Three Cheers - In the Bleachers
Author's Note: In Three Cheers for Freedom Diane got Zach to dress up
as a cheerleader for her. I started wondering if maybe someone else
might get the idea from seeing Zach. This story came to me.
Cheryl was lost in the sensations racking her body. Her eyes were
closed tight, not for fear of opening but because she just couldn't
open them yet. Slowly the tingling began to subside; she was starting
to make sense of the world again. She became aware of the hand resting
on her bare thigh, realized she still held the now soft penis of her
boyfriend in her own hand. She blinked her eyes letting the world come
back into focus, not that there was a lot to see, the lake beyond the
car was too dark to see much of anything. There wasn't a moon this
evening.
Don started to move to get something to clean up. She waited, still
gently holding him, her fingers were a sticky mess and she didn't want
to drip anything. This was just the second time they had done this. Up
until a few weeks ago they had behaved somewhat properly, she rubbed
his erection over his jeans; he would squeeze her breasts or rub her
pussy over the clothes she wore while they made out. Then she wore a
skirt for a date. He reached under her skirt and next thing she
realized she was desperate to undo his pants and hold him in her hand.
She was surprised at how messy it was when he came. This time he was
prepared.
He handed her a soft paper towel from a roll he pulled from the back
seat. She carefully took her hand away and started wiping off the
sticky goo. Then she took another and cleaned her own thighs which
weren't near as messy as Don's. She dropped the towels into a plastic
bag that was hanging on the gear shift as a make-shift trash bag then
proceeded to put herself back in order. She slipped her boobs back into
her bra and then pulled her blouse back down. She reached down and
found her panties still wrapped around one ankle. She put her other leg
through the hole and pulled them back up into place then pulled her
skirt, which was bunched around her waist, back down and tucked it
under her. As she was finishing up she heard the click of Don's belt as
he finished buckling it.
Don grabbed the trash bag and left the car, walked a few steps to a
trashcan near a public bathroom by the parking spot they have been
using since the summer before their junior year and dropped it in. He
climbed back in the car and pulled the door closed.
"Wow," he leaned back in the seat, "I think that was even better than
the first time."
"Well I think we both knew where this was going as soon as you picked
me up and I was wearing this skirt," Cheryl answered. "Last time I
think we were both caught by surprise and I think I was waiting to see
if you were going to stop me, and I wasn't sure if I was going to stop
you."
"I definitely wasn't going to stop you," Don laughed. "I've wanted you
to do that for a while."
"The genii is definitely out of the bottle now, but I don't know what
happens next. Right now I'm happy with doing this, as long as we don't
get caught."
"I think it is dark enough out here that if another car comes along
you'll have time to pull your skirt and blouse down. And I can get my
pants pulled back up," Don tried to reassure her.
"I hope we never have to test that theory," Cheryl sighed. "You want to
go get a coffee at Denny's?"
"Sure, "Don reached for the key in the ignition and turned it. Lights
bloomed inside and outside the car though the headlight still didn't
show them much beyond a dark expanse of water.
"Maybe Beth will be there," she stated. "And Jake," she added after a
pause.
"Maybe," Don answered as he backed out onto the road. "You don't like
Jake much, do you?"
"Oh, he's ok," she answered. "I just don't know him all that well yet.
Beth's my best friend but I know she can get a little crazy and I think
she needs someone a little more grounded. He might not get her into
trouble, but I don't believe he'll prevent her from it."
Don drove them back toward town, a twenty minute drive that they took
in silence except for the music on the radio. Cheryl thought back over
the evolution of their relationship. She and Don became friends in
their freshman year after finding themselves sharing three classes. Don
was joining the band and she was trying out for the freshman dance
team. They started dating without really trying in their sophomore year
and by mid-year they were considered an item. Many high school
relationships come and go but they stayed together. Now in their senior
year they had graduated to seeing and touching each other's naked body
and parts they hadn't considered. She worried that this might be the
beginning of the end, so many other couples at school broke up after
having sex but they weren't having sex, not really, not yet.
She cringed a bit as the thoughts of breaking up came unbidden. She
loved Don. He was sweet and kind. He always treated her with respect
and never forced her or even made her uncomfortable about wanting to do
something she wasn't ready for.
Don piloted the car into a parking space at the Denny's and they
climbed out. Cheryl double checked herself making sure her skirt wasn't
caught up and everything else was where it ought to be.
They walked in and were immediately ushered to a booth along the big
front window. Cheryl held her skirt as she scooted in close to the
window, Don slipped in beside her. They both ordered coffee.
Before they could start talking they heard a noise and looked out the
window. Beth was outside with Jake in tow. They had been dating since
the beginning of summer. Cheryl waved for them to come inside and join
them.
Beth walked up in torn jeans and a t-shirt, Jake followed, his jeans
untorn. She slid across the booth to sit across from Cheryl Jake
dropped in and put his arm around her.
"What have you guys been up to tonight?" Beth started right off.
"Oh, nothing much," Cheryl answered but she could feel the flush coming
on. She knew she wasn't any good at lying. "Just stopped in for
coffee."
"And I'm betting a trip out to the lake," Beth smirked.
Cheryl declined to answer but she could see she didn't need to. Instead
she decided to change the subject. "I was just about to talk about next
weekend with Don. No Varsity game next Friday so no band or dance team,
but Ms. Duncan wants us to show up for the powderpuff game the
cheerleaders put on to show support. Have they said anything to the
band?"
"No, but if you have to be there I'm happy to go," Don answered. "It
will actually be nice being able to sit with you instead of in
different places."
"I've got to be there, too," Beth answered. "We can have a good time if
we all get to sit together. You okay with that Jake?"
"Sure," he squeezed her. "Then maybe we can find something to do after.
Like maybe the midnight movie? I think they are going to play that old
Flash Gordon movie next weekend, the one with the Queen soundtrack."
They all nodded about the idea and went on talking about other things.
Mostly Cheryl and Beth talked while Don and Jake carried on their own
conversation.
A week later the four of them were sitting about three-quarters of the
way up the bleachers all dressed in jeans and light jackets since the
weather was turning a little on the cool side.
"Who is that?" Cheryl asked looking at the cheerleader bouncing around
near the field. "That's a guy and not one of the football jocks."
"Oh, yeah, that's Zach," Beth answered. "You know, Diane's boyfriend. I
heard him explain in class that she wanted a serious cheerleader
because they were serious about the game. You know how she is. All rah
rah school spirit like it would be the end of the Earth if you didn't
know the school song, or didn't give 100% to rooting for the team. Some
of the jocks, and a few others, were giving Zach a hard time but he
just let it roll off. I don't know him but he seems like a good guy."
"Oh, we ought to go down there and give him some shit," Jake leaned to
tell Don.
"Don't you dare," Cheryl told Don hoping it would carry over to Jake.
"The guy is just trying to be supportive for his girl. I think it's
sweet."
"Well I know I'd need to be convinced," Jake continued. "What do you
think he is getting for walking around all day in that skirt?"
