Island Adventures Ch. 02 - Monica

Chapter 1 introduced the main characters, Mike, Monica, and Cheryl. Mike ends up leaving his job working as a bartender for Monica to work as a mate on Cheryls charter sailboat.

In this chapter, Mike and Monica's relationship moves from casual sex to something more.

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After my first trip out as the mate on Cheryl's charter sailboat, I was back at Monica's beach bar to grab some dinner and see if Monica could shed more light on Cheryl for me. It turned out to be a busy night at the bar and the new barmaid wasn't up to speed yet, so Monica didn't have time to chat until after closing. "Where are you staying tonight?" she asked.

"Is that an invitation?" I countered.

"What do you think?" she replied coyly.

Against her protests, I helped her cleanup and then we walked back to her place. A couple nights before, we had slept together just as we had countless times in the previous six months, but something about that last time was different and we both knew it. Monica wasn't quite old enough to be my mother, but she always treated me as if she was (if I didn't counted having sex with her). Sometime in the previous 72 hours, I felt we went from being friends with benefits to being lovers. I wondered if she was having similar thoughts.

As we strolled through the half-empty streets, we chatted about my experience on Cheryl's boat. I told her that after a slightly strained beginning, I was getting used to Cheryl and thought she was starting to warm up to me, as well. "Cheryl's a good kid," Monica said. "She hasn't had it easy and worked hard for everything she's ever gotten."

"Tell me something," I asked. "I invited her to join me at your place for dinner and a couple beers, but she said it would ruin her reputation as a hard-assed, dyke bitch, man-hater." Monica couldn't suppress a grin at that last statement. "She tried to make it sound like she was joking, but I could tell that she really thinks some people believe that and it bothers her. Why would she think that?" I asked.

Monica didn't respond for a while as we continued walking slowly together. Finally, she answered, "I don't know where she might have heard that, but like I said before, she's had a hard life and made some bad choices. Before coming here, she was badly abused by a boyfriend years ago and the break-up didn't go well. He put her in the hospital for a couple of weeks. When she got out, she took some martial arts training and was a quick learner. The, she had trouble with one of her mates a couple years ago and he tried to get physical with her. She may look like a little wisp of a girl, but she's tough and strong. She managed to put him down and in the process, nearly killed him. He was not a little guy, either." Monica paused her story to eye me carefully. "She's never dated another man since she got out of the hospital, so I guess that's the source of at least part of that rumor. She can be tough to work for, but she isn't that way for some kind of power trip. She found out quick that if she wasn't tough, guys wouldn't respect her. After all, she works in a job area that's pretty much all men. That's something I can understand real well myself!"

I nodded. "That's too bad, because I think she's a very warm and funny woman under that façade."

"Oh, really? Are you getting ideas about her already?" Monica asked with an arched eyebrow.

"Me? Hell no! I'm perfectly happy with you and I'm pretty sure that Cheryl isn't interested in me as anything but a deckhand," I declared. Monica studied my face briefly, but didn't say anything more about her friend.

We arrived at Monica's small house and minutes later, we were cuddled up in bed together. I started with kissing and suckling Monica's long nipples, but remained careful around their matching gold ring piercings. During one of our first encounters, I got carried away and almost pulled one out, leaving Monica with a very sore tit for a few days. Moving from her nipples, I gave each breast a circlet of small bite marks. Each tender bite caused her to moan softly and writhe under me; I knew that it was something she enjoyed.

I moved up from her breasts to kiss and lick her neck on each side, from her collarbone up to just below her ear. She was ticklish under her ears and as I neared those areas, she couldn't help giggling and twisting her head to try and keep me from tickling her more. From her ears, I moved back to her mouth and we enjoyed a kiss that was long, soft, and full of restrained passion. While our mouths joined, I reached down and began lightly circling a couple of fingers across the folds of her damp pussy

She was breathing hard when our mouths separated and I quickly slid down her body to kiss and lick her smooth pussy. The first time we slept together, she told me that she used to have a large, thick bush, but had to shave her pussy completely to wear to swim suits she liked. The first time I saw her in a swimsuit, I understood what she meant. A single square of toilet paper had more surface area than her entire bikini bottom! Even her one-piece suit was pretty daring and covered very little below her waist.

That same time, I also found out that she had two piercings in her pussy, one in each outer labia. She said the only time she ever took them out was when she wore a swimsuit in public since the small dumbbell-shaped rods showed up prominently under the taut fabric covering her cunt.

Her pussy was already getting wet and my tongue hastened that process. Her clit was hard and easy to find as it protruded conspicuously from between the soft pink folds surrounding it. Once, she let me place one of her nipple clamps on it, but made me take it off minutes later because it was driving her crazy. As soon as I opened the clamp, she said it felt like fire was rushing through her clit. As excited as that made her, Monica was never in a hurry to try that particular technique again.

