Teen Cocktease Babysitter

I reached back for the cock and held it against my ass, which opened up more readily this time. I sank down on it, letting it fill me up as I watched April play with herself. God, she was so sexy! What was she doing to me?

I raised myself up, then sank down on the big cock again, taking it all the way inside my ass. A rush of pleasure. I shivered. My cock twitched. I lifted up and plunged back down on it again. More pleasure. I felt my orgasm rising.

I took my hand off the cock and put both hands on the floor so I could focus on riding that big cock, lifting almost off it, then thrusting down on it, once, twice more, getting into a rhythm, gyrating down on it, pulses of pleasure edging me nearer to orgasm each time.

I suddenly realised I'd lost count of how many times I'd taken that cock in my ass! It must be five, more like seven, or maybe more - I could fuck April again now! But I was so caught up in the rhythm of fucking the cock and my impending orgasm. I didn't want to stop, I could feel it building with each thrust, my ass was clenching hard, so much pleasure overtaking me, I was locked in to this amazing ass-fucking!

I was rapidly approaching the point of no return, grunting, moaning, shocked that I was choosing to keep fucking this big cock instead of April's sweet cunt, which was tantalisingly close, right in front of my face. She scooted down and pressed her cunt against my face, holding my head against her pussy. I licked her out, which drove me wild, and made me fuck the cock harder and deeper. Oh god, I was going to cum!

April pushed my head back, slid down in front of me and held my cock against her chest as my orgasm overwhelmed me. I sank down on the big cock one last time and came hard, breathless, spraying torrents of cum all over her tits. My cock spurted more and more cum, which she aimed all over her chest and neck, laughing with delight.

When I was finally spent, she held my head with both hands, and kissed me deeply, her tongue seeking mine, so sensual. I was lost.

Eventually, she ended the kiss, held my head in place, and straightened up so her breasts were right in front of my face. They looked so sexy, covered in cum. I gazed at them dreamily, amazed at how much cum I'd unloaded on them, and admired her perfect tits.

Then I heard April's voice, soft and gentle: "Be a good girl Charlotte, and lick your cum off my tits."

It didn't even occur to me to say no.

Her nipples were both coated with creamy cum, and I licked them first. I swirled my tongue over each one in turn, slowly sucking the cum into my mouth, taking my time, making sure not to miss any.

April's voice filtered into my consciousness again: "Don't swallow any of that cum yet, ok? Keep it all in your mouth for me."

I couldn't speak with her nipple in my mouth, but nodded to indicate I had understood. I licked between her tits, gathering more cum into my mouth, then moved higher to scoop up more. It was everywhere!

As someone who masturbates regularly, I know how much cum I normally produce, and this was off the charts. Sometimes I edge instead of orgasm, for a week or more, and when I finally do let myself orgasm, there can be a LOT of cum. But this was like double that.

I licked up to her neck, sucking more cum off her as I went, following the cum trails, back down below her tits, licking up more until there was none left.

April pointed to my softening dick. There was cum all over the head, and more on the shaft. She whispered sensually: "I guess you can't lick that up ... Not to worry, I'll get it for you."

She leaned down and licked the cum off my shaft, then took my cock in her mouth. Oh god! I was still so sensitive, her tongue had my body quivering, it was almost too much. She gripped my dick, and stroked it firmly, milking every last drop of cum into her mouth.

She moved up, her head over mine, and tilted my head back. I got what she wanted to do, and opened my mouth. She smiled sexily, and dribbled the cum from her mouth into mine.

"Good girl. Your mouth is completely full of cum, isn't it?"

I nodded. She reached down and gently held my cock.

"Suck on my nipples, Charlotte. Keep that cum in your mouth, and play with it, savour the taste, imagine you're sucking that cum right out of my breasts."

I licked and sucked her nipples, tenderly, sloshing the cum around in my mouth, coating her nipples with cum and licking it back up.

April whispered: "Do you want to swallow all that delicious cum?"

I nodded, surprising myself.

"Then lick me out."

She let go of my cock, lay back and opened her legs.

"Stick your tongue in my cunt. Imagine I've just fucked some random guy. He came inside me, and I want you to suck all his cum from my pussy while you pleasure me."

I leaned over and licked her pussy, as best I could with a mouthful of cum. It was still sweet, but mingled with the taste of cum now. April started rubbing her clit.

"Good girl, suck all his cum up for me."

I pushed some cum from my mouth into her pussy and sucked it back out. She liked that, and rubbed her clit hard and fast, working herself up into a frenzy. She looked down at me lustfully as she started to orgasm. "Swallow his cum now, Charlotte!"

I met her gaze, opened my mouth briefly so she could see all the cum, and then swallowed it.

She nodded approvingly before relaxing into her orgasm and letting it flow through her, slowing her pace, riding it, prolonging it, her body convulsing with pleasure.

I watched, transfixed, wowed by her incredible sexuality.

After she finally came down to earth, she looked at me, seemingly bemused. "So. You really are a dirty sissy cumslut whore, aren't you?"

I blushed, and stammered: "Not usually ... "

She cut me off before I could say any more: "Well, you certainly are one now."

I thought about that. I wasn't so sure. But she seemed strangely confident.

As she recovered from her orgasm, still trembling, I suddenly remembered the photo she'd taken earlier while I was sucking the cock. I tentatively asked to see it. April was happy to oblige, and sat up. "Of course! It's pretty hot. Here you go."

