Tan Lines and High Heels

Jessica didn't know if she would even be able to walk the short distance to the other store dressed like this. Or undressed like this. She sat down next to the mirror and put her head in her hands. She was on the verge of tears, realizing how uncomfortable she was with her body, with her age and with her celibacy. But before it could all crash down on her, she heard the young man walk up to her.

The next five minutes changed a lot of things for Jessica. Some she would realize immediately, others she would only understand weeks later. Despite his broken English, the young man began by asking her if she was working for Matthias. At first, because of the way she looked in this ridiculous bikini, Jessica thought that Matthias was a pimp. But soon she understood that he was a photographer.

When she tried to explain that she wasn't a model at all, the young man frowned, clearly puzzled. He thought she had been trying those bikinis for a shoot. Jessica could see in his eyes that he wasn't just saying this to compliment or comfort her. He really believed that she was a model. He even told her that Matthias often chose models with tan lines as he thought it sexy. When she said he must be the only one to find that sexy, the young man smiled shyly, shaking his head.

After a moment he walked back to his counter and let Jessica alone. She stood up, took a deep breath and decided that she could, at the very least, find the courage to walk out to the next store. As she walked to the counter, barefoot, she remembered that her flip-flops were missing as well. Looking around the shop, all she could find were high heels. "Of course... Right..." she thought, cursing herself for this crazy idea of looking sexy.

A few minutes later she took a deep breath and walked out of the shop, looking sexier and sluttier than she had ever had in her life. "Here comes the MILF, guys, look at me!" she thought, trying to make light of the whole thing.

Strangely enough, if the young man's comments about her being a model had given her enough courage to get out, the walk to the other store had a much more transformative effect. In those few minutes, she got more appreciative stares and whistles and offers for drinks than in all of last year at home! At first she was ashamed and even a bit afraid: she was, after all, dressed like a slut. A bikini way to small for her breasts, her unmissable tan lines and a pair of red high heel shoes. A slut begging for attention.

At home, the only guys that would have openly ogled her, or whistled like that would have been creeps. But here, things were different. From what she could see in the eyes of the men around her, they were not creep. Just men being men, letting her know how desirable and beautiful she was. Just basic, primal male-female interactions. She had bee afraid at first, but despite how explicit some of them were with words and whistles, she hadn't felt threatened by any of them. They kept their physical distances even though their intentions were made clear.

It was a very strange and powerful experience. She had never felt as much of a woman before in her life. Ever. Even when she was being regularly courted before marrying. In her mind she looked like a slut, yet she was getting another vibe from the men. There was nothing vulgar, like what she would probably have gotten at home. Instead, she got a bunch of explicit compliments on her beauty, her sexiness and even a few thanks for allowing them to see her body. There was no explicitly sexual comment, nothing lewd or obscene.

Jessica couldn't deny that her body was beginning to warm up real fast. The raw compliments didn't simply boost her confidence and didn't simply make her feel more feminine. Oh no. It also made her blood race in her veins and it made her feel alive as sexual feelings began awakening.

The high heels, something she had never really worn, grew on her really quickly. It forced her to change her gait and soon she found a new way of walking that enhanced the movement of her hips and made her large breasts sway. Her pelvis rotated more, her strides shortened and she felt her body bouncing a lot more than it usually did when she walked. All in all it felt, even to her and obviously to the men looking at her, extremely feminine.

By the time she arrived at the other store, she paused for a moment. She still felt very strange being dressed like this on the street. The sun had turned her already bright tan lines into blinding light bars! Yet those comments... and the way they had made her feel...

It was as if she had woken up from a puritan slumber, as if the real woman inside her had suddenly burst out. Looking around, she saw one man looking at her, a grin on his face and a fire in his eyes. As she stared at him, she was shocked to feel that her bald pussy was even beginning to feel much hotter and wetter! Smiling, she winked at the man and turned away from the store. If she was going to give dating and chance here, might as well go all in!

