I had been banished. My wife would be joining me in a couple of months, but I was sent ahead – banished from New York – for my transgressions. April’s father had known I was bi before he bought me for her daughter – and he also knew how I made my living, because he had been paying April’s bills. But I suppose he assumed I would put all of that behind me when we were married. Look as I could, though, I couldn’t find that clause in the prenuptial agreement. And the prenup had been voluminous, I can tell you.
I think he was surprised that April still wanted me after what happened in New York. But I was better looking and smarter than she was, so I guess she still considered me something she wanted on her arm and pulling her chair from the table for her and carrying her handbag on command, and smiling dreamily at her whenever and forever when she wanted to impress someone. She also considered me the perfect fit. The small, forever-young couple. She was barely five foot, and I came in only at five-four, and just as she would forever look like a teenager, I was likely to look barely nineteen and not yet having my age spurt well into my thirties. We both must have been graced with Fountain of Youth genes. In my case, women and men were willing to pay extra for the sensation that they were plucking the baby from the cradle for the first time. And I was good at making it seem to be the first time.
April must have also liked the first-time sensation, as she wasn’t willing to let me go no matter what her father had caught me doing. That being the case, there wasn’t much else Fred could do but get us out of town for a while – mainly me. He couldn’t make too big of a stink about it. The guy who was fucking me and had bought me that Jaguar was farther up the feeding chain at Vado U.S. Pharmaceuticals than Fred was.
The pharmaceutical company president had been sniffing around me even before I met April. Indeed, it was at a party of his that I had first met Fred’s daughter. The company president liked to role play. He paid ahead and I was sent to perch on a seat in the bar of a fancy Manhattan hotel until he showed up and sat down the bar from me and acted like each time was the first time. He’d notice me – for the first time – and would start with sending a drink my way and then making eye contact when I looked around to see who my benefactor was. And then the dance of seduction, as he conveyed in his eyes what he wanted and I pretended not to understand at first and then to blush. Sometimes he took it so slow that I had to politely ward off another suitor before the Vado U.S. president got around to sliding into the seat beside me and whispering what he wanted in my ear and how much he was willing to pay – which was above what the escort service was charging him so there was always a generous tip in it for me.
I would pretend that I wasn’t ‘that sort’ of person, but he would wear me down with sweet talk. I’d tell him he was handsome – which he wasn’t; he was ugly as sin and slightly overweight, but he had a cock to die for – a girth that even I could feel, because, although I was slight of stature – while being quite well-muscled proportionately – I had developed a hole and channel that could take a military missile upon demand. Few men singularly tested that hole, so I usually had to put on a good act while being taken. But with the pharmaceutical company president I didn’t have to pretend my channel was being taxed.
When I had demurely given in to his seduction, he took me for a ride around the city in the back of his limousine. I would strip down to the red brassiere and sheer panties he had specified beforehand as soon as we entered the backseat and the limo door clicked shut – while he stripped off his trousers and briefs as well, and, as always, I gasped at the size of him and gave a low moan. I would have done this for the client anyway, but in his case each time it was a revelation.
He would lean over and wrap an arm around my shoulder to hold me tight and, with a tube of ruby-red lipstick, he’d generously slather my lips. Then I went down on my knees between his spread legs and left as much of the red from the lipstick covering his cock while, jaws unhinged, I gave him a languid blow job – to the point where he was ready to explode. And then he’d lift my small body up from the floor of the car, rip at the sheer panties until they gave way, and take me into his lap – always facing away from him – and slowly lower my channel on his blunderbuss of a dick. He would come almost immediately, but then he held me there, his hands covering my nipples underneath the cups of the bra, and I would rise and fall on his cock while he murmured the name of some woman in the small of my back until I brought him back to life for a second coming.
Sometime thereafter – when we had both readjusted our clothing, I was delivered back to the hotel where he had ‘met’ me. Each encounter started at a different hotel.
As time went on and he got bored with this, he wanted to do it right there in the hotel bar lounges. I’d meet him at the bar and we’d go through the preliminary ritual but rather than going somewhere in his limousine, he’d guide me to an already-booked table back in the shadows of the lounge and I’d go under the table and suck him off while bar life went on around us. Then there were the nights he’d call me on the telephone and I had to make him get off just by talking to him over the telephone.
The first time I met April was at an office Christmas party the Vado U.S. president held in his lavish Manhattan penthouse. I had been hired for the little party he was having afterward for a few very select male friends. The earlier segment of the party was all noise and clinking glasses and women checking out what other women had worn, and talk of the Hamptons and Paris in the spring.
I had gone out to the terrace because I found the crowd oppressive, when a young woman, smaller than I was, which was a surprise, came up beside me where I was standing at the railing and looking down into the bustling world of the city.
‘I can’t take the crowd, either,’ she said. She bordered on pretty, but only because she had the best of help money could buy to make her so. Her body was in good shape, though.
‘Excuse me?’ I said.
‘You came out because you found all of that oppressive. Bulky people towering over you and pushing you underfoot. Or did I misjudge?’
‘No. That’s right, I guess. Right on, actually.’
‘Same with me. I feel like I’m going to be swallowed up. It will improve within a half hour. Most of them just came to check in and mark off their presence. This is an office party. The room will thin out soon. Do you work for Vado U.S.?’
I honestly was able to say yes, as the Vado U.S. president had put me on the payroll. I had no idea which branch I supposedly worked in or what my job supposedly was there – but I did have an office. As far as I could tell, though, I only had an office to give the president a break in his day. It would start with either phone or cyber sex – him contacting me in my office. My job – my only job for the company as far as I could determine – was to get him so worked up over the phone or on the Internet that he’d either show up in my office for a fuck or summon me to his office.
‘I don’t,’ April said. ‘My dad does. Fred. Fred Tipton. He’s one of the national vice presidents.’
She could see that this made no impression on me, which actually seemed to please her.
‘Say, I have an extra ticket for the theater after this and no one to go with. I don’t remember the name of the play, but if – ‘
‘Sorry. I’m booked tonight. And – ‘
‘Booked?’ she asked. ‘That’s a rather strange way to talk about a date or appointment.’
