
“So what do you say? Do mind being a gentleman and letting me have this pair?” I said, rubbing his arm lightly.
“I…uh…I dunno. I think my girlfriend would be angry” he stuttered.
“What’s your girlfriends name?”
Before he could answer, I kissed him on the mouth. He was expectedly surprised, his lips frozen from my forwardness. I waited for him to recover, but when he continued to remain unresponsive, I had no choice but to start making out with him more.
There were a few other customers around, but nobody paid much attention to us. That was certainly one advantage of being short!
“So could I?” I said, staring teasingly into his eyes.
“Uuh…I…What…what’s your name?”
“Does it matter?” I answered, kissing him again on the mouth.
“So?”
“Sure…sure” he was able to stammer out.
“Great! Don’t worry, you can still get your girlfriends present later!”
“My girlfriend?! Oh my girlfriend!” he said, finally snapping out of his daze.
I on the other hand, didn’t wait that long, grabbing my stuff and the new heels and scurrying out of there before he fully came to his senses. What a rush! I felt so dirty yet so satisfying at the same time! The entire high lasted my entire drive home, giving my energy a much needed pick me up.
By the time I got home, the snow had really picked up, beginning to pile on the ground. The black asphalt of the parking lot floor was now covered in a fresh coat of snow, with no end in sight. I don’t know if it was the cold weather or because I had slowly lost track of time, but I found myself starving when I entered my apartment.
“I’ll be there in a sec, Heather! Just dropping off some stuff at my place!” I texted.
I dumped my bag on the sofa and quickly pulled out my new high heels, kicking off my Uggs at the same time. They were still a little uncomfortable, but would have to be broken into sooner or later, so why not now. Besides, I’m sure Timmy won’t mind seeing me any these!
“Is it that bad outside?!” Heather, exclaimed, softly patting my head as I greeted her.
I hadn’t noticed but my hair was spotted with snow from the storm outside.
“Yeah, it’s getting pretty bad. How much longer is it supposed to go?”
“Go grab Lily a towel, Timmy” she instructed, shooing him away.
“I think well into the late hours. Then it’ll depend on what the wind decides. Either we get another good amount tomorrow, or maybe we’ll be shown mercy and it ends tonight”
“Pot Roast?” I asked curiously.
“Yeah! Is that okay?”
“Of course! It smells great!” I exclaimed.
“Here you go Lily!” Timmy said, handing me a towel.
“Thanks!” I answered, drying my hair off immediately.
“Can I help in anyway?”
“Oh don’t worry about it! It’ll be done in a minute!” Heather answered, busy putting the finishing touches over the stove.
With her back to me, I walked towards the dining room table, handing the towel back to Timmy.
“Thanks” I winked, teasing his fingertips with mine.
Timmy responded with a big smile, taking a small step towards me. I turned around quickly, making sure Heather was still occupied before leaning down to kiss him.
He was definitely ready for it, placing his hands instantly around my neck as he kissed me back. I did my best to hide my giggling, trying to keep it quiet from his mom. Unfortunately, Timmy either forgot or couldn’t control himself as he began moaning as soon as our lips touched.
Luckily, Heather had the kitchen fan on, masking both Timmy’s grunts as well as the smacking noises of our lips.
“I better teach this kid how to kiss properly one day!” I thought, realizing just how loud it was now that we weren’t alone.
Knowing Heather was almost done, I didn’t want to get too comfortable and risk the chance of being caught. Besides, there was a whole evening for me to slowly tease him!
“Let me help set the table then” I answered, pushing Timmy gently away.
“Could you show me where everything is?” I asked him.
“Yeah” he answered, noticeably sad from me breaking it off.
The timing worked out well as once we had all the plates and utensils set, Heather had finished as well. We took our seats, with Timmy sitting next to his mother while I sat across him.
“Wow, this looks amazing!” I exclaimed. “You didn’t have to go through all this trouble just for me! Anything would’ve been fine!
“It wasn’t too difficult, honest! The slow cooker did most of the work!” She smiled.
“Ugh! It’s so soft!” I exclaimed, taking a bite of the beef.
