I think I knew I was dreaming, but how could I be sure? I was fucking some girl who looked familiar, Annie maybe? But hadn’t we had sex recently? What this Annie or her sister? Did Annie have a sister? Whoever it was had the tightest pussy and I was already seconds away from exploding ins-

My eyes shot open as I felt the sudden loosening of cum from my cock. In my hands was a mane of dark hair planted firmly in my crotch, surrounding a feeling of undulating tongue and throat. I held Annie’s head there as I bucked through my morning release. It took me a few more seconds to become aware of the gagging sounds and hands pushing against my thighs, then I let go and Annie sprang up, my seed dripping from her nose and mouth, eyes red and puffy with tears. I chuckled as I looked at her. “You okay down there?”

She looked down at me, finished coughing and smiled. “Yes sir, it was just a bit much, that’s all.”

“You did very well,” I held her cheek in my hand. “So well, in fact, I think you deserve a reward.” Her eyes widened, but whatever she wondered her reward would be she didn’t expect what I pulled out the bedside table drawer. It was a small flat box with a red ribbon bow around it. I sat up against the headboard, handed it to her and invited her to sit back against my in my lap. I wrapped my arms around her with her head on my shoulder as she opened the box. Inside lay a thin black collar, like a cat’s, with a detached, engraved, circular pendant. She pulled it out and read the inscription: “Master’s Little Whore.”

She looked up and kissed me hard. “Thank you sir, I love it.”

“Hold up a second, slut,” I said, pulling the collar but leaving the pendant. I opened the clasp and she leaned forward so I could attach it around her neck. It pressed flush against her skin but wasn’t tight at all. “You are to wear this whenever we are together, but in public it’s up to you. I want you to always know and feel who you belong to, but I don’t want your parents getting wind of our… misadventures.”

Mention of her parents brought a flash of reality across her eyes, but I quickly kissed it away. I then pulled out the pendant. “This is something very special,” I said warmly, “and while you’ve done incredibly well there are just a few more things for us to do before you earn this. I wanted you to suck me awake and you’ve certainly done that. You have no problem taking a cock in your mouth and throat. Our sex is amazing, and I care about you very much.” I played with the jewellery in my hand. “But to earn this, to be a true Little Whore for me, I need to know you’ll do everything I ask.” Her eyes glazed in fear. I smiled and nodded. “I do mean everything. So how about we talk about our plan for today?”

She snuggled back into me and smiled nervously, my arm wrapped around her naked form, clutching her full breast in my free hand as I dangled the pendent in front of her. I brought my lips to her ear and whispered: “Today’s the day I fuck you in the ass.”

I felt her physically gulp.

—–

I made us a fried breakfast of French toast, waffles and egg. Unoriginal, but it was warm, edible and filling: exactly what my little whore was gonna need for today. As we sat across from each other at the dining table I was cheerfully eating away, wearing a pair of boxers and a half open shirt just to keep away the morning chill, while Annie was sitting nervously in nothing but her collar, her nipples erect atop her firm teenage tits.

“You’ve done so well already this weekend,” I praised her, trying to begin a conversation. “Far further than I’d hoped for just one evening, and we still have today and most of tomorrow together.”

She said nothing and just picked at her food.

“Annie, look at me.” She’d zoned out and didn’t hear.

“Slut, look at your Master.” That got her attention and her eyes snapped to me. “Your mind is elsewhere. Are you nervous about your ass?”

She nodded slowly.

“Is it something you’ve ever thought about doing?” Whether she was interested or not didn’t make a difference to me, I planned on making her my three-hole whore regardless.

She was still shy about her wants and needs. That shyness was an incredible turn-on most of the time, but sometimes it was just frustrating when I wanted a clear answer. “Annie?” I prompted.

“I’ve… I’ve always been curious when I heard people talk about it in school. I just never really thought I’d try it.”

I wondered for a moment as I finished eating. “I’m going to take your asshole today.” She looked away shyly. “But let’s start with some… education first, shall we?” She looked back at me curiously. “You brought a bag with you, did you bring a change of clothes?”

She nodded “yes sir.”

“Anything sexy?”

She swallowed hard. “Yes sir, I think so.”

“Go get changed upstairs then meet me on the couch.”

She nodded and ran upstairs, and I grinned at her tight, globular buttocks as they walked away from me.

Moving to the couch I turned on the TV and found my porn library. I knew exactly what video I wanted.

