I get to eat a lesbian's pussy, then fuck her pussy.
54. Is Jenny A Lesbian?
I got stalled on my passage up the east coast of Florida. I had taken a mooring ball in a large, protected harbor. The marina had all the essentials and there were a plethora of bars, restaurants and stores nearby. It's what we call a "sticky" or "velcro" harbor: hard to tear away from. A couple hundred boats all with boaters living in the same situation tends to build bonds. A certain comradery exists.
In the morning I went ashore to shower. The bath house was a long, rectangular building with doors along the sides housing private bathrooms. Just as I stepped out of my bathroom, a woman in her mid-thirties stepped out of the one next door.
"Oh, hi. Good morning. I don't think we've met. I'm Sailor."
"Good morning, Sailor. I'm Jenny. We haven't met but I've heard about you at the Tiki Hut. People speak highly of you."
"People say I get high! The audacity! Let's hope my probation officer doesn't hear!" She looked horrified that I had twisted her words and taken them to the dark side.
"No, no ... that's not...."
I interrupted. "Just kidding, Jenny. Sorry. They only let me out in public on special occasions."
She wrinkled her forehead and tilted her head. "Special occasions?" You could tell that she hadn't caught on to my sense of humor yet. "What special occasions? Is today special or something?"
I got a shit eating grin on my face. "Of course today's a special occasion. It's the day we're going out to the reef on my boat."
"But I've never been out to the reef."
"That's why it's a special occasion. Come on. We have all day. I even have some crumbs to feed the fish with. They're amazing, all different colors, sizes and shapes. You'll love it."
Still somewhat baffled, Jenny simply followed along. We dinked to my boat and climbed aboard. It didn't take long to tie the dinghy for towing and get the instruments and the motor going. I asked her if she would go forward to untie us from the mooring ball.
Jenny was cute. About 5'4", sandy colored hair just covering her ears, and a roundish face but with a square jaw if that makes any sense. Suffice it to say that she was cute. Her body was stout, her frame solid with few curves. One redeeming feature was her chest. Nearly perfect tits in size and shape. They drew your eye. Overall, she was maybe a 6 out of 10.
I watched her move forward on the deck. She didn't have a tight teenage body but what she had looked like a good solid fuck. Her walk back to the cockpit allowed me to imagine groping those perfect tits.
Since she had never been to the reef, I explained it to her. About five miles out into the ocean is a long chain of coral reefs going parallel to the shore from the Dry Tortugas up the east coast. A large reef section, "Big Hat", is just offshore from the harbor.
Once there, the water is 20+ feet deep but so clear you can count arms on a starfish. Blooms of the coral and fish of every color imaginable are visible from the surface. When you throw a handful of potato chip crumbs or crackers into the water, the fish go crazy feeding. Which draws more fish. It's amazing.
Out at the reef are 8 or 10 mooring balls installed so boats anchors don't tear up the delicate reef. We hooked onto a ball and began throwing crumbs overboard. The fish swarmed like crazy, boiling the water in their exuberance to feed. Jenny was awestruck. I stood behind her as she leaned over the side to watch the fish. Looking at her ass bent over like that gave me fantasies.
"You know, people swim and dive out here. Wanna go swimming?" I suggested.
"I didn't bring a suit."
"Honey, I don't even own a suit!" That said, I stripped naked and jumped off the back of the boat. "Come on in! The water's like a bath!" She hesitated, pondering the situation. "If you’re worried about being seen, well, it's only fish and they don't care. And me. I assure you that I've seen naked women before. No worries, babe. Strip down and join me."
Whenever I swim off the back of the boat, I always tie a floating square cushion to a line and have it in the water to hang onto. Holding the cushion I encouraged her. "Come on, Jenny! It's just us and the fish. Noone else is here this early." She turned around to disrobe and gingerly climbed down the boarding ladder with her back to me. She swished over to the floating pillow.
"This does feel nice. Like a warm bath. And I'm sure the salt water is therapeutic. It just feels healing."
"Jenny, I'm so happy for this special occasion. Your first time at the reef! And I'm glad that they let me out to enjoy it with you."
She looked really confused again. "Who is this 'they' and why do they keep you locked up or whatever?"
"Jenny, there is no 'they'. I live alone on my boat. Saying that I'm only let out for special occasions is a contrived way of telling you that I'm different. I'm a vagabond lunatic. I live outside the box. I'm not like other people. When I do 'go out', I always end up doing something that nobody forgets."
She drew a deep breath, pinched her nose and dove under. The water was so clear, I could see her nude body glide down through the water. She kicked her feet and dove down to the coral head. As she was coming up, bubbles were flowing from her nose and mouth. I could clearly see her nicely shaped tits and the dark triangle of pussy hair.
She broke the surface spitting and gasping for air. "Well, I'm certainly not going to forget this special occasion. It's beautiful!" She swam over to me holding onto the floating cushion.
I was done swimming so I climbed the boarding ladder and got some towels. As she started climbing the ladder I held a towel up to shield her and for her to wrap herself in. Once aboard she sat in the cockpit, the towel wrapped around her. I went below and got some refreshing drinks. We sat and talked.