“I’m glad you like it” she giggled. “Are you going to eat too or just stare at our guest” she joked, looking at her son.
Timmy instantly pulled his gaze away from me, looking back down on his plate in slight embarrassment. I was afraid to laugh, but after seeing the same reaction on his mother’s face, it made both of us giggle loudly.
“Oh! I was distracted by dinner that I didn’t even ask. Did you get the heels?!” she exclaimed.
“Yes!” I answered excitedly. “Check it out!” I said, getting up.
“Oh, I should’ve taken them off, right?! I was a little excited from them and forgot-‘
“They look amazing on you!”
“So sexy!” she laughed.
“You think so?!”
“Uh yeah! When are you going to debut them?!”
“How about we go dancing next weekend?!” I asked excitedly.
We were so caught up in girl talk that we had almost forgotten entirely about Timmy. He was sitting quietly on his seat, peering over the table to my side to see the heels.
“What do you think, Timmy? Does Lily’s new shoes look nice?” Heather asked, noticing too that we had left him out.
“They’re…they’re good” he said softly, trying to hide his excitement.
“Well thank you!” I smiled, posing them a little bit longer for him to see.
Even though, I was delighted to see that Heather also found it fun to tease him about his crush on me, I still needed to be careful. After all, there was a big difference between flirting with her son, and doing what we were already doing, much less all the other things we would be doing soon.
“Were you serious about dancing?” Heather asked nervously. “I haven’t done that in a while and I doubt I could keep up with you!”
“You have to come, it’ll be fun! We don’t have to do anything too crazy and besides, I’m not that much older than you”
“I’m 36” she said cautiously. “You…you couldn’t possibly be in your 30s, could you?”
I giggled, finding it both flattering and funny that she had thought I was much younger.
“I’m 32” I smiled. “not that much younger than you”
Before his mother could respond, Timmy began choking on his food, coughing loudly.
“Well I guess my son beat me to it” Heather laughed, handing him a napkin. “You’re really 32 already? I always thought you had just finished your PhD and was around 26, 27. And even then, you don’t look that old”
I didn’t know how to respond and seeing Timmy’s continued look of shock was surprising to me. I thought about it, and realized that through all our conversation, he had never really asked about my age.
“So Timmy, how old did you think I was?” I teased, seeing his mother waiting just as anxiously for his answer.
“I uh…I –“
“Well spit it out, son!” she giggled.
“uhm 24?” he stuttered.
“What a sweet mouth you have!” I said, smiling at him.
“Thank you so much for the compliment!” I said, touching his leg with my foot.
Timmy jumped in his seat instinctively, almost knocking over his plate.
“Are you okay?!” Heather laughed. “It’s not that big of a deal!”
“Oh I’m sure he was just caught off guard” I answered. “He’ll get used to it” I said, rubbing my toes on his calf.
For the rest of dinner, I continued to tease him under the table, but Heather was so talkative that it became quite hard to do both. And soon enough, the two of us became involved in our girl talk again and Timmy was left out.
With nothing to keep him entertained, Timmy had finished his food quickly, excusing himself from the table to avoid our “boring” conversation.
“Let me get two glasses of wine!” Heather exclaimed, moving behind me, into the kitchen.
I had expected Timmy to leave for his own room, but he seemed content to stay in the living room, watching TV. Only, the more I looked at him, the more I realized that he was taking the opportunity to take peaks at me while I ate. He had picked a good spot, sitting behind his mother while facing me, giving him all the freedom in the world to look.
“Here!” Heather said, handing me a half-glassful of red wine.
“Thanks!”
“Oh I should be thanking you! Now I can have a glass of wine without feeling too guilty!” she laughed.
I did my best to make conversation with Heather, but I was much more interested with teasing her son now. I didn’t show it, never directly looking over at him, just repositioning the way I sat. I was now sitting almost sideways on my chair, with my legs on the outside for him to stare at.
And as Heather continued to carry the conversation, I crossed my legs, leaving my right foot on the ground while letting my left one dangle in my new sexy black high heels. It only took a few seconds before Timmy noticed. He had abandoned his attention on the TV entirely, focusing completely on my feet.
