Teen Cocktease Babysitter

I immediately wondered what those things might be! I also wondered what she would make me do to find out ...

But I was curious. I wanted to carry on, and got annoyed with myself for having issues that were getting in the way. Why did I have such a problem with the stockings? They were just clothes. Who cares? Was gender conformity so deeply entrenched in my psyche? No - I was already wearing her panties and cami and felt surprisingly comfortable with it. Maybe that was it - was I secretly worried I'd like wearing stockings? Or that putting them on would suddenly transform me into her sissy bitch or something? My fears seemed ridiculous when I analysed them like that. Plus, I could stop playing the game whenever I wanted. And, yes, I really wanted to see her tits, and feel her up.

Finally, my internal pep talk over with, I reached out to take the stockings from her, and the suspender belt. April happily handed them over: "You're carrying on? Awesome! I can't wait to see you wearing these. After all, you were perving at me wearing stockings earlier - it's only fair I get to perve at you back." She was clearly enjoying this. To be honest, so was I, even though my stomach was flipping at what I was about to do.

I stepped into the suspender belt, and pulled it up, stretching it over my thighs, making brief contact with my still-hard cock, until it sat snugly on my hips, with the clips hanging down.

I picked up the first stocking. April sat up with keen interest: "If you like, I can put the first one on for you." That sounded good to me. I'd watched women put them on before, of course, it's not like I didn't know what to do, but I didn't have a technique, and wasn't entirely sure which way round they went, or if that even mattered. "Sure, that'd be great", I replied.

April took the stocking from me, tucked her thumbs in each side, and pulled the legs with her thumbs and fingers, all the way down to the toe. She held it out to show me. "Like this, see? Lift up your foot." I complied. She slipped it over my toes, and pulled it over my ankles, up to my knee, and over the knee, in one swift motion. Then she worked it up my thigh, stretching out each side and tugging gently until the stocking was right up to the clips. She fastened those, and ran her hands along my calf and thigh, admiring her handiwork. Her hands felt amazing gliding up and down my leg! So smooth, and sexy. I was speechless.

She sat back on the sofa, and teased her bra straps down her shoulders. "Your turn now."

I picked up the other stocking and repeated what April had done, as best I could. It was hard to focus, because she had slipped out of her bra and was holding it against her, moving it around, offering fleeting glimpses of nipple. Between snatching glances at her, I edged the stocking up my leg, stretched it out, and fastened the clips. Done, I straightened up and put my hands on my hips, trying to rock my new look.

April looked me up and down, lasciviously, and I suddenly gained some insight into how a woman feels when a guy is blatantly checking her out. Her eyes settled on my dick. "I see your cock is still hard. So you must like wearing stockings for me, right? Turn around". I turned to face away from her, feeling her eyes on my body, and only then realised I'd done what she told me to do without even thinking about it.

"Yes, very nice", she commented. Then: "Bend over, touch your toes". I leaned down, and even wiggled my ass for her a little bit, as I silently chastised myself for doing her bidding so easily. I looked back over my shoulder at her, intending to tell her that was the last freebie she was going to get.

April pulled her bra away and threw it over my head!

Wow. Just - wow. She had fantastic, smooth, perky tits. They took my breath away, better than any fantasy. Her exquisite nipples were begging for attention, and pointing right at me.

April noticed I was entranced by her tits, and cupped them with her hands. She caressed the nipples with her thumbs. "You want to play with my tits, don't you?" I nodded, spellbound. "Then get over here, get on your knees and get ready to feel me up."

I didn't need to be told twice! I was in front of her in, like, two seconds.

April took her hands away from her breasts, and grasped my hands. She pulled them almost to her tits, but stopped a couple of inches away. "All you have to do, to get to feel my tits, is tell me why you had such a hard time with the stockings. Be honest, and stroke your cock while you tell me." She pushed my hands away, down towards my cock.

I started stroking my erection. I was getting very sensitive now, so I went slowly, using just one finger to slide up and down the shaft, touching the lower half through my panties, while I thought about what to say.

