Well here I am laying besides my best friend and roommate turned lover after a rather eventfull evening and even better night. Dear Luna, I still can't believe it. And is stranger I am afraid to admit I enjoyed every moment of it. 'Sigh' I might aswell recount how it all began then.
It had been a loooooooong week at the academy, and I finally had been able to catch a few ZzZ's on the couch of my dorm room. I still don't really get why my parents insisted on me enrolling into the academy. Sure learning about weathermanipulation and the natural magic of my kind was neat and all but my talent is in the stock-exhance. I`m 19 and already made for live thanks to a few clever investments I made over the years. Not to brag, but I highly doubt many can claim to be a major shareholder in a snowflake-factory and a lay-crystal mine.
So please forgive me for sometimes being bored out of my skull learning the basical principals of cloudmaking and lightningwrangling. But it gets me off the streets and doing atleast something resembling usefull for the time being I guess.
My little time of peace had been disturbed when my roommate dripped in the room, it had been asif any bit of cheer and joy had been drained from it. Opening my eyes I could see Cherry shuffeling towards his bed and flopping down on it quietly sobbing.
Now this was nothing new for him, from the day we met a few years ago he had shown to be a rather emotional colt. But could anypony blame him?
I mean come on! His parents named him Cherry Blossom for Celestia's sake. Combining that with his rather femininen appearance it was simply asking to be a target for bullies. It had come as no surprise to me that he infact prefered colts and stallions over fillies and mares. But in the beginning it had led to rather akward discussions about 'companion rules' in our shared room. We agreed on placing a small blue ribbon on the doorknob as a signal for that. Of course it had let to him joking that I was welcome to join in at anytime.
And that had been typical of the Cherry I had come to know, always in for a good joke always in for a laugh, an rather infectious laugh at that.
But that laugh had been far from this room now. Slowly I walked up to him and placed my hoof on his shoulder. “Hey, everything alright?”
The sight I saw would stay with me for the rest of my live, of that i`m sure.
Cherry only raised his head slightly, his emerald green eyes ridden with tears. But that was not what had drawn a stiffled curse of outrage from me. Across his muzzle from eye to nosetip had been a gash. Luckely it had not been very deep, but it did ocassionally drip a bit of blood on the sheets below him Cherry himself did not even flich at the wound, he just looked at me and before I even noticed it he had trown himself in my front legs hugging me tightly as he cried his heart out.
Through the sobs I could hear bits and bobs of what had happened and used common sence to tie it all together.
After much debating he had asked a classmate of his out. This colt did not take kindly to it and his friends decided to help Cherry to remember never to even look in the colts direction again.
My wings ruffled a bit, conveinging the rage I felt at the sheer nerve of them. Cherry wouldn't even hurt a fly, he was as harmless as they come. He didn't deserve this and I had half a mind to track these colts down and give them a taste of their own medicine. But first I had a colt with a broken heart to cheer up, and thus I merely held him and let his tears flush the sadness out a bit.
Finally after a good 20 minutes the sobbing seemed to die down a bit and I could finally let him go. Smiling a little bit I had gently asked if he was feeling better. A small fleeting smile and a nod was all I got as a reply, but it was more then enough. There was still sadness in those eyes, but I think it was more about the rejection he had received rather the treatment stemming from it. But that was not somerhing I could really help with, feelings and such were never really my forte. But seeing him in this state was even a tad hearbreaking to the likes of myself.
Walking back towards my own bed a pinch of emptiness struck me, I did not fully understand at that point but a part of me actually was missing feeling Cherry's warm fluffy fur rubbing against me. And that was somewhat surprising to me, puzzeling even. I briefly wondered how he kept his fur so silklike soft, even a plushy was rockhard compared to it.
That thought had not entered my mind when I knew what I could do to cheer him up, and I for sure was not going to like it. Sighing a bit I walked over and poked the downtrodden colt.
“Get up lazybones, youre a mess and thus im taking you to the only place which can fix that and get that nasty cut checked. So get out of bed and snap out of that flunk or I will drag you by your prettified tail to that spa you always rage on about.”
It wassnt my best line, but it was enough to get a rather cute giggle out of him. Right now I now know why I had found I cute then, but at that moment it was yet again a rather confussing thought.
