tagLesbian SexFalling in Love with my Best Friend

Falling in Love with my Best Friend

bysilkstockingslover©

Summary: Straight girl begins to question her sexuality.

Note 1: This is dedicated to HOLLY who requested the true love story be told.

Note 2: This is a Valentine's Day 2015 Contest story do please vote.

Note 3: Thanks to Robert, Wayne and goamz86 for editing this tale.

Falling in Love with my Best Friend

Love...it comes when you least expect it.

At twenty-five and after a never ending fiasco of one failed relationship after another with men, I decided to swear off them for a while. I didn't realize at the time it meant forever, but that definitely ended up being the case.

My life at the time I met Janie probably was pretty mundane in retrospect. I was finishing off school, I went out with friends to dance, went to the gym, and took photos of everything.

Everyone has addictions. Mine are photography and shoes. When I'm depressed I go shoe shopping; when I'm happy I go shoe shopping; when I'm bored I go shoe shopping. I have over 50 pairs of shoes and heels in my closet...many I never have the right occasion to wear.

I also love nature. When I'm stressed, I put on my hiking boots and go for a long hike. There is nothing better for putting life into perspective than being one with nature. Away from the noisy, overcrowded, pretentious city life, one can quickly remember what life is really about...something that is easy to forget when working in the deadline based, fast paced world of the city.

Mom always said the best way to a man's heart is through his stomach (though I've learned it's actually through his penis and a willingness to blow him every time he gets the urge, quite frankly...if you don't, some other skank will), and I have always been an amazing cook. I love to create new recipes and experiment.

I'm pretty average when it comes to women my age; I don't mean that in a negative way, just a matter of fact sort of way. I mean, I'm cute in a Sandra Bullock kind of way, but not model sexy like most young actresses nowadays. I'm 5'7, 149 pounds (and determined to never hit 150), 34B breasts (not too big, not too small), hazel eyes, brunette shoulder length hair, with nice toned legs, a firm ass and pretty toes.

Anyways, enough background about me. This is the story of how I accidentally became a lesbian and found the love of my life.

I was just finishing up my last semester towardsmy degree in Business Administration. I decided to look for a part time job, something to occupy my time, and found one as a hostess at a café named Coffee Palace.

It was close to home, and I immediately felt comfortable, particularly because of one of the baristas, Janie.

Now it wasn't like I fell in love with her the minute I met her, that is way too Hollywood chick flick. But there was an unexplainable, undeniable pull towards her. It could have been her warm personality, her charming smile or her laissez faire attitude towards life (she loved every day the way I tried but failed miserably to do).

She trained me, and the more we chatted, the more we realized we had a lot in common, even though she was 31 and had a young niece, Cindy, whom she had adopted when a crazy situation arose. We both loved shopping (although I suppose that's true for most woman), both loved working out and staying in shape, and we both loved nature.

While I was a shy woman, uncomfortable in front of large groups, she was a people person who easily mingled with all cliques of people. She was a social butterfly I was a wallflower...yet we became almost inseparable.

We went shopping together, we started working out together and I even took her to my secret place of solitude, something I had never done with anyone.

Over the next couple of months, I also babysat little Cindy on a few occasions when Janie needed a babysitter. I began to take any opportunity possible to spend time with Janie. I would almost always come over2 or 3 hours before she was planning to leave and we would talk and I noticed she was often giving me very flattering compliments. It felt like she was hitting on me, yet she would never go any further than compliments or squeezing my arm. I would giggle like a school girl. Loving the attention and hinting I wanted more...even though those feelings confused me greatly.

We got into a fun routine where she would model her dresses for me and ask me to pick the one that made her look sexy. After the first couple of times doing this, I noticed I was getting wet and thought 'can this be? Am I getting turned on by this?' But on those occasions, I quickly pushed the thought out of my head as silly and just a symptom of sexual withdrawal, with no man in my current life or on the near horizons.

Then came my birthday on April 17th. I have never been a big birthday person, so I thought Janie had no idea it was my birthday when she called me and pleaded I come over right away and babysit as something had come up and she needed to leave ASAP.

Of course, I agreed.

When I got there, Janie hollered, "Come up to my bedroom, Holly."

