Ann had tried to leave her old self behind since she’d married Jimmy. Sure, she’d let Lance seduce her into meeting him shortly after she and Jimmy returned from their honeymoon but she’d felt so guilty about that she’d remained faithful ever since.
But as they’d gotten into their third year of marriage Ann was feeling less and less satisfied with their sex life. It wasn’t that they didn’t do it at least twice weekly, it just wasn’t as satisfying. She wondered also if it had anything to do with Jimmy’s increasing interest in cross dressing.
She’d thought she detected her clothes being out of order and had set up a web cam to watch their bedroom. Sure enough, as she watched from her office browser, she’d seem Jimmy come home from work and get dressed in her clothes. She noted that he usually masturbated while dressed in her panties and bra.
She’s also seen him get dressed in one of her shortest dresses and go out of the house dressed in a blonde wig and 5-inch fuck-me heels. With his slight build and hairless body, he could easily pass as the girl-next-door. Jimmy had a tracking device on his car so Ann had checked where he went when he went out of the house. She discovered he went to a bar and then to a nearby adult bookstore. She let her imagination run wild as she tried to guess what he did at the adult bookstore after getting some liquid courage at the bar.
He also seemed to enjoy his crossdressing when on business trips as she found numerous pics of him dressed and sometimes not dressed. She wondered who had taken the pictures.
“He does seem to make a nice looking girl,” Ann mused as she and Jimmy walked Orient Beach in St. Martin.
Orient Beach is the popular nude beach and she and Jimmy had joined many others in shedding all their clothes. With all those penis’ on display Ann was reminded of how small Jimmy was. She knew that for the six years they went together before getting married what kept her satisfied were her many secret affairs and flings.
Still she loved him and knew she’d never seek a divorce. His high paid job provided them with a good standard of living. Now with all these good looking hunks with big dicks as reminders she wondered if she’d ever be satisfied with Jimmy’s four inches.
“He is good with his tongue though,” she laughed to herself.
“Hey, let’s go to Pinel Island today,” Jimmy suggested.
Even with all the nakedness on Orient Beach there were no public displays of affection and certainly no outright sex. But Jimmy had heard that you could take a boat to a nearby island and find deserted beaches where you could have sex in the open. Ann thought maybe that would rekindle their love making.
“OK, let’s find a boat,” Ann eagerly replied.
They quickly found a boat manned by a black guy who was also naked and had 12 inches of cock handing down his leg. Ann couldn’t imagine what it would be like hard.
“I guess this is where the phrase ‘hung like a horse’ originated,” Ann thought to herself.
His name was Thomas and he took Ann’s hand as he brazenly looked her up and down. Ann’s 5’3″ trim frame with 36C breasts and a 24 inch waist must have pleased him as he said, “Well, well, well, little lady, looks like Thomas got him a beautiful ride today.”
Ann blushed but was secretly proud of her looks. She knew her short black hair, shapely legs, and shaved pussy attracted the looks of many men.
As Thomas helped Jimmy aboard as well, he thought to himself, “Looks like the boy could use some help in the bedroom,” as he eyed Jimmy’s small cock.
Jimmy brought a backpack with some beach towels, suntan lotion, and some water. When they got to the island they discovered a small beach bar with a number of people hanging out on the sand eating and drinking.
“How about a beer before we take our hike?” Jimmy asked.
“Yes, let’s, I’m really thirsty from all this sun,” Ann agreed.
“Let’s grab these two lounge chairs and I’ll go get the beers,” Jimmy suggested.
“OK,” Ann readily agreed as she lay back in one of the lounges.
As she lay back she noted that she was being appraised by three well built black guys who were sitting on the top of a nearby picnic table. With their feet on the seat their cocks were on easy display for Ann. Deciding that she’d give them an equally good view, she spread her legs slightly giving them an unhindered view of her pussy lips.
Ann watched them carefully through her sunglasses. She knew for sure they were talking about her and she felt the warmth in her pussy as she basked in their gaze.
Jimmy quickly returned with two Heinekens and sat down beside her in the other lounge chair. Ann saw one of the three black guys node in their direction and say something to the other two.
If Ann could have heard them, she’d have heard Derek voicing a thought similar to Thomas’ earlier one, “I think that boy could use some help satisfying his sexy lady there. She is one hot piece of ass. I know she intentionally opened her legs so we could see her pussy lips.”
The other two nodded in agreement.
Finishing their beers Jimmy said, “Let’s go baby, I’m so ready for you.”
As Jimmy took her hand they walked within three feet of the admiring back men. Ann noted that Jimmy was indeed ready for her with his cock already hard. She also noted that Jimmy’s hard cock was still much smaller than any of the three soft cocks on display for her.
As they passed the three guys she heard one of them murmur, “Umm, umm, umm,” causing her pulse to quicken.