Remember I said I was not going to like it, well I lied a bit. I absolutely HATED it. A bunch of mares fuzzing over your coat with all kinds of lotions, preening your wings, hell at one point one even tried to dye my mane and tail. But the hottub had been nice enough, just laying there enjoying a good soak and letting all the stress of the day wash away.
My enjoyment quickly chanced after getting out to dry myself off when after about being gone for an hour Cherry Blossom entered the small changingroom. My mouth just fell open from the sight. I knew he was into cross-dressing for 'private affairs' but I never saw it myself. Had I not know him personally I would have had great difficulty picking my jaw up from the floor. He was absolutely gorgeous in that outfit.
A small, but not sluttly small, shortskirt beneath a flowing long blouse. The skirt itself was revealing, but not as much as one would think, leaving the typical parts well hidden while accentuating the round fillyish plot and flanks. His broken white mane had been brushed into long strands, cured from its normal curly form, and tied in a loose pony-tail hanging freely while a few loose strands obscured the cut on his face, giving him a rather seductive look in his only visable eye if you combined it with the coy smile formed on his lips. The gently applied make-up betrayed that the spa-ponies had aided with it.
The parts of his normally light rosé* collored coat where almost shining in the dimmed lighting of the changingroom. If he would walk past some of my teammates from the cloudball-team like this I knew many of them would say something in the likes of “Damn, i`d tap that”
For only a very faint bulge at the underrim of the skirt betrayed that the Earth Pony infront of me was actually a colt.
As he walked towards me I was almost completely mesmirized by the swaying of his flanks and the gentle waving motion of his tail. I had not even noticed how close he had gotten to me until he lifted my lower jaw back in its normal spot. Right before softly placing a gentle kiss on my lips.
It was swift and fleeting, but it made a lasting impression. As he withdrew blushingly I could still smell the gentle perfumed scent of ointments and taste him on my lips. I could barely move because of all the thoughts raging in my mind. The combination of those with his looks where enough to test my willpower to the maximum as only sheer will was holding me from simply trusting myself back onto those enchanting lips.
I must have been quite a sight, trembling legs and wings flared like there is no tomorrow, for a few moments later I could feel his breath near my ear right before he wispered. “Thank you, thank you for trying to cheer me up and just being there for me. Three years, three years you have been there to pick up the pieces when I fell in shembles again.”
A soft nuzzle followed before a second soft kiss found my lips again, this time it did not stay with a kiss alone, a gentle hoof found its way to my little soldier who already was starting to stand at attention.
As he gently started rubbing his gaze fell down to his still growing target. I was about to speak up, but the soft ministrations had been to well placed and made thinking straight hard. Cherry seemed to read my thoughts and simply spoke in a soft voice “shhh.... Don't worry, we are alone. I made a 'special' request to the spa-ponies to let us be for a moment. Now just relax and let me thank you properly.”
His rubbing intensified a little, adding in smooth circular motions as he pushed the semi-erect flesh on my stomach. A small moan had escaped my mouth before I could stop it, which seemed to spur Cherry to take his plan to the second stage. Agonisingly slow he withdrew his hoof and moved his muzzle towards his price.
It did not take long before the tip of his tongue started to stroke the tip of my stallionhood. Expertly drawing circles on the surface. Ive had fillies teasing me like this before to get me arroused, but their skill paled compared to what he could do. Within moments I was fully erect and flaring.
At that point he had stopped the treatment in favor for the real deal. Expertly his tongue drew long lines arround my stallionhood as his muzzle hovered less then a cm. from the tip, each stroke seemed to last a enternity and was ended with him sofly sucking on the exposed flesh and the small opening in it.
At first I did not dare to look, but as he finally took my whole member in his muzzle and started to suck and twirl his tongue in earnest I could not help myself. The sight of his blushing and bobbing head, his delighted expression and ocassional moan of pleasure as a drop of pre-cum found its way to his taste-buds only added to my experience. Only the knowledge of being in a public place kept me from crying out from pleasure caused by what must have been the best blowjob I had in my life.
But to all good things had to be a end, I could feel the presure building in my balls and my own shallow breaths kept becoming more ragged with every passing motion.
