Female about to undergo sex reassignment surgery let's me enjoy her micro-penis and lets me fuck her pussy.
57. The Opposite Gender
Anchored a quarter mile off the east coast of Florida, I had crashed an impromptu fraternity beach party the night before. It went on until the wee hours. A couple of delightful young coed girls had taken pity on me and fucked me delirious. I was slow to wake up and struggled to make coffee and find the aspirin.
I weighed anchor about 9 a.m. During the night the wind had clocked around, now coming offshore from the west. It had also kicked up considerably coming at me at 20 to 25 knots, gusting to 30. These were all signs that a front was moving in possibly bringing inclement weather. Yet none of my weather apps indicated any storms headed my way. And my radar showed nothing bearing in.
I decided to chance it, hoping that the forecasters were right. I deployed both sails and sailed with the wind headed east out into the ocean. Sailing with the wind, letting it just push you along, generally results in a smoother ride. The boat is not leaning (healing) either way. It remains upright. You lose some forward speed but it's generally a pretty comfortable ride.
I sailed with the wind far offshore, about 25 miles. The shoreline had disappeared after the first hour and there was absolutely nothing visible except the water and the cloud studded sky for 360°. There weren't any fishing boats and I didn't see any freighters or cruise ships either. Nothing. Just sky and water.
I saw that it was about 3 p.m. It stayed light out until roughly 8 p.m. I did some mental calculations. I had been averaging 4 knots for 6 hours, getting me 25 miles offshore. If I tacked back toward land close hauled (the sail setting for maximum speed), I could probably hit 8 knots in this wind. It would take roughly 3 hours to get close to shore. That would be 6 p.m., plenty of time to find an anchorage before sundown. I turned the boat toward the northwest, about 45° off the wind. I cranked in the sails for maximum speed. The boat instantly healed over 30° and took off.
I was now speeding back toward land at a respectable speed between 8 and 10 knots. Exhilarating! Fun! Wind in my hair and in my sails! Healed over. Crashing through the waves, the bow sending spray in both directions. A wild ride! This is the nirvana that sailors live for.
Then the unthinkable happened. In the span of no more than 15 minutes, the wind quit. Just quit. It went from 20 knots to 2 knots in a quarter hour. My Love Boat righted itself and slowed to a crawl, my sails empty and luffing in the light breeze. I was now only moving forward at 1 to 2 knots. Oh, fuck! And I was still 20 miles offshore.
In order to get close to land to find an anchorage for the night while there was still some light left, I had no choice but to crank up the motor. What a sad state of affairs. Going from the pinnacle of sailing, healed over, 10 knots, crashing through the waves to this. Becalmed water, no wind and having to turn on the motor. Shit. Guess you just have to take the good with the bad.
As I was motoring along I looked for either an anchorage or an inlet with a marina nearby. I was bummed. All I could think about that would lift my spirits was a tumbler full of single malt and a blowjob. Only the scotch was a sure thing. My charts showed two possibilities. Either an inlet with what appeared to be a small bight just inside the inlet or a tiny marina about a half mile up the Intracoastal Waterway. If I kept the pedal to the metal, I could probably make the inlet by 8, the marina by 8:30.
On the off chance, I called the marina. Sure enough, they were very accommodating. Yes, they had a transient slip. Yes, approach depths were 7 feet minimum. Yes, they could allow a late arrival. They even emailed me a map of the marina with a slip highlighted for me.
"No problem, Mr. Sailor. We'd be happy to accommodate you. We're a 'Mom and Pop' operation. If you text us when you're close, we'll even send a dockhand down to help you tie off as long as it's before midnight. Just come visit the office in the morning and we'll settle up then. Be safe out there and we hope to see you in the morning. And don't forget to text us when you're a half hour away. We'll have someone waiting for you at your slip."
It was nearly 8 p.m. before I got within a mile of shore. Running lights and steaming lights all on, of course. Being unfamiliar with the territory I wasn't in the Intracoastal until nearly 8:30. I texted the marina and found my way there. GPS, satellites, chartplotters showing the way are true lifesavers nowadays. It was nearly 9 o'clock and there wasn't any sun left.
It truly was a tiny marina, maybe 15 slips. They had a large, newer looking fuel dock so I guessed that they made most of their money selling gas, bait and ice to the hundreds of small fishing boats common to the area. With some maneuvering in tight quarters, I managed to find my slip. It helped that they had sent a dockhand to help. The dockhand had a bright beacon searchlight, showing me the contours of the slip.
When I went forward to throw the bow line, I discovered that the dockhand was actually a woman. Once she had my boat secured, I shut down the motor and took a deep breath. "Welcome to Petite Marina!" she called from the dock.
"Howdy! I'm so glad you were here. Not sure how I would have navigated into the slip in the dark without you. Why don't you climb aboard while I collect myself and find my wallet. You deserve a generous tip."
She climbed into the cockpit while I disappeared below. First I shut down all non-essential exterior lights and electronics. Then I poured a tumbler of scotch. I called up to her "I'm having a drink after a long day at sea. Care to join me?" She didn't respond. Rather, she just climbed below.