Her incredible breasts were right in front of me, so close, making it hard to think straight or strategise about what to say, so I just told her what went through my head earlier. "I've never worn stockings before. I love how they look on a woman, they are so sexy. You look amazing wearing them, April. But I wouldn't look sexy at all. I would just look like a sissy. Especially with them being pink. That's not who I am, it made me uncomfortable. It's not that I hate sissies or anything, I mean, whatever works for people, right? I'm not judging anyone. It's just not me, that's all. It's too feminine."

April looked down at my legs. "You're wrong, you know. You DO look sexy wearing stockings." She paused, then added playfully: "My sexy little sissy."

I laughed as I blushed. "You're not helping."

"Oh, but I am", she replied. "Anyway, I'm satisfied you answered honestly. You can play with my tits now."

Yes! I straightened up on my knees and cupped her breasts gently, loving the feel of her soft smooth skin. Her nipples were already aroused, but hardened as I played with them. She reached between her legs and rubbed her clit in slow circles through her panties. Then she moved her hand under her panties, and stroked her pussy, putting a finger inside. She gasped: "I'm really wet!" She added a second finger, pushing them deep inside her.

She brought her hand up to her mouth, and smeared her juices all over her lips, then licked her fingers clean with her agile-looking tongue. "I bet you'd like to kiss me now, wouldn't you?"

I nodded eagerly, and she smiled seductively in response. "Good. I want you to ... But, you know, I don't usually kiss boys ... So, if you want to kiss me, you'll have to put lipstick on for me. Can you do that?"

Could I? It would be worth it, and I'd come this far. Why not? I was getting into the rhythm of the game now, and it was stupid to pretend I wasn't enjoying it. I joked: "Sure, but I don't have any handy."

She laughed. "Not to worry, I have some right here, and guess what? It's your favourite colour: pink!"

Why was I not surprised?

April continued: "Sexy pink sissy lipstick to match your sexy pink sissy stockings." She was clearly messing with me now, like she was challenging me to lose my nerve and back out. But my cock was harder than ever at the prospect of kissing her, and tasting her juices on her lips. There was no way I was going to back down now. Which she probably knew.

She picked up the lipstick. "How about I do it for you? I'm guessing you haven't had much experience ...?"

I sure hadn't, and replied as nonchalantly as I could: "Go ahead, knock yourself out."

"Oh ok!" she replied brightly, "in that case I'll add some blush and eyeliner too." She winked at me. I had no idea if she was joking or not.

April leaned in, and started applying the lipstick, in rapid, practiced movements. "This colour is called Manhattan Rose, it'll look great on you, trust me. This'll only take a minute. Touch your cock and play with your balls while I finish up."

I reluctantly took my hands away from her breasts, but my dick welcomed the renewed attention, as I loosely gripped my balls and enjoyed the sensations. My cock was very slippery with precum now, I was really turned on.

I'd barely begun touching myself when April finished. "There, all done. Now for the blush. Just a touch of pink." Evidently she wasn't joking about that. No sooner had she said it than she was done with that too. "Now some eyeliner to finish. Close your eyes. A super-bold pink this time, to complete your upscale sissy look. Ok, done."

I opened my eyes as April tossed the makeup on the sofa, and leaned back to look at me. "Much better!" she declared, "I can totally kiss you now. You look just like a girl. Apart from that cock of yours, obviously." She glanced down at my dick.

"Wow, you are leaking a LOT of precum down there. I have an idea ... "

April put her hand inside her panties again, and fingered herself for a few seconds, then brought her hand up to her mouth and coated her lips with more fresh pussy juice. "Let's make this the sexiest, juiciest kiss ever. Get as much of that precum as you can on your fingers, and wipe it on your lips, then get some more and lick your fingers. I want to taste it when we kiss."

That sounded sexy to me! I coated my fingers with precum, and carefully rubbed it over my lips, trying not to smear the lipstick, then went back for more. Touching the head of my cock felt so good, I was throbbing. April was fingering herself again, and licked her fingers as I licked all the precum off my fingers. I'd tasted my precum before - what guy hasn't? - and kind of liked it. I hoped she would like it too.

April leaned forward, and ran her fingers through my hair, her hands sliding down the back of my head and pulling me into a kiss.

What a kiss! I loved how my lips felt with the lipstick on. She parted her lips and when out tongues met, I shivered all over. It was incredible, the most erotic experience of my life.

