Riley - Cover

Riley

Copyright© 2017 by Dread Mervin Roberts

Chapter 1

Fantasy Sex Story: Chapter 1 - Riley wishes he could enjoy masturbation as much as the girls in porn he loves. Wishes sometimes come true, but not quite as you expect. He greatly enjoys having a female form, but then needs some help changing back.

Caution: This Fantasy Sex Story contains strong sexual content, including mt/ft   Mult   BiSexual   TransGender   Fairy Tale   Group Sex   Anal Sex   Analingus   Cream Pie   Double Penetration   Exhibitionism   Food   Masturbation   Oral Sex   Sex Toys   Transformation  

I waved a farewell to Charles (never Chuck or Charlie) as we got to the intersection and kept riding my bike towards home. He lived just a few houses up along the main road, so we’ve been riding home together after school for years.

I knew the house would be empty when I got home, and I looked forward to it. I was the youngest of four brothers and for years the house was a flurry of activity. My two oldest brothers, Dale and Terry, were in college, and Hank, two years older than me and a high school senior, wouldn’t be home for hours from football practice. Mom worked at the library, and Dad a few towns over for a design firm.

I used to be frustrated to be left to myself alone, but then I discovered masturbation. For three glorious hours during football season, I could wank, rub one out, and jerk off as much as I wanted. Sometimes I would take my time, savoring the build up, and other times I would try to wrest a record number out of me.

Lately, I had been experimenting with techniques, trying to improvise. I had read of a few solutions online in some forums. Bananas peels, some melons carefully prepped. I took out the trash anyway, so it was easy to dispose of evidence. My current favorite was a well lubed plastic bag inserted in the center of a rolled up towel. A large bath towel gave it plenty of size so I could ride it, and the plastic bag, besides being slippery, also made cleanup easy. I had experimented with anal insertion, but it was awkward, and didn’t seem to do much for me.

I would watch porn all the time of women masturbating. I was so jealous of how easy it seemed for them to hide their activities in public, and the variety of sex toys that they could use. Some of my favorite videos were girls who would use improvised sex toys, or giant toys, or best yet, would use sex toys secretly in public. There was no way I could ever get away with getting off outside the house.

This Thursday afternoon wasn’t different. I watched all sorts of smut of my laptop and went for the lengthy build-ups, coming a few times. The usual cleaning up work before people got home went quickly.

Mom and Hand got home and she busily started prepping food for Dad to grill. He got home shortly after them, and our family went through all the usual chatter over dinner. Mom guessed correctly that Charles wanted to crash on Friday night, a frequent occurrence, since we had spare bedrooms and he shared one with his brother in their smaller home. I was asked to pick up some groceries on the way home, which was fine.

Friday felt like a usual day too, for most of it. On my way to the small grocery store between school and home, I noticed something unusual. It was a strange looking small shop next to the grocery. I don’t even remember there being a building there, so I stopped to stare at it. A carefully hand-made large wooden sign declared it to be “The Wish Shop”. It was an oddly antique looking building, made of rounded stone, with no windows, and a large central door made of wooden planks and bound with some black metal in wide beams.

“This feels like a badly written story,” I thought, amused. I went past it and picked up the few things we needed before the big weekend grocery run. But all through my winding way through the aisles, and even while the cashier, Mary, told me to relay a ‘hello’ to my mom, I couldn’t stop wondering what was inside. As I left the market, I wanted to turn left towards home, so I was surprised when I found myself a few steps to the right, toward the strange shop. I parked my bike at the rack in front of the store, not at all sure I remembered there being a bike rack here before.

When I eased the old wooden door open, the gloom inside was thick and my eyes took a moment to adjust. The door thunked closed behind me as I looked around. It seemed like any number of the little antique stores I would get dragged through for hours, just most everything looked like it was old wood, with a little glass here and there. Through an arch in the back stone wall, an old man shuffled through to the front of the shop. He had all of his hair, quite long, and white as cotton, though it all hung from his head like a thick, straight curtain. Despite his small, slow steps, he looked as solid as the building. His voice was gravelly, sounding like a river bed. “Welcome, welcome. What sort of wish were you looking to have?”

“I ... I wasn’t looking for any sort of wish. My feet seemed to just carry me in,” I answered nervously.

“AH!” he exclaimed. “The best kind of wish. The wish of a heart. Those the mind reject, but the heart will act to take without the mind’s help. Come!”

He started to shuffle towards an ornate box on a table. It was carved and about the width of my arm. I could feel my heart pounding, but felt driven forward to stand at the table next to him. He lifted the lid with a strange symbol carved into the polished top, revealing a rather plain looking scroll. He lifted the scroll and turned to me, grabbing my hand and putting the scroll into it.

“There. This will give you your heart’s wish.”

