Teen Cocktease Babysitter

What a day! Project meetings all day long, from 9am to 9pm, with really intense demo testing, barely half an hour for lunch, and I was on point for the whole day as the lead system analyst. I was sooo tired when I got home.

Opening the door, I hoped my kids were asleep and there would be no crises to deal with.

I couldn't hear a sound. Yay!

April had come through for me again. I'd hired her recently as a babysitter, knowing I had an intense work schedule coming up. She didn't just babysit, she picked up both kids, from daycare and school, played with them, gave them dinner, and put them to bed. She got them to bed early too, I was impressed. Why couldn't I do that?

We did a couple of dry runs first, with me there, so I could see how she handled both kids, because April was only 18, so I had reservations about her maturity, despite the great recommendation a friend from work gave her.

I needn't have worried. She was perfect, ultra-competent. I even felt bad paying her $15 per hour, it didn't seem like enough, but she assured me it was cool, and that after the kids were in bed, I was basically paying her to study. Plus I was paying for a lot of hours.

The only problem, if you can call it that, was how sexy she was. Sometimes, I had totally inappropriate thoughts about her. I didn't let myself dwell on them, or indulge myself in fantasies, but I had to admit: I fancied her like mad.

Entering the living room, I expected to find April studying as usual. She had just started a psychology major. Instead, she was curled up on the sofa, fast asleep. The coffee table was littered with textbooks, and a notepad. I saw the baby monitor was there too, switched on, and facing her.

Ravenous after my long day, I left her sleeping and went to the kitchen, rustling up a thick Scooby-snack chicken salad sandwich. I ate in the kitchen so as not to disturb April, then got a beer from the fridge and went back to the lounge.

I was going to wake her up, and tell her she could go home now, but instead found myself watching her sleep. It was a rare opportunity to simply look at her, and I took full advantage.

I studied her face, the few freckles on her cute nose, the beauty spot just above her lip, her long strawberry blonde hair. My eyes travelled down her petite body, taking in what she was wearing today: a clingy, figure-hugging stripey pink and black top, with a tight, short green skirt, and opaque white tights.

I felt a bit guilty, just standing there, checking her out, but not too guilty to stop doing it, apparently. I sipped my beer, relishing the view. It hit me once again how hot she was. I imagined what she looked like naked, wondering if she had a boyfriend - or a girlfriend - and what she was like in bed. I pictured her naked, wearing just the tights, and my cock hardened.

Eventually, I realised she should really be getting home. It was almost 10pm. But I didn't want to wake her up either. So I decided to sit on the sofa next to her, and do some work, preview tomorrow's schedule and meetings. I figured my sitting down and typing would wake her up gently.

I got my chromebook, flipped it open, and sat down, slightly awkwardly, unintentionally sitting on her toes. April murmured in her sleep, and drew her knees up towards her chest. I glanced down at her briefly, and did a double take as I saw her skirt had ridden up her thighs - she wasn't wearing tights, she was wearing thigh high stockings! I could clearly see the lace band at the top, and a glimpse of bare thigh above.

Wow! I would never have guessed April wore thigh highs. I tried to concentrate on my work email, but it was impossible now. I love stockings. My cock was hard again, and I gave into it, sat back, and looked at her legs, and her feet.

The thought popped into my head to touch and fondle her feet. I knew I shouldn't, but the thought grew in my mind, and I figured if she woke up, I could make it seem like incidental contact.

I reached out and touched the top of her foot, stroking it softly, tenderly. At first, there was no reaction, then April sighed, and turned onto her back. I froze, and waited, eventually remembering to breathe.

She was still asleep.

Her legs were pressed together, knees bent, her left leg resting against the back of the sofa. Her skirt was well above the stocking tops now, but I couldn't see anything.

Then, sooo slowly it was almost in slow motion, her right leg fell away from the left, all the way down to lie flat on the sofa seat. Her skirt rode up almost to her waist, and her legs were spread wide open right in front of me, revealing her pink panties.

I couldn't believe it!

I stared at her panties. They were a thin fabric, cotton mix or maybe microfibre, and clearly outlined her pussy lips.

My cock was straining uncomfortably against my underwear, so I unbuttoned the trouser fly and adjusted it. Enjoying the touch, I let my fingers linger there, slowly rubbing the tip, then the shaft, through my underwear. I leaned over to get a closer look at her gorgeous young pussy.

