The Dress Rehearsal
Emma dresses her brother, as he becomes her sister for the day.
A couple of days passed without another incident before his day of reckoning with his sister. It was Tuesday the day Emma had organised for the dress rehearsal and Steve had woken late with his usual morning 'hard-on'. He peered under the sheets and smiled at his engorged cock that was just begging to be relieved.
Wrapping his hands around his cock, Steve slowly worked them up and down his swollen shaft as he remembered the events of the previous weekend. He hadn't been able to stop thinking about his sister and the blowjob she had given him. She had even swallowed his cum which was awesome. Then of course, there was her beautiful tits that she had let him fondle.
As he continued to fantasise about her, Steve's hands increased their tempo on his cock until he stopped abruptly, and held still as a stream of cum spurted from the tip of his cock into the air before landing on his belly.
"Fuck, that was good.”." He whispered to himself, as he quickly scooped his cum up with his fingers and sucked them clean.
As he lay in bed, he wondered whether Emma had forgotten about their little arrangement, but his anxiety was short lived. Just after lunch he heard the front door open and someone hurrying up the stairs.
Emma popped her head around Steve's bedroom door laden with numerous shopping bags.
"Hello, you must see what I've bought you!" Emma proclaimed excitedly, adding "I'm gonna dress you up in a lovely little red cocktail dress."
"Yeah, sure, show me Em." Steve answered, not too sure whether Emma was serious about their little excursion this coming Friday.
Emma pulled out a red mini cocktail dress with a flirty hem and held it up for his approval. "Like it?"
Steve now realised that his sister was deadly serious, and his face lit up with a huge grin as he imagined himself in the little red dress. "It's... gorgeous sis." he mumbled but it'd look better on you Em.
"Trust me, you'll look great I promise, and it'll be a blast!" Emma replied trying her best to convince her sceptical brother.
"And to make you look a bit more convincing darling, I've bought you some boobs and a lovely wig." She declared excitedly, holding out a long wavy wig for him to examine.
"Go on, try it on." She coaxed as her reluctant brother smiled nervously. He cautiously stroked the long flowing wig and had to admit, that it did feel like the real thing and looked so flirty. The hair was soft and lifelike and even he was impressed with his sister's purchase.
"It feels so real, Em."
Steve stood up, and in front of the mirror placed the wig on his head, adjusting it so that the parting was just a little off center. He brushed aside the shorter layers that framed his square shaped face and looking over his shoulder into the mirror. He smiled as the long flowing wavy curls cascaded over his shoulders and down his back.
He could hardly believe the sight before him in the mirror. He was instantly transformed with the long wavy locks. As he touched and caressed his new head of hair, he smiled to himself. He had never had such long hair before. Always sporting a 'short back and sides' style, but now the look and feel of this soft mass of hair excited him, and even he had to admit that he thought it suited him.
"Isn't it fab!" Emma proclaimed.
"Well I must admit, I do kinda like it." Steve reluctantly admitted to his sister.
Emma then produced the false breasts from the shopping bag. They were made from silicon and were quite large and heavy, she had obviously been swayed by her own large breasts when choosing a suitable 'cup' for him. He was totally transfixed with the real lifelike feel of the silicon breasts and how they moved when he squeezed them, just like Emma's boobs did when he squeezed them the other day.
At the tips were tiny hard nipples that protruded just enough to announce to the world how excited she was. Steve squeezed and kneed them between his thumb and forefinger and at the same time he felt the familiar twitching between his legs.
A huge grin crept upon his face as he realise just how excited the dressing up was making him feel. Emma once again reached into her shopping bag and brought out a sexy red lace bra set, comprising of under-wired plunge bra, matching thong, and a pair of red lace stockings. She held the bra and thong against herself and asked, "Do you like them?"
Steve was speechless. It was gorgeous and so, so sexy. The look on his face must have said it all, as Emma then asked, "Are you ready to get dressed sis?"
"Yes ..." was all he could say to answer her question.
"Right then, top off and lets give you some boobs sis!" Emma ordered.
Nervously Steve removed his clothing while Emma began fixing the heavy silicon boobs to his chest with the fixing tape she had bought. Eventually the boobs were secure, hanging in front of him like two large melons. He stood in front of the mirror squeezing and caressing his new tits, watching as they wobbled and bounced just like real boobs.
"Do you like them?" Emma asked.
"Love em," Steve replied in awe at his new transformation.
"Right sis, trousers off, bra and panties on," Emma instructed while adjusting the shoulder straps of the new bra. Once satisfied with the adjustments she beckoned her brother over and offered it to him to slip on.
