Better to be Underdressed Ch. 01

Story Info
A young man is guided by an experienced young woman.
3.4k words
4.49
28.9k
26

Part 1 of the 2 part series

Updated 06/10/2023
Created 12/20/2020
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
the_heat
the_heat
35 Followers

The spring afternoon along the Champs-Elysees in Paris buzzed with tourists and the soft clank of espresso spoons mixing sugar into glasses. My first two weeks in Paris had been a whirlwind of new experiences, and there I was with the two most beautiful girls I had ever met. We sat alongside the enormous boulevard and sipped coffee, talking about the fashion program that we had recently begun. Monica and Amanda were roommates and had decided that today was the day I change from my drab, ill-fitting, outdated computer programming wardrobe, to something befitting somebody in a distinguished fashion design program.

Monica was a former model: tall, thin, flawless caramel colored skin from her mixed Egyptian-British heritage. Her loose white skirt barely covered her essentials, sitting incredibly low on her hips and exposing more than half of her thigh. Her breasts sat high and firm on her chest, not small, but perfectly portioned for her body. Amanda stood several inches shorter than Monica, but turned heads just as easily. I had noticed her from the first day of the program, her large breasts, easy smile, and beautiful golden har attracting my attention immediately. She kept her hair up in a bun and, combined with the soft lines of her face and a flowing summer dress that appeared almost translucent, seemed like an idealized version of a midwest farmer's daughter.

***

Twelve months earlier, I had been on the verge of graduation from a very good computer programming program at a decent university in the middle of the US. I feared settling into a life of working on IT implementation for local banks, and longed to try something else ... anything else. My mom had laughed and suggested that I speak to her sister, who had created, a few years earlier, a fashion design program in Paris. I had rolled my eyes at her, but called Aunt Becky the next day.

"Gary, I think I actually have the perfect role for you. We're trying to make the school a little more advanced technologically. We have been talking about designing a system that tracks trends and inventory ... let me discuss it with the board." A few days later, Aunt Becky sent an email outlining the idea she and the board had come up with. In short, the board was hesitant to have a complete fashion novice with no work experience designing their system. In exchange for maintaining a basic IT system for the next 18 months, they would let me attend the fashion program for free, and consider hiring me for the larger project after graduation.

I was intimidated by the idea of being around the "beautiful people" of the fashion industry and so, after accepting their offer, began going to the university gym. I approached it like a programming exercise, learning the specific lifts I felt would generate the quickest results, and over the course of six months changed from a 6'4" rail-thin, hunched over nerd. It wasn't a complete makeover, but I stood straighter, had a little more width across my shoulders, and felt better about myself.

***

Getting up from the cafe, the two girls playfully hooked their arms through mine and led me into a dimly lit store. Denim in every wash and color was precisely placed on gleaming metal surfaces and stylized mannequins. Electronic music pumped through the speakers just loud enough to drown out the quiet conversations of the other customers.

"Wow," I mumbled, "this is where you shop for jeans? I think my mom usually just goes to Target."

"This is the top store in the city," Amanda said, squeezing my arm. "If you're going to be part of this program, you can't wear these baggy old things." Amanda flicked at the ripped belt loop on the back of my jeans. Like most computer guys, I had never thought of my clothes as much more than cover. Baggy jeans, a few superhero t-shirts, and my gym clothes rounded out my simple wardrobe.

"Gary, you're going to look sexy after we're done with you." Monica had released my arm, and was looking me up and down. Her left hand on her hip, she casually stroked a strand of her flowing brown hair which rested between the tops of her caramel colored-breasts. "It feels like you have a decent body under all this, and I'll be damned if Amanda and I can't find it."

"Gary, what size do you wear?" Amanda asked through her big smile.

"I think I usually get a 32 inch waist," I replied, making inconsistent eye contact with the two beautiful girls. I couldn't believe these two women had taken me under their wing. I had never really talked to girls before, and certainly had never spoken to any like these two.

I found myself watching the two of them roam the store like leopards on the hunt. My initial physical attraction to Amanda had blossomed into a full-blown crush as I'd gotten to know her. Amanda played at being a worldly fashion expert, but she had rarely left her small town before starting this program, and her excitement at the small nuances of French culture was endearing. Unfortunately, Bret was waiting for her back in the US. From all accounts, he was a bit of a jerk, but he was Amanda's first boyfriend, and they had been dating since middle school.