‘I’m a male escort. I do it for the money. Booked is how we phrase it.’ She was a nice little piece, but I saw no reason to be coy about it.
‘Oh, I see,’ she said in a halting voice. There were several moments of silence as we both watched the sun going down over the New York skyline and tuned our ears to the volume level of the party beginning to wind down inside. At length though, she asked in a small voice, ‘And what do you do as an escort?’
‘Anything the client wants – as long as they have the money to pay for it,’ I said.
‘Do you have a card you can give me?’
And thus it started with April.
Later, after all of the guests, including April, had gone other than a half dozen older, obviously well-heeled men, the Vado U.S. president suggested that it was time that we withdrew to the billiards room for some more serious partying. The room was a large interior one, with a huge skylight. There was a bar at one end of the room, complete with bartender, a blond hunk who gave me the eye as soon as we entered. The carpeting was some sort of wild paisley print, the walls were lined with low bookcases, with pool cue racks on the walls relieved by blown up and framed black and white Mapplethorpe art photographs of young nude men in various provocative poses. Two pool tables were well spaced in the center of the room. There were club chairs around a large, square coffee table off to one side, where the men first sat as cigars were offered around. I wasn’t offered a cigar – and neither was the bartender.
The bartender was told to put some music on, and I was told to dance on the coffee table and slowly strip as the six men, all in tuxedos, and all with their flies open, their cocks out, and their hands busy, sat around and watched me slow dance and strip. The bra and panties I was wearing were black and lacey. When I was down to those, the Vado U.S. president told me to lie on my back on the table in front of him and spread my black-silk-stocking clad legs. He leaned over into me and ripped the crotch of the black panties open and slowly fucked me with the moistened end of his cigar while, at his invitation, the two men on either side of him each slowly rolled the stockings off my legs and licked my feet and sucked on my toes.
When the pharmaceutical company president became bored with this – and sufficiently aroused – he lifted me off the table, turned me, and set me down on his cock. I fucked myself on his cock, rising and lowering my channel by leveraging the balls of my now-bare feet off the thick paisley carpet, as the other men sat, bug eyed and hands busy with their cigars and their own cocks, and watched the Vado U.S. president get off.
Shortly thereafter, the room now in a blue haze of cigar smoke, I found out that one of the pool tables was for me and the other ones was for those guests of the company president who took breaks between fucking me on the pool table to play billiards on the other table. To the titillation of his guests, the company president had initiated my gangbang taking on the pool table by mining my channel with the end of a pool cue.
I thought maybe the guys had overdone it with the smoke late in the evening when a door was flung open and a couple of burly firemen stormed it – but it turned out only to be the company president’s idea of a perfect ending to the evening. The firemen did a strip of the president’s guests and then serviced or were serviced at the guest’s option as the company president sat and puffed on his cigar and grinned.
I went home that night with the blond hunk of a bartender – having said I’d be happy to give him a massage after his tough day when he complained about how tough bartending was. At his apartment he got his massage, but this worked its way in my earning all of the tip money he’d made that evening by accommodating his interest in mammoth cock dildos and a change of progressively larger butt balls. Like most before him, he was amazed and aroused by how much the channel of someone with such a small stature could take.
After that evening of fetish debauchery and meeting April, she engaged my services often. She got some great tickets to events and she turned out to be a pleasant, undemanding, straightforward fuck.
But I was more into what the Vado U.S. president devised and was willing to pay for. Our liaisons continued after April’s father had bought me for her and we were married – and after I was given an actual job title in the pharmaceutical company office, but, thankfully, not with any additional job responsibilities to speak of – other than to have the right wardrobe in a lower desk drawer, to always be ready to perform on the telephone or Internet, to be prepared to work late evening on demand, and to know how to get to the back staircase up to the company president’s office – except when he decided to slum and take me on the desk in my own office.
It was here one evening that Fred Tipton walked into the president’s office unexpected and unannounced and found me in a silky slip, lying on my back on the company president’s desk, with him standing between my legs and holding one stockinged leg up with a hand, while he was using the other one to help guide his dick deeper into my channel. Tipton hadn’t said anything; he’d just turned and walked back out of the office. I don’t think the company president even knew he’d been there. But I saw him. And I heard from him the next morning. But there wasn’t much else he could do – other than arrange my transfer to the Puerto Rico office – which is what he did. And he wrote a large enough check, that I didn’t balk. I have no idea when the Vado U.S. president heard I was no longer in the New York office – or if he made any attempt to learn where I had gone.
It would have been OK with me if April had dumped me. The prenup gave me a good bonus regardless. And the ‘bigger company president’ was ready to take me in – or so he’d said. Of course, no one ever knows such things for sure until they are tested, does one? And he was bigger in every way that meant anything to me just then – a bigger bank account and a really big dick – and he knew what to do with both. I liked April well enough, though, so marriage to her had suited me fine too. I had said yes to April’s proposal because I knew I only had a few more good years. A male escort in New York – one available to either sex – only had eight or nine good years. By the time we hit thirty, we’re really only good for the women. And that’s not my style. I’d already found out that it was men who liked the thought of taking a smaller, underage-looking man more than women did. That was where the big money was.
Getting banished to Puerto Rico was enough to give me second thoughts on the march of time and my future prospects and made me willing to consider going cold turkey on men altogether. If that’s what it would take to be able to continue to live the comfortable lifestyle I had.
And that’s why I found myself in San Juan as third vice president of the Vado U.S. office there.
* * * *
My banishment to Puerto Rico all happened so fast – too fast for the office branch in San Juan too. They didn’t have any place to put me when I arrived from New York. And my position was so important that they refused to let me in the company branch until they had carved out a suitable office space.
So, the very day I arrived, the president of the Vado U.S. San Juan branch came to my hotel, all apologetic, and handed me a nice check and suggested that I disappear for a week and arrive all over again when they were prepared to give me a proper welcome.