Steve had no problem wrapping the bra around his new breasts and fixing the clip behind him, before adjusting the bra to fit comfortably. It looked beautiful, encasing his 'D' cup boobs that were pushed tight together and up, creating an instant cleavage.
"It's gorgeous Emma," was all he could say.
Meanwhile Emma was unbuttoning his trousers and the familiar sound of his zip being opened was heard. Then she allowed his trousers to fall and settle around his ankles. Kneeling before him she stroked his semi-erection that was clearly visible beneath his tight Calvin Klein shorts. Her finger traced the outline of his cock before she looked up at her brother. “Maybe later eh?” She promised as she quickly tugged his shorts down, allowing his semi-erection to spring free.
Then almost as quick, she jumped up and reached into the shopping bag for the new thong. After removing the sales tag she knelt down again and offered them to her brother. Once he had stepped in, she pulled them up and adjusted them to fit snugly between his cheeks and around his cock and balls. The stiff lace against his cock sent shivers of ecstasy through his tense body and he f elt a stirring in his loins as his cock began to swell and stiffen.
"Sit down and let me help you into your stockings," Emma ordered once more as she unwrapped a pair of red lace hold up stockings.
Steve sat obediently on the bed and watched intently as his sister expertly guided his foot into the stocking, pulling it along the length of his smooth, clean shaven leg. Then repeating this process with his other, until they were both totally encased in the silky red stockings.
Once his sister had finished he stood up and admired himself in the mirror, smiling at the wonderful feminine figure that was stood before him with the womanly curves. The lingerie looked perfect and he felt so feminine.
While her brother posed in front of the mirror, Emma retrieved the little red cocktail dress from the carrier bag and began cutting the sales tag from the dress label. Then offering it to her brother she motioned for him to put it on.
Unzipping the zip, Steve slipped into the tiny red dress and pulled it up, securing the thin criss-cross straps over his shoulders. It was a tight figure hugging dress that enhanced every curve of his womanly body, the short flared skirt only just covering his cute bum, while his long slender legs begged to be caressed.
"Oh, I almost forgot, you've no shoes." Emma cried as she looked her brother up and down. Running into her room, she searched through her wardrobe and retrieved a pair of heeled sandals before returning to her brother.
"Can you walk in these?" She asked, showing Steve the sandals.
"I'll try," he replied as he stepped into them. They were a little small for his feet but Emma assured him they would be OK. Almost immediately as he straighten up, he wobbled and swayed in the high heels, but determined to persevere he set off to wobble his way to the mirror. Looking at his reflection, the dress, boobs and shoes made him look tall, slim and curvy. He smiled at himself.
"You'll have to practice before Friday." Emma chuckled as she watched her brother struggle to walk in her heels.
As he became accustomed to his new outfit, Steve felt all the sensual feelings come flooding back to him, causing a little bulge in his lace thong. Then demonstrating his new outfit he gave Emma a complete twirl allowing the flared hem to lift and expose the lace at the top of his stockings.
"Careful sis!" Emma exclaimed, "If you do that when we're out, you'll have every lustful bloke within miles sniffing around!" She added with a laugh.
"Emma, this feels so wonderful, I can't believe it!" Steve replied, the excitement in his voice hard to disguise. "I never thought I could feel like this!"
"Let's go to my room so I can finish you off," Julie ordered holding out her hand for Steve.
Once in Emma's room she told him. “All we have to do now is put your make-up on,” and set about gathering various pieces of make-up off her dresser, before instructing her brother to sit down on the bed.
Steve sat patiently while his sister first plucked his thick eyebrows. Only when she was satisfied she'd thinned and narrowed them enough did she stand back to admire her handiwork, before she began to paint his face.
Beginning with foundation to match his fresh young complexion, she applied an even coat to cover his face and give her a clear canvas on which to apply the various colours she knew would bring his facial features to life. Then using her blusher brush, she expertly applied blush to highlight and 'lift' his cheekbones until she had achieved a warm, natural look.
Next Emma meticulously applied eye-shadow until she had transformed the appearance of his eyes, flattering their shape and colour with different shades of brown before using an eye-liner pencil. She carefully drew around his eye highlighting the eye shape before applying a thick layer of mascara to his eyelashes. The end effect was a striking and seductive finish to his eyes.
Finally Emma ordered her brother to pout his lips while she applied a glossy 'Sunset Glow' coloured lipstick to finished his makeover. Once she was satisfied she handed him her hand mirror and urged him to look.
"Wow, sis, I look gorgeous."
Emma lent over and gave her brother a small peck on the cheek adding, "You ARE gorgeous."