If I was slightly in love with Amanda, I was infatuated with Monica, who had burrowed into the dark recesses of my mind and would not let go. She had a quick tight smile that she would flash at me during class once in a while. The smile and a brief arch of her eyebrow had me convinced that she was having naughty thoughts, and I wanted desperately to be a part of them.

Before long, they had enlisted a clerk to help them carry a pile of jeans to the changing rooms. The door to the back opened into a circular room with a round couch in the center, and half a dozen changing alcoves feeding into the center room.

Over the course of the next hour, I felt like I had tried on every pair of pants in all of Paris. Looking at the final pair of jeans in the pile, I started laughing. "Very funny, girls. I don't think so." I looked at the tag and saw that the jeans were primarily made of some type of elastic material. They looked child-sized. I flipped the jeans over the back of the door, and bent over to pull on my own loose-fitting jeans.

"Don't you dare put those ratty jeans back on, Gary." Monica's hand closed over the tight jeans over the door to the alcove, and wagged her finger at me. "You're trying these on."

I grimaced at the pants, but took them off the door. I held the pants in front of me, and rolled my eyes. "Hey," Monica whispered from the other side of the door, "you should try those without underwear on ... panty lines are definitely out this year." I heard the two girls giggling on the couch outside, and swallowed hard. I shrugged, and slipped my thumbs into the waistband of my boxer shorts, wanting to please the girls. I stepped out of my underwear and instinctively adjusted my cock. It had always been bigger than everybody else's, hanging about 5.5 inches limp, circumcised, thick, with a slightly darker head. While guys in the locker room had joked about its size, no girl had ever seen it. I was embarrassingly inexperienced for a 22 year old, and desperately wanted that to change.

Pulling the jeans on required quite a bit of jumping and wiggling, and the blood began to flow into my hanging member. "Shit, no." I mumbled as I tried to figure out how to fit myself into the tight jeans. I wasn't erect, but I had gained both length and width with the extra blood-flow. Looking at myself in the mirror, I felt ridiculous. I tried tucking my cock down the leg of my pants, but the tight fabric made it painful. Ultimately, sideways towards my hip was the most bearable, but I knew the bulge, not only of my thick shaft, but also the heavy testicles, was crystal clear. "I don't know about this ..." I whimpered over the door.

"Oh, come on, you cry-baby," Amanda called back. "We've got the whole waiting room ready for your grand unveiling." Nervous at how they might react, I hesitated. In a corner of my mind, Monica's quick smile and raised eyebrow flashed, and I suddenly found a hint of courage.

Taking another swallow, I opened the changing room door a crack, and peeked out. Monica was standing between the door and the couch where Amanda sat with several older women whom I had never seen before. Monica was explaining to the women the advantage of elastic woven into the fabric, quoting from memory some of the lessons that we had learned over the past week. "Ah, here's our model now. How do they look, Gary?"

"Umm, they're a little tight."

"Well, come out and let us see." She looked me straight in the eye and winked. In a movie, the different reactions the women all had would have made me laugh. At the sight of my clearly outlined cock, one of the older women sat down hard on the sofa, with her friend quickly pulling her gaze to attend to her shocked companion. The third woman's mouth hung open, then she looked up at me and smiled. Amanda looked at the other women confused, as though she didn't know what she was supposed to be seeing. Monica dove right back into her speech about elastic fabrics, and walked up to me, turning my back to the crowd.

"As I was saying, the fabric does a really nice job accentuating what you have to show." She pressed against my side, and with her right hand indicated stitching choices of the jeans as well as designer specific patterns on the back pockets. I relaxed a moment, processing the various reactions and let a sigh of relief escape, glad my penis wasn't the main focal point anymore. As she went on with her fashion discussion, Monica's left hand, hidden from the small audience, ran along the top of my waistband. I tensed as her index finger slowly traced down the fly until it touched the base of my cock, which pointed away from her.

"The root of the problem with jeans," she said, tracing the long outline of my cock, "is that some people are much thicker than others. You can solve for changing waist sizes and inseams, but it's nearly impossible to make a jean that fits great for all sizes through the thigh, for example."

