Sara in Autumn Pt. 01

Call me Sara. That's part of who I am. Maybe I'll write about other parts of me some other time, but the muse demands Sara.

One fine fall day, my friend Laura called me and asked if I could babysit her kids. I didn't really have a reason to say no, and I normally had fun with them. Besides, I don't know if I could how many favors I owed her. I threw on my jeans and a T-shirt, and headed over.

Laura greeted me with a smile. She looked amazing, and I did not hesitate in telling her so. The five inch heels she was wearing meant I did not have to bend over nearly so far to hug her tight. Her tight black dress showed off some deep cleavage. Her normal bohemian mess of hair was curled and sprayed, and the glitter of her eye shadow brought out the sparkle in her eyes.

"You look amazing. You sure you need to go out on this date? We could always stay in and wait for the kids to fall asleep..." Laura had always been a true friend, we flirted like mad, but never took that step.

"Yeah, you wish. Keep it in your pants. I don't need the kids asking why the babysitter had an erection." I blushed a little, and laughed.

"Don't let them stay up too late, ok? And don't wait up. If this goes the way I hope, I can tell you about it over breakfast."

"Yeah, yeah. Get out of here before I drag you to a dark corner. Have fun..."

Honestly, her kids were fine. A bribe of ice cream ended the tears and got the vegetables eaten. By ten, they were actually asleep. I tiptoed up to Laura's room; I figured the TV in there wouldn't wake them, and I'd have a peaceful evening.

Laura's room looked like a bomb had gone off. Her clothes were everywhere; she had apparently changed her mind what to wear a dozen times tonight. Bras, panties, pantyhose, everything was out, and all of her make up was cluttered around in front of her mirror. I pushed a few things out of my way and looked for something worth watching. I surfed channels, and found RuPaul's Drag Race.

I watched, changed the station, and kept coming back to it. It had always appealed to me, but I was always afraid of trying it. I'd be laughed at, I'd look horrible. But surrounded by women's clothing, a little bored, a lot horny, and expecting quite a bit of time before Laura got home, I thought to myself, "why not?" I could always clean up as sort of a payment for this intrusion.

I started off by stripped down, and hopping in the shower. Laura's soap smelled pretty, and so did her shampoo. I laughed, and grabbed her razor. I started with the five o'clock shadow, but didn't stop there. I had to change blades midway through, but soon my legs were hairless and silky smooth.

After drying off, I slid on a pair of thigh highs. They felt wonderful as I ran my fingers up and down the smooth fabric. I tried on three different styles of panties before I realized there was no way they would fit me. Then I found a little lace g-string in the bottom of a drawer. Ok, so it was instant wedgy, and I was so hard that I poked straight out the top, but I had them on.

I was finding this whole process entirely erotic in ways I hadn't anticipated. Still, I didn't want to masturbate just yet. I was determined to finish getting dressed. What was a knee length skirt of Laura came down to my mid thighs. I started trying on bras, but they were too narrow. I couldn't get them to hook. Then I had a flash of inspiration, and a few bent paper clips later, and I had space for D cups. I contemplated stuffing, and a quick Google had me filling spare pantyhose with uncooked rice. That filled the bra out nicely, and I was able to stretch a knit sweater over them. It was a little short, showing off my midriff, and a little bit of my upper arms, but it was the closest to fitting thing I could find.

I watched a few YouTube tutorials, and started applying make up. My hormones made my hand shake a little, but I was able to get concealer, foundation, eyeshadow, blush, lipstick and mascara down. I was too nervous to try eyeliner.

One more trip into Laura's closet yielded a collection of wigs from her theater days. Soon long dark tresses cascaded down my neck, and the look was complete. I looked at myself in the full length mirror. I ran my fingers over my thighs. I laughed, and traced my erection through the skirt. All the hormones flooded my system. I could not control myself. I freed my cock from it's lace prison, and began stroking it, watching myself in the mirror. My mind raced as I rolled my finger over the top of my shaft, gather the drop of precum that had gathered. I watched myself suck it off my finger, a light ring of lipstick left of my skin. I wanted to suck cock, badly. And I wanted this woman in the mirror to suck me off. Under Laura's bed, I found her vibrator. Without hesitation, I began to suck on it, my hand stroking me fast. I made myself watch as I gave the toy head, and I felt my orgasm building. I caught my load in my hand, and licked it all clean.

