• Posted on May 1, 2019 at 2:08 pm

by Amanda

{ This story was originally posted at Lesbian Lolita in September 2005}

I was ten the first time I ever had sex with a woman. I’ve been with one man since that and it was enough for me to know that I am definitely gay. Her name was Emily. She was a seventeen year old goddess, the prettiest girl in school. I lived in a small town back then, one where everyone knew everyone, and who everyone was sleeping with. Well, Em didn’t want to be labeled a slut, so she had found a different way to satiate her desires.

I worshiped her. She and my sister were both cheerleaders. I would watch them practice for hours, bringing them sodas or fetching towels. I was really doing it for Em, but Maddy, my sister, was there so I had to play nice for her too or she’d run me off.

To this day I suspect that Maddy and Emily had some kind of sexual history, but it had to have ended when my sister started sleeping with her boyfriend. I think this is what had Em back on the prowl.

I was a dead ringer for my sister, only in a younger package. She and I both had my mother’s looks, her dark hair and blue eyes. Maddy had lovely 34 C breasts and I had just started to show the slightest puffiness around my nipples. Maybe that’s why Em liked me. She did like me, she talked to me like I was her age, and she hugged me a lot. She had started babysitting me sometimes when she was thirteen, and we were close.

Maddy was taking a shower after one of their practice sessions and I was sitting outside, listening to Em talk. I can’t remember what she was saying, only that I loved her soft voice and southern drawl. I loved to look at her. I didn’t understand my fascination with her and her beauty back then, but I know now I had a massive crush on this girl.

I noticed, as I sat fawning over her, that Em had become quiet. She was sitting in front of me smiling. “Do you like any boys in your school?” she asked me.

I just shook my head, too mesmerized by her to speak. She reached out and poked my belly and I laughed, playfully pulling away from her.

“I’m going to Greg’s place, can you watch the munchkin till I get back?” Maddy asked, interrupting my moment with Emily. She was rubbing her hair with a towel as she stood wrapped in a robe and dripping in the doorway. She didn’t wait for an answer, just turned and went back in. She knew Em liked spending time with me and wouldn’t say no.

Maddy was gone in a few minutes, leaving me alone with the most fabulous woman on earth. My mother wouldn’t be home for hours — she worked evenings at a textile mill, and I knew Maddy would be at Greg’s until just a few minutes before Mom got back. It meant lots of time with Em, and that was never a bad thing.

Emily took a shower and got dressed while I sat watching television. She made us some frozen pizza for dinner and we sat watching television and eating.

“I should charge your sister for this, ya know?” Em said. I looked up at her.

“You don’t like staying with me?” I asked, a note of heartbreak in my voice.

“Of course I do, sweetie.” Em leaned down and hugged me. “But I make everyone pay for babysitting.”

It hurt me a little, knowing I was just a job, but I never thought in my wildest dreams that Emily liked me the way I liked her. Not that I fully understood those feelings anyhow.

We watched television for the rest of the night. About an hour before bedtime, I changed in to my pajamas and snuggled up on the couch next to Emily. We watched Remington Steele together and when it ended, I headed for bed.

I was most of the way up the stairs when Emily came hurrying up behind me and turned me, pushing my back against the wall. She put her hands on the wall on either side of my head and leaned in close, smiling. And those green eyes, they went right through me. I still have a thing for redheads because of her.

Emily didn’t say a word, just stood there smiling at me, making me nervous. I didn’t know what was going on, I couldn’t imagine why she would be doing this until she leaned in and pressed her mouth against mine.

My eyes opened wide but I could see she had closed hers. She parted her lips slightly and pinched my bottom lip between her own. I was in shock. The most beautiful woman in the world was here with me, kissing me. I didn’t know much at ten, I’d led a sheltered life, but I knew this was the kind of kiss only boyfriends and girlfriends gave each other.

It felt like forever, standing there with Emily’s flowery scent filling my nostrils and her warm, soft lips pressed against mine, before she broke away and stood back. She pressed her finger against my lips. “Don’t tell anyone I did that… okay, Cyn?” she whispered.

