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The Babysitter's Anal Virginity

"Sara loses her anal virginity"

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Author's Notes

"This is chapter 5 in the series "Fun With The Babysitter"."

My name is Sara. I babysit for little Emily, the ten-month-old daughter of Marty and Angela. You might have read my last story in which I described to my best friend Janine how my owners, Marty and Angela, or Mommy and Daddy as I call them, turned me into their submissive sex toy, and how that led to Janine and me having sex together for the first time.

This time, I want to tell you about how Daddy Marty took my anal virginity.

Angela's parents have begun taking Emily for the weekend once a month, so we try to make that weekend really special for me, Mommy, and Daddy. It is so freeing not having to worry that Emily might wake up in the middle of our sex play. Both of them are very dominant with me, and I love it. I've come to realize that I am a true submissive. I'm submissive not only to Marty and Angela, but to Janine as well.

At our last encounter, as I was leaving, Mommy Angela gave me a butt plug. "We expect you to wear this at virtually all times until next weekend. Only remove it when you need to poop. Once a day, you may remove it to clean it and relubricate it. We want you fully prepared to have your anal virginity taken from you."

I blushed deeply at her words, but I said to her meekly, "Yes, Mommy. I'll do as you say."

"Bend over the arm of the sofa right now!" she ordered me.

I did as I was told, and Mommy then pulled my thong down and lubricated both the plug and my anus with anal lube. She pushed the plug into my butt, and as it slipped in, I gave an audible, "OHHH!" She took a picture of me then, before pulling my thong up.

"Stand up!" she ordered me, and then showed me the picture. I know I blushed again at the sight of my ass stuffed with a butt plug.

"Go home now, little girl! If you are with Janine, you may show her, but under no circumstances are either of you to remove it!"

"I promise, Mommy. I love being the property of you and Daddy Marty!"

I walked home then. The plug felt so weird in my ass as I walked, but I was already growing to like the sensation. I had a feeling it was going to be a difficult week, as I anticipated the events coming up next weekend, but it would be a sweet torture.

When I woke up the next morning, I got in the shower. I reached behind and pulled the plug from my ass. It was such a deliciously strange feeling when it popped out. I looked at it carefully, filled with wonder and lust that this will be in my ass for an entire week. I washed it carefully, and after I dried myself, I lubed up both the plug and my butt. I reached behind me, found my asshole, and pushed the slick plug back inside me. Oh my God, it felt so good sliding in. I got it nicely nestled in there, and I got dressed.

I couldn't wait to call Janine. I told her about the plug, and she said, "Oh my God, I want to see it. Come over right now. My parents are out for a couple of hours, so we'll have some time!"

I raced over to Janine's house. As soon as I was inside, she said, "Show me! Right here!"

As I did with Marty and Angela, I bent over the arm of the sofa. Janine tugged my thong down, and there it was. Bright blue and nestled in my ass. She reached to pull it out, saying she wanted to really look at it.

"No, no! You can't! Mommy made me promise not to let you remove it, and I can't disobey her!"

"Then, I am going to spank you, you naughty slut!"

While only Mommy and Daddy OWN me, Janine has a lot of control over me as well. I've become like putty in her hands.

She lifted her hand and began swatting my cheeks over and over. She told me how pretty my ass looks as my cheeks jiggle and turn pink. She spanked me hard, but oh my God, it felt so fucking good!

She finally stopped. She grabbed me by the hair and yanked me to my feet. We clutched each other in a tight embrace and kissed passionately. My hand went under her shirt, and I played with her beautiful tits. I think mine are nice, but hers are incredible. My pussy was dripping wet. I needed her so badly right now!

We raced up to her bedroom and shed our clothes. Naked, we fell onto the bed, and almost instantly went into a 69 with me on top. Our tongues dove into each other's dripping cunt. Since I was on top, I was sure I was also giving Janine a beautiful view of my butt-plugged ass. We ate one another until we both exploded in orgasm all over each other's faces.

