Date: Sat, 5 Mar 2005 01:47:08 -0800 (PST) From: Marcia Fredricks Subject: Mike's First Time Mike poked his head into the narrow opening and peered into every corner of the room as he slowly pushed through the door. Even though he knew the house was empty, he needed to be absolutely sure that his mother wasn't in her room. Mike's mom had left for the weekend several hours before. Mike had kissed her good-bye and watched her drive off. He waited two hours, wanting to be sure that she wouldn't be coming back for forgotten keys or an overlooked hat. He waited another hour and then called her cell phone, just to make absolutely certain that she wouldn't be returning for any reason. "I'm waiting to cross the boarder," she told him. "I'll be across in a few minutes. It's sweet of you to call Honey." The call had cemented it. Mike walked down the hall to her room with his heart pounding. He felt short of breath but nothing would deter him. He was determined. Mike was sixteen. He didn't know exactly what was driving him into his mother's room that day. He had resisted this impulse for years, uncomfortable with the odd desire. But knew he couldn't fight it any longer; he had to confront it head on. He stepped into the room and looked around yet again. He stared out the window, regarding the street, looking for his mother's car, unexpected friends, or deliverymen. Satisfied, but with heart pounding even stronger, he turned to his mother's closet. He slid the door open and inhaled deeply as he took a step into the walk-in-closet to begin a journey that he had dreamed about for years. He began to tingle. The warm sensation radiated out from his groin, spreading all over his body. He gazed at his mother's shoes. There were many pairs. The sneakers and flat sandals didn't interest him. What drew him were the high-heels. He knelt down and gently grasped a black, five-inch stiletto heeled pump. He turned it around in his hand, looking at it from every angle. Mike's thoughts wandered. He remembered being eleven years old and watching his recently divorced mother dress for a date. She was in her panties and bra when he had burst into the room and jumped on the bed. She was thirty-two, with shapely legs and a good figure. Shoulder length chestnut hair framed her pretty face. She had make-up on and her lashes were strikingly long and her lips red, full, and sensual. "What're you doing?" Mike asked. "Getting ready for my date," she answered in a soft sweet voice. She strode to him and shot her hands around his waist. She tickled him and as Mike pulled away she flopped onto the bed. Mike twisted, freeing himself from her grasp and jumped on top of her. They wrestled happily, tickling and giggling. Both fought for breath and the upper hand with Mike finally working his mother onto her back on the bed. He straddled her stomach, his hands pinning her's firmly on either side of her head. Her tits were barely hidden in her sexy "out on a date" black lace bra and Mike watched them heaving as her breath slowly returned to normal. "That's enough honey," she panted. "Let Mommy up. I have to finish getting ready." He rolled off. "Can I stay?" "If you're quite Sweetie." Mike lay on his stomach as his mother returned to the closet. He felt a hardness pressing against his stomach. He slid a hand under himself, to see what he was lying on. There was nothing in the bed. He got to his knees and searched the bed covers, but still found nothing. Then he felt an odd sensation in his pants. He reached down into the front of his jeans and felt a sticky wetness. He realized his penis was hard and stiff. It felt good. His hand slid easily over his wet dick. He momentarily lost himself in the pleasure but soon looked up in a panic. He was relieved to see his mother had not seen him. She was facing into the closet, looking at herself in a mirror. She was still in panties and bra, but now she had added a garter, stockings, and white high-heel shoes. Mike kept rubbing his hand over his dick while he watched her. She modeled the shoes to herself, turning her legs this way and that, rating the high-heels in the mirror before kicking them off and putting on a pair of red ones. Mike continued watching, fascinated, as she checked the effect of the shoes on her legs. Even more fascinating was the sensation in his dick as he massaged it more and more vigorously. His mom kicked off the red heels and reached down for another pair. Her lacey panties rode up and stretched as she bent forward and Mike was astonished to see the clear outline of her ass through the thin material. The feeling in his dick was surging, building to something he didn't understand - but it felt good, too good to resist, too good to stop. His legs began to shake. His mother slipped on a pair of black shoes, the highest and narrowest heels yet. Just as Mike felt that his dick was going to explode, she began to turn toward him. He whipped his hand out of his pants and threw himself facedown on the bed but his dick was out of his control. It had taken on a life of it's own, pulsing and throbbing, even though Mike was laying still, willing it to stop. "Do you like these, Honey?" his mother asked, oblivious to the excitement in his pants. "The red ones are nice