Crossdressing Brother

With the first two stories written from Claire's point of view, I thought that I might be interesting to write it from Greg's (her brother's) point of view.

*

It was a hot morning, waking, covered in sweat. I rolled out of bed, and I was sitting on the edge of the bed, when my sister came into my room--marched actually,

"I don't mind doing your laundry, Greg, but you got make sure that it is out by the machine, and now you are out of clothes and underwear. They're all dirty. And why didn't you didn't tell me you were getting so low?"

Still somewhat asleep, I thought about it a moment, then replied that I didn't think I was out, or even close to it. Claire hand a stern look on her face and said, "Well, you are." Then, from behind her back, she produced some clothing and laid it on my bed.

"These will have to do for now, till I can get some washed. Put them on." She paused a moment, then added. "Besides, I think you'll like them better. It's hot today, and these will be cool." She left the room. I looked lazily at what was before me, on my bed, there was a pair of woman's G-string panties, a pair of her shorts and a cotton sleeveless blouse of hers (we were almost about the same size then).

"Uh, sis," I yelled, No response. I yelled again. This time I heard her roar back to just put them on. I shrugged and took off my boxers and then slipped on her G-string. They fitted remarkable well, the g-string came up and slid up between my butt crack, and it snuggle fitted my testicles. I immediately felt an incredibly good sensation. Especially around in my genitals, which did, I must admit, sort of bulge out in front. I shrugged again and then put on her shorts, zipping them at the side and then slipped her blouse on. No sooner had I finished than did, Claire suddenly appear again.

"You'll be much cooler in that. I guarantee. And you'll feel better too. Now, here, put these on too." From around her back she produced a pair of red shorts, which I put on in front of her

"Okay, now go and watch some TV or something. Stay inside, though. It's too hot outside," she said and I obeyed.

Walking away, feeling rather strange but oddly good too. For a long time I'd always rather envied women because they have such a variety of clothing they can wear, much of which seems so airy and comfortable. And now I was getting to experience this. I kind of liked it, in a way. Plus, I knew it pleased Claire in some strange way. It also pleased something else, which had grown quite large in my panties. They offered some support and it was pushing it way out quite noticeably. I tried to ignore it and after a while, it did subside somewhat, although not completely. I walked downstairs and turned the TV on and began to watch it.

An hour or so later, Claire called me up from the den. I went and found her in the bathroom. The water was running in the tub.

"I want you to take a bath," she said.

"Do I have to?" I asked.

"Do as I say!" she snapped. "Get undressed."

She left the bathroom. I did as I was told. As I did, I noticed some more women's panties, a bra on the toilet seat. "Now, what?" I thought. In a moment, I was completely naked.

"Aw Sis, I don't' need a bath!" I said trying to get out of her grasp,

"Yes you do, you are all sweaty and smelly," she said,

"Aw Sis, I don't' need a bath!" I said trying to stand my ground.

"Do as I say!" she snapped. "Get undressed."

She left the bathroom. I did as I was told. In a moment, I was completely naked. Standing there naked, daydreaming, and thinking about the past, and how Claire used to bath me when I was younger. I started for the tub when Claire suddenly entered the bathroom. She handed me a can of shaving cream and a razor.

"I want all that ugly hair off you," she ordered.

"I don't know why men have to have so much hair. It's ugly. And hot. You'll feel much better afterwards." But I just stood there. She lost her patience and shoved me into the tub. She started to wash me, everywhere. She rubbed my cock and balls vigorously, but all the while seemingly ignoring my full-scale erection. She then proceeded to put shaving cream all over my legs and under my arms. In a state of semi-shock, I just let her. In a matter of minutes, it was over. She sponged me off and gave me a towel. I tried to stand with my front away from her. My penis was very large and stiff by now. She pointed to the dainties on the toilet seat.

"Put those on," she said, and these shoes."

She handed me some very feminine wedge-type house slippers, open-toed, backless, with a feather puff on the toe. I slipped them on, after draping myself in a silky nightgown. She led me to my bedroom where I noticed several feminine articles were laid out on the bed. She sat me down, slipped off one of my slippers and then proceeded to paint my toenails a bright, iridescent pink. She did one foot, then the other. My mind began to race. What was going on? I was fearful, yet another part of me was excited, thrilled, and more so than I'd ever been in my entire life!

"Was I going to like it?" I thought to myself, I don't know, but the combination of the hot bath, the smooth legs, stimulated from shaving and cool and soft from lotion, with the soft, soft nightgown, oh, so feminine! -- it made me feel very good. Claire finished, and told me to relax while the polish dried. I laid back on the bed, kind of in a half-daze. I felt my maleness between my legs, my balls swollen and beginning to ache a little, and my stiffness, all surrounded by the softness of the nightgown. I found my hand wandering down there to massage it. But then Claire suddenly came into the room and said,

"Ah, ah. None of that." I pulled my hand away embarrassingly.

She had me stand up now and then had me take off my nightgown. I stood there, naked, except for the house slippers, with this long, erect cock protruding from my crotch. Mom mumbled something like,

"Silly things. They just get in the way." What happened next seemed to occur in an altered state almost. Before I knew it, Claire was fastening a pink garter belt around my waste. She had me step into a fresh pair of pink panties, very soft and satiny. She pulled them up snug around my hips and made sure the garters dangled freely behind and through them. Next, she put a bra on me. A black, sexy bra, she wrapped around my chest and hooked it up at the back.

"Every girl has to have a bra," she said. She then put some kind of jelly-like inserts into the cups, which were about 36B. I felt the weight and jiggle ness and thought, is this how it feels to be a female? If so, I liked it. She then sat me on the bed and removed my slippers. She reached around behind me and brought up a flat box and opened.