"Nothing," Beth answered. "Diane is a good girl, doesn't do anything
that she shouldn't. Her friends are jerks though. I bet Zach gets the
short end of the stick on this deal before Christmas."
"Don't say it!" Cheryl pointed at Jake as he was about to make a
comment. "I don't know what you were about to say but I don't think it
would have been nice. You should just leave the poor guy be."
"You haven't said much, Don," Beth pointed out.
"I don't know what to say about it," Don answered. "I mean it sounds
like she asked him to do it, and I remember him from Junior High and he
was always a loner. The fact that he is even with her I think he'd do
anything to try and keep her."
"So, are you saying there are limits to what you would do for me?"
Cheryl asked.
"Um, gee, I, um," Don stammered trying to figure out how to answer.
"Well, I think there are things I would have to say no to. I mean if
you asked me to kill someone, or steal something, I would have to say
no. And there're probably other things, so yeah, there are limits."
"I see," Cheryl moved a little away from Don teasing him, pretending to
pout.
"Damn straight there are limits," Jake answered.
"You say that because we haven't been going out that long," Beth
answered back. "You've probably already started scouting for your next
girlfriend."
"Oh, you hurt me," Jake answered. "I am only thinking of you."
They leaned together and kissed.
Cheryl reached over and took Don's hand. They sat and watched the game
unfold. About halfway through the game Beth leaned over and whispered
into Cheryl's ear.
"I have an idea," she began. Then she mapped out what she had in mind.
Cheryl turned and whispered back, "Are you sure? Do you really want to
do that?"
"Oh, I think it would be fun and we'll see just how far those limits
go."
Cheryl nodded but still wasn't sure. She figured she'd have some time
to think about it, it would still be a few weeks away.
Chapter 2: Weekend Away
"I can't believe you got your parents to agree to let us close up the
summer cabin this weekend," Cheryl exclaimed as they walked to Cheryl's
car.
Oh, it really wasn't that difficult," Beth bragged as she got behind
the wheel. "I just explained how I really needed to spend some time
with my best friend since it was our last year together, and that
closing down the cabin would be a good opportunity for that. Besides,
it would only be for one night since we had to perform at the game last
night."
"Yeah, well I bet you might have left out that tiny little detail about
Don and Jake coming with us," Cheryl smirked.
"Did you tell your parents?" Beth accused.
"They didn't ask," Cheryl side-stepped.
They both cracked up laughing as Beth drove them away.
Beth drove to another spot, not near either of the boy's houses where
they awaited the girl's arrival.
Cheryl got out, struck a sexy pose and then wrapped her arms around Don
when he reached her. "You excited to be able to spend a night with me?"
"Absolutely," he squeezed her tight, "I didn't expect anything like
this to be able to happen for a long time."
"Who knows?" Beth called from the other side of the car. "Maybe you'll
get to do more than give each other hand jobs."
"Wha??" Don sputtered and turned scarlet.
"Sorry," Cheryl shot Beth a dirty look. "I didn't think she would
actually say anything out loud like that. But you ought to know we talk
about everything."
"Come on, let's get going," Beth directed. "We have a long drive and I
don't want to get there too late."
Jake climbed into the passenger seat, Cheryl and Don got in the back
and Beth started them off down the road for their weekend adventure.
The cabin was near a small town and Beth didn't want to be seen in a
store there with the boys. Small towns have long memories and the last
thing she wanted was one of them saying something to her parents next
spring about the four of them picking up groceries. So they stopped
further away and got a couple pizzas for dinner and some things to eat
in the morning. The sun was just starting to reach the tops of the
trees when they pulled up to the cabin.
Cheryl climbed out of the back seat and stretched. She looked around
and couldn't see another building outside the cabin that stood in front
of them. To call it a cabin was an injustice, it had the look of a
cabin but inside it was a comfortable living space that included a
kitchen and dining area. Then there were two bedrooms for privacy. She
was looking forward to the game she and Beth planned and then spending
a night snuggling with Don under the covers. She still hadn't decided
how far she was going to go but even if they just made out and
masturbated each other, it would be great being able to just get
completely naked and not worry about another car driving up.
"Let's get in, get our stuff put up and get these pizzas in the oven.
I'm hungry after that drive," Beth announced. They all agreed.
"We'll take this room," Beth walked toward one of the doors off the
main living space, "you guys can have that one. There is only one
bathroom so we'll share. I hope you guys aren't slobs, I know Cheryl
isn't."
Beth turned and carried her bags to the bedroom indicated.
"Why do you have so much stuff?" Don asked. "It's just one night; I got
everything in this shopping bag."
"It's a surprise," Cheryl answered. "Go see about getting the oven
turned on, I need to put some things away. I'll be out in a minute."
When Don left the room she opened the garment bag and pulled the two
dance uniforms she brought. She hung them both in the small closet then
checked the rest of the clothes in her bag. She'd brought a little
nightgown just in case she couldn't go through with sleeping naked with
Don. Satisfied, she went out to join everyone again. Don and Jake were
in the kitchen putting the pizza in the oven; Beth was just emerging
from the other bedroom.
"I have the first surprise," she announced. "I was able to get some
beer and a couple bottles of wine. I know Cheryl doesn't like beer but
will partake of the grape on occasion."
"You didn't tell me anything about beer and wine," Cheryl turned to
Beth.
"It was a last minute thing," she answered, then whispered, "it will
help things along later."
She watched as the boys immediately dug into the fridge and located the
beers. They each popped one open and began taking a swallow.
"Cheryl," Don asked, "would you like some wine now?"
She thought about it for a bit. She really didn't want to get tipsy and
lose control. "I think I'll wait until after I eat something."
"OK," Don turned away.
"Not going to ask me?" Beth called out.
"Oh, sorry," Don looked at Jake who was still just standing there with
his beer in hand. "Would you like some wine? Or a beer?"
"I'll take a beer, thanks," she answered.
Don took the beer to her then sat with Cheryl at her end of the couch.
It was a long curved couch with a large hassock in the middle. Beth sat
at the other end. Jake finally found his way back to the couch. He
plopped down and tried to kiss her.
"Just slow down," Beth admonished him. "We've got all night."
Cheryl didn't want the talk to go toward expectations of the rest of
the evening so she directed it toward things going on at school. They
talked until the timer went off and they pulled one pizza from the oven
and put the second one in. Cheryl relented and took a glass of wine to
sip on while they ate.
An hour later the sun was now completely down, they had finished off
the pizza. Cheryl was almost finished with her first glass of wine; the
other three had already knocked down a couple beers each.
She looked at Beth, Beth nodded back. "You boys get cleanup duty. There
isn't a dishwasher so you are the dishwashers. They all need to be
cleaned up and put away. Remember, when we leave tomorrow this place
needs to be locked down for the winter. No loose crumbs or anything for
critters to want and set up shop here, ok?"
"Sure," Don immediately jumped up and headed toward the kitchen.
"OK," Jake stood, burped, and followed Don. He stopped, "what are you
girls going to be doing?"
