More Island Slut

It was also during the time on St. Croix that I had the chance to take one of the largest white cocks ever. It wasn’t that he was that long, he was thick, good god was he thick!

Let’s just call this story

‘Island Slut, Next Chapter’
Bobbie gets well ‘bored’

I had my pick of nice big black ones all of the time, not all ‘monsters’ but way above average. The island was mostly black so, I had quickly made friends with the guys who could give me what I craved. The tourists were where I made my money and, most of them were endowed with your average white cock. Seven and eight inches of vanilla, with the occasional nine thrown in, as a welcome surprise. I could handle ‘average’ all night.
By the time this happened I’d been on the island long enough and, been schooled enough, by my girlfriends, that I knew how to operate without getting into trouble. I’d met ‘Sir Roger’ and decided I’d try being ‘kept’ for a while and see how that went. He was already spoiling the hell out of me.
Now I was TS about 90% of the time, loving it and getting laid often enough to have a bank account that I wasn’t ashamed of. I even had guys who came back for repeat ‘dates’ off and on.
My hair was maintained in a shorter ‘shag’ cut of the time, I was drinking less, watching my figure and, had nicer clothes. Like the girls, I dressed anything but slutty. We had even agreed on fixed rate prices – I was allowed to set some of my own for the ‘trades’ I was given – and, we had a little slush-fund in case anyone needed help with troubles. We were getting a little organized and, it made life easier.

By then I had a job in a small bar and, was running the charter boat on the side. I covered the shift from four pm to ten pm, which left me time to handle any guys I would be lucky enough to pick up. The girlfriends also made sure that I was still introduced to anyone they didn’t want to mess with. Rougher tricks, overly long or thicker ones and, anyone into BDSM. It still amazes me how many of them showed up on the island wanting to put someone over their knee.

‘Big Ben’ was one of them – that guy was hung!

Molly told me about him one evening adding, “I won’t even bring him around if you’re not interested baby. The guy’s hung like a salami, gets hard as steel and, likes to fuck deep and hard. Look, my cunt’s still sore, he wanted my ass real bad and, was hittin’ the shit out of bottom in my poor pussy!”
That got me breathing hard.
“He doesn’t have a problem with money at all, shoot honey, he offered me two fifty to stretch my little black ass!”

Molly could take a lot so, that made me curious as hell. I didn’t want ruined because that was a big part of my income. The last thing I wanted was a ruined cunt but…a big white cock…hell, a big cock of any color had me going. I told her that I’d be interested in at least meeting him. “Good,” she said with a typical smart-assed smirk, “better you than me honey!”
She told me that he was staying at the King Christian Hotel, we could stop by when I got off work, have a drink and meet him. I liked that better than picking him up where I was working, I was doing enough of that on my own and didn’t want to get in trouble over it. Most of the owners didn’t mind as long as you didn’t act like a common whore about it. I was doing pretty good there, the owner and employees didn’t mind having a trans waitress working and, I wanted to keep it that way.

That night turned out to be a slow one, I made everyone happy by turning over my meager tips – they could split them up – and, asking the boss if I could leave early. That didn’t bother him one bit. By eight I had enough time to go home, get a quick douche, a shower and change clothes for the introduction. By ten, I was all cleaned-out, cleaned-up and looking for them on the veranda of the hotel. I didn’t have to look long, it was slow there too, Molly and my date were the only ones there. The bartender knew us well – he really knew both of us in a carnal way – so my drink appeared as if by magic almost as soon as my little ass hit the chair.

James was a good guy, jet black and a real stud in bed. As he bent to sit my drink down, I reached to caress his ass and cooed a nice ‘thank you sweetie’. I’d paid my bar tab, in bed under him, a few times, limping away a few hours later with a raw gaping cunt and, leaking a lot of black seed. He tolerated us because we behaved ourselves and brought business to the hotel – one way or the other. James was no joke. He was handsome, from Haiti, over six feet tall and chiseled out of dark mahogany. Mom Nature didn’t slow down there; she’d ordained him with a real man-sized cock. James packed at least eleven thick inches of solid black lumber and, honey, he could get as hard as a tree at the drop of a pair of panties!
My comment got me a smile and a peck on the cheek.