Past experiences with mares told me to atleast warn, for they never liked it when shot straight in the mouth. Most mares even hated it.
Groaning and straining to even form cohesive words without them ending in a moan of cry “Ch- Cherry, Im close. Ooh, dear Luna i`m” where all I managed to get out as he had stopped bopping and began feverishly licking and twirling his tongue arround on my senstive flared tip, turning every word I wanted to say in a throathy moan. Seconds later, I came. Thick strands of my white goo flushed out straight in his mouth and all he was doing was bravely attempting to catch it all. But even his seemingly masterlike skills could not allow him to have everything as small drops started leak from his lips while greedely gulping down my 'gift'.
Letting go of my member with a pretty loud popping sound he raised his head and looked into my flustered and still spaced out eyes. The ammount of pleasure he had just caused me had almost blown my mind and I was not prepared for his next move. As ferosicous he had been at servicing me was as gentle he was with his third kiss. Forcing his tongue into my mouth I could only go along with it, his treatment had made me into nothing more then putty in his hooves. The flavor was nothing like the sweetness from before, but I guess it had taken my mind a few moments longer to recognise that I was not tasting only him. Allong with his invading taste-organ he had brought a few somewhat slimy and salty strains of liquid with it.
My own semen, he was feeding me my own cum. But what shocked me even more was that both my body as my mind gratefully accepted the gift as I was wrestling the invader for dominance in my mouth.
When he finally withdrew his lips from mine and I could swallow the last strands of saliva and semenmix he left in my mouth I could only stare in awe at the colt infront of me. A masive blush decorated his cheeks and he was afraid to even look me in the eye. Lowering my gaze I saw that he himself had been arroused aswell. The memorie of what just happened combined with his looks were waging war in my mind with a part of me who was screaming that it was wrong.
Normally I would be seeking profssionial help for this since the latter side was losing the war very rapidly. but I found myself not caring anymore as I stared into the emerald eyes of the cross-dressed colt infront of me.
In that moment of silence the 'normal' part of my consious had been shattered, leaving behind a single thought, one I would not have dreamt of ever having. All of my being was focussed on the same thing, I was going to treat that 'filly' to a nice dinner at a fancy place and then once we get back at the dormroom I was going to make him MY little 'filly' and make him forget all about that jock he had been chasing.
My thoughts were interupted by Cherry, he had broken eye contact and was staring down at the floor. Blushing heavely while pawing a bit at the floor. Obviousely nervous about something
“So euhm, I guess im moving out the room now eh?” A small tear formed, obviousely he had taken my silence the wrong way. “Im the one who made things awk”
Refusing to let him even finish I simply placed my hoof on his lips silencing him. “Listen, who said anything about having to move out. But you did do something I cannot easily forgive.” I thought those words might be a bit funny, but his shocked look said a completely different tale. A large smile was plastered on my face as I continued in a teasing tone. “You forgot propper ettiquette Cherry. I mean, im no marenizer but I thought you knew better then this. Your supposed to take somepony out first. Dinner, movie, picknick under a moonlit sky... Anything, you dont just rush into sucking ones dick right away.”
Removing my hoof from his lips I used the same one to raise his head to eye level.
“So in that light, and seeing how you are all dressed up with fancy make-up and all. How about it, up for grabbing a bite to eat?”
Using a strand of hair to cover the wound across his face he looked at me with a wide open eye filled with something more then just hope.
“As in a datelike grabbing a bite to eat?”
A chaste kiss was all he received as a anwser before I turned arround and carefully and playfully swatted him with my tail and heading to the exit. A few steps from the door I looked back towards the seemingly petrified colt “You coming or what?“
~ ~ ~ ~
Well I got to hand it to Cherry, he kept of his persona incredibly well. Playing the part of a exited filly going on a first date with the colt that caught her eyes. Not even the trained eyes of the waiter saw through it as we ordered.
Leaving the restaurant behind, we were walking towards our dormroom. He leaning into me with me draping a wing arround his back. I`m not prone to say this, but it had been absolutely perfect.
