Sister's Step-In

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Boy's twin asks him to help her in an odd way.
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PickleBoi
PickleBoi
54 Followers

I always hated my sister, Mekayla.

She always received the most attention from my mother in college. She was always getting the newest fashions and accessories from mom - and I, her twin brother, had to buy off the sale racks. I always ended up doing all of her chores, too. This always happened, and it made me angrier and angrier until I finally cracked.

One day, when I was vacuuming her room, I found one of her newest outfits laid out on her bed: a navy blue top, pleated short skirt, sky blue tights and matching pumps. As I seethed with more frustration, a strange idea popped into my head about wearing her clothes. I quickly shoved it out of my head, disgusted with myself for thinking of it. But then as I was cleaning, I got to thinking of mom and how she always seemed to treat women a lot better than men. Maybe wearing the clothes would help with that. So I quickly finished the chores, stripped my clothes, and slipped into Mekayla's. The feeling of the silky tights and the soft fabric of the blouse and skirt against my bare skin sent feelings of pleasure coursing through my body. Looking in the mirror after putting on the pumps pushed me over the edge as I saw how sexy my round ass looked jutting out like that. My hard-on was threatening to stain the clothes, so I quickly released it from the tights and jerked myself off with more fervor than ever before. I spewed what seemed to be gallons of my spunk into my hands, which I then licked off with my tongue. I quickly cleaned up before my sister and mom returned from one of their shopping sprees.

This continued for some time, the outfits always changing, making the experiences even better. But one day I got caught.

Apparently, Mekayla had suspected me of trying on her clothes, so she set up a hidden webcam to record the room while she was gone. And, sure enough, she caught me in the act. I dressed up in a little black dress of hers, opaque gray pantyhose, and her Mary Jane heels. But she didn't even need the webcam; she and mom walked in on me as I was jerking off. Right as I climaxed, I saw them in the mirror, both with mouths agape. Then my sister started laughing her head off. I looked down at my dwindling erection in shame. My mom was sure to just kick me out now.

But instead she just said. "This... is... Perfect!"

My sister just stared at my mom. "What?" She and I said simultaneously. "You can't be serious. Your son has turned into a perv, and you call this perfect?"

"Yes! You were just complaining to me how stupid it was that you couldn't go to the biggest party of the season because of your huge college test! Look at Mike here: he looks almost exactly like you in those clothes. He can take the test for you, and you can go to the party!" It was sad, but true; I had nearly no muscles to speak of, and I was always teased for the fact of my lack of height and my femininity.

Mekayla looked at me, pondering mother's words. Then her eyes lit up as she realized that I really DID look a lot like her. "Oh my God," she said, "It's true! It's like we're identical twins!"

"Wait, no!" I objected. "You can't make me do this!"

"Of course we can," My sister said with a wicked, sexy grin. "I've got that entire stunt of yours on webcam, and if you don't go to college as me, that video will. Your choice."

I gulped. It really wasn't worth it to be embarrassed by a video like that.

"Don't worry about it," Mom said. "We'll tell your college that you are sick with the flu for a week, and we can use that time to prepare you for your debut. I'll take you out shopping, get your hair done... Everything we need to do to make you look genuine."

That did it for me. My mom was finally going to pay more attention to me. I believed anything was worth that chance. "Alright," I said, "I'll do it."

"Excellent! I'll go to the store and get you some starting clothes to wear. Mekayla, you help him in hair removal and... some other things." She winked as she said this and left to do her shopping.

Mekayla did not look happy about this. But the chance of being able to attend the party allowed her to keep her composure. "Okay, if this is going to be successful, you need to do what I tell you to do, exactly how I tell you. Got it?" I nodded. "Okay then. Take off your -- I mean my -- clothes and get in the bathroom."

I returned the lingerie to her room and stood in the bathroom, waiting for my sister. I heard her rummaging around for something, and she finally came in with a can of hair removal spray. "Use this like it says on the back," she said. "I'll be back in a minute."

I hopped in the shower after the water had heated up. It said to apply liberally to desired area. I figured that meant everywhere but my head. I applied the spray and rubbed it into my skin. Soon after, Mekayla opened the door and entered into the tub... naked. I cringed; I never had seen my sister naked before. She had sweet nipples that just begged to be touched. They were very perky and gave her a nice hourglass figure. No wonder she was the hottie in college.