I could taste her pussy juice on her tongue, as we kissed for a while, exploring each other's lips, tongues, and tastes. I played with her nipples, tweaking them gently, and she moaned into the kiss.

Her stockinged feet found my cock, and started rubbing up and down the shaft. That felt soooo good - actually, too good! I quickly broke off the kiss and told her: "If you keep doing that, I'm going to cum."

April stopped moving her feet, but kept them pressed against my dick, as she whispered: "How close are you?"

I was on the cusp of orgasm. "I'm right on the edge."

She smiled. "Let's keep it that way." She lowered her feet between my legs, and nudged them up against my balls, creating some nice friction through the panties. Then she leaned back, and spread her legs apart. "Look how wet my panties are."

I looked. They were soaked, clinging to her. "Should I take my panties off now?" When I nodded, spellbound, she added: "Would you like to see my tight, wet, teenage pussy?"

I thought I couldn't be any more turned on, but that offer made my cock twitch, and I felt more precum ooze out.

April replied for me: "I'll take that as a Yes. But, you know, we're still playing the game here, and that means there's something I want you to do first ... "

I dragged my eyes away from her panties to look at her. "Ok." I'd kind of forgotten about the game, to be honest. The kiss had been almost magical, and now she was keeping me on the edge of orgasm with her sexy feet, and offering to show me her pussy. I realised I would probably do whatever she wanted at this point.

April rummaged through her pile of stuff on the sofa. "Although I DO like the way your cock pokes out of the top of those panties to say hello, I have another pair here that will be even better, so you're going to change into them. Ah, here they are."

She held them up for me to see. They were light pink - again with the pink! - high waisted, with an almost-sheer mesh front that looked extremely flimsy. But what really caught my eye was the back: just a couple of criss-crossing straps where the back should be.

April turned them around so I could get a good look. "Aren't they hot? I just got them this week from Victoria's Secret. They're perfect for you. The front will cover your cock, so when you touch yourself - and you WILL be touching yourself - the fabric will reduce the sensitivity a little bit, meaning you can stay on edge for longer. Unless you're so turned on wearing them that it'll be even harder to stay on edge, that's possible too ... could go either way I suppose. Anyway, they're pretty much see-through, so we still get to see your dick, and even better, they'll stick to your dick, with all that precum you've got going on down there." She laughed, adding: "The back straps giving easy access to your ass are just a bonus."

That last comment had me worried, but then I remembered I could stop playing the game any time. I also kind of wanted to put these panties on now, after how she'd described them to me.

April dropped the panties down in front of me, and pulled her own panties tight against her pussy, before teasingly starting to tug them down, then stopping. She raised an eyebrow. "Well? Will you put them on for me?"

I stood up, glad to be off my knees, and pulled the bikini panties down my legs. My cock sprang free. Even that felt good, I was so sensitive now.

Suddenly curious, I asked "How come you have all this stuff with you? I mean, you don't normally carry all this stuff around, right?" I tossed the black panties on to the sofa, and stooped down to pick up the other pair.

April replied casually. "I'm not going home when I leave here. I'm going to my friend Hanna's place, for a sleepover." As if that answered my question completely. It didn't!

I stepped into the pink panties, and pulled them up my legs. They were a great match for my pink stockings, exactly the same light pastel pink. I had to ask about the sleepover. "So you guys hang out, and ... what - try on lots of lingerie and stuff?"

April simply replied: "Yes". Then she giggled. "Lingerie and stuff. Yes, we do that. I'm going to be a bit late actually, she won't be happy about that, but you can make it up to her."

I didn't know what she meant by that and was about to ask a follow-up, but soon got distracted as I pulled the panties up, over my cock. They felt super-sexy on! My cock was contained, barely, the head stretching the top of the panties out. Already, they soaked up some precum and stuck to my cock.

April leaned forward and reached out. She touched the base of my shaft through the panties with her index finger, and slowly inched her way up to the head. She looked up at me playfully as she stroked her finger back down my cock. "Mmmm, that precum looks yummy. I want to lick it off your joystick like a lollypop."

"Be my guest!", I replied.