"We are going to get ready for the next surprise!" Beth answered. She
grabbed Cheryl helping her off the couch and they went off to their
separate bedrooms.
Cheryl walked in and opened the closet door. She then turned and
stripped down naked. Typically she would wear a bra and nylons with
this dance outfit but tonight was special. She and Beth had agreed this
was going to be a sexier night.
She pulled a pair of red sequin shorts and slipped them on. The waist
was high and came to her navel. The legs were very short. After that a
short tuxedo jacket with long tails. The lapels matched the shorts with
the sequins, the sequins then continued to line the edges around the
tails in the back. Last was a fake ruffled blouse. The collar attached
behind her head, and then it snapped into place on the inside of the
jacket. The jacket had two buttons closing the jacket on top of the
shorts. She looked in the mirror, turned and bent over a bit. The
sequined shorts flashed through the split in the tails which reached
her knees, from the front the top of the shorts couldn't be seen but
the bottom half were clearly visible.
She stopped and hastily put on her show make-up: heavy eye-shadow,
mascara and lipstick. She checked her phone for the time and saw it was
almost time to head out. She and Beth had agreed on how long it would
take them to get ready and would come in at the same time. She walked
to the door and waited for the minute to change one more time. It
clicked over and she walked out, she saw Beth come out at the same
time. They smiled at each other.
"Oh, yeah!" Jake called out. "Now that's what I am talking about."
"You girls look great," Don agreed. "Usually I'm too far away to get to
see you in full dress mode."
"Well, we are going to give you a little show," Cheryl told them.
"Right, so sit down there on the couch and enjoy," Beth finished.
Cheryl set her phone to play some music, and then on the beat they
began their dance routine. They stepped and kicked and turned and bent
over letting their glittery butts stick through the tails giving them a
wiggle to the boys on the couch.
Cheryl thought how strange to have a small personal crowd to perform
to. She could see the effect it was having on Don; he was squirming a
bit trying to adjust himself without giving away what his problem was.
The music ended and they finished their dance standing back to back,
arms folded beneath their breasts, breathing hard.
Don was first to offer applause, Jake quickly joined in.
"That was great!" Don told Cheryl as she came over.
She swept her tails back and sat on Don's lap. He wrapped one arm
around her and laid his hand on her bare thigh.
"Glad you enjoyed that," Beth took a similar position on Jake's lap.
"So, now it's your turn."
"Huh," both boys looked confused.
"Yeah, after seeing Zach do his cheerleader thing, and you boys talking
about him we thought it might be fun to have you do a dance routine for
us," Cheryl explained. "We brought our other uniform for you to wear.
You can go in the other room and change then come out and give us a
show. We'll give you some extra time to work something out. It doesn't
have to be long, or even all the good, but you have to try."
"Look at it this way, at least you don't have to do it in front of the
whole school, just us," Beth added.
"What if we'd rather just skip the uniform," Don asked. "Y'know, we
could work up something for you but..."
"What if we just skip the whole thing," Jake added.
Beth and Cheryl both stood up, they had expected resistance.
"Fine," Beth answered. "It's your choice."
"By the way," Cheryl told them, "I hear this couch is pretty
comfortable. You don't do this; you get to sleep out here."
"You're kidding, right?" Don asked.
Cheryl shook her head.
"This is fucked up," Jake protested.
"It's just like it was for Zach," Cheryl explained. "You don't have to
do anything. We just want to see if you would do something for us
because we want it. We aren't asking you to kill anyone or steal
anything. Just a little dance to make us feel special."
"I'll do it," Don stood up. "If you really want me to do it. And not
just because I don't want to sleep on the couch, but because you want
me to."
"Dude!" Jake protested. "Why are you caving so fast?"
"Because I did say I'd do anything and while I didn't think it would
come to this, if it is something that she wants, well it won't kill
me." Don started toward the bedroom and stopped. "Just promise me you
don't have some strange idea about making me go somewhere or do
something else."
"Promise," Cheryl told him, "you won't need to leave here and we'll
both be cozy in that bed together later on."
Don nodded and disappeared through the door.
"Jake?" Beth prodded, "am I going to be sleeping in that bed all alone
tonight?"
"You would seriously make me sleep out here?" Jake answered.
"To be honest," Beth answered, "if it were just you and me here I would
probably give in. I think this is going to be fun and because it
wouldn't be fair to let you off the hook, I'll just have to suffer
sleeping alone. But don't worry, I can take care of myself. Just would
have liked for you to take care of me instead, and of course, me take
care of you."
Cheryl could see the shift in Jake's jeans. He was getting a hard on
and wanting to ignore it.
"Shit," Jake stalked off to the other bedroom and shut the door behind
him.
"Actually, that was easier than I thought it would be," Cheryl told
Beth.
"If Don hadn't given in so easily we might still be trying to talk them
into it," Beth recognized. "He really loves you and wants to do
anything he can for you."
"I know, he's a special guy," Cheryl sighed and collapsed back against
the sofa. "I thought they both might come out after looking at the
uniform we left them."
"I know," Beth laughed, "they might have preferred these tuxes but
their balls might have fallen out the bottom of the shorts."
"The panty on those are even shorter," Cheryl pointed out.
"Yeah, but they are tighter so they don't gap and show," Beth went on.
"True," Cheryl looked over her shoulder wanting to see Don come back.
Cheryl was halfway through her second glass when the bedroom door
finally opened. Don walked around the sofa to stand where the girls
could see him. He was all in white, short white skirt with wisps of
tulle peeking out around the hem, a white long-sleeved blouse with a
ruffle front and a bow at the collar. Last a white vest.
"Oh, you look so cute!" Beth called out.
Don blushed and ducked his head.
"Don, you really do look good in that," Cheryl assured him. "It looks
like it fits pretty good."
"The vest is a little tight around my arms. The skirt seems like it is
too short," he pushed at it trying to lay it flatter.
"You aren't a cheerleader, you're a dancer," Cheryl explained. "The
skirt has all the tulle to make it short and stand out some. That's why
you also get to wear the white satin panties. Because when you do your
kicks, or bend over they are bright and shiny. All the boys love
looking at them when we are doing our dances, don't they?"
"Well, yeah, I guess," Don answered.
Jake emerged and joined Don in front of the couch. He had dark hairy
legs that clashed against the pristine white uniform but the girls were
supportive of his look.
"Sorry, I thought it would be enough but I think they need make-up,"
Beth opined.
"What, no!" both boys argued.
"Look," Cheryl pointed out, "how much more is it now that you've gone
this far. I think you'll appreciate what we go through even more. And I
promise, that is the last thing. Then you do your dance and we'll let
you clean up."
Don nodded, Jake saw him nod and threw up his hands knowing he was
beaten without a fight.
Cheryl went back to her room and brought back her make-up.
"Sit here," she told Don, "I promise, I am going to do the same job on
you that I do on myself."
"Is that supposed to make me feel better?" he asked.
"Well, I guess I thought it could," she explained. "Imagine what I
could do if I wanted to make you look really silly."