"Don't blush, I'm just your sister," she said, scoffing at my face. I only became more embarrassed. She had a razor in her hand, and she started removing the hair on my arms and legs. She then moved on to my ass and cock. I softly moaned as the sensations caused my dick to stir. Mekayla noticed this, and caused torment to me by teasing it with her touch. She even licked the tip of its pre-cum. She didn't go any further, though, and quickly finished the task at hand. I was hair-free in all areas except for my head. She quickly dried me off and inspected her work. "Yes, that will do quite nicely," she said. She then grabbed my cock and said, "Follow me." She had never acted like this before; it was like she wasn't my sister.

We entered into her room, where she disappeared into her huge closet and rummaged through. I stood there in my nakedness, anticipating what she had in mind. She returned holding a pink bra and panties, opaque white tights, and a white blouse with a pink miniskirt. She also had black curved toe pumps in hand. "Put these on, as sexily as you can." I was still surprised at how she was treating me. I did as I was told. I slowly pulled up the panties and tights, letting my tongue show to enhance the sight. The bra, blouse, skirt, and pumps came next. I made sure to let as much of my body show as possible during the process. After I was done, my sister reached into my bra and inserted silicone breasts. I suddenly could no longer see the tent in my skirt. It made the sensation even better having this new weight on my chest. She then turned her attention to the tent in my skirt. She pulled up the skirt and down the lingerie to find a cock straining to get even larger after being released. "My, it seems you like this more than you're letting on, brother... Or should I say SISTER now?" She giggled as she teased the tip with her fingers. It was true; the feel of the tights on my newly shaved legs was absolutely astounding. I wished I could have thought of it sooner. As I came closer to releasing my juices, she suddenly stopped and retrieved something from her drawers: a dildo.

My heart skipped a beat. "Oh, no. Oh nonono-"

"Oh, yes," She said with a quirky grin. "If you're going to be dressed as a woman, you're going to be treated as a woman. Now get on your hands and knees, slut!"

Now I was getting a little scared. So I did what I was told, for fear of repercussion. She lifted the skirt and pulled down the panties and tights far enough to show my virgin ass. She lubed up the dildo and pressed it firmly to my sphincter. At first it resisted, but then it gave in to the pressure. I moaned in both pain and pleasure as it reached places I never knew I had. Within a few minutes, my erection was at full blast, not hindered by the dress any longer. It soon let loose a constant stream of cum onto the floor. She pulled out the dildo, covered it in the cum, and ordered me to lick it off. I did as I was told. "Good girl," She said as I licked off what was left. She replaced the tights and panties over my now-pained ass and cleaned the dildo thoroughly. Mom finally arrived home and inspected Mekayla's handiwork. "Great job," she said, "but now it's time to make you transform even further."

She blindfolded me and had me sit in a chair. She applied some semi-permanent glue to the silicone breasts, makeup to my face, and a wig to my head. When I was released from the blindfold and looked into the mirror, I thought I was looking at my sister. She stood by me, and we looked exactly like identical twins.

"Oh wow... I can't... Oh wow..." My sister said in disbelief. She stared at the reflection for what seemed like hours. I couldn't believe it myself. I looked... beautiful.

For the next few days, I was assigned the task of mastering a voice that sounded like Mekayla's. Also, Mom had bought me a maid's outfit, complete with apron, black opaque tights, and three-inch Mary Janes that I was to wear around the house in order to get used to walking in heels. Mom and I went shopping several times to try out my new feminine self, and I wasn't surprised to see that I got lots of stares from the boys. I could only imagine what they were thinking as I swung my hips wearing a short jean skirt, nude pantyhose, and pumps. My Mom expressed her approval several times. Each time my heart soared, making me think even more that this bargain was definitely worth it.

Every day started out with a shower involving getting a thorough cleaning from Mekayla. And every day also included a session of dildo sucking or butt-plugging. I hate to admit it, but I loved being treated as a female slut would. That might have changed had I known why at the time.

