Samantha's First Experience Pt. 01

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An unbelievable first time experience.
6.4k words
4.67
112.3k
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Part 1 of the 22 part series

Updated 06/10/2023
Created 10/29/2020
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My name is Samantha and I have a unique and non-believable lesbian story that I need to share with the world. The names have been changed and places omitted to protect privacy. I have to give a bit of a back story to get to the heart of them matter.

I had been home after graduating college at FSU for a few months in southeast Florida and was just about to start teaching at a local grade school in fall of 2002. During my summer home, I spent time with old friends, hanging at the beach, shopping and going out to the local bar scene and preparing for my first year as a new teacher. During that summer I met Wayne. Wayne was one of those tall dark and handsome men, like my father, who I adored my whole life. I met him at a local club one evening after my friends and I decided to go out for a drink. Wayne's softball league had just finished their game and had come to the bar to have a few drinks. Wayne was tall, thin, almost lanky, with big brown eyes and a small little mustache which fit his face oddly. But he had a great smile and was very friendly and seemed like a decent guy.

After a few dates with Wayne, I decided I was more interested in more than friendship with him, so we started a dating relationship. Things were going along smoothly as July turned to August and I was enjoying our developing relationship. I hadn't had much sexual experience expect 3 other long-term boyfriends prior to Wayne. My H.S. sweetheart waited forever for us to finally have sex. I was a scared little girl who was raised Christian and believed in faith and love not just quick and easy sexual intercourse. At one point even before I lost my virginity, my BF (at the time) and I tried anal sex. I kind of figured it would give him penetration he wanted and keep our relationship moving forward, but yet not give up my beliefs in waiting and being in love, knowing it was the right guy at the right time before finally giving up my virginity.

Before I even left for college, the boyfriend at the time and I had some good sexual experiences. But once college separated us as it does with a lot of H.S. lovers, I moved on. My third BF was a guy I met sophomore year of college, but the relationship ended mid-term senior year of college as he was heading back north for his internship and I would be heading just back home to Fort Lauderdale after graduation. Once I was back home and, in the groove, it was fabulous seeing family and old friends and starting a new chapter in my life, seemed things couldn't get much better. Or at least that's what I thought....

One evening Wayne asked me to come over and hang out at his place to watch some movies and order in take-out. I obliged and we were having a quite night when his doorbell rang. He got up to answer the door, I turned the TV down when I heard the voice of a woman. I could hear Wayne trying not to talk to loud, but yet be clear enough to tell her to go away. Being curious I got up and walked up behind him, to see him in the doorway speaking with a young female blonde girl. The situation between them was tense and Wayne was still trying to speak softly enough for me not to hear. Once the woman at the door saw me, she said, "I see why you don't want me here".

Wayne turned to look to see me standing behind him. My heart dropped. Was I the only woman in his life? Who was this?

Wayne said, "Samantha this is Jennifer."

I could see the tears welling up in Jennifer's eyes, her heart was breaking, as was mind. Wayne was in pure panic; he didn't know what to do. After some heated words, Jennifer told him to go fuck himself turned around and walked away. I asked Wayne, "Who was that?"

Wayne tried to play it off as an old girlfriend, a former lover, but I knew she was the other woman. Or maybe I was.

I walked back into the front room, grabbed my coat and purse and started to leave. Wayne begged me to stay but I didn't even want to deal with this situation. I didn't want to be the other woman, or know there was another woman besides me. What a joke I thought to myself. Wayne chased me all the way to his door apologizing and begging me to stay, but I knew better. I left Wayne's house that night very disappointed in love, in what experiences I had had and what a bad time this was for someone to jerk me around right as I'm about to start my new career. I thought to myself what a year this had been, I lost my college BF to his home up northeast, had no one special at my graduation, no lover until recently, only to find out that I was being rolled over by a softball playing douchebag...

I needed a drink, but didn't want to walk into a bar by myself. I wanted to call some of my friends, but after all who wants to be around a mopey, depressed, emotionally upset played over girl. I decided to stop and get some gas in my car, pick up some beer and just head to the beach. After I composed myself, I walked into the service station and was standing by the alcohol section, when I heard a woman's voice say, "Hello".