too, but I think these show off my legs best." "Ahhh, yeah. They're great Mom," he said pushing off the bed and hurrying to the bathroom. The next time he saw his mother, Mike was sitting on his own bed. He had changed his underwear and was replaying his first orgasm over and over in his mind. He didn't understand it, but it still brought a smile to his face and a tingle to his crotch. His hand would unconsciously wander inside his jeans and he would pull it away as soon as he realized that he was playing with his dick again. She appeared in the doorway looking fantastic. Even a child Mike's age could tell. Her hair gracefully curved around the sides of her face where the ends rounded and curled, highlighting the point on her face where small dimples twinkled between cheek bone and chin. Her black mini-dress was short and tight. Her taught ass looked wonderful under the clingy stretch fabric. Her tits were a lovely sight. The scoop cut neckline exposed the tops of her tits almost to the nipples and their gentle cleavage shone like a beacon. She had been right about the shoes. The black five-inch high-heels did just what she hoped they would - show off her legs and firm her ass. Wrapped in natural color stockings, you could follow the line of her legs from the girlish insteps that hugged the black leather shoes, to her inviting soft thighs that hinted at flaming desire between her legs. "I'm out of here, Sweetie," she cooed. Mike looked dazed. She stepped to him and pressed her lips to his forehead. "Are you alright?" she asked concerned "I'm fine," he answered meekly. "Have a good time on your date. I'm ok." "Thanks, Honey. Be good. Don't wait up." Mike's orgasm had scared him. He didn't know what had happened and he was embarrassed - but not embarrassed enough to stop masturbating. He masturbated regularly from that day on. Often he thought of his mother when he jerked off. He imagined her, as she was that evening, in her panties, bra, and heels. He pictured them wrestling. And he remembered her tits heaving as she gasped for breath. At some point, Mike couldn't remember when, he realized it was wrong of him to fantasize sexually about his mother. So he fought the urge. He forced himself to think of girls in his class. It worked well enough, but inevitably, before he came, all the teen-age girls had magically acquired his mother's panties, stockings, and high-heels. When he was older, Mike and his friends began talking openly about sex. They got together and shared Playboy and Penthouse. Mike liked the women in the pictures but his favorites were never the naked ones. He liked the women who posed in their panties and high-heels. Mike's thoughts returned the present - to the shoe in his hand. He laid it on the floor and held his foot beside it. His dick was already hard, but when he slipped his foot into the shoe, it became rock-like. He steadied himself, one hand on either side of the doorframe, and lifted his other foot. It slipped effortlessly into the second black high-heel and Mike straightened himself. The shoes fit perfectly. Mike marveled at how wonderful they felt. He dropped his hands from the walls and balanced his weight on the narrow heels. There was pressure on his heels and on the balls of his feet. It was noticeable but not uncomfortable. The pointed toes pinched his feet a bit but he liked the feeling. The feeling on his instep was the real pleasure. He felt light and exhilarated - and sexy. Mike looked to the full-length mirror. He loved how his feet looked in the high black heels. It wasn't a rational thought, but Mike knew he belonged in shoes like these. He turned and posed. He checked his feet in the heels from every angle and couldn't find one view that didn't thrill him. He stepped out of the closet and practiced walking. He had no trouble, it felt natural. It felt good. It felt right. His cock was throbbing. He knew he was close to a magnificent orgasm but he didn't want relief yet. He wanted more of this feeling. Mike practiced a swishing walk to his mother's dresser. He knew which drawer held her underwear and he opened it without hesitation. When his fingers touched the delicate garments, he sighed. Mike carried a lacey pair of white panties to the bed and laid them down gently. He looked at them longingly as he pulled of his shirt. Next he lowered his pants and jockeys to his knees as one. He sat and lifted each leg until the toe of each high-heel pointed to the ceiling. Then he slid his pant leg off over the shoes. When he was naked, except for the high-heels, Mike stepped into the panties. He pulled them on and came the instant the nylon covered his dick. Every trace of anxiety disappeared with the orgasm. Mike ceased feeling guilty. He felt renewed; relieved that he was at last on the path he was destined to follow. But, for the moment, the path led him into the bathroom where he pulled the panty waistband away from his body and saw his dick swimming in a large puddle of cum. He swabbed it out with a wad of toilet paper. He rubbed at the stubborn wet patch with little luck. A stain was sure to remain. "I guess these are my panties now," he said to himself with a smile. He let them snap back into place and made his way back to his mother's