"You don't think I already look silly?" Don answered.
"Actually, no," she snickered. "I wasn't sure how I was going to feel
about this but I'm actually liking it. Now sit still a minute."
She worked on his face doing a similar job on his eyes and lips. When
she finished she leaned forward and gave light kiss on the lips. "You
look great."
The boys talked for a couple minutes, picked a song and started the
music. They pranced back and forth, tried to do a couple kicks, turned
their back on the girls and bent over so the skirt rose high showing
their butts.
Cheryl laughed and grabbed onto Beth during the performance as they
both laughed and clapped, the butt shot had them both gasping as the
panty was showing it was holding something more than usually found in
them.
The boys finished the dance and the girls applauded.
"Come here," Cheryl called to Don and patted the couch beside her. When
he sat she leaned in and gave him a big kiss.
"I don't know about you Cheryl, but that got me all horny," Beth
stated. She had stopped Jake in front of her and had her hands up under
the back of his skirt.
"Are you saying you are heading to bed?" Cheryl asked surprised. She
thought they would be up longer before heading to the bedrooms, but
also admitted to herself she was feeling very frisky at the moment.
"Screw that," Beth pushed Jake back a little. "I want it now." Without
waiting for anyone to react she reached up and pulled her shorts off.
"Damn!" Jake spoke standing looking down at Beth's exposed pussy.
Cheryl shook her head trying to clear it of what just surprised her,
then gave Don a little shove because he was also staring at Beth's
crotch with its small patch of dark hair and framed by the sequined
jacket.
Don looked away clearly embarrassed to have been caught staring.
"Jake, you get on your knees and do me right and I promise to return
the favor." Beth spread her knees further.
"I like the sound of that," Jake answered. He got down on his knees,
his skirt swishing back and forth as he moved.
Cheryl watched as Jake lowered his mouth onto Beth's pussy and he began
licking and sucking. She wanted to ask if they had already been doing
that but Beth didn't look too receptive of questions at the moment. Her
eyes were closed tight, she was arching her back, she reached out and
grabbed Jake's hair and mashed his face against her. Just when she
thought she should pull Don to the bedroom Beth opened her eyes and
looked at them.
"Cheryl, gets those shorts off and let Don do this for you, believe me,
you won't regret it. Don, if she hesitates get down there and pull,
oooohhhh, pull those shorts off her."
Don sat their stunned for a moment. Cheryl thought and then decided to
go for it. She wasn't sure about getting naked in front of Jake before,
hadn't even thought about it, but suddenly wanted to join Beth in her
bliss. She reached up and pulled the shorts off tossing them onto the
arm of the sofa.
"You gonna just sit there or you gonna do what she said?" Cheryl asked
Don.
He slid off the couch and Cheryl watched as his lipstick coated lips
made contact with her pussy. She groaned as his tongue parted her lips
and caressed her clit. Her eyes closed and refused to open as Don
started getting comfortable with his task. His mouth was giving her
pleasures his fingers were unable to do. A moment later she heard snaps
being rapidly undone. She forced her eyes open and saw Beth had pulled
the fake blouse from the jacket, her boobs now exposed. She looked down
between her legs and saw Don looking over at the sound, taking in the
vision of her breasts. He glanced back and let his eyes close, the
sight of his made-up eyes enflamed her even more, all inhibitions now
lost. She reached up and undid her collar and pulled it loose baring
her tits to the air.
She had already reached her first orgasm but felt a second one building
quickly. She let Don continue, he seemed to be a natural at it. She was
just starting to climax again when she felt a hand grab her wrist. She
looked quickly and saw Beth had grabber her arm, her face contorted
into something that looked like pleasure and pain. She cried out.
Cheryl couldn't hold back any longer and moaned loudly as she came
again.
She collapsed back and pushed Don's head up away from her tender twat.
"Come here," she whispered.
Don got to his feet and moved to snuggle beside her. The stiff skirt
slid along her thigh as he sat, the vest fell open and lay across her
nipple.
"Baby," she turned and ran her fingernails inside the vest looking for
his nipple, "when I recover, I hope I can do half as good a job for you
as you did for me."
"Girl," Beth muttered from beyond Don. "If you get it in your mouth
he'll be thrilled."
Don grunted his disapproval at her crassness.
Beth moved and pushed Jake back on his back. She reached up under his
skirt and pulled the panties off him. Now it was Cheryl's turn to get
caught staring. So far, there was nothing to see, the skirt was still
covering him, but Beth wasn't wasting any time. She pushed the skirt up
exposing his hard cock. Cheryl had only seen Don's prick before and was
comparing them without realizing it. Jake seemed to be a bit longer
than Don but not quite as thick. She wondered if it made much
difference.
Don cleared his throat and turned away. She broke off her stare and
turned her attention back to Don.
She eased her way to the floor and positioned herself at his knees. She
ran her hands up and down his thighs not yet reaching under his skirt.
Then she slid one hand further up until she encountered the panty. She
rubbed the front feeling the hard cock nestled inside. Don groaned a
bit as she slid her fingers up and down his shaft. She suddenly had a
picture of him erupting inside the panty and decided it had to come off
now.
She leaned in with both hands and pulled the panty down and off his
legs. She couldn't resist peeking over at Beth as she moved to position
herself between Don's legs. She watched Beth as she licked the shaft
and then plunged her lips down over the top taking the rod deep into
her mouth.
"This is obviously not her first time doing this," Cheryl thought to
herself.
She slid forward and reached up under the skirt and felt Don's
familiar shaft. She fondled it for a moment. "Hold your skirt up out of
the way for me," she instructed Don. She saw his shaking hands take
hold of the skirt and pull it up, then took more of the tulle out of
the way until his cock was fully exposed to her. She licked her lips in
anticipation and leaned forward. She hadn't had her face this close to
his dick before and she took a moment to look it over while rubbing it.
She reached her tongue out and touched it about mid-shaft then licked
up to the tip. She felt him shudder as she progressed. Emboldened by
his reaction she let her mouth engulf the tip. She probed at it with
her tongue and sucked gently. She felt Don trying to push his hips up,
trying to drive himself deeper into her mouth. At first she wasn't sure
she could do much more without choking but dared to take a little more.
She bobbed her head a couple times and pulled it free. She licked the
sides and kissed his balls, stroking him lightly.
"You better make sure he's in your mouth when he comes," Beth told her.
"What?" Cheryl stopped. Beth had finished Jake off and was lying with
her head on his chest watching.
"Same as the panties, girl-friend, going to be a bitch to clean if he
gets his stuff on that skirt. And those things are a bitch to aim," she
giggled.
"I didn't think about that," Cheryl licked at her lips trying to
determine which direction she was willing to go. She felt Don slowly
undulating his hips fucking her hand. She thought about what he had
just done to her and made her commitment. She turned and directed his
cock back into her mouth. She heard him immediately gasp and a groan
followed.
She stroked the base and sucked and licked. He thrust harder trying to
reach the back of her throat but she managed to keep from choking.