After dinner I just did what I thought would go on any date. A nice stroll through the park, followed by simply sitting on the hill there watching the stars, enjoying the others warm body next to you and the comfort and company it brought. Somewere along our walk we met with what I think was a ex of Cherry. He simply said I needed to lift the skirt, cause my date wassnt what she seemed. Claiming it was to prevent any surprises later on. I just responded by placing a passionate kiss on Cherry's lips who in return gratefully accepted and returned the intent. Causing the colt to leave us alone, honestly I think he was just trying to get my 'filly' for himself.
Now sitting in our room sharing a bottle of cider I got sometime ago from back home in Ponyville it was time to put the second stage in motion. Slowly I crept a bit closer to him, and turned his face towards mine. Before anything could be said I pressed my lips on his and started to prod with my tongue, asking to enter. A gesture accepted without any resistance. In the back of my mind I still could recall how good he had made me feel and every fiber in my body wanted to repay the fav or.
Slowly leaning in a bit more I placed a bit of presure on his body, gradually increasing the presure until I managed to gently knock him on his back on the pillows we were using as a seat.
With a seductive smile I crawled towards him and lay on top of him, causing the fur on my belly to rub against the fabric of his clothing. Agonisingly slow I brought my muzzle to his ear softly wispering “I still owe you for making me come this afternoon, and seeing you in this cute little outfit just makes me want to repay you.”
Using a hoof to lift a bit of the skirts fabric away from his stallionhood I carefully alined my own ontop of it before making soft bucking movements while pressing our members together. I found it strange but also rather nice to have absolutely no resistance. He was not fighting it, he was accepting it. Simply laying there squirming a bit as I used my appendage to masage his, a feeling not completely unpleasant to say the least. To add to his pleasure I started to softly kiss his jawline and nibble a bit on his ear. Earning me a few suppressed moans before I wispered my final sentence in his ear. “Just relax and enjoy, because tonight i`m going to make you my little filly.”
While adminstrating soft touches to his member and trailing sloppy kisses on his neck I fumbled with his clothing. It took me a while but I did managed to get them off intact. My prize had been twitching hard against my own member. It was slightly smaller then my own, but I had no idea wether that was normal or not. It`s not like i've seen many colts standing at full like this before.
Drawing closer by simply trailing my muzzle allong his chest fur. Honestly I had no idea what exactly I was doing and part of me was really anxious about this.
When I got closer I could actually smell his tool, nothing I can do can describe it. I still dont know what came over me, I had planned to lube him up a bit before taking him. But the scent of it, that alluring smell just drew me in. Softly I lapped at the tip with my tongue almost instantly rewarded with a familiar salty taste, albeit this time it had been much and much sweeter, and a surprised gasp what turned into soft moaning after I started licking the tip asif it had been a large lollypop in long drawn-out movements.
Encouraged by a foreign hoof softly stroking my mane and the already seriousely heavy breathing from the colt beneath me I placed the now rock hard fleshrod in my lips.
I just hoped I was doing it right, alterating between gently sucking and rotating my tongue over the sensitive tip.
I was focusing so much on my movements I never heard the increasing volume in groans stemming from above me, nor did I hear the muffled cry from Cherry reaching his limits. The only warning I ever got was him placing his front hooves on my head pressing my mouth down on his stallionhood right before it started to twitch like a madpony and discharged several shots of his salty-sweet cream down my throat.
Looking up I saw the most adorable sight I had ever seen. Cherry had his eyes half closed and mouth hanging open. The masive blush on his face was nearing the infra red in intensity. His brain had completely failed to even resemble working order. I guess I did do something right, but now was not the time to gloat. Somehow my previous work had effects on me aswell, feeling him twitch and squirm while working his member had more effect then the strongest aphrodisiac and I was raring to go.
A few gentle yet firm licks were all it took to coat his puckered little tailhole in a decent ammount of saliva. It was bitter tasting, but somehow not as much as the few mares who had allowed me to do this. Maybe he cleaned better? No matter, it now was time for the main event. Gentle and carefull I had placed myself back on top of him. Feeling his still half hard member stroking my the fur on my stomach, it felt strange but not completely unpleasant and its second growthspurt said that Cherry agreed with that. But his squirming beneath me caused him to brush his tailhole against my tip as it waited to pierce it. His face had seemed worried somehow, asif something was not right. This worry he voiced almost immediately.
