Being recently separated from my Wife of twenty years was rough on me. After we had parted, I set her up with a friend of mine. Knowing she was in the arms of another man eased my burden for needing to continue to look after her. I myself needed time by myself. For the first time in my life, I did not look at every pretty girl with thoughts of bedding her. Taking this time for myself seemed to lead me into depression, rather than being any sort of Zen cleansing as I had hoped. I drowned myself in my work. In the month following my separation, I completed more engineering designs than the entire previous year.
The quantity of work I produced, in addition to the intricate details included, found favor with the President of our company. I was given a month to finish up my current projects, then was being sent to South Florida and the Caribbean on an extended assignment. The associated work for the trip was minimal, spaced with excessive leisure time. As he had scheduled a week on more than one island with no associated work, it was clear that I was being sent on a forced vacation.
I began the planning process with a working lunch between my secretary and I. This was mostly an informational meeting for me. Edy was always far ahead of me in knowing corporate direction and planning accordingly for them. She laid out for me our itinerary with tickets, hotel suites, and transportation all booked. I say our, because Edy informed me that she would be escorting me.
She assured me that Mr. Iverson, the President, had approved the arrangement. She also assured me that her husband could use the time apart. Finally she informed me that I needed someone to take care of me. This was emphasized with her nylon covered toe tracing the inside of my calf seductively. Looking over her bookings, I began to question each stay having only one hotel suite, her finger touched my lips, shushing me but done so in an erotic fashion. I began wondering who worked for who as Edy continued to inform me that I was to be at her house the following day, Saturday, no later than 10am; “where I will give you further instruction.”
Pulling into Edy’s driveway, my ponderings as to whether this would be more of a personal visit were squashed, seeing her husband Mike wave to me. At the corporate picnics and Christmas parties where Mike and I had previously met, we had got along well. This morning he welcomed cheerfully wearing swim trunks and sandals; “Edy forget to tell you to bring trunks?”
Edy, being all hearing, stepped out of the door clad in a lovely bikini with a cold beer in hand for me; “Do I ever forget a detail.” “Mr. Vandenberg is here to be instructed in Caribbean etiquette.” “Now be a good host, Mike, and establish the proper attire.” Apparently our day would be “clothing not optional,” as he led me to the back yard obediently removing his trunks.
Edy stepped forward turning and asking if I could help with her top? It was a pleasure removing her bikini top. Edy grew up in Puerto Rico, she was very pretty; dark olive colored skin, long curly black hair, small but firm breasts, and an ass to die for. She was pretty, but it was her attitude that stuck in your mind. She wore her skirts skin tight, knowing the perfect stances to show off her ass. She was quick to include tongue rolls, for exotic emphasis to her accent.
She used her island sex appeal to her advantage. An example would be seducing Mike, a Navy officer almost 20 years her senior. Her gorgeous body attracted many men. Her virginity, however, was held. It secured the promise of marriage, a house on the main land, in a suburb, and with a pool. She lived in comfort as she continued to build a career.
Taking a seat in the shade, I felt a sense of pride in seeing the nipples that I had just helped to uncover. They matched what I had imagined almost exactly. Her breasts were very firm, appearing to be held up and out by an invisible force. Edy’s nipples were luscious, retaining a puffiness of youth, as she was barely 20. There darkness, almost brown, was new to me. My wife had been blond haired and blue eyed with pale pink pussy and nipples. Dina was very sexy, but almost the opposite of this Latin beauty.
She stood before me, looking me over hungrily. The oddity of this did not escape me, as she was extremely hot and I had never considered myself the least bit attractive. With her Office Manager efficiency she informed me of the day’s agenda:
“I will remove your clothes so you can acclimatize to nudity. You and Mike together will remove my bikini bottoms. Like handing over the keys to a car on loan, Mike will release me into your care. The rest of the day and until we return home, I will serve you. We have YOUR favorite beer. We have YOUR favorite steak. We have YOUR favorite pipe tobacco. Who touches these breasts, slaps this ass, or fucks this pussy, is all up to you!”
Having established a mood of transformation, Edy began removing my clothes. Standing before her, I could feel the weight of cares removed from me with each article of clothing that she took from me and handed to Mike. With my shirt now off, her hands explored my chest working their way down to my belt. While undoing my belt and pants, her kisses followed the path that her hands had just established. Though she took her time and lingered, paying special attention as she released my cock, it was done all too soon. The feeling was amazing and freeing as a breeze blew across my testicles.
Edy pointed out to Mike that he needed to learn such self-control. She drew attention to the fact that his cock was standing at attention while mine maintained a sense of mature dignity. “Look how big and self-assured his cock is, compared to your little boy begging for attention Mike.”
Feeling for him, I spoke up that “Mike’s cock is quite impressive and having such a sexy wife, it is no wonder he is so hard.”
Mike however, demurred “She is right, your cock is very impressive. I wish mine was even close to that size.”
As Mike and I knelt to remove her bottoms, I willed my cock to not get hard, wishing to maintain that faux air of being in control. My eyes explored this sexy Latino, as we jointly exposed her ass and pussy. Her pussy was very lovely, a full dark bush, nicely trimmed. Trimmed just enough to not poke out from her tiny bikini bottoms and enough to reveal her beautiful dark pussy lips. Edy’s ass was not big, but was certainly fuller than most Caucasian women, and stuck out slightly in an extremely attractive bubble shape.
Mike’s hands softly felt her ass and pussy, feeling the bronze skin. My mind began to picture her laying out in the nude, she obviously had no bikini lines in her tan. My thoughts were cut short by her sharp rebuke of Mike. “That is not your ass, nor your pussy, it belongs to Mr. Vandenberg!”
Mike was certainly within her control. It was quite obvious that it had not just changed with my presence. She had told me previously that Mike was the only man who she has had sex with, but it sure seemed that he was a cuckold in training. Her words suggested that I was in control, her tone however, indicated that she was not accustomed to being submissive to anyone.
