Riley - Cover

Riley

Copyright© 2017 by Dread Mervin Roberts

Chapter 2

Fantasy Sex Story: Chapter 2 - 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  

Pretty early the next morning, Charles left to go home. His family was going out of town for the long weekend. He seemed to have decided that the best coping method was denial. We played the usual games, with a quiet tension under the silences. Every time I had tried to talk to him about what happened, he cut me off. I eventually gave up.

Not long after he left, Dad and Hank started packing the car. They were also taking advantage of the long weekend to go visit Thomas, who wanted some handyman help in his apartment half a state away. Since I didn’t share my dad’s knack like my brothers for fixing things, I opted to sit this trip out. They packed up efficiently while Mom and I enjoyed a calmer morning.

After they left, Mom asked if I wanted to join her and Cassie, the neighbor girl, for lunch later. Mom and her connected quickly after she had moved in, often doing things together. I declined politely, as she was expecting, and went up to my room.

In the quiet of my bed, I kept thinking about what had happened. It freaked me out, but it also had been the most amazing thing to ever happen to me. I grabbed me laptop to check that the recordings I had made existed, just to confirm it wasn’t some bizarre dream. The folder was there, and when I opened it, it showed stills from the middle of the videos as the file icons. One was girl-me with my fingers buried deep inside. The other showed girl-me with my head thrown back and the produce buried as I rode it. My cock surged to life, so I pulled my pants down without thinking too much about it and grasped my cock.

When I woke up, I panicked. “Oh no! No no no no...” I thought as I looked down, confirming what I feared.

I WAS A GIRL AGAIN!

I breathed, trying to calm down, trying not to panic. I got up and dug the scroll out of my desk drawer, but it said the same thing.

I sat, trying to consider this. Both times, I had turned into a girl when I started to masturbate. “Does this mean I can never jerk off again?” I wondered aloud.

I was interrupted by a knock on the door. After raising a pack of boys, my folks didn’t open the door unless invited to - there was apparently a couple of embarrassing incidents. I tried to lower my voice again, “I’m getting dressed” being the lie my panicked mind produced.

“Ok,” Mom called from the other side of the door. “I’m folding laundry and need your help, so come down in a minute.”

I could hear her walk down the stairs. “Shit!” I hissed. Charles had helped me turn back, and it worked, so I knew it was possible, but there was no way I could get him back from a trip, and certainly not without raising suspicions. “Oh god, what can I do... ?” I moaned. Knowing Mom, she’d be pissed in 5 minutes and come up here to collect me. “Fuck! Fuck fuck fuck fuck fuck,” I ranted helplessly.

There was no way out of this. I had already learned just how little I can successfully hide from my parents. The only thing to do was explain everything. “I’m so fucked,” I prophesied to myself, willing myself to take the right steps.

I opened my door, my heart racing and I could barely breathe. “Mom?” I called.

“Yeah?” I heard from the living room.

“Can you come up here?”

“Right now? I said I needed your help down here.”

“I know, but I have something important to talk about.”

I could hear the sigh from here as she began the trip. I softly closed the door and braced myself against it, not to hold it shut so much as to hold me up. Listening to her steps on the stairs was one of the longest minutes I have ever experienced.

“Mom,” I called out as she walked down the hall. “Something really crazy happened to me and I need you to not freak out, ok?”

I felt as much as heard her try to open the door. “Riley? Define crazy.”

I sighed and stepped back, opening the door. Her look of shock will stay with me. “Riley, why do you have a girl in your room?” Her voice was raising as she processed, getting angrier.

“No, Mom, this is me. I’m Riley.”

She stared at me, looking hard at my face. “N-no, I saw Riley 15 minutes ago.” She looked down, realizing I was wearing the same clothes, and looked back up, scanning my face, which did look a lot like my boy-me face.

I wasn’t prepared for her to fall over, and I lunged to try to catch her as she fell in the hallway, and I only just barely managed to prevent her head from hitting the wall or floor. I had never seen anyone faint and it was terrifying. As she lay there on the carpet, I didn’t know what to do as I just held her head.

Thankfully, her eyes opened after just a moment. She looked up at me, then quickly squeezed her eyes shut. “Riley?” she asked quietly.

“Yeah mom?” I answered as I removed my hands from below her head, letting it slide gently to the carpet.

“You ... you’re a girl now.”

“Um, yeah.”

“Ok.” She didn’t move or say anything for a minute. “I am going to go downstairs and make another cup of tea. Give me a few minutes, then come down and you will tell me everything.”

I nodded, but realized she wouldn’t see it. “Sure mom.” Leaving her there, I returned to my room and sat on the bed, ignoring the open door. I could see part of her as she got up, then heard her walk downstairs. I waited for what felt like ages to hear the kettle beep that it was done, my thoughts swirling around, racing but getting nowhere.