I started to unroll it and he stopped me. “No, I mustn’t know what it says. It is your wish.”

“What will this cost?” I asked, waiting for the huge number.

“It is my task in this realm to bring wishes, Riley. By you accepting it, you remove from me a small measure of an obligation, an atonement. If your wish has a cost, it is not paid to me, but it will reveal itself. Now, you must go.” He grabbed my shoulder with a surprisingly strong hand and steered me to the door, pushing me out of it before I could even think to ask anything else, like how he knew my name.

My bike was lying on the ground, the bike rack gone. I went to pick it up, and as I did, I heard a loud clank as the door closed behind me. As I stood, levering my bike back up, I stopped abruptly in bafflement - the whole building was gone. It was back to being an empty lot. The only proof anything had happened was the scroll still in my hand.

“Are you kidding me?” I asked the world in disbelief. No one answered, of course. I rode slowly home, the scroll now tucked into my backpack.

The house was empty as usual. Today was an away game the next town over, so it was a microwave dinner kind of night, my parents there with Hank until almost midnight. Charles wasn’t going to arrive until after dinner at his house, so I had several hours. This was the sort of stretch that led to the marathons of orgasms, but today, I was preoccupied by the old looking scroll on the kitchen counter. I stared at it for a while, then finally gave in to temptation. Reading it couldn’t hurt, right?

To gain the pleasures that your heart wishes to seek
Will only take but one minor tweak
To unwrap this gift you have but to say
“Flargmth grembella frway”

There didn’t appear to be anything else on the scroll.

“What the hell?” I muttered. “What kind of garbage is “flar-gemth grem-bella fr-way’?”

Nothing happened, even as I realized I said it out loud. No flash. No poof. I looked down at myself and nothing was different. I even looked in my pants to confirm my cock was the same.

“What a load of bullshit,” I grumped and threw the scroll into the trash.

Trying to put the whole thing off as a really stupid hoax, I went on with my afternoon’s plan. I wanted a nice slow slippery round first, so I brought a plastic bag into my room, along with a towel. I had a few bookshelves; a desk in one corner opposite the door, on which my laptop rested; and my bed next to the door. There were windows on one wall, but I kept those curtains closed, and a closet on the wall opposite my bed.

I popped open my laptop and browsed to my porn stash. I opened a nice strip tease video to watch while I undressed, and put the machine on the bed. I could feel my cock pulse beginning to swell as the woman on my screen, a cute punk-y brunette, started to play with her shirt in a well lit bathroom. I removed my clothes, and sat down on the edge of the bed. As my hand closed around my hardening shaft and I started to give the first tug, I blacked out.

When I opened my eyes, I sat up quickly, feeling a little dizzy. I couldn’t have been out that long because the video was still playing, and Punky had just removed her bra. I glanced at the playback controls and it had just been about 5 seconds. I relaxed a little and looked down to see if I had damaged myself.

I screamed.

My scream sounded wrong, so I stopped.

I closed my eyes, willing myself not to panic.

I peeked again at my crotch between slitted eyelids. There was no penis there at all. I closed my eyes hard.

“This isn’t happening. This isn’t happening.”

My voice sounded wrong.

I breathed deeply and opened my eyes, looking down at my body. I realized one of the many things wrong was that my chest was sticking out. And while I wasn’t very hairy below the neck to begin with, what I had was gone.

I cautiously raised my hands to touch my chest, and even my hands looked somehow wrong. I pressed my palms against my chest and ... it felt different. I was clearly sticking out, even my nipples were protruding further out than before.

I nervously stood, mildly dizzy, and turned to close my bedroom door, which had a mirror mounted on the back.

My heart felt like it stopped. I had seen countless thousands of naked people online, but I had never seen a naked girl in real life. The closest was our neighbor’s granddaughter, Cassie, a girl a only a year older than Hank. She was living there while attending a local college, and one time, at a party down the street, had flashed her lovely breasts at me once on a dare.

The sandy blonde girl in the mirror looked to be about my height, slender, and with a modest pair of breasts. She didn’t have much hair between her legs, so I could make out her outer lips protruding just a little. I looked up at her face and we locked eyes. Her face looked almost like mine. She looked as shocked to see me as I was shocked to see her.

I raised my hand to feel my face, and she did the same.

It finally clicked.

I screamed again as I realized I was looking at me. NOT ME. I screamed until I ran out of air.

I felt silly then, screaming alone in an empty house.

The scroll!

I ran naked through the house, grabbed the scroll from the trash and ran back to my room.

It had rolled up again in the trash, so I slammed it on my desk, unrolling it. The text now read:

Have no fear, it’s time to have fun,
With pleasant work, the spell’s easily undone.
When all woman’s chambers have tasted life’s seed,
The man deep inside will again be freed.

