My Journey through my First Lesbian Experience. Upper classman shows me the ropes

Prologue:

As an erotica author, I love telling tales of lesbian romance, especially from the perspective of a straight woman. It has always been a fantasy of mine, probably because it felt so wrong. But the longer I went on, thinking it was a taboo to have these fantasies, the more my appetite for this experience grew.

I wanted to take some time to talk about my journey. Not only did I begin writing erotica to fulfill some of these fantasies, I also had some experiences in the past that led me to become so passionate about it. But those, just like my erotica career, have mostly been a secret in my life. This is my opportunity to not only get these cravings off my chest, but to also talk about the experiences I actually got ot have.

I guess it all started a long time ago. I’m not a lesbian; I hardly even consider myself bi. But as I was growing up, I guess the idea of being with another woman always intrigued me.

Everyone always asks me, “Are you more like Jane? Are you more like Sarah? How about Linda?” I wouldn’t say I’m totally like any of those characters. However, I think several of my characters, and several of the stories, have parts of me in them.

Sarah sort of embodies how I viewed myself when I was younger. I guess I thought I would grow up a bit more like her, but though we do share some similarities, there are some things I definitely relate more to with Jane.

Like Sarah, I grew up naturally good at a lot of things. I was very fortunate to have parents who took really good care of me. They put me in a lot of sports and extracurricular activities, and I did pretty well for the most part. Unfortunately, I just never took too much of an interest in any of it.

For example, I played softball growing up. I never even cared for it, but I was always naturally pretty good. Unfortunately, I’m left handed, so when I got to high school, the softball coach said he didn’t want me playing second or third base like I grew up playing. Instead of moving to the outfield to play varsity, I just decided to quit lol.

I have about a hundred examples like that. It’s not that I’m a quitter… well, I guess I am in this case… but it’s just that I get bored with things pretty easily. And I guess you can say that happens in my relationships, too.

Nobody really knows I’m into women. At least nobody close to me. I’ve only ever seriously dated guys. But unfortunately, I can get tired of them pretty easily. And much like with softball, if one thing goes wrong, it’s not that big of a deal if I lose him.

It might sound harsh, but I’m still pretty young. There’s no need for me to settle when I’m still several years away from thirty. However, I’m not the one-night stand type girl either… at least not with men…

With a guy, I want a serious relationship. I want someone I could see myself with in the future who will help me raise healthy and well taken care of kids. But with women on the other hand… it’s a different story…

I don’t know why, but I just started fantasizing about women one day. I guess it started out like the premise of a lot of my stories. There were girls that I didn’t like for one reason or another, but I doubt they even knew it. I’m sure there were girls that didn’t like me, but I never had any type of rivalries or fights.

The girls I didn’t like were either entitled or just stupid… Okay, the more I write about this, the more I realize I am sounding like Sarah. I guess I sort of pondered what it would be like if my disdain for them went beyond my personal thoughts… and I figured I’d humiliate them pretty easily.

Spanking was never a deep fetish of mine until I saw it on some random TV show. I suppose I somehow correlated it to humiliating one of the opponents I had created in my mind. My thinking went something like, “Their parents obviously never spanked them, but what if I did?” Just the idea of humiliating them so badly was funny in my mind at first. However, the idea became more intriguing as I continued to think about it.

Being the deep thinking woman I am, I started to explore the phenomena. Only then did I realize it was a huge fetish in erotica and in porn. And as I explored it further, it began to turn me on.

Trust me, I was in denial for a long time. I hated the idea of these girls I didn’t like having anything to do with my arousal. I guess over time, I somehow justified it by thinking I was just turning myself on if I fantasized about spanking one of these bitchy girls.

I had ways of justifying it all… until I started thinking about these girls spanking and humiliating me… That was a twist in the story I just wasn’t ready for, but the more I thought about one of these little entitled brats spanking me, the more I realized there was no denying my arousal to these other women.

You would think this was backwards, but with men I like to have a connection and I want to be treated well. With women, on the other hand, there is just something so erotic about being intimate with someone I dislike. That’s a level of vulnerability matched by only very few things in the world. I’m getting hot just thinking about it…

Now, to sidetrack a little… One of my other talents that I didn’t care for was… you guessed it… writing! We had a big project my senior year, where we were supposed to come up with five different poems. I spent about thirty minutes total on the entire project and blew the class away when I had to read one out loud. They kept asking for more, so I ended up reading all five of them.

The teacher explained to me that professional writers take months to come up with stuff like that and encouraged me to explore writing and poetry further. I started to create a portfolio, but eventually… I got bored with it. Just like I didn’t care for softball, just like I didn’t care for prom, just like I didn’t care for piano, just like I didn’t care for soccer, just like I didn’t care for yada yada… I didn’t care to explore writing any further.