By now, I was really horny, and started to think with my dick. This was a once-in-a-lifetime opportunity, and I wanted to masturbate and cum right then and there, despite the risk. Maybe the risk excited me even more. I was already leaking precum.

But how should I do it? I didn't have any tissues handy, and didn't want to maybe wake her up going to get some. I could cum in my underwear, but didn't want to make a mess of my beige work trousers, and there would surely be a big mess.

So I came up with a plan: touch myself through my underwear until I was right on the edge, then get my cock out, cum in my other hand, then make a swift but controlled exit to the bathroom.

I stroked myself gently, and noiselessly, for a few minutes, feeling the urge to cum build up inside, and starting to tingle all over. I slowed down, prolonging the edge, riding it, and imagined sniffing her pussy.

That got me even closer - it was time to cum! I looked down, gingerly taking out my cock, trying not to get any of the copious precum on my trousers. I cupped my other hand over the tip and got ready to explode.

As I turned back to look at April's panties, I heard the sound of a camera phone photo being taken! I looked up and saw April looking at her phone, at the photo she'd just taken. She looked away from her phone, directly at me, her face deadly serious, and said "You dirty little pervert."

I froze, cock in hand, my heartbeat skyrocketing. So much for my genius plan.

I had no idea what to say, so I didn't say anything. April continued: "I should post this right now on your facebook page, so all your friends and family and work colleagues can see what a depraved, filthy pervert you are."

She could do it, too, it was no idle threat. She'd friended me recently, so we could chat on messenger about our schedules to make the babysitting arrangements. My heart pounded.

April looked exasperated. "Well, don't you have anything to say, pervert? Are you unable to form words when your dick is hard?"

Finally, I tucked my cock away, and blurted out "I am so, soooo sorry, April. Please don't post that photo. I don't know what I was thinking. I just couldn't stop myself somehow, you looked so sexy ... "

April interrupted me: "Oh, so it's MY fault now, is it?" She was pissed. Rightfully so, I had to admit.

I tried to backtrack: "No, no, it's my fault, completely my fault, I was ... I was weak." I felt like bursting into tears, but just about held it together.

April sighed deeply, shaking her head. I noticed then that she hadn't actually changed position - her legs were still spread open, almost like she was daring me to look between her legs again. Maybe she was. But I didn't dare look. I looked everywhere but there.

She sighed again, and sat up, closing her legs, smoothing her skirt back down over the stocking tops. I was relieved she had removed the temptation for me to look.

I felt the need to say something. "I know this is bad. Can you forgive me? Is there anything I can do to make amends? Anything at all."

April looked at me thoughtfully, like she was figuring out a crossword clue. She seemed less angry now, but hard to read.

After about a minute, she seemed to arrive at a decision, and smiled to herself. She looked at me. "Ok, why not? I guess I don't have to post that photo. Maybe we can salvage something from this. You want to make amends?"

I met her eyes and nodded earnestly. "Yes, I sincerely do."

April held my gaze, and replied: "Alright then. There are two things you can do. First, if I'm going to continue working for you after this, I want a pay rise. You'll pay me double from now on. Retroactive to the start of this month, and paying me for next week in advance. Acceptable?"

I hesitated. $30 per hour was steep. This would cost me a lot. But I had wanted to pay her more, and even with all the hours she was putting in, I knew I could afford it. I also didn't want to keep her waiting. "Yes."

"Good. Pay me right now. Make a bank transfer as usual. Do the math, and send it, then show me the transaction confirmation."

I went to work. It didn't take long. 20 hours per week, 3 weeks retro at $15 per hour plus next week's 20 hours at $30 per hour. $1,500 total. I clicked send, and showed her the screen.

She seemed satisfied. "Fine. Now for the second thing."

I waited patiently, while April looked at me, smiling. "The second thing you can do is ... play a game with me."

"A game?" I repeated, wanting to make sure I heard correctly.

"Yes, a game."

I had no idea what the second thing was going to be, but it sure wasn't that. "What kind of game?"

April smiled again. "I'm not going to tell you unless you agree to play."

"Oh", I faltered. I didn't like the sound of this. I could be agreeing to anything. "Umm, can you, errr, give me some kind of idea what the game involves?"