Taking that control, that she “said” I possessed, I told her “That is right, that ass and pussy is mine. As such, it is not your prerogative to chastise anyone for touching them!” I cut her attempt to argue short, pulling her over my knee and slapping her ass cheek soundly. “Mike, come over here and rub Edy’s reddening ass.” Her attempt to wiggle away from him brought my hand sharply against her other ass cheek. She laid across my lap, submissive to Mike’s rubbing her ass cheeks and my hand feeling her pussy.
Her pussy was warm and wet, her moans responsive to my fingers touching and entering it. She responded with “Yes, Sir” as I reiterated the day’s agenda while fingering her tight little brown cunt:
“You will bring me and Mike a beer upon request. You will fill and light our pipes. You will cook and serve our steaks. You will suck our cocks upon demand. You will take his cock or my cock in your pussy when I tell you. You will spread your gorgeous ass for my cock when I tell you.”
As Edy ran off to get both of our pipes and tobacco, Mike explained why her “Yes, Sir” was slower and quieter concerning spreading her ass. Mike had been pressuring her to “give up your booty” from the first day of their honeymoon. She had denied all of his requests to fuck her ass.
Mike went into the house to take a piss just as Edy returned. I took this opportunity to firmly establish my control. As Mike stepped out of site, I bent her over a table. With a hand holding her long black hair and the other spreading her ass cheeks, I whispered in her ear; “If you are not perfectly obedient, if you do not suck my cock perfectly, if you do not …., I will have my big cock buried in your tight, little, sweetly, puckered asshole.” For emphasis I pressed my finger into her ass, my finger massaged and fucked her asshole. She squirmed, at first trying to get away, then pressing back against my finger taking it deeper. I did not remove it until I heard Mike’s footsteps returning from his restroom run. “Make him proud!” I commanded as I slapped her ass.
A change came over Edy, she had always allowed men to think they were in control. Edy had previously established in her mind what she would provide to a man and what it would be costing him. She was a master at convincing men that her plan was there plan, what she wanted was what they wanted. She was now trying to protect her ass. Truly subservient, she waited on us anticipating our desires. Her breasts, pussy, and ass were always available to be ogled, fondled, or kissed.
If I just hinted at wanting a blowjob, Edy was on her knees with my cock in her mouth. I had her stop short the first time but filled her mouth with my cum just prior to her serving us our steaks. Mike had not restrained, within seconds of her taking his cock in her mouth, he was shooting cum down her throat. She had his cock hard again within an hour, very impressive with him being over twice his age.
As the day turned into evening, Mike and I had become close friends. I shared with Mike how I would be fucking his wife over the following two months. I told him that I would send him pictures of her nude on the beach and in public. I would share pictures of her getting massages, the pictures showing both female and male hands caressing her body. I told him how I would send him pictures of my cock penetrating each orifice of her body. I also bent her over in front of him, inserted two fingers in her cunt, withdrawing them covered in her pussy juices showing him what a horny little bitch his wife was.
He shared with me stories of his life. How Edy had fulfilled his dreams. He shared his fantasies. He shared his secret fetish, Mike desired a golden shower. He had imagined a woman peeing on him. While on ship, it was a man standing in front of him, as he kneeled with piss splattering on his chest. Many times while he pissed, he pictured Edy bent over in front of him, while his piss streamed over her ass.
I instructed Edy to get down on all fours at the edge of the pool. On her hands and knees, Mike began pissing on her back, down to the crack of her ass, and back up even into her hair. I watched as she stayed put, desiring to get out from under his stream of piss. I watched his face, the ecstasy, him watching his own piss splatter over his wife. As the stream turned to dribbles, Edy dove into the pool, washing herself clean.
He helped her out of the pool, kissing her passionately, thanking her. She as well had a permanent smile on her face. She had given him something she had previously refused. I joined in telling Edy, “You were amazing, but not perfect. You cleaned yourself prematurely.” She offered penitence, as he sat in his lounge chair, she spread her legs backing up over the top of him. While he sat there staring at her gorgeous ass, she began pissing on him. Before she finished, I added my contribution. Scissoring her head between my legs, I sent a stream of piss over her back and ass, combining with her piss and pouring onto the chest of her husband.
The two of them were soon frolicking in the pool washing themselves clean of piss. He was obviously a happy man. She was more childlike acting her age than I had ever seen her. As I reached down, helping her out of the pool, she whispered in my ear, “I need fucked. Please, fuck me Mr. Vandenberg.”
As I lit my pipe to relax, I commanded Edy to bring me some lubricant. They did not keep any in their house, thus the need to have her purchase Vaseline as a substitute. She was allowed to wear a small rain coat (not quite covering her luscious ass) into the 7/11, but nothing more. I was enjoying feeling in control. As an engineer I always controlled things, not people. People should be able to think for themselves. From a new perspective of controlling out of fetish rather than necessity, I began instructing Mike on lubricating Edy’s asshole. Not so much on how to, but as to her need to submit.
I tasked Edy with lubricating my cock. She set about stroking my cock with Vaseline eagerly. A touch of fear concerning losing her anal cherry remained, but was drowned out by her excitement. While I sat reclined in my pool chair, Edy squatted above my cock with Mike helping to balance and hold her up. She had the responsibility of guiding my hard cock into her ass. With just a second of hesitation as my swollen cock head pressed against her puckered asshole, she pushed down taking the head past the sphincter. As I caught her hips in my hands, holding her from going deeper too quickly or from climbing off of me, a squeal escaped her lips.
My first assumption of pain appears to be incorrect as she began breathlessly talking to her husband: “His cock is huge!” “My asshole is stretched!” “Look at his big cock stretching my ass!” “My pussy, my pussy, lick my pussy!” Needless to say, he complied. As I slowly slid her ass farther and farther down on my cock, her husband licked her pussy. While she squirmed on my cock, pushing it deeper into her Puerto Rican ass, I felt his tongue start lapping from her clit all the way down to her stretched asshole.
