My New Roommate Pt. 03

**I'm a very slow writer so thanks if you waited for this. My First story. This is a multi part slow burn romance so the beginning is mostly character development. I would love reviews, feel free to give any criticism.**

The first few weeks living with Simon were going fantastic! We spent a lot of our time together those first few days, and I was starting to think that the survey we took may have been more accurate then I gave it credit for.

Just like Simon's family warned me, our joint closet soon became more his than ours. I filled my side with all the hoodies, jackets, and button ups that I had. I even hung a few extra shirts to save some space, yet, my collection couldn't even fill one side of the closet. Meanwhile Simon's clothes had filled two full sides of the closet and was making its way over to mine as well.

I got some time to look over Simon's clothing in passing and to say it was feminine would be an understatement. I wondered how much of the clothes he inherited from his older sisters, as the majority of it was clearly women's clothing. When I looked I could see he had a little bit of everything, there were pull over sweaters, denim jackets, fleece jackets, blouses, rompers, vests, half hoodies, zip ups. Shirts in multiple styles, from long sleeves, ruffled tops, u-necks, crop tops, baby dolls, skater tops, tie-ups, and more. On top of all that, he managed to squeeze fourteen pairs of shoes into the bottom of the closet, lining the side wall.

Then there was his dresser, the top was a mess of jewelry, perfumes, hair ties, makeup, and a few school things. His drawers were just as packed as the closet with the top three drawers nearly overflowing with what appeared to be his bottoms. He had a wide spread of jeans, joggers, yoga pants, shorts, pajamas, sweat pants, spandex, leggings and much more from what I could see in passing.

However, the thing that stuck out the most to me was his bottom drawer....

Unlike the rest of his drawers, this one never got left open. I assumed that was because it's his underwear drawer and as the days passed I couldn't help but wonder if his underwear were also a mix of men and women's. Most of his other clothes were women's, so I guess it would be natural to also have the bottoms...

There was more than once when I could see the outline of Simon's underwear due to the tightness of his clothing and swore there was a panty outline that looked like any ex I've ever had. From time to time I would get a colorful flash of his elastic underwear line, or see something at the top of his hamper while the lid popped open and couldn't help but wonder. However Simon was rather reserved about his nudity and would usually change clothes in the bathroom, or occasionally he would close the door to the closet and change inside. I hadn't seen Simon in his underwear or even without some sort of shirt on but ultimately, I liked Simon and wanted to be respectful of his space, so I did my best to wipe it from my mind.

It wouldn't take long for things to escalate however! Over the course of a week, our relationship would change....

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The first situation happened a monday, I came home and was relaxing on the couch, enjoying the dorm to myself. I knew it would be another two hours or so before Simon got done with his classes and I planned to get my homework done before he was back. Eventually I made my way towards our bedroom to grab a few things I'd need, but I stopped immediately upon entering.

"What the..." my shock couldn't be kept within, my voice shot out almost involuntarily.

Simon's bottom drawer had gotten left open!

As I looked I saw a variety of colors bursting from the drawer and a massive amount of panties, bras, and socks in a variety of styles all roughly folded and tightly packed in...

I was frozen for a moment, partially aroused and partially nervous as I looked upon Simon's underwear. I did my best to look away and push any dirty thoughts from my mind as I gathered some things to get my work done. Yet no matter how much I tried my eyes continued to glance at his dresser.

Eventually, with all my things assembled I was ready to leave but i couldnt...

I slowly walked to the dresser, taking in his robust panty collection. My eyes darted but my hands remained frozen as I stood before the drawer. I didn't need to move anything, as his other drawers were mostly closed and the bottom drawer was nearly completely open. I wanted to remain undetected so I simply let my eyes roam taking it all in, curious as I was about the panties, the bras seemed to be the most odd part seeing as Simon doesn't have boobs! It hardly mattered at this point, and the more I looked the more I imagined his tiny, feminine, frame in a matching lace set of bra and panties!

As my eyes continued to roam, I saw something different among the fabric tucked deep into the back corner. At first I couldn't tell what I was looking at as it was far in the corner and nearly completely buried by panties. There was something small and metallic, circular, with a ring? Then next to it was something similar but pink, plastic, more like a cage, a very small one, also with a ring attached. I looked at them for a moment trying to understand what they were, yet found myself lost...

I continued looking at the pile of objects and saw next to them a silver bulbous object with a blue gem on the end, this one confused me less as I'd certainly seen these before. With the three of those was a skinny, purple, bullet looking object, with a white button on the bottom. I was beginning to feel that I knew exactly what I was looking at. I was looking at Simon's sex toys.....

