Voluptuous

Story Info
Andy upsizes.
2.6k words
4.37
22.4k
12
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
ValoryG
ValoryG
287 Followers

All names and characters in this story are fictional and have no connection with any actual person living or dead. The phone number is fictional.

*

Andy (or Andrea, whichever he happened to be at the moment) had preferred wearing 40B bras. Oh sure, he had others in his collection, ranging from 36B to 38B -- that he adapted with strap extenders. But for the few times he'd bought a bra, it was always a 40B. It made just the right (to him anyway) sexy projection under dresses, blouses and sweaters.

And, his breast forms filled out the 40B bras perfectly.

Andy's collection, at last count, contained no less than 16 bras. More than anything else, wearing breasts contributed to his feeling of being sexy, feminine and womanly. The right bra made him feel quite whole, and being able to look down upon a two-mound landscape was infinitely heavenly.

But his loyalty to 40B was about to be challenged. One day he was out bicycling in the country when he saw on the side of the road (nearly down in a ditch) a medium-sized, black-fabric suitcase. Ordinarily, he would've passed it by, but this one was in perfect shape. As he lay his bike on the gravel shoulder, he guessed that someone had thrown it away for some malfunction, like a stuck carry handle.

He might've been embarrassed if cars passing by saw him opening it, but he hadn't seen a vehicle for a half hour.

As he sought the zipper, he remembered how in the past he'd found discarded women's clothing and lingerie in the strangest places, and upon stealthily taking them home, found that some were actually usable. And exciting, considering that women had worn them, and that they usually carried the faint whiff of perfume.

The suitcase zippers yielded easily (apparently the luggage hadn't been rained on). and he pulled open the front flap. He became rather excited when he saw the feminine items within -- a virtual cornucopia of provocative attire and items. Just as he was about to dig down in, his conscience intervened.

What if? What if the suitcase had fallen from a car? He should find a way to return it to its owner. There were no ID tags on the outside, so he checked the two front pockets. There was nothing, except a business card for a fitness salon in a city an hour away. So, this was, he figured, probably a young or middle-aged woman who took care of herself.

Free now to indulge himself, Andy looked for items of opportunity, items that excited him. There were slinky panties and thongs, a makeup kit, two dresses, two pants, a hair drier, some tampons, sunglasses, a toiletry kit, sandals and flipflops, a pair of heels, two pair of pantyhose, and two summer-season tops. A one-piece swim suit, nightgown and a paperback novel. And, not to forget! Three bras. One strapless, one fancy Victoria's Secret type, and one plain, slightly padded T-shirt bra.

Andy looked around; there were still no cars on the horizon. He checked the size labels on the bras, which had much larger cups than those in his collection. Much larger. In fact, the strapless was a 38F, and the two other bras were 38G. Gigantic!

He was getting greedy, feeling like he'd been let loose in the women's section of a department store after hours, given free rein to grab whatever he wanted. He managed to cram everything in his bicycle saddlebag and handlebar bag, except for the hair drier and book.

Riding along, leaving the suitcase behind -- and more out of sight than before -- he had the feeling his saddlebag was glowing hot. So many possibilities within! What would fit him -- what would he keep? What would he give up because of bad sizing or lousy style -- and donate to Goodwill?

Upon reaching his apartment, Andy thoroughly washed and dried everything. Then it was try-on time, and from the moment he pulled on some of the panties, his erection was getting in the way. Most were wearable. He couldn't help but get them a bit wet with his excitement. The thongs felt nice but only one, with tiny black ribbons, contained his bulge.

The dresses were a little tight in the shoulders, but still wearable. The pants were too big at the hips and too short. The sandal and heels, too small (and not for lack of trying with the heels). True to his nature, Andy saved the best for last: the bras.

He felt almost perverse when he tried on the fancy black bra. In the past, Andy had felt that crossdressers who displayed overwhelmingly big breasts looked a little ridiculous. What was it about their personalities that they wanted such out-there busts?

Andy muttered to himself -- "elephant bra!" Nonetheless, he stuffed the oversize cups with panties from his collection, threw on a light sweater and looked at himself in the mirror. Actually, he liked what he saw. The breasts didn't seem ridiculous after all. And he liked the feel of the broad back-band. Nice and substantial. He felt the contours of the cups with his hands. Nice!

Then he pulled on one of the dresses, and was similarly satisfied. But he especially liked looking down upon his chest and seeing two large breasts.

Over time, he began to overwhelmingly prefer wearing G cups. The bras themselves didn't look as sexy as his 40Bs, but he liked the results they produced through clothing. He found himself abandoning his earlier collection, and ordered four new G cup bras online.