I sat on Laura's bed, panting, squeezing the last precious drops from my cock before tucking it back away. WIth weak knees, I stood up and began cleaning. I loved the feel of my fake breasts pulling down as I folded and put away all the clothes and put the caps back on all the make up.

Suddenly, I heard Laura's voice call out. I looked over at the clock. How was it 4 AM already? Her footsteps were on the stairs, and there was no way I could change before she got up here. I wondered if nude would be better than wearing her clothes, when she opened the door.

She looked at me, sitting on the edge of her bed, my ankles crossed and tucked back. "Please don't be mad. I can explain." I couldn't really, but it didn't matter. She silenced me with a finger.

"You need to ask before you can borrow my clothes. Look at you. That top is way too small. Take it off, right now." I complied, and she handed me a button down top. She tied it off at the midriff, and smiled in satisfaction "There, now you aren't stretching my clothes out. Did the kids behave?" I nodded mutely.

"Good. Now drive home. Just like that. Actually, wait a second." She touched up my make up, then snapped a picture with her phone. "Send me a selfie when you get home, or I post this one all over your Facebook. Understood?"

She handed me my wallet and keys. Then Laura grabbed a spare purse and handed it to me. "No pockets in that skirt. And here, keep the lipstick, in case you need to touch up." I was bright crimson, and glad for the dark of early morning as I walked to my car. At least she let me keep my shoes; though I'm guessing that's only because none of hers could possibly fit. A few blocks away, I pulled in to a gas station. No way was I getting stranded like this. It was mostly quiet, thank goodness.

Then I heard a cry of "Hey Baby" from the diner across the street. My eyes darted about, wondering who was being holler at. Then I flushed when I realized it was me. It was pre-dawn, from across the street. No big deal, I told myself. I ran in, got myself a cup of coffee, and got all kinds of flustered when the teen behind the counter asked me, "Is that all, ma'am?" I got out of there and home safely. I took a selfie and sent it to Laura.

"Good girl. Tomorrow evening, show up at this address at 5. And what's your name, sweetie?"

I gulped and texted back a single word, "Sara."

"Ok, Sara. And show up in your own clothes. Mine don't really fit."

I masturbated twice more before finally falling asleep.

Time after I woke dragged on forever. I told myself I wasn't going to go, and then could think of nothing else. Feminization videos, women's shoes, and gender bending porn filled my search bar until it was time to go. A gentle nudge of a text from Laura made my heart race. "I'd hate to have to press send on two pictures now."

I rang the bell of the house, and a gorgeous woman greeted me. She had long blond hair, and blue eyes that shone. Her ample cleavage was barely contained by her thin sundress. My heart pounded in my chest. "You must be Sara. Laura's told me all about you. My name is Autumn. And you are right on time, I like that. Come on in, would you like a drink?"

I followed her, my eyes drifting to her tight ass. "Why are you here, Sara?"

"Because if I didn't show up, Laura would send out pictures of me." I sipped at the ice tea.

"I don't think that's true, Sara."

"What do you mean?"

"Sara, honey, you need to be honest with yourself, and with me. You didn't have to let her take that pic. You could have washed your face. No, you're here because you want to be. You want to be free."

I swallowed my tea. "I don't know, Autumn. Maybe. Maybe I shouldn't be here. This is all too much."

"You enjoyed it last night. Apparently quite a bit. You probably should have watched the lipstick off the vibrator. Although she was glad there weren't other stains on it." My heart sank. Shit, I didn't think she knew about that part.

"I'm going to dress you up pretty. We'll take some pictures. I won't share them, they'll be for you. And after we're done, you tell me if you want to do this again, does that sound fair?"

"Well, Autumn, I've never been one to turn down a reasonable request from a beautiful woman. But I can walk away from this tonight, if I want?"

"Of course, if you want. But I don't think you'll want to. Ok, first step, I need you to strip. We're going to wax and shave you totally smooth."

She escorted me to her bedroom, and I began to get naked. I hesitated for a moment, but she yanked my underwear down past my engorging erection. I covered it shyly.

"I've seen plenty of those. Don't worry. And yours is just fine." I was beet red and tock hard as she made me lay down. She largely ignored my erection as she began to spread wax on my chest, stomach, and arms. I braced myself for pain, but the yank wasn't nearly as bad as I thought. Autumn was relentless, though, as strip after strip revealed smooth skin underneath. I rolled over, and she began anew on my back and my ass.