I turned to look and it was Jennifer. The girl from Wayne's house! Seemed she to needed a drink and by fate we ended up at the same gas station. I can tell she had been crying, as I am sure she could tell I had been to. Jennifer said, "I'm sorry we had to meet this way; I didn't realize he was seeing someone else."

I was angry, I was upset, I was hurting so I said, "Yah me too."

I grabbed a 12 pack and went to the counter. Full of attitude and hate I slammed the beer on the counter and was short with the clerk. As I walked out, my emotions got the better of me and I began to cry again. I couldn't drive in this condition, so I set the beer on top of my hood and just stood there with my head in my hands crying. Why me? Why this guy? Why her? What did she have that I didn't?

As I was standing there, Jennifer came back up to me, her car was on the opposite side of the gas pump. She said to me, "Samantha, I really am sorry, I feel so bad for you, for us."

I knew it wasn't her fault it was Wayne's fault. After a few seconds I tuned to her, my eyes pouring tears and I said, "I know it's not your fault, I am sorry we had to meet this way too."

Strikingly enough we stood there talking for a few minutes and after a bit of conversation and laughing at ourselves for crying over Wayne, I offered her a beer. I know I needed one, and I believed she did too. We moved our cars to the parking area and sat on the curb drinking a few beers together.

As the night passed, we laughed, we cried, dropped the hate and animosity we had towards each other and toasted the fact that we were both done with Wayne. The night ended up being okay. I could see why Wayne was attracted to her, she was 5'9, medium to longer length blonde hair, beautiful brown eyes, sexy lips and a smile that could light up the room. She had big C perky breast and an ass to match. She was very personable and I am sure all her life she had to fight off the boys off with a stick. Unlike me who is all of 5'7, thin build with shoulder length brown hair and brown eyes with a skinny physique and small B cup boobs.

As we talked and got to know each other more I discovered Jennifer was actually a really nice person. I found out she was 4 years older than I was and had actually went to the same high school I did. She was also in education, but was working with special needs children downtown and had been working at that school since her graduation from college in 98'. By the end of the night, we had both apologized and forgiven each other leaving the gas station with a big hug and a promise to each other to watch out for guys like Wayne. I could have stayed there all night talking to her, because it was nice to have a common bond with someone and our conversation helped our hearts start to heal. I thought about her and the whole situation for the next few days, nothing sexual at that point, just hoped maybe I'd see her again.

Fast forwards a few months...

After working for a bit and saving up so money, along with the help of my parents, I moved into my own apartment in the suburbs of Fort Lauderdale. I was beginning my place in the world, new job, good pay, good friends, cable TV, a fridge full of college style food and a couch, coupled with the freedom (and bills) that come with being an adult. One rainy night in mid-November I was home alone, bored and lonely. I was flipping through the channels and came across the adult section. I really hadn't been horny and had not found anyone that I was interested in dating, or made me think of sex, but tonight sex was on my mind. As I flipped through the channels, I came across a scene of a man and a woman and I watch in full attention. It got me turned on, but not as much as I had hoped. After that scene ended there was a lesbian best friend's scene that came on the screen.

The two girls who were clearly friends but by the end of the evening ended up in a romantic lust for each other. Normally this wouldn't do anything for me, but one of the actresses looked really similar to Jennifer... Wow, Jennifer! I hadn't thought about her in a long time. I couldn't take my eyes off the screen as these two actresses slowly undressed each other and ended up licking and sucking each other's tits and pussies. I kept just seeing Jennifer lying there getting licked and fingered and my pussy started getting wet. I mean very wet. I was pulsing. As the scene progressed and their passions erupted more, I couldn't get my hands down my panties fast enough. I rubbed my clit in circles getting more and more turned on. I ran my hand up and down my pussy lips after my first orgasm. I was so wet that I slid a finger deep inside myself, keeping in time with the girl on the screen who was being fingered, bringing me to my second orgasm. I was acting out the movie. My eyes were locked on the screen, I had never seen two beautiful women like this before, especially one that looked like Jennifer.