She shook her head. "No. But I can tell you this much: if you agree to play, I'll delete the photo, here and now. We'll start playing the game immediately, and you can stop any time you want."

That sounded reassuring. "Really? I can stop the game any time? Even, like, right away?"

"Yes. Absolutely."

I thought about it. But not for long. The way I saw it, I had nothing to lose. "Ok, I'm in."

April reached for her phone, touched the screen a few times, then turned it towards me. I cringed at the image of me, holding my cock, leaning toward the screen, staring between her spread legs at her panties. She deleted it. Just like that.

I actually sighed with relief.

April put her phone down, and sat back. She seemed more relaxed now too. "You looked like you were really enjoying yourself there. Pretty close to cumming, I reckon. Am I right?"

I felt awkward but answered anyway: "Umm, yes, yes I was close. Very close."

April reclined a little, and whispered: "Would you like to look up my skirt again?"

I looked at her incredulously. Then it dawned on me. "Are we playing the game now?"

"Yes", she nodded, and added: "If you want to see my panties, take off your clothes and get on the floor."

I wanted to see her panties, that's for sure, but couldn't quite get over my surprise at this turn of events, and the result was a kind of paralysis. I was also nervous at getting naked in front of her.

April laughed at me. "Are you shy all of a sudden? I've already seen your cock, you know. Or is that not it? Do you have, like, a tattoo of Dolly Parton on your chest or something?"

I had to laugh then, and felt silly for holding back. I stood up and unbuttoned my shirt. Curious, I asked: "Does this game have a name?"

April was watching me patiently. "No."

I took my shirt off and draped it over the back of an armchair. "Does it have rules?"

She smiled. "Most definitely."

I took off my socks. "You're not going to explain them to me though, are you?"

Sure enough: "No."

I unbuttoned the fly and took off my trousers, standing in just my underwear, light blue cotton briefs. There was an obvious, and large, wet patch at the crotch, where I'd leaked precum earlier.

April noticed that, of course. "Nice stain you've got there, Mister."

Blushing, I stepped out of the briefs, and sat down cross-legged on the floor in front of her.

April moved forward on the sofa, and stretched out a stockinged foot. She lightly brushed her toes against my chest hair, which made me shiver, then slowly opened her legs, allowing her skirt to ride up, showing me her stocking tops, and finally her panties.

I was pretty sure I had permission to look now, and stared between her legs, feeling my dick stiffening. I looked up at her a little anxiously, just to make sure she was cool with it, because I basically had no idea what was going on.

As if reading my mind, April said "It's ok, you can look all you want. But if you want to keep looking, stroke your cock."

That was fine by me! I started to touch myself with long, slow strokes, enjoying the sensation, and drinking in the sight of her spread legs, thigh highs, and panties.

Keeping her legs spread wide apart for me, April reached over into her rucksack, pulled out a bag, and emptied it onto the sofa next to her. It looked like clothes, mostly, and some lingerie, and a couple of drawstring bags.

She picked up a pair of sexy black bikini panties, and tossed them down on to my lap. I picked them up with my free hand, and looked up as April traced a finger slowly up and down her panties, rubbing against her pussy. A small dark wet spot appeared on her pink panties.

April took her finger away, and brought it up to her nose. She closed her mouth and breathed in through her nose, then paused and looked at me: "If you put those panties on, I'll let you sniff my wet panties. Would you like that?"

My cock twitched at the thought of smelling her. I REALLY wanted to. All I had to do was put her panties on ... I'd never worn panties before. I was still holding them. The fabric felt nice and smooth, probably nylon and spandex. It occurred to me they would feel good against my cock. But most important of all, and uppermost in my mind: if I put them on, I could sniff her panties.

I stood up, and stepped into the panties, pulling them up. They were quite stretchy, I was surprised, and I had no problem pulling them all the way up. Being bikini panties, they couldn't accommodate my erection at all, the top half of my cock was totally uncovered. The waistband pinned my dick against my body about halfway down the shaft. The pressure felt good. I was a bit embarrassed, wearing them in front of April, but not as much as I expected. I pulled the waistband out and released it a couple of times, just for fun. That felt good too.