Don’t tell? I wanted to scream it from the rooftop. I was in heaven, dancing on clouds, swooning. But I knew enough to understand why I couldn’t say that an older girl like her had kissed me that way.

She walked me up to my room and tucked me in, stopping to kiss me once again on the lips. It was a shorter kiss, but just as heavenly.

If I’d known about masturbation then, I’d have had some way to relieve the aching desire I was feeling. My sex was hot and swollen and it felt a little wet. I didn’t understand what the kiss had done to me, but I liked the feeling. For all its frustration, I truly liked it.

The next time I saw Em was about a week later. I had begun to feel hurt that she hadn’t come around, especially after the beautiful kiss we had shared. I was walking home from school and she was getting off the bus from high school. She saw me and called out to me, then came running up, all smiles.

She was so sweet, she took my book bag and slung it over her shoulder. “Can I walk you home?” she asked.

What was I going to say? No? Of course not, my red-haired goddess was offering to join me — not come see Maddy, not just going the same way I was. Her house was actually in the opposite direction, and she was walking me home. I just blushed and smiled bashfully. She smiled back and took my hand walking me the two blocks to my house.

“Maddy went to the dentist today… she won’t be home ‘till later,” I told Emily as we walked into the house.

“I know sweetie, we have math together. But I wanted to see you.”

She came to see me! Me, not Maddy, not for practice, she came for me! Could anything be more wonderful?

Dutifully, like the good little girl I’d been taught to be, I went into the kitchen and poured a lemonade for both Em and myself. I brought them into the living room, handing the bigger of the two glasses to my lovely Emily. “It isn’t as sweet as normal,” I told her, sipping at mine.

Emily sipped her drink and set it aside. She patted her hand on the couch, inviting me to come sit with her. “I missed you this week,” she told me as I sat down next to her, feeling giddy from being so close.

I set my lemonade down and tried to look relaxed. I didn’t want to act like a little kid, I wanted her to like me. “How come you didn’t come by?” I asked her.

Emily just smiled that beautiful smile at me. She stroked my hair so softly, I could feel her touch all the way down my back. I leaned into her palm as she touched my face and closed my eyes.

I gasped when I felt her lips on mine. It surprised me but only for a moment and then I leaned into the kiss, letting my lips part as hers had. I was wearing a short skirt that day, and I hardly reacted when she began to touch my leg. Emily’s hand felt so soft and warm as she stroked my lower thigh. I could feel she was moving her hand higher, under the hem of my denim skirt. I was scared, I’ll admit it, I was very afraid — but it was Emily and I trusted her. She’d been watching me for about four years and I felt so at home, so safe with her.

Emily’s lips were gone from mine and I opened my eyes to that lovely smile. I swallowed hard and couldn’t keep my gaze from lowering to watch her hand disappearing under my skirt.

I startled when her thumb brushed across my clit and she paused, the smile never fading. “Is that okay, sweetie?” she asked me. Mom had told me that that was my special place and no one could touch it. She had said that I shouldn’t talk about it or touch it, because I had to be a good girl.

I was afraid, but it was Emily — how could she be doing anything wrong? Slowly I turned my head from side to side, wrapped in the moment and much too nervous to speak. “Does it feel good?” she asked as she pressed her thumb against my clit once more. I nodded my head slowly, eyes locked on her arm.

It did feel good. Every time she moved her thumb it sent waves of tingles through me. I’d never felt anything like it before. She was touching me in such a wonderful way. I could feel my breath quickening, and the room seemed to be getting hotter. “Won’t we get in trouble?” I finally managed to ask.

“No one has to know, sweetie. I won’t tell.” Emily sat back. She picked up her lemonade and sipped it, then set it back down. “If you want to stop, you should tell me,” she said quietly.

Want her to stop? For all the fear, the uncertainty, I was loving this. All this wonderful, naughty attention from my goddess, I had to be the luckiest girl in the world.