The more I watched the more intrigued and turned on I got. I couldn't stop watching these actresses fucking each other hard. I closed my eyes and pictured Jennifer's hand down my panties, while I had my hand down hers. Our lips touching, our kisses passionate and deep. My pussy throbbed for more. My stomach tingled and I got so engrossed in my own thoughts I felt like I was going to explode. I had never masturbated thinking of woman, but now I was soaking wet getting off on it. I pushed my hand down further and rubbed my asshole. I've always enjoyed anal sex and anal play. I loved when someone (or even by myself) played with my pussy until orgasm and then turned attention to my ass. OMG! I was going to cum again THINKING OF HER.

In my thoughts I was wishing she was here, wishing it was her mouth wrapped around my soaking wet pussy, fingering me while I moaned in pleasure, wanting to take my first leap into lesbian sex and eating her out. I fingered myself to another orgasm as I lay listening to the actresses on screen screaming in pleasure. I finished by licking my pussy juice off my fingers, catching my breath and hopping the neighbors didn't hear me. As I lay there that night I though of Jennifer a lot and the lesbian scene I just watched. I thought about how much it turned me on. Why? I don't know. Was I suddenly into women? Was it just a spur of the moment action? Because outside of a few drunken college nights of kissing girls on the dance floor at bars, I had never even imagined lesbian sex or even wanted lesbian sex. But tonight, I got myself off watching two girls and thinking of Jennifer. It was quite an interesting night.

Judy's B-day party.

After returning from Thanksgiving break one of the teachers at school had her 30th birthday party. We were all going to the Mexican restaurant after work to eat and have some Margarita's. This restaurant / bar is quite popular for their big drinks, great music and dancing. We weren't there more than two hours when I was at the bar buying a few more Margarita's for our group, when I heard someone say, "Samantha?"

I turned to look and it was Jennifer! Oh lord, it's Jennifer. We leapt into each other arms, giving each other a great big hug.

Jennifer said," It is so good to see you."

I agreed it was great to see her. She asked me, "Why are you here?"

I told her "I am here for one of my co-workers B-day parties."

I asked her why she was here? Jennifer replied, "I am here as a 3rd wheel for a friend who was meeting a guy and a few of his buddies for drinks."

Jennifer said, "I just got here a bit ago and I'm already bored with the people I'm with."

I invited her to join our group and she jumped at the chance. As I got back to our table, I introduced Jennifer to my co-workers. Some of my co-workers asked how we knew each other? I told them of the odd story of us meeting mid summer after the guy we were both dating got caught up in his BS. A few were intrigued and surprised, but most people laughed it off.

During that night, Jennifer and I had such a great time together, we drank, we danced on the dance floor, we sang songs, we flirted with single men knowing we weren't going to date any of them. Finally, the night was coming to an end and even though I was off tomorrow, it was time to go home. Jennifer and I exchanged numbers and decided to stay in touch and hopefully hang out. During the night with her on the dance floor and flirting with the boys, I kept thinking back to my night alone watching the lesbian porn, thinking if that's how Jennifer looked naked and what a hot sexual experience it would be if her and I hooked up. I was very buzzed and if she would have tried to kiss me or even invited me back to her place I probably would have accepted. I don't know what it was about her, but I was turned on by her and wanting to see more of her.

Late that night after getting home, I masturbated thinking about her again and sent her a text message saying, "I hope you made it home safe, otherwise I'll feel bad I didn't take you home myself."

She replied after I feel asleep writing. "I did get home safe, but wished you would have brought me home."

Over the next few weeks Jennifer and I texted and talked a lot. We made plans to hang out on the Saturday just before Christmas. We would start off with mani-pedi's and some shopping at the mall. Followed by dinner and a night at a club drinking and dancing. I looked forward to it all week. I was very nervous when I arrived at her place to pick her up for our nail appointment. I wasn't sure she had the same feelings for me as I did for her. Or did I really have feelings for her? Or just some sexual lust because of the porn movie? Was my infatuation merely sexual, an innocent fantasy or because she was a new friend in the same field I was in? Was my lack of sexual experience with men, because I was Bi-Curious or even a lesbian? Was it just because of the girls I kissed in college was now leading up to more?

