Sister's Makeup Surprise - 1

I have a good friend, Susan, who works as a sales associate at a famous Chicago department store for a major cosmetics firm. I met her one day while doing a little shopping. During our rather extended conversation, she told me about her brother. He's about two years her junior, so that would make him...21, I suppose. They live in the same apartment building in the Streeterville neighborhood of Chicago, a popular place for young singles. Susan and her brother, Michael, shared their keys in case one of them locked themselves out of their apartment. Little did she know he used his key for another reason on that fateful day! And, well, I'll just relate what happened, in her own words.

Things were very slow that day at the store. It was a Monday afternoon, and Melissa, my friend over there in Lancôme, was getting-off soon, so I arranged to take the rest of the day off to go shopping with her. I wanted to rush home to change into something more appropriate for shopping, so we took a cab back to my place. Knowing Melissa the way I do, I knew she wouldn't care to change....she's very comfortable dressed to the nines, even to go shopping. I guess I can't blame her. She's so tall and thin and svelte and always looks ready to model for Allure or something. The sight of her walking down a city street in those heels she wears certainly attracts the guys! I guess that's why my brother always had the hots for her. He's never had the nerve to ask her out, but he asks about her a lot, and I can tell he's madly in love with her! He has a thing for redheads, you know.

Anyway, we got to my apartment, and we heard music playing. Not the stereo, but the radio in my bedroom. I thought I must have set the alarm clock wrong or something, so we went back there to shut it off and to change clothes. Well, you'll never guess what we found there! There was Michael, sitting at my vanity! He was wearing one of my Victoria's Secret bras with the matching panties, and had all my makeup spread-out across the vanity table. A wispy little garter belt surrounded his waist, holding-up smokey stockings that encased his freshly shaved legs.

He had already applied foundation and powder, and he would have begun applying blush, except we could see he was touching himself through his panties as he watched himself in the mirror. I'm not sure who was more surprised, us or Michael! He saw us in the mirror and turned absolutely white, then he blushed, furiously. Both Melissa and I cracked-up laughing as we walked-over to him. There was nothing he could do or say.....he'd been caught red-handed.

I was proud of the way Melissa regained her composure so quickly. She winked at me as she walked-up behind Michael, pushing gently but firmly on his shoulders, forcing him back into the chair, looking at him in the mirror as she spoke.

"So, Michael," she said, in a quiet but firm voice, laced with just a hint of sarcasm, "how long have you been playing with your sister's things? You look awfully cute, you know....for a little sissy." She couldn't help but giggle as she spoke, but she kept the pressure on his shoulders. He wasn't going anywhere.

Melissa was right.....Michael did look kind of cute, his slender form dressed in little else than a padded, underwire bra of satin jacquard with lace insets, in pink. With the matching high-cut brief, mind you! And his legs looked so shapely and feminine in nylons. His longish blonde hair was pulled into a pony tail, away from his face, revealing a flawless
complexion (thanks to Estée Lauder). He appeared agitated, though, as you might expect. After all, the girl of his dreams had found him in a most compromising position. And knowing Melissa the way I do, she was not about to pass-up this opportunity to humiliate him. She loved to toy with men. And Michael has always been a little shy and reserved...easy prey for Melissa.

Michael's natural inclination to leave was countered by Melissa's relentless pressure on his shoulders. He was absolutely stunned, and speechless. "Well, my dear," Melissa repeated, derisively, "I asked you a question. How long have you been playing with your sister's things?" I saw her long, red nails dig a little into his shoulders a little, for emphasis, as her countenance grew more stern.

Michael gasped slightly, his eyes widening, his breaths quick. "I just...um... wanted to see what it felt like, that's all...I've never done this before...really!" His eyes were moistening a little. "Here, let me take it off and I'll leave you alone," he offered, trying to stand.

"Oh, I don't know about that, do you, Susan?" Melissa had that sly look of hers as she gently stroked the side of Michael's face, her nails tracing lines that were both soothing and menacing. "I think we should finish where he left off, don't you?"