There was no embarrassment over the check. I was used to being taken care of. There was slight embarrassment that he didn’t seem to want any services for what he was giving. He was British, maybe in his late fifties, all tanned and lean and a full head of white hair. He’d come in his tennis togs and he moved around the room on the pads of his feet like a conditioned athletic. I found him attractive. I found older men more attractive than younger, as long as they were in good shape – powerful men both in presence and stamina. And experienced men. I liked to learn new tricks, to experience the unusual things that turned experienced men on – their fetishes. So, normally I wouldn’t mind taking this man on for a couple of rounds – especially as he was handing out checks.
But he made no suggestions – didn’t make a move. And I would have bet that he knew exactly why I had been sent down there so quick-quick. I was prepared to try out my new-found determination to save it all for April – or at least for a woman. But he didn’t test my resolve. For some reason I felt deflated. I wouldn’t have done it really. But I would have liked for it to be my choice not to have done it.
I cashed the check and consulted the concierge at the El San Juan Hotel on where someone could disappear on the island for a quiet, but pampered week of incognito. He suggested a small resort hotel high in the hills above the city, and within hours I was being taken in a hotel car up into the mountains.
The hotel car left me at the entrance of the Sao Paulo resort, and roared right off again, with the instruction to come back and pick me up in exactly a week. It had all happened so fast that I didn’t even have any contact numbers with me down in the capital.
I was all alone – and out of sight and mind – for a week.
I did a three-sixty at the entrance, taking in both how beautiful it was, with its lush vegetation and its view, from the entrance down into San Juan and out into the surrounding Caribbean. Surprisingly the hotel seemed deserted. There wasn’t a soul around – not even a porter to carry my bags in. So, I hefted them up myself and sauntered into the entrance and up to the reception desk.
The hotel was plush inside, but, as I had found outside, it was deserted. There was no one at the reception desk even. I put my suitcases down and did a circuit of the entry lounge. At the other side of a two-story open space, surrounded on three sides by a balcony, was a large expanse of glass overlooking one of those ‘disappearing pools,’ where the far rim of the pool was below the water level and spilled water down an escarpment into a recirculating basin, making the pool look like it was pouring its water on San Juan at the foot of the mountain.
As I passed by a stone-cold open fire pit in the center of the lounge, I heard the clinking of ice in a glass and looked under the balcony to my right to see that I wasn’t really alone. A bar was tucked under the balcony and a lone man was perched on a bar stool and was nursing a glass of liquor. He was a near twin of the Vado U.S. branch president down in San Juan. Well-muscled and trim but white-haired and maybe in his fifties. Movie-star handsome and deeply tanned. He was in shorts and stripped to the waist. His chest and arms and legs were nearly matted with curly salt-and-pepper-colored hair. I liked a man with fur. The gray was only slowly working its way down his body, and I immediately found myself wondering what color his pubes were. And if he were cut or uncut. I preferred the feel of an uncut cock inside me. And I preferred bareback, which was often possible with the class of men I serviced. They regularly got checkups and expected medical verification of any male escort they were assigned.
I surmised he was a European by his bearing, but more French or Italian than English was my guess.
He smiled at me and tipped his glass in my direction, and I just nodded and moved on, although I felt myself becoming aroused. I hadn’t been fucked by a man in almost two weeks and my resolve was beginning to crumble.
I went back to the desk, and after a minute or two, the man from the bar padded out and went behind the desk. He was very well muscled indeed. In great shape for his age.
‘Yes, may I help you?’ he asked. The smile he flashed me was all white teeth and interesting and it seemed interested. The accent was English. So much for my powers to discern one European from another. At least I had been able to gather that he wasn’t American. Just too suave and self-assured for that.
‘I’m checking in. The name is Cameron, Ty Cameron.’
‘I’m sorry, Mr. Cameron. The resort is closed. Renovations.’
‘Closed,’ I asked, in surprise. ‘But the concierge at the El San Juan Hotel down in the capital made reservations for me.’
‘Nevertheless we are closed. But this is Puerto Rico. We are laid back here. If you don’t mind being the only guest and are satisfied with the bare minimum of services – ‘
‘No, that would be fine. I was looking to be a recluse for a week.’
‘There are only the two of us here now – just Rollo and me. The workmen won’t show up again for more than a week. They should be here now, but I was informed they would not be coming today or tomorrow or the next day – but would do so in a week’s time. That is the way it is here in Puerto Rico. But we will be all right. Some of the rooms are finished with their refurbishing, and Rollo can do anything. Anything, really,’ he said, and the look he gave me seemed provocative for some reason. ‘And he’s a great cook. Alas, I am only the lazy, worthless owner.’
‘No that’s fine. It should be quite restful.’
‘In that case, if you will register, please, and hand over your passport – sorry we have to hold it for our guests. It’s the law here – I will go find Rollo and he will show you to your room.’
When I had finished signing my name, I turned, and standing there was a mountain of a many from the Caribbean islands. Coffee colored, smooth-skinned, dreadlocks, built like a champion body builder, and with a white-teethed smile that reviled the one the resort owner had flashed me. Like the other man, he was only wearing shorts – and flip flops. My guess was that he was a good ten years older than I was too. But he was a beautiful specimen of a man.
‘I am Rollo. If you are ready, I will take you to your room now.’
My internal response was that Rollo could take me anywhere, any way he wanted me. But then that resolve of mine to stay true to April entered my mind again, and I mentally said ‘down boy’ to my hardening cock.
‘And I am Paul. I named the resort after myself because I’m such a saint,’ the resort owner said – and he said it with a silly little grin on his face. ‘With only the three of us here, there is no reason not to be on intimate relations.’
I supposed he didn’t mean for that to sound as it did, but it gave me a lurch of arousal anyway.
As I followed Rollo up the stairs to the balcony, I watched his two bulbous butt cheeks roll and bounce against each other, and I was sure he wasn’t wearing any briefs.
He took me to a fine room overlooking the pool and San Juan below, with a four-poster bed and all done in white muslin. The bathroom was marble and the tub had room for all three of us – or at least that was my first thought. I’d had no intention of going into heat like this, but my best of intentions had always been a bit fleeting.
When he had set my bags down, handling them effortlessly like they were feather pillows, and had done the usual bell hop’s circumnavigation of the room opening curtains and showing me what worked what, he turned and smiled. ‘Is there anything else I can do for you . . . Ty . . . anything else at all?’