I shot up from the drawer, feeling shame as I began realizing that I violated Simon's privacy.

"Shit!" Again the situation caused me to speak out into the open air.

Backing away, I dwelled on whether I should shut the drawer or not. If Simon came home and saw he left it wide open he would know I saw the contents inside. The drawer was closed on every other occasion though, and what if Simon thought I had opened it? In the end I decided to close the drawer, and hope there would be no suspicion raised.

As I left the room my mind continued to race.

"What were those things... i think the small purple one was a vibrator but what about the others... they were clearly sex toys but for what..." my mind ran a million miles a minute.

"I shouldn't have invaded Simon's space, I knew it was wrong, and all because of my own horny curiosity...." I continued to reel

I checked the time and realized I had about an hour before Simon gets home. I knew I should at least attempt to get some homework done, so I spread my things out onto our small dining room table and started to work.

The time flew by and before I knew it I heard our door starting to open. Simon came walking in giving me my first chance to look at him for the day. His normally flowy brown hair was put up into a high pony tail today, giving a full view of his bright green eyes and light makeup job. The top of his tiny frame was adorned in a flowy, white, long sleeved, crop top. It was a 3/4 fit with a small stripe of his belly left exposed. While on the bottom he wore a pair of his black leggings with white stripes running down the lengths that were pulled up to just under his belly button. The two pieces of clothing did wonders to show his hourglass figure. Finally he had a pair of black and white matching tennis shoes that he quickly kicked off exposing his ankle socks. His legs always looked incredible in leggings and now knowing he had a pair of panties underneath I couldn't help wondering what style and color they were...

"Gaaahhhh, my brain hurts." Simon's soft voice called out. He was kicking his shoes off, and flinging his back pack off before making his way over to me at the table.

"Sounds like you had another fun day of classes." I spoke trying to be as normal as possible.

"ending my day with Tompkins class.... just kill me..."

As Simon sat down next to me he placed his head on my shoulder, and continued to decompress from the day.

"It's like, how can something so important be taught by someone soooo boring?" Simon continued on as he rocked his head back and forth on my shoulder.

I adored the comfortability we had grown to share and this was one of the benefits. As Simon continued on, his sweet perfume filled my nostrils with warmth, and his soft voice lulled me into a sense of comfort. Had I been in a more comfortable chair I could have easily fallen asleep like this, but before long my trance had broken and I heard Simon's voice continuing on.

"Uuuuggghhh, I just wanna forget about it." Simon perked his head up, looking in my eyes, I got to look at his make up closer, and found it to be as flawless as ever. "Have you eaten yet?"

"Uhh, I was down in the cafe earlier, But it's been a while if you want to head down." I said.

"Plllleeaaaseee" Simon spoke in an exaggerated tone. "I'm starving, I ate like nine hours ago and I might just die!"

"I can see your withering away" I said, as I poked Simon's tiny belly with my finger.

"Heyyyahaha, " Simon let out a light protest while laughing. "You know I'm ticklish, you bully" Simon quipped at me while he also poked me in the belly.

However I wasn't ticklish like Simon and simply endured his poking with a straight face.

"No fair!" Simon yelped.

"You're just too easy to play with" I retorted as I placed my right hand onto his thigh before giving it a squeeze.

"Eeeeehhhhhhh" Simon squeeled out in a high pitched tone. His body instinctively jolted, with his butt scooting back in the chair while his head flung forwards into the crest of my neck, his arms latching onto me. "Ok, ok, ok, please!" His voice was high pitched and squeaky.

I let up, not wanting to torture poor simon, and as I did he brought his head up to meet my eyes. I couldn't help but notice how plump Simon's lips were, they were a bright pink, with a coat of lip gloss, and looking incredibly kissable.

"Soo... did you wanna go to the cafeteria then?" I spoke softly as we were both seemingly lost in each other's eyes. Simon let up on his grip while backing up slightly in his chair.

"Yeah! Let me just change into something cute real quick!" Simon spoke as a grin adorned his face.

I came to learn rather quickly that Simon loved wearing different outfits, and would often change two or three times in a day. His massive closet started to make sense as time went on and he definitely got his use of every piece.

"Aren't you already wearing something cute?" I asked

"Think so?" Simon stood up and struck a pose for me to admire.

I didn't answer, instead I smiled and my cheeks flushed lightly, clearly giving Simon his answer.

"Buuuttt, I wanna wear something lighter." Simon said while grabbing the waistband of his spandex leggings and stretching it.