On the last day, Mekayla woke me from my slumber with her usual morning orders. I hopped up and headed for the shower. Mekayla walked in, looking slightly sheepish as she carried in the special hair-removal soap. "Uh, Mike?" she said.

"Please, Mekayla, if I'm going to get used to this, you need to call me by your name." By now, the "Mekayla voice" had become a habit, and we sounded almost exactly alike.

"Sorry. Listen... Uh, I have something I need to tell you that I probably should have told you a long time ago."

"What's that?" I asked suspiciously.

"Uh... Well, the real reason I was using the dildo on you... Well, it's because I've... kinda been... "Servicing" this guy at college to get better grades, you might say. And the day you happen to be going to fill in for me... Was one of our appointments."

"Oh, you gotta be fu-"

"Please, don't have an outburst. Look, I know this has been hard enough on you already, and I'm really, really sorry that this has to happen. It's just that if you don't, then he'll do something that will keep me from graduation. Please, I really need you to do this. Sister to sister."

That took me back. This was the first time that Mekayla had actually acknowledged my transformation. How could I respond to this?

Before I could think, my mouth blurted out, "Of course I will." Mekayla squealed with joy as she rushed in to hug me. "Oh, I must find a way to repay you," She said.

I said nothing, but returned her embrace. We entered the shower and did our usual routine. It was losing its novelty, so my cock only twitched at Mekayla's touch. She already had my outfit for the day laid out: a dark blue minidress, light blue stockings, and navy blue flats. I was grateful for the break from high heels. She pulled out the dildo once more after I had gotten dressed and had my makeup applied, only this time it had a strap-on. "I want to make it as realistic as possible this time," She said as he put it on. She turned on the vibrator and offered it to my mouth. I accepted willingly, sucking every inch out of the half foot. I had become quite professional in the art, and it didn't take long for my erection to start staining the panties, and I quickly pulled them down to prevent further stain. I moaned around the cock as I imagined it was the cock of the teacher at college that I was to suck off just the next day. But before I could release my load, she pulled out and moved to my still tight ass. She quickly inserted the vibrator, and my prostate quickly received transmissions of pleasure as it was touched by the plastic. I was near to cumming, but before I could, she pulled out yet again. Aww, now what? I thought. She removed the dildo and told me to stand up. I did so while she kneeled down in front of me. "I think I know how to repay you," she said as she grasped my erection in her soft hand.

She licked the tip of my pre-cum, generating an instant response. "Wha... uhhh..." I tried to ask what she was doing and how morally wrong this was, but it just felt so good as her tongue glided up the length of my erection. She gave me pleasure like I had never felt before. Then she let go of my cock, got on all fours, and pulled her own dress up, revealing her beautiful hips and cheeks. She offered her hole to me. Without conscious effort, I glided to where she was and inserted my she-cock into her awaiting hole. Our feminine grunts and gasps filled the air as I pounded her ass with all my might. I exploded into her hole, spewing so much cum into her that she began to leak. She dutifully licked up what had dripped and licked off my erection. She then stood and shared my cum with me through a deep, lesbian-like kiss. I had never felt this way towards my sister before -- it felt so wrong. But she had shown love to me in a way I never thought possible before.

Maybe that is how real sisters feel, too.

PickleBoi
PickleBoi
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5 Comments
AnonymousAnonymousalmost 3 years ago

too short of a story.

AnonymousAnonymousabout 6 years ago
More

OMG, I love the cute outfits he gets to wear. I know this story was posted several years ago, but I wish there was a sequel where he is taken by a big stud while dressed in a cute outfit. I would love to wear opaque tights with high heel Mary Janes and be used over and o ver by a couple of well-hung men while being filmed and my spit-roasting live streamed to the world.

AnonymousAnonymousalmost 9 years ago
Great Story

Would like to see chapter 2, 3, 4, and 5, etc... .

AnonymousAnonymousover 12 years ago
Beautiful!

What a beautiful story - two sisters. Will you continue this one?

GagelessGagelessalmost 15 years ago
Excellent start

You've got the makings of a good series here. I wanna see what other misadventures they get into. How far will she push him? How many other things will he be forced to "step-in" for?

Keep writing.

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