My Lovely Sister: Part X First Experience

Friday, July 10 th, 2009...

Back home the following morning, I did the things I usually did when I first woke up. Looking at the clock to ensure my parents would be gone for work, I exited my room still in my nightgown, and headed for the bathroom. I took care of business and made sure my hair was in order, then continued on to Mandy's room to get dressed. After looking through her drawers, I changed into a fresh pair of chocolate colored hipster panties, and a forest green sports bra; Mandy and I always did look good in earthy colors. From there I dressed in a denim mini skirt with a floral design embroidered into the waist line, a skirt that did nothing to hide my morning wood, and a tight t-shirt that actually showed the outline of the bra I wore.

I walked downstairs barefoot, and headed straight to the kitchen to have breakfast. Mandy was already there, sitting at the table with her notebook computer, and wearing something that took me by surprise. It was a sexy version of a school-girl outfit. Her black and white plaid skirt was actually more of a micro than a mini, which easily showed her lack of panties. Most of her legs were covered in opaque white thigh high stockings, and her feet were slipped into black, five inch pumps. Her white, button down blouse was barely lower than her breasts—and from the way her nipples poked out I knew she wore no bra—and the sleeves were so short they were almost non-existent. Completing the look, she wore a black and white plaid neck tie, hanging loose on her breasts.

“Good morning, love,” my sister said to me as she stood and approached, her heels clicking loudly on the kitchen floor. Those heels actually made her taller than I, and she had to lean down a bit to kiss me, firmly grabbing my pantied hard-on as she did. Of course, that only ensured I would have my erection that much longer. As she turned around to head back to her computer, I gave her ass a playful slap.

“Not that I mind,” I began, still looking at my sister's hot body in that sexy outfit, “but what's with the outfit?”

“I found a party for us to go to,” Mandy replied. “It's a costume party, so you might want to get changed.”

“But I don't have a costume.”

“Sure you do,” my sister assured me. “You can wear that french maid outfit you wore at Danielle's a few days ago.” Mandy must have noticed with worried look on my face, because she shook her head lightly with a smile as she continued. “Don't worry, you won't be the only crossdresser there. It's a party for people like us—sisters who are madly in love with their crossdressing brothers.” My worry turned to excitement as I heard those words, and I found myself anxious to meet others not unlike myself.

Mandy waited patiently for me to get changed into the french maid uniform, complete with the black wig. I was still quite erect, but the petticoat was doing a nice job of hiding that fact. As I stood before my sister in the kitchen once more, she approached me slowly with a smile. With her body pressing lightly against mine, she leaned in and kissed me, just as passionately as the first time. “We have some time before we have to leave,” she said to me. Taking me by the hand, Mandy led me into our parents' bedroom—where there was a queen sized bed—and pushed me onto it.

I fell on my back hard enough to bounce lightly, the skirt of the maid's dress falling off of the petticoat slip. As I lifted my arms onto their elbows, Mandy reached under the petticoat and grabbed the sides of the white pantyhose I now wore, along with the white satin panties under them. She pulled them down to my knees and stopped, making certain I could only open my legs so far. Then she crawled over me and shoved her tongue down my throat again, pushing me back onto the bed as she did.

With me lying on my back again, Mandy guided my hands underneath her blouse and over her voluptuous breasts, then reached down and grabbed my cock once my hands were occupied. We moaned together through our kiss, my hands caressing her breasts, her hands gloving my cock and leading it inside of her. Mandy broke our kiss and tried to sit up on me, but I quickly grabbed her neck tie and pulled her back down. Wrapping my arms underneath hers and my hands over her shoulders, I held her as tight as I could, pushing deeply into my sister's body. Her face tightened as she let out a squeal of ecstasy.

I continued to pump my sister hard, until I could handle being under her no longer. With a hard motion, I rolled over on top of my sister without pulling out of her and began fucking even harder.

