Rachel's Vacation - Part 1

“Thanks, I had a great time!” waved Rachel as she flashed her pretty smile that kept her suitors coming back for more every time. Her date smiled back as he drove off in his bright yellow Hummer, undoubtedly thinking of the big, beautiful woman he had just gone out with, feeling like the luckiest man alive.

Rachel turned around and started towards her apartment, climbing the front steps. The sky was starting to darken as evening crept in and, after digging through her handbag for a few seconds, Rachel produced her keys and let herself in.

The girl’s apartment was a mess—empty pizza boxes, Chinese take-out boxes, paper bags, candy wrappers, bags of chips, boxes of pastries, tubs of ice cream, and such littered the place. Also littering the place were empty boxes of chocolates and chocolate wrappers, sent to her by her various dates. At 22, Rachel was enjoying her bachelorette dating life. No commitment allowed her various suitors, all of whom fed her pretty well, to her enjoyment. When she wasn’t dating, shopping, or working at the nearby bakery, she was usually just bumming around at home, eating. But then again, she was usually eating all the time anyway.

Rachel whipped out her handheld phone-slash-organizer and checked her calendar as she settled onto her couch, digging into a near-empty box of brownies.

“Oh my gosh, only thirty minutes ‘til my next date! And it’s with Mike too! Better get changed” she said through a mouthful of brownie, heaving herself out of the couch and heading to her room.


Rachel’s typical day was usually riddled with dates from various suitors, all of whom she used to get free lunches…and dinners, and desserts, and various meals in between too! In fact today, she had just come from her second dinner date (yes, the girl could really eat!) and was about to head off to her third with Mike.

Mike was one of Rachel’s favorite suitors. He was rich, real nice, a gentleman, and quite timid, just the way the flamboyant Rachel liked her dates.



“Man that second dinner was good!” said Rachel to herself as she examined her reflection in her full-length mirror. She gave her big, well-fed belly a satisfied pat, which made the inch or two of her exposed, light brown blubber wobble as it spilled over her hip-hugging pants.

Rachel knew she was a big girl, and she was proud of it. She just oozed sexiness, and was able to work her magic on even men who didn’t normally prefer larger women. She also loved to eat and stuff her face, which she knew only improved her assets—“assets” meaning her boobs…belly…butt…thighs…

Another thing why she liked Mike though was that she knew he was the type of guy who naturally preferred larger women. Rachel recalled their first date and meeting, wherein the poor guy almost passed out from shock upon seeing the large, voluptuous woman. Rachel personally found that quite cute.

Rachel decided it was time to get dressed, and unbuttoned her form-hugging blouse, whose buttons were straining against her huge chest and big belly.

“Ahhhh…that’s better!” said the relieved Rachel, as her gigantic boobs and belly bulged out freely as she rid herself of the constraining top. “Note to self: don’t wear blouses to all-you-can-eat buffet dates” she said, putting her hands on her big belly as it bulged over the waistband of her unbuttoned pants. “Oh, and buy new bras…real soon!” she laughed, cupping her massive breasts as she watched them spilling out of her now too-small JJ-cup bra. “Man I’m getting big!”

The big girl then began to pull down her form-fitting pants with difficulty, groaning as she inched the tight denim fabric down her massive rear end.

“Good god I’ve got a big butt” she said, stating the obvious as she glanced upon her reflection in the mirror, her giant ass even wider than the frame.

She then opened her nearby dresser, ready to pick out some clothes to wear.



“Oh, it’s a date with Mike, right! Gotta dress to impress!” she giggled, selecting her wardrobe for the date.



Moments later, Rachel glanced at her reflection in the mirror once more, nodding in approval. She was wearing a very tight white tube top and apple green short shorts, which she had amazingly managed to cram her huge boobs, belly, and ass into. The top left a good amount of her big belly exposed and bulging over her shorts, as well as a nice amount of cleavage pouring out of the front. Also, being white and made of quite thin material, Rachel’s outgrown, light blue bra could be seen through the fabric as her huge boobs bulged against it. The shorts barely managed to cover her huge ass, with a bit of butt cheek bulging out, her large thighs obviously fully exposed.

Basically, Rachel’s idea of “dressing to impress” was cramming her huge self into the tightest, skimpiest clothes that could fit without ripping.

With a tropical flower in her cream colored hair, her flawlessly smooth light-brown skin, and her ornamental green earrings and bracelets, she looked like an exotic goddess. Her naturally beautiful, soft features and that oh-so-voluptuous figure definitely added to her overall “wow” factor.  

“Oh Mike’s gonna love this outfit!” she smiled, winking at her own reflection and giving her giant boobs a heave upwards as she adjusted their perkiness.






Mike sat at the table he had reserved for him and Rachel at the local American restaurant. Rachel loved the place since they served such big portions, and everything was either barbequed or fried, with lots of potatoes on the side too! He checked his watch. She wasn’t late yet, but Rachel was usually the type to come early on a date, especially one that started with eating. Mike ran a hand through his messy orange hair and took a glance again at the menu the waiter had given him for him to order ahead for both him and his date. “No, she’ll do the ordering, thanks” he replied with a smile, the waiter bowing out graciously.