The stairs creaked and Annie walked in. I was awestruck by her. She’d put her hair into pigtails, wore a white blouse that was open down to her chest with a lacy pink bra showing through beneath, with a red tartan skirt that ended just where her thighs began, and her pale bare legs led down to a pair of black Mary Janes. Now, I didn’t have a particular kink for the schoolgirl look, but holy fuck she was hot. It was all I could do not to rush from the couch, pin her against the door and take her from behind that instant.

“Please sir, may I sit down?”

“O-of course, sit down,” I stuttered, trying to recover my senses.

As she sat I noticed the pink and purple glitter eye shadow, the thin black mascara around the eyes, the reddened cheeks and bold, bright red lipstick. God I wanted those lips around my cock again. My cockhead sliding through the narrow gap of her throat was a better feeling than even her tight, warm little cunt, but I resisted the urge. Today I wanted to cum in other holes.

Annie made to sit next to me but I sat back and patted my lap. I guided her down so she sat back against me with her legs on the outside of mine. When I opened my legs, hers opened, revealing her panty-covered molten hot mound to the air – and my touch.

She slid back against me, her muscles rigid with nervousness. “Relax,” I said smoothly in her ear. I ran the tips of my fingers down her thighs, enjoying their tension and enticing her to relax them. “I’m not going to hurt you,” I teased. “At least, not in a way you won’t enjoy.”

Leaving my right hand to stroke her thigh, I gently moved my left up her leg and over the taut cloth of her bikini-style pants. My fingertips danced in the heat radiating from her core, applying firm presses to her sensitive button and lips. She cooed in my ear and tried turning to kiss me, but I gently moved apart. “Just watch the TV.”

I pressed play and the TV sprang to life, but with the volume low. Two apparant 18 year olds, though they looked more like they were in their mid twenties, were on a bed cuddling up and making out. They were dressed casually, but already the brunette was slipping her hand under the blonde’s tee and working it up to her breast. Their mouths mauled at each other as their hands worked over their bodies and tore into their clothes. Within about half a minute the brunette was pulling the blonde’s tee over her head and diving for her nipple, pulling it taut with her teeth before releasing it and sucking it into her burrowing mouth.

With one of my hands now slipping inside Annie’s panties, I worked the other up inside her blouse and bra and pulled at the firm pink nipple that was desparate for my touch. She was already moaning and squirming fitfully in my lap.

Onscreen, the first person POV shifted downwards as the cameraman moved onto the bed and aimed his lens at the blonde’s hand pushing into the brunette’s lacey black underwear. The brunette tore herself from the blonde and smirked at the camera, which followed her hand to the cameraman’s pants, which she unzipped and opened to release his cock. She dived down onto it, only taking half into her mouth but rapidly pistoning up and down on it.

Annie’s innocent looking face was staring enraptured at the TV, moaning at both my ministrations and the spectacle. “Would you like to be sucking on me right now?”

“Yes, god yes I would, sir.”

A few seconds later and the brunette shifted closer to the camera as the blonde disappeared behind her. The camera moved to a side view and revealed that the blonde had laid down beneath the brunette and had her mouth nestled firmly into her co-star’s loins.

“Would you like me to eat you like that?”

“Yes sir, yes please sir.” Annie now had one hand on her other breast and the other hand slipped behind her trying to get inside my pants.

“What about another girl?” I licked her ear. “Would you want some other innocent looking girl sucking and eating you like that?”

“God sir, yes, fuck yes.”

I was delighted. I would definitely be using that knowledge.

The brunette stopped her sucking to quickly strip off her tee and revealing her braless tits. “They’re nearly as big as yours,” I said as I exposed her tits to the chilly air and grasped both her hands to maul her own breasts. “Would you like to hold them like this? Kiss them? Suck on them?”

“Yes sir, fuck yes sir.”

I undid and pulled down my boxer shorts and let my hard cock bounce free against her boiling cunt. Without a word I used one hand to push her ass up and the other to guide my cock into her slave cunt. Annie sat upright and controlled her descent, slipping gently down onto my cock. She breathed heavily as she adjusted to the fresh invasion and I counted my lucky stars I got to do this again. On the TV, the brunette had unlocked herself from her friend’s mouth and was laying back naked on the bed. The camera guy was aiming at her juicy cunt as he swiftly entered it and began fucking her with aplomb.