Molly introduced me to Ben and filled him in a little before backing out to watch. I’d watched him as I walked to the table and sat down; I’d been given an appraising look. I was pretty sure he’d undressed me on the way over – at least his eyes had pulled my panties down and, sized up my ass. We all knew why we were there so there was no need to dance around anything, I just blurted it out, “So, Molly says that you’re very well hung and, wouldn’t mind taking a ‘girl’ like me to bed for some fun?”
Ben laughed than nodded, “I like that…right to the point…she told me you’re a frisky little thing and, you like bigger ‘equipment’ and, don’t mind a little rough and tumble in bed?” I’d been called a lot of things but ‘frisky’ hadn’t been one of them, not yet anyway.

Roger and I were a ‘thing’ then, but not in the financial sense…yet. He’d gone back to England for a month, he knew I couldn’t keep my legs together for long and, I’d spread them for some fast easy cash. He knew I’d be having some dates but, I didn’t want him to arrive and find me out of commission for him. Ben was going to open me up good but, I had to be careful.

We didn’t really talk business but, I found out, within a few minutes, that Ben was a Brit and talked in centimeters. I was informed that he was ‘only’ about twenty-two centimeters in length but his girth was five plus. Even in my cock filled brain that translated to big…damned big! It was the ‘five plus’ that I wondered about, that would leave me sore for a while, even if he took it real easy on my cunt! Of course, that was why good old Molly was willing to trade him off on me…damn! When I glanced at her, I was given a knowing wink and a flash of a smile; under the table, her foot was rubbing my leg a little.

Reaching across the small table he said, “I know I’m bigger than most…I know that I can cause pain with some, I’m willing and, am happy, to pay the right ‘girl’ what it’s worth.”
Kinda’ like added worker’s compensation built right in with the trick/date price.

He squeezed my hand a little and, gave me a kind smile. I liked this guy. He was probably mid-forties, good build, sort of handsome and seemed relaxed about everything.
I asked if he minded me having another drink – I needed some courage.
“Not at all dear, it’s on me anyway.”
I motioned to James as he said, “Let me get another round for us.”
He also mentioned that he had more in the room and, “we can send down to the bar for anything you may want or need tonight.”
When James brought the drinks he told him, “Please send a bottle of good gin to my room, some tonic and limes?” I was on gin and tonic that night.

We did have a very nice chat while I poured a little courage into myself. I’d eaten a little but not enough; two quick drinks and I was feeling the effects of the alcohol…a third and I was getting mellow…the fourth one had the effect of slapping me in the bottom and, telling me to stop if I was gonna’ satisfy this date at all! I sipped slowly and, finding a break in the conversation said – while nudging Molly in the calf, “I think it’s time for us to check…see if the things have been delivered to the room?” good old Molly chimed in with, “Oh god, and, I’m being so rude, I should go anyway and, leave you two thrill seekers to the night…I’m sure you can find ‘something’ fun to do without me!”

She literally jumped out of her chair, gave me a little peck on the cheek, whispered, “Good luck baby” and, almost ran away. The girl had quite a wiggle in that cute black butt and, I watched Ben, as he watched her wiggle away. Now I felt a little nervous, as the butterflies in my stomach got airborne. I shifted in my chair, crossed and re-crossed my legs…my bra was suddenly too tight and the panties were wedged in the crack of my ass…

I decided to get up, go around the little table and sit beside Ben; there was no one on the veranda but us. I took a deep breath then, made the move. I used all of my body language, as I sat, to let him know that I was ready to do something. It helped to put my one hand on his closest thigh and rub in an upward direction. Ben moved closer and offered, “Why don’t we finish our drinks and go up to the room?” When he put his hand on mine I told him that it sounded like a good idea then, turning to face me more, looked me over and said, “You know, when you first walked up I thought you were a girl for sure.” It was pure flattery but, what the hell, I thanked him for the nice compliment. When he moved my hand to his crotch, I gave a little gasp of shock then, made a thoughtful little noise. He was indeed aroused and had a massive bulge there. I worked my hand around to give a little squeeze and, was rewarded by a gasp of his. Damn did he have a cock!