After initial hesitation, his tongue was soon licking not only her pussy and ass hole, but more and more of my cock. It was not along before my balls were receiving the attention of his mouth at the southern point of his licking her pussy. It took her body beginning to quiver in orgasm for him to refocus on licking up her cunt juices which were flowing freely.
My hips began pushing harder and harder against her ass as her moans were replaced by screams of pleasure. Mike’s tongue could not keep up with her bucking, leading him to fill her cunt full of cock before her orgasm began to fade.
Edy’s ass was heavenly, so tight, so warm, so receptive to my cock. It squeezed my cock from the tip of my cockhead to it’s base as no pussy can. Mike licking only increased the pleasure. Finally a new sensation, Mike’s cock fucking her pussy in time to the long, fast, and hard fucking that I was giving her ass. I was on the verge of filling her ass full of cum when Edy and Mike simultaneously began moaning in orgasm. His cock slamming into her caused the lounge chair to collapse, my ass hitting the ground hard. He did not miss a stroke, filling her pussy full of cum.
With an ass probably as soar as edy’s, I dove into the water, washing my cock. I was not done, but needed a second to recover from bruising my tailbone. Emerging from the water to see Edy’s pussy dripping Mike’s cum was enough recovery for me. While Mike held Edy in his arms I entered her pussy. This would be the first of many times that I would feel her Latino cunt wrapped tightly around my cock. Mike encouraged me to fuck his wife. As the world faded to tunnel vision of orgasm, I heard Mike’s promise: “Train her to truly be submissive over the next two months; she will be yours the first weekend of every month thereafter.” I answered by adding my cum to his still flowing from her pussy and down my balls.
As she swam laps in the university pool, Jenna couldn’t help but admire the dive team practicing at their art. Each time she took a rest, she was inspired by the incredible acrobatics the divers could accomplish with just seconds in the air. There was one diver in particular she enjoyed watching, morning after morning as she trained in the pool. Unlike the other members of the team, he was broad and muscular, tall and dark-skinned. Somehow he was just as graceful as the other divers as he twirled in the air down to the water. Jenna wondered to herself how he managed to keep such exquisite control over his body as he fell.
Jenna had recently taken up running, and was feeling sore and stiff from a long run the day before. As she rested at the end of the pool, she made the quick decision to cut her workout short and stretch in the hot tub. The warm water would be good for her muscles, she rationalized. She easily pulled herself out of the pool, slid into flip-flops, and walked quickly to the hot tub. As she slid into the warm water, her muscles immediately relaxed and she spread her legs into a long stretch, letting out an unintentional sigh.
As she sat there stretching, feeling the tension and pain drain out of her muscles, she looked up to see the diver she had been admiring slip into the hot tub next to her. She politely said “Hey,” but it came out more like a whisper. He smiled and gave a quick nod. Jenna was glad he didn’t want to talk; she didn’t know what to say to this stranger she had been watching every day for weeks. As he sat down, his eyes flicked from her face to her breasts and down to the space between legs, sprawled in a deep hip stretch. Suddenly self-conscious, Jenna said apologetically, “Sore legs from a long run…” and closed her legs, deciding to stretch her arms while she waited for him to leave. This was no better; every arm stretch she knew either involved arching her back, pushing her breasts out towards him, or pushing her arm across her breasts, pushing them down and making them appear larger.
Despite her discomfort, Jenna didn’t quite want to head to the locker room. She was enjoying the opportunity to be so close to the beautiful man she had admired from afar. He was even more impressive up close; his arms and shoulders rippled with the muscles of a swimmer, and his small waist revealed the most toned abdominal muscles she had ever seen. She almost wished they weren’t in the water so she could get a better view of his legs and ass.
Perhaps reading her thoughts, the diver offered, “I’m a yoga instructor, I could help you stretch your legs out.” Surprised, Jenna replied “Uh, sure,” without thinking.
“Okay, let’s go to the sauna,” he said as he got out of the hot tub. At first, Jenna was happy for her affirmative response. His legs and ass were every bit as gorgeous and toned as the rest of his body. Once he got out and turned around, Jenna realized what she had done. “What were you thinking?” She thought to herself. It was obvious that he was interested in more than helping her stretch, from the way he looked over her body to the bulge in his speedo that was growing as she walked toward him. And she didn’t even know his name! Nothing would happen, she assured herself. Jenna promised herself that she wouldn’t allow him to touch her, just to show her the poses and leave.
The heat and dryness of the sauna made it hard to breathe at first. Jenna laid down her towel and stood on it, waiting for instructions. The diver wordlessly moved into a long lunge, and Jenna followed. She was grateful for the dim lights of the sauna, as she was much less self-conscious. Moving into the deep stretch the way he had done, Jenna thought to herself, “I could have done this on my own. Why am I trusting this guy?”
Before she even noticed his movement, he was beside her, moving her torso into a deeper stretch and gently guiding her into the right position. As his fingers touched her skin, Jenna felt a shiver of excitement go through her, but she fought to keep still. Even though she had told herself she wouldn’t let him touch her, this seemed innocent enough. As they worked through a few poses that stretched and softened her muscles, he stayed right behind her, his body pressing up against hers. She could feel his hard cock pressed against her back, but she chose to ignore it. This stretching was worth being touched a little; she could tell her body was relaxing and her soreness was disappearing.
Her head was hanging down to the floor when the diver touched her right breast to pull her upright again. He let his hand rest there, even after she was standing. As he pulled his left hand up to her stomach, she whispered, “No,” but she made no move away from him. His hands began to move around her body, caressing her over her thin Speedo suit, feeling her taut nipples, and down to the wet area between her legs. As he moved the swimsuit aside, she straightened her legs from the plié position, about to resist. He followed her up, rubbing her with the strong fingers of his right hand, and slipping his left under her suit to fondle her breasts. Body tired and loose, Jenna couldn’t resist the sensations between her legs, and relaxed into his hard body. When he had nearly brought her to climax, Jenna’s body began to tense up, preparing for orgasm. The diver sensed this, and he lifted her at the waist, turned her around, and kissed her. The kiss sent another shiver through Jenna’s body, but this one she couldn’t hold in. When he released her from the kiss, she began to protest, “No, I have a boyfriend,” but he only had one word for her, “Relax.”
