The holiday nearly went wrong before it had started! My old pal Bill had a bust-up with his girlfriend some days before our scheduled departure, and almost cried off, but I persuaded him to join us on the hopes of finding a replacement girl at the resort. We had booked a two bedroom penthouse apartment, with roof terrace complete with hot tub, and stunning sea views over the Caribbean. If he had dropped out I would have had the choice of keeping the suite and paying for all of it on my own, or down-grading to a standard double room.
My wife of some three years, Judi, was fond of Bill, and had been very persuasive when we were coaxing Bill to join us, we all three of us were great friends and were sure to have plenty of laughs for our week in the sun.
Judi was a superb looker, a dancer's body, photo model face, and the grace of a panther. She had the kind of looks that cause conversation to stop when she came into a room full of people, she was now in her mid-twenties, and as far as I knew she had only ever made love to me- certainly she had been a virgin when we first met about six years ago. I had broached the subject of our sharing our sexual appetites with one or more partners, but she would have none of it- she had no interest in sharing her body with anyone but me.
I, on the other hand, wanted to see her being fucked by a bloke with a monster cock, while I spectated and or participated.
I began to day dream of the scene in our luxury hotel suite with her gasping to orgasm after orgasm as she is conclusively penetrated by two or more cocks at the same time. I thought about little else in the days leading up to our departure, leading to a very active sex life for us, as I had a hard-on almost permanently, and got to use it as often as time or opportunity would allow.
As part of her holiday preparations she had a full Brazilian wax of her pussy, and a short boyish hair cut which made her look like a well developed teenager.
Our flight was un-eventful, and long. The film was boring, the food bland, and the seats not that comfy after so many hours, so we were delighted when we began our decent to Montego Bay.
The Hotel shuttle was there to meet us and soon we were on our way from the crowded airport along the costal road, through coco-palms, and brightly coloured flowering bushes and trees. Soon we arrived at our hotel, which from first impression did not disappoint one iota.
Check-in was slick, and the glass lift whisked us up the outside of the hotel to our penthouse floor.
Our porter opened the double doors and ushered us into the Presidents Suite, and WOW! What a pad, all glass outside walls, surrounded by a terrace on two sides, and a roof garden on the third.
We all agreed that the first priority would be a relaxing dip in the hot-tub on our private roof-garden- and then we would see what we would do next.
We went to our respective rooms to change, Judi stepped out of her travel cloths and took her latest bikini from her suitcase-small would be an inadequate description. Three tiny triangles attached to coloured string, and as it went on I felt my cock stiffening, the lower part only partly covered her pussy, both waxed sides clearly visible ,just the slit seemed to be hidden, as to the back view, well the string hid NOTHING, her pert bum was completely on display. She then put on the top which covered about half of each tit, the material thin enough to show the outline of her perky nipples.
"Like it Dan?"
"What do YOU think? "I said as I showed my stiff erection, which I stroked slowly, and I thought seductively.
"Lets chill out in the tub first, then you can have me any way you want Darling!"
We went out into the hot sunshine, picking up our complimentary Champers on the way, and plopped into the bubbling Jacuzzi.
We had been in the tub about ten minutes when Bill came trotting out to join us.
"This is a bit of alright, and if I may say so are you Judi, that Bikini of yours is a knock out!"
We drank our fizz and relaxed, kidding around, and making plans for the rest of the day.
Bill could not take his eyes off Judi, whose top had slipped somewhat in the bubbling water and was now showing most of her perfect breasts, but with the champagne flowing and all the joking and laughing she seemed not to care too much.
After a while Judi declared that she was going to do a bit of sunbathing before anything else!
She stood up to get out, and gave Bill his first view of her naked arse, and almost naked pussy.
Towelling herself off, she enquired if either of us would be good enough to oil her back?
Before I could suggest that Bill do it, he had volunteered and was standing up in the tub, trying to hide the huge stiffie in his Bermudas.