Back at the hotel, Lew still couldn't believe he had stolen his mom's bikini! He had sneaked in the store and grabbed it, as well as her flip-flops, before sneaking back out. He hadn't seen any of the bikinis his mother had tried on, as he didn't want to risk being seen, but he knew he had to force her hand. The shop was pretty much a sex shop, and the bikinis he had seen on the stands were way too sexy for his mom.

And so he had grabbed her bikini and had thrown it into a garbage bin, forcing her to buy one. As much as he wanted to see which she would pick, he had decided against it and had run to another store to buy a speedo. It would be his very first speedo, and while he did experience some strange feelings as he looked at himself in the mirror, in the end he just grinned and bought it.

As it turned out, he arrived only ten minutes before he heard his mother enter her own room. He had no idea what she had done, nor if she had found a way out of buying a hyper-sexy bikini. And so when he opened the door to her room, he had no idea what to expect.

And he was shocked beyond belief. The first thing he noticed as he saw his mother standing right in front of him, were the bright tan lines. Especially those on her breasts. His mom couldn't know just how much Lew loved tan lines, nor the effect hers would have on him. Lew couldn't believe just how much of her breasts he could see. Even if the tan lines made the amount of extra visible flesh obvious, he was still unable to believe. "Christ! I'm almost seeing her entire breasts!" he thought. "And those delicious tan lines..."

Lew then saw the bright red high heels and swallowed. Like most guys his age, high heels looked like relics of a ancient past where women had huge hair and wore too much make-up. But today, for the first time, looking at how it had transformed his mother's legs, something clicked. He was stunned! "How could such small things change how she looks, how she stands and, by Christ, how she radiates femininity!" he wondered. He knew he would have to look at those heels later.

For the moment though, his eyes darted back up to her big breasts as they threatened to overflow from the tiny bikini. When he was much younger, Lew had sneaked into her room when she wasn't there and had rummaged her lingerie drawer. He'd had no idea what the numbers and letters on the little white tags had meant, but he'd been impressed by the size of those cups. He still remembered taking one of them and putting the underwire against his forehead, stunned that it fit! And now, as he saw most of those breasts in the flesh, with her nipples poking tents in the thin fabric, he was overwhelmed.

Lew didn't even realize that he was staring at her breasts. His mother eventually snapped him out of his shock by saying "Lew! Close that mouth or else flies will come in!" Startled, Lew looked up into his mother's eyes and saw her smile, but he still couldn't talk. "Well, should I take this as a compliment? My son ogling my breasts like a beast in rut?"

"What?" He stammered. "No! I'm not... I mean, yes, but, NO!" Lew walked backwards until he was in his own room again.

But his mom followed him up to the door. "Isn't this what you wanted?" she asked, indicating her body with her hands. "Didn't you want me like this?"

Lew was flabbergasted. Was he hearing her correctly? Was she actually asking him if he wanted her? If he wanted her body?

Before he could make sense of what he was hearing, she narrowed her eyes and tilted her head. "Lew, it's only a bikini. Drop the act will you?" Clearly she was confused by his reaction.

"Mom!" he finally said, breathless. "I'm sorry... I'm... oh fuck!"

And with that, he closed the door in front of her and sat down on his bed, shaking. "What the fuck is wrong with me!" he wondered. "Ogling my mother like this! And now...Fuck!" he looked down at his speedos and could clearly see his cock twitching. "My mother! My very own mother! What the fuck is wrong with me?" he asked himself again.

He was well aware that his mother was beautiful, and that many of his friends thought she was hot. But although he had known all that he had never really felt it. Felt her beauty or sexiness. Until now. Until face to face with her bikini and those devilish tan lines! Gods! He couldn't help thinking about her breasts and those glowing white outlines. As if her tan lines highlighted the fact that this was flesh he wasn't supposed to see. Or lust after! "Oh for Christ's—"

But his thought was interrupted by his mother walking in the room with those devilish red high heels. And wearing that ridiculously sexy bikini. She came straight up to him and he couldn't look up. "Lew. Look at me. What's wrong baby?" But he couldn't. Doing so would mean that he would see her breasts, and he was afraid that he would stare again! His mother then kneeled in front of him and pulled his chin up with her fingers. "Lew. What's going on! Look at me!"

