Her Friend

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Babysitting never paid like this.
1.7k words
4.48
64.2k
3
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Part 1 of the 2 part series

Updated 11/01/2022
Created 10/06/2005
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Terri was my fiancé's best friend. She had been there through thick and thing for Dana a number of times. Then Dana met me and we hit it off. Terri was 19 and had a one year old baby girl, Kaylee, who was just the most charming baby you could ever want to meet. So from time to time I would baby-sit for her and all I needed was a hug from her to make it all worth it. My fiancé was no slouch, she was attractive and intelligent, but she was not Terri.

Terri was your Playboy Magazine picture perfect girl next door. She could not help it she was a knockout. She had auburn hair that came just past her shoulders. Her green eyes could hypnotize you in an instant. Her skin was soft and like a fleece blanket. She was athletic in build but not muscular. Her breasts were pert and firm but not overly large. Her bum was firm and rounded nicely. The most alluring thing about her is she acted shy and had a way of flirting with you so that you wouldn't really think it was a flirt.

I was babysitting for her one evening because she was going out on the town with my fiancé. I came over a little early so that she could get dressed to go dancing at the club without worrying about Kaylee. She was in a bathrobe when I arrived and she greeted me at the door. I asked how she could be so gorgeous just out of the shower and she blushed slightly and smiled so her dimple showed on her right cheek. She walked back into the bedroom and I sat down and started played with Kaylee making her giggle in that silly little baby laugh that always gets you right in the heart. I looked up to see Terri standing in the doorway to her bedroom smiling at me. I stared and must have embarrassed her because she realized she was standing there in her white lace underwear and thigh highs and went back in the bed room.

Terri returned to the living room area where Kaylee and I were making noise with one of her dozen or so toys. She had a tight white top on and a jean skirt that barely covered the thigh highs. I was beside myself with how beautiful she looked and I told her she looked quite attractive this evening. She smiled shyly and thanked me. Just then there was a knock at the door. My fiancé had finally arrived; she was dressed to kill as well. She was wearing one of her low cut shirts that accentuated her large breasts. I told the ladies to have fun and I would see them later.

They returned later that night to find both Kaylee and me asleep. I had crashed on the floor next to Kaylee's crib and hadn't noticed they were there until a few minutes later. My fiancé saw me laying there and had told Terri to let me sleep and send me home in the morning. They were both quite intoxicated and trying to be quiet but were not doing that well. Dana left and Terri had put down her purse making her way to the bedroom. A few minutes later she walked back to the kitchen and was taking a few Tylenol with a glass of water. She was wearing a long t-shirt and it seemed like nothing else.

She eventually made her way over to the door of Kaylee's bedroom and watched both Kaylee and I sleeping for a few minutes. The bedroom light was behind her and I saw her shapely silhouette under the t-shirt. She moved into the room and had kissed Kaylee and then surprisingly she pulled the blanket up on me and left a lingering kiss on my cheek. The smell of her perfume filled my nose and made me tingle all over. I pretended to sleep and rustled slightly but didn't make like I was waking. She left the room and I fell asleep with the vision of an angel in my mind.

About an hour later I awoke to the smell of her perfume entrancing my mind. Sometime while I was sleeping she had came back in the room and crawled under the blanket with me on the floor. Her warm soft skin was against me and the thought of her here made me stir in my sweatpants. I made as if I were changing positions in my sleep and rolled off my side onto my back. She rolled onto her side at the same time and rested her arm over me and had placed her head in the nook of my shoulder and neck.

Her breathing was warm on my neck and was making me crazy. I was becoming slightly hard and I know my breathing changed. My hand came to rest along my side and now she had rolled onto it. My hand was now resting against her hip and I could feel that she was sans panties and also sans pubic hair. Now I know my breathing changed.

She leaned in against me and whispered in my ear, "This is just between you and me." She slid her hand down the front of my chest and stomach and rubbed my growing erection with her hand.