As he did this I looked down a bit from his waistband towards his crotch. It wasn't the first time Simon had worn something skin tight like this and yet he never seemed to run into problems with bulges. There was a small little bump that seemed to form below where his cock would be, but nothing like what It would be if I were to wear something like that.

"Sooo, give me like 10 minutes and I'll be ready." Simon's voice chirped

"Alright, I'll give you 20 minutes." I spoke, teasing Simon.

"Heeeyyy" Simon stuck his tongue out at me, cleanly protesting my teasing. "I'm not that bad"

"Just don't get lost in Narnia, alright!" I said

"Uuggghh, you sound just like my sisters!" Simon's voice squealed.

"Well I'll just be here finishing up a bit of work while I wait."

"Okaaayy!" Simom spun around before trotting off to pick a new outfit.

I couldn't help but check Simon out while he pranced back to our room. Those leggings he wore were leaving little to the imagination and even helped to shape his thighs and ass in a delightful manner.

It was about ten minutes before Simon emerged from our room, he was holding a pile of clothing and was making his way towards the bathroom. This wasn't odd for Simon as he often changed clothes in the bathroom. However, right now he would have had the bedroom to himself and could have just changed there...

I looked at the pile and saw what appeared to be his favorite grey onesie, some calf socks, his big hair brush, small makeup bag, phone, and right on top, next to his makeup bag, a matching pair of, lacy, blue panties and bralette. I looked up to Simon, not wanting to stare and found him with a big cheesy grin across his face. Did he know what I saw earlier?

"Why are you so smiley?" I prodded Simon.

"Oooooohhhh, I'm just excited to eat!" Simon smiled as he nearly skipped across the room.

"That was already ten minutes" I shot at Simon.

"I know, I'm gonna be quick!" Simom squeezed out before slipping into the bathroom. His tone seemed even more cheerful than normal.

"Uh-huh" I said, however Simon was gone and I was left to wonder.

Did he know I saw his panty drawer earlier? If he knew that he left it open then he would know that I closed it. But if he only wears panties then why would it even matter that I saw his drawer, wouldn't that just be normal? Then to just bravely show his underwear Ike that, was he trying to make a point? I attempted to do some homework as I waited but found my mind drifting until Simon eventually emerged from the bathroom.

His hair was down now and his make-up appeared to be touched up with his cheeks looking brighter than before. He was now wearing the onesie I saw earlier, it was a gray, loosely form fitting, full body piece, something similar to pajamas that he wore often at the end of the day. The ankles and wrists had three black rings on them, with a black zipper that came down the middle to about his belly button, and there was a little pocket on the right breast. He was wearing some mid calf socks over the leggings of the onesie and was grabbing his white fleece zip up jacket, to go over top. The only thing I couldn't see were his blue panties, but knowing he had them on certainly drove me wild.

"Ooookaaay! Let's go slowpoke!" Simon chirped in an excited tone, while slipping on a pair of white shoes.

"Oooh, now im the slowpoke, even though you took twenty three minutes changing!" I said

"yup! See, I already got my shoes on, Now come on slowpoke." Simon continued on, as he reached to the coat hanger and grabbed my zip up, swim jacket.

"Is that what I'm wearing?" I said, making my way towards Simon, seeing him holding open my jacket.

"It's what you always wear!" Simon's voice was peppy as he held it open and helped me into the arms.

"I sometimes wear my other one!" I pushed back.

"You want that one?" Simon questioned as he ran his hand along the sleeves.

I inhaled for a moment, looking into Simon's cute green eyes. "Naaahhh, I like what you picked!" This elicited a large grin from Simon as I slipped on my slide sandals. "Ready!" I said moving to the door as I opened it for both of us.

"Of course!" Simon said as he skipped through the door before waiting in the hallway. I quickly locked the door before turning back to him, Upon which time he sunk himself into my side and wrapped his arms around my waist. I in turn wrapped an arm around his shoulders and allowed him to nuzzle in close to me. This was a growing normality for us, ever since our first day together, something that started light as a comfort, now became something more....

I could feel it in how we gripped one another, both of us held each other tighter, more comfortable with letting our hands explore, my own hands would often find a new home, from neck and shoulder to back and hips. There was more than once when I got asked who my girlfriend was, usually it was the guys on my swim team, but I never paid them much mind beyond getting annoyed on Simon's behalf.

After eating we walked back in a similar fashion with Simon leaning heavily into me, stating over and over how tired he was. The rest of my night was rather uneventful as we went about our business as normal. Simon didn't leave the bottom drawer open like that again, but it hardly mattered, I'd seen all the proof I needed and from then on, any time I'd see a faint outline, or catch him making adjustments, I knew exactly what was going on under the pants.....