After a couple more minutes, I quietly walked into the hallway and crept halfway down the stairs to peek into the living room. Mom was sitting in on the couch, so I continued down more loudly, and joined her by sitting in one of the chairs. Not knowing where to start, I kept silent as she studied me.

“Alright. Start at the beginning,” she said, her voice sounding calm but strained. “No interruptions - just what happened.”

“Yesterday,” I explained, “after I went grabbed groceries, there was a strange shop next to it that I had never seen before. It looked old and said ‘The Wish Shop’. I wasn’t going to look, but it was like I was drawn in. There was this weird old guy and he said he had to give people wishes, but that he couldn’t know what the wish was. He handed me a strange scroll, said it would cost whatever the scroll said, and pushed me out of the shop. When I got home, I read it. A little while later, I woke up like this. The scroll had changed, and explained how I could make it wear off. Charles --” I blushed “-- helped me do what it said, and I changed back. I didn’t know it would happen again, and I don’t know how I can change back unless I can get Charles to help again.”

Mom nodded, then thought for what felt like an eternity, the silence weighing heavily on me.

“What was your wish?”

“Um,” I paused, not knowing how to have this conversation. “I didn’t know. The old man said it was my heart’s wish.”

“You want to be a girl?” she asked neutrally.

“ ... not exactly.”

“How did Charles help you change back?”

I sighed, “Look, the rest of this is going to be about sex and the only way I can talk about this is to pretend you’re fine with all this or even not here.”

She nodded and sipped her tea.

I screwed my eyes shut and blurted the rest. “I wanted to know what it was like to get off like a girl. When I was going to ... you know ... that’s when the change happened both times. When I read the scroll after, it said that to change back, I needed a man to... ‘spill seed in all three chambers’.” I heard a sharp inhalation, but ignored it, squeezing tears of frustration that were building up in my closed eyes. “So, I asked Charles to help me and he did, so I was back to normal by the time you got home. What I did not know was that it would happen again the next time I tried to ... So, I guess I can’t even try to, erm, without turning into a girl. And I need help to change back, and...” I broke down, sobbing, lost and overwhelmed.

I felt my moms arms fold around me then, and she just held me as I cried and cried. “Ok, it’ll be ok,” she reassured me. She stroked my hair gently as my misery slowly ran out of steam.

“There’s something we never told you, Riley,” she spoke quietly to me. “When I was pregnant with you, the ultrasound was read wrong. They told me that you were going to be a girl. And I was so happy to hear that after three boys. I was finally going to have a daughter to connect with. And when you were born, I loved you all the same, of course, but I knew I would never have a mother/daughter day.” She paused, then sounded hesitant as she asked, “do you think we can try that today while we figure out what to do?”

I was speechless. I had expected Mom to lose it, to go crazy with this crazy situation. And instead, my wish was helping her fulfill hers. I nodded, knowing she would feel it as she held me. She squeezed me tighter, then let go, sitting back down.

“Before I go running off with visions of the day, let’s check some basics. Do you think Charles will help you again?”

“ ... I don’t know,” I admitted. “He was kind of freaked out about being gay.” Mom laughed.

“Sorry, just sort of funny to think of a teenaged boy worried about being gay for having sex with a girl. When does he get back?”

“Um, late Monday night.”

She harumphed. “Ok. That might help with school but not with your father and brother.”

We were interrupted then by the doorbell.

“Shit, that’ll be Cassie,” Mom swore. Mom seldom swore. “Go upstairs and try to figure out something casual to wear, if you can. I’ll try to think of something.”

I scurried upstairs. As I listened to them chattering downstairs, I went through my things. Very little fit in any useful way - most things were too baggy to be trusted to stay on. I was digging in the mess at the back of my closet, looking for old clothes I grew out of, when I heard a knock at the door.

“Riley, honey?” Mom declared, opening the door. The cute neighbor was with her. “I was telling Cassie here how your father, my brother, sent you to visit, but the airline lost your suitcase. She offered to lend you an outfit so we can go shopping today.”

Admiring my mom’s ability to make up a plausible story that fast, I backed out of the closet and gave a little wave. “Uhhh ... hi.”

“Oh, you’re a cutey!” Cassie chirped cheerfully, bounding into the room and hugging me. She leaned back, grasping me by the shoulders, “Boy, I can see the family resemblance!” My mom burst out laughing. “Well, no time like the present. Let’s go raid a more helpful closet,” she said, dragging me out of the room by one hand.

Mom, still laughing, called out “have fun, girls, be back in 30!” as we headed out the door.

Cassie jabbered quite a bit about different types of garments I should pick up, most of which I could only guess at what she meant. As we got to her bedroom next door, she dove into a large closet and started throwing things at me, which I fumbled with and caught.