I had been in her room many times as already mentioned, helping her choose her outfits when she went out...Janie being an avid clubber, something I wasn't a big fan of. I had gone out with her a few times, but usually I would babysit instead and use the late evenings to study so this wasn't out of the ordinary.

I had seen Janie in only a bra and panties, sometimes pantyhose or thigh high stockings, but never completely naked...until now.

I walked into her bedroom and she was completely naked sitting on the edge of the bed putting on a second nylon stocking. As I looked closer, I noticed that besides being topless, she also wasn't wearing any panties.

She finished putting the stocking on, stood up, ran over and pulled me into a big hug as she greeted me all excited, "Happy birthday, Holly."

I got a full face of her boobs and suddenly I panicked. Although I definitely had feelings for her, the sudden intimate act, which wasn't overly intimate, just Janie being Janie, startled me and I pushed her away and darted from the room, stammering, "I-I-I'll be downstairs."

My mind was spinning as I sat downstairs. If I hadn't pushed her away, what might have happened? Why was my pussy suddenly tingling with desire? I definitely found Janie attractive, but coming from a very conservative home, being a lesbian was a definite no-no.

Janie came down the stairs dressed and apologized, "I'm so sorry, Holly. I thought I read the signs better. I wanted to give you a birthday to remember."

Flustered and uncomfortable talking about it, I said, "Please, I don't want to talk about it."


"Okay," Janie nodded, a look of hurt and guilt on her face. She went to the kitchen and returned with a wrapped present, "Here's your real present."

"Y-y-you didn't have to," I stammered.

"You've become my new best friend, Holly," she explained. "Although I'm a little annoyed you didn't tell me it was your birthday."

"How did you find out?" I asked.

"Facebook," she answered. "I saw your many birthday wishes from family."

"Oh," was all I could say.

"Why didn't you tell me?" She asked, as she handed me the gift.

"I hate to make a big deal about it," I answered.

"You're a big deal to me," Janie smiled.

I laughed, before asking, suddenly very curious, "Sooooo, what did you get me?"

"Open it and find out," she answered.

I unwrapped the box and was shocked to see a new camera. I gasped, "Janie, this is too much."

"Nonsense," she said, waving a hand. "The amount of free babysitting you do for me, I imagine I owe you a lot more than that. Plus, you can't put a price on friendship."

"Thank you," I said, tears beginning to stream down my eyes.

"Come get a non-naked hug," Janie smiled, her charming smile breaking down the brief awkwardness of earlier.

I learned that Cindy was actually staying overnight at Janie's mom's for the night, and tonight was my surprise birthday celebration.

Janie sent me upstairs to get into something a little more sexy than my t-shirt and jeans and then we headed out for a late dinner and even later movie.

All night, I couldn't believe how lucky I was to have her. I also began questioning whether I had made the right decision to push her away when that intimate moment occurred.

Was I bi?

I was definitely curious.

Could I have a sexual relationship with another woman?

What would happen if it didn't go well? I couldn't fathom Janie not in my life anymore.

What would my parents say if I brought a woman home?

Yet, I was never happier than when I was with Janie. That was definitely true.

Over the next month, Janie never brought up that day and stopped flirting with me completely. There is that saying 'you don't know what you've got until it's gone' and that was definitely true in this case. I missed Janie's teasing sexual innuendo, I missed her gentle touches. I continually replayed that brief moment when her naked body touched me and almost nightly my bedtime routine included masturbating to that moment but with a much different ending.

My feelings confusing me, I went online. I did some research and eventually ended up finding a site called Literotica. I began reading lesbian stories and found myself imagining me being the protagonist in many of them. I came across an author, silkstockingslover, and after reading a few of her stories and getting turned on majorly, I came across a story called 'Bedding the Babysitter'. That story and its many sequels changed my life.

I imagined I was the young babysitter, Jenny, and that Megan, the seductress of the story, was Janie. I couldn't stop pleasuring myself and frantically fingered my fevered cunt until all my pent up sexual frustration exploded out of me when I reached orgasm.

I kept reading and reading the entire story series and wishing that was me and Janie; I realized that I was submissive through this story; I loved pleasing people in all aspects of my life including in the bedroom; I wanted Janie to dominate and make love to me as happened to Jenny by both Megan and, later, a cheerleader named Karen.