"I agree," I said, smiling, as I joined the two of them at the vanity. "After all, Michael, we are experts at makeup, aren't we? And besides, letting us finish you off is the least you could do to repay me for getting into my things." I toyed with Michael's bra strap to emphasize the point, while Melissa moved her hand from his face, down to his shoulder, and began gently stroking his chest through the bra cup. Michael winced a little at her boldness, but the tent in his panties grew even larger as she caressed the bra and, not incidentally, the tender skin underneath. Her crimson nails raked firmly against the bra fabric, just hard enough to elicit an audible gasp from Michael's lips. The resulting bulge in his panties was all we needed to see. That, and the little wet spot that began forming at the apex! I noticed that Michael's neck and shoulders had become rather flushed...a diffuse redness that I had noticed, before, whenever he became sexually aroused. For instance, when he had spent an unusual amount of time in the bathroom with a "borrowed" copy of my Cosmopolitan. It was then that it dawned on me that we had hit pay dirt.

Melissa noticed his response, as well, and continued her control of the situation. "Well, then, it's settled," she smiled, reaching for a lipstick on the vanity counter. She applied the lipstick to her lips carefully, exchanging glances with Michael as she spoke. "We'll just have to finish your makeup for you, little sissy," she stopped in mid-sentence, lipstick poised in mid-air, as if for emphasis, "and then we'll see what happens next, now won't we?" She examined herself carefully as she finished her touch-up, pressing her lips together as she turned her face from side-to-side. "Although I do wish we had something other than this Estée stuff to play with!" See winked at me, teasingly, then broke-out in a laugh. "This is going to be so much fun, isn't it, Susan! I can't believe
we have a little boy to play with all afternoon!"

I couldn't believe it, either, and I'm afraid neither could Michael. He was quite taken aback by the whole situation, which was just as well. He was so surprisingly docile that we couldn't help but take advantage of him. Melissa started to work on his eyes, lining them top and bottom in deep violet, drawing the upper line carefully, extending it a quarter-inch past his eyes, blending as she went. Meanwhile, I began painting his toenails in Burning Rose, trying as best I could not to stare at the growing member held tightly within his panties. My goodness, he seemed so aroused! Although he kept his hands submissively still on the arms of the chair as we worked, his hips fidgeted relentlessly, almost as though he were trying to hump something! Melissa kept-up an almost endless banter of chatter, goading and teasing and deriding him.

"Oh, these eye shadows are so sexy, Michael!" she said. "You're going to be so pretty when we finish with you. I'll just start with a light taupe all over the eyelid, like this...then I'll add a darker shade in the crease. I think Purple Number 7 does nicely. Mmmm, little girl! This looks sooo hot! See how this gives your eyes so much depth?" Then Melissa shocked me. After applying the purple, she reached down between Michael's legs and cupped his bulge, letting her nails rake across the top as she released him.

"Ohh! God!" Michael finally spoke, thrusting his hips, chasing the hand that tormented him so. "What are you doing to me, Melissa?!" His voice was pleading, almost desperate. I nearly dropped the nail polish.

Melissa pushed him back into the chair, firmly. In a very authoritative voice, she told him exactly what she was doing. "I'm controlling you, little Michelle. Just the way you want to be controlled." She pushed him
on the forehead with her finger, for emphasis, causing him to pull back,
mesmerized by her voice. The "Michelle" thing seemed to do it: he seemed to be almost in a trance, as though he would do anything for her. Melissa reached for the mascara, never breaking her eye contact with him. Her face was serious, but not menacing...she didn't have to be. Michael, or "Michelle", was totally hers. I couldn't believe it. And I couldn't believe I was beginning to get moist between the legs, just watching the scenario unfold before me. By now, I'd finished his toenails and simply sat there, next to his chair, fascinated by what was happening.

"Listen closely, Michelle." Melissa was certainly in her element, now. The tent in Michael's panties had enlarged to incredible proportions, the wet spot growing by the minute...a development not unnoticed by both us girls. "I'm going to apply several coats of mascara to your lashes, so you must hold perfectly still." Michael looked at her intensely, concentrating on every word she uttered, as though she were his goddess. And, in a way, I suppose she was.