“Hey Mike!” suddenly came a voice from behind him.

Mike turned in his seat to see a large, brown-skinned girl walking over towards him. He almost had a nosebleed—Rach was wearing a very tight, slightly see-through tube top, her belly and boobs bulging out of it, and a pair of very short short shorts, which showed off the girl’s huge thighs and ass. Mike noticed a few of the other customers in the room stared as well, some in admiration and lust, some staring with shock at the fat girl crammed into tight clothes, some shaking their heads in disapproval (particularly the girls who had dates with them already).

“Rach!” he smiled timidly, standing up to greet his date.

Their size difference was apparent. Mike was 5’2”, a quite short man, and was rather skinny as well. Dressed in his conservative suit, he was a stark contrast to the confident, big Rachel who was bulging out of her tight outfit. Rachel was a big girl at 6’1” and who-knows-how-much lbs. Although Mike knew Rach was proud of her size (and loved flaunting off her assets), he still never bothered to ask her weight. She did love complements though regarding her size and weight, which Mike found a bit different, but very sexy and confident as well.

“Wow Rach, is it just me, or are you looking even bigger now?” said Mike, his eyes bulging a bit as he looked up at his huge date who towered over him.

“I’ve been eating real well, that’s all” giggled Rachel, grabbing her belly fat with her two hands proudly. “Although I might have put on a few extra lbs lately” she admitted, remembering her outgrown bras and unbuttoned shorts. “Ready to make me even heavier, Mike?” she winked.

“Oh, of course!” laughed Mike nervously, pulling out a chair for Rachel at their table.

“Great, ‘cause I’m starving!” said Rachel, despite having had two dinners already before this. Mike watched as she lowered her gigantic ass onto the chair, which seemed to plead for mercy as the girl’s huge rear end, which was actually wider than the seat, bulged over it, spilling over the sides. Mike winced a bit as the chair creaked under her weight.



Mike, despite being quite young at only 24, had become the head of his father’s highly successful company which he inherited after his father retired early not too long ago. Needless to say, Mike had money, so it was okay that right now, Rachel was ordering dish after dish, and wolfing down food like there was no tomorrow.

The two were a regular at the place, and although at first the waiters and chefs were in awe at the big girl’s appetite, they had grown used to Rachel’s massive binging whenever she brought a date (especially Mike) over. Indeed, whenever Rachel had a reservation at the restaurant that day, the chefs and waiters all secretly called it “code red”, as they all had to work quite hard to satisfy the hungry girl.



“Did you enjoy that, Rach?” asked Mike timidly, several (dozen) orders later.

Rachel sat there, licking her fingers happily, surrounded by stacks of empty plates. Her huge belly, now even bigger and fuller from all that food, bulged onto the table heavily, quite exposed as her top hardly managed to cover it at all anymore.

“BBBUUUURRRPPPPPPPP!!!” went the full girl, letting out a huge belch. A few of the other customers glared, but Rach didn’t care. “You know I always have a good time with you, Mike!” she said happily. “Look how much fun I had” she smiled, rubbing her big, bulging belly.

“Looks like you did have a lot of fun” laughed Mike nervously as he gazed at the massive tummy that bulged before him, big and brown and fully exposed.




Later, Rach was happily eating her fifth ice cream since they had left the restaurant, as she and Mike walked down the street. Suddenly, the spotted a cute little photo booth.

“Ooooh Mike, let’s have our picture taken! I’ll just finish this up” she said, stuffing the rest of the cone into her mouth piggishly, her face a mess of ice cream. “Let’s go!” she said, still crunching on the cone, licking her sticky fingers.

Mike climbed into the self-service booth first, after inserting a few bills into the pay slot. As he sat down inside, he realized the booth was quite cramped. How in the world was Rachel going to—

“I’m coming in!” chimed Rachel’s voice, as her head stuck into the booth through the curtains. Mike’s eyes bulged as following her head came the rest of Rachel’s body, which was actually even wider than the booth’s entrance. The booth really was quite small.

Rachel slowly crammed in her giant chest, belly, hips, and ass through, wiggling her hips as she squeezed through the narrow entrance. Finally, she fit in (well sort of) and took her seat next to Mike.

“C’mon Mike, act like we’re actually on a date!” she exclaimed, grabbing the guy’s skinny arms and wrapping them around her thick waist, although they didn’t reach around fully. Rachel turned herself to face Mike as well and wrapped her meaty arms around him too, in a tight embrace. The booth was so cramped, and Rach was so big, that her giant boobs were pressing against Mike’s face, and her big belly was bulging against him too.

The camera flashed a couple of times, and when the pics developed, Rach was the first one to pull them out and take a look. All of the pics showed the pair of them facing each other and “hugging”, although only Rach’s smile was clearly seen—Mike’s face was smothered against Rachel’s gigantic breasts, and most of him was being smooshed by her big belly.

“Wow, I look pretty big in these pics…I guess I shouldn’t have had those last five orders of pork chop, huh Mike?” she joked. “Mike?” she went, looking down to see his face still smothered against her huge chest. “Oops!”