"There, first step, Sara. Now, I'm going to glue on these silicone breasts. If you have a reaction, we'll try another method, but this will give you a great look that isn't just static. They'll move with you. How big did you want?"

I blushed, and looked at the breast forms she had before me. I selected a pair of C's. Part of me wanted to tell her the biggest size she had, but I shouted that down. She smiled at me as she glued them on.

"Ok, panties. You'll need a pair on next. Unless you like me looking at your cock." I blushed, and she leaned in close. I sprung up to full attention. "We'll never get you tucked being that hard." Her fingers grazed me, and I moaned. "Should I take care of that for you?" I gasped and she kissed me lightly. Her lips tasted so sweet, and her hands pumped me up and down. I lay back, as she pushed gently on my chest. She spread my legs, and I felt a single finger penetrate my ass. I cried out, and her soft, warm mouth enveloped my cock. Her finger probed deeper as she bobbed up and down my shaft. I could not stop myself, and launched my load into her mouth. She milked every drop, then came up and kissed me deep. My mouth opened for her tongue, and I felt my warm salty load in my mouth. It was so erotic, even as I swallowed it.

"That was nice, Sara. But I promised to get you dressed, so I need to do that before I just fuck you into oblivion." She gave me a tight pair of body shaping panties that held my now soft cock against me. Then she dressed me in thigh highs, a black lacy bra, and a short black dress. Then she clipped some earrings on me. The long silver dangles looked so pretty in the mirror. Then she added a black lace choker, and moved on to my face. "Now, pay attention, I won't be able to do this for you every time you want to feel pretty." I nodded, and tried to listen as she contoured my cheeks, and applied layers of make up and painted my nails. Finally, she clipped a wig to my hair, and I looked in the mirror. "What do you think, Sara?"

"Oh my god. I'm so pretty. I look...sexy."

"You know it, girl."

She had me pose for a few pictures.

"It would be a shame to waste all that work. Why don't we go out?"

She smiled at me, and kissed me lightly. "Lay on, MacDuff."

She handed me a pair of pumps, and a purse that matched the dress.

We drove to a club where the music was blaring, and there was a line a block long. Autumn dragged me up to the bouncer, whispered in his ear, and we got to cut, without paying a cover charge.

Inside it was all but impossible to hear the person next to you. We found a table and Autumn ordered us drinks. We sat just people watching as I drank, delicately, trying to mimic Autumn's mannerisms. Another round appeared, and the waitress pointed to the gentlemen who had sent it. Autumn waived them over. She said something to one of them, and they disappeared onto the dance floor.

My heart pounded as Derek tried to chat me up. I pointed to my ear, and mouthed that it was too loud. So I wrote my number on a napkin in lipstick, and he began testing me. He was tall, at least 6' 3", and a shaved head. His skin was a gorgeous olive tone. We watched them dance, although I declined to join them on the floor. Derek texted me so many compliments, and I felt myself place my hand on his thigh. I hadn't done anything with a man since college, but Derek just looked yummy.

He leaned in and kissed me, and I felt his hand on my breast. Oh, I wanted him suddenly. I felt his cock press against me. He asked if I wanted to go back to his place. I texted back that I couldn't leave Autumn. Then I found myself undoing his pants. I took a napkin, and reached down his pants making sure he was still covered by the tablecloth, I began to stroke him. I kept looking at Autumn, who flashed me a dazzling smile, while jerking Derek off. I caught his load in the napkin, which I deftly stowed in my purse. Autumn dragged me to the bathroom. The women's bathroom.

In there, I quickly threw the napkin out. "Oh my god, Sara, you are embracing your inner slut tonight."

"I can't believe I did that. I'm not...you know..."

"A man crazed woman who just enjoyed the power of controlling a man by his penis? I think you might be."

I touched up my lipstick, and made sure to sit down while I peed. I don't think anyone noticed or cared.

"Do you want to get out of here? I have an idea."

"Autumn, I'd follow you anywhere." She laughed and kissed me lightly. "Then lets go. We'll touch your inner slut and see where we end up.." She grabbed my ass and pulled me close. "Just make sure you save some for me."