“Oh my god, oh my god, oh my god!” Mandy cried out, and I knew she was close. Suddenly her body jerked, and she gripped my body with a strength I didn't know she had. At that same moment, I thrust forward and held that position, shooting my load. I shot so hard I feared I would break the condom. Finally, it was over, and I rested on my sister, the two of us catching our breath.

The drive to the party later that day had taken at least three hours, and we didn't arrive until just after six in the evening. Knowing what I was heading into, I found myself lacking the usual tension I often carried when meeting new people while cross dressed. When I stepped into the host's house with Mandy, I smiled wide, unable to believe my eyes. There was a nice mix of both males and females at the party—all appearing to be in their late teens—and everyone was dressed in feminine costumes. I truly was no alone in this.

“By the way,” Mandy said to me before leaving my side. “This is also a swingers party, so feel free to flirt.” Mandy gave me a wink, then went on to mingle with the crowd. As for me, I grabbed a can of soda from the nearby cooler and looked to the T.V., where a pornographic movie was being enjoyed by two guys, who touched each other while watching. One of them was dressed like a hooker in a shiny green vinyl micro skirt, a ripped tank top that barely covered his nipples, fish net stockings, and a pink mesh thong. The other was dressed like a fairy, wearing a glittering pink two piece outfit: a loose mini skirt with a jagged shaped bottom seam, and sleeveless midriff top, and transparent pink wings attached to the back of that midriff. Both their gazes were locked on the porno, but their hands were busy. The hooker's hand was underneath the fairy's skirt through the top, stroking slowly, and the fairy's hand had lifted the hooker's micro skirt and freed his cock through a leg hole of this thong. He was stroking him as well.

“Hey,” a voice beside me said, suddenly breaking my trance. I jumped, slightly startled, as I turned to the boy who had addressed me, finally noticing how erect I had become; good thing I wore a petticoat that hid it. The boy was slightly taller than me, and looked like a playboy bunny. The bunny uniform itself was a light, pastel pink, worn over a pair of darker pink pantyhose. On his head were the ears, the outside of them the pastel shade, the inside the darker shade. Finally on his feet where a pair of five inch peep-toe heels with triple ankle straps. “Didn't mean to scare you,” he added with a smirk.

“No, it's me,” I assured. “I can be jumpy sometimes.” It was then that I noticed this boy had altered the uniform he wore. On the crotch was a zipper, allowing for easy access. I had guess that he wasn't wearing any panties underneath. Before he could notice my gaze, however, I brought my eyes back to his and spoke again. “So what's your name?”

“Jake,” he replied.

“Kyle,” I introduced. “Nice outfit. It's sexy.”

Jake touched the hem of my skirt invitingly with a smile. “Yours isn't too bad either.” I blushed briefly, averting my eyes to avoid letting Jake see it. I had never taken an interest in other guys before, but Jake was downright hot! Long, shoulder length hair that shined like that of a celebrity, split on the side, feathered bangs, and colored a smooth chestnut. It was obvious that Jake was comfortable with his feminine side.

“So,” I finally began again. “Which one is your sister?”

Jake nodded across the room. “The sexy cat there.” I looked to where Jake had gestured, and found her. She had a nice tan, and was dressed in a skin-tight catsuit, complete with heels, fingerless gloves, and cat ears. “Anyway,” Jake continued, “the reason I came to talk to you is... I think you're the sexiest person here.”

I looked into Jake's eyes and knew exactly what he wanted. I shook my head lightly, suddenly as tense as ever. “I don't know,” I told him. “I mean, I've never been with another guy before.”

“Don't worry,” Jake said, his voice so soothing. “I know how to handle a newbie.”

Before I even knew what was happening, my hand was being held by Jake, and he was leading me away from the crowd, toward the stairs to the second floor. What was astonishing was the fact that, despite his lead wasn't forceful, I was easily following. He led me into what could only be the master bedroom of the house, with a queen sized bed along the wall, sided with dressers, a T.V. across the room, and a full bathroom to the left of the bedroom doorway. There was also a walk-in closet further back.