"I can't mom! Especially not while wearing this!" he cried, pointing to his speedos.

His mom stood up and walked back a few steps. "What? Are you serious? Are you... looking at me like... like a woman?"

Half angry, Lew looked up at her and said "Yes I am. I can't... I'm sorry... I... Shit. Can you please leave me alone?"

Lew couldn't imagine what was going on in his mother's head right now. He wasn't even looking at her anymore. He grabbed a pillow and placed it on his lap, his face burning hot with shame. In the silence, his mother said "Well, I think you were right about all men drooling with lust!"

"Mom!" Lew cried before letting himself fall on the bed.

"Lew... Look at me." his mom said softly. Surprised by the tone of her voice, Lew sat back up and looked at her. "Remember what we said about rules earlier this morning? You have no idea how strange it is for me to wear this in public. And now you too... It's strange, I'll give you that. And I don't know how I'd handle it at home. But here, it's just... I don't know... naughty? And fun?"

Lew was stunned by her choice of words. Naughty and fun that her son was lusting after her? His mouth opened against he stared at her, he heard her say "Remove that pillow, baby." His mind already shocked beyond its limit, Lew simply slid the pillow aside revealing his obvious erection. Did he just see his mother biting her lower lip as she looked at his erection? No... That was impossible.

"Well, Lew, if we're going to go out dressed like this, you're going to have to deal with that," she said, indicating his erection with a glance. "Why don't we just stay here and order some food... Maybe you'll get used to it? Maybe it's just the shock?"

"Maybe..." he replied weakly, too disoriented to make sense of what was happening.

"Ok then... So, what do you think of the bikini?" she asked laughing. "Or the tan lines?"

As he looked at her, almost literally drooling, he watched her turn around carefully and sexily on those heels. She was essentially showing him her naked ass. Full, round, lovely and decidedly sexy. Sexual even, and undoubtedly arousing! And those unbelievable tan lines! Damn it! Her entire ass was a pair of huge tan lines! It was just too much! The combination of a much more feminine ass than his girlfriend and those striking tan lines... Too much!

When she completed her turn, he looked at her pussy for a few moments and felt his heart thump hard in his chest. She was obviously shaven and her mound was extremely well defined under the thin fabric. The strings of her bikini were more horizontal than vertical, which meant that they hugged her hips more then her waist. But that low angle also meant that they created a pair of spots where the string didn't touch her skin: there were two hollows between her rounded upper thighs and prominent mound and it was mindbogglingly sexy! His eyes darted between her pussy's mound and those little hollows.

In fact, those hollows reminded him of similar spots where the strings that held her bikini top lifted away from her skin between her shoulders and her breasts. And as much as the tan lines around her bikini top were striking, those around the bikini bottom stood out even more. So many killer tan lines! The white skin seemed to grow upwards out of the bikini and spread out on either side in wide swaths of milky white perfection.

"Mom!" he finally said, tearing his eyes away from all these forbidden places. He tried playing it cool by smiling. "You can't go out like this!"

"Why not?"

"You're too... You're too damned sexy, that's why!"

"Wasn't that the point?" she asked.

"Yes, but... But... Damn it."

"Look Lew, why don't you try to forget that I'm your mom for the week?"

"Forget that you're my..." he replied.

"Why not? Just imagine that we're two... friends coming her to have fun. Why don't you call me Jessica until we get back home?"

Before he could reply, she turned around, flashed him her curvy white ass and went to her room, walking like a model on the catwalk, her heels enhancing her legs. From there, she said "Once you're able to, join me for breakfast." A few minutes later, his cock pretty much soft, he walked in the room and saw her bent down over the counter, reading the menu. Her ass looked amazing, as if pushed out by the way her heels forced her, essentially, to stand on her toes.

Lew had never been interested in full figured girls before, but he was beginning to realize just what he had been missing. Taking a deep breath, his heart beating very fast, he said "Damn, that's a nice ass Jessica!"

The seductive smile she gave as she turned her head around made him tremble. "Thank you baby..." she replied with a soft voice. "Oh, and do you think the tan lines look bad?"

