The Babysitter

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She and Gina console heartbroken teen girl.
2.1k words
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Part 1 of the 2 part series

Updated 10/29/2022
Created 10/13/2000
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I can't wait to see you tonight," my girlfriend, Gina, said to me over the phone.

"Me too," I sighed. I had been idly pressing my pussy against the kitchen counter the whole time that she had been talking to me.

"Did you get a babysitter for Eve lined up?" she asked.

"Yeah," I said, "The girl across the street."

"How old is she?" Gina giggled.

"She's only JUST turned eighteen you big dyke!" I said. "Besides, its so handy to have Becky so close and not to have to worry about using someone I don't know, especially after hearing all those babysitter horror stories!"

"Yeah but is she cute?" Gina continued to kid me.

"She's very pretty," I said. At first I had be taken aback by Gina's teasing, but as I answered I suddenly had a vision of my short-haired butch girlfriend fucking the little high school girl next door with a strap-on. Just then there was a knock on the door and Becky entered the front vestibule.

"Gina, she's here. I gotta go," I said as I quickly leaned away from the counter and straightened my dress.

"Okay, baby. I'll see you when you get here. Love ya."

"Okay see you, sweetie." I said and hung up the phone. I was just turning to say hello to Becky when all at once she burst into tears. Surprised, I stopped in mid sentence and went over to hold the now sobbing teenager.

With my arm around her shoulder, I led Becky over to the large sofa and asked her what was wrong. "Everything," she cried, "My boy friend wants to dump cuz' I won't let him---you know, let him....."

"You mean go all the way," I asked, still kind of thinking about what I had pictured Gina doing to her.

Becky only nodded and cried even harder. "Boys can be such pigs," she said.

As I held Becky close, I could feel her cheek up against my chest. I was wearing a thin silk dress, and the feel of the teenager's face against my firm breasts was starting to make my nipples hard.

Over the last two years Becky had blossomed into a very pretty young girl. She had piercing green eyes and dark hair that was usually in a simple pony tail. Although not entirely filled out, she had a lean and lanky frame with just enough curves to let you know she was definitely female. She had narrow hips and was a bit knock-kneed. An adult man could have palmed her round little butt in one hand. Her breasts could best be described as perky, and while they weren't big, they looked just perfect on her youthful body.

Earlier that summer, while Becky was over using the pool, I had noticed that she looked wholesome yet very sexy in her tiny white bikini. I will never forget how the thin material of her suit clung to her body when she crawled out of the pool. The funny thing was that she had no idea of the affect she had on not only boys, but anyone who saw her dressed so skimpily. She had met Mick that day, and they had started dating.

I almost was pissed off as I realized how that little bastard must have hurt her. Fucking men are all the same. Now it was up to me to calm the girl down and maybe help her through her problem. After a few minutes Becky relaxed, and she started to tell me what had happened.

"We were at my house yesterday while my parents were still at work," she said ,"and he asked me if he could kiss me..."

I wiped a tear away from the corner of her eye as she continued. "I thought it was so sweet how he asked me...so we started kissing...and it was real nice...but then he started touching my butt but it tickled....I didn't want him to stop kissing me, I just wanted him to stop tickling me..."

"It's okay," I told her.

"I told him to stop, but he took it wrong and started to get all mad...and he called me a tease, said he was tired of messing with me, and left."

"Don't you worry, sweetie," I said. "Its not your fault. Mick was way out of line trying to push you into something you didn't want to do."

"But I want too, I just don't know how!" she sighed.

"What do you mean, Becky?" I asked.

"Well..." she stammered, "...I just...I mean...I've never done anything like that, and I don't know...I'm scared.Could you help me Miss Andrews? I really need help with this"

I didn't really know what kind of help she was looking for. I knew what kind of help I WANTED to give her, but surely I could never get away with that. Not knowing where the situation was going, I looked into Becky's eyes and nodded in the affirmative. "What is it you would like to know dear? " I asked.

"I don't know..." Becky said as she shyly pulled away from my embrace. As she shifted around looking at the tips of her shoes, I had my first chance of the evening to notice how she was dressed. She had on a demure white button shirt that looked like it was about three sizes to big for her and very baggy khaki shorts. The only skin showing was her skinny knees between the hem of her shorts and her white knee socks.

"Have you ever fooled around with anyone before?" I asked.

"No..." she said quietly.

"Nothing?" I asked.

"Nope," she answered, "only kissing."

"Do you ever touch yourself?" I asked.

"You mean, down there?" she whispered as she hestitantly pointed towards her groin.

"Yes," I said, "Have you evet mastrubated?"

"Oh no!" she answered. "Do you?"

"Yeah," I answered, but, to be honest, I was starting to get bored with her. Eve was still asleep upstairs so there was no real hurry to end this conversation, but I did have an eventful night planned with Gina. I had been so turned on just a few seconds ago that I really wanted to get over to Gina's and get to fucking while I was still horny. Just when I was starting to wonder if this backward young thing would ever get around to whatever it was that she had on her mind I noticed that she had starting unbottoning her blouse. I have to admit, even I was a little shocked when she pulled open her shirt exposing the beautiful pink lace bra that gently cupped her tiny bosom.