I came to grips that I likely was a lesbian, or at least leaning that way, as I no longer found guys attractive and I had been hit on many times while working at the coffee shop as well at school while finishing up my degree. I wanted to be with Janie, but I wasn't sure how to say so after I had rejected her so harshly.

I emailed silkstockingslover to thank her for the great stories, especially 'Bedding the Babysitter' and we began an online friendship. I won't get into the many emails we shared, but I told her my predicament and asked for advice. Being the kind-hearted woman she was, she gave me advice and I decided to make a move.

But first I received my degree and started a new job working as a secretary and thus had to quit working at the coffee place, making it more challenging to follow silkstockingslover's suggestions.

Determined to show Janie how I felt, I decided to make my move.

I asked her to meet for supper and she said sure.

We met at The Southside Diner and once we ordered I said, "I need to tell you something."

I was incredibly nervous and my heart felt like it might beat out of my chest.

She could tell something was up as she asked, "Are you okay?"

I took a deep breath and blurted, "I'm sorry about my birthday. I have regretted it ever since. I don't know why I pushed you away, as I am pretty sure I am in love with you. I wish I could turn back time and redo that event. Can we, can we have a redo?"

As I looked into her eyes, I saw tears forming and before I could say anything else she excused herself and hurried to the washroom.

I watched her walk away, my heart sinking into my stomach as I realized I had probably just fucked up our friendship.

I decided I needed an answer and needed to apologize for putting her in such a situation. I walked into the washroom and saw her standing in front of the mirror wiping tears from her face. I asked, trying to be a friend and not a lover to be, "Is everything okay?"

She turned around, smiled, walked to me and pulled me into a hug before kissing me.

My whole body became jelly from her touch and I knew, without a doubt, all my insecurities and questions about my sexuality were answered, as this was the best feeling I had ever felt.

When she broke the kiss, I started babbling. "I'm such a noodle head for not embracing my feelings for you. I just couldn't understand my own feelings and was overwhelmed and confused."

"I love you," she interrupted my babbling.

I felt like the luckiest girl in the world when I heard those words said to me.

I stammered back, in utter awe of the situation, "I-I-I love you too."

After another kiss, the washroom door opened and we made our way back to the table. We finished eating in silence, both our heads spinning with our new revelation.

Once dinner was done, I went to pay and when I returned we headed to the parking lot, each of us having brought our own cars. She said, as we stood in front of my car, "I have to go home, I only have a babysitter until nine, but we need to continue this conversation."

"I couldn't agree more," I nodded, wanting to feel her lips on mine again.

She leaned forward and kissed me. To my surprise, this time there was a very unique taste on her lips. When she broke the kiss, she smiled, "Just a slight sampling until we can be more intimate."

I looked at her confused, not really understanding what she was saying.

She smiled, "You really are an innocent lesbian virgin, aren't you?"

"But I'm a quick learner," I retorted.

"An eager beaver?" She questioned, raising her eyebrow.

"The eagerest," I replied, not even sure that was a word.

"Do you know why I always wear skirts?" She asked.

"To showcase your amazing legs," I answered.

"Well, that too, obviously," she nodded, before glancing around before moving her hand under her skirt.

I watched in awe as she apparently fingered herself.

Pulling her finger back out, she moved it to my lips. I automatically opened them, now realizing what I had tasted on her lips as she explained, "For easy access to my pussy."

I actually moaned on her finger from the naughty implication, the sample taste adding another piece of evidence that I was definitely a lesbian. I sucked on her finger like it was a cock until she pulled out and nodded, "Oh, I think you will be a very eager beaver."

My face went beet red at how eager I was to please. I wanted to kiss her again, I wanted to suck on her breasts and now I wanted to taste her sweet nectar directly from the source.

"Soon, Holly, very, very soon," Janie promised, before kissing me again and leaving me standing there, my panties soaked.

A few agonizing days later, our work schedules just not matching up, we ended up at the movies to see Lucy, although truth be told I have no idea what happened in most of the movie.