“But I’m a girl,” I told her. Like I said, a sheltered life. I didn’t understand my feelings for her, and knew nothing of lesbians or pedophiles.

“I like girls,” she said, almost blushing. “Especially pretty little blue-eyed girls like you.” She pressed her finger against my nose, tracing it down to my lips. She made a kissing smack with her lips and I giggled shyly.

Emily was incredibly gentle and kind. I remember teenage sex, it was rough, clumsy, selfish. Emily was none of these things with me. She made me feel like I was the only thing in the world to her. She was a wonderful girl.

Slowly Emily coaxed me up and led me to my bedroom where she eased me down on the bed. She straddled me, walking on her knees until she hovered over my hips, staring down at me. The smile, that constant smile, it never faded or faltered as she pulled her sweater up over her head and dropped it on to the bed next to me. Her scent wafted up to me when the sweater landed next to me and I drank in its scent. She smelled so soft and sweet.

I swallowed hard when she popped the buttons on her jeans. Em shifted on the bed until she could get her pants off and then there she was — fair skinned, light freckles, hovering over me in her white lace bra and panties. I know now, though I didn’t then, that she had planned this. She had worn the underwear for me, though I couldn’t fully appreciate it at that age.

With little bumps on my chest and no hips to speak of, I suddenly felt self conscious. Emily’s curves were so perfect, so beautiful, and me, I looked like a boy. Absently my hand went to her hip and I stroked her leg. She was so soft, it was like rubbing silk.

“It’s your turn,” she cooed as she began tugging at my shirt. I didn’t want to stop, but I was ashamed of my immature body. I resisted as she pulled my shirt off, but only a little and hardly enough for her to notice. Next came my skirt. She sat back and looked down at me, her eyes growing slightly larger.

I blushed and covered my breasts, tears rushing to my eyes. I was so embarrassed I didn’t know what to do. “I’m ugly.” I sobbed.

Immediately Emily fell on me and hugged me. “You’re anything but ugly, sweetheart,” She said, trying to comfort me. Finally she sat back and coaxed my hands away from my breasts. I was feeling better, she had a way of just making things okay.

“But I don’t have any boobs,” I whined, trying to cover my chest. “Maybe I’ll be pretty like Maddy when I grow up.”

“You’re beautiful now.”

“But I’m not…”

Emily pressed her finger over my lips. “Shhh…” she whispered. “I like you just like this.”

“And you d-don’t wish I was older?”

Emily shook her head and leaned down, kissing me. She then whispered in to my ear, “I think little girls are sexier.”

I didn’t understand what she meant. I wasn’t even sure what sexy really was. But it made me feel better all the same. I relaxed a little and let her win the battle for control of my hands.

Emily sat back up and reached between her breasts, unclasping her bra and letting it fall away. I’d never seen bare breasts before. Not Maddy’s, not my mother’s, no one. They were wonderful. Em’s breasts were beautiful round C cups with youthful pink nipples and a slight dusting of freckles. I wanted to touch them, but I was too afraid.

I didn’t have to wait or wonder. Emily took my hands in hers and guided them to her breasts, helping me massage them, touch them. She moved my thumbs over her nipples, and closed her eyes, sighing softly.

Slowly she moved my hands down her body, letting me feel every inch of her. Finally she reached her hips, and she pushed my thumbs under the elastic of her panties. She helped me pull the lovely lace panties down her legs and off.

Emily kept herself trimmed into a perfect orange red triangle of fine soft hair. I couldn’t tear my eyes from her sex. It was amazing. Her lips protruded slightly and I could just detect her musk in the air. She took my hand again and guided it towards her vulva. She pressed my finger against the hard knot hidden in her folds. I could feel her warmth and her wonderful wetness. It sent a charge through me.

“Do you feel that?” she asked. I nodded my head. “That’s called a clit. It’s where we girls feel something really special.”

I looked up at her, into those green eyes. I was trying to comprehend everything that was happening, trying to understand how I could be so lucky as to have her attention this way.

