Serving My Sister II: Shopping Spree

Note : This story is completely fictional!

When I went to bed that night, I was still pretty much in shock. My sister had let me know, on no uncertain terms, that I belonged to her. She was not exactly allowing me to forget it either. As I had been putting myself to bed, Eileen had snuck into my room, holding one of her pink mesh thongs, and a pastel-pink, satin, baby doll night gown. I was to sleep in them, but I was not to pleasure myself.

I had tossed and turned almost all night, trying so hard to fall asleep with the rock hardness caused by my sister's sleepwear. Needless to say, when I awoke in the morning, my cock was still wide awake. I figured it would be better if I didn't get dressed just yet, but rather went straight to my sister and found out my instructions for the day. When I exited my room (still full aroused), there was Eileen waiting for me. She was dressed in a look-of-leather mini skirt, extremely transparent pantyhose, black knee-level boots with wide, three-inch heels, and a royal blue spaghetti strap tank top.

"Good morning, Jeremy," said Eileen, her voice sounding like 'business as usual'.

"Good morning, mistress Eileen," I replied, my head dipped low, my eyes gazing at her feet.

Eileen put her fingers under my chin and lifted my head. "It's okay, you can look at me." Then she looked down on my dick, finding it poking out the bottom of the baby-doll gown. She also found the vast spot of pre-cum. "You fucking bitch!" she exclaimed, taking a firm hold of my penis. "Look at the mess you've made! Look!"

I did as I was told, staring straight down at myself. Eileen gave my cock a squeeze near the head, pushing out some more pre-cum. A moan threatened to escape my lips, though I couldn't tell you if it was from fear or pleasure. I did my best to muffle it, but Eileen heard my whispering sound, looking up at me as she did.

"Hey!" she scolded, bringing my attention back to her. "Did I tell you that you could get horny?"

"No, Mistress Eileen," I answered, my voice trembling with sudden fear.

Eileen let go of me, then slapped me hard across the face. "I don't ever wanna see you getting hard without my permission, do you understand me?"

"Yes, Mistress Eileen."

"Good." Eileen took my hand and led me to my parents' room once again. "Now seeing as how you fit pretty well in mother's clothes, that's what you'll have to wear today."

My mother's clothes did indeed fit me well. After all, I was quite small for a man, as if I had stopped growing (in overall size) at the age of fifteen. Hell, my dress size was six for crying out loud! Chalk that up to an extremely high metabolism. Anywho, my sister picked out some pretty casual clothes, yet not so casual as to let me forget I was cross dressed. Taken out of my sister's thong, I was slipped back into the same cum-filled panties I had worn the day before. They still smelled of my cum, which turned me on for some reason I could not explain. I wore the same bra as well. Instead of a skirt, Eileen dressed me in a pair of Mom's hip-hugger jeans, and threw a tight, middrif t-shirt on me. Finally, to top if off, I slipped my bare feet into a pair of silver sandal-heels.

"Remember, no getting hard without my permission," Eileen reminded me. That was the most difficult thing in the world at that moment. However, I gave it my best, thinking of things I did not find attractive. It worked.

Fully dressed, Eileen led me into the garage. She told me to get in the car, but I hesistated. I was barely ready to be in my sister's service, let alone go out in public all dressed up. At my hesistation, Eileen approached me, grabbed me by the cock, and dragging me to the passenger side of her Dodge Neon. "Never make me tell you things twice! You want me to out you to mom and dad?"

I shook my head and quickly got in the car.

Eileen told me not to worry as she drove off. I was too afraid to ask where we were going, so I tried to relax, knowing I'd find out soon enough anyway. Fortunately for me, she took me to a place far enough away from anywhere or anyone I knew; as it was, the drive took 45 minutes one way. The place was a clothing store, big surprise there. The store was small, the lot was nearly empty, and Eileen parked as close to the front door as she could. Cutting off the engine, she turned to me.

"Start rubbing yourself," she instructed. "I want you hard, but not satisfied. Got it?"

"Yes, Mistress Eileen," I replied, my voice still shaky. I closed my eyes and began rubbing my hand firmy against my crotch, over the jeans. It didn't take my cock long to start stiffening up, and I could feel fresh pre-cum staining the panties again. When my erection was far too hard for these tight jeans to conceal, my sister stepped out of the car, saying to me, "Let's go."

Inside the store, she led me straight to the women's section. She filled our shopping cart with just about everything the place had: tight jeans, middrif shirt, skirts of all kinds, lingerie, evening gowns, blouses, even various women's shoes in my sizes. In the dressing room, I was to try on everything, just to make sure it all fit perfectly. Furthing my humiliation, I was to exit the dressing room wearing each item, find where the hell my sister had went off to in the store, and show her how I looked; and every time, there was no avoiding passing at least one other customer.

When she was satisfied I had enough women's clothes, we finally went to the checkout lane and made our purchase, via Eileen's credit card. "Miss," she said to the woman working the cash register, in such a sweet tone of voice, "can these items be worn from the store?"

"Oh sure," said the employee. "Feel free to avail yourself to the dressing rooms in the back."

With that, Eileen smiled at me, taking us back there once more. This time, however, she entered the dressing room with me. From my mother's clothes, I changed into a tight, neon pink mini dress. It was sleeveless, low-cut in the front, and had a 22-inch zipper in the back. On my feet were matching three-inch pumps, and my legs were covered by thick, tan pantyhose. With this, I wore no underwear.

"Cum for me," Eileen instructed.

"Mistress, please," I begged, and she knew what I was getting at.

"We'll never be back in this store again. Now cum!"

Without further arguement, I lifted my new dress, grabbed my dripping hard on, and stroked. I stroked fast, wanting to end this as quickly as possible, all the while gazing at Eileen's alluring body. This did not go unnoticed. "You want me, don't you, Jeremy?" Eileen asked me. I did not answer, because I didn't know how. Yes, I wanted her, but I surely wasn't ready to admit that. Nonetheless, I was forced to do so. "Say it!" Eileen said forcefully, though keeping her voice down.

"I want you, Mistress Eileen," I obeyed. It made me feel ever more horny to hear myself declare that I wanted my own sister.

"You haven't earned me yet," she told me with a teasing smile. At those words, I unleashed my load. The first few squirts actually hit the wall of the small dressing room, before the final bits landed on the floor. "Good little servant," Eileen whispered, stroking my face with one finger. "Now, kneel in that--" she gestured to my cum on the floor, "--and lick that." She gestured to my cum on the wall. "Don't swallow."

"Yes, Mistress Eileen." Doing as I was told, I knelt down, making sure one knee was directly on top of my still-warm cum. Then I leaned forward, slowly licking my cum off the wall. I still disdained its taste, but I knew I was to finish all of it. When I did, Eileen stood me to my feet and instructed me to show her. I opened my mouth, showing my sister my cum-filled mouth.

"Okay," she finally said. "You can swallow." I wasted no time. "Let's go home, you filthy worm."