My cock was painfully erect now, and practically turning the corner at my hip. The palm of Monica's small hand pressed firmly on the base as she used her thumb and index finger to massage my thick shaft. My eyes closed, and my head slumped back, my initial fear of being in front of a group had been smothered by the amazing feeling of her hidden ministrations through the jeans. Monica was wrapping up her explanation of jeans woven with elastic thread, palming my heavy balls.

"Well, I guess we should thank Gary for putting up with these ridiculous pants, and let him get changed." Monica released my testicles and stepped away, applauding and laughing a bit with everybody else. When I hesitated, looking over my shoulder at Monica, she slapped my ass and ushered me into the changing alcove.

With a bubbly laugh, Amanda ran up and lightly smacked my ass too, before turning to the older women. "Well, if you ladies thought those jeans were maybe a bit too snug, I saw a pair out there which I think would work great on the three of you. Monica doesn't get all the lecturing fun. Let me show you what I think ..." her voice trailed off as the door to the changing area closed, and I leaned agains the wall, cock still throbbing, squeezed tightly to my body, my back to the alcove's closed door. I quickly unzipped the pants, and let my heavy shaft spring free, swaying back and forth in front of me.

Overwhelmed by the feeling of release, I didn't hear the door open and click closed behind me. "Oh, Gary. I had a feeling we might be able to find something special under all those baggy clothes, but I had no idea." I nearly jumped out of my skin and quickly made to cover my erection.

"God, Monica. Don't you knock? What are you thinking?"

"I thought our little game out there made it pretty clear what I was thinking, no? Don't hide it, I want to see." She stepped forward, and put her hand on mine, gently guiding my hand away, taking with it the shirt I had partially covered myself with. My cock twitched upwards from the open fly, the dark veins straining in stark contrast to the pale skin. She reached out and traced a vein with her slender finger. "My god, that's amazing. I've never had a circumcised one, you know? I like the look a lot."

"What are you doing, Monica? What about Amanda?"

"Don't worry about Amanda. I know how you feel about her, but she's even more clueless than you are." She wrapped her hand around my cock. When her index finger and thumb didn't touch on the other side, she looked up at me and gave me a tight quick smile with a briefly arched eyebrow. She grabbed my cock in both hands, like a baseball bat, and smiled at the length still poking out. She gently rubbed the length of the shaft, rotating both hands in opposite directions. Squatting, she licked the ridge of my head, and gave a kiss to the tip, causing my cock head to flare.

"She had no idea what everybody was so impressed by today. It never even occurred to her." As she spoke, Monica released me and stood, unbuttoning her blouse. The light brown skin of her breasts had a faint sheen of perspiration. Her firm orbs were slightly larger than I had expected, and the dark nipples were hard in the cool air conditioning.

"You've never been with a woman, Gary." It was a statement. I shook my head, not trusting my voice. "It's clear. Listen. I am going to use this cock ... a lot ... for the rest of the program. I am going to teach you a lot of good tricks, hopefully give you a little self-confidence, and then I am going to help you try to get the girl of your dreams. How does that sound?"

"How d-do you know about Amanda?" I asked, trying to look her in the eyes, but my gaze consistently falling back to her breasts, sitting proudly on her chest.

"Gary, everybody knows ... everybody except Amanda. She likes you, though. There's that little problem with Bret, but I wouldn't be too worried. Now, listen. You're going to hurt your neck bobbing your head up and down. Look at my tits, touch them a little, but we need to get out of here quickly."

She grabbed my hands, and pulled them up to her orange-sized breasts, placing my palms in support, and bringing my thumb and forefinger to pinch her nipples. As I pressed, she moaned slightly. "Sit down on the changing bench. I'm going to blow you so we can get out of here. Your first fuck shouldn't be in a changing room."

I did as I was told and Monica helped me remove the jeans. She turned away from me, and lifted the back of her skirt, revealing her perfectly shaped ass and no underwear. The perky curve at the top of her long legs was incredible, and as she leaned forward, I could see her completely hairless pussy. The lips were closed tightly like somebody trying to hold their breath.

"Touch it," she whispered, and I raised my hand to her butt, gently rubbing her pussy with my thumb. I could feel that she was wetter than she looked, and as my thumb pressed against her slit, she sunk her hips, engulfing my thumb in her tight cunt. I could feel the muscles of her pussy massaging my thumb, and groaned with the thought of how that would feel on my cock.