Suddenly her mouth was full and she swallowed before she even thought
about it. Another load flooded her mouth and she felt some leaking
through her lips and onto her hand but swallowed the rest. One last
pump and she felt his body collapse back.
She let his cock leave her mouth and saw just a few drops escaped her
mouth. She wiped at some that had stuck to her chin and sat up. She
looked around for a napkin left over from dinner.
"Just lick it off," Beth told her, "you swallowed a lot more than that
a second ago."
"Um, no, I just can't," Cheryl answered. She spotted a napkin and wiped
off her hands and mouth. She handed it to Don so he could clean up
anything he felt he needed to.
Now that the excitement was over she was feeling self-conscious about
being nearly naked with Beth and Jake. It seemed ridiculous after
spending the last hour having sex in the same room but she wanted to
put something on. She considered the shorts and blouse but decided she
wanted something else. She excused herself and went to the bedroom.
She grabbed a pair of pink nylon panties with white lace trim and
slipped them on. Then she grabbed the nightgown she brought. It was
also pink and it was barely long enough to cover her butt but it made
her feel better. She went back to join the others.
When she got to the couch she saw nobody else had bothered to change.
Noting the panties were missing, she assumed Don had put them back on.
Perhaps he didn't bring any night clothes with him and had nothing to
really change into.
"So, what did you think of you first oral experience?" Beth asked them.
"What do you expect me to say to that?" Cheryl asked.
"I liked it," Don surprised Cheryl by answering. "I really enjoyed
going down on her, and her mouth on me was incredible."
"You really like eating pussy?" Beth asked. "Most guys only seem to do
it if they know they will get blown after."
"Yeah, I liked it," Don confirmed.
"Well, fine," Cheryl relented. "Don, you're a natural at eating pussy,"
she looked at Beth as she emphasized the term. "I could have let you do
that all day. And I was surprised that I enjoyed going down on you
too."
"My, my, I think somebody's life may have changed," Beth grinned.
Jake started snoring.
"I swear, men after sex are just useless," Beth answered.
Don pulled Cheryl closer and kissed her.
The three of them talked for a while longer then decided to head to
bed. Beth roused Jake and they watched as he trudged off to the
bedroom, his skirt bouncing as he went.
Cheryl and Don walked into the bedroom. Don began stripping off the
uniform. Cheryl sat on the bed thinking about how she was going to be
sharing a bed with someone for the first time. She considered getting
undressed again but decided she'd rather stay dressed as she was. She
pulled back the covers and crawled into bed.
Don finally stripped off the panties and crawled naked into the other
side. Cheryl turned to face him as he crawled in.
"That's ok," she answered. "I was just feeling really exposed and had
to put something on. I hope you aren't disappointed."
"Not at all," he reached around her and pulled her nightgown up enough
that he could grab her ass. "I like the feeling of your panties on your
butt."
Cheryl snuggled close and closed her eyes. She drifted off to sleep.
The next morning she woke up. As usually happened, her nightgown had
ridden far up her body during the night. The unusual thing was Don had
his arm draped over her and was holding her breast. He was still
breathing deeply sound asleep. She reached back behind her and felt
around for his dick. She found it and began gently working it in her
fingers. It woke up in a hurry and became stiff in her hand, a moment
later Don started waking up. She felt his hand tighten on her breast
and let out a groan as he realized how excited he was and what she was
doing.
"I have an idea," Cheryl told him. "Lay back."
Don reluctantly released her breast and rolled onto his back.
Cheryl threw the covers back and sat up on her knees. She pulled her
nightgown off and tossed it over in the corner. Then she moved to
straddle Don.
"I'm leaving my panties on because I don't want any accidents," she
explained. "I think this ought to feel pretty good anyway."
She positioned herself on his cock and began rubbing herself up and
down his shaft. Her panties were already wet from excitement and she
slid easily up and down. She could feel his cock against her clit as
she moved and it was rapidly bringing her to a climax.
She leaned over Don working her hips, watching his face to see if he
was getting as much enjoyment as she was getting. It certainly appeared
he was. He kept blinking his eyes, biting his lips, glancing down
watching her boobs swaying back and forth over him. She watched as he
grabbed one tit, leaned forward and sucked on the nipple. She jerked
and felt his cock poke her between her legs. She thought if she hadn't
still had the panty on he would likely be inside her now. She briefly
entertained the idea of taking them off but then moved back to riding
up and down keeping it trapped between her soaked panties and his body.
He started gasping, unable to catch enough breath to suckle her any
longer. Then she felt him coming, saw some of it splashing on his chest
between them. Then her orgasm struck. She tried to drive herself down
hard against his cock and eventually weakened.
He wrapped his arms around her and pulled her down onto him. She felt
the ickyness squeeze between them but chose to ignore it. They lay
there together for a few minutes.
"I think we need a shower," Cheryl finally spoke.
"You want to take one together?" Don asked.
"Why not? I don't hear anyone else up yet."
They got out of bed, grabbed clean clothes for the day, snuck from
their room to the bathroom and closed the door.
They bumped and slipped and played and washed in the shower. When done
they climbed out and got dressed, brushed teeth. When they emerged Jake
and Beth were sitting on the couch.
"Well, at least you made it easy to decide who's next," Beth told them.
"Sorry," Beth answered, "nobody was up when we got up."
"No problem, we just got up," Beth answered. "I'm going first, we'll
pack up and check the place over while Jake is cleaning up, then we'll
clear out, ok?"
"Sounds good, we can put together breakfast while you clean up," Don
answered.
A couple hours later they were back on the road.
Chapter 3: A Visit With Beth
Cheryl knocked on Beth's bedroom door and waited for her to call her
in.
"Hey," Cheryl called as way of a greeting. "What have you been up to?
Haven't seen you in a few days." She pulled off the jacket she was
wearing and tossed in on the footboard. She moved around to sit on the
bed. She was immediately concerned because Beth was sitting at her desk
still wearing a long t-shirt that she slept in and it was already late
afternoon.
"Haven't felt like getting out much," Beth sighed. "Jake dumped me."
"What? Why?"
"He said he wanted to be free during his senior year and not tied down
to one person," she groaned. "Oh, but he said we could still go out
sometimes."
"Hey girls," Beth's mom called from somewhere else in the house. "I
need to run a couple errands. Be back in a couple hours."
"OK," Beth hollered back.
They waited in silence for a minute until they heard a door slam. Beth
got up and walked to her door. She opened it and listened for a moment.
They heard a car start and drive off.
"Good," Beth went back to her desk and sat. "He only wants us to be
able to go out sometimes because he thinks he can get some kind of sex
from me if he can't get it from someone else."
"That would be pretty shitty," Cheryl told her. She kicked off her
shoes and lay down on her side on the bed.
"Yeah, well that's my fault," Beth groaned. "I guess I've been a little
too easy. Guys talk."
"I have to say, what I saw at the cabin made it pretty clear it wasn't
your first time doing some of those things. I thought we told each
other everything," Cheryl told her, her voice full of concern for her
friend.