‘No not now, thanks,’ I said – even though it wasn’t what I wanted to say at all. I had noticed before that he was studded. He had a stud in his tongue I’d never seen before and I had no idea how he managed to eat with it. It was a small ball, but it was on a stem protruding from the center of his tongue – sticking out a half inch or more. And he had rings pierced at both of the nipples on his heavily muscled chest. I immediately found myself wondering if he had a cock stud or ring too – and, if so, how big – how well I could feel it if he fucked me.
I came back from the reverie in embarrassment and found that he was still standing there, expectant and smiling.
‘Oh, sorry,’ I said, and I started rummaging around in the pocket of my trousers for a tip.
‘No need for that, mon, thanks. We are on first-name basis here and the resort isn’t open. You may find another way to show any appreciation you have for me, assuming you still want to after you’ve tasted my cooking.’
Then he laughed and was gone.
It had been a long, dusty ride up the hill, so I immediately stripped and showered and then dried off with a giant-sized Egyptian-cotton towel and padded out to the king-sized four-poster bed and laid down. I went to sleep almost immediately. When I awoke, I was surprised to find I had been so tired I’d just laid down on the bed in the nude.
Then I realized that what had awakened me was the sound of sex. I rose from the bed and padded over to a set of the full-length French doors that served as the room’s windows and looked down into the pool area.
Rollo was on his back on the diving board and Paul was straddling the board with his legs and fucking Rollo in long strokes with a cock that dug forever. Rollo was in full arousal too, and his cock rivaled Paul’s. However, it was special, in that, in contrast to the milk chocolate of his body, his cock and balls were jet black. And, sure enough, there was an extra thick Prince Albert ring piercing the cock head.
I don’t know how long Paul had been fucking Rollo, but it went on for an impressively long time even after I started watching. I found I couldn’t pull my attention away from what was happening below my window, and it was only when Rollo looked up and surely smiled that I realized that I was in full view and was stroking myself. I withdrew in embarrassment of having been found playing the voyeur.
I remained in my room for the rest of the day – taking another nap after I had masturbated to the image of Paul fucking Rollo. Dinner was delicious that night. We ate by candlelight beside the pool, with Rollo joining Paul and me after he had cooked the meal. Both men were fully dressed now, but in light cotton that enhanced the sexiness of their bodies.
The conversation was pleasant, but neither alluded to what they had done that afternoon or what I had seen. Neither did either make any provocative moves toward me, which I found both disconcerting and arousing in itself. When I went back to my room that night, I stripped and, after my shower, laid on the bed. I assumed that either Paul or Rollo would visit me, and any resolve I might have had not to entertain either of them – or more provocatively – both at once, which was a fetish I myself enjoyed, was gone. And not just a threesome, but two cocks inside me at once, the three of us working as one for a shared orgasm. I didn’t know that I could recall taking two huge cocks like these men had at once, but, despite all the planning I had done on learning from my mistakes in New York, I ached for a trial of it with these two men.
But no one came that night.
By the morning, I was ripe for the taking – to the eventual enhanced arousal of all.
I woke with a rap on the door – alone in my bed – and found a breakfast tray waiting for me just outside the door. There was a card on the tray which said, ‘It’s a fine day; a great day for a visit to the pool.’ I had found a couple of fluffy pool towels under the breakfast tray.
After I’d eaten and showered and shaved, I rummaged around in my luggage for my Speedo and the novel I was reading, grabbed my sunglasses, slipped on the bathing suit, and descended the stairs into the empty lobby and walked out to the pool. Only one lounger was now beside the pool, up close to the diving board, so I opened one of the towels out on that and laid down.
Within minutes I saw Paul moving through the lobby and toward the pool. He was naked and he was magnificent. He came out onto the deck and climbed agilely onto the diving board, strode rapidly down the length of the board, and performed a perfect dive into the pool. He then proceeded to do laps at a fast pace.
I was watching him so closely that I barely noticed Rollo coming out to the pool as well. He too was naked, his ringed cock swaying rhythmically against his thighs as he strutted. He was holding a tray with a drink on it, which he set down on the small table beside my lounger. Then he stood over me, his cock swinging freely above my head.
‘I saw you yesterday. In the window,’ he said matter-of-factly. ‘You fuck men, no?’
‘Usually they fuck me,’ I answered.
‘I may make love to you, yes?’
‘Yes.’
‘I try to be careful,’ he assured me. ‘You’re so small and I am so big. I’ll try not to crush you and if you cannot take me when we get to that point, tell me. I do not want to split you.’
‘You’ll be surprised,’ I answered. ‘I can take you and Paul both – at once.’
His eyes lit up in arousal at that, and he licked his lips. And I could see his cock swelling even further too.
‘Ah, you are like a boy. So small and delicate – but perfect just perfect,’ he murmured. ‘Are you sure – ‘
‘Yes, I’m sure,’ I declared. And I could see him trembling with arousal and anticipation.
He moved to the bottom of the lounger and gently took my thighs in his beefy hands and pulled me down to where my butt was nearly even with the bottom ridge. Then he took the second towel I’d brought out, folded it to make it into a cushion, and laid it on the patio tiles at the base of the lounger and knelt on it. He reached up and pulled my Speedo down and off my legs with both hands. He cupped my buttocks and brought my hole to his mouth and started a long session of rimming my hole that not only opened me up nicely but had me moaning and begging for him.
‘You are so nice,’ he whispered. ‘Your body, it is small. But your cock. Such a nice size, and so long. Nice balls.’ He drew the latter into his mouth and started to hum and the resonation was driving me silly wild. He pulled away from them and his tongue went back to my rim.
‘Please, please fuck me,’ I moaned. But he ignored me as if I hadn’t asked for it.