He kissed her again and began to pull the straps of the swimsuit from her shoulders. She hated to admit it, but she was enjoying the feel of his hard member pressed against her torso, and the sweet taste of his soft lips. Before she could tell herself no, she reached to his cock and stroked it through his Speedo. This put him over the tipping point: he quickly scooped her up and before she knew what had happened, she was laying naked on her towel with his head buried between her legs. His tongue worked magic, stroking up and down around her clitoris until she was on the edge of orgasm. Her protests had turned to moans, and as she looked down at his beautiful body the orgasm coursed through her.
The diver gave her no time to recover. By now, she was ready to beg him to put his cock inside her, but she didn’t have to. Before she could say anything, he was lying on top of her, and to her own surprise she guided him in with her hips. As his long dick slid into her slick pussy, Jenna let out a moan of pleasure. He went deeper with each thrust, and when his cock had gone all the way in she felt the most incredible sensation of fullness. He knew how to move his body to stimulate her inside and out, and as he fucked her she cried out in pleasure over and over. Despite herself, she wrapped her legs around him and pulled him close for another kiss. The diver’s last few thrusts brought her to orgasm again, and their bodies tensed together in mutual pleasure.
Jenna felt exhausted, but noticed the soreness in her legs was gone. As the diver rolled off of her, she wrapped herself in her towel and began to head toward the door, embarrassed that she had given in so easily, and enjoyed the encounter so much. Behind her, she heard him say, “Wait-”
“Relax,” she said with a smile. “I’ll be back.”
Jessica stirred as a beam of morning sunshine fell across her sensuous face.
As she awoke she stretched her arms, causing the light sheet, which barely covered her naked body, to drift to the floor. Her eyes opened to the sight of her lightly tanned torso reflected in the large ceiling mirror. Her bright green eyes surveyed the taut 36D breasts with the large light brown nipples before moving down the soft, flat stomach to the trimmed tuft of auburn hair standing out from between her lithe and long legs.
She gently stroked one nipple into life before parting her legs to allow her fingers to gently open the vaginal flower which was already damp from the erotic dreams she had just awoken from. As her fingers soothed her soft lips her memory drifted back to twelve months ago.
Then she had been an overweight, frumpy forty two year old mother of two almost adult children who were now in their final years away at college. Her executive husband, Ted, had just left her for his bottle blonde twenty year old secretary who he had been screwing for the last six months.
She recalled stripping down in this same bedroom, feeling sorry for herself, and looking at herself in the dressing room mirror. It was not a pretty sight, with mousy brown unkempt hair, sagging breasts, rolls of fat under her chin and around her stomach, an ugly, hairy pubic bush above a dry unused and loose pussy with fat pock marked legs and arse all of which were a sickly white colour.
No wonder Ted had left her!
But he could have gently pushed her to do something about her appearance and not go screwing that Bimbo. This thought made her very angry and she decided to do something about it.
She enrolled in the local gym and took up a punishing training routine and diet which shed all the fat and firmed up her full breasts. She tanned her naked body naturally by her secluded pool at home, styled and coloured her hair to highlight her face and trimmed and coloured her pubic bush to expose her full pussy lips, which she tightened by taking up a series of erotic exercises using her experienced fingers.
Six months after starting her exercise routine she went to the local beach and stripped down to her thong bikini bottom with a small quarter cup string top. She slowly walked down to the water line and revelled in the looks and attention she received from the many attractive males on the beach.
She noticed Ted and the Bimbo lying on the sand and walked directly towards them. The Bimbo seemed to be filling out in all the wrong places which pleased Jessica even more. As she walked past them she said in a throaty voice that she knew excited him, “Hello lover. Too bad you didn’t stay.”
She felt a thrill as he opened his eyes and stared at her as if he had never seen her almost naked body before. She continued walking towards her towel when she heard him jump up behind her and take her arm, turning her towards him. Seeing the lust in his eyes she laughed and said “Don’t say anything Ted. I don’t need you any more. I just needed the satisfaction of seeing you drool over me once more, like you used to. Now go back to your Bimbo and have a nice life.”
She turned around, collected her towel and walked toward her car, feeling Ted’s eyes staring at her brown rounded arse.
Since then she had had a number of lovers but the last month or so had been very quiet on the sex front and her experienced fingers had been her only source of relief. Coming back to the present as her pussy started to wet her fingers she heard voices outside near the pool. Still playing with her moist cunt she walked over to the large window and saw Billy and his friend Jimmy who regularly cleaned the pool each Saturday.
Both boys were in their early twenties and only wore small racing costumes while attending their chores. Normally they would take a leisurely swim when they had finished. Jessica felt a new stirring as she looked at their tanned and muscular bodies and decided to see if she could seduce them and ease the burning in her pussy.
Jessica put on her white bikini thong and triangle top which barely covered her nipples. She knew that a hint of her pubic hair would show through the sheer material and her pert nipples would be clearly seen pressing against the top’s material. Grabbing a towel she timed her entry to the pool area just as the boys were working near her sun lounge.
She called out to them as she walked through the gate and was pleased to see both sets of eyes take in her almost naked tits and then her barely hidden crotch. As she walked towards them she noticed the outline of two soft cocks in their costumes and looked forward to getting to know them both a lot better.
She asked whether she would be in the way if she tanned herself on the lounge and they both agreed that there wouldn’t be any problem and recommenced their chores.
Sitting on the lounge she noticed that Billy and Jimmy were watching her out of the corner of their eyes. She even thought their cocks had thickened slightly causing a slight bulge in their costumes.