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The next occurrence happened on a Wednesday night, I was sitting on the couch in our living room waiting for him to join me. It didn't take long before Simon was finally finishing up his bathroom ritual, and upon opening the door I could smell the vanilla scented body wash before I saw any of him. When he came to join me, I was greeted with the sight of his pale, long, silky smooth legs in my eye line.

He was wearing a red and white, form fitting pair of short shorts, or "shark shorts"... so Simon told me. They came up past the half way point of his thighs, giving full view of his cleanly shaved legs, and shaping his plump behind. Simon seemed to take pride in his legs as clothing like short shorts and leggings were a regular occurrence for him...

As my gaze wandered beyond his legs I saw His hair was wrapped in a towel and his shirt had changed into a drapey light red ruffled shirt with sleeves that barely went past his shoulders showing off all of his rather small and undefined arms. It was definitely a bed time outfit, just something lighter and breathable, yet I found it all so sexy.

There was another eye-catching addition to his person, as he now had freshly painted baby blue toenails. This wasn't new of course, Simon often adorned painted nails, and really looked natural on him. I was being rather obvious in my gawking I suppose, as he stuck a leg out almost in a modeling fashion and began to wiggle his toes around.

"Liking what you see?!" Simon's tone was playful.

"Not too shabby!" I said, matching his playful tone. "Is that what you were just doing?"

"Yeah, I wanted to do a little something extra for tomorrow. Even if I'll be wearing socks the whole time!" Simon let out a soft giggle with that, as he made his way onto the couch beside me.

Tomorrow was a field trip for his programming class to a somewhat local robotics company.

They were a billion dollar company and would often get interns from the college. Although Simon's class was freshman year, it would be a great chance to shake some hands and see what a future job could look like.

"Gotta kill that first impression!" I spoke.

"Always! Do you remember what I was wearing when we first met~"

I smiled slightly as thoughts of Simon ran through my head.

"Hmmm, I seem to remember a lot of blue!" I quipped

"Glad it was memorable, cause I'm gonna wear that top again!~"

Simon had a coy smile spreading across his face. Soon he was crashing down on the couch beside me.

"I definitely remember those shoes you wore"

"My hightops!- Yeah I love those... but, I'm gonna wear something different tomorrow, I think they'll look better with the jeans I picked!"~

"Oh yeah? Don't wanna wear something as tight as last time?"

"Seeee~~ i knew you remembered my outfit!" Simon spoke with a swoon in his voice as he teased me. My cheeks grew a shade of red.

"Tight jeans don't bother me." Simon continued. "I like them, actually! I just wanna wear a different pair, they're a lighter color and don't have tiny rips in them."

"Those other ones are a bit worn." I spoke

"Well, there a super old pair, i actually got them--"

"From my sister!!" I cut Simon off teasing him back.

"Heeyyyy, shhhhushh mister" Simon laughed as he shot his hand up to cover my mouth.

We play struggled for a moment as I moved my head around to avoid Simon's grasp. His small body bumping up against me as his hands rubbed across my face.

"OK ok OK!! I won't cut you off anymore" I spoke between laughter

"Yeahhh suuure"

Our conversation bounced for a bit until eventually we moved onto what we should do for the night.

"I don't know... i don't really wanna watch a movie right now" I drolled on

"We could play something?" Simon inquired. "We haven't played any of my gamecube games"

"True, what did you have in mind"

"Ummmm, multi-player..... I have Mario party! Maybe double dash, if you really wanna get your butt kicked!"

"Pfffhhhh, what!" My reaction was nearly involuntary.

Simon let out a soft laugh at me. "You've played double dash before?" he said.

"Oh yeah, I've played it a few times!"

"Do you think you could beat me!~" simon spoke in a mischievous tone.

Of course!" I said while sitting up slightly in my seat

"I think you might be getting in over your head!" Simon spoke with a growing smile as he teased me

"I think you're gonna be eating your words when I whoop you!"

"Youre gonna Whoop me!" Simon spoke sarcastically, teasing my choice of words.

"How about we bet then!" he spoke mischievously

"Oh thats an easy bet, your on" I chimmed

"We didn't even make any stakes though~" Simon's soft voice chirped.

"We can bet whatever, it'll be an easy collection for me"

"Alright Mr. Arrogance, how about a massage?"

My eyebrows shot up as my mind raced quickly, I was pretty surprised to hear this from Simon. It was honestly the last thing on my mind but the moment I processed it... I loved it.