‘Ah, yes, I see, it blossoms like a cavern. Rose Cavern,’ he muttered. And then he laughed, a deep, hoarse laugh. I raised my pelvis and put it into a slow rolling motion as he inserted first one, and then two, and then three fingers. We both sucked in our breath and moaned as I felt the knuckles of his hands at my rim on all sides, and I relaxed my channel, preparing for feeling his wrist there and the spreading of my channel deeper inside by the rest of his hand. But his hand wasn’t sufficiently greased and he was impatient for other pleasures, so he stopped with a grunt of ‘Later. Save for later.’
He withdrew his hand and his lips and tongue went back to rimming me. He sighed as I opened even more.
I hadn’t noticed when I’d laid down on the lounger, but now I saw, as he finished rimming me and looked up over my heaving belly with a smile that there were restraints at the four corners of the lounger.
Rollo pulled one of these up and showed it to me and said simply, ‘May I?’
‘Whatever you want. As long as you fuck me,’ I said in a hoarse whisper. ‘I want to feel that thick cock ring of yours inside me.’
‘Oh, I will. In more than one way. You like this toy of mine?’
I sighed a yes, and he rubbed his cock tantalizing along my inner thighs, running the warm metal along tender skin. I moaned and reached for him, wanting to draw him inside me there and then. But he laughed and pushed my hands away and took my wrists in a firm grip and started guiding them above my head. He did, however, move his cock head into position at my hole and give me the feel of the ring rubbing in circles around my entrance.
‘For now the restraints will be good,’ he said while I was hyperventilating at the feel of his cock at my entrance, wanting it to plunge inside me. ‘What I do now, it will be dangerous for you to move too wildly. And I think it will make you wild, yes.’
I didn’t know then what he meant. But I was melting at the prospect of whatever it was – and I soon found out.
He pulled my arms over my head until my wrists could be secured to the top corners of the lounger. And then he secured my ankles to the bottom corners.
I thought he would thrust that huge, ringed cock in my widened and pulsing hole then, but he didn’t. I saw his smile come up between my legs and his hands to my cock. His mouth opened, and I once again saw that gold ball thrusting out of his tongue on its stem. And then, as he closed his lips over my cock head, I found out what the tongue piercing was for.
The small ball searched out my piss slit, and then it was entering me there, the stem allowing it to bury itself nearly an inch inside my urethra. And then he was fucking my cock with his tongue stud. Pushing it in and pulling it out of my piss slit and pushing it in and pulling it out. And I was crying out and writhing and straining at my bounds, all the while trying to keep my pelvis steady for him. And coming again and again and again, as he let me briefly rest but then piss slit fucked me again. Until I had no more cum to give.
While this was going on, I looked over at the diving board and Paul was sitting there, watching us and stroking his own cock.
Only after I was exhausted and whimpering did Rollo stand and laugh and then enter me with his fat cock and punish my walls delightfully with that thick cock ring. Sliding in and out, giving me waves and waves of pleasure of thick metal rubbing across channel walls. He muttered in surprise when he entered me and felt my channel taking him tight, which was yet another secret I had learned in my business. He took me bareback, and when he came, he gushed deep inside me. I enjoyed Rollo immensely – and in the main because of the dance of fucking he did between my legs complete with the view of the undulation of his beefy muscles and the rhythmic swaying and tinkling music produced by his beaded dreadlocks.
He left me and exchanged places with Paul. Paul released the bounds on my wrists and ankles – but only long enough to turn me over on my belly. I was too weak and satiated to even think of putting up a struggle. He bound me again and Rollo handed him a rolled up, thick towel to wedge under my belly. And then he straddled my thighs with his and thrust inside me, bareback, as Rollo had done, and fucked me. At first he kneaded the muscles of my back and arms and his cock took on the rhythm of the soft, rolling gait of the massage, but as his own heat deepened, he stopped massaging me and went to fucking me hard like a dog.
He moved a hand around my thigh and milked my cock until I was almost ready to come again, and then I felt his hands at my throat and his fingers digging into my flesh, seeking out my windpipe. He brought me to the edge of his ejaculation and my unconsciousness three times before he released his load deep inside me, while I simultaneously experienced that fullest release of my own that morning . . . and . . . blacked out.
* * * *
When I came back into consciousness, I was on my back again, free of bounds, but Paul was sitting on the lounger beside me and I became conscious of my own moans and that I felt incredibly stuffed. My pelvis was elevated again, and one of my legs was spread and lay across his lap. I could feel the pulsing hardness of his erection on my thigh. He was worrying my nipples with one hand and looking down at me with an expression that approached awe. I looked down the line of my body and saw that his hand was inside me up to his wrist. It was slowly rolling back and forth and my pelvis was rolling with its rhythm. Rollo knelt beside my hips. He brought a cloth to my nose that smelled sweet and immediately started to make me feel groggy. I watched then as he lowered his lips over my cock and the stemmed stud in his tongue found my piss slit once again. And then I just went with the flow again until I drifted off into blackness.
I woke up in my bed, bathed and powdered and feeling a little groggy. It was dark in the room, but when I struggled up and went and pulled away the drapes on the French windows, I saw that it was only late afternoon.
Paul and Rollo were sitting, clothed in formal wear, on cushioned seats next to a table covered with a white cloth and set for three. Lit candles were placed here and there around the pool area. The two men were drinking from martini glasses. A third, unoccupied chair was positioned between them. I found my tuxedo in the closet and dressed and went down to them.
There was no mention of the debauchery at the pool in the morning. If I hadn’t been sore, I would have wondered if I had dreamed it all. The discussion was light – sports and action and adventure movies and a bit on current events and the business market in Puerto Rico. Rollo seemed quite able to keep up his end of the conversation. They also discussed the peculiar behavior of the workmen who had been working on the resort and just walked off the job – with the promise that they would be back. Paul said they almost were apologetic about it – and looked embarrassed when he pressed them for a reason. But they had avoided giving him one other than ‘national holiday.’ Paul had lived in Puerto Rico long enough to know that they could find a national holiday excuse for any day they didn’t want to work.
‘What’s a little surprising in their nonappearance is that they clocked in well before this. And they were good workers – well most of them. And good for other purposes as well,’ Paul said. ‘You would like them, I think, Ty.’