His simple response, "Yes, Melissa," was all he said.

I've always been jealous of Michael's lashes...they're long and thick, framing his clear blue eyes wonderfully. I've often told him that such gorgeous lashes were wasted on a guy. I would sometimes tease him and ask him to let me do his eyes. He'd blush and stammer, and politely refuse. Under Melissa's spell, however, he seemed only too eager to be done-up like a horny little tart. And Melissa was doing exactly that. She made sure the mascara wand captured every millimeter of lash, from the eyelid to the very tip. Again and again, the wand combed through his lashes...brush, brush, brush, brush. And again, Melissa kept-up the banter as she worked. "These lashes are absolutely incredible, Michelle," she would say, teasingly. "You should see how full and lush they look with a little mascara. And I think you like having all this makeup on. You do, don't you?" Brush, brush. "You like the way it smells and feels, and you like having me put it on you, don't you...my little slut. Hmmmm? I think I should have you come into the store and see if we can't find you some mascara you can call your very own." Brush. "Wouldn't that be fun! Oh, yes, I do think it would!" Brush, brush. Michael's only response was an intense, libidinous moan.

When Melissa had finished with his eyes, I couldn't believe the transformation. The mascara, liner, and eye shadows made such an impact. It was almost too much, but Melissa had done such an excellent job at blending the color as she went, the look was, well, nothing but glamorous...and very sophisticated. I could tell Michael was a bit taken aback....the mascara made his lashes heavy, almost sticky. Melissa put aside the mascara and turned to me. "Well, Susan, would you like to do his lips and cheeks? Let's trade places!"We did so, quickly, and I retrieved a special shade of blush I had in the top drawer. As I carefully blushed his cheeks, I noticed Melissa take her place very close to Michael's chair. By this time, I was getting quite wet, as I'm sure Melissa was. I was finding it very difficult to concentrate on the task at hand...Michael was just so submissive, yet so exciting, sitting there at the vanity, his face bright with makeup, his pupils dilated. The physical evidence of his excitement, at all levels, was unmistakable, and Melissa seemed intent on turning-up the heat a notch or two. As I added a slightly darker shade of blush just below the first color (to give him the appearance of high cheekbones), I noticed Melissa raking her nails, slowly, deliberately, along the insides of his thighs. Her nails followed a trail up his thighs, pausing momentarily before raking the front of his panties, assaulting the organ they so tightly confined. This elicited another loud moan from Michael as his hips left the seat of his chair, thrusting lewdly as though he were engaged in a most naughty act of coupling. Melissa's voice took on a deep, lascivious tone as she dug her nails ever deeper into the tender flesh of his inner thigh. "Oooh, Susan! I think our little bitch is in heat!"

I was really getting into this! "Oh, yes! I do believe she is," I replied, putting the finishing touches on his cheeks. "And as soon as I've finished doing her mouth, we'll see if she can put it to good use." Actually, I wasn't sure if I could finish, my panties were so wet! I dispensed with lip liner, and went straight to lipstick. "Burning Rose" seemed appropriate, since it matched his toenails perfectly. As I applied the color thickly and heavily to Michael's mouth, teasing him as I went, Melissa continued her assault on his lower quarters. She had freed his organ from its nylon prison, and the sight of it, engorged and purple, contrasted wonderfully with Melissa's slender, pale fingers, tipped as they were with scarlet, her nails gently toying with their newly freed captive. Her pupils, too, were dilated, and seemed transfixed with that which she was so artistically manipulating. Michael was dripping profusely, coating the tips of Melissa's fingers as she worked at her task. From time to time, she would scrape his penis just beneath the head, using all five fingertips, as though she were plucking a plum from a bowl. She would then insert one of her nails into his slit, teasing it and eliciting quite a vocal reaction from him as she tightly grasped the shaft
with her other hand.

I jumped when the doorbell rang, and I thought Michael would absolutely stroke-out! Melissa, however, remained totally calm, pushing him back into the chair and continuing her manipulations. "Why don't you answer the door, Susan, while little Michelle and I continue our business." She didn't miss a beat as she looked-up at him, reasserting her control. "Don't you dare move, little sissy! We have something to take care of, here." She stroked him several times to "convince" him that his best option was to remain were he was.