Emily’s hands on my body brought me back, and I closed my eyes. She was gently pinching my nipples and rubbing the soft flesh that would someday be my breasts. Slowly she moved her hands down my body until they were separated from my skin by the thin cotton of my panties. Em hooked her thumbs under my panties and slid them down my legs. Again I found myself feeling embarrassed by my immaturity, but her broadening smile reassured me.

The softness of Emily’s lips on my nipple sent waves of heat through me. She kissed my breasts, rubbed them, made love to them. I could feel the sweat on my forehead, and my breath was quickening so much that I felt a little dizzy.

Emily made her way down my belly, rubbing my sides, caressing me, loving me as she went. Finally she reached my sex and paused to look up at me. Our eyes met and I swallowed hard and tried to smile.

A shock raced through my belly when her tongue touched my clit. I gasped and clenched my fists. Emily suckled my clit, coaxing moans from my lips.

I don’t know which finger she used, but she didn’t break my hymen. The sensation of her finger sliding inside me, though, caused me to arch my back and gasp, almost squealing as I did. She lapped at my clit, suckled it, pinched it between her lips. I was writhing on the bed, my head thrashing from side to side.

My eyes flew open, but my vision dimmed as I felt my very first orgasm rip through my body. I shuddered, trembled, squealed. I felt my toes clench and my hands were tearing at the covers on the bed. “Em!” I squealed as she caused another wave of pleasure to race through me.

Finally spent, I relaxed into the bed and closed my eyes, breathing deeply, contentedly. My vagina was still spasming every so often. Each pulse carried a wave of pleasure with it causing me to drift just at the edge of sleep.

“That’s called a climax,” Em said as she slid up to lay next to me and kissed my ear. I opened my eyes and turned my head to look at her. I couldn’t yet speak. I was in shock. Nothing like that had ever happened before. I didn’t even know it could happen. She stroked my face, happy to let me lay there and recover from this brand new experience.

“Is that sex?” I finally managed to ask.

“Yes,” she answered simply.

That opened a door to a new world for me. Suddenly I doubted everything my mother had ever said about sex. It wasn’t dirty or bad, it was wonderful, soft, gentle. Emily had shown me something I could never have even dreamt of. Maybe my crush on her had been one of those normal little girl crushes on an older girl — but this, it had changed me. If I wasn’t gay before, I was now. She had ruined me for anything but females.

I was starting to gain coherence. Emily coaxed me up on to my knees and helped me straddle her. She guided my hands over her breasts. I pinched her nipples like she had done for me. I realized what she wanted from me and I wanted to do my best for her. I wanted to give her what she’d given me.

She moved my hands down to her belly, but I was feeling more confident and took over, rubbing, stroking, caressing her as I built up my courage to reach down and touch her sex.

My hands moved over her pubic hair and soft mound until at last they moved through her moist folds. Emily sighed, smiling up at me, encouraging me to continue. “Did you like what I did for you?” she asked me. I nodded my head, already able to see what she was getting at. I was nervous though, I wasn’t sure I could do it. “You remember when I showed you my clit?” Again I nodded my head. “When you lick that, and suck on it, it feels very good.”

Slowly, timidly I slid down until I was between her legs, staring at her sex. It was a beautiful sight. I traced its outline with my finger, fascinated by what I was seeing.

Finally, having built up the courage, I moved forward, stretching my tongue out. I pressed my tongue against her clit and moved it slightly. Again, she sighed. She began gently stroking my hair and whispering to me, but I couldn’t understand what she was saying.

The scent of her excitement, the taste of her honey, it excited me, sending new waves of desire through me. I loved her taste. No woman I’ve ever been with has tasted as sweet as she did. Maybe it was because she was my first, or because she truly was a goddess, but Emily was wonderful in every way, so much that even today I dream of her.

Feeling more confident I did as she had instructed before and sucked her clit into my mouth. I pressed my tongue against it, trying to remember what she had done for me. It was all a blur, though — and I wasn’t sure I was doing it right.