In the room I sat on the bed while he made a drink for both of us then sat beside me. The big French doors were open to the night air, the curtains were wide open to the balcony and there was a nice little breeze. The only light in the room was coming from the streetlights so it was a nice dim glow. When he looked like he was going to make a move to kiss me, I sat my drink on the bedside table, uncrossed my legs while turning more in his direction and said, “Now, that might be easier for us.”
When our lips met, I closed my eyes. I parted my lips a little as his one hand went to the back of my head, the other found bare thigh and started caressing upward slowly. When we started to devour each other I spread my legs slightly, his hand finished the trip and, he moaned around the kiss. I sucked some air in through my nose, relaxed more, spread my legs more and got his tongue between my teeth – but I didn’t bite. That was about the time his fingers started to feel around between my legs. While he moaned again, he pushed me down on the bed…we were both ready…I went to work on his belt and the front of his slacks. Suddenly there was no doubt that he was ready! My fingers were around a throbbing, rock hard and, very thick cock!

It had been my experience that, most really big guys don’t get rock hard. They get nice and firm, hard enough to handle penetration but, not like rock solid. For someone like me, taking it – something very large – in my rectum/cunt, means that there’s some flexibility. It’s not like taking a baseball bat, a big cucumber or anything solid. There’s some ‘give’ in the meat. When a guy’s rock hard, like a few black guys

He was every bit as thick as the first big black one I’d had at the YMCA in San Diego…just not as long. In nothing flat, my panties were down then off as my skirt was pushed up around my waist and a finger started to probe my cunt a little. I excused myself long enough to get the lube out of my purse and use some then, set it on the bed within reach.

I was gonna’ need it, a lot of it!

I pumped his cock a little more while he kissed me and continued to use his finger(s) back there – I also made access as easy as possible for him. Damn, it was getting hot in that room – wiggling around then reaching back I tried to undo my bra. Ben took the cue and, with one hand and a few deft fingers, had it undone. I allowed him to guide me into the missionary position then pulled my legs up and spread for him like a good slut should.
For taking him, the missionary position is always the best. I found out about this early in life; the bigger a guy is it’s best position – and you can take more of him – using missionary or doggie style. I’ve always favored it because it seemed more intimate. I adore being kissed during sex and, he’d shown a desire to kiss me. I wanted more of that and all of his cock; even though I was now trembling in the anticipation of the coming pain of penetration.

Smiling down at me, he assured me that he’d take it easy ‘at first’. I was counting on that, I hadn’t been stretched this far in a long time and this cock was a real monster!

I got my hands behind my knees and pulled my legs up more while rolling my hips back as much as I could then, tried to keep breathing evenly and deep as he positioned the head at the entrance of my well lubed little cunt.
He eased down and in a little slipping the head in, I started to strain like I was having a BM and, arched my back a little as he pushed more. The head wasn’t bad but there was sudden sharp pain as the shaft followed, then more pain as I took the first few inches and my sphincter was f***ed open. It was like being an anal virgin all over again! He kept a steady pressure on and gave it to me slowly at first, easing in deeper and deeper – I kept straining to take it – squealed past the lip I was biting and tried to deal with the hot raw pain I felt. I was also dealing with some really bad cramps…gut twisting ones!
Knowing that there was nothing in there but air I strained, tried to relax my muscles as much as possible and, allowed the little puffs of air to escape around his cock. Like Tupperware, it was a damned tight seal!

The pain wasn’t exactly blinding but it was close, hot and raw. I kept squealing like a little cunt, straining like crazy and let the spots I was seeing, along with the fireworks, explode in my eyes. He made the comment that, “My god you’re tight as hell.” when I’d taken about half of him. I wouldn’t be tight for long; I was gonna’ be gaping like hell when he was finished!

Suddenly he was in all the way, our bodies made contact and I could feel his balls settle against my cheeks. He touched bottom at about the same time, with a little nudge that gave me another moment of discomfort. By then I was panting like hell, still squealing when I could get my breath and my eyes were tearing up like crazy. I had all of him, every centimeter of him, buried to the hilt in my little ass. He waited, while I worked my little ring of muscle around his cock, let me relax and allowed time for everything to relax and stretch back there then withdrew with a smile. When he did that, it felt like everything inside of me was being sucked out! I stopped straining and relaxed as he withdrew slowly until only the head was still inside. I do remember thinking that, there should be more than enough lube, he was just huge.

