Exactly What It Looks Like
Introduction:
A boy in girl’s clothing…
“No, sis, I’m fine,” I replied, wanting to get her out the door as quickly as possible.
“Alright, I’ll be back later,” and with that, her auburn locks disappeared out the door.
I listened closely for her to leave, car door slams, engine starts, and then off she goes. Finally, it was time. I had been waiting for what seemed like an eternity to fulfill my fantasy, to walk around in girls’ clothes. I loved the feel, I loved how my slim body looked in them, and now that my sister and I are living together without my parents, I had been waiting for a chance to put on some of her things and hang around the apartment.
I had these feelings before, but I suppressed them for fear my parents would find out, and I moved out of their house as soon as I turned eighteen to get away from the temptation. I moved all the way from Richmond, Virginia to Seattle, Washington. I lived a normal life for a while, and managed to push my feelings further down. Three years later, my sister started at the University of Washington and moved in with me, bringing us to now, where I was just seconds away from her door.
I swung the door open, barely able to contain my excitement, and then made a dash for her dresser. I slid open the drawer where I had seen her put some panties when I first helped her move in, and all the sudden I was engulfed in a sea of panties. All the different styles, colors, and textures, I was in heaven. This was my first excursion into female clothing. I hadn’t even seen girls naked or taking off their clothes before, other than on the Internet. I had many female friends, but no matter how hard I tried, I had never managed to get a girlfriend or even a fuck buddy.
I stripped off all my clothes and then tossed them in a corner and pretended that I was a girl trying to choose what to wear for the day. I searched through the glorious delicates this drawer hid within and found a lacy white thong with a cute little red bow on the front that I pulled out and slipped on. I tucked my moderately sized cock between my legs in order to hide any bulge, and pulled up the panties and let the fabric rest between my ass cheeks, a near perfect fit, though a but loose as Erin had rounded, womanly hips that were wider than my own. The feel was incredible, and I was becoming more and more excited by the minute.
Next thing to find, a matching bra. I yanked open the drawer that contained my sister’s bras and began to search through them. After a few minutes, I found a match, a lacy white bra with a little red bow between the C cups. I slid my arms through the holes and pressed the bra against my chest. I had a little trouble fastening the hooks, but after struggling with them for a few minutes, I managed to secure the garment in place. I took a moment to admire myself in the mirror and my deep blue eyes filled with wonder. The thong was cute and made my ass look incredible, and the matching bra just completed the package. Time to move on to the next step, finding clothes.
I opened the closet and grabbed a short plaid skirt and a white cami. I slid the skirt up just above the top of the thong, and then zipped it. The skirt stopped just below the top of my thighs, about an inch and a half below my ass. It made me feel so sexy wearing the skirt, knowing that any wrong move could give a peek at my panties. I slid the cami over my sandy blonde hair and started admiring it all together. I put on a wide black belt around the top of my skirt to complete the outfit and then admired myself every which way.
I was bent over slightly trying to see if my ass would pop out of the skirt when I heard the door to the apartment creek open and slam shut. I stood, frozen in fear, hoping it was a burglar, or that my sister had just forgotten something and was on her way back out. I tried to think of what to do next, but it was too late.
“Some jackass took my space,” Erin vented, “I’m gonna set this stuff down in my room and then could you help me get the rest of my stuff… Clay?” She had just walked into the room, and seen me bent over, in her clothes her sky blue eyes catching me like a deer in the headlights. She looked betrayed, confused and shocked.
She seemed to be at a loss for words so I took the initiative and piped up, “Erin, this isn’t what it looks like.” I said, trying to reassure myself of the truth in this statement.
“Really!? Because it looks a whole lot like you in my skirt and top, and at least my bra!” She shouted.
“Okay, it’s exactly what it looks like,” I said shamefully, “Let me explain sis.”
Her head bent slightly to look up the skirt that barely covered me. “Oh my God! You’re wearing my thong to you sick perv!” She yelled in disgust, “Just wait till everyone hears about this!”
This little 5’8”, red-headed ball of fire seemed to tower over all 6 feet of me with this statement. “Wait sis, please don’t do this, I’ll do anything.” I pleaded.