After a short 10 minute walk they came to a deserted beach and spread a large beach towel. They quickly lay down, removed their sun glasses and began kissing while passionately touching each other intimately.
“Oh baby, I want to feel your cock in me. I want to take our time and just fuck and fuck,” she continued, not mentioning that Jimmy had been cumming quick quickly in their recent fucks.
Ann was very aroused and knew she had multiple orgasms in her today. She didn’t want to miss any of them. Jimmy dipped his finger into her and caressed her clit. He didn’t realize when he felt her soaking pussy that it wasn’t his finger but rather all the big cocks Ann had seen today that made it so wet. Jimmy rolled between her legs and inserted his full four inches into her.
“Oh yes honey, fuck me!” Ann commanded loudly as she bucked her hips in anticipation.
Her wild thrusting caused Jimmy to loose his connection a couple of times but they nevertheless kept this up for three or four minutes before Jimmy announced, “I’m cumming!”
“No, not yet honey, please wait!” Ann implored but it was too late.
Jimmy had already shot his load into her. His rapidly deflating cock gave Ann nothing to fuck so she started fingering herself.
At that moment, as Ann lay with her eyes closed and legs spread wide, she heard,
“Well, well, well, I guess we’re just in time to help our ‘little’ friend out,” chuckled Derek as he looked down at Ann’s wide spread legs and Jimmy’s shriveling cock.
“Hey you guys leave us alone,” Jimmy demanded.
“Well it looks to me like the little lady is in need of a good fuck and we’re here to help,” said the second man, “I’m Kevin, that’s Derek, and over there is Todd.”
“That’s my wife you’re talking about,” shouted Jimmy as he tried to push Kevin away.
Jimmy couldn’t budge the muscular Kevin.
Grabbing Jimmy’s arms Kevin handed him to Derek and Todd and said, “Tie him to that tree so he can watch his wife get a real fucking.”
“She doesn’t want you fucking her. She’s my wife,” Jimmy kept insisting as his arms were tied behind a nearby palm tree.
In spite of Jimmy’s protestations the three men noted that Ann made no attempt to cover up and kept her legs spread the whole time.
As Derek kneeled between her legs, she finally made a feeble, “No, no, please…”
Her weak response ended as she felt the head of Derek’s big cock enter her pussy.
“Tell them ‘no’ Ann, stop them,” Jimmy implored her as he saw her about to be taken by Derek.
His entreaties and tearful eyes seemed to be answered by a look of lust in Ann’s eyes. As Derek sank his big cock into her she dropped all pretense of reserve and thrust her hips up to meet him.
“I told you she would be a hot piece,” Derek told the other two as he began to pound Ann’s pussy.
“Oh fuck, oh fuck, oh fuck,” was all Ann could say as she continued to meet each of Derek’s thrusts while he pinched her nipples making her even hotter.
After 15 minutes of this pounding Ann screamed, “Oh Derek, fuck me hard, plant your seed in me, I’m cumming….”
With this note of Ann’s complete surrender to what was happening, Jimmy could only watch helplessly as his wife was fucked by this powerful man. After another half hour and countless orgasms by Ann, Derek finally thrust deeply into her and held it there as he shot his seed deeply into her womb.
“Oh baby, you are so hot,” he exclaimed.
After Derek, both Kevin and Todd had their way with her. Kevin had the biggest cock by far, almost as big as Thomas on the boat. Ann continued to have orgasm after orgasm for over two hours. As Ann lay exhausted on the towel with her legs obscenely spread and cum oozing out of her pussy, they untied Jimmy’s arms.
“Get down and lick her clean,” Derek demanded.
Jimmy tried to resist, “I’m not going to eat cum,” he squeaked loudly sounding just like a young girl.
Derek grabbed his ass in his strong hand and lifted him in front of Ann. Pushing his head down with his other hand he forced him into position.
“You’ll eat that and do a lot more before the day’s over,” Derek told him.
With that Derek stuck his finger in Jimmy’s ass and said, “Since you don’t have much of a dick, maybe we should fuck your ‘cunt’ here.”
“I’m not gay,” Jimmy exclaimed for a brief moment before his mouth was forced back down on Ann’s cunt.
To Jimmy’s surprise, the taste of cum was pretty good and he began to suck on Ann to get more out. With his ass in the air Jimmy was a good target as Todd moved behind him and began fingering his ass. When Jimmy tried to protest, Kevin and Derek held him down and made him continue cleaning up Ann. When Todd felt like he’d loosened Jimmy up with his finger he nudged his cock head up to Jimmy’s ass and eased it in. Jimmy’s protests were muffled by Ann’s cunt.
Wasting no time Todd rammed his cock deeply into Jimmy’s ass. Todd continued to pound away unmercifully in Jimmy’s virgin ass. Everyone noticed that at some point Jimmy quit resisting and thrust his ass back to meet Todd’s powerful thrusts.