I didn't want to be bothered by these thoughts so I just cleared me mind and went with the flow. Our time together at the mall was great, we chatted we walked, we tried on clothes, we flirted and even walked hand in hand a lot through the mall. Afterwards, we had a wonderful (somewhat) romantic dinner at the local steak house. We went back to her place afterwards and put on the new dresses and heels we had bought at the mall. Remember Florida winters are warm and being in a club packed with people can get hot.

As I stood on her bathroom getting ready, putting on my lipstick, I thought to myself is tonight the night? Am I about to try lesbian sex? As I walked out, I saw Jennifer in her new dress. It was an amazing deep colored gray long flowing maxi length dress, off the shoulder with straps with hints of highlights within it. Jennifer asked me, "How do I look?"

I replied, "You look amazing."

She did look amazing and it made my mind wander even more. My dress was more of a summer floral print just above my knees. We both bought new jewelry while shopping, so we put those items on and sprayed ourselves with her favorite perfume. We left our cars at her place because we knew we were going to be drinking and called a cab for us to go to the bar. Jennifer recommended this sports bar just about 10 minutes from her place.

We arrived and the place was crowded but not jammed packed. We started drinking and sat and talked at a table, our eye contact was amazing. I kept thinking to myself what a beautiful woman she is, her skin was lightly tanned brown, smooth and silky. Her face was pretty as an angel, her hair free flowing and luscious. Her tits filled her dress perfectly, just starting to reveal her cleavage. I was enamored by her. As the night progressed, we started dancing and flirting more with each other. There was one point on the dance floor we were moving slowly to this cheesy romantic song and I wanted to kiss her so bad. Our eyes were locked on each other and I was screaming in my mind for her to kiss me. We both had admitted throughout the night how much we had grown fond of each other and how nervous we both were for tonight's date. I didn't know what was going to happen, all I knew is that the alcohol lowered my inhibitions and I wanted her to rip off my panties and eat my pussy right on the bar. Every inch of me was tingling with excitement, suspense, nervousness and desire.

It wasn't too late in the evening but Jennifer and I were getting tired. We decided to call it a night, the bar was getting overly crowded and noisy. We called for a cab and stepped outside to wait. While waiting Jennifer placed her head on my shoulder and told me, "How pretty I was and how much of a great night she had and she was glad I was here with her."

I replied, "I was glad I was there to."

When our cab arrived Jennifer climber in first, her perfect ass outlined by her sexy dress. I climbed in after. As we rode home the warm air of this Florida night came through the open windows. I didn't know what was going to happen next. When we got place to her place, should I just leave? Should I see if she invites me in? Should I try to kiss her goodnight? Just a while back, I wanted her to fuck me on the bar and now our night out was ending and we were heading home. My wants and desires, turned to fears and concerns. Did she feel the same? Was she as turned on as I was? Was she feeling the same way as I was?

Suddenly, I felt Jennifer's hand rest on my left thigh. Her hand slightly pulled my dress further up my leg. I looked over at her and she had this I want you now look in her eye. My heart skipped a beat. As we moved on in traffic, Jennifer's fingers rubbed up and down the top of my leg, with the front and back of her hand. On occasions she'd slide her hand up my inner thigh, I licked my lips. I watched her hand slide up and down my leg and slightly under my dress. I wanted her to touch my pussy, I wanted this cab ride to be over. I wanted her to touch me like she wanted. I placed my arm over hers and put my hand on her thigh.

At that moment my heart skipped a beat, I got butterflies in my stomach and my pussy tingled. Jennifer leaned over towards me and whispered in my ear, "I want you."

I looked at her and smiled, mouthing the words, "I want you too."

I can't believe I just said that! I can't believe this is happening. So many thoughts went through my mind... Am I ready for this? Is this a one-night thing? Will I be able to eat her pussy? Will she? Will I be a lesbian now? How will I tell my family? I don't know if we were both consumed by the alcohol or just consumed with each other but for the rest of the cab ride home, Jennifer leaned against me and we held hands lightly softly caressing each other's fingers. I leaned over and whispered to Jennifer that, "I had never been with a woman before and I was very scared but excited. But I wanted her and have for some time now."

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