"To be honest," Beth looked down at her hands in her laps, her fingers
twisting around each other, "I didn't want you to think less of me. Do
you really want to hear this?"
"Of course!" Cheryl answered. "I want you to feel like you can tell me
everything. I already have told you everything about me."
"Well, Cheryl, I gotta tell ya, you're pretty boring," Beth laughed
nervously. "But, if you want to hear it..."
Cheryl grabbed Beth's pillow and made herself comfortable. She thought
it could be a long story.
"OK, so you remember when I was dating Carl? He was seventeen, I was
fourteen. Everyone was saying he was too old for me but I wouldn't
listen, I was in high school now and even though I was a freshman I
felt like I should be treated like a grown-up and Carl did that. After
we were going out for a month he started driving us out to the lake. We
went from kissing to touching each other in just a couple weeks. Then
his parents went out one night and we stayed in. He took me to his
bedroom and we had sex, he was careful and pulled out before he came,
didn't need to get pregnant. I felt so good! So grown up.
"A week later we were back in his bedroom again, this time he wanted me
to go down on him. He showed me a porno of girls giving guys blow jobs
and said that was what he wanted. I didn't want to disappoint him so I
started sucking his dick. When I felt him getting close I stopped and
just started jerking him off. He told me that wasn't what he wanted but
I told him it was too gross. He twisted my arm behind my back and
forced it back into my mouth. I had no choice, he came in my mouth and
I swallowed it. It wasn't as bad as I thought so I didn't run away.
Instead, we went to the lake the next night and I did him in the car,"
she choked out a laugh.
"Of course that wasn't the end," she went on. "Next time we were in his
bedroom we wanted to fuck again, but this time he wanted to do me in
the ass. 'That way we don't have worry about you getting pregnant' was
he reason. It made sense, I wanted to please him, and it hurt some. No
matter what we did, it was actually what I did to make him feel better.
I never really got satisfied. Needless to say, as soon as I started to
ask about taking care of my needs he dumped me.
"Then you know the progression: Johnny, Steve, George, another Steve,
Alex and Jake. All takers, though I have found that I can get them to
take care of me knowing they will get theirs."
"Oh, Beth," Cheryl sat up on the bed. "I'm so sorry. I wish you had
told me about this back when you were seeing Carl. Come here."
Beth got up, wiped a tear from her eye, stumbled over to the bed and
sat beside Cheryl and leaned against her. Cheryl wrapped her arms
around Beth and hugged her tight.
"There's one more thing I ought to tell you," Beth sniffled.
"Anything," Cheryl continued holding her.
"I don't want things to change between us though, and I'm afraid they
might," Beth continued.
Cheryl was a little alarmed at this statement but refused to believe
there was anything Beth could tell her. "Look, I've seen all those guys
around school so I know you haven't killed them and hidden the bodies."
"No," Beth laughed again, "this is about up at the cabin."
Cheryl immediately thought of Don and wondered if she wasn't about to
tell her she wanted him. "Go on."
"Do you remember when the guys were, uh, servicing us and I grabbed
your arm?" Beth asked.
"Yeah, I jumped a bit. My eyes were closed and suddenly you grabbed my
arm. I didn't know what was happening."
"Well, I just suddenly felt the need to touch you," Beth confessed.
"You have always been there for me, never demanded anything from me. I
wanted to be with you. I almost reached for your boob instead, but at
the last second I grabbed your arm."
Cheryl was shocked but didn't move, didn't push her away. She knew Beth
was hurting and that was enough to stop her from trying to separate
herself from Beth. She felt Beth's hand starting to move to her breast,
"What are you doing?"
"I want to make you feel good," Beth answered squeezing Cheryl's
breast. "You don't have to do anything. I just want to be with someone
I know loves me."
Cheryl was unsure of how to proceed. She didn't answer but Beth's
fingers were still working her breast, had discovered her nipple and
she was getting turned on despite herself.
"I've read that a lot of girls experiment in college," Beth whispered.
"After Jake dumped me I started wondering if maybe I would be happier
with a girl, someone who knows what it is like to be a woman."
A vision of Don going down between her legs, his eyes all made up, his
lips coated with lipstick burst into her mind. Gradually Don's face
morphed into Beth's face. She shuddered.
She felt Beth's hand leave her breast but slipped up under her sweater.
It quickly moved to her breast again slipping along the smoothness of
her bra. She realized she was still holding Beth, still hadn't said
anything to stop her. Her sweater started rising up and Beth pulled
away. She raised her arms and let her sweater disappear. Her bra
quickly went to wherever her sweater went.
Beth bent and kissed her left breast and began kneading her right,
Cheryl still sat there but couldn't help but start caressing Beth's
back, gently stroking her fingers up and down her back. Beth moved to
kiss her right breast and felt Beth's hand slip between her legs. She
didn't press, just let it lie there.
Beth sat up, "Take your pants off, please." She pulled her nightshirt
off and pushed her panties to the floor.
Cheryl looked at her friend standing there naked in front of her. She
hesitated, then slipped off the bed and undid her pants. She pushed
them and her panties in one motion to the floor and stepped out of
them.
When she stood back up Beth was smiling. Beth stepped up and pressed
her body against her and held her. Cheryl wrapped her arms around Beth
and held her. She thought perhaps they were done, that Beth had reached
the end. Instead, Beth looked up and gently kissed Cheryl on the lips.
The kiss lingered, Cheryl returned it and it deepened for a moment and
ended. Beth stepped away and gently pushed Cheryl back toward the bed.
Cheryl licked her lips; she tasted only her own cherry chapstick. She
crawled back onto the bed and watched as Beth followed her coming up
between her legs. She felt so vulnerable with her legs spread wide, her
best friend poised above her pussy.
Beth watched Cheryl's face as she reached up and slid a finger along
the outside of Cheryl's lips, then press and touched her clit. Cheryl's
eyes rolled back and her lids dropped closed. Emboldened by the
response she continued. Beth stroked the clit, slipped her finger
inside her friend. Finally she leaned in and kissed her. She continued
to work with her mouth and fingers until she felt Cheryl shudder and
completely relax under her.
Cheryl's head was spinning. She could feel Beth moving on the bed. Beth
lay down on the bed beside Cheryl, laid an arm across her stomach and a
leg over Cheryl's. She rested her head on Cheryl's shoulder.
Cheryl wrapped her arm around Beth as she regained her senses. She also
became aware of Beth's breast lying heavily on her and could feel her
wet pussy against her leg. She was surprised she wasn't trying to crawl
away but instead just wanted to hold her friend who she knew was still
in pain.
"Thank you," Beth murmured into her shoulder.
"You did all the work," Cheryl reached up and stroked Beth's hair. "I
should be thanking you. By the way, thank you."
Beth giggled. "I wasn't sure what it would be like. I actually enjoyed
it. I guess if someone asks in college I can decide if I want to or not
based on who it is rather than just curiosity."
"Glad I could help you out with that," Cheryl squeezed her tighter.