“We’re mostly the same size although you’re a little smaller, and I have no idea if I might have some bras that fit you. What size are you?” She said all in one breath at an impressive speed.

“I’m not sure, these are kind of new,” I answered truthfully. She laughed and rummaged in a box, coming out with all sorts of odds and ends.

“You’re lucky I’m a packrat and grew these --” she pointed at her ample chest “-- pretty quickly. I kept having to buy new bras. Not fun! Now, ditch the baggy shirt so we can see what we are working with.” She took the small pile from my hands and put it on the bed.

Taking my top off in front her felt weird - I’d never had a reason to think if I should or not before. When I dropped the shirt on the floor, she commented, “so perky, you’ll have men eating out of the palm of your hand. Maybe some women too! Here, try this one,” she said, handing me a smaller black bra.

Looking at the strappy garment in my hand, I realized I had a problem. “I, uh ... haven’t actually worn one if these before,” I admitted.

“Really? You’re champagne glass and perky, so you could get away with it, but not even to hide nipples? Didn’t your mom get you trainers?”

Not knowing how to navigate this one, I built on the lie my mom gave me earlier. “It’s just me and my dad, and he’s useless for anything girl. It’s part of why I’m here, so Aunt Sarah could kind of play mom and help me with some things.”

“Ohhh. M’kay, well, I’ll demonstrate, then help you. It’ll be like having a sister!” she declared cheerfully as she took her top off. Her sizeable chest was contained in a purple, shiny bra. I felt a curious sensation in my lower abdomen and realized that as I watch the lithe blonde girl reveal herself, I was getting wet.

Cassie quickly dropped the straps off her shoulders and pulled her arms through, then reached behind her and undid the back. She tossed the bra on the edge of the bed next to her and rubbed her lovely breasts. “Ahh, feels good to take that off. I guess you’ll see later. Ok, so, I’m a 30F, which let me tell you is a pain in the ass to shop for. We’ll have to get you measured later but I would guess maybe 28D...”

I was having a hard time concentrating on her chatter, mesmerized as I was. Cassie giggled and waved at me to get me to pay attention. I had missed something she said.

“If you’re done enjoying the view, I can show you how this works now,” she said, amused.

I blushed and nodded. She described the process aloud as she did the bra bottom band first, but on backwards, then spun it around, slid it up into place, then looped her arms through the straps. While her process was fluid, when I tried it, I fumbled in the first steps, trying to get the little metal hooks together seemed impossible.

“Here,” Cassie gently said, hooking them for me carefully. I felt the back of her hands brush the underside of my breasts and it sent a little thrill racing up my spine.

“Thanks,” I mumbled, able to get the rest done easily enough. She took a step back, eyeing my fit.

“Hmm, that’s mostly ok, but if you grow more, it’ll be DD instead. See how you’re not quite spilling over here?” she asked as she ran a hand along my skin right above where the top of the cup was pressing lightly into my skin. My knees went a little weak and I tried to not stumble. My face felt hot, so I thinking I was blushing furiously. “People hear anything over C and they assume huge, but it’s all about ratio. You’re slender so it’s easier to go into larger cup sizes even if you’re not that big.”

“I’m glad you know so much about this,” I commented, relieved that she did.

Cassie chuckled, “I should. I model. I was working in one of those lingerie shops at the mall and when a corporate team did a site visit, their product promotion guy, some VP, told me to talk to their photographer and see if I was interested. The money’s good. Anyway, let’s get you dressed to go out, as adorable as you look right now.” Sifting through the pile on the bed, she pulled out a couple tiny wisps on fabric. “I don’t know if you prefer briefs, I have always been a thong girl. Let’s see how they work for you.”

I nervously took off the baggy shorts that thankfully were drawstring I had been wearing, and apparently those were holding up the boxers underneath. When I did, I discovered my inner thighs were soaking wet.

“Oh my,” Cassie gasped. “Well, nothing a washcloth won’t fix.” She popped out of the room and came back with a wet washcloth. I thought she was going to hand it to me, but instead she knelt before me, and started gently wiping upwards from me knees. Watching her help me was so sexy, looking down on her bare breasts. She nudged me legs a little, and I shifted my feet to spread my legs apart. As the soft cloth rubbed along my inner thighs, I felt my breath getting heavier and I closed my eyes. My eyes popped back open in shock as I felt a tongue run along my outer lips. I looked down and she was grinning up at me. “We can explore the more later if you want - you’re as sweet as I imagined - but your Aunt is expecting us,” she sigh wistfully. With a few playful but effective swipes, she had me tidied up.