After we came, Janine said we'd better get dressed. Her parents would be home from shopping soon. Reluctantly, we did so, and I headed home. As we said goodbye, I told her, "This is going to be a long fucking week until I see Marty & Angela again."

Oh, it was indeed a very long week for me. Not only was the anticipation of what would happen to me keeping me soaking wet, but the butt plug in my ass all the time was adding to my horniness and desire.

When Friday finally arrived, I called Angela and told them I would be there at 4 pm. I wanted to be out of the house before my parents got home from work, because I didn't want them to see me in the slutty outfit I was going to wear.

They loved me playing the schoolgirl role with them, so I ordered a schoolgirl costume from an online sex store. The outfit consisted of a blue crop top with short sleeves, a pink, pleated micro mini skirt with a thick blue waistband, blue tulle trim, a pink satin tie, and pink satin hair ties. I topped it off with white thigh-high stockings and 4" blue pumps.

"I look fucking amazing!" I thought to myself as I looked in the mirror. I didn't bother with underwear. The skirt was so short that it only barely covered my pussy and ass, provided I stayed completely upright. I probably should have driven to their house, but I was so horny and so anxious to show myself off, I decided to walk, since it was only a few blocks away.

I felt so amazingly slutty as I sashayed to Mommy and Daddy's house. I was too lost in lust to give a shit if neighbors saw me.

I rang their bell. Marty answered the door, and his mouth dropped in shock when he saw me. I loved that I gave him this reaction!

"Hi, Daddy! May your little girl come in, please?"

I came in, and there was Angela in black faux leather and 5" black heels. I knew I was going to be treated severely, and I relished it.

She circled me, clearly inspecting me.

"Bend over and grab your ankles," she ordered me.

My skirt hid nothing. I knew she wanted to make sure the butt plug was in place. My pigtailed hair brushed the floor in this position.

"You are such a slut, walking over here looking like this," she told me. She spanked me so hard then that I almost fell over. I had to let go of my ankles to brace myself on the floor.

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"I said hold your ankles, you little slut!"

I did so again, and when she spanked me again, I was more prepared, so I was able to hold still.

"Look at her, Marty. Are you sure you want to fuck the ass of such a dirty little whore?"

Daddy just laughed. "You know I do! And you want to watch!"

"I want to do more than watch," she said. "I didn't tell you, but I bought a strap-on. I'm going to fuck her ass after you finish with her! Let's take her upstairs."

They stood me up and attached my collar around my neck, and then hooked my leash to it.

"On your hands and knees, little pet!"

I did as I was told and was led upstairs to the bedroom that way, with Mommy leading me on the leash.

"Up on the bed, little pet!"

I got onto the bed and remained there on my hands and knees.

Mommy came to me and gently caressed my ass this time, rather than spanking it. "Such an obedient pet! You are getting a special reward today. Your very first anal fuck. Are you looking forward to it, little pet?"

"Oh, yes, Mommy! I've been dreaming of it all week. I know my bottom is prepared now!"

She took the butt plug between her fingers and pulled it out with a little "POP!"

"Look, Marty. Look at our pet's pretty little gaping bunghole!" She slipped a finger into my butt. "She's ready for you!"

I saw Daddy was naked now, and his big cock was hard and throbbing with desire for me, and for my virgin asshole. Mommy slathered anal lube all over his cock and then applied it to my ass as well. Her fingers felt so good massaging the lube into my anus.

Daddy got onto the bed behind me. Mommy pushed my head down onto the pillow, so my butt was upraised and ready. Daddy took hold of me by the hips and pressed the big mushroom head of his cock to my virgin asshole.

"Are you ready, little pet?"

"Yes, Daddy. Please fuck my ass!"

He pushed, and my sphincter surrendered to the invader. I howled in pain at this intrusion. I hadn't thought it would hurt this much since the butt plug was in my ass for the entire week.

Daddy stopped and let me adjust to the sensation of a cock in my ass.

"Go ahead, Daddy. I promise I won't scream anymore!"