That’s as close as he came to mentioning what had gone on between us earlier in the day until much later, after the sun had gone down, and we’d plowed through three courses of food, including broiled lobster with shrimp and scallop chasers, had had our coffee, and were finishing off with snifters of brandy, sitting three abreast on the lounger next to the underlit pool, me sandwiched between the other two and them working my body through openings in the tuxedo with their hands.
After each of us had said, as all of us are want to do, that we needed to leave for our separate demands of the evening but didn’t actually budge from the comfort and ambiance of the moment – Rollo cleaning up, Paul updating the resort’s books, and me continuing my review of what I was supposed to be doing for Vado Pharmaceuticals in Puerto Rico – I did approach the subject again.
‘I never asked you what the fees are for room and board here,’ I said. ‘Not that I care what you charge, but my company is picking up the tab, and I should know what to tell them if and when they ask.’
‘As long as you continue pleasing me, there will be no bill,’ Paul said with a hoarse whisper. His hand was squeezing my cock rhythmically at that moment, so I had to assume I was pleasing him. But I asked anyway.
‘And do I please you?’ I asked.
‘Very much so – and Rollo too,’ Paul answered in even a deeper and more hoarse voice.
‘I am quite pleased with the accommodations,’ I answered. ‘And Rollo too,’ I added.
‘You are so accommodating yourself,’ Paul said. ‘I don’t want to go beyond bounds. Is there anything not – ?’
‘No,’ I interjected. ‘I’m sure that anything you enjoy I will find equally enjoyable. Both of you – together – even. I’m sure I could – ‘
‘After this afternoon, I’m sure you could too,’ Paul said with a laugh. ‘You needn’t bother to lock your door here at night,’ he then said as he rose. ‘We both have keys to all of the doors.’
‘I feel safe enough, I answered,’ as Rollo also rose to leave.
In the middle of the night, under a full moon that I let stream through the undraped French doors as I lay naked in the four-poster bed in my room, both Paul and Rollo quietly entered. They both were naked. They moved to either side of the bed and reached up into the corner of the canopies of the bed and brought down restraints on leather leads.
‘Is it OK to – ?’ Paul whispered.
‘Yes, yes, of course, if that’s what you wish,’ I whispered back. Rollo stretched my right arm and left leg up and out, as Paul did the same with the left. Then, as Rollo wedged pillows under the small of my back, Paul knelt at the foot of the bed between my legs and docked our cocks – pressing one cock head against the other and stretching his uncut foreskin over the tip of my cock. He closed a fist over the docked cocks and stroked them to hard. Rollo kissed me on the lips and then pulled up a club chair close to the side of the bed and watched as Paul and I moaned and sighed in unison.
When I had reached the shuddering and writhing stage, Rollo started handing various forms of dildo to Paul that he had covered in lube and both watched intently as Paul played in my widening hole with them.
When I was sufficiently dilated, Paul worked his way under me on the bed in full stretch and entered me from behind with his cock. Rollo then stood and took up the kneeling position between my legs that Paul had previously occupied. He then too worked his cock inside me and they double fucked me. As we were close to coming, Paul took my throat in his hands as he’d done the first time he fucked me and I ejaculated, in profusion, at the point of blacking out.
When I awoke it was after dawn and I was unbound in my bed.
For two days after this, the routine was more or less the same. Wild cocking at the pool in the morning, sleeping the afternoon away under the influence of some sort of drug, a quiet dinner of pretense that nothing was going on between the three of us – and double penetration sex at night. During this period, both Paul and Rollo frequently whispered in awe that they had no idea that someone as small of stature and young looking as I was could perform sexually as I did.
Even when I told them I had successfully lived in New York as a male escort, they remained almost incredulous – even though I repeatedly managed all that they said they couldn’t believe I would be able to.
* * * *
I was lying half on the lounger by the pool on my side and Paul was sitting on the one beside me facing me. My torso was half over his thigh and my arm wrapped around to his back, where I was playing the tufting of hair above his tailbone. Paul had interesting patterns of hair on his body that I liked to run my fingers through. My other hand was following the trail of hair up his belly and searching out his nipples in the matting there. I had his balls in my mouth, sucking on them, having just licked them down good. Paul was gently moving his fingers around my lower belly.
Rollo was sitting on the lounger on the other side, hunched over me, my leg wrapped around his neck, his attention intently focused on feeding the largest of a graduated string of balls inside my channel. Both men were breathing heavily and were erect and hard as rocks, and I sensed it wasn’t long before one – or both – of them would be fucking me. Rollo leaned farther over and took one of my nipples in his mouth and rolled it between his teeth and bit down on it. He grunted with pleasure as I cried out, releasing Paul’s balls from my mouth, only to have him push his cock into my mouth with a hand. And then he was leaning over me as well and chewing on the other nipple. I writhed in pain pleasure – and gasped as Rollo started to pull the string of balls out of my ass.
I felt a smattering of raindrops, and both Paul and Rollo sat up.
As Rollo was pulling the last of the balls out of my channel, Paul said. ‘I think it best we go inside. You haven’t seen my cellar playroom yet.’
‘You don’t want me to make you come first?’ I asked. ‘I think you’re close.’
‘I think it will be much more enjoyable in the playroom.’
We were in a stonewalled chamber straight out of a horror movie. Torches on the walls along with implements of torture. A sling, a bucking horse apparatus with a dildo protruding from the saddle, and another saddle-type machine the function of which I had no idea. And I couldn’t put much effort into figuring it out, because I was already a bit beleaguered. I was hanging from the ceiling with restraints at my wrists and above my elbows and wishboned back, restraints at my ankles attached to leads running off in each direction away from my body that had my legs splayed apart. Paul was between my legs in back feeding my channel with a cock encased in an apparatus with studs all over that were giving my channel walls extra special attention, and Rollo was in front of me, sucking my cock and adding weights to the end of a leather rope wrapped around my balls, stretching them toward the floor.
Paul said he wanted to hear me scream, and I was doing a lot of that. After a bit, Paul released my ankles and I was vertical – but he only did this so that Rollo could grab my butt cheeks from the front and roll my hips up and spread my cheeks so that his cock could join Paul’s in my channel. They rode me until all three of us had come.