"Mmmm, Dana always said you were thick but I could not have imagined in all the times I fantasized about you that you were this thick." She said.

I was surprised at what she said and replied, "Fantasized about me?" She just nodded.

She pulled my cock out the front of the boxers and was stroking it playfully. She moved in and nibbled on my ear and that drives me wild. I turned my head and kissed her. Her lips were soft and she still had a little taste of the booze on her tongue. I asked her if she was sure about this and she answered, "Completely."

She kissed her way down my chest, stopping at my nipples. She sucked and nibbled on each one in turn. I wanted to moan but had to remain quiet. Sensing this she grabbed me by the hand and guided me to her bedroom. She slipped off the t-shirt and then pulled of my sweats and boxers. She was so beautiful naked, I was mesmerized by her. She pulled me onto the bed and kissed me hard. Her naked skin felt like soft velvet. She went back to nibbling on my nipples and I moaned. She kissed and licks made their way down my belly to my now raging hard on.

As she slowly took my cock in her mouth it felt as if I were being bathed in warm water. I looked down to watch her head as she slipped me in and out of her mouth. She looked up every so often and watched me watch her. She pulled her head off my swollen member and licked her way down to my balls. She sucked each one in turn and bobbed them about on her tongue. I gasped when she reached down and slipped her fingers into her now dripping pussy and got them covered in her juices. Instead of playing with herself she licked all but her middle finger. To my surprise she gently slipped this one into my ass and then started to suck my cock again. She pressed her finger against the inside of my ass and rubbed a certain spot. It seemed like only a few seconds and I was shooting jet after jet of hot cum down her throat.

She coyly looked at me and said, "I see you liked that.", and I just nodded.

A few moments later she was straddling my chest and looked down at me and ordered me to lick her till she came. In a quick move she had made herself kneel over my face. I worked my tongue on her clit and her lips. I slid my tongue in and out of her wet opening and soon she was moaning and rocking her hips against my face. I looked up to see her pulling on her nipples and I grabbed her hips. I pulled her down against my face and sucked and nibbled hard on her clit. She whimpered as she came.

Then in almost in a gymnastic move she spun around to face away from me and squatted over my cock. She lowered herself onto me and I felt the warmth of her sugar walls engulf me. She kneeled and began to rock back and forth on my cock. She felt incredible riding me and milking my cock with the muscles inside her. I sat up against the headboard and caressed her back. She leaned back towards me and looked over her shoulder with a look that said make me faint.

I reached up grabbing a handful of hair and she groaned out, "Oh yeah, that's the way!" She rocked harder against me and was now pulling on her nipples. She begged, "Spank me, and don't be gentle." I fulfilled her request and she moaned every time my hand met her cheeks. Before long she was gasping for breath and moaned with an orgasm that made her shudder.

She took some of the juices from her hard orgasm and tasted them. Licking each finger one by one she smiled at me with gleeful pleasure. "Stroke yourself off!" exclaimed this shy girl who had become a harlot in just an hour. I started to stroke my cock and she watched tentatively. I felt myself closing in on an orgasm. She whispered to me, "Cum on my tits." This exclamation brought me to orgasm and my cock began to shoot out cum again. She excitedly rubbed it into her skin on her breasts and then kissed me.

She rested back down on the bed and we cuddled our way to sleep. In the morning she joined me in the shower and we had another session with me fucking her standing up against the wall. She reiterated that this was between her and me.

I looked at her and said, "As if I would share this!"

Her reply was" No, but maybe we can share Dana sometime."

I smiled as I walked out the front door. Now that was something to think about.

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don87654don87654over 18 years ago
Intriguing--And Only Natural

Very erotic. Another one of these stories where the woman is obviously ovulating and wanting reproduction of some kind. That you are babysitting, perhaps she wants to have another baby so you can continue babysitting for her and maybe become more? This story could use some more chapters along that line.

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