"Hi! I'm Jennifer." She extended her hand. She gripped my hand firmly and I replied "Hi, Jennifer. I'm Sailor. I'm drinking scotch. What may I pour for you?"
"Scotch is fine, thanks."
Jennifer was pushing 40. Although she had obvious but small breasts, she had a manly appearance about her. Short light brown hair, a square face with generous eyebrows, average eyes, and thin lips. She was on the husky side, broad shoulders, minimal boobs and no real shape to her body. She wasn't fat, per se; just very solid. When I handed her drink to her, I noticed that her hands looked masculine. I began to wonder.
"Jennifer, make yourself comfortable, please. I'm a bit distracted at the moment after my day at sea. I need to find my wallet. Be patient with me, please."
"Oh, no worries, Mr. Sailor. I've got all night. You see, my parents own the marina, you know? I'm living with them while I get my life rearranged. I've enrolled in some classes and there's no school tomorrow."
I found my wallet and fished out a crisp new fifty dollar bill. "Here's a little something to acknowledge your after hours extra effort and to help you buy some school books. Thank you." I raised my glass and she did the same.
"Wow! Fifty dollars! Don't get tips like that very often, you know? I'll deposit this into what I call my rearrangement fund. Very much appreciated. This'll put me over ten thousand. More than half way there, you know?" She took a big swallow of her drink.
"Well, I'm glad that I could get your rearrangement fund, whatever that is, over the half way mark."
"Oh, my rearrangement fund is money I'm saving for my sex change operations. See, I was born female. Boobs and a vagina, you know? Yeah, and the biggest clit you've ever seen. But I've always felt like a man, you know? I think like a man, I act like a man, I have manly desires. Kind of difficult when your equipment isn't set up that way, you know? So I'm going to have some operations to, like, rearrange some things, you know?"
Wow. Good for her ... uh, him? I had been with crossdressers and shemales before. But never a woman wanting to become a man.
"Jennifer, good for you. I'm happy for you that you've found your true self. Are your parents supportive?"
"Oh, absolutely. They want what I want, you know? It's just the cost that scares them, you know? But they're solidly behind me in my decision."
"That's wonderful. I'm sure it's comforting to know that you have their support." I was dying to ask all the obvious personal questions but didn't think it was appropriate to pry. Those are personal, intimate things that she might want to keep private.
"It is comforting, especially after all the shit I went through in high school, you know?"
"Actually, Jennifer, no. I don't know. You mean shit about your appearance or dating or ... ?"
"Mostly the dating stuff, you know? See, I think and feel like a man. So I'm attracted to women, you know? Everyone thought I was a lesbian. When I'd ask a girl out, they'd always turn me down. They'd tell me to go bother Shirley or Tamika or Catherine. They were the known lesbians at school, you know? So I did. And once they found out that I really wasn't a lesbian, that I was a man trapped in this body, things got ugly, you know?"
"Gee, that must have been traumatic. I can't even imagine."
"You have no idea. It was ugly and traumatic then and it's ugly and traumatic now, you know? I don't have a normal sex life. Like, I just want to have a dick and fuck women with it, you know? But I don't. What I have is a clit the size of your little finger. Big enough for me to get myself off but not nearly big enough to use in a pussy, you know?
"I don't particularly like to give blow jobs and having my ass fucked is just okay, you know? I'm pretty good at giving a woman a decent head job but I've only had three tries at it. And having guys fuck my pussy is wretched, you know? I mean, I know or can imagine what it feels like for them so I let them do it. But I don't get any real pleasure out of it myself, you know? Having someone do cunnilingus on me is okay but it's really only my clit that stimulates me, you know?"
"Yikes! That's a different take on things from my perspective. Since you've been so open and honest with me, Jennifer, I'll reciprocate. As I was motoring in this evening, all that I had on my mind was having a stiff drink and getting a blowjob. I've got the stiff drink but it doesn't look like I'll get a blowjob."
Jennifer sat silent. She finished her drink and asked for a refill. As I stood and moved past her, her eyes focused on my crotch and followed it as I squeezed past her. On my return it was the same thing.
After I sat down, Jennifer bowed her head, looking at her lap and appeared to be having an internal dialogue with herself. She'd shake her head side-to-side and mutter "no, no". Then she'd tilt her head and mutter "well, maybe". Then a side-to-side shake and "def no". Finally she looked up at me. She took a big swig of her drink.
"As you can see, intimacy is difficult for me." She took another big gulp of scotch. "I'm uber horny right now and this liquor is like pouring gas on the fire, you know? If I had the perfect partner right now, what I'd want is to eat her pussy and have her suck my clit. Maybe let me play with her ass. But you're not a woman. I'm having trouble with this."
I didn't say anything right away. I let her mind settle. Then I offered "I have a suggestion, Jennifer. I'm pretty experienced with clits. I'll take your clit to places it's never been before, but only if you let me fuck either your pussy or your ass or maybe both. I'll keep my dick away from your mouth, but I'm gonna need it to go in at least one of your bottom holes."