Later that night, Rachel found herself in Mike’s luxurious penthouse suite, located at the topmost floor of one of the more high-end apartment buildings in the city. Of all her suitors, Rachel only ever spent the night with Mike, not just because he had a wonderfully luxurious pad and an unlimited supply of food, but because she genuinely liked spending time with the slight-framed man.

“Thanks for letting me spend the night again, Mike—I owe ya one!” winked Rachel, as she walked into the spacious living room having come from the kitchen. She was working on a tub of rocky road ice cream as she came in, and was still dressed in her outfit from dinner.

“Oh no problem, Rach. I had Remy prepare the guest bedroom for you to stay in, so everything should be alright” smiled Mike politely from his sitting position on the couch. Remy was Mike’s personal butler, and although he slightly disapproved of the loud, boisterous, gluttonous Rachel, he still served his master and his guests with all the refinement required of those in his line of work.

Mike looked down on his lap, silently contemplating something. In his hands he held an envelope. Was it the right time?

Mustering all his courage, he cleared his throat.

“Rachel, I have a surprise for you” he said with a smile. “Have a seat and I’ll show you what it is”.

Rachel turned to Mike, half way through her tub of ice cream. She often received gifts from Mike, and she always loved them—but he had never looked this excited to present her with something before. This made her excited as well.

“Really?? What is it, tell me!” she went excitedly, quickly falling onto the couch beside him, her huge ass crashing down on the poor seat, the entire piece of furniture buckling under the impact as the cushions sank under her weight.

“Well…” began Mike, opening the envelope he held in his hands. “…I remember how you mentioned you really wanted to go on a real vacation this summer…”

“Andddd…?” beamed Rachel, sticking a spoonful of ice cream into her mouth.

“Well, I made a couple of calls, and got you this” he said, handing Rachel a brochure. Outside the brochure was the text “Discover Paradise!” in bold, and inside were pictures of sparkling clear water, white sanded-beaches, palm trees, luxurious-looking hotel suites, and best of all, lots of pictures of delicious looking food!

There was also a credit-card thing tucked inside the brochure, which had Rachel’s name on it, as well as Mike’s signature.

“I got you an all-expense paid trip to Paradise Island, which I heard is a pretty damn good vacation spot. I hope you like it” smiled Mike unsurely.


Rachel didn’t know what to say. It was her dream summer—a vacation spent on a tropical island, with no worries at all, relaxing and pampering herself, all expenses paid!


“Oh my god, you are the BEST Mike!” she said, wrapping her thick brown arms around the frail man and pulling him in a tight embrace. Her huge chest bulged over his face as she squeezed him tightly.

“Mfff-mmmffff!” came his muffled reply from beneath the girl’s massive bosom.

“Won’t you be joining me, Mike?” asked Rachel, as the two of them sat on the couch, Rachel now working on a box of doughnuts.

“I’m afraid not, Rach. I’ve got work to do, although I will drop by now and then for a date or two!” he smiled.

“That would be great, sugar—least I can do to repay you for all this” she winked. “Oh, but I have to get packed!” she went, remembering she had no clothes with her. It turns out Mike had really taken fast action, and had booked her flight for tomorrow morning, bright and early. At such short notice, Rachel didn’t have anything with her at the moment.

“Don’t worry Rach, I can send Remy later tonight to pick up some of your clothes at your place if that’s okay. Oh, and I got you a small something for your tropical island vacation too!” said Mike, suddenly remembering something and heading off excitedly. “Be right back!”

He soon returned carrying two shopping bags with him, which he handed to Rachel.

Tearing them open, Rachel found that one contained a cute apple-green bikini, and the other a pair of floral-printed short shorts and a bright yellow spag top. She also noticed that the articles of clothing looked a little bit small, and quite skimpy.

“Oh Mike, you really do love me squeezing into such skimpy clothes!” she grinned, feeling quite sexy. “Thanks for these—I’ll make sure to put ‘em to good use!”

“Glad you like ‘em, Rach! Oh yeah, I forgot to mention—don’t lose that card I gave you. That’s what you’ll use to pay for everything you avail of on the island, but don’t worry, it’ll all be taken care of by me” said Mike in a humble manner.

“Aww you’re the best, Mikey” she winked, her beautiful face lighting up. Mike loved her brown skin, her cream-colored hair, those soft but bright features, and the little accessories she wore like her earrings and bracelets and the flower in her hair. She looked like an island goddess, and he loved the tropical, exotic air Rachel had about her—it made her really stand out in the crowd. That, and of course her bulging, voluptuous curves.

“These pictures of food look great! How good is the food on the island?” asked Rachel, going over the images in the brochure again, her mouth watering. To satisfy herself, she reached for another doughnut.

“Pretty good, I think. Gingerbread Island was rated highest in terms of culinary diversity and quality by this elite tourism organization I know of” said Mike.

“Sweet!” said Rachel, excited. “Then I hope you don’t mind if those clothes you just bought me don’t fit as well by the end of my vacation” she winked.

“Not at all, Rach” smiled Mike.