It felt so hot teasing him literally right in front of his mother! And I couldn’t stop myself, only wanting to go further. Gradually, I let my heel slip out of the shoe, just gently dangling the front on my toes. Timmy’s face looked like he was about to cum any second!
And I as slowly rotated my foot seductively, I swear Timmy was also rotating his head accordingly, hypnotized by my actions. Finally, I slipped the heel completely off my left foot, leaving it in just my pantyhose.
“That sounds so interesting! Tell me more!” I smiled to Heather, only half paying attention as I pretended to scratch my legs.
Only instead of satisfying any physical itch, I was satisfying my sexual one. I gently glided my fingers higher and higher up my thigh, pushing my dress up with it. I even uncrossed my legs, splitting them apart so that I could flash him my panties as well.
Timmy’s hand was now on the front of his pants, undoubtedly rubbing his cock. And it was only when he was in this position that I glanced over at his direction, smiling widely. However instead of looking away, he only stared at me more intensely, openly groping himself.
“Oh please excuse me for a minute, looks like all that wine went right to my bladder!” Heather joked, getting up with a slight wobble.
I faked a laugh, watching her exit the room and disappear into the bathroom before turning my head back towards Timmy. But instead of seeing him on the couch, I was startled by the sudden contact of his hands on my leg.
Timmy was down on his knees, grabbing my left foot and stuffing my toes into his mouth! He looked completely lost, like a kid gorging on candy after a night of Trick-or-Treating!
“Don’t choke!” I giggled, covering my mouth. “Oooh It tickles!”
“Auugghhh! You taste so good Lily”! he moaned, licking up and down my sole.
I was trying to pay attention to the bathroom, listening for the inevitable flush so that we wouldn’t get caught. Timmy had no care at all though, keeping my foot in his mouth as he desperately tried to undo the straps of my right foot.
Before he had them all the way off though, I pointed my toes at him.
“Lick!” I instructed.
He looked hesitantly at me, not sure of what I meant. But as I pushed my toes into his mouth, he slowly gave way, letting me tease the tip of his tongue. Then gradually, I moved my foot, forcing him to lick the side of my new shoe as well.
“Now suck!” I said passionately, presenting the heel for him.
He no longer complained, accepting my directions as he wrapped his lips around the 4 inch spike.
“Yes!” I moaned, pushing it in and out of his mouth, loving the way I could tease him.
“Now you can take them off!”
However, the euphoric moment was suddenly cut short by the flushing of the toilet.
“Your mom’s coming now!” I shrieked.
But Timmy didn’t stop, only sucking louder now that my right foot was open for him to play with as well. I had wanted to stop, but seeing his passion was so hot!
So instead of pushing him off, I leaned down and grabbed his collar, pulling him towards me so I could dig my tongue down his mouth.
“Mhm! You naughty boy!” I shrieked, pushing my foot on his cock. He was rock hard, making me kiss him even harder.
Just as I heard the bathroom door swing open, I grabbed my almost empty wine glass, dumping the remainder on the tiled floor below me.
“Oh I’m sorry Heather! I accidentally knocked over some of the wine. Timmy’s just helping me clean it” I said, doing my best to sound normal.
She was so giddy from our conversation and the alcohol that she hardly paid any attention to my statement.
“Oh wow!” she exclaimed.
Timmy and I looked nervously at each other, but before we panicked, Heather began walking over to the window.
She pulled open the blinds more, revealing why she had been so excited. The snow was coming down even harder now, and as I walked closer towards the window, the more terrifying it looked outside. We were too high up to tell exactly how much had accumulated, but the top of all the cars in the parking lot were completely covered.
“Yes, no school!” Timmy exclaimed loudly, reminding me just how juvenile he still was.
The thought also made me instantly remember my own work. And as much as this would’ve been a fair excuse with any other boss, it was likely not going to be the case with mine. Unless there was literally a citywide shutdown of the roads, this was hardly going to be a valid excuse in her eyes.
My self-pity mood was interrupted by the ringing of a phone.
“Yes. Yeah, I’m listening” Heather said.