Jennifer looked at me. Her expression was happiness, relief, anticipation. "Well, okay, I guess. I like the part about my clit. I like that a lot, you know? And I can put up with the pussy fuck, I guess. But I'm not sold on the ass fuck, you know? It depends, okay?"
"Time to pull those pants down, Jennifer. Spread those legs for me. Let me wrestle with your jumbo clit."
When I crawled between her spread legs, I first noticed how much hair covered her crotch. It was an over abundance of thick, curly pubic hair. More than I had ever seen before. Since my sole job was to service her clit, I dispensed with the foreplay kissing, nibbling and licking. I used both hands to pull the massive jungle of thick hair apart.
Underneath I found a rather small vaginal slit with no inner labia showing. What I did notice, however, was a pink button sticking out from the top of her slit. When I spread her pussy lips open, there it was. She had said that it was the size of a little finger. That was a gross understatement.
Her clit was easily three inches long. And thick ... oh, my God. It really was a micro-dick. I started by licking it from the bottom. I licked from the base upwards and on both sides. Then I opened my mouth and, without touching her clit, got my lips to it's base. Only then did I close my lips around it and put my tongue on the underside. I acted like I was giving a blowjob to a guy with a tiny dick. I stroked my mouth up and down on it, swirling my tongue around it. I sucked the whole thing hard into my mouth, then gently nipped the top with my teeth. She jerked and let out a gasp.
"Holy fuck, man. Do that again. I want more of what you're doing, you know? Do some more."
I continued to stroke my lips up and down this giant clit. I closed my teeth on it at the base, gently, then scraped my teeth up it's entire length. Jennifer was twitching her hips and making soft moaning sounds. I used my tongue to flick it, then swirled it all around.
After an eternity of using my mouth, I began jacking it off with my fingers. I stroked up and down, occasionally putting my lips on it's tip. All the while Jennifer was bucking her hips, like she was trying to fuck a pussy. She moaned and groaned. She'd spout off the occasional "oh, yes ... okay now ... yes, like that ... more, more, more."
I put my mouth back on it and bobbed my head, going faster and harder with each stroke. My lips would alternately tighten and loosen on it. I was having fun and Jennifer was making sounds like she was enjoying herself, too.
In the end though, it was my tongue that got her to orgasm. My tongue was over active twiddling it, playing ping-pong with it, and stroking it top to bottom and back up again. After what seemed like hours of sucking on this mammoth clit, Jennifer finally let loose. She grabbed the back of my head holding it firmly to her groin, bucked her hips wildly fucking my mouth with her rigid mini-dick. She screamed out "Goddamn YES ... YES ... oh there it is ... fucking A ... YESSSS!"
I got up, leaving Jennifer to recover. I refilled my drink and sat on the settee watching this poor tortured soul as she lay on my bed. "Well, how'd I do, Jennifer? Did you get any pleasure out of that head job?"
"Oh, plenty, Mr. Sailor. Plenty. Nobody's even seen my clit in over nine months, you know? That was long overdue and very much appreciated. Thank you."
"It was my pleasure, Jennifer. Have you wrapped your head around having me fuck your pussy yet? Just tell me when you're ready."
"Any time, Mr. Sailor. But don't be disappointed if I just lay there though. And pay no attention if I have my hand in there playing with my clit, you know? It's about the only way I get any pleasure when I get my pussy fucked."
I climbed between her legs, kneeling upright as I examined her incredibly thick bush and stroked my cock up hard. I mounted her with my dick in my hand. It was a bit awkward trying to part her thick pubic hair by swiping my cock up and down. Eventually it found her slit. With some effort I was able to part her thin pussy lips and my cock forced it's way in.
As my thick dick entered her vagina, she let out a loud gasp and her hips wiggled. "You okay? Am I hurting you?"
"No, no. Keep going. It's just been a long time since anythings been in there. And you're pretty big, you know? She'll get used to it. Keep going."
I was surprised how small her vagina was. It took great effort to push him inside her but the benefit was that it made for a really tight fit. Each push with my hips only gained about a half inch.
I continued to push my cock into her constricted vagina, feeling and enjoying the warmth and tightness. I finally got most of him in as I picked up speed. It almost felt like a teenagers cunt but it wasn't sloppy or wet and it never relaxed and opened up. And Jennifer was just lying there, her head turned to one side, eyes closed. I could have been fucking a blowup doll.
I pumped him in and out eventually getting him all the way in, balls deep. Since I knew that she would rather not have a dick inside her, I just wanted to thrash around, dump a cum load and be done with it. So I did just that. I closed my eyes and conjured up mental images of the women I had fucked who had really tight cunts. There were several and I scrolled through them mentally as I fucked this woman/man.
In an effort to find my release I started pounding hard. The harder I pounded, the faster I went. It became almost like a challenge, almost like a job.
The mental images of the beauties with tight twats coupled with the feelings of constriction on my shaft soon succumbed to the forces of nature and emotion. I had a satisfactory yet not very gratifying orgasm as I unloaded. Three moderate spasms was all my dick could offer this time.