Annie’s moans were delicious and her own wet cunt was tight as hell, but I wanted to get things moving and she couldn’t get a steady rhythm going. So, I held her hips tightly to me and slid off the couch to the floor, using our momentum to push her torso forward. She caught herself from hitting the floor face-first by putting her arms out, leaving me to raise my hips and begin pounding into her fresh pussy doggystyle. Her breathy moans turned to outright breathless groaning as I fucked the air right out of her.

She begged me for release even as she peaked and rushed into her climax. With round one over, I slowed my fucking to a stop and gave her ass a playful slap.

“Well done little slut, very well done.”

She moaned hushed little thank yous as she lay collapsed on the carpet. Leaving my cock inside her, I wet two fingers with her pussy juices and pushed one into her asshole up to the second knuckle, wiggled it a little then pushed in the second one too. Her ass was tight. Very, very tight.

“Look up, little slut, watch the TV.” She did as I ordered and witnessed the camera guy slip his cock from the brunette’s cunt only to be immediately swallowed whole by the now-naked blonde. Annie made to get up and turn around, probably to mimic the action, but I smacked her ass firmly and told her to keep watching.

The blonde stop sucking and removed the cock, positioning the head at the closed rear star of the brunette. She dribbled onto her friend’s asshole then pushed the cock inside. It went in fairly easily, and he started fucking her vigorously. Now, I know these are paid, professional actresses with plenty of anal experience and probably lots of hidden lube, but I needed two things. The first was to see Annie’s reaction to all of this, and the second for her to see that taking a cock in her tight teen ass was not only efficient but pleasurable, whether I knew it was fake or not.

From the coffee table I took a small bottle of lube I’d brought down earlier and squeezed it gently over my cockhead and her sphincter, using my fingers to push it down inside her tightest hole.

Annie was enraptured by the action on screen but she snapped to attention as she felt my large cockhead press against her ass.

“Are you ready for this?” I asked.

“I… I don’t know.”

I took the small black box from the table, opened it and tossed it to the floor in front of her. The pendent gleamed in the light, the black letters clear with their message. “‘Master’s Little Whore’,” I said. “That’s what you are, right Annie?”

“Yes, yes sir.”

“But how can you be my little whore without allowing me everything?”

She nodded. “I want you to have me, all of me, sir.”

“Then beg me.”

She looked up and stared at the TV. What was going through her head? Did she really want this?

“Please sir, please fuck me anyway you like.”

“Anyway I like?”

“Yes sir.”

“You mean your ass?”

“Yes sir.”

“Then be specific, Annie. Beg me to fuck your ass.”

I saw her look to the pendant. Was it as much of a reward for her as I hoped it was?

“Please fuck my ass, sir.”

I pushed inside.

Not everything goes to plan. Try as I might, with as much lube as I could, there was no way my cock was going into Annie’s tight ass without causing a lot more pain than was fun for her. After a few minutes of trying, I slipped into her pussy and gave her the fucking of her life. Now, she suckled at my deflated cock, cleaning it up for our next activity. I could sense she felt defeated. I’d built it up so much for her and it wasn’t gonna happen. I had an idea though, but how to propose it was a different matter.

After our rendezvous in my office on Thursday, my secretary Jodie had made it very clear that she wondered Annie was extremely cute and would love to join us properly, if I was up for it. Annie’s recent reveal that she’d be interested in another girl meant that I wanted to put two and one together to make three, and maybe get help with that final virginity.

I had switched the TV to a slow blowjob scene and picked up my phone while Annie was distracted. A couple of text messages later and we had a dinner date for the evening.

Time stretched into lunch and we cleaned ourselves up and made some food. Annie was obviously feeling a little bummed out (pun not entirely intended) at “failing” and I needed to change the mood. I kept my hands on her as much as efficient, holding her, feeling her. I kept kissing her, meshing those wonderful lips with mine and generally smiling. I was the most excited I’d been in years and wanted her to know it. She was buttering some bread as I turned on the radio. It was a slow number, so I stepped up behind her, put my hands on her blouse covered hips and had her sway with me. She chuckled and leaned back, her head on my shoulder.

“I love… this,” I said hesitantly. Damn, that was close. Unexpected too. She breathed out heavily and seemed to sink back into me.

“Me too,” she smiled as she whispered the words.

I kissed her then broke aside to finish my own lunch. We sat at the table, me in boxers and a short and her in her makeshift college uniform. It felt slightly awkward, but this time it was her turn to try and fix the mood.