“It’s the hospital. Do you mind if I ta-“
“Go ahead” I whispered. “I have to clean the mess I made anyways”
“Thanks!” she mouthed, heading towards her room.
I took the chance to quickly wipe up the spill, making sure there was nothing left before I sat back down on my chair. With all that had happened, I had only eaten half my plate, leaving me still quite hungry.
“Is your mom going to be in there a while?” I said, looking over at Timmy.
“Should be. I think she’s discussing schedule changes. Whenever there’s a storm she usually has to go in for extra hours” he replied.
I nodded my head, agreeing with what he said.
“Well?” I smiled. “I don’t think you were quite done yet” I said, dangling my foot again.
I didn’t have to tell him twice as Timmy gleefully rushed towards me, squatting himself under the table to take hold of both my feet.
“Don’t tear my pantyhose. And if you do a good job we can make out after I finish eating” I said nonchalantly.
His tongue felt so nice on my feet, relaxing my muscles after an afternoon of walking around.
“Good job, but don’t forget my soles either” I said, reaching under and patting him on the head.
“I won’t” he panted, doing as I asked.
For the most part I continued to let Timmy do as he pleased while I fretted about the busy week ahead. I dreaded it so much that I almost forgot there was a person attached to the special foot massage I was receiving. It was only when my right sole was suddenly touching something hard that I noticed. The little perv was learning quick!
I pretended not to be bothered, pouring myself another glass of wine while I actually began paying more attention to his actions. Timmy had, over time, subtly pushed my thighs aside, giving him a close up look of my panties. I surprised him by spreading my legs all the way open, letting Timmy know I was onto him.
“Ohhh!” he groaned, choking on my toes.
I giggled loudly from his reaction. “Ok get up! I’m just about done with dinner!”
Hearing Heather still talking loudly on her cell from the other room, I knew I’d have a little more time to play than originally anticipated.
“Did..did I do a good job?” he asked nervously.
“You did” I smiled.
He rushed towards me instantly, embracing me with a hug and trying to pull me down for a kiss.
“Wait! Wait!” I giggled. “You said that you’ve already used the underwear I’ve given you, right?”
“Yes!” he nodded.
“Prove it!” I smiled seductively.
He grabbed my hand, leading me quickly into his room on the opposite end of his mom’s. And while he was busy scrambling around on his bed, I took the time to lock his door, just in case Heather finished with her call soon.
Timmy proudly held up two pairs of my underwear, including the blue thong I had given to him just hours earlier.
“My my! You work quite fast, don’t you” I smiled, grabbing the blue one back.
I felt the moisture of his cum instantly. He must’ve used them right before I got here!
Staring right at him, I held my own thong up to my face, bringing it to my nose before taking a long, wet lick of his cum.
Timmy was speechlessly staring at me, his cock threatening to tear a hole in the front of his pants.
“How do you use my thongs, Timmy?” I teased.
“I..uhm…I-“
“Show me!” I said sternly, staring at him with all seriousness.
“Show…show…show you?”
“Is that a problem?” I asked, walking closer to him. “I’ll let you make out with me more if you do” I whispered in his ear.
“ugh!!” he moaned.
“Don’t you want to suck on my tongue again?” I teased, kissing his neck tenderly.
“Mhm” he mumbled.
“Then what’s the problem? Don’t you find me hot?!”
“Yes! You’re so hot Lily!”
“Then show me! Show me what I do to you!” I said, rubbing the outside of his cock.
“Ok! Ok!” he said more confidently, taking a seat on his bed.
I wanted to both laugh and celebrate at how smoothly I was able to seduce him. Just a few weeks ago he was so shy that he could barely form complete sentences with me. And now? Now, he was about to have his cock out, jacking off in front of me!
Timmy pulled his pants and underwear down just enough to expose his cock. The first thing I noticed was his pubic hair, or lack thereof I should say. There were just the faintest signs of fuzz starting to show, but I guess he was still a little too young for there to be anything more than that.
He wasn’t incredibly big at 4 inches, just about the size I expected at his age, and smaller than my nephew for sure. But in the moment, I had the same intense feeling with Timmy as the first time I fooled around with Chris. Looking into his innocent eyes was such a turn on! This kid should be in here enjoying his video games instead of sitting next to me with his pants pulled halfway down.
