Better to be Underdressed Ch. 02

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tagFirst TimeBetter to be Underdressed Ch. 02

After the most amazing afternoon of my life on Friday, I saw little of Monica or Amanda for the rest of the weekend. The girls had taken me to a few more shops, and I'd ended the day with a couple pairs of jeans, some nicely cut shirts, a cool sportcoat, and a new pair of shoes. In total, 6 new pieces of clothing cost more than my entire wardrobe, but I had to admit that they looked good. Amanda had even showed me that some of my t-shirts would look nice and purposefully "vintage" (instead of just old) if I combined them with the nicer stuff I had just gotten.
Our first fashion designs for school were due on Monday, and I was struggling. "Mate, don't push it," my roommate Karim suggested. Karim had quickly become my best friend in Paris. Not having many close friends in the US, he was practically my best friend anywhere. His father was a Nigerian diplomat who had moved the family to Russia, Italy, and Thailand throughout his youth, and Karim was quick to make friends everywhere he went. He was nearly a foot shorter than I was, standing no taller than 5'5", but was wider through the shoulders and much more muscular. He liked to joke that finding clothes was like trying to outfit a fire hydrant. He was also the blackest man I had ever met, and his shaved head shined like a mirror.
"This is the first outfit you've ever designed. How good was your first programming assignment?"
"Complete shit," I said, chewing on my pencil and staring at the drawing of a simple suit I was attempting.
"Of course it was! And how good were you at fucking the first time?"
I cringed a little. Karim would have been accepting if I'd told him I was a virgin, but it was embarrassing … being 22 years old, and only two days removed from my first blowjob, I was not ready to have that chat. "You're right. I was complete shit."
"And your first fashion design will be complete shit also!" He flashed his big smile that seemed to split his head in two. I rolled my eyes at him, and turned as I heard the door to the studio opening. Emmi and Karim had been an inseparable couple for the past two weeks. Emmi was German, and as pale as Karim was dark. The left side of her head was shaved, and her pink and black hair swept over from the right side. Her sleeves were rolled up, showing the tattoos which started at each wrist and disappeared into her shapeless canvas shirt, reemerging to dance across the exposed skin of her neck and upper chest. Her skin-tight black pants with pink skulls disappeared into her knee-high platform boots. Despite the two extra inches her boots gave her, she still barely broke 5 feet tall.
"My darling Gary," she pronounced my name and 'darling' with a long 'ah' sound, which the class had begun to imitate, "your suit looks a bit like shit. That shape is for a woman, not for a man. You will like Caraceni. The suits that he made in 1930s are like this." She was brutal with her criticisms, but always followed the criticism with precise insight to get me past the corner. Her drawings had been flawless from the first day; the colors impeccable, the structure excellent, and the texture of her sketched fabrics seemed almost tactile. She kissed me on the cheek. "Do not worry, my darling Gary. Everybody is shit the first time."
She left my workspace and stood behind Karim, rubbing his shoulders and looking at his drawings. "You are drawing a beautiful suit, Karim, but there's something off … maybe you are stressed. Maybe we should go fuck upstairs while Gary finishes. Then you will be relaxed, I will be relaxed, and you can come finish."
"Yes, my little edelweiss, let's go. Gary, do you need something from the room? Is it cool?" I nodded and smiled. The two of them were pretty considerate, but they could lock themselves away for hours.
"I have my computer down here. I'll look up Caraceni and see if I can finish this in the next couple of hours."
Emmi kissed me on the cheek again on the way out, and Karim clapped me on the shoulder. "Even Caraceni was shit the first time, mate."
A few hours later, Karim and Emmi stopped back in the studio to see if I wanted dinner. I declined and took the opportunity to take over our bedroom. Sitting alone in the studio, struggling to finish, I had been consistently distracted by the thought of Friday afternoon. Was Monica really interested in doing more? Did Amanda actually like me back? What would have happened if she had caught us?
The last question had quickly driven my blood and attention to my dick, which swelled quickly as my brain toyed with possible scenarios. With more than a little effort at concentrating, I finished my work, and Karim and Emmi's exit prompted a quick retreat to the room.
Back in the room, I dropped my things on my desk and sprawled across the lower bunk of our two beds, looking at my clock as 10 PM hit. The room still smelled faintly of sex. They had left the window open, but the tangled sheets on the bunk above my bed held the smell, and the blood rushed back into my dick. I didn't fight the swelling this time, unzipping my fly, and releasing my rapidly thickening cock. Per Monica's instructions, I had taken to not wearing underwear, and was pleased at the ease of access.
