Growing up in my family meant multiple vacations a year in Chokoloskee spent fishing with family and friends. I loved every vacation we had there.
This one year in particular we went with several of my parents friends and their families. I was freshly 21 years old, went through an extremely ugly break up and drinking all kinds of alcohol. My parents one friend Macy, was recently separated from her husband and we had gotten to talking just in general, we had several things in common. We made drinks and spent the first evening there making Jell-O shots for everyone so they could cool over night. We mixed the blue jello with vodka, the red with rum and the green with tequila. We had the place to our selves and were just talking more about our most recent heartbreaks while we took turns passing the left over liquor bottles back and forth taking shots out of each. I came up with the genius idea of playing “Never have I ever.”
Almost everyone knows about this game, it’s a fun way to learn “fun facts” about your friends. The questions vary from “never have I ever kissed a girl” to “never have I ever popped a Molly” to anything else you can think of that you haven’t done, that someone else playing has done. If anyone in the group HAS done it, then they’d have to drink. So now it’s just the two of us playing and obviously we are getting drunk extremely fast.
We were like two teenage girls giggling and leaning into each other on the couch. We had music playing and it was just genuinely a great memory. Macy and I ended up passing out that night on the couch, woke up the next morning around 6am to head out fishing for the day. We were all out on the water for hours that day, came back in for lunch and cooler refills. Before heading back out Macy came walking down the dock in these daisy duke shorts, the top button was undone so her bikini bottoms were peaking through, her tank top was in her hand and her gray bikini top with orange and gold designs was all I could see. I put the boat in neutral and told shouted for her to go out on the water with me this time! I was fishing on my own anyways, some company would be perfect. She hurried up, hopped on and we were off. A side note you need to understand is Choko is also called 10,000 islands. There are so many islands to get lost in and different fishing areas, finding privacy out there isn’t hard at all. So I get the boat on a plane and run south down to one of the fishing spots I know of. As I’m running, I kept glancing over and couldn’t help but to begin to notice how attractive Macy is. Yes she’s much older than I was but she had this short burgundy hair that fit her fave perfectly and when she wasn’t wearing her glasses, I could see these darker green specks in her eyes when the sun hit them at certain angles.
She was sitting next to me and was relatively close to me, but I was comfortable with her so it wasn’t a big deal.
We got to the fishing spot, I slowed the boat to a stop just off the islands ledge and oyster bar. I put the power pole down and rigged both rods up with popping corks while she made us both a drink. We did a “cheers” and cast our lines out, music playing and our conversation started back up from the previous night, talking and spending time with Macy was like hanging out with a long lost friend. I was comfortable, I was able to be myself and I was happy in the moment. After a couple hours of fishing we had gotten a couple keepers and decided to let the boat drift along the back of the islands and we laid out towels and relaxed, enjoying the sunset, music, drinks and salty air. Somehow the conversation turned into Macy questioning if she preferred women over men. I said “I’ve only been with girls that choose men, they tell me there’s a comfort level when they’re with me that they feel safe to explore their curiosity.” She sat half way up, there was a look of relief on her face. I asked what was wrong, she took a big swig from her cup looked at me and said “your parents can’t know this happens.”
She set her cup down and leaned in to me, slowly she touched her nose to mine and our lips brushed each other’s. I ran my hand through her hair and pulled her into my kiss, this kiss was unlike any other kiss. There was a yearning I felt from her, it was like she needed this kiss, this experience. I paused every few minutes to make sure she was okay with everything, after the fourth time I asked she pushed me down and said in a very stern voice “quit asking if I’m okay, I’m fine, I want this to happen.”
We went back to kissing when I happened to look up I and notice we were drifting into the mangroves, I hopped up and backed up out. She came over to where I was, sat down on the bench and once I put the power pole back down so we’d stop drifting, she wrapped her legs around my waist. I turned around while between her legs and pulled her closer to me by her hips. She threw her arms around my neck and we kept kissing. I knew there was no one around us and we would’ve had plenty of notice by hearing a boat coming so I decided it was safe. I pushed her biking top to the sides of her breasts, kissed her hard and caressed her breast in my hands. She moaned into our kiss and said “please don’t stop.” I softly but her collar bone and slid my hand down her side, into her pants and I could physically feel her throbbing. I instantly pushed two fingers into her, she arched her back, pushing her hips into my hand and scratched down my back. I kept pushing my fingers into her, I wanted to fulfill whatever experience and expectations Macy had. She kept scratching her nails down my back and it was turning me on more. She whispered into my ear that she was going to cum and I stopped, I said “not yet.” I pushed her back so she was laying on the bench and began kissing her again, her legs were shaking and she kept trying to push my hand back into her pants. I wanted to tease her more before she got off, I slid my hand into her pants and let my middle finger slide against her clit. She was soaked and bit into my collar bone so hard it actually took the air out of me for a moment. I eased three fingers into her, she gasped and then moaned louder than anyone I had ever been with. I loved it, I wanted her to get louder, I continued pushing my fingers into her and she went back to scratching the backs of my arms and my back.
The sun was setting and I knew we’d have to get back extremely soon. I kissed quickly down her neck and stomach, I bit her hip bone all the way down to her inner thigh and I gripped her hips with my left hand as I pushed my fingers into her hard. I knew I could reach her g-spot so the second I felt it, I began pushing against it. I flicked the tip of my tongue against her clit, she kept trying to push her hips into me but I wouldn’t let her. I held her hip pressed down against the bench and told her “now you can cum.” She grabbed the back of my head, pushing my mouth into her and rocking her hips. She squeezed her legs tight around me, I could feel them shaking, her breaths were loud as hell and her moans doubled that noise. Until everything let go, she sighed a long shaken breath, her grip let go of my head, her legs dropped to the sides and she laid there, her hips twitched twice and she looked at me, giggled and said “you could turn any girl you wanted to, no doubt about it.”