As soon as the door was closed, Jake moved his lips to mine. His kiss was soft and gentle, and he only initiated so much of it. Knowing that I was being allowed to set the pace, I then leaned into Jake, deepening our kiss. I was already rock hard by this point, as I'm sure Jake was also. After a few minutes of simply tongue wrestling with him, I finally wrapped my arms around his waist and pulled him with me, as I stepped backward towards the bed. As I sat, Jake let our kiss break and knelt down in front of me. I invitingly opened my legs, and Jake reached his hands underneath my dress and slip, and slid his fingers under the band of my panties and pantyhose. He pulled them down slowly until they were off, keeping his gaze locked on mine the entire time. Then he reached under again, grabbing firm handfuls of my petticoat and removing it just as slow.

With nothing left to hide my erection, my cock was holding the skirt of my dress up. “Wow,” Jake said softly, more for my own benefit than his own. “I like that.” Rather than simply pull the skirt out of the way, Jake slid it back, letting the fabric rub against the head of my cock. I jerked a little, feeling like I was going to burst early.

Still gazing deeply into one another's eyes, Jake opened his mouth and slid his tongue forward. He licked the shaft of my cock, starting at the bottom and slowly moving up until he could lap at the head. I leaned back, tilting my head behind my shoulders as I let out a whispering moan. By the time I had looked down at Jake again, his lips were wrapped completely around my cock, moving their way down to the base. His hands found their way upward along my body to my chest, caressing it as if I had breasts. I responded with my own hand, grabbing Jake's silky hair and taking control of his head movements. I kept it slow, hearing him moan in a high pitch, feminine voice; it was obvious that he was really enjoying this.

Jake soon grabbed my sides and pulled me, back up a little as he did. With me now standing, Jake cupped my butt into both of his hands (over the dress) and continued to suck my cock. I could feel it coming now, nearly there, and I picked up speed. Before I knew it, I was pumping Jake's mouth wildly, letting out wild shouts of ecstasy.

Suddenly I exploded, shooting hot cum hard into Jake's mouth, and I let out a loud squeal. I prayed I was muffled by the music downstairs, that no one would hear me. After a few shots, I could even feel my own cum spilling from Jake's lips onto my balls. The fact that Jake kept on sucking after I was finished was torture.

“Oh god, please!” I pleaded, the pleasure being too much to handle. Jake finally stopped, swallowing the last bit and wiping his lower lip.

“Okay,” he said. “My turn.”

“I don't know if I'm ready to suck cock,” I told him.

Nonetheless, Jake unzipped the crotch of his bunny outfit, freeing his erection, wet with precum. “I'm not putting it in your mouth.” He laid me back on the bed with one hand, and stroked himself with the other. I thought to protest, and Jake must have realized that. “Trust me,” he said, before any words could escape me. I did just that, lifting my knees with my legs spread apart, and pulling my dress up and out of the way.

Within seconds, Jake was cumming, making sure his load covered my anal hole. “That was it?” I asked. Jake shook his head with a smirk, and I realized that was only his first load, to act as a lubricant. Still fully erect, Jake began sliding into me. I must admit, that first time hurt like hell, but there was something exhilarating about it that made me want him to pump hard. With me even making a verbal request, he obliged me, his thighs slapping hard against my ass cheeks. I found myself masturbating, wanting to cum again myself.

“Oh my god!” I exclaimed, grabbed at the fabric of his outfit with my free hand, trying to pull myself up. “Kiss me!” Once again, Jake obliged, throwing his body down onto mine, and locking our mouths together. Immediately, I began cumming between our bodies, and I also felt Jake's cock jerk hard before unleashing inside of me. I could tell it was difficult for him, but Jake actually managed not to push harder than he already was; he certainly did know how to handle a newbie.

When it was done, Jake slowly pulled himself out of my body and lay down beside me. We didn't even realize we had drifted off to sleep until we were awaking the next morning.