"Now you'll know what living is, what you've been missing." It was a pair of sheer suntan nylon stockings, with reinforced heel and toe. I hardly remember what happened next, except it felt so damm good. She gathered one up and helped put my right foot into it. Then she slowly pulled it up my cleanly shaved leg, over my knee and high up on my thigh. I've never felt anything like it. It was sheer pleasure, along with freedom and abandon. I can hardly describe it.

When the stocking was on, she hooked the garters onto its soft top, and then proceeded to help me put the other one on. I did help some this time, and it was wonderful. But something else was occurring to, or was about to. My penis was stiffening, and oozing. In my groin was a pressure. I felt a terrible itch in my shaft. I also felt a throbbing. With the stockings in place, Claire stood me up. She helped me into my slippers. God, they slid on so smoothly. My feet began to tickle me sexually. As I adjusted to that wonderful sensation, Claire then helped me put on a pink, satiny full slip. I revelled as it fell down by body, touching my skin and other satiny and nylon encased parts of it. It almost felt like electric as it fell around my nylon-covered smooth legs.

At the same time, it felt like something was goosing me. I felt an intense itch in my groin. I must have buckled a little. Claire shook her head and had me lie back on the bed, with my beautiful legs draped over the edge. She then lifted my slip and pulled down my panties a bit.

Without warning, she dropped to her knees and kissed the head of my cock tenderly. She had her hand around my balls so I didn't dare even move but I felt like crawling into a hole. After kissing my prick, she began drooling over it, literally. She slobbered on it then sucked it into her mouth to lick away the slobber. She kissed down one side, and then nibbled up the other. She sucked and swallowed as she slid onto my cock until her nose pushed into my tummy. I felt severe panic along with all the wonderful feelings Claire was giving me.

"Mmmm, your touch is nice," I sighed, slowly straightening up on my bed.

"Ooh yes," I sighed as my sister's hand began to caress my thickening cock. I opened my young thighs to allow her exploring hands greater access. My cock was hard and rigid. She looked down at it as it sprouted proud and straight from between my legs, pointing upwards, marvelled at its large smooth shiny head.

"For God's sake don't cum yet," she said to me, as she reached down and took my thick balls in her hand. "Oh, I like it," I moaned. Claire looked straight into my eyes and asked,

"Will you help your big sister out, Greg? I need something very badly, right now, please."

Before I could reply, she took on of my hands and guided it to the hem of her skirt. My eyes were bulging out of their sockets, as I slowly realized what my sister meant. I slowly slid a hand up under her short skirt, resting it on top of her tiny panties, until I found her smooth naked skin at the top. Pulling the waist band, I tugged the panties down over her trim bottom, and she kicked them off, and opened her slim thighs as wide as she could, allowing my inexperienced hand to her hot sopping fanny. My young searching fingers found the slippery hot inner lips, and the twitching hole near the bottom of my slit, and her little clitoris. Gently I explored my sister's eager cunt, sending shock waves all over her body.

"Rub my clit Greg, make me cum, Oh please, please make me cum, Oh Yes!" she purred. She felt my fingers begin to move faster and faster over her slippery swollen clit. She was still stroking my throbbing big prick, and she was surprised that her little brother had had cum yet. I fingered her very wet fanny, and soon her body rocked as her orgasm hit her.

"OH MY GOD, that was fucking great." She turned round and bent over me and pushed back her naked cheeks at me, revealing her open fanny to my horny eyes. I knew what I had to do, and taking hold of my huge tool, held it to her sopping cunt, he felt hot wet cunt walls close around my manhood as it slid inside of her pussy.

"OH LITTLE BROTHER, FUCK ME HARDER!" Claire panted, as her body consumed with lust and horn.

I eased my slim hips forward, sending his rigid tool into my sisters sopping hot cunt. I slid in about half way, paused, then I withdrew out almost to the tip then with another flexing of my firm buttocks thrust all the way in until I felt my skin on her skin.

"OH JEEZUS, FUCK GREG!" She cried out, as her sopping horny cunt was stuffed full with the thickness of her little Brothers, huge boyhood.

I began to fuck her, slowly at first, then with ever increasing speed. "Oh god, oh god, yes," I panted and gasped as my huge tool was thrusting in and out of my sisters cunt hungry little cunt. "Oh Greg, oh Greg, you are so good, fuck me, oh I need it oh yes. Oh yes, Oh yes, OH MY GOD!" she sobbed as her fanny was stuffed with my organ.

I reached under her short skirt and finding her naked trim hips, gripped them as I thrust in and out of her hole. Deep within her, I felt her cum begin to build up inside her, finally exploding from her sopping squelching cunt.

I felt her tight cunt walls, spasm around my thrusting boyhood, and this sent me over the edge. My boy seed, was freed from my young balls, and erupted time and time again from the tip of my cock, filling my sister's insides with its volume. I collapsed over my sister's back, gasping and panting for breath, after the most intense orgasm of his young life.

Claire had never felt so fucked, so stuffed, so fulfilled, so satisfied with any fuck that she had ever had, by me. With a loud plop she felt me withdraw me cock from her still throbbing cunt hole, my seed dribbling down her naked legs. She turned to me and kissed me on the mouth.

"Thank you, oh thank you Greg, you were fucking amazing." I was very pleased with myself. She got some tissues from beside the bed and wiped my dripping tool, and she got some more could wipe her fanny.

With another kiss, Claire got up and left me to regain my composer, only to return with some clean clothes to wear.

"Now take those sweaty underwear off," I got up off the bed and did as I was told. "Now I want you to put some fresh underwear on".

After putting on a fresh pair of knickers, she then returned with another nightie, she put it on me, I slipped between the sheets of my bed and I drifted off into feminine dream world.