I sucked her clit up between my lips and pressed them together a little tighter around the hard little nub. Monica's body stiffened and she let out another cry, "Oh God! Oh, God!" I proceeded to suck her tender little bud in and out of my lips as if it was fucking my mouth and less than two minutes later, her pussy juice flooded over my tiring toungue.

I licked up every drop of her tangy, pungent cum and rose up to see her chest slowly heaving from her excitement. I wasn't finished with her yet, though. I licked and kissed my way down the inside of her thighs and several times, her pussy gave a sudden spasm followed by a small outflow of her juice oozing from her hole. "Oh, you motherfucker!" she called out in a soft, exhausted voice.

I grinned back at her in the dim moonlight that filled the room. "How can you say that? I haven't even fucked you, yet," I answered playfully.

"What are you waiting for? Hurry up and put that thing inside me where it belongs!" she called down to me.

"I don't know. Your cunt looks pretty stretched out already. I'm thinking I want something tighter, like maybe your ass!" I replied. Monica was not into anal sex of any kind. We had that discussion a long time ago, but I still would kid about fucking her ass.

"I don't care where you put that cock of yours. Just hurry and get it inside me!"

That was a new answer from her; I wondered if she really meant it. It didn't matter because I wasn't going to try to fuck her ass like this. If she ever did want me to, I would want to use a lot of lubrication and take my time preparing her. At this point, the matter was moot because my cock wasn't hard enough to penetrate anything. I moved up to sit astride her chest and offered my soft dick to her lips.

Monica's mouth opened and I felt the familiar warm, smooth, wetness of her tongue gliding over and around the head of my dick. I reached down and supported her head as she moved it up to take more of my cock in her mouth. It wasn't the best blowjob I had ever had, but it was more than adequate to get me hard. I slowly moved myself in and out of her mouth, letting her neck rest while I fucked her mouth and my arousal grew.

When I was ready, I pulled myself out of her mouth and moved back between her legs to gently impale her with my thick pole. "Oooooohhhh!" she moaned softly as I entered her and slowly filled her cunt with my entire length. Once the base of my cock hit the pick opening of her cunt, I paused and leaned down over her panting form. My arms slipped under her shoulders and my hands cradled her head through the thick, waves of auburn hair cascading around her. Her arms circled around my neck and we slowly moved together in perfect synchronization.

My pubic bone rubbed over her exposed clit, exciting her further as our mouths met again. Our kiss was just as soft and tender as before, but even more passionate. As we maintained our gentle rhythm of love-making, I couldn't help but to think of how different this time was from our previous encounters.

For several months after I started working for her, we enjoyed having sex together. Monica made it clear at the beginning that I was just one of her fuck-buddies. Sex was about physical pleasure and sometimes trying out new experiences together. It was always fun, neither of us ever took it too seriously, and we often laughed together at some of our failed "experiments". We lived only in the moment and never looked to the future. There was never any commitment by either of us and we were both fine with that.

However, the night I quit Monica's bar to work for Cheryl, Monica and I made love for the first time. I didn't understand it at the time, but knew something had changed. Overshadowing that night was the unspoken thought that it might well be our last time together. While neither of us admitted it aloud, our bodies did the talking for us. When we coupled that night, more than bodily fluids flowed between us. I felt an emotional bonding that I never experienced before, and from Monica's reaction, she felt the same thing.

That moment was partially diminished by the knowledge that I was leaving and perhaps that is what silenced our voices. I already knew that we were more than fuck-buddies and that I cared deeply for the older woman who had taken care of me and treated me as a partner. I found myself wanting badly to do everything I could to pleasure her. When I finally did enter Monica, I felt a tremendous closeness I had never experienced before and I wanted to prolong that feeling as long as possible.

I moved in and out of her effortlessly and our physical union felt smooth and seamless. I noted the pressure of her pussy around my shaft and it felt perfectly balanced on the amount needed to maintain my arousal without inducing my own orgasm. Monica's fingers ran lightly over my broad back and since small tingles of excitement though my body. Her breathing was relaxed as her body rose and fell in unison with my movements. Her eyes were beautiful liquid pools looking up at me and the gentle smile on her lips conveyed love. My mind focused completely on sensing everything about her body as she responded to my actions, yet I continued to strain harder as if to gain a more tactile feeling of her emotions.

I lost track of time and barely remembered the whispered sounds we made to each other of promised love. When Monica climaxed for the second time that night, she gave little warning and I found my body responding immediately. Our mutual orgasm could not have been more precisely orchestrated and when the last of my seed was deposited deep inside her womb, I fell exhausted over her.

After a few more seconds, I held her tightly and rolled to one side, keeping us coupled. I felt a sudden sadness at the recognition of the impossibility of our relationship, but at the same time, I never felt more content in my life. We were both tired from a long day working and now mentally drained from our physical and emotional intercourse. As I drifted off to sleep, I imagined hearing Monica tell me, "I love you" and I murmured "I love you, too."