Now that she was sure that they were interested she lay on her stomach on the lounge with her legs slightly parted. Knowing that they were taking her body in she reached around and untied the top string, pulled it out from under her and dropped it on the tiles next to her. She folded her arms beneath her head and knew that Billy was getting a good view of most of her breast from the side while Jimmy would be getting a view of her arse with the thong just covering her pussy from behind.
Jessica glanced out of the corner of her eye and saw Billy just standing and staring at her sun covered body with an even bigger dent showing in his costume. She could not hear any movement behind her and assumed Jimmy was doing the same. Revelling in her newfound power over most men she decided to put her plan into action.
Raising herself onto her elbows she turned to Billy and asked, “Billy, would you mind getting my suntan cream from the small guesthouse at the other end of the pool. I seem to have forgotten to bring it with me and I really don’t feel like putting my top back on.”
Tearing his eyes from her swinging breasts he said breathlessly “Sure thing Mrs P, be back in a minute”
She watched him almost run to the guest house, adjusting his costume as he went, and disappear into the guest house. While Billy was getting the cream she asked “Jimmy would you and Billy mind putting some cream on my back and legs when he gets back so I don’t get sunburnt.”
Hearing a sudden intake of breath on her other side Jimmy said in a faint voice “I think we could manage that for you Mrs P.”
When Billy returned with the cream Jessica said in a sultry tone “Now I would like you both to put cream on my back and legs from either side, and I don’t want you to miss a thing. I also think you should call me Jessica from now on.”
Both boys smiled and looked at each other before squirting sun cream into their hands. Jessica lay her head back down on her arms as she felt two sets of hands rubbing cool cream over her shoulders, shoulder blades and along the top of her spine. They worked their way to the band of her thong then began on the top of her thighs and continued down each leg to her soft heels.
Jessica was sure that they were getting an eyeful and wondered if they noticed the damp spot which must be appearing on her skimpy costume. Not to worry, the thong wouldn’t be there much longer.
Just as they were finishing Jessica said “Now boys, you missed the area not covered by my costume!”
With a hasty “sorry” from both of them she again felt two sets of hands rubbing oil onto her arse cheeks with Billy working under the strap at the top while Jimmy began working in the crease where her cheeks and thighs met. She parted her legs a little further as Billy worked his way down to the top of her arse crease and Jimmy worked the sensitive skin alongside her wet cunt.
Suddenly Jessica said “Thank you gentlemen. I think you have covered everything.”
Disappointed, Billy and Jimmy removed their hands and stood up to go back to work when Jessica rolled over and sat up saying “Actually, you did such a good job I think you should be rewarded. Why don’t you both come over here?”
“Jimmy, you stand on this side and Billy you stand over the other side. I want you to close your eyes and fold your arms when you get here for your big surprise.”
As Billy and Jimmy moved over to Jessica’s beckoning hands they couldn’t help staring at her firm breasts and erect nipples. In return Jessica couldn’t take her eyes off the shape of their semi-erect cocks in their costumes.
When they were both standing alongside her, Jessica made sure their eyes were closed, slid her thong off with one hand then pulled both their costumes down before they could react. By the time they realised their dreams were about to come true Jessica had a firm, young cock in each hand.
Neither boy dared move as Jessica slowly ran her hands along each shaft, studying each penis with an experienced eye. She was pleased to see that although Billy only had an average six inch cock it was as thick as her wrist and would fill her cunt nicely. On the other hand Jimmy’s rod would have been at least ten inches long but a lot thinner. She was sure she would put both to good use.
She was also sure that they would not last long for now but would be quickly ready for action again. Sensing that they were unsure as to their next move Jessica said “I think you should give my tits a good rub while I ease up your tensions.”
Each boy leant over and began playing with her breasts and nipples which sent a wave of pleasure through Jessica. She opened her legs wider, allowing them a good view of her wet pussy lips, which kept them nice and hard.
She slowly ran her hand along each cock in synchronisation and leant over to lick the precum from the head of each one in turn. Each time her tongue touched their sensitive flesh they moaned with delight and she could feel their bodies stiffening as they neared orgasm.
Jessica quickened her teasing strokes and Billy and Jimmy both stood up straight as their hot cum began to shoot up from their balls and out of their shafts. Jessica aimed one rod to shoot its seed over her hot breasts and the other to cover her pussy hair and cunt lips. Strands of white cum flew out of the two stiff cocks and landed on Jessica’s body from her neck to her thighs. At the end of their ejaculation a small dribble was forced out of each cock by her rubbing hand and Jessica licked it from each reddened staff, enjoying the taste of their pure cum.
Sure she had taken every drop, she released their now half erect phalluses and rubbed their cream into her body. She then stood and gave each a long tongue kiss, giving them a taste of their fluids before saying “Let’s go for a swim.”
With that she dived into the pool closely followed by Billy and Jimmy.
The two boys surfaced after Jessica and saw her in the middle of the pool, floating on her back. The remaining cum on her breasts and stomach glistened in the sunlight and they could just make out her pussy hair above her hot slit.
She drifted to the shallow end of the pool and stood up to face them. The surface of the pool lapped around her knees and she threw her head back which forced her breasts to press forward, accentuating the large erect nipples. One hand began rubbing her perfect chest while the other snaked its way down over her pubic hair and onto her pussy which was not only wet from the pool.
Both boys began walking toward her, their semi erect poles slowly coming into view as their bodies rose out of the water. Billy arrived first and took her in his arms, tongue kissing her while he pulled her close to his body. She could feel his thickening cock pressing into her lower stomach and knew she had to have it in her hot cunt.
Suddenly, Jimmy began kissing her on the back of the neck while enveloping both Jessica and Billy in his strong arms. He was only slightly taller than Jessica and she could now feel his thickening rod rubbing along the top of her crack between her arse cheeks. She was now sandwiched between these two gorgeous hunks and could feel both cocks hardening against her tight body as they rubbed against her in passionate embrace.
Then they both started to kiss their way down her body taking their stiff pricks away from her but causing her to lose control at the sensations of lips simultaneously licking both her tits at once.