In all of her stories about her life, her travels, her relationships, her jobs there was never any mention of men. It was always Jenny and her girlfriends or her partner. I started wondering which team she played on. So I pried.
"Have you ever been married?"
"Not yet."
"Do you have a boyfriend?"
"Nope."
"Do you have a girlfriend?"
"Not at the moment. I'm between girlfriends."
Ah ... so there's the rub. She's a lesbian. Now I had a decision to make. I could play it several different ways. I decided to act as if I was gay thinking that it might make her more at ease being alone with me. She had pretty obviously been on her guard this whole time.
"Well, Jenny, I'm pretty much gay myself. I say 'pretty much' because I used to date women years ago. And on rare occasions my partners include females or trans shemales in our trysts. I guess if a female is all that's available I'm okay with it but I much prefer males. How about you? Are you exclusive?"
Jenny pondered this for a moment. Finally she offered "I wouldn't say I'm exclusive to women. Like you, I started out dating guys. I just found that women give me so much more sexual satisfaction than guys. I mean, guys just want to stab you with their dick until they cum. That's it. Most don't have a clue how to satisfy a woman."
"Jenny, I told you that I'm not like most people. I'm totally outside the box and I nearly always do something that everybody remembers." Seeing that her drink needed refilling I suggested that she come below to help pour more.
Down below, she got more talkative, more inquisitive. "So what made you switch from girls to guys?"
"Well, to begin with, I much prefer oral sex to the usual dick-pussy thing. All the girls I used to date raved about how I gave the best head ever. In my social group it became sort of a 'thing'. Everyone talked about it and teased me.
"Then one time in college I was renting an apartment with 3 others, 2 guys and a girl. We all got really drunk one night and the girl challenged me. She wanted to know how long it would take for me to get her off using only my mouth."
"Well ... how long did it take?"
"Two minutes, 45 seconds. But then the guys challenged me. 'Bet you can't suck me off that quick' kind of challenge. So I sucked him off in 4 minutes, 20 seconds. Then the other guy in 5 minutes, 45 seconds. I discovered that I really preferred having a cock in my mouth. Nothing against women. It's just more of a challenge to get a guy to cum."
You could see the wheels turning in her head. She sipped on her drink as she digested this info, planning what to do next.
"Two minutes, 45? Really? I like it to last longer than that."
"Remember, Jenny, it was a challenge. Normally, I spend my time, intent on giving my partner maximum pleasure. I aim for multiple orgasms."
Now the wheels grinding in her head were in overdrive. "So, you could make me cum in less than 5 minutes, right?"
"I probably could, but with someone as attractive and intriguing as you, I'd take my time. I'd linger and ensure that you came more than once. Tell me when was the last time someone made you cum."
"Honestly, Sailor, the last time someone got me to cum was over 6 months ago. But I get myself off almost daily. So there's that."
"You know as well as I do that masturbating is just not the same. I can guarantee that I'll do my best to get you to cum, probably multiple times. I'd be thrilled if you let me show you."
Her expression went from "no", to "hmmm, maybe", to "why not?" in a matter of 30 seconds. "I'll let you try to get me off but only if I can time you."
I laughed. "It's not a race, Jenny. But if you drop that towel and lay on the bed I'll get started."
As she spread her legs I got my first view of her fuckbox. Her natural bush framed a generous pussy, fat lips, thin protruding labia with a small, crinkled asshole below. I lay on my belly between her legs and pushed her legs apart.
I worked my way down her inner thighs and basically had a makeout session with her pussy. Kissing, nibbling and using my tongue and mouth on her lips elicited some oohhhs and aahhhs. Once my tongue parted her lips, her hips began twitching. It was only after I latched onto her erect clit that the gyrations really got going.
I paid special attention to her clit, using every trick I had. Her response was commensurate with my efforts. As I worked my magic, I got more and more forceful. My tongue was smashing her clit flat, my lips were sucking it up firm, my teeth were nibbling. When I'd suck it in between my lips, I'd make it scrape against my teeth. She seemed to particularly like that, grunting out groans and bucking her hips.
Once I got my fingers involved, finger fucking her cunt, she was all but done. I'd lift my mouth off her clit and finger fuck her hard. I'd curl my fingers searching for that elusive G spot. Then wrap my mouth back around her clit. Back and forth until she arched her back, urgently exclaimed "Oh my God ... yes! ... YES!" and let her pussy drain it's pent up desires.
Sensing her weakened condition and needing some relief myself, I instantly climbed on top and thrust my hard cock up her sloppy hole. No complaint. In fact, she raised her legs straight up and let me slide my cock in and out until I reciprocated by draining myself into her vagina.
As we lay next to each other, I casually said "You have a really nice cunt. I certainly want you to remember this special occasion. Want me to get you off again?" She reached over, grabbed my wrist and pulled my hand to her pussy. I got busy right away.
I counted eight orgasms, not including two of my own. As we motored the Love Boat back to the harbor, she commented in an offhand way "Took you twelve minutes, twenty seconds for the first one. I didn't time any of the others."