She paused in the doorway and turned around. “Anything?” her face contorted into a wickedly sexy smile, and she walked towards me. “Alright,” she started, “You are now my bitch. For starters, you are going to pay my half of the rent. Also, we are switching rooms. You will now be staying in this room, and I will be taking yours.”
I could do nothing but accept. “Alright, let me go get my things.” I said softly.
“No need,” she said, “Your things are now right here. Anytime that you are at home, either alone or with just me, you are to be wearing my clothes, and I will be wearing yours. You are to keep your whole body shaven at all times, and you will always be expected to have a bra and panties on, even in public. Now, go get started with the shaving, make sure to get your cock as well, or else I’m setting you up with a waxing appointment. We’ll go over the rest of the rules when I get back, I have some things to pick up.” She started to walk out her bedroom, well now my bedroom, door. “Oh, and don’t forget to use your girlie soaps, shampoos, and deodorant, and remember to put on some heels and stockings when you’re done.” And with that, she walked out of the apartment door saying, “Mmmm, you do look sexy in that skirt.”
I continued to go over in my head what had just happened. I tried to think of something, anything that could get me out of this, but I was stuck, I was now my sister’s bitch. I walked to the bathroom still thinking and ran the shower. I shaved my whole body, and then washed off with my sister’s soaps and shampoos. I had to admit, I was starting to get turned on by this, and it was showing. I turned off the shower and before I could get myself off, there was a knock on the door.
“Hurry up and get your tight ass out here, we have things to do.” Came Erin’s voice through the bathroom door.
I wrapped a towel around my waist and stepped out of the bathroom.
“Nope,” Erin reprimanded, “That’s not how a good little bitch wears a towel.” She pulled the towel up to my chest and fastened it there. “Now, go get ready and then meet me in the bathroom.”
I went to my room and put on the same thong, skirt, bra, and cami I was wearing before. I saw a pair of white stockings and black CFM heels sitting on my bed. I slid the stockings up my now hairless legs and strapped the heels around my ankles. I started to head for the door but the heels were damn near impossible to walk in. After a few minutes, I got the walking down well enough to stagger to the bathroom.
I opened the bathroom door and was greeted by a bright flash. After the spots cleared from my eyes, I saw Erin standing there holding a camera, however, there was something odd about her, she was wearing my clothes, pants sagged down and boxers showing. There also seemed to be a large bulge in the front of her jeans. “What a good little slut you are.” She mock praised. “Here, this is to be worn anytime you are at the apartment without another person.” She tossed me a wig of long, curly, strawberry blonde hair. “Put it on and then you get to learn how to do your makeup for me.”
I couldn’t take anymore, this was too much. “Erin, I can’t do this anymore.” I said quietly.
“What was that?” She asked mockingly. “Because it sounded to me like you said you want me to put this pic of you on Facebook. Is that what you said?”
“No…” I squeaked, and then begrudgingly put on the wig and walked over to my sister.
“Good.” She said, and she began to put on my makeup, teaching me how to do it myself, while giving me more ground rules. “When it is just the two of us in conversation, you will refer to me as Eric, and I will refer to you as Chloe. Your ‘time of the month’ starts the 15th and lasts till the 20th, this way it’s easier for your stupid slut brain to understand when you should have one of these in.” She pulled a box of tampons out of the cupboard.
“In where?” I asked, afraid of what the answer would be.
“Take a guess you dumb bitch.” She retorted mockingly, “In case you didn’t guess,” she paused and moved towards me, “It’s the hole you’ve got covered by this cute thong.” She slapped my ass and then said, “Come on Chloe, time to go over the last of your responsibilities.” And she walked out the door and towards her bedroom.
“Be sure to have a meal ready for me when I get home.” She said as we walked to her bedroom. We stepped through the bedroom door and she said, “You are not allowed to cum unless I tell you to. Now, on your knees.” I obediently got down on my knees, beginning to grow more turned on than frightened or embarrassed by the situation. “Good girl. Now pull down my pants and boxers, I have a surprise for you.” She giggled through that wicked sexy smile.