A knock came at the door. "Gary, are you still in there?" Amanda's voice called out, and Monica spun around and dropped to her knees, smiling in awe at my long cock. She traced her tongue from the base to my head, which she popped into her mouth. Her lips sealed around the ridge of my head and her tongue danced around the tip. "Gary?" Amanda called again, and tried to knob, locked by Monica from the inside. Monica looked up at me and arched her eyebrows.

"I - yes ... I'm still ...," I mumbled, unable to string words together as Monica released my head, and leaned back, a glistening strand of pre-cum and saliva dangling between my cock slit and her tongue.

"Do you know where Monica is? I haven't seen her in a few minutes." Monica looked me in the eyes and shook her head, rubbing my cock against her hard nipples. My stream of pre-cum was constant now, clinging to the perky nipples and smearing across her tits. Her free hand moved rapidly between her legs, two fingers dipping into her wet pussy as she traced the edge of her nipples with the head of my prick.

"She - no. I thought she ... oh ... thought she was with you." Monica brought both hands around my cock, and began bobbing on the rest. More of my long shaft disappeared between her lips with each bob, until she placed her hands on my thighs and was taking half of my dick with each pass, gagging slightly when she dipped too far. "I just need a f-few ... few more minutes. I'll be there."

"Oh, ok. Maybe she snuck outside for a smoke. See you out front."

As the outer door closed, Monica sat back, took a deep breath, and slipped the entire length of my cock in her mouth. I groaned audibly, overcome by the sensation of her throat rubbing against my cock head. Her nose buried in my pubic hair, she squeezed my balls and choked slightly. "Oh, shit. I'm gonna cum, Monica."

She pulled back from deep throating me, kept my head in her mouth and licked the underside, coaxing the cum out. The first few blasts were the most intense ejaculations of my life, and quickly filled her mouth. Under the constant barrage, the cum dripped from her mouth around my cock, onto her heaving tits. As the intensity subsided, she popped my cock head from her mouth and smiled, swallowing my seed. She continued to stroke my cock gently, pointing it at her chest, a few small spurts splattering across her chest. She rubbed my head in the trails and lifted it to her mouth, licking the sticky cum off. I looked down at her, amazed. My cock continued to throb, but nothing came out, and it slowly deflated in her hand. "Monica ... that was -"

"My pleasure," she finished. "You have an amazing cock, and delicious cum. I didn't think I could get it all in, but it was so hot that you were talking to Amanda with your cock in my mouth that I had to try." She grabbed my boxer shorts from the floor and wiped off the rest of my seed from her chest. "I don't want you to wear underwear anymore ... I find it only gets in the way. The clerk has the two good pairs of jeans at the front, I think. So, get yourself presentable, and meet us out front."

Amazingly, Monica was already completely put back together. Her shirt buttoned, makeup reapplied, she reached down and stroked my limp member. "You have a nice body, Gary, and a fantastic cock." With that she gave her tight quick smile and a brief arch of her eyebrow, and ducked out of the changing room. I sat there, naked and exhausted, and realized that her naughty thoughts were an incredible thing to be a part of.

To be continued ...

the_heat
the_heat
35 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
7 Comments
maddictmaddictover 3 years ago

Dude, do us proud. Buy the jegings,(from a tv commercial) Monica likes them and what Monica likes Monica gets. Now get busy dude and do what ever she wants. Then use your rod to set the hook

'Oui'

ravishmentravishmentover 3 years ago
Well, that was a fun beginning~

Cannot wait to see where this goes. The pussibilities are endless. Please keep em cumming

the_heatthe_heatover 3 years agoAuthor

Thanks for the love. Enjoyed writing my first ... hopefully the first of many.

AnonymousAnonymousover 3 years ago
Wow!

Please write the second part soon! That was amazing!

Crusader235Crusader235over 3 years ago
Wow

Really good start. Hope you don't make us wait for more!

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Bosom Buddies Ch. 01 A nerd befriends the 5 hottest girls in school.in First Time
My Girlfriend's Neglected Mother Hot Mom, hot daughter, is anyone complaining?in Erotic Couplings
Senior Year Memories - Addison A hung nerd helps a busty cheerleader get revenge.in Erotic Couplings
Fooling with His Best Friend's Mom A twenty-year-old and his best friend's mom on April Fool's.in Mature
'Milf Next Door' Confronts Teen Mrs Harper confronts her peeping teenage neighbour.in Mature
More Stories