Back to the point… Although there was no real beef between these girls I didn’t like and myself, I just assumed they didn’t like me either. However, as graduation approached, several of them were very nice to me before splitting ways forever. Some brought up my athletics, others brought up my poetry that I guess impressed them so much… Some of them even said they admired my self-confidence, which is funny because I’ve never been confident…

It was an interesting moment in my life. For one, it made me realize that others may see me differently than I see myself. It also made me wonder how different my life could have been if I had at least tried to entertain friendship with some of these girls I disliked. Most importantly, deep down inside, I secretly wanted to ask them, “Would you ever be interested in a one-night stand?” Of course, I never asked them… but it was these interactions, along with their interest in my writing, that brought these two wonderful worlds together.

Chapter 1. Shante

When I was in high school, I wasn’t really friends with any of the girls who were into other girls. There were some around, but we just happened to be in different circles. I did have a few gay guy friends, but I didn’t feel like I related to them in this manner.

It wasn’t until college that I started getting to know bisexual and lesbian women. There was a girl in my circle named Shante who was a lesbian. She was a short and pretty, with milk chocolate skin and a hot little body.

This is where I relate to McKayla a little. Because I’m athletic, I happened to get recruited to intramural teams for a lot of different sports. They explained to me that having athletic girls is a big help. Like McKayla, they never expected much out of me and always told me exactly what to do. It was the others who did most of the work, including Shante.

She was a badass at flag football basketball. Unlike me, she wasn’t just athletic; she was actually really skilled at those two sports.

Although we were in the same circle of friends, we weren’t actually all that close. But since she was my closest lesbian friend, I started going to her with my questions.

One day, when we just happened to be alone, I asked her if she minded having a personal conversation. I could tell she was confused, but she gave me the green light.

I basically went through a series of questions, asking her what it’s like to be with another woman. Although she really didn’t know how to answer, she immediately snipped out that I was interested in other girls.

We had a long back and forth, I won’t bore you with details, but I eventually asked her, “Have you ever been with a straight girl?”

Shante assured me it was completely normal for straight girls to want to experiment. But then she caught my eye with, “I’ve had sex with plenty of straight girls.”

We pretty much left the conversation off there. I was trying to be respectful, and so was she. However, I must have made some kind of facial expression when she told me about her casual sex with straight women, because she brought it up over text.

It eventually turned into, “What’s going on? You’re obviously interested in hooking up with a girl.”

I was left chuckling because I knew that, “What’s going on?” really meant, “Are you interested?”

Although I liked the way she could read me, I wasn’t ready for that type of endeavor. To that point, I had only been intimate with actual boyfriends and committed relationships. However, throughout this whole process of talking to Shante, she convinced me that having a friends-with-benefits situation wasn’t the worst thing in the world. She also assured she would keep my secret, like she had done with other straight girls in the past.

One night, everything finally came to a head. After getting done hanging out with some friends, she nudged me on the side and asked, “So, what are you doing after this?”

I looked at her pretty face and shrugged my shoulders before nervously responding, “I don’t know.”

“Why don’t you come over to my apartment?” she asked, giving me another nudge.

My heart started to race as I pondered the possibilities. I smiled and said, “What did you have in mind?”

“Maybe I can answer some more of your questions.”

I followed Shante to her apartment, where we sat on the couch together. Even though the scene was set, and we had been talking about the possibility for weeks, it never really occurred to me that I was about to have sex with a girl, until it happened…

As the TV played in the background, she scooted closer to me and asked, “Well, now that you have me in person, do you have any questions for me?”

I pussy-footed around a bit until I eventually asked, “What is it like to kiss another girl?”

Shante laughed at me as if I was stupid. However, she was such a down-to-earth girl, she knew I was just nervous. “It’s pretty much like kissing a guy… Why don’t I show you?”

My heart raced as I realized my first lesbian experience was about to really happen. As nervous as I was, I tried to justify it to myself by saying it was only a kiss.

Unlike what she described, it was actually a bit different from kissing a guy. The pace was different, the smell was sweeter, I could even feel a different wave of emotions emitting from her feminine body. We kept kissing for a while because I wasn’t just exploring her mouth; I was exploring all the new sensations that came with kissing a woman.

To be honest, I would have been happy just doing that all night. The making-out within itself was so intriguing, my brain was going into overdrive already. But of course, Shante was ready to give me more, and I couldn’t deny this experience with the little hottie.

As the kissing got steamier, she started to climb on top of me. I was now lying on my back with Shante straddling my petite body. But although I’m pretty small, I found it really hot to have someone even smaller crawling on top of me.

Even though I don’t have a dick, I knew Shante was getting gratification from grinding on top of me. The way she worked her hot little body back and forth while she let out subtle moans into my mouth got me oddly jealous and aroused at the same time. It made me realize how good she was in bed compared to me, but it also made me discover the addicting satisfaction of knowing I can bring pleasure another woman.

She took her shorts off, leaving me gasping at her red panties with lace trim. After hearing a subtle moan making its way through my lips, she looked at me with a smile and asked, “Do you like something you see?”

Red in the face, almost matching her underwear, I admitted, “When I fantasize about women, they are often wearing red panties.”

She looked at me and winked before saying, “Well, I have a surprise for you,” before taking off her top and revealing a matching bra.