room. Now he was fearless. He lifted stockings, garter belt and bra from various drawers. Mike slipped his arms through the bra and guided the straps over his shoulders. He reached behind his back to fasten the eyehooks but couldn't bend his arms that way. He tried reaching over his shoulders - no luck that way either. He stopped and thought, and then he slipped his arms out of the straps and turned the bra so that the back was to the front. He clasped the hooks and spun the bra in a circle around his middle. He slid his arms through the straps again and straightened them over his shoulder. He stuffed the C cups with stockings until he felt he had nice size tits and modeled them the mirror. Satisfied with his chest, he snapped the garter belt in place and sat on the edge of the bed. He held up a stocking and tried to put his foot into it. He had trouble working his toes into the opening and when he tried to pull it on too forcefully, the stocking ripped. "That's mine too," he said out loud. He did better with his next try. He was gentler but he still didn't know to roll the stocking and work it up the leg gently. "Now I have a pair," he thought unconcerned. Finally, he got the knack and soon both of the lace-topped stockings were being held tight around his thigh by the garter clamps. When he put the heels back on, the shoes felt even better. They were looser allowing his feet to move ever so slightly in them. Every time he took a step or wiggled a toe, the wonderful feeling of nylon against leather shot up his legs to his crotch. His cock was hard again and Mike ached to jerk off, but there was one thing still to do. Mike's eyes searched the closet for the black mini-dress that his mother had worn that momentous night five years earlier. It was hanging by itself in a small gap away from the other clothes, as if in a place of honor. It called to him. "Here I am Mike. I'm what you've been wanting all these years. Take me." His hand trembled as Mike reached for the hanger and lifted it off the rack. He held the dress to his body and gazed into the mirror. He swayed his hips, checking himself the way he had seen women do in movies. He knew that he was just teasing himself before the inevitable big moment, when he would actually be wearing the mini-dress. He danced around the room, his arm hugging the dress to his waist. He reveled in the heightened anticipation. He felt more sleek and elegant than ever before in his life. Finally, Mike couldn't stand the self-teasing any longer. He guided the zipper down and slipped the dress off the hanger. He held it carefully as he lifted one of his high-heeled feet. He held the dress open beneath his foot and lowered his leg into it. The second leg followed and then Mike began to pull the dress up his body. With a feminine wiggle, Mike slid the dress over his hips, and then over his panties. He pushed his arms through the short sleeves. He straightened his back and the dress fell over his shoulders allowing the C cups to tighten around his tits. He reached behind himself and pulled the zipper up. The dress fit snuggly across his ass and chest. He placed his hands on his hips and spread his legs slightly. Mike delayed looking into the mirror. His senses were screaming at him and he wanted to absorb all the sensations, all the feelings that his new clothes were providing. With his eyes closed Mike pictured himself, "seeing" in his mind what his senses told him existed. He deliberately took stock of all the feelings. His chest felt tight and his tits, extended beyond his chest, announced their presence and demanded attention from the world. His crotch, hot and tingly, had became the center of being and ached for physical contact. His thighs felt confident, strong, and smooth. The legs tapered elegantly into lean calves and then to delicate, narrow ankles that continued to flow, like inviting streams, into his feet which curved gracefully to the breathtaking high-heel shoes that felt like the most natural and alluring part of him. The heels added inches to his height and gave him a lean, statuesque feeling. Every part of him was experiencing something new and different. It was indescribable. Mike had been waiting five years for this moment and he was reveling in it. Mike's hands glided from his hips to his ass cheeks. They were firm, yet soft and so sexy. He pushed his hinds down his ass to his thighs and shivered when the touched his stockinged legs. His hands rolled around to the front and slid up his thighs under the dress. He brushed his balls ever so softly, yet the sparks that touch sent to his dick buckled his knees. Not wanting to cum so soon, Mike returned his hinds to his thighs and then drew them up his body. He brushed his rock hard cock through the tight dress and continued upward until his hands were cupping his tits. He massaged his tits and felt as if they were real. He pinched them, and tweaking the nipples, he began breathing heavy. He began moaning softly and his hips started to gyrate involuntarily. His legs were shuddering. Mike opened his eyes and stared at himself in the mirror. What he saw almost knocked him down. It was a sexy woman looking back at him from the mirror. Everything he had imagined with his eyes closed