I sat down hard on my desk chair, causing it to roll slightly away from my desk, the scroll falling onto the floor and rolling towards the bed. “Okay,” I reassured myself, as the chair slowly spun. “This is temporary. It’s ‘easily undone’.”

I had spun enough to see the mirror again in the corner of my eye, so I turned the rest of the way to look at not-me.

I was pretty cute, even slumped in my chair. I sat up straight and watched as I reached my hands up to cup my chest. I slid my hands all over them, squeezing them gently. I felt an odd twinge between my legs, so I spread my knees apart. I couldn’t really see from across the room, so I got up and tossed the pillow from my bed on the floor in front of the door. I sat on the pillow and leaned back, opening my legs wide. Doing this slightly parted the outer lips to reveal pink flesh. I was getting aroused at the sight and instead of feeling a urgent hardness respond, I could feel myself growing wet. The inner lips were getting just a little bigger, which was fascinating.

I put my fingers against one to feel it and it felt a little rough. Remembering from many amateur porn videos, I licked my fingers and tried again. As my fingers slid over the tender parts, it felt like little sparks of pleasure climbed my spine. I repeated the caress down the other side, marveling at the sensation. It felt almost like when I would play with just the head of my cock, but somehow different.

As I slid my fingers down between my inner lips, I could feel the hot, wet warmth of my opening. Curious, I started to circle the rim, and felt my fingers get wetter. I watched myself in the mirror nervously push two fingers inside. Between the incredibly erotic sight, and the amazing feeling from between my legs, I let out a moan.

I realized that the spell said it would come undone, and I wanted to never forget this moment. I moved the laptop on my bed to the center and started up a webcam recorder. I moved my pillow back against the headboard and settled against it, the laptop between my spread legs.

I resumed what I was doing, gently running my wet fingers around my pussy lips, then plunging them inside. It felt incredible. As I explored deep inside myself, my palm pressed against what must be my clitoris and I groaned as I felt the pleasure wash up my body. With my male body, I would feel intense pleasure in my cock from all sorts of activity. But, it always was pleasure from my cock. This, this was a whole body experience. I could feel everything coming alive and the urgency I usually felt as a male started to creep in.

I started rubbing myself faster with one hand, pressing two fingers into myself frequently, and with my other hand began to explore what stimulation my clitoris liked. I had seen a wide array of techniques, so I breathed heavily as I tried a few. It seemed like quick and light rubbing across it, with occasional harder presses was what was working. I could feel this amazing tension rising inside my body. I wondered what it would feel like to use a toy and the dirty thought apparently pushed me over the edge.

I felt my breath catch as streaks like lightning crackled along my spine and my muscles tensed up, my body quivering. Then this glorious, hot feeling washed outwards from my pussy, and I could not help but let out a guttural laugh and I felt the release.

I felt a little sensitive then, so I stopped moving my hands.

I sat up, stopping the recording on my laptop. It churned for a second, then opened the folder with the new video. I popped it open and watched in fascination. I was beautiful! And fucking sexy!

The heat that I had been feeling radiating hadn’t died down, and while I was watching my own orgasm, I felt it building again. I had to know - what did it feel like to be penetrated?

I considered my options. I had seen all sorts of things, but this would be my first, and I didn’t own anything appropriate for the task. I thought about it for a moment, then threw on my robe and went to the kitchen. I fetched one of the cucumbers I bought earlier today and brought it back to my room.

I set my laptop up to record this again, and I wished I had more cameras for more angles. I knelt on the bed, my knees spread open a bit. I was still very wet from before, so I slid the bumpy skin gently over myself, getting the end of it very slick. I held it upright, aligning it by feel more than sight. With it placed against my opening, I eased myself down, letting my weight help push. It felt so strange opening me up. I pause with just the tip inside me and shuddered. I stroked my skin all over, caressing my breasts, my belly, my ass, my legs. It felt like my whole body was wanting to be a part of this moment. I lowered myself further, and further, just inching the monster inside me. I lifted up a little, and I could feel my lips gripping it, so it came up with me. I reached down to pull it further out, then eased back down onto it, further than I had before.

I felt so full! I wanted more. I wanted to feel the thing sliding in and out, pounding into me. I turned around, and bent at the waist, letting my torso rest on the bed, my ass high in the air aimed at the camera. I started pulling and pushing with it, thinking about what it must feel like to have this be a hot cock, with another person controlling the tempo. With a suddenness, I came again, this time my insides fluttering around the cucumber. I jammed it almost painfully deep and my muscles seized up, then relaxed as wave after wave of pleasure rocked every nerve.

I eased the cucumber out of me and fell onto my side. That was ... amazing. Just amazing. I had never felt an orgasm that strong before. It was everything I imagined, wanted it to be.

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