"That'll be perfect, my shoulders have been feeling tense."

"Ohhh, poor baby!" Simon cooed as he teasingly rubbed my shoulder. His soft small hand felt nice on my muscles. "Its to bad you'll be rubbing my legs!~"

"Your legs!?" My tone was shocked and my face reflected it.

"Yeaahh! That's my pick!~" Simon smiled devilishly at me.

"I didn't know we were allowed to pick!"

"Well you said shoulders so I just assumed we were picking what kinda massage we wanted!~"

"In that case I wanna pick back and shoulders."

"Alright then I'm going with legs and feet!"

"Hey! Stop adding stuff!" I raised my voice in jest protest.

"Whhhhhaaaat~ We both picked two body parts!"

"But your feet! I don't wanna touch those stinky things!"

"Heyyy, you were just complimenting these stinky things!"

With that Simon moved his feet up to our coffee table and began wiggling his toes. In truth they looked rather cute, with the fresh paint of baby blue nail polish, and their hairless dainty stature. As we both looked towards his feet I took time to run my eyes along his legs. They were so enticing in the dim lighting, with no hair and little muscle definition they mirrored many of my crushes throughout the years. I yearned to touch them and the thought of getting to massage them was getting my blood flowing.

"Ok OK. But no more adding!" I spoke in a false sense of agony.

"It shouldn't matter since you're gonna whoop me, remember!?"

"That is true, you're gonna be the one doing all the massaging!" I trumpeted

"Then is it a bet!?" Simon perked up.

"You're on!" I said, smiling widely.

"Oh it's totally on! I'll get it set up, I gotta let my hair out anyway!" With that Simon shot up from the couch and began grabbing at his towel, unraveling it and freeing the flowy, brown, nest of hair.

With his hair flowing freely he bounced to the tv before beginning to work on setting things up. I couldn't help but take this time to steal lust filled glances at his ass and legs, for someone that doesn't workout out he had quite the bounce and definition to his backside. While looking I noticed his shorts had rode up a bit while sitting, becoming even shorter. This caused more of his thighs and ass to be put on display as the waist of his shorts were now up under his bellybutton with the fabric along his ass beginning to sink into the crack.

Bent in front of the tv, his shorts became so tight I could see the outline of his panties. They must have been a small piece as the outline hugged tightly, high on his cheek giving two alluring stripes along his plump ass. Oftentimes when I saw Simon from behind like this I would mistake him for a woman, now in this pose, I saw no difference....

"Ready to get your butt kicked!~" Simon turned to me, finished with the setup. As we looked towards each other I could see Simon's face was beat red.. as was mine...

"Yeah, right! Cmon, get over here!" I gestured towards the couch.

With that Simon skipped across the small distance between us and plopped himself down carelessly onto the sofa. His little body fell into me but I hardly moved, it felt nice more than anything...

"Oooh, you're a Luigi picker!" Simom teased me as we picked our characters.

"Of course, Why!?"

"No reason, it's just kinda funny since I always pick Daisy!" Simon said, locking in his pick.

"I've always picked Luigi, that's my guy! I even went as him for Halloween two years ago!"

"Really!?" Simon's voice went high with excitement. "I went as daisy three times!"

"Hahha, What!? Really!?" I asked while laughing

"Yup, 4th, 5th, and 6th grade... I was oooooobsessed with Daisy and I wouldn't let anyone tell me otherwise!"

I let out a small laugh at Simon's story. "Sounds like we found ourselves costumes for this year!"

"Oh my god! Are you for real!? That would be so much fun!~~"Simon's already feminine voice was reaching new decibels as he got excited.

"I meeeaaan, I was kinda joking but seeing how excited you are I wouldn't mind being luigi again!"

"Yeeees! I love, love, love this idea!" Simon squealed with excitement.

"Well for now we're gonna have to let the couple battle it out!" I poked

"And like most couple spats, the woman will be coming out on top" Simon smiled as he poked fun at me.

"you wish lady!"

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It didn't take long, twenty minutes at most, and Simon had handily beaten me in all 4 races. I'd like to say that it was close but in reality Simon completely destroyed me.

"Tried to warn ya!~" Simon's wide grin was glowing.

"That was a setup, you're a freaking pro!"

"That was one of my favorite games as a kid, you never stood a chance!~"Simon taunted.

"I'll remember that next time you try making a bet..." i grumbled

"Speaking of that~~" Simon began to run his hands up his exposed legs.

"Oohhh, I see how it is! Very quick to cash in!" I joked.