Standing up, Cassie handed me one of the thongs she had been holding, then quickly put her bra and shirt back on. I clumsily stepped into the tiny underwear, and after sliding it into place, gave a couple experimental flexes of my legs. “I know, feels like a wedgie at first, but it gets easier. Let’s start you with something easy. Here,” she said, handing me a couple of things, “try this skirt and shirt.”

The black skirt was a soft thick fabric with an elastic waist, so I was able to sort it out easily for which I was relieved, as I wasn’t sure I’d be able to explain being unfamiliar with women’s clothing. The deep blue shirt fit nicely, although it felt weird having such a low neck. I looked down and could see the top of my breasts and looked back up, uncertain if it was too low cut. Cassie smiled, declaring “perfect!”, and steered me in front of a full length mirror on her open closet door. I had to admit, I did look really cute.

“Okay, and just in case you get cold from the A/C at the restaurant,” she added, sifting through the closet, coming back out with a small sweater on a hangar, and handing it to me. “You probably won’t need it, so just carry it for now.”

I looked at the slippers I had been wearing when she pulled me out of the house. “Hrm,” she bit her lip a little while thinking, which was adorable. “Ok, I might have some summer flats from a couple years ago.” After a couple minutes of digging in the back of her deep closet, I heard an “aha!”, then she came out and handed me a pair of slim shoes. Being used to bulky men’s sneakers, it was weird to slip on something that was just a tiny sole and a canvas fabric top. She was watching me, and at my concerned expression, asked, “do they fit?”

I flexed and tried a couple of steps across the room and back. “Seems like. I just usually wear bulkier sneakers, so it feels strange.”

Laughing, she replied, “we’ll have to get Sarah to spring for some sandals for you. With summer coming, you’ll love open top.”

With one more top to bottom appraising look, Cassie declared, “and you’re set! Let’s boogie, I’m starving.”

She bounded out of the room and I followed. When we got back to my house, Mom was in the kitchen. Hearing us enter, she turned. Looking at me, she gasped and teared up. “I, uh, I’ll go get ready to head out,” she said, passing us.

After Mom fled the room, Cassie remarked, “that was weird. Maybe go check on her?”

I nodded, went to Mom’s room, and knocked on the ajar door before I entered.

“Mom, are you ok?” I asked as I walked through. I was immediately grabbed into a tight hug.

“Yeah,” Mom answered sniffling. “When I saw you and the clothes and all girly, it just brought back all the times I wanted a girl. But--” she interjected “-- don’t think that means I love you any less when you’re a boy!” Not knowing what to say, I just nodded.

Mom let me go and fished a tissue out of a box on her dresser. “Now, let’s get Cassie and then lunch.”

“I told her that my mom died when I was little and that is why I’m here, so you can help with normal girl growing up stuff as my Aunt,” I blurted out, to help keep our stories straight.

Mom considered, and nodded. “Ok, right. Anything else I should know?”

I blushed and shook my head. She cocked an eyebrow at me, but said nothing. After a second, she added, “ok”, and left the room. I followed along.

The afternoon was a whirlwind of activity, as Mom wanted to buy me all sorts of new clothes - lots of casual wear, some night clothes, tons of underthings, even a few nicer items. When Cassie had gone to the bathroom, I asked Mom if she really wanted to buy all this if I was only temporarily a girl. She smiled and just answered, “never hurts to be prepared”.

After we dragged the haul home, Cassie bade us farewell and suggesting I come over later for a little party she was having. Mom and I wrestled one of the guest room dressers into my room to hold my new clothes. She hugged me one more time, then went to go have a nap.

I stood alone in my room, unsure what I should do next, so I looked at the mirror on the back of my door again. I was still wearing Cassie’s clothes. Pulling the shirt up to my nose, I inhaled deeply, smelling her on them. I felt myself getting aroused, which was still such a strange feeling. My erections always felt like a pounding war drum, the blood racing to my member like an army charging, full of need and vigor. This felt more like a growing heat, like watching a sunrise in a time lapse movie, and while there was a hunger, it didn’t feel like I had to take action to do something about it. I very much wanted to, though.

Before doing anything else, I started to put away all the clothes from today, mountains of bags rustling. When I pulled one dress Cassie had bought me out of its bag, something thunked back into the bag. I reached in, and laughed as I pulled out the box for a smallish vibrator. She had taped the receipt to the box and wrote on it, “mustn’t neglect the basics!”.

I just sat on my bed laughing for a minute as I unboxed it. Thankfully it took the same batteries as my game controllers, so I had spares about, and popped them in. When I hit the button, a very quiet hum started and it purred in my hand. I clicked it off again and put it in the bed, forcing myself to finish putting my new clothes away. As I did, my mind whirled thinking back to all the ways I wished I could masturbate before. One came to mind and shot a pulse of pleasure up my spine, weakening my knees, and I could not resist trying it.

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