I was dared to write a short story. I couldn't think of a subject to write about so I decided to tell of something that happened to me in Key West back in the late 90's. I think of this because of a topic started by Kitty asking
if a person from the same sex had ever hit on you.I was looking forward to this trip for a while. I had 7 days leave from the army and decided to spend 4 of those days with my good friend from college. The remaining days would be in Miami with my parents and sister. I arrived at the rental house just east of Key West, my friend Jill was already there.
Having not seen each other in over a year, we caught up with each other over a couple of beers she had picked up at the store prior to my arrival. She told me about things with her new job. I told her about the army life. We decided to head out and get something to eat, before hitting the bars for dancing that night.
Over a light dinner we had some margaritas which were a 2-1 special. I think we had 3. From there we walked the town and checked out the souvenir stuff they sold before ducking into another bar. The crowds were starting to pick up. I remember drinking some whiskey and a jagermeister shot. The crowd started to disperse to watch the sunset. The bartender said there were too many clouds on the low horizon for a good viewing and suggested we stay for a free drink. We took him up on the offer. He was cute and Jill was starting to hit it off with him.
We asked where to go for dancing. He suggested Sloppy Joe’s and that he would be going over about 11:00pm. We finished our drinks and headed over to his suggested bar. The sun was already down and when we got to the bar it was packed.
Jill grabbed my hand and we headed straight for the dance floor. The band was rocking the place and we soon worked up a sweat over a number of songs. Jill commented on how hot it was. We were both in light tank tops and shorts. I pulled my hair up and suggested we go outside for a bit to get some cool air.
When we got outside, we noticed a little convenience store down the street a bit. I suggested we grab a water. Jill agreed. After walking out of the store we did a little people watching. Key West is the perfect spot for doing that.
It was a minute later a guy walked up and said, “You ladies need some smoke?”
Jill said, “Yeah.” And bought a joint off of him. We had discussed earlier that neither of us had smoked in a while and decided if the opportunity came up, we’d have some. We were the two pot smokers back in college. In fact, Jill had a bong that we would use when we partied.
We headed to the beach with our joint and sat on the beach. We smoked half of it down while listening to the waves lap up on the beach. After a coughing fit by Jill, we decided to save the rest for later in our trip. We headed back to the convenience store and got some eye drops before returning to Sloppy Joes to resume dancing.
After a couple of dances together we got a couple of drinks from the bar. They were tall and colorful and had a lot of rum in them. Looking around there was nowhere to sit so we just hung out near the stage watching the band.
About 10 minutes later, a girl that looked a few years older than us invited us to her table with her friends. We took her up on it and we were soon screaming over the noise of the band introducing ourselves. There were 6 or 8 of them. I really don’t recall, I was pretty tipsy and the marijuana had me messed up a little bit. I remember they were drinking the same thing we were. It must have been a special that night. I also remember a few more rounds coming to the table and we’d holler in joy each time the waiter set them on the table.
Jill and I got up and danced, along with two of the girls from our table. We danced a few songs and sat back down. Jill ended up across the table from me and we couldn’t really converse. I started talking to the girl next to me. I just remember how pretty she was. I remember telling her I was on leave from the army. We talked for a while and then a song came on and she said how much she loved the song and said, “Lets dance.”
We headed to the dance floor, her pulling me by the hand. We were having fun and acting silly. We danced for a couple of songs and then a slower song came on and couples started embracing on the dance floor and slow dancing. I motioned toward the table and she said, “No, lets dance, I love this song.” She took me in her arms and I put my arms around her. Our faces were very close to each other and she smiled at me and told me to look to my right. I looked and there were two women kissing. I looked back at the girl I was dancing with and her face was suddenly much closer to mine. She leaned in and kissed me on the lips and backed away. I don’t recall what my response was, but she leaned in again and this time her mouth opened. So did mine. I had only kissed a girl one other time and I remember it being nice, as this was.
We kissed through the entire song and the band went into another slow song. I could feel my cheeks burning. I could feel my body responding. Her hands had slid from around me to my rib cage and I could feel a hand on the side of my breast.
Suddenly, I heard Jill’s voice, “Jules, we need to go sit down.”
I looked at her and then back at my dance partner. “No, I don’t want to.” She tried pulling me by the hand. I pulled my hand back and said, “Jill, it’s fine. Go sit down, we’ll be back in a minute.” I turned back toward my dance partner and we resumed kissing as Jill went back to the table.
My dance partner whispered in my ear that she wanted to show me the beautiful Florida night sky. She had a special spot we could go. Then asked me if that was okay. I was hot and going outside would feel good, so I nodded. She took my hand and we walked in the opposite direction of our table through a door way. We climbed two flights of stairs and I found myself on the rooftop. I was led by the hand to some lounge chairs. I then noticed they were scattered all around the roof top, but nobody but us was up there. She sat down and spread her legs and held out her hand. I took it and she guided me to a sitting position between her legs and had me lean back into her body. It felt good. It was nice and cool up there and it was nice laying back into her.
Her one hand was on my stomach beneath my shirt, the other was running her fingers through my hair. I could feel her head come around the other side of my head and she began kissing my neck. That is a soft spot for me. I closed my eyes enjoying the sensation. I thought of how buzzed I was. I thought of how marijuana makes me a bit horny. I remember thinking I have only kissed one other girl, that was in college, but that was as far as it went – a kiss.