"Just reminding you of our little bet!" Simon jeered as he continued running his hands along his gleaming legs.

I sighed, "Right now?"

Simon's brown hair bounced as he nodded his head in response.

"Ugggh Alright alright, let's do it." I spoke in feign exasperation.

Simon gave out a Squeal of excitement before shooting up off the couch

"Hold on a second, gotta grab something!"

He spoke while walking off to the bathroom.

Before long he returned with some cocoa butter lotion and made his way to the far end of the couch before placing both feet into my lap. It felt like hardly any weight at all as I began to run my hands along his lower legs.

"If you want you can use this lotion, I'll have to put some on later anyways..." Simon's tone lacked any authority or commitment, like a kid asking for something they weren't supposed to have. "... and it'll definitely help make it easier to move your hands around... Plus it smells really good.." Simon continued his pitch.

"You don't have to keep going," I spoke as my smile grew wider. "Ill use it... since you insist!"

We both beamed with excitement as our eyes met. Simon had a deep red color on his cheeks and he was nervously biting at his bottom lip.

"Close your eyes" I spoke softly

"Hmmm, why!?"

"Cause I don't want you judging my work! Plus, massages are better when you're relaxed."

"Okaayy, If you insist!" Simon smiled broadly as he closed his eyes.

I took a moment to put on some music before applying a small amount of lotion to my hands and making my way towards his feet. My hands started at the mid way point, working up towards his toes.

"How's my paint job!" Simon inquired

"Looks really good!" I shot.

"I'm glad you approve!~" simon spoke softly. "But are they dry?"

The paint job had long since dried, now the deep pools of blue kept my attention as I worked my fingers between his tiny toes.

"Yeah, I think you're all good!"

"Good! Don't go messing them up mister! I did a great job on those!" Simon spoke with mock authority

"Don't worry! I know how much you care about your nails." I spoke

"Darn right! Beauty takes effort, but it's worth it!" Simon lectured on.

"And you have it mastered!" This drew a massive smile from Simon. "Now, shhhhh! Just enjoy your massage!"

"Okaayyy!~~"

As I looked up from his feet towards his face I saw he kept his eyes closed as I asked. His soft facial features were framed by his wavy brown hair, he was again biting at his bottom lip. I looked down at his body to see his shirt tented where his hard nipples were piercing into it. His hands were gripping the side of his shorts, changing between a strong and soft grip depending on what I did. Finally I could see his hips moving, just slightly, in a small circle. It was intoxicating to see his tiny waist wiggle from side to side.

I continued to work his feet slowly, they were already so soft from Simon's skin routine that my hands had an easy time gliding across them. I began to do long deep strokes on the bottom of his feet, before switching and doing the same to the top. It seemed to be a favorite of his as he couldn't help but let out a noise"

"Mmmhh~"

"Pretty good?" I spoke in a whisper

"Realllllly~ Mmmm~"

"Shhhh" I softly shushed Simon as he giggled, losing himself in the massage.

There was no doubt we were both loving this attention and with the position of his feet on my lap I'm sure he could feel my tented shorts from my growing erection. With his breathing growing rapid and his hips wiggling I assumed he was also fighting a growing erection, yet when I would steal a glance I saw no signs of a tent peaking up. Instead I just saw his tight short shorts laying nearly flat against his crotch and riding up his hips! What little bulge there was showed no signs of hardening.... I didn't have much time to worry about it as I felt the need to hide my own growing cock.

I started to move from Simon's feet to his ankles, but before going any further I moved Simon's legs to the side for a moment while making a quick move to adjust my now fully erect cock upwards and into my waistband, keeping my shorts from tenting. After the quick shift I moved towards the lotion on our coffee table hoping to avoid drawing any attention to my shifting. As I looked towards Simon I saw that he kept His eyes shut the entire time, His disheveled hair and pursed lips drew my attention. His features were so delicate, so feminine, so entrancing.

"Heyy, no stoppppingg!" Simon's voice was soft and swooning as he pleaded.

"Just grabbing more lotion." I must have taken too long adjusting and grabbing lotion.

"Told ya it was a good idea!" Simon quipped.

"Yeeeeeahh, it's pretty convenient... smells really nice!" I drolled

"And it feels really good!" Simon added

"Shhh, just lemme work my magic" I spoke in a low tone.

"Ooohh, it's working!" Simon voice was shaky

With my hard cock tucked away I focused back onto Simon's massage. I moved a bit to the right allowing simons calfs to now lay on my lap. With the increased access I ran my hands up his bare, smooth, glistening calfs, as I made long strokes to apply lotion all over. My hands went all the way to his knee and just glanced at the beginnings of his thighs. I took my time to apply a bit of lotion on both his legs before focusing in on his left leg first.