Steve smiled, and nervously made his way to the full length mirror, unsteady once more in the high heels and stood starring at his reflection, not quite believing that the person standing there before him was indeed himself. It was amazing. Emma had totally transformed him from the young looking boyish brother into a hot, sexy, glamorous sister.
He looked himself up and down in the mirror taking in the long flowing hair of the wig that cascaded over his shoulders and down his back. He loved the provocative little red dress with it's flared hem, and his large firm silicon boobs displaying an alluring cleavage that would get the attention of everyone whom he came in contact with. He smiled as he admired his long slender shaven legs in their red stockings and the high heeled sandals which made him feel that much taller. Steve felt wonderful and he knew nobody would imagine for a moment that he wasn't anything other then a sexy young woman.
"I look gorgeous... I FEEL gorgeous." Steve muttered to his reflection.
"I'm glad you like it.., I'm gonna call you Stephanie and your gonna be my little sister from now on, OK?"
"OK, sis." he replied smiling.
Emma sat on her bed and watched with satisfaction as 'Stephanie' continued to admire herself in the mirror, before emptying the remaining shopping bags. Holding up a black lace shelf bra in front of her she asked, "Want me to try it on? Give you a little peek?"
"Yeah," was all he could manage to say, hardly taking his eyes off the image in the mirror.
"Just give me a few minutes, and I'll give you a shout. OK?" And with that, Emma disappeared with her new underwear.
Steve's concentration was suddenly broken when he heard Emma call out from behind the door. He turned around just as the door opened and Emma reappeared. For a moment he was not quite prepared for the sight that greeted him.
There standing at the other side of the room was Emma, dressed in a black lace shelf bra, matching thong, suspender belt and stockings. To finish off, she wore a pair of black stiletto heeled shoes that made her look much taller. She looked absolutely stunning.
Her large breasts were beautifully exposed and supported by the sturdy shelf bra; her nipples already erect and tantalisingly just begging to be sucked. The small matching thong she wore failed to conceal her small trimmed dark bush of pubic hair, and her long slender legs were covered with a pair of black sheer stockings which were in turn attached to a matching lace suspender belt.
She squeezed and gently tugged at her nipples for her brothers benefit, before she realised her new sister had a stiff tent pole poking out through the front of her dress.
Giggling, Emma rushed over to her sister and and gave her a twirl, allowing her to examine her nakedness from every angle. Her sister meanwhile, just starred open mouthed at the sight of this voluptuous woman in her lacy underwear and high heels.
"What da ya think sis? I love it and I know John will love it too..."
"Lucky John ..." Stephanie replied, with a little disappointment in her voice. "You've not bought it for me, then, Em?"
"Sorry little sister, this one's for John. I don’t mind showing you though, now and again if you’re a good girl! Maybe if it doesn't work out with John in the future..." she teased provocatively.
And with that she turned around throwing her long dark hair from side to side. "Fuck," Stephanie thought “She’s really turning me on,” as he felt the erection in his panties twitch once more.
Emma twirled around once again smiling and laughing at the effect her underwear was having on Stephanie, and then crossing her legs she bent down to touch her toes and show off her beautiful bum. The black thong tucked tightly between her cheeks and her raised mound looked so inviting, it was delightful. When she turned around again to face him he could clearly see her trimmed pussy through the lace material.
He stood, jaw ajar taking in the sight of his beautiful and voluptuous sister as she spun, twirled and teased him with her sexuality.
"Emma, I don't know if I should be doing this."
Emma looked at him, surprised.
"Why? You enjoy wearing my underwear didn't you?" she asked him.
"Yes, but it's going a bit too far this dressing up. Especially going out to town like this. If someone sees me, I'll die!"
"No one will recognise you, honestly, believe me." Emma assured him, her hand stroking the bulge in the front of his dress.
"Don't worry about what could or might happen, just enjoy the moment." Emma teased, slipping her hand under Stephanie's dress and squeezing his cock. "Now, what if I said, I'd like to give you a blowjob?"
Steve smiled remembering the last blowjob she had given him, "Now? You'd suck my cock?" he asked.
"Oh yes, I've been dreaming about that dick of yours since last Saturday! But you must be prepared to return the favour of course."
"I'll suck your dick and in return you lick my pussy until I cum, OK?"
"Fuck, OK," Steve replied trying to conceal his excitement. "I'm up for that Em... " he agreed tentatively, as a huge grin crept upon his face.
Emma made her way to the bed while Stephanie followed, her cock straining desperately against her thong. Then Emma spun around and pushed Stephanie towards her bed. Losing her balance she fell onto the bed, while Emma knelt between her open legs.