While Billy had worked his way down her neck to the soft orb on the right of her chest Jimmy had worked his mouth across her back and under her left arm to lick along the other orb, reaching his destination at the same time as Billy. Both sucked the large brown nipples into their mouths and greedily licked around the flesh held in their mouth. Jessica moaned in ecstacy and played her fingers along their strong backs while they ran their hands over her arse cheeks and soft lower stomach.
Releasing one tortured nipple Jimmy recommenced his journey down the underside of her tortured breast, kissed across Jessica’s hip and stopped just where her cheeks began to form that delightful channel which ran between her legs. He used his hands to separate her cheeks and tongued his way towards her tight arsehole.
This forced Jessica to involuntarily push her stomach and pussy out as Billy began to lick down over her navel to the very top of her finely trimmed pelt which lead to her saturated pussy. He greedily nuzzled the soft hair while Jimmy swirled his tongue around Jessica’s rosebud.
Unable to focus with the pleasure she was feeling, Jessica’s legs began to give way and Jimmy stood and took her swaying body into his arms. They had moved further into the pool during their ministrations and the water was now up to the top of Jessica’s thighs. Jimmy eased her body back while Billy sank to his knees between her legs and floated her body while supporting her backside with his hands.
This meant that her head was just beneath Jimmy’s tight balls and erect cock while her pink pussy lips were just below Billy’s hungry mouth.
Billy held her up with one hand while his fingers on the other hand moved over her soft fur to the fleshy pussy lips just waiting to be sucked and licked. Billy was still technically a virgin although he had sucked a number of pussies over the last few years. However this was usually in the back of a dark car and this was the first cunt he had seen up close.
He was fascinated by the folds of skin resting over each other near her pubic hair but which separated slightly as they ran further down to where her entry to paradise lay. His fingers gently separated the slightly crinkled flaps, causing Jessica to moan louder, which revealed a large penis like clitoris which appeared to be as erect as his cock. His fingers moved down her slit and left the flaps parted for entry to her pink hole which was soaked in lubricating juices.
As Billy began licking and sucking the lower part of Jessica’s vagina, Jimmy slowly moved her around so that he was at the deeper end of the pool. This allowed the water to come up to just under his aching balls and meant that Jessica was at just the right height to use her mouth on his cold tightened balls and engorged cock.
She put her arms around his hips and pulled him until he was just standing over her upturned face. She sucked at his bags full of semen and licked between his legs to his arsehole and back before nuzzling the tight skin which hung from his engorged cock. She managed to suck one tight nut into her experienced mouth and gave it a tongue massage before releasing it and pulling her head up to engulf the lower part of his phallus in her hot lips.
As she nuzzled the large cum channel on the bottom of his cock Billy moved up to take her clit in between his lips. He slowly sucked and tongued the sensitive flesh until Jessica released Jimmy’s throbbing shaft and screamed in orgasmic delight as her body stiffened in response.
Breathlessly, Jessica pleaded with Billy to put his thick rod into her wet cunt as she took hold of Jimmy’s erect phallus and slowly pumped her hand along its glistening length. Billy took her hips in his hands and stood so that his cock was just above her soaked pussy. Lifting her body slightly, the length of his shaft settled between her pussy lips with the bottom of the large head resting on her erect clitoris. He slowly pumped along the wet channel and over the sensitive knob of flesh until Jessica began another orgasm. She lifted her lower body further out of the water and impaled herself on Billy’s thick rod, her hot cunt swallowing his shaft until his cum filled balls slapped onto her arse.
As both boys had only just ejaculated they knew that they could now remain erect for a long time before needing to again release their seed. Billy began to slowly fuck the tight cunt enveloping his shaft by withdrawing until the tip of the head only just remained between the soft lips then pushing back in until his entire shaft was again up to his balls in pussy meat. Meanwhile, Jessica’s fingers on her free hand toyed with her clit and pussy as well as occasionally flicking his slowly moving rod. She was amazed at how full her cunt felt and could feel every twitch of his thick shaft.
Meanwhile Jimmy lifted her face back up to his hot balls which hung low from his erect shaft. Jessica sucked one between her moist lips and ran her tongue over the soft skin and hard nut while still masturbating him with her hand. She then managed to take the second one into her mouth and felt Jimmy stiffen at this totally new sensation as her tongue and lips massaged his sensitive sacs.
After some sensual minutes Jessica could feel the sun burning into her exposed skin and decided that this tryst would need to be continued under cover. Releasing Jimmy from her mouth she reluctantly pulled away from Billy and stood unsteadily again between her two lovers.
Both cocks stood straight out from the boys’ bodies and Jessica grabbed each as she began to walk towards the pool steps. Stopping at the steps, she released their hard shafts and gave Billy a long passionate tongue kiss followed by another with Jimmy. She then turned and walked towards the pool hut without saying a word. Both boys watched her tanned naked body for a short time before following her into the cool hut.
As they entered the hut their eyes took a few seconds to adjust to the semi darkness. As their eyes adjusted they noticed a small bar, casual lounge and chairs and a large sheet covered rubber mattress which was usually used for unexpected guests staying overnight.
Jessica had knelt in the middle of the mattress and sensually licked her lips as she prompted them to join her. Both boys knelt on the mattress and slowly crawled toward Jessica, who now lay back with her arms and legs both outstretched in wanton abandon. Jimmy and Billy lay on each side of her and began to suckle each of her enlarged nipples while she rubbed her hands gently over their backs pulling them closer to her hot body. A tremor of excitement ran through her when she felt the heat of their engorged phalluses press against her soft thighs.
Jessica could feel the hot juices flowing from her expectant pussy and knew it was time to release the sexual tension built up in the core of her body. She took Jimmy from her breast and kissed him deeply before pushing him onto his back and then did the same with Billy. Both of their erect pricks pointed to the ceiling and Jessica took each in a hand moistened by her pussy juices and began to slowly masturbate them.