"Bad?" Lew said, appalled. "Jessica... I have a fetish for tan lines. An obsession. Does that convey what I think about them clearly enough?"

His mother stared at him for a long moment, a half smile on her lips. Lew had no idea what had happened on the way back from that sex shop, couldn't understand what was going on in her mind. But she was clearly in a fey mood and for now he was going to run with it. Being able to say what he had just said was positively thrilling. That strange mood of hers was probably going to fade out as they got out of their room and as she would meet some men. In the meantime, though, he would enjoy it!

Two days later though, Lew thought about how wrong he had been about things fading out. He was alone in his bed, just like his mom in the other room, and he couldn't fall asleep. His cock was hard as a rock and he couldn't help imagining his mom on all fours above him, sucking his cock. "I'm so fucked! I'm a perverted fuck-up guy. I'm sick!" Yet he knew that if he touched his cock he would probably cum in two seconds! He hadn't had found the time to masturbate, given that he was with his mom 24/7. And boy was his libido whipped up! Then again, masturbating to his mom? Bad idea!

Thinking about those last two days made his head spin. It was one thing to roleplay at not being her son as well as to compliment her body, but things had spiralled out of control pretty quickly. First of all, she had worn nothing but that bikini and those heels. And those tan lines, damn it! On the first day, probably on some sort of crazy impulse, Lew had heard his mom tell a group of new friends that they were a couple. Shocked into silence, Lew had stood motionless as his mom had hugged him and kissed his cheek. As his mind slowly recovered from that he realized that if the plan was to get his mom a date, this was a really bad starting point.

And then things went from bad to worse. Four of their new friends, two couples, invited them to a more private spa where they spent a few hours talking with them. Lew heard his mom invent some crazy stories about how they met and how their life as a couple was going. Eventually Lew had to play along and invent things of his own. When he wrapped his arm around his mom's shoulders to pull her closer against him, Jessica grinned.

And then it happened. Their first kiss. The friends brought out a bottle of wine and after a small toast, the two other couples kissed before drinking. His mom turned towards him with a smile and not a single trace of hesitation before kissing her son on the lips. A brief kiss, for sure, but still a kiss. About an hour later, in the spur of the moment, Lew turned to his mom and kissed her again. By that point she had drunk quite a few glasses of wine and had laughed... before kissing him again, much longer this time.

It had been insane, and all during that first day! That first night, they had talked about that decision to roleplay at being a couple, but now that it was done and that many people knew, they couldn't back down. When confronted about the fact that it would prevent her from meeting guys, Lew's mom shrugged and said that she was having a great time.

The second day had been more of the same. His mother got into the habit of playfully slapping his speedo'd ass, and he happily returned the favor. It was utterly bizarre, who the fuck slapped his mother's nearly naked ass for fun, yet deeply intoxicating at the same time. Here he was with a girlfriend back home, slapping the ass of the sexiest woman on the beach, by far. The fact that this woman was his mother was beginning to fade away.

The only good thing was that he was beginning to control his erection more. Maybe it was because the tan lines had begun fading, but he could now stare at his mother's body without getting hard. Even slapping her sweet ass didn't entail an automatic erection by now. And they had kissed again. Many times. One time, after dinner just before coming back to their rooms, their kiss lengthened and their tongues touched a few times very briefly. They had both drunk way more than usual, and neither of them had any trace of remorse in the long stare they shared afterwards.

So now, in his room, Lew's mind was a whirlwind of confused thoughts and emotions. He couldn't keep this roleplay up... Or rather yes, he knew that he could. He was having a great time! But he shouldn't. It was very weird, and he was afraid of what would happen back home. Would everything go back to being normal? Could it, after that long french kiss? He didn't know, and that scared him. But how to end this? And then he had an idea.

On the following morning (after he weathered her "Good morning beautiful!") he suggested to his mother that they could go to another beach, and, perhaps, not play at being a couple? She laughed and titled her head as she was wont to do. He saw her hesitating a few moments before saying yes. And so they rented one of the small cars they had around here and drove around, enjoying the sun, the oceanside view until they found a beach that looked interesting. Lew had no idea what hell this beach was going to unleash.