Andy belonged to a bicycle club and sometimes rode on club rides. He also received almost daily messages from club members through a common email list server. Perhaps three days after he found the provocative cache of woman's things, the following message was posted:

"Those of you riding the highways and byways of country roads out east of town, keep an eye out for a lost suitcase that fell out of the back of a pickup several days ago. It's black, fairly new. If found, call 211-684-3002."

Other members asked further questions, and it was eventually revealed that the Howard family, a farm family, had lost the cargo. Andy had met that family at several social functions in the past. There were a husband and wife, and two little kids.

So he was wearing the clothing and intimate apparel of this woman, whose name he remembered as Joanna! He remembered her as 30ish, with a slightly pudgy figure, and oh yes, big breasts. A blonde who, he remembered, liked to wear extravagant earrings. She was outgoing and ever so solicitous about her children.

In a funny way, when Andy now wore Joanna's clothing, it was almost like having sex with her, of having her. The perfume she used lingered in her things, and when he could see evidence of her having worn the clothing -- such as a loose thread or two, or a very small fabric tear -- that just made the feeling even more powerful.

He had a strong urge to see her in person, and wondered where he might find her. He remembered she was active in the FFA, the Future Farmers of America, as an adult volunteer. So several weeks later when the county fair took place in the next city over, he dropped by, wearing her panties underneath his male clothing.

And he wasn't disappointed. There she was, helping with the cattle judging, wearing a jaunty cowboy hat, fairly tight levis and pointy western boots. From a distance, he looked intently at her bountiful breasts under a semi-tight white shirt. As she moved, her boobs bounced just a little, giving him an involuntary erection. He could almost make out the shape of her white bra underneath. Having brought his DSLR camera with, he zoomed in on her and grabbed some pictures.

After a time, he left to find some fast county fair food, which turned out to be Chinese, along with some beer. At this point he was eating off a paper plate on a picnic table, watching a local rock band on stage.

Dozens and dozens of fair goers were walking by, and quite young women in skimpy outfits were attracting his attention. Their bra straps were often in full view, leaving little to the imagination, and their favorite attire seemed to be distressed jeans with threadbare holes. Just when Andy had returned to down another bite of egg fu yung, some folks sat down next to him.

It was the Howards! Without their children. Mr. Howard spoke, and Andy was deathly afraid he knew something damaging. But instead, "Andy, we saw you taking pictures in the cattle shed, and you've got a really good camera, it looked like."

"Yeah, it's good. This is such a great place to take people pictures." (Especially of buxom women.)

Joanna was letting her husband do all the talking. She looked a little tired. Andy had only been able to sneak one glance at her breasts.

"We do the FFA newsletter and was hoping you had some photos of the cattle judging we could use."

Andy breathed a sigh of relief, and was glad that he'd photographed more there than just Joanna. He promised to email them some of his best shots.

Then, against all his best instincts, he popped up with, "I'm part of the bike club, and I saw a note that you lost a suitcase. Ever find it?"

"No, never. We looked along our route. Maybe someone just grabbed it and kept it. Don't know."

"Did it have an ID tag?"

"Probably not."

"Well, I'm sorry you lost it."

Joanna spoke up, laughing, "Well, on the plus side it meant that I got to buy some new duds." (And Andy thought: Yes, and I got to wear yours.)

As the Howards left, Andy got a faint whiff of Joanna's perfume. It was exactly the same fragrance as in her lost clothing, and in the very panties he was wearing.

Back home, Andy selected and printed out several of the photos of Joanna. Then he dressed in her bra, panties and dress; looked at himself in the mirror; fondled his penis; and then lay down, and while looking the shape of her breasts in the photo, beat off. It didn't take long; it was quite a royal climax. In feeling the jizz on his hands, he felt as though Joanna had been branded deeply onto him, like perhaps she had branded a steer.

He knew he had the ability to absorb another person. When he went to a movie featuring an attractive, strong male or female lead, he'd leave the theater feeling that he was that person. It made him feel powerful, ready to take on the world.

Now he felt like he was channeling Joanna; that she occupied him. In fact, he went so far as to obtain copies of the exact clothing she wore at the fair, and even bought a wig that duplicated her hair style. He also found some gaudy earrings that were as large as hers, and had his ears pierced to wear them.

He had never done makeup before, but learned enough to duplicate the eye makeup and lipstick she had used at the fair.

Then, of course, he took photos of himself.

In the ensuing months he found two more opportunities to be at an event Joanna attended, and slyly snuck some more photos of her. He hoped she didn't suspect anything. He also found a couple photos of her online.