Neither boy moved and she knew they were still totally under her control. With a squeeze of Jimmy’s soft balls she rolled over onto Billy and worked his thick cock into her soaked pussy then lay almost motionless as one hand took her hot fluids from his large cum sack and moistened her arse hole.
The week had been a complete bust. You traveled all the way from the UK to the Caribbean for a week of business meetings and some relaxing in the sun. It ended up that the week was spent is crisis management. The up side was that everything was back on track with work with no ill effects. The down side was that you ended up spending all of what was planned to be spare time in meetings so you spent no time by the pool or on the beach. Last night’s meetings went late and you have an early flight back home. To top things off, there was a mix up with your return flight and you were the only one in your group to get bumped from your flight home. The next flight was booked, so it would be another day before you could get home. Maybe this would be a chance to relax before heading home. You have until the next day before you flight out.
You catch a taxi back to the hotel where they sadly inform you that you former room has been booked, but to you surprise and delight, they say they will comp you a suite because you company often uses their site for meetings. You quickly make your way to your 3rd floor room and generously tip the bellman, strip and put on your bikini and practically run to the pool. It’s early afternoon in the heat of the day, and you order a cocktail from the waiter. You lay on your back and relax in the sun letting the tension melt out of your body as you quickly drink down your cocktail and order another and drink that one. You hear a deep voice and open your eyes, but all you can see is the bright sun around a silhouette. “Excuse me,” you say.
“I noticed you were sleeping and you may want to get out of the sun or put on some sunscreen before you burn. The Caribbean sun can be brutal,” the voice says. You hadn’t realized you had fallen asleep and thanked the silhouette as he moved away toward the pool.
Since you didn’t want to sleep or burn, you decide a quick dip in the pool will wake you before turning over. The water is cool, almost cold, against your hot skin but feels good and refreshing. The hot/cold contrast makes your aureoles pull tight and your nipples harden. Not many people are around so you don’t worry about it. You swim up to the bar and that’s when you notice him. He is facing you. You can sense him staring at you from behind his sunglasses. He’s standing in the pool with his back against the bar. You swim up to the bar and get some water and another cocktail. “I hope you don’t mind that I woke you up. It would be a shame for you to get a sunburn.”
You turn to face the voice, smile…”Thank you.” Now that you are in the shade you can see him much better. Taller than you, he’s about 6′ tall, with broad shoulders and chest and a hint at what used to be six pack abs. You mention that you are glad he was so kind and you didn’t realize you had fallen asleep. When he pulls up his sunglasses you are taken in by his dark brown eyes that match his brown skin. Internally you suppress a shutter that runs from your clit to your nipples as you imagine pulling on his bald head as you feel his tongue and mustache against your pussy.
After a quick chat, you find out he’s here to check out the hotel for possible use as a conference site. You explain how poorly your week went and want to get back in the sun as you swim back toward you lounge. Within two min of getting to your lounge a waiter brings a bottle of sunscreen to you with the compliments of the gentleman at the bar. You smile a thanks to the mysterious gentleman. He smiles back and then turns his attention to the bar. You massage the lotion into your legs, arms, and stomach. As you apply the lotion to your chest, you notice that very few people are around and no one is looking at you. You take the opportunity to undo the back of your bikini top then the neck. The cool breeze hardens you nipples and keeps the top from falling by clinging to them. Your breasts aren’t huge but they are large and nicely shaped and you are proud of them. They sag a little more than you wish, but that happens. You are often told that you have the breasts of a woman 10 years younger. You then notice out of the corner of your eye that the man has moved to the deeper end of the pool closer to you but all you can see it the back of his bald head. The image of seeing his shining dark head moving between your legs flashes through your brain and your nipples harden more and your clit throbs. You pull off you bikini top and rub the lotion into your breasts. As you rub over your nipple, it stick out further and you close your eyes and imagine again if just for a second. When you open your eyes, you see that he has turned and is staring at you behind his sunglasses. You feel emboldened and continue to massage the lotion into your breasts. With your front protected from the sun, you face your admirer and offer the bottle to him, “would you be kind enough to do my backside?” as you smile wickedly to him.
Without a word he emerges from the pool and you force yourself not to stare at the bulge in his shorts. You turn and lay on your stomach. You hear his rich voice suggest moving to the whirlpool area because of the angle of the sun. That sound good to you. You follow him to the new location and see that you can get a better angel on the sun; it is also partially secluded by low shrubs and bushes. You find a lounge and lay down on your stomach. Shortly, you feel warm hands glide over your back and shoulders massaging the muscles. He uses a liberal amount as he rubs lower and lower until he reaches you bikini bottoms. He then begins to work his hands over you from your ankles up. His touch and your thoughts keep your nipples hard and you begin to feel your pussy begin to leak.
He works both calves at the same time, then continues up your thighs. He boldly progresses up your thighs to your ass and slips his hot fingers just under the edge. Until you have been able to stifle you moans and keep your body still. A short moan escapes and turns into a long sigh. He traces along your bikini. You submit by slowly parting your thigh slightly and barely raising your hips toward him. He notices and moves his fingers along your bikini down between your thighs and back out. Your pussy is on fire. Without a word he slips a finger under your bikini and moves again toward your pussy. You arch you back in anticipation and submission. Your wish is granted when you feel his finger trace down the crack of your ass and down to your soaking pussy where he slowly pushes into you. Your moan escapes. A low long sound much louder than you wanted.
He continues to work his finger in and out of your pussy. You feel every movement of his finger as it continues to bring you closer to climax. He adds a second finger and it almost pushes you over the edge. Your breathing comes in gasps as he works you with his two middle fingers. It takes you by complete surprise as he flicks your clit at the same moment he brushes a finger over your tight asshole. Involuntarily, you moan again and push against him. He obliges you with the tip of his finger pushed into your ass. You cum hard. Gasping for air, pushing your ass high in the air hoping for more. Your pussy is leaking, and you feel it combined with the lotion and sweat drip from your pussy onto you bikini. You body convulses several times as you struggle not to scream out. After what seems like forever, the climax subsides. He slowly pulls his fingers out of you and you lie there with your eyes closed trying to recover.