"But, I think I probably ought to get dressed again. I'm afraid your
mom will come back."
"Probably a good idea," Beth started to roll away but Cheryl stopped
her.
"I love you," Cheryl told her and kissed her again.
The kiss lasted longer than their first kiss. Cheryl felt Beth's legs
tighten around her own bringing them closer again until Cheryl broke
off the kiss.
They picked up their panties and slipped them back on.
"Why don't you get dressed and let's go out to a movie or something?"
Cheryl asked as she pulled her pants on. "You don't need to keep moping
about here."
"Wait, you mean you still want to do something after we've had sex?"
Beth asked. "Usually I get left alone afterward. Either I go home or he
does."
Cheryl stared at her for a moment unsure of what to say.
"I'm just fucking with you," Beth cracked up. "Unfortunately, it is
more true than not, but yeah, let me go shower and we'll go out."
Cheryl found the rest of her clothes and put them back on. She watched
as Beth gathered some clothes to put on and left.
They were heading for the door when Beth's mom returned.
"Hey Mom," Beth called as they were getting in Cheryl's car. "We are
going out for a while."
"Good," she called back pulling a couple bags from the trunk of her
car. "You need to have a good time and forget about that boy."
"Oh, we've been having a good time," Beth called back. "See you later,
love you."
Cheryl got in and looked at Beth.
"Well, I was having a good time, I thought you did too," Beth smiled.
"Right," Cheryl laughed, started the car and started to drive off.
"By the way," Beth began, "did you and Don have any fall out after that
weekend?"
"We haven't had a lot of time together yet but so far everything is
ok," Cheryl answered.
"That's good," Beth leaned back in her seat, "hope it stays good."
Chapter 4: Don's Revelation
Cheryl sat in the passenger seat as Don piloted the car toward their
parking space out by the lake. It had been a while since they were last
able to come out here, and a bit of time had passed since the weekend
at the lake house. Cheryl was looking forward to this again but
couldn't shake the vision of Beth's face between her legs. She kept
debating in her head whether to tell Don about that afternoon. She
didn't really do anything, but she didn't stop anything either. Is it
cheating on your boyfriend if it wasn't another boy? She just wanted to
start kissing him and getting his cock in her hand and feel his fingers
in her pussy once again.
The car came to a stop and Don killed the engine. Tonight there was a
moon casting light on the water, it sparkled off the little waves
stirred up by the breeze. She undid her seatbelt and turned to get the
kissing started.
"Cheryl," Don pulled his seatbelt off and turned but did not lean in
for the kiss. "I want to talk to you about something. But first I need
to talk to you about you and Beth."
Cheryl felt her stomach drop and her mouth felt sour. How did he find
out? Did Beth tell him to try and get him to leave her? She wouldn't do
that, would she? "Um, what about?"
"Well, it was kinda disturbing when I found out you talked to Beth
about everything," he confessed. "I mean, I understand that you talk
about a lot, I even understand you would talk about some of the things
that might be considered private but I feel like you don't hold
anything back. I'm not sure I can be sure you would keep something
secret if I had something to share."
"Oh," Cheryl let her breath out, "is that what is bothering you?"
"Yeah, why?" he frowned a bit. "Is there something else I should be
worried about?"
"No," Cheryl tried to recover, "not at all. I was just wondering what
could possibly be more important than making out. I mean why come all
the way out here just to talk."
"I am looking forward to that," Don confessed, "but there was something
else I wanted to talk to you about first. I just need to be sure that
it is going to be just between us. I don't want you talking to Beth or
anyone else about it."
"Oh, ok, I can do that," Cheryl answered once again becoming concerned.
"You promise?"
"Yeah, absolutely," Cheryl leaned closer and grabbed Don's hands.
"Whatever you want to tell me, I'll keep to myself if that is what you
want."
"OK, good," Don looked out the windshield to watch the dancing light on
the water.
Cheryl waited patiently wondering what could be so bad. She wondered if
he had maybe strayed and was about to confess, or perhaps he was
thinking about their upcoming graduation and was thinking about
breaking up even before heading off to college. She was twisting
herself in knots making things up in her head wishing he would start
talking and dreading it at the same time.
"Um," Don finally broke the silence, "well, I, gee, this is tougher
than I thought."
"Maybe you just ought to say it because I'm going to throw up if you
don't tell me something soon because I am worrying myself sick."
"Oh, sorry, ok," Don resettled himself in the seat. "Well, remember the
weekend up at the cabin? Yeah, of course you do. It was amazing the
things we did in the bedroom and the shower, how could you not
remember..."
"Don!" Cheryl barked.
"Sorry, It's just that I am really nervous," Don winced. "OK, well I
haven't been able to get my mind off that weekend. Especially the first
part where I was dressed in your dance uniform." He hesitated watching
her face for some form of rejection. "Anyway, I've been wondering what
it would be like to wear a real dress."
"You want to wear one of my dresses?" Cheryl was relieved again and
confused at the same time. The dance uniform was supposed to be just a
joking around thing. A little test to prove the guys really would do
anything for them. She thought of Beth and Jake. A new thought occurred
to her. "Um, have you been thinking about Jake, too?"
"What?" Don's eyes went wide. "No! I just liked it walking around and
well I liked everything that happened after too. And I've been thinking
how short that skirt was and the satiny pants under it. I started
wondering what it would be like to wear a real dress, longer, y'know?"
"Um, I guess," Cheryl answered letting the thoughts and images play in
her head. "I mean I guess I don't really think about it because I've
worn dresses all my life. Sometime wearing them can be a real pain but
other times they make me feel real nice, or real naughty." She pulled
the hem of her skirt up. She saw it had the desired effect as Don
shifted in his seat and had to adjust himself. She lowered the hem just
a little. "Did you have a dress in mind?"
"I don't know," Don started fidgeting, "I suppose I would leave that up
to you since it's you stuff. That is if you are ok with trying this."
"Well, I sort of started this," Cheryl mused. "I guess I can find
something for you to try."
"Really?" Don asked. "You don't think I'm weird for wanting to do
this?"
"I guess I understand you being curious," Beth's face flashed again and
she shook it off. "After that, we'll see what happens."
Don leaned in and kissed her, she kissed him back. It didn't take long
before her panties were on the floor and his jeans were around his
knees.
Chapter 5: Don's First Dress.
Cheryl was carrying a larger purse tonight and Don seemed to be driving
a little faster to the lake. She had looked through her closet and
found a dress she thought would work. It was brown with a scoop neck
and little cap sleeves. There was a band just below her breast and then
the dress fell loose to a few inches above her knees.
Don pulled into the space and they got settled.
"Do you want to put it on right now?" Cheryl asked him. She saw the
answer in his eyes before he even opened his mouth.
"Yes, please," he answered, his eyes hungrily eying her purse.
She pulled the dress which she had carefully folded from the purse. "I
hope this is ok, I thought it might be interesting enough."
She handed it to him and he looked it over, "I always liked this one on
you."
"Well, now I guess we'll get to see it on you," she giggled.