“Put your fingers in me,” I heard her say. I shifted on the bed and penetrated her. The feeling of her walls closing around my fingers triggered a new excitement. I felt the warmth in my lower regions again. I couldn’t believe how easily they slid in, how her body seemed to welcome me.

I moved my fingers in and out while I suckled her clit. Emily began rocking her hips with me, moaning more loudly. I relaxed a little as she ran her fingers through my hair. Even something so simple as that excited me.

“Oh!” she gasped. Emily drew me into her, trying to get me to put more pressure on her clit. “Suck harder!” she whispered hoarsely. I did, trying to do my best for her, trying to make her feel as wonderful as she had made me feel.

With a single cry she pulled me forward, arching her back. She moved her hips more slowly, pulling me in, begging silently for more. I was a little afraid, I couldn’t breathe, but didn’t want to stop. I felt her walls contracting around my fingers, and I made a single muffled sound, the vibrations of which sent shudders through her.

Finally she relaxed into the bed and quieted. I crawled up to lay next to her, staring at her in amazement. I had done it, I had given her that amazing feeling! I felt powerful, older.

Emily opened her eyes and rolled onto her side, smiling at me. “You’re really good at that,” she said to me. I blushed and averted my eyes. She leaned in and kissed me softly.

“Can I be your girlfriend? I promise I won’t tell,” I assured her, knowing already that what we had done must be a secret at all costs.

“I dunno, sweetie, are you sure you’d like that?”

“I want to be your girlfriend, and you can be mine,” I begged.

Emily turned me on my back and pulled me against her naked body. She kissed my neck and shoulders. I loved the way it felt to be held in her arms that way. “Okay sweetie, we’ll be girlfriends.”

I wanted to jump up and dance and sing and run around but I didn’t move. Having her hold me like that, it was too wonderful to run from, now so more than before since she was really mine, she was my girlfriend. “Can we hold hands when we watch TV?” I asked her.

Emily rolled up and kissed my cheek. She tickled my side playfully and squeezed me. “As much as you want, sweetheart.”

I can’t even begin to tell you what Em meant to my life. She was the most memorable lover, the most precious memory I have. She made my childhood a time of wonder and beauty, and I will be eternally grateful to her.


11 Comments on Emily

  1. kim says:

    What a wonderful story. Beautifully loving and erotic.

  2. David says:

    Wow, what a beautiful story! So erotic and well written and detailed. I have no idea who you are but I hope you write some more. Thanks

  3. Sapphmore says:

    Every time a story is posted with author unknown, I check my folder of stories I’ve saved from other sites such as Leslita/Loliwood etc in case I have it. Lo and behold, I have a copy of the original story (looks word for word) and it is by ‘Amanda’. There is an email address at the end but I won’t give it on the open site in case I’m not allowed.

    Jetboy, I’ll sent it to you direct.

    • JetBoy says:

      Thanks for the find, sir. I’ll fix the author credit right now.

      • Naughty Mommy says:

        Are we sure this isn’t the same ‘Amanda’ who wrote all these stories?

        • JetBoy says:

          Yes, it IS the same Amanda, damn it. I figured this out, only later than I would’ve liked. (I put on the dunce cap for a couple of hours as penance.)

          Sadly, this kind of thing will happen when we’re racing around like decapitated hens, seeking content for this site. Just a reminder of how hard we work to feed your boundless appetite for quality erotica, dear readers…

  4. Katejn90 says:

    Omg such a wonderful story, such innocence, so much tenderness

  5. kacey says:

    Beautiful ?

  6. Jack says:

    What a gorgeous story!! Thank you for bringing it to us, JetBoy! I hope “Another Amanda” writes again!

  7. Myka & Sophia says:

    So beautiful … we were so lucky that we both had beautiful ‘first time’ sex with loving mentors … so sad it is not always as it should be …

  8. Douglas says:

    Excellently written story, very sexy erotic. Any plans for a part 2?

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