When you turn toward him, you see him just getting into the whirlpool. He looks back at you and smiles as he leans back and relaxes in the warm water. On unstable legs, you walk to him, lower yourself into the water, sit on his lap, rub your hands over his head and pull him to you as you snake your tongue into his mouth. You move to straddle him and can feel his hardness against your ass. Without breaking the kiss you reach down to pull your bikini aside, manage with his help to free his formidable cock from his shorts, position his cock at your pussy and slowly lower yourself onto the best feeling cock you had in quite some time. It feels like you descend forever when finally you feel full just as you get to the end.
Finally you break the kiss as you start to grind down on the hard cock that is stretching your pussy. Through half closed eyes you look down at him then pull his face to your breasts. Your nipples harden even more when he takes one into his mouth. You feel his teeth begin to gently bite down. It causes a tingle to travel from your nipple to your clit and you open you eyes. You see three male employees watching from over at the bar. You had forgotten where you were. The bushes only kept you hidden on three sides. You immediately try to get up and say you are being watched. Just as you are about to pull the head of cock out of your pussy, he quickly grabs you by the hips and pull you back down. When you hit bottom you can feel his cock against your cervix. “We’ve got to get up, they’re watching us,” you plead.
“Let them watch,” he says calmly, “just enjoy the ride and relax.” And with that he lifts you again and pulls you back down hard enough to make you full boobs bounce. Once again he nurses at your nipples and you begin to melt again as your lust for him is renewed. The heat of the sun, the drinks, the warmth of the water, the teeth on your nipples and the cock sliding in and out of your pussy is too much. You melt as your orgasm makes your body contract repeatedly until you have no strength left. You lean into him and rest. He lifts you off of his cock and holds you as you catch your breath.
With much effort, you both climb out of the pool and wordlessly grab towels and he follows you to your suite. Once in the door you turn on him and kiss him deeply and trail kisses down to his neck, nipples and lower until you are on your knees in front of him. You reach in and pull his stiffening cock out as you pull his shorts down. It’s big, medium brown, and nicely shaped. It will be a challenge but you want to try to take all of it in your mouth. You lick around the head and it bobs up and down and gets bigger with every beat of his heart. You open your mouth and push forward to take most of him; pull back leaving it wet and push back to get the rest of him in you. It feels good to have your mouth full of cock. It is then that you realize that he is still growing in your mouth and you must pull back. You feel his hands on the back of your head and you go down on him again. His cock is to big for you to take easily now. You suck, lick and slurp as much as you can. You feel your pussy begin to drip again and your hard nipples rub against his legs as you suck on his cock. His hand urge you to take more cock in your mouth. You open as wide as you can, grab his ass and pull. His hands push against the back of your head as you relax your throat to accept his cock. You feel proud as your nose pushes firmly against his pubic bone. You took it all and it feels smooth and warm.
He pulls you up and you reluctantly let his cock fall out of your mouth. He walks you to your balcony and you feel the heat blast you in the face despite the shade. He leads you to the rail, faces you toward the ocean, pulls your bikini off of your legs, knees behind you and pushes his face into your pussy from behind. You immediately push back and down to get as much of his tongue in you as possible. You lean forward into the balcony and you can see his cock waving in front of him as he sits on his heels with his face in your ass and his tongue in your pussy. As you settle in for a nice ride he abruptly stops and stands up. You feel his cock brush against you bare pussy lips. His cock rubs around your wet folds. You bend over further to give him better access. Once again you feel his cock part your pussy and stretch you once again. You are not in control of this fuck. He continues with short stabs until he is buried in your pussy then continues with long slow strokes. The heat builds in your pussy. You feel his hands all over your ass and hips. Without warning you feel a searing pain on your ass and hear a crisp crack. The slap on your ass causes you to cry out and push back at the same time. He rubs the spot where he spanked you and then smacks it again. You feel his fingers moving closer to you asshole and this causes you to squirm with even more pleasure. His finger part your crack and begin to probe your ass. The wetness of your pussy and the sweat make it easy for him to push into your ass. You feel empty when he pulls his cock out of your pussy, but you feel him drag his wet cock to line up with you ass. Without thinking, your reach back and pull your ass apart. Your excitement about getting ass-fucked by him is slightly tempered by the size of his cock.
Gently he pushes forward. You feel the familiar sensation of being opened for the first time all over again. You pull harder with your hand and push back. You can feel as the head finally opens you enough to push in. The fullness overwhelms you, and he is not even halfway in you. He stays still as you catch your breath. Just as you relax, he smacks your ass again and pushes hard. One of his hands grabs your shoulder and pulls while the other assaults your ass with smack. You then realize that you don’t know how long or loud you’ve been moaning. The fullness in your ass and the forceful strokes are too much. Your climax engulfs you. It starts at your toes and works up to your pussy and ass then radiates from there up your body. You pussy is actively dripping, your ass in clenching your nipples are as hard as they have ever been and you can do nothing but moan and pant as his wonderful cock strokes in and out of your ass keeping you at the peak of your orgasm. He feel his strokes come faster and harder as your hear him grunt. Your ass feels tighter as you feel his cock swell before you feel the heat of his cum enter your ass. You cry out again and have to hold on tight to keep from falling to your knees as your orgasm leaves you weak. He pushes deeply until he can cum no more.
His strong hands massage your back and shoulders as the two of you recover. He slowly pulls out of your ass. You feel empty and your feel his cum begin to drip out of your ass. You look back just as you see him sit at the balcony table. You walk over to him, kiss him, knee in front of him take his cock in your hands as you suck his cock back into your mouth. As you grip him with your mouth you notice your wedding ring. If only you could get fucked like this at home. With luck he’ll stay with you all night long. You figure one indiscretion will be alright.