Then Paul told Rollo to let me down and to set me up with what he called the ‘Big F.’ As he went up the stairs he said, ‘Let’s start at twelve and three – we can go up from there.’
The Big F turned out to be an ass drill, with Rollo setting it at twelve inches of penetration and three inches of thickness. It was the machine I hadn’t identified earlier. I was lashed down, half way reclining, with my legs spread and elevated and my hips rolled up. And a dildo-shaped drill was set between my legs. I could see it approach slowly from more than a foot away, and then it relentlessly drilled into my ass in a two inches in, one inch back, two inches in motion at the set depth and then went through a series of churning maneuvers. Then out it drilled, only to repeat the process all over again. A penis sheath went over my penis and balls and squeezed my balls and milked my cock in rhythmic motion.
‘We’ll let him go twenty,’ Paul called out from the top of the stairs. I’ll be down to watch the last five minutes and listen to his moaning.
No sooner had Rollo set the controls and the drill started moving toward me, though, than Paul was back at the top of the stairs. ‘Grab the guns and get up here, Rollo. We’ve got visitors. I half expected this.’
I was well over the twenty minutes and pretty much passed out from too much of a good thing – in this case accompanied by the rat-tat-tat of automatic weapons fire overhead – when I opened my eyes at the sensation that the machine had stopped . . . and was looking up – and around – at a circle of local Hispanic militiamen, stripped to the waist, in jeans, with bandoliers of bullets crisscrossing their chests and smoking automatic rifles at their sides. They were all heavily muscled, glistened with sweat, and covered in tattoos.
They looked as shocked to see me here, like this, as I was to see them. Someone called down from the top of the staircase in hurried and panicked Spanish. The man who looked to be the leader of the group answered him back in leering but unhurried tones and then directed me to ‘Come with’ as I was released from the machine. I was literally dragged off the machine and up the stairs and out the back of the lobby and into the scrub. Looking back as I was dragged, I could see a swarm of blue-uniformed men exploding into the lobby from the front.
I was half in shock – if for no other reason than the surprise of it all – as I was manhandled through the scrub to a road, where two flatbed trucks were parked. I was slammed down on the tailgate of one of the trucks while the armed men fanned out in a semicircle facing the resort, which no longer was in sight.
The leader of the group wasted no time in moving in between my legs while slapping them apart. He had one hand at my opening and the other jerking at my cock. He almost went into shock himself when I smiled up at him and raised my hands to his chest and began to trace the tattoos that flourished there. He was working his fist in me, no doubt expecting me to cry out in pain and violation – which may have been what gave him a thrill. But I found him arousing, especially the tattoos, and I reached down and tugged at the front of his jeans, opening snaps until he was overwhelmed with the moment as well.
He fucked me hard, as then did the rest of the band – or most of them, in succession. While the last guy was doing me – and I was enjoying the undulation of his tattoos on his chest and arm as he was working on me, four of the band jumped up onto the back of the truck and urinated on me.
I didn’t like that much, but they seemed to.
But shortly, each band member not having taken more than four or five minutes to shoot their load in me as keyed up as they had been, someone whistled a warning, and I was shoved off onto the side of the road, and the men were jumping onto the trucks and hauling ass out of there.
When I looked up, a policeman in a blue uniform was standing over me, surprised – and aroused – at what he found.
I was no less aroused by the uniform and the tenting at his crotch and came up on my knees and unzipped his fly and relieved any anxiety he had. And he let me do so without the least embarrassment – as did the next policeman who showed up. I’m sure they thought I was acting in relief from having been saved from the armed band. But in reality the rough fucking and tattoos on the Hispanic militants still had me in high heat.
* * * *
‘OK, give me an order for these colors,’ Paul said brightly early the next afternoon as he came out to me at the pool. ‘Red, blue, green, gold, and transparent.’
‘Transparent’s not a color,’ I said, moving a bit gingerly in my chair. Paul and Rollo hadn’t let the scare of the previous day interrupt their visit to me in the night.
What had transpired the previous day was that the resort had been ‘visited’ by a band of bandits, one of many roaming the hills of Puerto Rico of late and terrorizing the tourist resorts. Such bands swept in and divested all of the well-heeled visitors, even those in the middle of a golf game, of whatever could be quickly grabbed and then ran for the hills again. This band had marked the Sao Paulo Resort for visitation, apparently not being aware that it was closed for renovation. The renovation workers had heard this was happening, though, so they were staying away.
‘Why should I put an order to those colors?’ I asked.
‘Just humor me and do it.’
‘OK, anything to please you, oh lord and master. How about green, blue, transparent, gold, and red.’
‘So be it.’
‘So be what. Why’d you ask me to put them in order.’
‘Because the lads won’t sort themselves out.’
‘Excuse me?’
‘The renovation workers couldn’t warn me of the raid or the raiders would visit their villages some night. But the boys doing the landscaping were good enough to keep an eye on the resort from a distance and summon the police up from San Juan the moment the bandits arrived. Rollo and I were forced back across the pool – so sorry for your little encounter with the bandits for the short time they were in the hotel – but the police arrived before any real damage was done. We shouldn’t have to worry about them again now until after they’ve seen that the renovations are complete and the hotel has bookings again.’
‘I still don’t understand what – ‘ But then I followed Paul’s line of sight, because he wasn’t looking at me. And there, by the door into the hotel from the pool area were five hunky Hispanic young men, standing all in a row, with big smiles and completely naked except for condoms of an assortment of colors – red, green, blue, gold, and a transparent one – and they were all in various stages of erection already.
‘I told them I’d reward them for saving our lives – all of our lives,’ Paul explained.
I spent the afternoon with my legs spread and my channel entertaining cocks crowned with condoms in a variety of colors. I can’t say I didn’t enjoy the Hispanic hunks who had perfected the sculpting of their bodies the natural way – by honest hard labor. And I decided to be a good sport about it, because their loyalty to the resort very likely did save our lives.
The next day, my week was up at the Sao Paulo Resort, and the driver was waiting to take me back down to San Juan, where presumably the Puerto Rican branch of the Vado pharmaceutical company was ready to receive me.