I massaged his calves in small circles while moving upwards from ankle to knee. Simon seemed to enjoy my technique as he would occasionally let out a soft moan and continued to gyrate his hips in a small circle. I switched to his other leg and continued my technique while I stole glances up towards him. He seemed to be in a state of bliss as his breathing became labored and his eyes pressed tightly shut.

With the lower half of his legs now massaged I went to again apply more lotion. We never discussed how far I would have to go as part of a leg massage, however I assumed since he was wearing short shorts, I would just do all the parts that are exposed. I again shifted to the right a bit on the coach and now had Simon's knees in my lap. I began making long passes up his thighs to spread lotion all over. The way his legs laid out upon me almost reminded me of a piano, every inch of him another note for me to play!

"Ahhhaa Mmhhh" simonly softly moaned into the air.

His high pitched moans told me all I needed to know about how I was doing, as my hands went about an inch from the bottom seam of his shorts. As I made long passes up the front of his thighs, his breath was growing rapidly as his chest jutted forward, his nipples rock hard, poking out aggressively against his shirt. He cooed into the air as he did his best to stop any overly loud moans from slipping out in bliss.

"Hhhh, ahhhhhh fuuuuuckkk~~" Simon let out a long moan.

"Hey now, no need for that spice!" I retorted

"Mmmmmhh, you're really gooo-Oooooohhhh good at this!" Simon managed to peep out

As I continued my massage I grew more comfortable with pressing the boundaries of where I could go. My fingers now dipped to the beginnings of his shorts as I pressed lightly against his skin. His shorts were high up on his legs at this point, and my hands got so close to his crotch, that had he been hard I would have been hitting something. Yet his soft inner thighs were like framing for his still flat honey pot.

"MmmmMmhhhmmM!~~" Simon again let out a low groan as he bathed in the attention.

The massage had gone for more than 15 minutes at this point and I was fighting an erection the entire time. The more time went on the more wiggly Simon became, his hips and belly were moving in sync as his toes and fingers curled and unfurled. As I looked towards his dimly lit face I could see his soft features in a state of craving. His mouth was switching from a gap and breathing heavily, to biting at his lips, stifling his moans. His hair was a mess at this point as his long brown hair covered most of his face and his small upturned nose poked out from the mess, giving him a particularly feminine look. Yet the entire time, he kept his eyes closed just as I asked...

"Flip over" I spoke in a whisper

"Hmmm, whhaa?"

"Cmon, lemme get the other side."

Simon began to move as he finally opened his eyes to meet mine. His cheeks were on fire and he had a glassy look in his eye. He hardly managed to open his eyes in this dream-like state, instead he made just enough effort to softly look into my eyes and seek guidance. I was undoubtedly blushing and sporting a lust filled gaze myself as I met Simon's emerald eyes.

"Okaaay~~" Simon smiled widely, giving little resistance, and again closing his eyes.

Simon was already laying on his back and it didn't take much effort with my help to get him rolled over. I got quite the show as his ass jiggle around with his short shorts driven up tightly into the split of his ass. With Simon now on his stomach I could freely look and take all of him in. With this angle I could also see the bottom of his ass cheeks as he began to spill out from the bottom of his shorts.

I started my massage again, working the underside of his calves,

"Ahhhha, mmmm~~" Simon moaned into the cushions.

"Am I doing alright?" I inquired

"Sooo much better than just alright!" Simon's voice was muffled in this new position

"Well... thank you!" My words were short as I soaked in Simon compliments. "Ya know, when I beat you, you're gonna have to do the same for me!" I spoke antagonistic to Simon.

He let out a soft giggle in response. "Might wanna choose a different game then!"

"Now that I know you're a pro I won't be choosing double dash again"

"Awwww, what if mhhhhh- ahh, i promise to go easy on you!" Simon groaned as he toyed with me

"Hey, shush you! That game was basically a setup!" I teased to simon

"Nooooo, and besides, you... were- mmmmhmm~ the one who chose that game!" Simon cooed between his words as my massage enticed him.

"Yeah but you added the massage bet...."

"Buuuutttt, you're a physical therapy major, ahhhh, mmmmhhhh, so really I'm helping you out, letting you get extra practice!" Simon spoke teasingly

"Hey! I'm not just some glorified masseuse!" I spoke in a mock authority as I gave Simon's thigh a playful slap.