“I’m… sorry,” she said slowly. She looked away from me as she continued. “I know you wanted my… you wanted to… fuck me… there. I’m sorry I couldn’t do it.”

I stifled a laugh. “Annie, it wasn’t anything you could or couldn’t do. These things take time to build up to. I’m the one who’s sorry I rushed it. And I’m sorry I made such a big deal out of it, it really isn’t one.” I got up and retrieved the boxed pendant, dropping it open on the table in front of her. “This… relationship we have going on. Is this what you really want?”

She looked up at me sincerely and nodded enthusiastically. “It really is.”

“Are you sure? I’m older than you, and I’m sure this isn’t how you imagined your sex life starting. There are guys out there your own age that…”

“They’re boys and they treat me horribly. You showed me that.” That seemed to have sparked her. “My god, I’ve dreamed of what we’re doing, I just didn’t know it. I’ve never been exposed to it, but it feels so right, you know? Like we’re meant to be doing it.” I’d never seen her so animated.

She pushed the box back towards me. “I’m going to earn that because i want it. I want to be everything for you because it’s what I truly want. You’ve shown me how good I can feel, how hot, how fun this is. I love the way you look at me like you want to devour me, because I want to devour you too.”

She jumped from her chair, came over and straddled my lap. She looked me dead in the eyes and gave me a peck on the lips. “I’m going to be Master’s Little Whore and you’re going to look after me and treat me like I should be treated, like you have treated me, like a woman for the first time in my life.” She hugged me close. “I love how you make me feel.”

An couple of hours later, Annie slid off my cock, a fresh deposit of semen leaking out of her vigorously fucked pussy. She nestled into my arms and purred in contentment. I was about to attack her lips when the doorbell rang.

I jumped up and made for the door but Annie grabbed my arm and held me back, whispering “you’re not meant to be here, remember?”

“Oh shit,” I laughed. Annie scrambled to put on my shirt and do up the top few buttons as she walked to the door. Feeling cheeky, I slid into the gap between the door and the wall just behind her.

She opened the door and peeked her head around, making sure to keep her naked lower body out of sight. “Mom? Hey, er… what are you doing here?”

“I brought you all dinner for tonight, so you didn’t have to cook,” Luna’s voice was high with excitement. “Figured I’d come help you for a while, since you have the whole weekend alone with them. Where are they anyway?”

Annie took a second to think, then said in a whisper “We’re playing hide and seek. I’m meant to be hiding.”

“Oh!” Luna sounded as if she’d been caught in a plot. “You’re doing okay though?”

Feeling mischievous, I slid my hand over Annie’s belly, then slowly pushed my fingers lower. I rubbed her clit before dipping two fingers between her cum coated lips and rubbed her gently. Annie suppressed a shudder as she replied. “Oh yeah, we’re having the best time. I’d better go though, the boys are looking for me.”

“Of course!” Luna whispered back conspiratorially. “Here, take these. Oven on 350 for half an hour, okay?”

Annie took the bag from her and thanked her. She was about to say goodbye, when Luna suddenly stopped. “Wait a minute, are you sure you’re not hiding Dylan in there?”

I removed my fingers from just as Annie’s tone changed to one of fear. “Dylan? No, we broke up, remember?”

Luna seemed to take a second to judge her daughter’s reaction. “That’s odd, I saw his car just up the road.”

“Maybe he’s visiting one of her other girlfriends?” Annie said angrily.

Now Luna definitely believed her. “Oh he’s like that, is he? I’m sorry, men really can be assholes sometimes.”

“He’s not a man, just a boy, and I hope I never see him again,” Annie said with finality.

Luna must’ve smiled. “That’s my girl. Call me if you need anything, alright?”

They said their goodbyes and Annie closed the door. She looked at me with fear in his eyes. “What’s he doing here?”

I nodded to the bag. “You put the food in the fridge and I’ll find out.”

She picked up the bag and took it into the kitchen, and I couldn’t help but lust after the ass cheeks that swerved just under the hem of my shirt.

At the TV I went back through the exterior footage of the last couple of hours and easily found Dylan lurking around. As I went back through his steps from camera to camera I saw that he’d been here for a while and not only had he seen me and Annie fucking downstairs, he’d filmed it on his phone too. I switched back to the live view and found him outside the back door, having run there when he saw Luna coming.