I began to picture Amanda walking in on me and Monica. She would be shocked at first, maybe, then aroused. Monica would reach out to her, placing Amanda's hand around my throbbing cock. Amanda would lean forward, her tongue reaching out –
A knock on the door cut through my reverie, and I scrambled to cover myself. "Shit. Just a second, I'm coming," I called out, as I stuffed my quickly deflating member into my pants. As I opened the door, there stood Monica smiling up at me.
"You're not coming yet, but you will be," she said as she slid past me. I closed and locked the door, staring at Monica as she looked around the room. "My darling Gary," she says, imitating Emmi's pronunciation, "have Emmi and Karim been at it again, or have you found somebody other than my sexy, big-breasted roommate? It smells an awful lot like sex in here." Despite a simple outfit and no makeup, Monica looked incredible, standing in the center of the room, nearly 6 feet tall.
Her breasts were much smaller than Amanda's but still substantial, and demanded attention in profile. Her braless nipples pressed through her light cotton night-shirt. The swell of her breasts lifted the hem of her shirt, creating a slight gap over her abdomen where the shirt didn't quite hit. Below her shirt, 4-5 inches of exposed light brown skin filled the gap between her shirt and faded cotton shorts. Her shorts clung tightly to her ass, and cut off right above the break between her ass cheek and the back of her long lean legs.
Monica always dressed like this for bed, and I had seen her and Amanda in pajamas many times hanging out with them late at night on the floor below. Seeing her like this, in my room, with the remnants of a fantasy floating in the back of my head, however, left me dumbstruck. "Gary, have you found another little minx willing to take that big member you're hiding?"
"No, sorry … no, it was Karim and Emmi. They were in here for like two hours."
She smiled and sat down on my desk, crossing her legs, laughing. "Those two are like machines. Three, four, five times in a row with no break." How did she know that? I wondered. "Must be hard to be his roommate. Come over here, Gary. We need to have a chat."
She motioned to the desk chair in front of her. I sat down and she swiveled on the desk, placing her heel on the chair between my legs, and resting the sole of her foot, topped with painted white nails, on the bulge in my pants.
"I want you to know that I had an incredible time on Friday, and I am very much looking forward to doing that again," she started, moving her foot back and forth along my expanding bulge. I nodded, and swallowed hard. "Amanda likes you a lot, and she's probably beginning to realize how much you like her. Brett's a concern, but not much of one, I imagine."
My heart was pounding in my chest. Arousal at Monica's actions, and hope from her words battled in my head. I could only croak, "ok. So what should I do?"
She smiled at me, pressing harder against my cock with her foot. "I want to keep playing with you. I want to play with this as long as you'll let me. There's a chance Amanda catches us, of course. If she does, she might not care, but she might. I think I could keep my friendship with her, but I don't know how it would work for you. There is … uncertainty."
Monica pinched my zipper with her toes and pulled it down. In my rush to cover myself, I had forgotten to button my jeans. She rubbed the widening base of my cock with her slender toes. She slipped her big toe under my cock, and flexed her foot, popping my shaft free of me pants. It flopped back and forth, not fully erect, but pulsing as blood began to flow. Her white-tipped big toe traced the side of my shaft, and my head flared as she rubbed the ridge. "Good boy, not wearing underwear."
She pressed the ball of her foot against the base of my cock, massaging gently. She reached up to the hem of her shirt and lifted slightly, exposing the undersides of her breasts, then paused. "What do you think, my darling Gary?"
"Are you asking me to choose between sex with you now or maybe Amanda? " I whispered. "I can't … I don't know."
"No, it's not fair to tempt you like this. Anytime you want to quit … tomorrow, next week, next month … I promise nothing will change, we can still be friends. There will be no more of this, of course," she said, lifting her shirt a little higher, the darker skin of her areolae peeking out from under the hem.
"Or this." She traced her big toe along the shaft of my aching cock, up to the ridge of my swollen head and back to the base. Three times she repeated the motion and I stared stupidly as her white-tipped dark toe traced its path along my long cock, veins thick with pumping blood.