was true. He had a sexy killer body. His five-inch high-heels shouted that he was a sexy woman, ready willing and able to please the most demanding lover. His fantastic legs were perched over the slim spike heels. They were spread slightly and they invited - no they shouted - a warm, wet, tight pussy is waiting just inches above the hem of this mini-dress. Hands were all over his tits, working Mike into a frenzy. Seeing and feeling the hands all over his new woman's body was causing sensations in his crotch, stomach, and chest that he had never before experienced. Mike released his grip from his tits and pulled up the hem of the dress. He pulled his hard cock out of the panties and balanced on his heels. Thrusting his hips he fucked his hand made slick by pre-cum. In no time he was ready to explode. He took in the entire picture once again and burned it into his brain. He wanted to remember his first time. He wanted to always remember his first orgasm as a woman. Mike kept working his dick and staring at the woman in the mirror with the huge cock. She was a different version of him. It was Mike from the neck up but a female Mike below the neck. "I must do something about my hair," he thought as a tremendous load of cum shot into his hands. Mike spent a good amount of time cleaning up but he did not change the clothes. Instead, he went to the phone and dialed his girlfriend Roberta's number. "Hi Bobbi," he said when she answered. "Yeah, she's gone. Come on over. Oh, can you bring your wig?" He hung up the phone and glided, sleek and elegant, to the living room where he smoothed his dress before sitting on the sofa. He sat and practiced crossing his legs, at the knee, as a woman would. He waited patiently for Roberta; not at all nervous about how she would react. He didn't know if she was going to scream or punch him. He didn't care. Actually, he did care. He wanted her to accept him this way, to become a partner in his femininity. But he was ready for the worst. If she cursed him, called him gay and told everyone at school, he was willing to live with it. His mind was made up. He was going to continue wearing dresses and high-heels. He loved the feeling and would not give it up for anything. All he hoped for from Roberta was a willingness to explore the feelings with him. He and Roberta had been going together for nearly a year. She had sucked his dick and he had fingered her, but they had never fucked. Mike wanted to of course, but Roberta had held him off. When the doorbell rang, Mike went to answer it. As he pulled it open, he backed up and stayed hidden behind the door. "Come in," he said in a high falsetto. Roberta stepped in and Mike closed the door revealing himself. "Oh, my god," Roberta gasped. "Mike what's going on." She was dressed in blue jeans and a sleeveless tank top. She was the same size as Mike - larger actually, when you considered her well-muscled arms and back that rippled under her tight shirt. She had small tits and her hair was as short as a boys. The surprise of seeing her boyfriend wearing a dress and high-heels caused her to drop the blond wig she had been carrying. Mike kept his feet close together when he bent to pick it up. He didn't stoop the way a man would have, he bent at the waist. The mini-dress rode up and stretched tight across his ass. Roberta stared at his very feminine looking ass and legs. "Do you see anything you like?" he asked, still bent over. "Indeed I do," she answered as she slapped his ass, a bit harder than playfully. "You're quite a cutie. What's your name Honey?" "Michelle." "Well Michelle, I'm very glad you called me. I think we can help each other." "I can't wait to get started," Mike said with a broad grin. "Would you follow me?" He led the way to his mother's bedroom, a jaunty swish in his walk. Roberta trailed him, her eyes never wandering from his swaying ass. "Let's get your hair fixed," she said when they were in the bedroom. She fitted the wig in place and tousled it using her fingers as a comb. 'That's very nice," she said when she was finished. "You look lovely." "Thanks Roberta." "Call me Bobby," she said as she leaned in to kiss him. When they kissed, their lips parted and their tongues twirled around each other. Long buried teenage passions were released in a torrent. Their bodies pressed together and Roberta's strong arms wrapped around Mike's slim body and her hands cupped his ass. Roberta pulled him closer and ground her crotch against him. Mike whole body tingled and he sucked Roberta's tongue deeper into his throat. When their lips separated, they were both breathing heavily. "My god," Mike gasped. "You're a good kisser Michelle," Roberta confided. "But I like my women wearing lipstick." She led him to his mother's make-up table, found "his color", and spread the gloss over his lips until they gleamed deep, wet and red. "Now go like this," she said, demonstrating how to pucker. Mike did as she said. "Good. Now your lips look nice a full." She put the lipstick down and searched the table. "Ah-ha," she cried happily. "Eye shadow. You must try some of this. Oh, and mascara, and blush." Roberta was beside herself applying make-up to Mike's face. Mike was a bit lost since he knew nothing about make-up