“Let’s get started then!” I said, handing him over the blue thong.
Timmy nodded his head, wrapping his cock around with the blue fabric and began pumping. I could tell that he was still nervous with me, so I did my best to relieve that by kissing him.
I started off gentle, keeping it mostly between our lips until I felt his breathing slow down more. With that positive sign, I began adding more tongue, French kissing him as he loosened up. Timmy began pumping faster, moaning into my mouth as he did so.
But as I watched him jerk off, I noticed him speeding up for only a few seconds before stopping altogether, waiting for a few seconds and picking up again. How cute, he was trying make it last!
“Go ahead Timmy. Cum! Cum for me!” I said, nodding at him. “I want to see it! Do you need help?”
I didn’t wait for him to answer, wrapping my hand around his and pumping with him.
“AUughh!!” he moaned, cumming instantly. His whole body twitched for a split second as his cock pulsated with load after load. It easily seeped through my thong, filling both of our palms with his sticky cum.
“That’s quite a load kid!” I smiled, staring at his handiwork.
Not wanting Timmy to feel any post-orgasm shame, I continued to make out with him, determined to keep him at a sexual high. His kissing gradually returned to his usual vigor, sucking on my tongue roughly. While he enjoyed himself, I began cleaning up with my thong, wiping the remaining cum on his cock off. And as I cleaned him, I felt it come back to life. How good it is to be young!
“Looks like you’re ready again!” I smiled.
“But I don’t have anymore of your thongs. I’ve already overused the other one” he said, almost distressed.
“Well then we’ll just have to use this one then!” I said, moving his hand up my leg.
Timmy immediately understood, reaching up my legs with confidence to tug off my panties.
“Sorry they’re not as sexy as the other ones!” I giggled. “But I’m starting to run out of those because of someone!”
Timmy chuckled at my joke, bringing my panties up to his nose to sniff. My pussy was drenched so there was no doubt he was getting a good whiff of my scent!
“Someday I’ll show you the source!” I said, guiding his hand back down to his cock.
This time I took charge, slapping his hand aside and using my own to wrap the panties around his cock. I started slowly stroking, knowing that he probably still wasn’t going to last long.
“Kiss me” I said, trying to distract him.
Timmy leaned closer into me, his left hand feeling up my leg as we made out. I found it cute that even now, he didn’t dare reach for more than I allowed. Well that was about to change!
Using my free right hand, I grabbed his wrist and moved it from my leg all the way up my stomach, going slower and slower as it approached my tits. I could feel his anticipation through our kissing, his breathing becoming sporadic as his fingers inched closer. Finally, I decided stop teasing him, letting him get a handful of my 32Cs. It was over the top of both my sweater and bra, but regardless, it was probably the first tits he’s felt.
“You like that?!” I asked rhetorically.
He could only moan for an answer, kissing me more deeply. His hand was gentle around my tits, as if he was afraid to hurt me. In fact, I actually had to squeeze his fingers to let him know it was okay!
But once I did, all formalities were gone as Timmy quickly began groping me crudely. And with his attention so preoccupied, he had lasted much longer than I hoped. My hand had subtly pushed the panties aside as I stroked his bare cock, giving him his first real handjob.
“AUuggh! That…that feels so good!” he moaned.
“You like my hand around your cock?” I teased. “Is it better than the thongs you’ve been using?!”
“Yes! So much better!” he moaned.
“Good! Relax then! Close your eyes and enjoy it!” I said, snaking my tongue in his mouth for him to suck on.
I was enjoying myself just as much as Timmy, exploring every inch of his young cock and balls. His shaft was smooth, not even old enough to develop any bulging veins yet! The more I saw my hand pumping his cock, the more desperate I became to suck on it. I had originally wanted to take it step by step, but the temptation was becoming too much.
With Timmy’s eyes still shut as he kissed me, I acted quick; pushing him away in one motion as I dropped to my knees, taking his cock in my mouth.
“Auugghh!” I moaned in relief. It was unbelievably satisfying!