Perhaps, he thought, he was becoming too preoccupied with her. He wasn't dating anyone. Girls his age seemed too cliquish and hard to please and unpredictable. But Joanna -- now there was a woman who exuded a mature sexiness and was more down to earth. She offered a warm bowl of friendliness.

As the months wore on, Andy had accumulated four different Joanna looks that he could adorn himself with. He knew his fascination was over the top, and that should people find out, he would be the object of derision and jokes. Still, imagining that he was Joanna and Andy together in one body, propelled his masturbation to very satisfying heights.

At one event where he'd stealthily managed to grab even more shots of the voluptuous Joanna, where she was without her hubby, but had her kids, she asked if Andy could drive her home, since her ride had to leave early. With the kids safely belted in the back seat of his Prius, he was excited to be seated next to his goddess. She was wearing a long cotton peasant dress, with matching white sleeveless top that nicely displayed her breasts. It had a band of lace around the low neckline. He caught a glimpse of her bra as she got in.

They made small talk as he drove the ten miles to her farm. He knew his voice was betraying his nervousness, and there was the fact that he was wearing a pair of her panties. Once more he became aware of her scent. But she was so personable and unthreatening -- almost like a mother. A sexy mother. He would have loved to reach over and cup her ever-so-perfect tits.

Eventually, she aimed their talk toward him, and his life. He knew this was deliberate, and yet felt flattered that she had some interest in him, a boring male. She wanted to know where he'd gone to college, where he'd grown up, and how he liked his job.

And, "Andy, are you seeing anyone now?"

"No, not at the moment."

"Well, that's too bad, because you're a very attractive young man -- an eligible bachelor."

They both laughed. For just a small moment Andy veered in the road.

"Well, thank you. I did have a girlfriend from work a couple years ago, but she moved out of state and took up with someone else."

"That's really too bad. Now you're going to think I'm too forward, or pushy, or whatever, but I'd like to set you up with someone."

"And who would this be?" He laughed a little nervous laugh.

"This would be my younger sister, who's coming to visit in a week. Susan. She just doesn't want to sit around on the farm and feed the hogs all day. She'd love to go out a little and see the town, and I think you'd be perfect to do that, Andy."

Susan turned out to be a younger version of Joanna, with the same figure that Andy had come to know and love. And she was just as lively, friendly and warm. She had recently left the Air Force after a six-year hitch and was going to return to college using her military benefits. She was more disciplined than her older sister; maybe from being in the service.

Andy and Susan hit it off and became an item, and there came the night when a kiss turned into a long embrace that that turned into a romp in bed. There, Andy had the odd sensation of being part Joanna, making love to her sister. Girl to girl.

Afterwards, he tried to divine how Susan saw him, because he knew he'd been quite unaggressive and somewhat soft and yielding.

A couple days later, Susan said, "Andy, I want you to know that you were so wonderful in bed. I really, really had a wonderful, sexy time. I've been with guys who all they thought about was their own satisfaction, you know. Jump, bump, fuck and come! Now, you really know how to please a girl."

The next evening when they were resting after yet another coming together, Andy lay his head between Susan's big breasts and felt like he could remain there forever. Warm, secure and oh so sexual.

Funny the way life happens. Andy opens a mysterious black suitcase, and a genie comes out to bring him to the woman of his dreams.


ValoryG
ValoryG
287 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymousover 2 years ago
First Timer

First time out in public made up and dressed as a women i have become.I had to get used to having female breast I took to many female horemones and ended up with 38d breast it took a little getting used to them But the men loved them as will my firm ass I also find out men love my red nails and my bright red lip stick and lip gloss.They really love my red lips around their hard cocks.All most as i love taking their cocks in my mouth.But i really love a large hard deep in my ass filling me with loads of cum

AnonymousAnonymousalmost 3 years ago

I didn't see that ending coming! Well done!

ValoryGValoryGabout 4 years agoAuthor
Thanks

Thank you so much. I wish I had more time to write. This story wasn't xxxxxerotic, but it I hope it seemed real enough. Viva la 40G!

DianeRedfernDianeRedfernabout 4 years ago
A Lovely Beginning

You are a very provocative and imaginative author, This is one of your sweeter and more wondrous stories. Very lovely and PG-Rated. Self-contained - more to come? Either way, I enjoyed it.

xoxo,

Di

Share this Story

Similar Stories

My New Job A college kid undergoes a transformation at his new job.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
A Beautiful Me at Honeysuckle Lake A crossdresser opens up to his mom's best friend.in Transgender & Crossdressers
Neighbors Pt. 01 The Lesbian Neighbors help a femboy blossom out of his shell.in Transgender & Crossdressers
Miss Ellen 7'8" hermaphrodite Ellen inadvertently feminizes her servant.in Transgender & Crossdressers
More Stories