I straightened myself as best I could, and went to the door, silently cursing. It was Tina, my next- door neighbor and hairdresser extraordinaire (according to her!). Actually, she is very good, working her magic on the beautiful people at a little boutique on Oak Street. She commands top dollar for her colors and perms, and she's well worth it. She does men's hairstyling from time-to- time, but I think the men come to her just to ogle her drop-dead looks and the stylish, revealing outfits she wears. More than one person has compared her to Morgan Fairchild at 23.

I don't even remember, now, why Tina came by. All I know is that Melissa must have done something to Michael to make the earth move for him. We both heard a cry and "Oh, Melissa, you're driving me crazy!!"

Tina, not surprisingly, picked-up on this most obvious outburst of male ecstasy. "Is Michael here? What are you doing?" she smiled, wickedly, doing her best to glance over my shoulder to see what was going on in the bedroom. "Sounds like an orgy or something!"

Then it dawned on me....we'd done his makeup...he'd obviously shaved his own legs and dressed quite....wantonly. Now all that's left was his hair! And Tina would fit the bill, nicely. I led her back to the bedroom, anxious to see her reaction to the decadent display. I was a little surprised to find Michael sitting in the chair, slowly stroking himself, his still-purple member pointing at the ceiling, the pre-come now dripping over his own fingers. He was facing Melissa, who was off to the side, preparing to take a photograph of the carnal image before her. Flash! Before we could say anything, the picture was taken. Now, I knew that Tina was fairly progressive-minded, but I could never have predicted her reaction.

"My, my!" she exclaimed, in a tone both sensual and sarcastic. "What have we here?" Michael started to rise, in a panic, but Melissa anticipated the move and was quick to push him back into the chair. As Tina walked toward Michael and the vanity, she continued her onslaught. "I'll bet you make a pretty picture, Michael. Don't you look cute in your makeup and little outfit!" Tina's hands reached for the bra cups, rubbing them sensually, then using her nails to scratch, much as Melissa had done earlier. "Yes, indeed," she continued, "I think you make a very pretty picture. She stood-up straight, suddenly. "Except for one thing...I can't smell you." She reached for the bottle of Beautiful on the vanity, removed the top, and gave Michael two strong blasts of scent on either side of his throat. Replacing the perfume on the table, Tina stepped back as if to admire her work. "Oh, please, don't let me interrupt you!" she said, in mock dismay. "Michael, I believe you were entertaining young Melissa, here." She winked at Melissa and started to laugh.

I decided to join the fun. "Yes, Michael, show us what you were doing for Melissa. I believe you had things firmly in-hand when Tina arrived!" All us girls had a good laugh over that! And before Michael could regain his composure, Melissa stepped-in to reassert control.

"Go ahead, little girl. Show us how you like to play with yourself."

"Yes, indeed, Michael," I added. Because when you're finished, we're going to have Tina do your hair."

"What a marvelous idea!" Tina exclaimed, barely able to control her excitement at the thought of it all. "We'll take him down to the shop, show him off to the girls, and then do him up properly." It was settled!

I'm not sure what caused Michael to respond so forcefully to that suggestion, but we girls quieted our excitement when we heard him moan and begin to pump himself, furiously. I have to admit, I was fascinated by the spectacle of watching him masturbate...his eyes transfixed on Tina, his hand moving rapidly as he coaxed his release. And what a release it was! He was so vocal. "Ohhhh, please!, Mistress!! Ohhh! Oh! Oh!" His vocal outbursts were nothing compared to those down below, however. Tina squealed with delight as Michael completed his assigned task.

As Michael's release began to subside, Melissa whispered to me, "Let's just pull his clothes over the lingerie, and make him leave the makeup on." A wonderful idea, I thought.

Tina added, "Yes! And high heels, too! He'll make quite an entrance into the shop, don't you think?"

I thought so, indeed. This was going to be much better than an afternoon of shopping!