Reaching for Stephanie's dick, Emma released it from his lace thong and slowly began to stroke and squeeze it, bringing it back to life. She continued for a minute or two, then smiled at the results of her massaging. His dick, with its veins bulging to bursting point and its shiny head glistening with pre-cum was now fully erect. She marvelled at its sheer size and thickness before slowly lowering her head to his dick.
She licked its head and smiled as it twitch with her touch, before running her tongue down the length of his shaft only stopping to nibble at his tight sack that held his balls. Steve moaned in appreciation as his sister pleasured his cock.
Then he looked down to see Emma open her mouth as she took the head of his cock into her mouth. She sucked eagerly, her head bobbing up and down his long shaft while Steve enjoyed the sexual pleasure that came from her endeavours.
As she sucked, she continued to work her hand up and down his long shaft. She now found her brother thrusting his hips once more like he did last Saturday, forcing his dick against the back of her throat and causing her to gag at first, before releasing him in a coughing fit. She looked up at her brother as she continued to toy with his dick, her fist pumping his erection as it stood upright, stiff and swollen.
"God, I still can't believe how beautiful this dick is," she said to him in awe.
Steve moaned with pleasure as she resumed sucking on his cock, taking his erection between her full lips. She rocked her body back and forth, as her head bobbed up and down his swollen shaft in unison with his thrust as he rammed his cock deep into the back of her throat.
Steve with his eyes closed, was moaning as he thrust his cock into her mouth. Then, he suddenly stopped. The familiar feelings of an approaching orgasm overcame him as his cock erupted spewing its contents into his sister's mouth.
Emma was surprise by the amount of thick warm, salty cum that was blasted into her mouth. She gagged and allowed some of his cum to ran out of the corner of her mouth. She swallowed the first load, then opening her mouth she aimed his cock so that the next spurt she caught in her mouth. Then the third and final squirt, hit her on the bridge of her nose and dribbled down over her lip and down her chin, to be caught by her tongue as she licked it clean.
"Fuck, that was good," laughed Emma as Steve opened his eyes to surveyed the mess on Emma's pretty face.
"Em, your wicked!" Steve whispered in total awe of his sister.
Smiling, Emma got off her knees and sat on the bed next to her brother. Turning to face him she lent over and kissed him on his lips. A long, loving, passionate kiss; their tongues exploring each others mouths as Steve tasted the taste of his salty cum in her mouth. When they broke for air, he wiped the last remaining globule of sperm from her chin and sucked his finger clean.
Emma giggled as she watched her brother eat his own cum, "Isn't it yummy?" She asked before ordering her brother to repay the favour with, "It's my turn now Steph."
Lying down on her back Emma quickly slipped out of her thong, and parting her legs she indicated for Steve to start kissing. His eyes feasted on her neatly trimmed pussy and he smiled coyly, before crawling off the bed and positioning himself on his knees at the end of her bed. Reaching for her open legs he pulled her towards himself at the end of bed before placing a delicate kiss on her pussy.
He stared in wonder at the sight before him and slowly ran his finger down her pussy lips, applying just enough pressure so he could slip his finger inside and wet it with her juices before bringing it to his lips to taste.
Liking the taste, he returned his finger to her slit, but this time he parted her lips and gently stroked her clit. She was wet with anticipation as he push first one, then two fingers inside her dripping pussy before withdrawing and offering his fingers to his sister's lips. She eagerly accepted, and slowly but seductively she sucked his fingers clean.
The anticipation of what was coming was driving Emma wild. Her chest heaved up and down as her breathing quicken, desperate to experience her own orgasm she pleaded with Steve to eat her pussy.
In response to her pleas Steve laid first one, then two kisses around her inner thigh before he trailed his tongue upwards, getting closer to the area he knew she wanted pleasuring more then any other. As he did so, Emma moaned with delight as he planted kiss after kiss, getting closer and closer to her tender lips, and driving his sister wild.
As he neared her pussy, Emma reached down and parted her lips. Then begged her brother, "Please, please lick my pussy."
He pushed his tongue inside her hole concentrating on her clit. Each time he sucked and rubbed her clit, she moaned, gasped and writhed, urging him on as she was driven into ecstasy.
"Please, please, don't stop Steve... Oh God, yes, yes, more, right there, Oh God YES!" Emma cried out as she gripped her brother's head between her thighs in a vice like grip, her orgasm flowing through her body.
Her pussy was dripping wet from her pleasure and Steve felt her juices against his face. It tasted so, so sweet as he lapped at it.
"Fuck, that was so good Steve," was all she could manage to say as she lay on the bed, exhausted and spent.
Steve joined his sister on the bed and rested with her. After a few minutes without a word being spoken, Emma wrapped her arms around her brother and whispered in his ear, "Love you..."