I hadn’t exactly had the quiet, celibate week I had planned on, but I’d had some really interesting – and stretching – experiences. And I decided that my life of being a good boy could start now just as easily as a week ago. April wasn’t arriving for another three months. There was plenty of time to get my act straightened up.
As I was leaving, Paul and Rollo were standing at the door. Rollo looked really sad to see me go; Paul just waved and smiled and said, ‘See you around,’ which I felt was a little strange. I thought that all I’d let him do for me – in exchange for room and board and some interesting company – was worth more than a flippant good-bye.
I had thought the driver would take me back to the El San Juan Hotel – or maybe, if the office had really gotten its act together, to the apartment overlooking the sea that they were supposed to lease for me. But instead it rolled up to the door of a high-rise luxurious condominium on a hillock between the mountains and the coast that surely had great view of both the Caribbean and down into old San Juan as well.
‘Please take the elevator to the penthouse, sir,’ the driver said as he opened the door to the backseat of the limousine for me. ‘The security staff knows who you are and where you’re going. I’ll take your bags on to the hotel and will be back and waiting down here for you when you are ready.’
‘I don’t know who I’m going to see,’ I said. ‘Tell me who? And why you aren’t taking me straight to the hotel.’ I was a little piqued I was being kept in the dark.
He didn’t answer my questions. He just looked a little pained and repeated, ‘Please take the elevator to the penthouse, sir.’
I walked into the lobby, which was two stories, the far wall of which was all glass and had a magnificent view over the city and water. A liveried attendant was waiting at an elevator that was set by itself, away from the bank of other elevators. He was looking at me and gesturing with an outstretched arm at the open elevator, making it pretty obvious where I was supposed to go.
A butler met me at the elevator and ushered me into a plush lounge that took up one corner of the building and provided a sweeping view from ocean to city to mountains across the expanse of a wraparound terrace.
‘Dr. Holt-Evans will call for you shortly, sir.’
Ah, that explained it. Peter Holt-Evans was the company’s branch manager – the suave, mature Englishman who had banished me for the week. I wonder what he’d have to say to the concierge at the El San Juan who had sent me into the jaws of just exactly what I’d been sent to Puerto Rico to avoid – most evidently to the full knowledge of their branch president.
I was kept waiting for only about ten minutes when the butler returned and said, ‘The doctor will see you now in the examining room.’
I stood, perplexed, and followed the butler down a corridor into the bowels of the penthouse apartment that evidently took up the whole floor. ‘Examining room,’ I thought. ‘A different doctor than Holt-Evans? A shrink, maybe? I’m going to be grilled about what I’ve been doing for a week? Did Holt-Evans find out and I’m in hot water here already? What do I tell him?’
But the examining room I was led into was a medical examination room, and Dr. Holt-Evans was waiting there for me. He was wearing a white medical coat that came almost down to his ankles.
‘Hello, Ty,’ he said in a jovial manner when I entered the room.
‘Hello, Dr. Holt-Evans,’ I answered. ‘I don’t understand – ‘
‘Ah, I’m sorry. I neglected to tell you. I’m the company physician down here as well as the president. A mere formality, but we exam all employees as they come on board at the branch. We offer full, comprehensive medical benefits, you know, but I’m afraid that comes with some level of intrusion into your personal health. This is a mere formality. But could you take off your clothes down to your briefs, please, and hop up on this table and lay back.’
He was patting the top of a padded examination table, complete with foot stirrups.
I was still confused, but I did what he asked. He took a stethoscope and started listening around on my body – my throat, my chest, and my belly. Asking me to cough and breath deeply for him.
I murmured a query when he lifted my legs, slipped off my briefs, and inserted my feet in the stirrups. He then wrapped restraints around my ankles and raised the stirrup mechanisms up and to the side. But he ignored me and had one of my arms raised above my head and the wrist restrained to the side of the table before I was able to become more vocal in my questions.
The other wrist tied down, he cheerily said, ‘Not to worry. We’re just doing a prostate exam at this point.’
‘I don’t understand. Wouldn’t I stand and bend over for that exam?’ As I asked that question, a bit heatedly, he was snapping latex surgical gloves on his hands. ‘And why the restraints?’
‘Well, because I’m going to conduct the prostate exam with my dick, dear boy,’ he answered jollily. And as he said it, he was unbuttoning his medical coat to reveal he was naked underneath – and had a very respectable full erection, already crowned with a condom.
‘And I’m going to help him,’ another voice sounded from the corridor, as Paul walked into the room, naked.
I gasped as Peter Holt-Evans moved in between my legs and started lathering up my hole with lubricant.
As he fucked me, in long, deep strokes, Paul provided the explanation.
‘Peter and I are brothers. Sending you to my resort was rather a test. The office in New York wanted you to pass the test. After seeing you, Peter wanted you to fail – but was, and is, prepared to cover for you for continued services rendered. So, he bribed the concierge at the El San Juan Hotel to guide you to my empty resort – and, as requested, I did everything I could to make you fail the test, to seduce and use you to the ultimate degree. And I must say you failed with flying colors.’
If I was going to fail – and especially because the brothers wanted me enough to help cover my tracks – this is just the way I wanted to do it. I told Peter he could release the restraints and I’d gladly join in the fuck. It was as good an answer to my addiction to fetish sex as I was going to find.
Peter said he’d release me in a while – that using restraints and the medical angle was a fetish of his. ‘And Paul here has told me you are quite accommodating to fetishes.’
I soon found another fetish of his – which gave even more motive to the restraints. As Paul watched, licking his chops and taking time for kissing and some mouth-on-cock play with both me and his brother, Peter lathered up my torso and pits and legs and pubes with shaving cream and shaved me smooth. I’d never had this done before but I was game. I’m game for almost any fetish that doesn’t kill me – and for which I get paid well somehow.
When I was released it was only to become the meat between the Peter and Paul bread of a fuck sandwich, as the two brothers took me between themselves in double penetration and then left me to shower and clean myself as, aroused to the heights, the two brothers went in search of a bed to resume their fuck without me.
All told San Juan was promising to be an ideal assignment for me.
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