"Now, yes … I'll think more tomorrow," I mumbled and ran my hand up her silken legs. I ran my thumbs along the slight ridges of muscle definition at her calves, and traced her thighs up to her shorts.
She lifted her shirt off, and placed her hands on the desk. A faint flush was apparent above her breasts, her nipples crinkled with arousal. "Pull them off," she whispered and pressed down with her hands, lifting her ass from the desk, and uncrossing her legs. I gently took the waistband of her shorts and pulled down.
I couldn't take my eyes from her hairless pussy. Her light brown lips opened slightly, moisture clearly visible along the soft pink of her slit. I pulled her shorts down her legs, but her foot remained pressed against my cock, and her shorts ended up dangling from my shaft like a flag. She smiled and lifted her foot from my lap, placing her feet on the arms of my chair.
"It's beautiful," I whispered, absentmindedly rubbing Monica's legs and staring at her exposed sex. She breathed deep and her lips spread a bit more. She slid forward on my desk until her ass rested just on the edge. I took a deep breath through my nose, and the musky scent of sex was tinted with something sweet. I leaned forward and kissed the tender skin of her inner thigh.
"Good boy. Nice and slow." My kisses continued to inch closer until I reached the crease where her leg and pelvis met. I switched to her other leg, starting at mid-thigh and covering every inch of soft skin. I hesitated, my mouth hovering over her pussy, both of us breathing heavily. She groaned at the feeling of my breath on her lips, and put her hand in my hair. "Please," she whimpered.
Using the tip of my tongue, I gently traced the outside of her lips. She flexed her butt, trying to force more pressure, but I kept only a light touch with the tip of my tongue. Looking up between her breasts, rising and falling with her heavy breathing, I pressed her clit with my tongue and she groaned. She looked down at me, eyes pleading for more.
We kept our eyes locked, and I flattened my tongue, pressing hard for a long lick up her entire slit. Her eyes flared with pleasure and her grip on my hair tightened, pulling me harder against her. "Please … Gary. Keep doing that."
I obeyed, repeatedly pressing hard with long strokes, and then flicking her clit after each one. She responded by thrusting her hips at me, adjusting my consistent pressure to where she needed it, fucking herself on my tongue. I ran my hands up her sides, and stroked the edges of her breasts, rewarded by yet more groans. As her thrusting against my tongue became quicker, I roughly grabbed her breasts and pinched her nipples hard.
"Oh god!" She cried out and grabbed my hair with both hands. She pulled my mouth tight against her cunt and squeezed her legs around my head. I couldn't breathe, but didn't care. Her whole body tensed and she ground her pussy against my face. With little room to move, I fully extended my tongue and buried it in her gyrating pussy, flicking it against the warm soft walls as her moans intensified.
When she finally relaxed and released my head, I sat back in the chair. I smiled and looked up from her swollen, wet sex to her face, flushed and panting.
"Are you sure you've never done that before?" she asked, trying to catch her breath. I shrugged and grinned wider.
"That was amazing. You taste so good," I said and reached out to run my thumb along her swollen lips. She shuddered again and pulled back a little before relaxing and letting me gently rub her.
"Amanda will never leave your bed, if you're really that good, " Monica laughed, and I wished she hadn't said that name. Though Amanda had a boyfriend, I couldn't help but think this was cheating. On the other hand, my aching cock demanded the attention of the half-Egyptian model naked in front of me. Sensing my hesitation at the mention of Amanda, Monica reached down and removed her discarded shorts from my penis. She stroked it lightly and looked me in the eyes.
"Are you ok? I was serious when I said we could quit anytime."
"Yeah, I'm good," I replied, sighing at her light touch. "She has a boyfriend. I can't be a celibate backup plan, right?"
She leaned forward and grabbed my cock tighter, bringing her lips to my ear. "Good. I've been wet all day thinking about putting this cock in me." She wrapped her hand around my balls and pulled, forcing me to stand and leading me to the bed.
Standing next to the bed, I removed my shirt, and Monica ran her finger in a circle around my nipple. I looked down at her as she leaned in and took my nipple in between her teeth, biting gently and squeezing my shaft. As I groaned, she stepped back and slipped her hands to the top of my jeans, pushing them to the floor.
We stood there naked and looked at each other, her chest flushed, and a shimmer of moisture trickling down her thigh. My cock throbbed in anticipation between us. "You look beautiful," I whispered nervously.