I panted away, squealed even more – and a little louder – as he pushed back in. With my eyes closed, I was treated to one hell of a fireworks display and, more cramps, as he filled me again. My little cunt screamed in pain, I kept straining all over again and then, just let it all out in one long muffled scream of pain. I dug my nails into his arms, which is where my hands ended up and let him fill me again. It wasn’t as bad as the first penetration but it was still painful as hell. One he was buried to the hilt again, he stopped, eased down and kissed me good and hard. That kiss became a good sloppy one.

I wasn’t crying but the hot raw pain had me tearing like hell. With everything else, I tried to remind myself to relax more, slow down the panting and, just take deep even breaths. Nice long even ones, filling my lungs.

With my legs up, under his armpits, I locked them around him, gripped his forearms good and tight and hung on. Ben withdrew again then, started back in – this time a little harder – until his balls slapped against me again. There were still cramps and yes, the pain was still very real! He was being very nice to me, taking it very slow and, I appreciated that. Even as tight as I was, after being well stretched, the raw pain was there…becoming a little subdued, as it went on, but still there. At times like this you also become aware, as the pain subsides to a lower level, of being rubbed inside good and hard on every stroke of that cock. It intensifies the feeling of sex. For me, there was no thought of pleasure, there would be no orgasm to release anything. I would have the thrill of satisfying him…the knowing pleasure of taking him and, making him happy.

When he got close to cumming he stopped, gave me a big kiss and asked, “Do you mind if I go a little faster, I’m about to cum and I’d like to get there.” I agreed to it quickly, I needed a break and, could handle a few minutes of pain to get there. My cunt was a little circle of burning pain, I was cramping again and, I was about ready to start screaming. I thought the best thing to do was, just let it all out and get it over with!

It took maybe a minute. It was just about the hardest, the most painful fucking minute ever. He withdrew and started fucking fast and hard – not to mention deep! I put my hands over my mouth and literally screamed into them as he went at me. Then, with a sudden deep groan, he drove himself in to the hilt again, stayed buried and, blew one hell of a load!

He didn’t even start to go soft but, he did pull out slowly.

In the last few minutes he’d almost fucked me off of the bed.

I was gathered into his arms to be held and kissed as we caught our breath. I could clearly feel my little cunt gaping wide open, it was still raw and burning. I’d taken him, I’d satisfied him, that was the important thing. I was also aware that I was dripping. His cock had filled me so much that he’d ‘milked’ me. I wondered to myself if this was it or, if he’d want round two, would he get it up again and take me or was this the end of the evening.

We relaxed a little and played for a while. He was interested in me and, was concerned about how much the sex had hurt me. I was doing a favor for a friend and assured him that I’d recover. There was a little more drinking and, in due time, most of the pain went away. There was still some discomfort but I told him that, since my job was satisfaction, I didn’t mind more. I just asked him to please, be just as gentle.

There was more.

I ended up spending the night. By the time he took me again, I was beyond moving, really gaping and very sore. That one had taken a while; I took a few aspirin, a quick shower and, then just cuddled until we drifted off to sl**p.

In the morning, when morning wood came up, I was given a choice. I used up all of my remaining lube to make it as easy as possible…it helped a little. It also helped that I was still pretty loose. The bed was a wreck anyway, I’d leaked a lot of cum while sl**ping. I took a quick pee then hopped back in bed to be well skewered all over again. That one was long and became very loud!
We changed positions a few times but, in the end, I found myself back in the good old missionary position while he fucked away hard and fast. I screamed and wiggled my way through it. The age-old problem with morning wood is that, it takes forever for the guy to get off…I really paid for taking that one!

He cared enough to make it worthwhile. Although he did leave early, for a golf game, I found an envelope with my name on it and $300 inside.

I dressed, powdered my nose and stumbled down to meet the girls for breakfast. There had been a note saying that he’d be very interested in a dinner ‘date’ for tonight…I was taking the rest of the day off.

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