I was shocked by the image. I barely recognised myself! But it was all-too-clearly me, eagerly sucking cock, made up, wearing pink stockings. I had to ask: "Could you please delete it?"

She thought about it, but I saw she was actually only pretending to think about it. Sure enough: "No, I don't think so."

My stomach flipped. "Why not?"

April replied matter-of-factly: "Because I want to keep it as leverage over you."

I tried to suppress a growing sense of unease. "What for? I mean, why do you need leverage over me?"

She looked at me sympathetically then, as if I was slow on the uptake. "So you keep being Charlotte, of course. My sissy slut. For as long as I want."

I was speechless, and she let that sink in before continuing: "Otherwise, you might be tempted to think this was a one-off. But it's not. I don't care who or what you think you are, or were, but from now on, you're Charlotte, my sissy slut. You'll do exactly what I say, and you know what? You'll love every fucking minute."

"It starts now. I know you just had the best orgasm of your life." She was challenging me to deny it, but I couldn't deny it, it was true. "Don't touch yourself again until I say you can, ok? Can you manage that?"

I nodded, dumbly, not fully committed to that, and still reeling from what she was telling me.

She looked at me critically: "The trouble is, you're a man, and as you demonstrated so perfectly earlier this evening, men cannot be trusted. So I'm going to help you out."

April grabbed something from her bag, and moved behind me. I turned to look but she pushed my face back away from her, so I couldn't see.

Suddenly, I felt cold metal on my wrists, and the clicks of cuffs being locked into place before I had any chance to react.

I was not into bondage. Alarmed, I blurted out: "What are you doing?"

She replied nonchalantly: "Helping you out."

What did that even mean?

April answered soon enough: "The cuffs might not be necessary, but I figure it doesn't do any harm to reinforce the fact that you are NOT in control here."

It was true. I briefly struggled against the cuffs, testing them, but they held firm and felt solid. My wrists were trapped behind me, I was stuck like that.

She moved back in front of me, and picked up the lube. She squirted it on my flaccid penis, and scrotum, then rubbed it all over, covering everything. Her touch felt good, but I was still too drained to get hard again.

April reached into her bag and pulled out a small black case. She unclasped it, lifted the lid, and turned it round for me to see. It was a cock sheath, probably made of silicone, with an adjustable ring on each side at the bottom.

She picked it up, and slid the sheath over the top of my penis, pulling it down until it covered my dick completely, with plenty of room to spare above the head. She gently squeezed my left testicle through one of the rings, tightened it a little, and did the same with the right.

I noticed then that each ring had a much smaller ringlet attached, and there was another one at the base of the sheath. I was just wondering what they were for, when April pulled out a silver padlock. She hooked the open part through all three ringlets, then locked it, and sat back, looking satisfied. "All done. The cuffs on your wrists can come off now, if you want. Or ... I can leave them on for a while, and sit on your face while I explain things to you. Would you like that, Charlotte?"

I hesitated.

She smiled. "I thought you might like that." She pushed me back, and straddled my face, lowering her pussy over my mouth. "Pleasure me."

I licked her pussy eagerly, probing my tongue as deep as I could, and licking her clit, trying to get her off. She fed my enthusiasm. "That feels good, slut. Keep going."

"So, your cock is all locked up now. It's mine, see? Good luck trying to make yourself cum wearing that! I'm sure you will try. But you'll fail. The sheath is too thick for you to feel any real sensations, and there's no access at the tip, just a hole for you to pee through. I hope you appreciate that most cock cages are very constricting, but yours is quite generous, there's plenty of room in there for you to get hard, it won't hurt or anything, but of course it's going to be a major tease for you to be able to get hard and not do anything about it."

She lifted herself off my tongue, and dangled the key to the padlock in front of me. "I'm keeping this, obviously." She picked up a fine silver necklace, hooked the key through it, and put the necklace on. The key hung between her tits. She stood, and started buttoning up a white shirt. Looking down at me, she asked: "Questions?"

Uppermost on my mind was: "How long do I have to wear this thing on my cock?"

April smiled. "Well, I'm still working for you, remember? So I'll be here tomorrow when you get home. If you're a good girl, maybe I'll unlock you ... Will you be a good girl?"

What did she mean? I had no idea but found myself replying: "Yes, I'll be a good girl." But then curiosity got the better of me: "How can I be a good girl?"

April had the answer ready: "Good girls wear stockings and panties. You'll wear them all day tomorrow, under your work clothes, and I expect you to be wearing them when you get home. Understood?"

I replied without any hesitation: "Yes." I was actually excited to do that for her. What was happening to me? I didn't own any stockings or panties though, and told her.

"Not a problem. You can keep those to wear tomorrow. I'll bring more for you. Which you will pay for of course. Any more questions?"

There was one thing. "How come you had a cock sheath with you? Is Hanna a trans girl?"

April took a second to process that, and then burst out laughing.

"Umm, no, Hanna is ALL woman, believe me." She laughed again. "The cock sheath was for you. Only you. I planned all of this. I wasn't asleep when you got home, I was just pretending. I set you up."

My jaw literally dropped.

April looked on me with pity, and reached out to run her fingers through my hair. "Poor baby, you're not the brightest, are you?"

As she left, she paused, adding: "One more thing. I might not be alone when you get home tomorrow."

What had I gotten myself into?