April evidently liked what she saw: "Mmmm, your cock looks sexy poking out of my panties. I think my pussy just got wetter ... "

My gaze snapped back to April's panties. She was rubbing herself through her panties again, and the damp patch was definitely bigger.

She held her finger up. It was glistening. She beckoned me with it. "Would you like your reward now?"

"You bet."

"Then come and get it." She opened her legs wider, and pulled the panties tighter against her. The wetness spread a little more. I knelt down in front of her, and leaned forward, closer and closer, until my face was about six inches from her panties. I stopped to check out her pussy, close up. Her panties were wet now, clinging to her. What a beautiful sight.

I edged my head forward the last few inches, aiming straight for the wettest part, until my nose touched the moist fabric, then breathed in deeply. Wow, she smelt incredible! So sexy. I loved it, and couldn't get enough.

April's voice filtered into my consciousness: "If you want to keep sniffing, stroke your cock."

I was happy to oblige, my cock was super-hard now, straining against the waistband of my panties.

She added: "But don't cum. If you cum, the game is over, and trust me, you don't want it to be over yet."

I believed her. I didn't want it to end. But I was also seriously turned on. Holding back would not be easy.

April leaned forward and glanced down between my legs. "Judging from how hard your cock is, I think you like my pink panties. Guess what? I'm wearing a matching bra. Would you like to see it?"

Of course I did! She knew I did. I nodded eagerly.

April adopted a mock coy persona. "Well, I suppose I could take my sweater off ... if you put this on."

She picked up a black satin camisole, and held it up by the slender shoulder straps.

So, I had to dress up for her, to get her to undress for me, was that the game? Did it turn her on to see a man in lingerie? It certainly seemed like it. Maybe she didn't get the chance to explore that very often, and jumped at this opportunity. Whatever, I had to decide whether to put the cami on or not. I really wanted to see her sweater come off. I was already wearing her panties. Adding a cami was no big deal. Decision made.

I took the camisole, and put it on. The material felt cool against my skin, and gave me goosebumps. My nipples hardened. The fit was pretty good. It was too short, so my cock was still fully on display, but I figured that likely worked for April, and it worked for me too - it wouldn't get in the way when I started touching myself again, which I assumed she was going to tell me to do very soon.

April smiled, and gave me a look that said 'ok, my turn now'. She was still in coy mode, and lifted up the bottom of her sweater, on each side, inch by inch, slowly edging it up her tummy. She stopped at her breasts, teasing me, putting a little finger in her mouth and acting like she wasn't sure she should carry on. Just when I began to think she might not carry on, she flashed me a devious smile, and lifted the sweater over her breasts, showing me her pink bra. Then she pulled the sweater off over her head with a flourish.

I stared at her chest. It was just the kind of bra I love: a soft, clingy fit, revealing the exact shape of her breasts, with her nipples clearly visible. April looked down at her breasts, and caressed her nipples through the bra. They stiffened at the touch, as I watched, mesmerised.

April looked back at me. "I'm going to give you a choice now: would you like me to take off my bra, or would you like to play with my tits?"

What a choice that was! I imagined each choice being taken, and couldn't decide. I wanted both. Feeling bold, and horny, I ventured: "How about you take off your bra, and then I play with your tits?"

She laughed. "That wasn't an option." She thought about it for a few seconds though, before declaring: "Ok, sure, you can have both, but you'll have to earn them." She sifted through the lingerie next to her on the sofa, and picked out a pair of opaque pink thigh high stockings. She dangled them in front of me. "If you want my bra to come off, you have to put these on."

I looked at them, suddenly feeling a lurch in my stomach. For some reason, this was a bigger deal than putting on her panties or the camisole. Maybe because they were pink? They screamed 'sissy', which wasn't me (despite what I was wearing). I hesitated.

April ignored my hesitation, and looked again at the stockings. "I just remembered these are not stay-ups. You'll need to wear a suspender belt to hold them up, but not to worry, I have one here somewhere." She found it, and held that up too. It was matching pink, a stretchy mesh fabric, with black metal clips.

She finally noticed that I was maybe not going to go for it. If she was disappointed, it didn't show. "Is this too much for you? You can stop playing the game any time, remember? It's no big deal. You just won't get to see my tits. Or play with them." She paused, and added: "Or do any of the other fun things I was planning."