He then began thrusting his cock in and out of my butt. Mommy got underneath me and began licking my clit. Oh, that felt so wonderful! It helped me relax, and as Daddy picked up the pace, his cock started feeling better and better in my ass. They were both being so sweet to me, and I felt so proud that I was being such a good slut for them.

"Fuck me harder, Daddy! Don't hold back! I can take it no matter how hard you fuck me!"

Those words made Daddy begin to really ram my ass. He grunted with the exertion of each hard thrust. It was so strange to me how it both hurt like hell and felt absolutely divine. Of course, Mommy lapping my clit and finger-fucking my cunt certainly improved the pleasure aspect! I was cumming all over Mommy's face when I heard Daddy cry out, "Oh God, I'm gonna cum!"

He gripped my hips, and I felt his seed shoot deep into my ass. Pulse after pulse squirted into me until it finally subsided, and he popped his cock from my hole.

"Oh my God, Angela, look at her asshole gaping open!"

"Clean his cock, Sara!" Mommy told me, as she climbed from between my legs to view my slutty asshole. She buried her tongue in my wide-open hole, lapping Daddy's cum up, as it bubbled from my butt. Daddy came around to my head, and I greedily took his softening cock between my lips. I tasted his semen and my own ass on it, and I loved the flavor. I rubbed the shaft all over my face.

"Am I a good whore, Daddy?"

"You are the best, Sara! You are the best babysitter, and the best slut too! You're not a virgin anywhere now!"

Mommy got in front of my face now. She kissed Daddy's cock, and told him to sit back so I could lick her face clean. I licked her, and we kissed, and again, I tasted my ass on her face and tongue.

"We're not finished with your ass at all, little pet!" she whispered to me. "Wait until you see what I have for you!"

She got up and left the room. We could hear her in the guest room, opening a drawer. It must have been a couple of minutes later that she walked back into the bedroom. She had a harness around her waist, and attached to it was a strap-on cock that made Daddy's impressive cock look almost small.

My eyes opened wide. "Are you going to fuck my ass with that thing, Mommy? You'll break my asshole, it's so big!"

"If you are really going to be a slut, you will take it! ARE you a slut, Sara?"

"Yes, Mommy. I really am. I mean, I think I am!" I squeaked out quietly.

She handed me a vibrating dildo. "Use this on your pussy while I fuck you. It will relax you just like my tongue relaxed you a few minutes ago."

Daddy got the lube and really smeared it all over the strap-on, and then he poured a bunch of it onto my ass, and even smeared a lot of it inside the walls of my butt.

I turned on the vibrator and pressed it to my clit. Instantly, pleasurable sensations began inside my body. I was moaning in self-pleasure until Mommy pressed the head of her strap-on against my butt and pushed inside me.

I saw stars when she did it. "Oh my fucking God, it hurts!"

She stopped and let my ass adjust to the length and thickness of her fake cock. The sensations in my cunt and my pride in what a total slut I had become overcame the pain, and I began to cum. Mommy started fucking my ass then, in and out. I pressed the vibe harder to my clit, and I was cumming non-stop. What an amazing mixture of pleasure and pain this was, and I began loving it.

Daddy had his phone out and was making a video of my wonderful degradation. I looked at Daddy and smiled. "Wait until Janine sees this!" I said to him.

After a while, Mommy stopped. She pulled the fake cock from my ass and told me to clean it. I eagerly took it between my lips and mouth fucked it as if it were a real cock. Again, I could taste my own ass on it. Briefly, I thought, "I should be so ashamed of myself, but I'm not. I'm PROUD I'm such a slut!"

Daddy showed me the video, and we all watched it together. I couldn't believe how gaping open my asshole was! I had no idea that would happen.

"It won't stay like that, will it?" I asked worriedly.

Daddy chuckled. "No, little pet, that is a very brief phenomenon. It's almost back to normal already."

"I love you both so much!" I told them. "My sex Mommy and Daddy! I love being your property!"

The weekend was just getting started!

Published 
Written by nyguy51
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