Although she looked sexy in the red bra, it was the fact that it was a matching set that really intrigued me. A woman wearing a matching bra and panty set is usually a good sign that they were expecting sex… and I really like the idea that she was so ready to fuck me that night.

Obviously, I wasn’t expecting to have sex at night, and that was apparent when Shante stripped me down to my tan bra and my deep navy panties. Either way, she seemed impressed enough by my body from the way she was licking her lips. She just couldn’t wait to climb back on top of me and grind her pussy against my torso.

I guess seeing her reaction boosted my confidence. Despite being the rookie in this lesbian experience, I was ready to take control. Without hesitation, I placed both of my hands on her voluptuous bottoms as our lips reconnected. The harder she moaned into my mouth, the more confident I felt, moving my hands up and down her little body.

Eventually, she moved down and positioned herself between my legs. Looking up at me with her pretty brown eyes, she said, “I got what I wanted; now it’s your turn.” She then pulled my panties down slowly as she whispered, “Do you like having your pussy licked?”

With a finger in my mouth, I nodded my head as I trembled in anticipation. After experiencing what she could do with her tongue during our kissing, I could only imagine what she would do with my clit.

Of course, she did an amazing job, licking my already soaking clit relentlessly while I drooled from the pleasure. It was probably the first time I felt someone enjoyed eating me out, instead of doing it for some type of return.

Shante started out slowly, and with soft little strokes. As my body got used to the tingling sensation, she increased her rhythm, licking faster and faster. Eventually, we got to a point for my head was leaned all the way back, with my eyes rolling even further. My hands were pinching my own nipples for some reason, and I was probably squeezing the life of her head. However, no matter how hard I squeezed, she was strong enough to keep my legs spread open as she continued to munch.

I’m one of those girls that usually takes forever to achieve my climax. As a matter of fact, I almost don’t even mind not having an orgasm during sex, because all the pleasure I get beforehand is just as important. But as long as it took for me to cum, Shante didn’t seem to mind. She never seemed to mind, actually. She just continued licking me out, eating my pussy until I begged her to stop.

The first time Shante made me cum, my quivering voice echoed throughout her entire apartment. I almost forgot that she shared walls with her neighbors. I could only hope nobody heard my whaling squeals from the relentless pleasure she gave me.

When she was finally finished with me, she looked up and giggled before crawling closer to my face. I wrapped my arms and legs around her, thanking her with my vulnerable body.

I guess she expected me to be done after having my orgasm. It was my first time with a woman and all, so this was her version of taking it slow. However, I wasn’t done with my first night of exploring my lesbian fantasies.

I began kissing Shante again, surprising her with my intruding tongue. She expected me to eventually settle down, but I was just getting started. Lusting over her panties, I pulled her beside me before I began rubbing her pussy through her underwear. There was no denying how wet she was after providing me my first ever lesbian orgasm.

Her eyes lit up as I rubbed her entire crotch up and down with my soft little palm. I guess she didn’t expect me to take so much initiative during my first time. Eventually, after we took turns taking each other’s bras off, I let my hand slide underneath her underwear as I slowly teased her clit. I was already addicted to her moaning for me, but now that I saw her body squirting at the touch of my fingertips, I felt a sense of power I had longed for ever since I started fantasizing about women.

I could have eaten her out, like I did several times in the future, but I badly wanted to make her cream those sexy red panties that I loved so much. I decided to keep my hand underneath her lace underwear and play with her wet pussy as I watched her tight body yearn for me.

At this point in my life, I had just barely started masturbating, so I wasn’t the most confident about stimulating a clitoris when I wasn’t even that experienced with my own. But despite being a rookie, Shante stroked my ego with her heavy moaning while I stroked her pussy with my soft little fingers.

Eventually, I had her moaning so hard, she couldn’t even kiss me if she wanted to. I was left watching her hot little body squirm around for me as my fingers slid up and down the wet lips between her legs.

As I started to focus on her little bean, her moaning and squirming only intensified. I eventually settled on a nice little circular motion, pushing her clit around as she crumbled to my fingertips. Unable to lay a kiss on her lips like I wanted, I began kissing little parts of her body. Her favorites were her neck and her nipples, and she definitely didn’t mind when I kissed her little shoulders, either.

With this being my first time exploring another woman’s body, I didn’t have any expectations of providing her with a climax. However, before I knew it, she let out one final thrusting exhale before grabbing on to me tightly. Then her eyes rolled back for a second before kissing me.

“Are you okay?” I asked, almost thinking I hurt her for some reason.

“I’m good,” Shante responded with a giggle. Then, resting your head back against the bed, she continued, “I’m really good…”

My lack of confidence came rushing back in, making me think there was no way I actually gave her an orgasm. But as I asked what happened, she answered, “You got me…”

“I got you? Like I gave you a…”

“Yeah… You made me cum.”

After that moment, Shante could hardly keep her eyes open after that. She tried to apologize for having trouble staying awake, but I loved the idea of putting her to sleep with all the pleasure I was able to provide. It was my first ever experience, but my appetite was only growing.

To be continued…