"So do you," she smiled, stepping up on her toes to kiss me. "Sit on the bed. I need to have control of this big cock the first time."
I sat down on the bed, and leaned against the wall, stroking my shaft for a little relief. I pressed it up against my stomach, and the head rubbed against my belly button. Monica had one foot on the bed, and smiled down at me, her pussy still wet. "It's such a great cock, Gary. I like watching you play with it."
I grinned, and grabbed it at the base, squeezing tight to make the head and veins expand. She licked her lips and kept her gaze locked as I stroked the length of my shaft, a drop of precum appearing. She straddled my hips, her clit pressed against the base of my cock. She rolled her hips, causing my prick to make long slow arcs across my belly.
"I need to lube you up a little, big boy. I don't want you tearing my tight little pussy apart … too much." She rubbed her wet cunt along my shaft, spreading her juice around. Her firm breasts danced in front of my face, and I grabbed one, taking her nipple in my mouth and sucking on it. As she continued to rub her slit along the underside of my shaft, I could feel liquid dripping down on my balls. She pulled back, her nipple popping out of my mouth.
"Are you ready?" she asked with a quick wink.
"Please. I need it."
She squatted over my cock, shimmering with her juices, and took the base in her delicate hand. I watched as she lowered herself onto the head, her pussy lips stretching to accommodate my girth. In a moment, the head disappeared inside and she sighed loudly. Her hand moved to my shoulders to support her, and she began a series of short bobs to lower herself on my cock.
"Oh, Gary. Oh, fuck, this feels incredible."
Even her perfect breasts in my face couldn't distract me from the sight of her light brown lips stretching wide around my pale shaft. I could feel the smooth wall of her wet cunt gripping the ridge of my cockhead as she pulled up. As she lowered herself further, I closed my eyes, overwhelmed at the heat of her sex. She wiggled her hips back and forth as she sunk further, until suddenly I felt her dripping lips press against my pelvis.
"Oh, christ," she whispered, lowering her knees to the bed from her squatting position. She lowered her head to my shoulder and breathed deeply. I held her close, reveling in her warm body pressed against mine. As her breathing calmed, she looked up at me and smiled. "I didn't think it would all fit, Gary." I felt the walls of her pussy contract around me.
"I've never felt anything like this," I groaned. I placed my hands on her hips and pressed down a little, forcing the tight walls of her pussy to press even tighter around my cock.
We sat in silence for a few moments, I could feel her pulse through the stretched walls of her sex. With every breath she took, the tight grip around my shaft changed slightly. My fingers traced the curve of her back, and hers traced from my chest to my chin, lifting my head up to look in her large brown eyes. "Oh fuck," she moaned, "I can feel the veins of your cock. This is unbelievable. You're so fucking big."
Leaning in, her parted lips met mine as her hips began to twist in tight half circles. She groaned and pressed her clit hard against my skin. Our kiss became frantic as she fucked herself on my cock. Pulling back from the kiss, Monica rocked back into a squatting position and steadied herself with her hands on my shoulders. My hands drifted to her tight ass, feeling her muscles tense as she lifted up. Her glistening lips pulled as my cock emerged from her. Inch after inch she pulled back, until I could just barely see the ridge of my cock head peeking out. Without hesitation, she pressed back down hard, the length of my shaft disappearing immediately. She cried out, and pulled back again, the grip of her cunt practically paralyzing me. Another hard downward thrust, and another shriek broke me from the moment.
As she began to push back up again, I grabbed her hips and held her down. "Monica, you have to be quiet … these dorm walls are paper thin. We're not trying to let everybody in Paris know."
"Gary, I've never had anything like this cock in me, and it's driving me wild … I was thinking your first time should be slow and easy, but I'm feeling greedy. I need you to fuck me. Hard." My cock pulsed as he stared me in the eyes and delivered her request. I struggled desperately for a solution as I absentmindedly massaged her ass cheeks. "I have an idea," she said, and slowly slipped off my cock, her lips gaping as she pulled me to my feet.
She climbed onto the bed on her hands and knees, positioning my pillows between her hands. She looked back at me and winked. I stared dumbstruck at her long lithe back leading into her tight round ass. Her cheeks spread by her kneeling position revealed her puckered asshole over her dripping lips. "Now, fuck me. Hard. As hard as you can" she whispered, brushing her wavy brown hair from her face. "I can muffle most of the sound with your pillows."

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