This was working out even better than I hoped- I had done nothing to get them together and here they were, about to have a sensual experience, with me as spector and we were only at the very start of the holiday.
Judi stretched out on one of the lilos, face down, removing the Bikini top to leave her back and buttocks bare except for the coloured string round her waist which attached to the one that disappeared between the plump cheeks of her pert arse.
Bill picked up the suntan oil, and pouring a little into the palm of his hand, he began rubbing it onto her back in slow and sensuous circular movements, starting near her shoulders, and working down her back , fanning out to feel the bulge of her breasts as they poked out from under her.
His prick was tenting his shorts as he worked, and I pretended to be napping, so he could continue felling her up unobserved , the oil went on and now his circling hands were just above her bum, and getting closer with each sweep.
Hmmm! that's lovely she murmured.
Thus encouraged he began oiling her arse, staying away from the cleft, just oiling the cheeks in circular motions.
After a bit of this I noticed he had changed the direction of his massage and was now coming up from her thighs with us thumbs going between her legs with each stroke.
I was sure that his thumbs were touching her pussy and probably running over her arse button, nothing intrusive, but a good sensual grope none the less.
Rather than tell him get his fingers out of her private bits she asked him sweetly if he would do her thighs and calves as wonderfully as he had doe the rest!
He did what he was told, and when he was finished, he lightly patted her on the rump and told her that he wanted the job of chief suntan lotion applier for life.
She giggled, and confirmed the job was his- adding why not does her front, that way she could sunbathe UN interrupted for a while.
Rolling over on her back her naked breasts were just fantastic, full and round her nipples darkened and erect, standing out proudly.
Bill did not know his luck and began oiling her immediately, tweaking the nipples between his thumb and forefingers, she gave a little groan, and looked over towards me to get a reaction to the lewd carry-on, I of course pretended to be asleep, so she relaxed, and knowing her as I did, she would be lubricating and getting ready for an orgasm any minute.
Bill moved down to her waist and belly, oiling away and making no attempt to hide his huge prick, which she was looking at with some interest from time to time.
He began on her thighs, running up the insides with his thumbs, allowing them to go inside the flimsy triangle of material; soon it was obvious that he was inside her cunt as well as her pants, as she started moaning quietly in time to his movements.
"I don't think you should be doing that to me Bill!"
"Aw come on you love it"
"Dan might wake up and what then?"
"Dan is a man of the world- he would want his beautiful wife to be happy, and if that includes a feel - well OK"
With that -he gave up his pretence of oiling and put his right hand down her mini pants-fingering her clit and sopping pussy, stroking her the length of her puffed lips, the other hand feeling her freshly oiled breast.
She sat up with that realising that she had let him go too far, and pulling his hand away from her pussy she sternly told him to stop or she would be cross with him.
He stopped frigging her, but left the other hand on her tit for a while longer, feeling her pointed nipple, and pinching it gently.
She gave him a swift kiss on the lips and sent him back to the tub, where I continued to look fast asleep.
As he left her she told him to wake me in ten minutes and send me into our bedroom, so saying she gave him a lecherous look, perhaps with a bit of longing.
I played my part till she had gone inside.
I then asked Bill how he had enjoyed Jill's pussy, tits, arse, etc.
"Oh shit!sorry pal-its just that she is so fucking gorgeous and sexy I couldn't stop myself, and to be fair she was not exactly shoving me away you know."
I then told him my fantasy about her being fucked in front of me by someone else.
His already huge prick got bigger with the news
"When do I start mate?" he exclaimed" I'm ready to fuck the daylights out of her right now!"
I then explained that she was not in agreement with my plan, and we would have to trick her into being fucked by him and then both of us with one of us in each of her darling holes.
As I had been mulling this over for the previous week I had several fantasies already worked out.
I gave Bill the basics off my plan and got ready to go inside.
She was on the king-sized bed legs apart playing with her clit, looking as fancyable as ever I had seen her.
"Want a good Fuck cowboy?"
"You bet I do, but are you sure you gat the right cowboy"