I pulled down her pants and her boxers and out sprung a nine inch strap-on. “You like it?” She asked grinning at me. The truth was I was kind of liking the whole idea of this. I felt my cock getting harder and harder in my panties. I nodded. “Good,” she said, “You will be using your mouth and ass to please me every night, except for the nights you’re on your ‘period,’ then you will only use your mouth to please me. Got it?” She quizzed. I understood and I was getting more and more turned on by the whole scenario. I nodded. “Good slut, and if you do really well, I may give you a special treat.” She smiled, somewhat softly this time. “Now let’s get started with tonight’s fun.” She said before bending down to give me a deep passionate kiss. She then pulled away, stood up straight, removed her baggy t-shirt, revealing her perfect C cup breasts topped with her perky pink nipples, and then presented her cock for me to suck. “Get to it.” She said.
I was dizzy with anticipation at this point and didn’t waste a moment before licking the cock in front of me. My tongue slid up and down the shaft, stopping to tickle the head with my tongue before I began to take the plastic member into my mouth. I went down on it as far as I could before pulling off, and then repeated to motion, growing in speed and depth each time.
“What a good little cock sucker you are!” Erin cheered as she placed her hand on the back of my head and moved my head up and down at a steady place. I kept going and was really starting to enjoy it. Occasionally, Erin would push my head all the way down and hold it there until I gagged before letting me come up. I had no idea why, but I was getting very turned on by this. Then all the sudden, she pulled me off the cock.
“Good job slut, but that’s enough of that for tonight. Now stand up.” She commanded. I eagerly obeyed. “Good girl, there may be hope for you yet, my little bitch.” She stepped over to me, kissed me again, this time her naked boobs pressing against me and her hard cock grinding between my legs only served to turn me on further. She pulled away, pulled off my cami, turned me and bent me over the bed. She then lifted my skirt and began to swat my ass hard. “This is for talking back to me in the bathroom instead of doing what I asked like a bad little bitch.” She continued to swat. Two. Three. Four. Five. My ass was turning bright red. However, even the pain only served to make me harder.
Then she stopped, and pulled down my thong. “Now you get a treat for being such a good little slut ever since.” Nothing happened for a while, and I was a little afraid to turn around. Then I felt a lubed finger start to touch my tight asshole. It started to slide inside, little by little, until she was finger fucking my asshole. “By the way, I brought the lube this time, but from now on, if you want it, I expect it to be applied and ready before I’m ready to fuck you.” Erin stated matter of factly. My insides were burning, my balls were on fire, my cock was harder than ever, and I wanted nothing more than for her to shove that cock in me. She continued to press her finger in and out, slowly but steadily. “Now what should I do, little Chloe?” Erin whispered in my ear.
“Fuck me please.” I whimpered quietly.
“What’s that?” Erin teased, “What do you want?”
“Fuck my ass, please.” I plead a little louder.
“I’m sorry, one more time, what do you want?” Erin teased, continuing to push her finger deep in my ass.
“Fuck my ass, Eric, please!” I shouted.
“Mmm, I love a slut that knows what she wants.” Said Erin as she pulled her finger out of my ass and shoved it in my mouth. I sucked her finger eagerly, licking everything off of it until she pulled away and lined up her cock with my asshole. She pressed at the entrance of my asshole, probing it with the head of the cock, trying to get it open wide enough to fit the whole thing inside. She kept pushing until, pop, the head slid in. I felt a few moments of intense pain at this point, and moaned a little when she first started. But it quickly subsided and was replaced by pleasure. I continued to let out moans, but now of pleasure rather than pain, she kept pushing, harder and harder, deeper and deeper, until it was in all the way and I could feel juices splashing from her pussy onto my balls. She kept fucking me for a while until she slammed as deep as she could into my ass and stopped. I felt something warm and gooey release into my ass and then she pulled the cock out.
I turned towards Erin, “What was that?” I asked.
“Didn’t I mention this strap-on squirts cum?” She responded, “Oh well,” she said as she slapped my ass, “Go get yourself cleaned up and ready for bed, tomorrow’s the 15th, you’ve got a long day ahead of you.” And with that, she pushed me out the door, tossed my thong and cami to me, slapped my ass one more time, and then shut the door behind me.
As I headed to the shower for the second time today and felt the cum from my sister’s strap-on leaking from my asshole and dripping down my leg, I couldn’t help but think what an interesting four years this may turn out to be.
The End… Maybe?