In awe, I watched as she reached inside her shirt and cupped her hands over her cute bra. "I get so scared when Mick touches them," she said, "and I feel so squishy inside...I can feel my nipples get hard and I get so flustered I just stop him...Look, see them now, they're getting hard just from me touching them."

Beneath the lacy under thing I could see the outline of rigid nipples showing through the sheer fabric. Without thinking about it, I reached out to caress one of the hard nubs. Becky let out an audible sigh as I gently took the tip of her breast between my thumb and forefinger. I pinched it softly and then flattened my palm against her tiny tit. "Does that feel awkward?" I asked her.

"No..." the girl replied. She looked up at me, and her saw that her eyes had grown wide with excitement and fear.

"This is all he wants to do, " I said. As I was talking I slipped my hand behind Becky's back and unclasped her bra, letting it fall away from her young chest. I stopped for a second to look at her little titties. The tiny mounds were just large enough that they curved up slightly. Her nipples looked a little too big for the size of her breasts and they bulged out like tiny cherries in her current state of arousel. So much for my date. Gina would have to understand.

Reaching out towards her again, I cupped both of Becky's tits in my hands, bent my head down, and flicked my tongue over the end of one nipple. Inhaling sharpely, Becky inadvertantly arched her back, pressing her entire breast into my mouth.

"Miss Andrews!" she said as she tried to pull away. "I shouldn't be doing this!"

Letting her step away from my touch, I looked at her, smiled, and said, "Take off your shorts, Becky."

There was an awkward moment as she stood staring at me. Finally, the young girl undid her button and zipper and let the khakis slip down over her girlish hips. Wearing nothing but her unbottoned shirt, white knee socks, and baby blue cotton panties, Becky stood still, waiting for me to tell her what to do next.

"Come over here and unzip my dress." I told her. Without saying anything, she hesitantly walked behind me and slowly unzipped the zipper. Letting the garment fall from my shoulders, I turned to face her as I stepped out of it. Wearing only a matching black panties, bra, and garter set, I took her by the hand and led her to the sofa.

"Now unhook my bra, sweetie," I whispered. Fumbling like a nervous school boy, Becky spent many awkward seconds trying to get it off. When she finally did, I turned around, clasped my hands around the small of her back, and pulled her back down to the sofa so that her chest was mashed against mine. Surprised by the sudden movement, Becky was not really sure what was happening as I reached up and kissed her. Just as I felt her big nipples grinding into mine, she jumped up off of me.

"I really can't do this!" she said. "I'm not even gay!" She looked down at me as if to ask me if it was alright for her to go. I only smiled and off-handedly rolled one of my nipples back and forth between my fingers.

"I'm just gonna go now...okay?" she said. She turned to leave but hesitated as I stood up and put my hand on her shoulder. Moving closer to her, I clasped my hands over her flat belly, pressed my tits against her back, and whispered into her ear. "I'm gonna fuck you now, Becky."

She inhaled as she felt the hot air of my breath on her ear, and I slid one of my hands into her little blue undies. Instictively tyring to avoind the touch of my fingers, she pressed her tiny ass back against my thighs as I cupped her pubic mound. I could feel that she was very hairy for a girl her age as I worked my fingers around, gently opening her swollen lips.

"Please stop Miss Andrews..." she said, but her body betrayed her as she slowly ground her hips into my hand. With my other hand, I pulled her undies down around her knees, but I could not get them any further without taking my hand away from her pussy. Her wetness soon soaked my hand and her pubic hair alike. Bemused, I giggled, thinking back to how wet I used to get when I was eighteen.

Confident that her protests were over, I withdrew my sopping hand and guided her into having a seat on the sofa. Kneeling between the young girls legs, I slid her undies completely off and motioned for her to lie back.

"What are you going to do Miss Andrews?" she moaned.

"I told you already," I said. She smiled, and I bent my head to her swollen cunt. Slowly sliding my forefinger into her pussy and my middle finger up her asshole, I clamped my mouth over top of her clitoris and started to suck. Within seconds she was in orgasm, rocking her hips back and forth wildly, and smearing her virginal wetness all over my face. "Oh fuck! Oh fuck!" she screamed as she squeezed my head between her legs. She had come three or four times, but I continued to apply my hold on her nether regions. The orgasms swept through the young girl's body one after another like waves on a beach.

When I finally released her, her chest was still heaving. I stood up and marveled at her spent little figure. She did not even see me take off my black panties as she lay there hugging herself in a little ball. When she had recovered a little more, she jumped up and hugged me. I kissed her again, but this time her tounge met mine as our lips pressed together. "Oh, what can I do to thank you, Miss Andrews?" the estatic girl whispered.

"It's funny that you ask, sweetie," I said as I twirled around and sat down on the sofa with my legs spread as wide as hers had been a minute ago. As the young girl nervously stared at my neatly trimmed pussy, I smiled up at her and said, "You'll have to stay and eat!"

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