and he just wanted to get back to the kissing. But if it turned Roberta on he was happy to allow it. In about ten minutes Roberta cried, "Finished. Now you really look beautiful. Take a look." She turned Mike toward the mirror. What he saw was astounding. He looked even better. With long blond hair and make-up he really looked like a woman. There was not one hint of maleness in him. Even when he stepped within inches of the mirror and stared hard at his face, all he saw was a woman - and a very pretty woman at that. "Don't I get any thanks at all? Roberta asked. "Oh, Roberta. Thank you. I love it. Thank you so much." He practically leapt into her arms and they embraced like sisters - at first. In a matter of second, they were kissing deeply again and Roberta's hands were all over Mike's body. They kneaded his ass and then slid around his front. Mike sighed as Roberta's fingers brushed his tits. "You have wonderful soft tits Michelle," Roberta whispered. "Oh, rub my tits Bobby. It feels so good." They kissed again and their bodies pressed together. Roberta slipped a hand under the hem of Mike's dress and into his panties. He groaned and his legs shuddered. "Your clit is hard and your pussy is wet Michelle," Roberta teased. "I think your ready to be fucked." Mike came instantly at the thought of Bobby fucking him. "You bad girl," Roberta chided. "You've had your fun but I haven't had mine." She slapped his ass with her free hand. "Get on your knees and suck my dick," she ordered. Mike followed her instructions instantly. He fell to his knees, unbuckled her belt, and opened her pants. Roberta helped him lower her jeans and stepped out of her panties. Mike buried his face in her crotch and began hungrily lapping her pussy. Roberta began to moan. She put both hands behind his head and pulled his face closer while grinding her hip against his mouth. "That's good Michelle. You're a good cocksucker baby," she complimented between deep breaths. "That's it you bitch. Make me cum." Mike licked at her pussy furiously. He was thrusting his tongue in and out, fucking her with his tongue, when Roberta shrieked. "Oh yes, yes, yes! I'm cumming. Oh, Michelle, I'm cumming." Roberta's body stiffened and she became suddenly quiet. She seemed in a trance. She pushed Mike's head away and slowly her breathing returned to normal. "Wow. That was fantastic Michelle." Mike's cock twinged every time Roberta called him Michelle. "I liked sucking your cock," he admitted a little sheepishly. "Good, because you're going to be doing it a lot, she said with a growing grin. "But now I want to fuck you. Get on the bed you sexy girl." Mike climbed onto the bed and Roberta pounced on top of him. She pressed her knees between his legs and spread them. Mike gasped, as his legs were forced apart. She lowered herself onto him and kissed him roughly. She wriggled her body against his and then lifted herself to her knees. Her hand slipped under his dress and she hooked her fingers on his panties and pulled them down. Mike wriggled his ass allowing the panties to slip over his hips. Roberta pulled them out from beneath the dress and slid them off over his high-heels. After dropping the panties on the floor, she pushed glided the hem of the dress up until his cock sprang out. She took it in her hands. "You're such a sexy girl Michelle." Mike whimpered. "I'm going to fuck you 'til you cum." Roberta lowered herself onto Mike's cock and began to glide up and down, swallowing his cock with her pussy on every down stroke. Soon her rhythm was furiously fast and Mike's moans of pleasure mixed with Roberta's grunts of exertation. She slowed the pace of the up and down pistoning and replaced it with hard crotch grinding. "Fuck me Bobby. Fuck me harder," Mike yelled passionately. "Cum for me Michelle. I want to make you cum," Roberta shot back. "Yes. Oh god, yes. I'm cumming." Roberta was thrusting fiercely now, throwing her body forward and back with exuberance. She felt as if she were ramming her stiff cock into Mike's wet pussy as powerfully as a jackhammer. Mike too, had lost track of whose cock connected them. It was easy for him to believe that the intense thumping between his legs was Roberta was fucking him. It was in this mixed-up state of mind that Mike and Roberta both came as never before. With huge spasms and animalistic shouts their bodies shuddered. Roberta kept pounding and grinding, forcing her cock into Mike as deep as it would go. At the end of her powerful orgasm, Roberta went rigid and both lay seemingly frozen, enjoying the last of the tremors that shot through their bodies like trapped lightening. The buzzing shivers ran up and down their muscles before tapering off and finally stopping. Roberta collapsed on top of Mike and they lay still for a long time. "I have to get home," Roberta said after a very long silence. She rolled off the bed and began dressing. She lifted Mike's panties off the floor and held them out to him. "Put your panties back on." Mike stood and stepped into the panties. "I want you to stay dressed like this for the rest of the day," she said seriously. "I like you this way." "I like it too," Mike admitted out loud, but thought to himself, "I'd like to stay dressed like this forever."