I was enjoying her lips on my neck. Her hand slid up from my stomach on to my breasts. I remember saying, “No, I’ve never done this.”
She whispered, “Then you don’t know how special it will be.”
I didn’t respond as her fingers pinched at my nipple. She gave it a squeeze and a rolled it between her finger and thumb. I moaned. She was still kissing my neck and her hand went to my other breast and first teased my nipple by rubbing it through the bra, then tweaked it between her finger and thumb. I moaned again.
She had me sit forward, I was thinking our fun was over. And felt a bit relieved. Then I felt her lifting my top on my back and then my bra was loose. I said, “No”, again.
She replied, “Yes, Julie.”
She lifted my tank top higher and I raised my arms allowing her to lift it over my head. From behind she guided the bra down my arms. Somehow she got out from behind me and she told me to lay back and look at the beautiful stars. The lounge chair was now reclined to a flat position. She knelt down beside me and began rubbing my belly with one hand and my breasts with the other. Then the sky was obstructed as her hair fell across my face and her lips were on mine. I kissed her back, even going as far to place my hand on the back of her head encouraging her.
Her hand slid down my belly and I felt it at the snap of my shorts. She fumbled with it trying to do it one handed. Then she whispered in my ear. "Unbutton it." I reached down as her hand went to my zipper and slid it down. I freed the button. She slid her hand from my belly to my underwear waist band and rubbed just her index finger back and forth. My breathing had quickened.
“I’m going to make you feel so good,” she said. Then her hand slid deep down the front of my shorts and cupped my entire area. Only my underwear separated her hand from my private parts.
The palm of her hand was rubbing at the top of my lips and my clitoris could feel the pressure. Her four fingers were lower rubbing gently in a circular motion, I know she could feel the heat.
I remember saying we needed to stop. We were outside in the open air and I feared we might be seen. And the sounds of the partygoers could be heard just over the edge of the building on the street below. Plus, I had never done this with a woman. She told me we were not stopping and assured me that nobody would see us.
Her lips came forward and kissed my cheek, then she made her way to my neck, then my breasts. I hadn’t even realized her lips were there because her finger was teasing me at my opening, through my underwear.
She sucked on my nipple and my hands went to her shoulders to push her away. I had no strength in me and just rested my hand on her shoulder instead. A moment later, my hands went to the back of her head and held her to my breast. If just felt so good.
She backed away from me and pulled her hand free of my shorts, only to put them on the waist band, along with her other hand. I knew what she wanted and lifted my bottom. She slid the shorts and underwear down my legs and set them on the chair behind her. I laid there completely naked before her.
Her hand went onto my thigh and began rubbing me softly as her mouth returned to my other breast. My hand went to the back of her head, holding her to me again. She pushed outward from the inside of my thigh and I willingly parted them. She then lifted it from the lounge chair. I knew what she wanted. Lifting my leg over the edge of the chair, I planted my foot on the rooftop. Now opened up for her a bit more, her hand slowly slid up the inside of my thigh and began playing with my sex. Her finger touching me very nicely. I let out a whimper as a small finger entered me while her thumb caressed a bit higher.
Her lips left my nipple and she began kissing down my stomach. I whispered "no" again but this didn’t stop her. I felt her lips in my pubic hairs, kissing me there. Her other hand touched the inside of my other thigh and opened my legs wider. She leaned forward and I felt a tongue lick from the top to the bottom of my spread lips. It felt so good. My hands went to my own hair. I remember grabbing it and actually pulling it a bit as I was brought to a phenomenal climax over the next few minutes.
She sat up on her knees. And crawled to the end of the lounge chair. She lifted my feet up and put them over her shoulder, moving forward so the the back of my knees were resting on her shoulders. If it was a man, I would have felt hesitant. After what she had just done to me, I was comfortable allowing her to put me in this position.
She leaned forward and began using her tongue on me again. Her hands grabbed mine and she guided them to my breasts. With her hands on top of mine, she kneaded my breasts. It was a few minutes before she released my hands. As I approached my orgasm, her hands slid down to the small of my back. She slid them toward the top of my butt and began lifting me. My shoulders still on the chair, my lower body arched up, giving myself to her. I tried to muffle my scream as I came in her mouth while kneading my own breasts, looking up at the stars in the sky, and hearing the jubilant crowds in the street below.
It was a few minutes later that I recovered enough to put my clothes on. She helped me up and we walked to the edge of the roof. We leaned on the wall looking over. She was holding my hand and I looked at her and kissed her. I could taste myself on her lips.
“Let’s go get a drink and dance some more," she said.
As we approached the doorway, my friend Jill suddenly appeared. She was holding the hands of two of the other girls.
She just smiled at me as she was led to a chair.
A couple of hours later, Jill and I got a taxi back to the rental house. We both crawled into our own beds not saying anything about it. In the middle of the night, Jill crawled in bed with me. She gave me a kiss on the lips and said, “I had fun tonight.”
“So did I,” I answered.
I think she wanted to do something with me, but I just said that I needed to sleep. We talked a bit about it the next day. I confessed it was my first time with another woman. She told me she had one experience after college and another with her sisters friend a few months before.
The next night we took it a little easier on the alcohol, but enjoyed the remainder of the joint as we watched the sunset. After that we went dancing.