“Looks like your little hubby likes having his ass reamed,” said Kevin to Ann as they watched.
Kevin had his arm around Ann and was playing with her tits. Ann moaned in appreciation and turned to kiss Kevin. Their tongues met and Ann’s passion mounted. As Todd gave a final ram into Jimmy’s ass his cock erupted and some cum leaked out around Jimmy’s asshole.
“My turn,” said Derek as he plunged into Jimmy’s ass without giving the poor boy time to recover.
But again Jimmy seemed to like it as he met Derek stroke for stroke. Ann in the meantime was sucking Kevin’s huge cock, bringing it back to full attention.
As Derek shot his load deep into Jimmy, Kevin said to Ann, “There’s be more for you later but I need to try that tight white ass of your hubby.”
“Ohh, no, it hurts,” said Jimmy as Kevin’s big dick impaled him.
His tears of pain quickly turned to tears of pleasure as he adjusted to Kevin’s big size and began to enjoy it. As Kevin exploded in him, Jimmy’s little dick squirted out a stream of his own.
“I told you your hubby likes being fucked,” Kevin boasted to Ann as he pulled out and left Jimmy in a weak heap on the ground.
Sobbing softly Jimmy knew that all pretense of his manhood had been lost to his wife. He had been humiliated by these hunks and knew that she would never be satisfied with his little cock again.
The three guys went into the ocean to clean us and Ann lay down beside Jimmy to soothe him, “Don’t worry honey, I’ll never leave you. I just know I need to lead my own sex life. Besides, maybe this will give you a chance to confront your cross dressing to it’s fullest.”
“What, you know about that?” Jimmy asked incredulously.
“Yes, I’ve know for some time that you or someone was going through my clothes so I setup a webcam. I’ve seen all your activities including your outings to the bar and adult bookstore. Frankly honey I think you make a great girl and by what I just witnessed I think I know what you’ve been doing on your outings,” she continued.
“Wow, this is a lot for me to absorb,” Jimmy said as he finally got up.
“Let’s go in the water with the guys,” Ann suggested.
“OK,” said Jimmy tentatively, “I hope they won’t hurt me.”
“Don’t worry honey, they all want a piece of your tight ass again,” she responded.
As they played in the water with the three guys Jimmy relaxed and thought about his new opportunity to be open about his desire to be a girl. He realized as they played around in the water that he was being treated as a feminine sex object, something he’d only been dreaming about. The five of them walked back to the beach bar and had a drink together.
Jimmy blushed as Kevin toasted, “Here’s to the best white ass I’ve had. And the best white pussy,” as he turned to Ann, “If you want some more of this, meet us at that beach bar with the purple umbrellas.”
Jimmy and Ann walked down to find Thomas waiting for them.
“I hear the little lady has learned what a real man can do for her,” he said brazenly.
“We both did,” was Ann’s quick reply.
“Well, maybe before we make the journey back, you could let Thomas have a sample of that smooth pussy,” he suggested.
Ann practically drooled at the thought of taking Thomas’ 12 inch cock. As Ann looked at this cock she realized that hard it must now be 14 or 15 inches. Could she really take all that? Thomas pulled her close and kissed her passionately as he started to finger her pussy. Ann’s juices quickly let Thomas know she was ready. Turning her quickly around Thomas pushed her to a doggie position.
“The only way you’re going to take all this is in this position,” said Thomas, assure of himself from years of fucking.
Thomas plunged into her and began pounding away. He would pull all the way out and then plunge all the way back in. Ann couldn’t believe the intense feelings she felt.
“Oh Thomas, fuck me like the bitch I am,” she screamed, not realizing that most of the crowd from the bar were now watching Thomas penetrate her. Jimmy stood off to the side, not sure of his role in their new relationship.
“Oh, oh, oh, ohhh, Thomas, you are so fucking good,” Ann screamed as she orgasmed again and again.
With that Thomas plunged his cock deep into her and came in a long intense orgasm. Ann couldn’t believe how long she could feel Thomas cum going into her.
“Geez, it feels like a gallon,” she thought, “He may make me pregnant in spite of the pill.”
As Thomas pulled his long cock out of Ann, the crowd gathered around could see how slick it was with both their juices. Jimmy watched in amazement that Ann could have taken such a monster.
“Want to feel what just gave your woman so much pleasure boy?” Thomas asked Jimmy.
Jimmy couldn’t believe he was doing it but he reached out his hand and touched it. He couldn’t even close his hand around it.
“Why don’t you use that mouth of yours and clean Thomas up?” Thomas asked Jimmy as he put his hand on Jimmy’s ass and propelled him closer.
Figuring that all pretense of his manhood had already been lost, Jimmy did as he was told, licking up and down Thomas’ long cock and sucking the head to get the last drops out.
He wondered what the future had in store.