April laughed. "Not so fast! I want to see more precum first, lots more, and I think I know how to make that happen. Stroke your cock while I take my panties off ... "

She lay back on the sofa, and opened her legs wide. I touched my cock the same way she had, with just one finger, enjoying the sexy feeling of touching myself through the panties. She ran her hands from her ankles, up the insides of her legs, to her thighs, finally to her panties, rubbing herself through them, circling on her clit, and watching me the whole time. I was starting to get close to cumming again, and slowed my strokes.

Just as April moved her hands to the sides of her panties to pull them down, she paused. "Wait, you haven't seen my ass yet! Would you like to? Shall I turn around for you? I bet you've checked out my ass before, haven't you? When I've been wearing tight jeans, maybe?"

She was spot on. Yes, I'd totally checked out her ass in tight jeans! Discreetly, or so I'd thought. My guilty-as-charged look must have given it away.

"I thought so. How could a pervert like you resist?"

I had no answer to that. It was true.

April followed up with: "I'll show you mine if you show me yours. I want to see how your ass looks in those panties. Turn around and bend over."

I did as she asked, feeling self-conscious but doing it anyway. My butt felt naked and exposed.

I twisted my head around to look back at her. "Satisfied your curiosity now?"

"Almost", she replied. "Pull your ass cheeks apart for me."

I reached my hands round to my buttocks, and spread them apart for her. The back straps on the panties were no obstacle, they didn't get in the way at all.

April chuckled. "I bet you never imagined you'd be showing me your asshole like this, huh?"

She was certainly right about that. I wasn't sure what to do, so I just stayed in that position.

"You have a nice ass, actually. A little bit hairy for my tastes, but still, nice and tight. You work out a bit, right?"

I did, and nodded.

"Ok, I'm done with your ass for now. My turn!"

April turned around and got on her knees on the sofa, lowering her head and arching her back so her ass jutted out towards me. Her ass was absolutely perfect. I stepped forward and got down on my knees again for a better look, so her ass was right in my face. She did a slow motion twerk, and I was virtually hypnotised. Each time she pushed back, her ass was just a couple of inches from my face.

She looked round at me. "I'm going to take my panties off now. Stroke your cock."

I touched myself, enthralled, as April moved her hands either side her waist and found the sides of her panties. She slowly pulled them down part-way over her ass, then teased me for a while, before pulling them further down. The gusset clung to her pussy, and she left them there for a minute, before finally peeling them off, pulling them halfway down her thighs, exposing her slit.

She edged her knees further apart, and reached back to pull her ass cheeks apart, just like she had me do earlier. She looked at me, coyly: "I'm going to let you into a little secret. I discovered recently that I LOVE having my ass licked."

That was quite the revelation! I tried to imagine how this discovery might have occurred, but didn't get very far, because April surprised me again by asking: "Do you ever watch porn?"

I didn't need to think about that one. "Yes."

"Me too", she replied. "Mostly lesbian porn. There's this one scene I found, it's so hot! Abella gets her ass licked for the first time, by Kenna James." She paused, then asked: "Do you know who they are?"

I did, and not only that, I recognised the movie she was talking about immediately! It had earned a place in the rotation for my lengthy edging masturbation sessions. "Yes, I know who they are, and I've watched that scene! Several times, actually. You're right, it's hot."

April was delighted to hear that. "Oh, so you get it then! That's cool." She lowered her voice, conspiratorially. "I'll tell you another secret. Hanna looks a lot like Kenna, it's uncanny. Sometimes she even lets me call her Kenna." She giggled. "She wasn't happy about it at first. But then she realised how much it turned me on, and if she let me, she could do all kinds of things to me." She giggled again, this time with a look of wicked recollection.

My mind was racing now! Imagining April with her Kenna look-a-like friend, doing 'all kinds of things'. I could imagine quite a lot.

April interrupted my reverie: "Sorry, was that TMI?"

"Not at all", I replied hastily.

"Good", she answered, pushing her ass back, almost touching my face. I caught the scent of her pussy. "Because I was wondering ... would you lick my ass, and let me call you Kenna?"

I could barely process this new request. I'd never licked anyone's ass, ever. Or been called a woman's name, let alone a porn star's name. April's ass looked so inviting though, and there was the background implication that if I did this for her, maybe she would let me do 'all kinds of things' to her too ...

I wanted to do it, but found myself blurting out "You can't call me Kenna, that name is already taken." I realised then that I'd implicitly accepted the part about licking her ass.