Mikes Sleepover Part 2
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Mike's First Time free porn video
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
okay."
"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."
Eisley
- 08.08.2022
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