“Ash, please let me turn arround.” He looked a bit down and the cheeryness of his voice died a bit. “I know you're not like me, not a coltcuddler. So please let me do this for you so you won't have to see my face or feel my stallionhood rubbing against you.”
He had meant it, with hole his heart he wanted me to rut him. But he was still thinking about making sure it won't be awkward or gay for me. I did the only thing I could think of to respond; Leaning in and simply somther any other word from coming out from his mouth by furiousely kissing him. Hoping all my arrousal would be pouring into the kiss in the form of pure lust and passion.
When our lips parted is simply stated the obvious “I promised id make you my little filly. My little toy for the night. How can I keep my promise if I cannot see your face scruning up cutely like a few moments ago, or how I can I know im making you feel good if I cannot feel all of you in connection with my own body?” I placed a soft kiss on his lips right before I puched the tip of my member inside.
Softly I pushed further in the tight little hole. All the while the Cherry was gasping and squirming at the feeling of me invading his most private place. It was obvious I wassn't the first to visit there, he was tight but there was no resistance in the form of him trying to push me out.
Hilted up until the root in him it felt better then anything I ever had felt before. I had expected it to feel strange and wrong, biology taught us ofcourse that two males should not be together this way. But if it was so wrong, how could it feel so right? Slowly starting to move I could feel him using his muscles to gently masage my member even when I was inside.
I was trying to be gentle at first, but a few strokes in he was urging me to go faster and harder. I was pounding quite hard into him, it felt amazing. My own pre helped him lube a bit more and as he loosend a bit from my treatment I was getting full reign over his bottem. Unbeknown to me, me slamming into him while still somewhat squishing my body against his was sandwiching his member between two moving and squirming bodies. Making him feel like I was giving him a fuzzy hoofjob.
It did not take long for me to get close to a finishing point, and by the sound and looks of things Cherry was very close aswell. I had been given full reign up until now, but that was about to chance. Using strenght I did not know he even possesed he pushed himself up, forcing me out of him and the both of us in a sitting position. His rockhard member was swaying in my face as he placed himself on top of mine and slowly lowered down on it.
I had to lean back a bit using my front hooves to support myself as Cherry was riding me. Unlike my hard and uneven movements he was rocking at a decent place with almost inpecable timing. The pacing had been perfect. Swaying in a circle as he forced himself up and down made me lose my mind. Somehow this felt even tighter then my first entrance and much much better.
My rider seemed to agree, a few moments in and he clamped down on me forcing me all the way in before invading my mouth with his tongue. Somehwere halfway our kiss I felt something warm shooting on my chest while his little hole clenched my member tight. The sensation of the incredebly tight grip, his manic kissing was enough to drive me over the edge and fill him completely with my cum.
We stayed in that position a few minutes as we caught our breath and ride our afterglow out into the realms of sanity before he stepped of from me. His plot was covered in my goo, I guess it had spilled out a bit. But that was not important, there was a look in his eyes. They were not filled with lust or passion, but it was something else. I could see his chest puff in and out as he took a few deep breaths before he approached me. His hoof wiping his cum from my chest while he looked in my eyes pleadingly.
“Ashen, would you stay with me? Be there for me like you were today?” My confusion must have shown pretty well for he spoke again before anything could be asked. “I mean would you like to be my coltfriend?”
I was rather surprised about it, but the memorie on how he good he made me feel just now was still fresh. I awnsered without thinking.
“I don't know Cherry, but i`ll never know until we try. . But on one condition. You tell my mothers that they propably won't be getting grandchildren from me.”
And well, thats how I ended up here. With Cherry Blossom in my hooves lying in my bed as my newfound lover. And who knows, maybe it might even work out.
Dear dairy,
I can't believe it. After nearly three years of pinning after him and failing plan after plan to actually get that cute roommate of mine to notice me it took me trying to get over him by trying to have some fun with that Unicorn who had been showing interest in me (and getting beat up by him and his friends cause it was all just a joke to them) to get him interested!
But nevermind, after he screwed my brains out I popped the question and he said YES! Can you believe it, he`s finally mine now.
Signing off,
Cherry Blossom.
Author's Note
* Cherry Blossoms coat color is similair to Sakuras (from naruto) haircolor