Before Timmy could scream, I shoved my panties into his mouth, keeping him quiet for the time being.
“Your mom will hear!” I smiled, whispering softly as I licked the head of his cock.
His cum tasted so good! I began bobbing up and down his length with little difficulty. I didn’t care anymore about making him last as there was no way he would.
And almost on cue, I felt Timmy’s legs kick out straight, flooding my mouth with his cum. However, he did surprise me by having another 3 thick loads so quickly.
“Lily?!” Heather shouted.
I could hear her voice from the other side of the apartment, entering into the kitchen and living room area now.
“I’m playing a game with Timmy on his Wii. We’ll be out after this round!” I said, winking at him.
“Ok!” she answered. I could hear the sound of the faucet running, letting me know we were safe.
Timmy had been motionless, drained of all energy and emotion until I made that statement. Now he was smiling back at me brightly, with my panties still stuffed in his mouth.
I gave his cock another few slurps, enjoying the taste of his cum before standing back up and removing his gag.
“Shh! Not a word to your mom!” I smiled.
He nodded his vehemently in agreement.
“This, you can keep” I said, giving him my panties back.
“Did you like what we did?”
“Yes! It felt so good! That was a blowjob right?!”
His excitement made me laugh. “Yes, it was. Where did you learn that, your computer?” I asked rhetorically, knowing he would be too embarrassed to answer.
“Would you like to do –“
“Yes!”
“Well one condition” I said.
“Anything! I’ll do anything!” he exclaimed loudly, almost shouting.
“Shh!” I giggled, slapping him lightly on the arm.
“Sorry!” he whispered.
“You can’t cum before then” I said.
“What?! Why?!”
“Because I like the way you taste!” I answered, sucking my index finger seductively. “And I want you all filled up for next time!”
“Can I come over tomorrow then?! I won’t last longer than that!” he answered truthfully.
“Yes! After I come back from work” I smiled. “Do we have a deal?!”
“Yeah!” he answered excitedly, holding up his pinky.
I giggled at his youthfulness, happy to oblige to a pinky swear.
“Ok! Clean all this up before your mom comes in!” I said, fixing my sweater and dress. “I’m gonna go chat with her outside in the meantime!”
“Is everything okay Heather?” I asked, helping her move the dishes into the kitchen sink.
“Oh yeah! I just might have to stay a bit longer tomorrow at the hospital, depending on when the storm ends today” she answered.
“Did you enjoy the food? I’m sorry I had to cut dinner short a little!” she said, with a genuine sadness in her voice.
“The food was amazing! I really enjoyed it! And don’t worry about the interruption, I had a good time with Timmy anyways!” I said.
“Great! I’ve felt so much better with you around to keep an eye on him! It’s such a relief!”
Her words made me feel slightly guilty for what I was doing, but as soon as I recalled just how happy Timmy’s face was, it quickly disappeared. Sure, I was getting a kick out of seducing him, but he wasn’t exactly protesting either!
“In fact, I’d like you to have this” Heather said, interrupting my thoughts.
She handed me a key, no doubt a spare for her apartment.
“It used to be Timmy’s dad’s, but…-“
“I’m flattered!” I answered, seeing her struggle to talk about her ex-husband. I didn’t know much, only that she had divorced years back, and probably not in a good way. Regardless, I wasn’t going to press her if she didn’t want to talk about it.
“Let me help you clean up! We can finish chatting too!”
“Great!” she beamed.
Talking with Heather was such a wonderful way to keep my mind off the fact that the weekend had come to an end. I went to sleep both dreading the work to come as well the chance of fooling around even more with Timmy. Oh well, I guess you win some and lose some.
Author’s Note: Thanks for bearing with me despite the delays. This week was just a little busier than usual. I don’t anticipate it being the case for chapter 4. Also there was a lot of request for more foot fetish scenes, even more than usual, haha. Hopefully, I covered that aspect well in this chapter. Chapter 4 will be a little more fast-moving, but I still need to iron out all the details. Again, I always appreciate the comments and suggestions, especially from my long time readers who’ve read my other series as well. I know it must’ve taken a lot of time!