We went to a night showing at 9:45 so there were only a few people in the theater with us. We sat in the back and for the trailers we seemed to be playing a game of teasing chess: our hands would brush against each other getting popcorn; I would glance at her slyly, I sensed her glancing at me; we grabbed for the coke we decided to share at the same time.

Once the movie started though, my desire to show her my interest, to hold her hand, took control and I took the risk of putting my hand on her nylon-clad leg.

She whispered, "About time," and grabbed my hand and moved it to her thigh where her stocking ended. She continued, "Thigh highs make for better access, too."

"So I see," I whispered back, giddy with excitement, no longer watching the movie as I imagined creating my own.

She continued moving my hand until it reached her rather damp panties. She whispered, "She how wet you've already made me."

I couldn't believe I was touching her pussy through her panties.

She offered, "Go ahead, Holly."

I briefly wondered if she meant for me to drop to my knees and move between her legs. Part of me wanted to, but the thought of getting caught in such a compromising position held me back from my carnal desires. Instead, I moved my finger inside her panties and began to tease her clit.

"God, yes," she moaned, which excited me. I continued exploring her pussy, wishing I could see what I was doing or could see clearly the look on her face. Yet, her whispered words were all the encouragement I needed. "That's it, Holly, slide a finger inside me, please, baby."

I needed no more encouragement. I quickly obliged her suggestion, sliding one finger deep inside her wetness. I finger-fucked her slowly, in awe of what I was doing to the woman I loved, in a movie theatre.

After a couple of minutes, she moaned, "Pull down your jeans, baby, I want to do you too."

My pussy on fire, I reluctantly pulled my finger out of her pussy and quickly unbuttoned my jeans and awkwardly tugged them down.

She whispered, "You should have worn a skirt, baby."

"I'll never make that mistake againnnnnnn," I replied, as her hand went directly to my panty-covered pussy.

As her hand moved underneath my soiled panties, she asked, "Did I get your panties this wet?"

"Always," I moaned and twitched, as her finger made direct contact with my swollen clit.

As she moved her finger up and down between my pussy lips, she suggested, "Let's finger fuck each other, baby."

"Kkkkkkkkk," I trembled, as her finger slipped slyly inside my heated pussy.

I awkwardly moved my hand back between her legs and slid my finger back in and we started a lengthy journey of teasing each other as the movie played. She returned her gaze to the movie and I did the same. My eyes watched the movie, yet my brain processed nothing. All I could think about was her finger in my pussy and my finger in hers. I wanted to make her come, I wanted her to make me come, yet I replicated her pacing...which was slow...teasing...mind numbingly teasing.


The pleasure was intense, constant, but just enough to create a lustful desire for eruption. Suddenly, Janie whispered, "I need to go to the washroom."

Before I could respond, she was gone. I sat there for about five minutes wondering if she simply had to go pee or if I had done something wrong. Being in a new type of relationship, especially one where I still didn't completely trust my own feelings, was confusing at times. Yet, in the heat of the moment, it had felt completely natural: touching her and being touched by her.

My own insecurities were running rampant when Janie returned, leaned in and whispered, "Sorry, but your fingers were driving me mad, I had to go and finish myself off so I didn't scream I was coming in the middle of the theatre."

"Oh, God," I said, both turned on and relieved. "I thought I had done something wrong."

"God, no, you did everything so fucking right," she purred, tugging on my ear with her lips.

My body quivered, my ear being one of my erogenous triggers.

"I also got you a little present," she whispered, her tongue teasing my ear.

"What?" I asked, barely able to speak even one word.

"Open your hand," she ordered.

I mindlessly obeyed, knowing I would do anything she asked me.

As she tugged on my ear, I felt something wet in my hand. She whispered, "This is how wet you made me, baby."

After one more tug, she moved back to her chair. I was holding her soiled panties in my hand. I instantly felt a gush in my own panties and stammered, standing up as I urgently tugged up my jeans, "I-I-I have to go."

I scurried out and went directly to the washroom. As soon as I got in the stall, I tugged my jeans down and began frantically rubbing myself. Getting close, I pulled her wet panties out of my jean pocket and put them to my nose, wanting to smell her scent. That was all it took and my orgasm rushed out of me as I screamed, "Fuuuuuuck," not caring if anyone else was in the washroom.

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