"Eeehhphh!" Simon let out a high pitched squeal in a shocked reaction. "Okkkaay, ill be good, i won't tease you!"

"I'm not sure you're capable!" I jeered at simon

"I will!" He protested back

"Have you been Good so far?" I whispered.

"Hmmm? What'd ya mean!?" Simon questioned

"Are your eyes closed?" I questioned

"OOooh! Of course.... I'm a good gir... err listener!" Simon now spoke in a whisper.

"Alright, then shhhhh" I shushed him

"Okay okkayy~~"

"Shhhhh"

"MMhmmm"

"Shhhhh" one final hush, with this one getting Simon to wiggle his butt from side to side as a way of acknowledging. I enjoyed this much more.....

I spent a little more time working the underside of his calves and knees, before working my way to the main show. All of his thighs were revealed to me with the underside of his ass on full display as well. My cock was nearly bursting at this point, I couldn't believe he wasn't the least bit hard.

After applying a bit of lotion I began to work my way along his silky thighs. Like before I was trepidatious when approaching the seam line of his shorts. I let my hands make multiple passes up and down the full length of his legs, just grazing the very bottom of his ass. Simon's reactions gave me confidence as he began to arch his back and raise his ass up into the air whenever my hand would make it to the bottom of his ass. His hips continue to wiggle and his sweet girly moans continue to fill the air.

"Mmmmmhhm~" Simon cooed. "Ahhhhh, hhhnnn" Simon exhaled deeply

My hands made a deep long stroke from the underside of his knee up to the cleft of his ass cheeks. Instead of moving my hands back this time, I decided to see how much I could go for. With my hands now gripping his thigh right under his ass I began to move my thumbs in a small circle while keeping my hands put.

"Aaahhhh~~ Mmm~"

He seemed to be enjoying the extra attention as my thumbs moved up under his shorts. His ass was soft and giving to my touch, it would bounce back to shape the second my fingers shifted in their spot. My other fingers found themselves tucked into the crevice of his thigh gap, a result from the massage growing too greedy. The position of my hand on his inner thigh was dangerously close to his crotch, at this point if he were fighting an erection like me I most definitely would have felt it. I was unaware of my grip moving up ever so slightly, until eventually bumping into something...

There was a hard rigid feeling against my fingers, and not in a metaphorical manner. There was literally some solid and unmoving object hidden under Simon shorts in his crotch area. I was incredibly confused. I naturally moved my hand away so as not to cause too much of an aversion. However when I switched from one thigh to the next I repeated my technique and again found my finger tips teasing at his inner thighs. This time I moved with a mission, still slowly, yet with a mission. The room was growing hot as both our blood was undoubtedly racing. Simon's sweet moans continued to fill the void of our living room as his hips rose and fell to my touch.

My knuckles eventually found the same solid object that caught my attention before. This time I didn't instantly recoil, instead I kept my composure and continued to move my thumbs in their circular motion while allowing my knuckles to graze the object. I was still just as confused as I did my best to be subtle with my questioning exploration. Simon wiggling hips did wonders To help in my cause as more then once he propelled his hips forward causing my fingers to again brush his crotch. Regardless of this, I couldn't pin point what could possibly be im simons pants.

With every inch of his visible feet and legs now massaged I began to release my grip from his thighs and back away.

"Nooooo!" Simon let out a playful groan as he felt the massage ending

"Alrighty, I think that's all you get!"

"Uggggghh! Just a little more, pweeeease!" Simon's high pitched voice gave a child like beg.

"Pffffhh, you'll have to cheat me in a bet if you want a massage that good again!"

"You're such a meanie" Simon wiggled his butt as he spoke, still laying face down.

Without much thought I placed a light smack on his ass while I began to make my move to get up.

"Eeeeeeppphh! Seeee, you're meanie!

"After that great massage, you really think I'm mean!"

"Not mean, a meanie!" Simon spoke in a teasing manner, clarifying himself.

"Well, looks like you're stuck with a meanie for a roommate!"

" I'll have to suffer!" Simon joked back

As we bantered I made my way up and started to move towards the bathroom. I moved with conviction in an attempt to block Simon from turning over too quickly and seeing my tenting shorts.

"I'm gonna wash my hands and use the bathroom." I spoke to Simon as I heard him rustling on the couch.

However when I reached the bathroom I immediately dropped my shorts before letting my already lotion covered hand glide over my hard cock. With the fresh memory of Simon's sultry body in my mind it took only a minute or so for me to shoot my load. I made sure to wash up quickly so as not to draw much suspicion.

The rest of our night was uneventful as we both soon went to bed afterwards.