"OK, I'm going to go to the bathroom to change," he told her.
"Really?" she glanced out the back window at the concrete structure.
"Seems awful dark."
"It'll be ok, and it will be easier than trying to change in the car,"
Don explained. "I've done that a few times and it isn't that easy. Oh,
did you bring panties too?"
"You want to wear my underwear, too?" Cheryl reacted.
"Oh, I just thought it made sense," Don looked away.
"Shit," Cheryl thought. She hadn't thought about that and now she made
him feel wrong. She thought for a moment. She had bought some new
panties just for tonight and had them on. They were white and very
sheer both front and back. She sighed, reached under her skirt and
pulled her panties off and handed them to Don. "You better not get
anything on them; I need to wear them again when we head home." She was
surprised to feel a tingle of excitement at the thought of Don wearing
her panties and then her wearing them again.
Don nodded and checked the mirror. Any other car headlights would have
easily been seen. He skittered from the car and across the road. Cheryl
sat there waiting.
Sitting alone in the car there in the dark started making her feel a
little creeped out. She was about to lock the door when she saw Don in
the mirror scampering back from the bathroom. She could see he had his
clothes rolled under one arm. He reached the car, pulled open the door,
tossed his clothes into the back seat, dropped down into the seat and
closed the door. His face practically glowed from the smile that
adorned it.
"Get out of the car," Cheryl sighed.
"Huh?" Don's smile instantly disappeared.
"If you are going to wear a dress you are at least going to do it
right," Cheryl snickered. "When you sat down the dress caught on the
back of the seat, it got held up and now can see my, I mean your,
panties. So, you need to get out and get in right. Hold your dress with
one hand to make sure it stays under you, put your butt in the seat
gently, don't drop in like a sack of potatoes, then swing your legs in,
knees together. Now, try it."
The smile can back to his face. He felt around his back first and
indeed discovered what she said was true. He opened the door, got out
and pulled his dress back down where it belonged. He followed her
directions and once again faced her awaiting her approval.
"That was very good," she affirmed. She leaned over and kissed him.
The kiss evolved and soon they were touching each other. She felt his
hand move to her breast, first over her sweater then under and inside
her bra. She tickled his nipple through the dress top.
The breathing was getting heavy when she pulled back.
"I have to see," she offered a wicked smile. Then she reached down and
pulled up his dress exposing his panties. She looked at his erect cock
easily visible through the sheer white and the dark pubic hair that
surrounded it. "I guess it was lucky I decided to wear these instead of
something tiny. You like how they feel?" she played her fingers over
the panty lightly stroking his cock and balls.
"Oh my God, yes," Don gasped. "I like them even better than the pants
from the uniform. Aren't you worried someone might look up your skirt
and see something when you wear these?"
"First, I bought them just for tonight for you, except I thought I
would still be wearing them," she continued looking at him in the
panties. "Second, nobody would be able to see much since I keep myself
shaved and that cotton panel hides the rest. I see everything looking
at you."
A sudden flash of blue and red on the inside of the car caused Cheryl
the screech. She looked out the back and saw a police car had pulled
behind them. She looked at Don who had a similar look of panic in his
eyes. She pulled his dress back down and tried to straighten herself
under her sweater before the cop could reach the side of the car.
"What are we going to do?" Don's voice had gone up three octaves.
"I don't know, we haven't done anything wrong," she tried to assure
him.
"I'm wearing your dress!" he hissed.
Before she could answer there was a tap on his window.
Don reached over and pressed the button that lowered the window.
"Good evening," the cop shined the flashlight into the car, first at
Cheryl's face, then Don's. "What the hell are you two up to? I think
maybe you both ought to step out of the car and around the back. Make
sure you have your ids with you. Do you have any weapons in the car?"
Don shook his head vigorously. "No, sir, nothing."
"Uh, huh, let's get a move on," he stepped away from the door and to
the back of the car.
Don reached into the back seat and grabbed his clothes. He pulled the
wallet from the pocket and it fell to the floor. "Damn, I can't reach
it."
Cheryl grabbed his arm. "Relax. Get out of the car, reach back in to
get your wallet. Remember to bend at the knees rather than leaning in
or you'll give that cop a show. Understand?" She finished pulling her
license from her wallet.
"Any time now," the cop called out.
Cheryl got out, checked to be sure her skirt was in place. The night
air reminded her that her panties were covering a different ass than
hers at the moment. She walked to the back of the car, handed her id to
the cop and stood there trying to look unworried. Indeed she had less
to be concerned about than Don.
A moment later Don arrived, head down, he handed over his id as well.
"Wait here," the cop instructed and went to get in his car.
"Don," Cheryl whispered. "Relax, I have an idea, no time to explain."
"OK," the cop came back and handed them both their ids again. "Now,
last week there were some kids out here tearing things up."
"It wasn't us," Don blurted out.
"I know that, but we've been coming out checking to see if we can catch
them at it again. How long have you been coming out here?"
"A couple years now, since summer before junior year," Don answered.
"You always wear a dress out here, Donald?" the cop asked.
"No," Cheryl responded. "This was the first time. There was a boy this
fall that wore a cheerleader uniform all day at school for his
girlfriend, long story. Anyway, Don and my best friend's boyfriend at
the time were going to tease him but we stopped them. Well, they broke
up and the boy was being given a hard time about it. I asked him if he
loved me enough that he would wear a dress for me, and that I loved him
enough that I would tell my friends to take a hike if they didn't like
it. Anyway, I wasn't going to make him do it at school but thought this
would be funny."
The cop stood there looking back and forth at the two of them for a
long moment. "Kids do some really crazy things. But, I wouldn't want to
be caught in a dress if those trouble makers come around again. I don't
think they would care how much you love each other. I think you ought
to consider getting back to town."
"Yes, sir," they both chimed. After a hesitation they went back to the
car and got in. Cheryl was relieved and had to giggle a bit as she
watched Don get into the car in a proper fashion.
"I can't drive back to where people are like this," Don exclaimed.
"I know, just wait a sec and see if the cop leaves," Cheryl answered.
After a few very long minutes the red and blue lights turned off and
the car pulled away.
"I think I'm going to change now," Don sighed.
"Probably a good idea," Cheryl agreed. "I don't know if I can get back
in the mood again for a while."
"I don't think I can go back to the bathroom to change, I'll probably
need your help."
"OK, how about first you give me back my panties," Cheryl suggested.
Don lifted his butt, reached under his dress and the white panties
appeared below the hem of the dress and slid down his legs. He handed
them back to Cheryl.
She pulled them on and pulled her dress back down. Her part done. She
watched as he finished getting his own underwear back on, then pulled
his pants up under the dress. He began trying to pull the dress off
over his head, Cheryl reached over and helped pull until it came free.
She carefully folded it back into her purse while Don got his shirt on.
Cheryl sat there quietly while Don backed out of the space and followed
the road away from the lake back towards civilization.
"So, I guess that wasn't as enjoyable as you expected," she started.
"It was great up until the cop showed up," Don answered. "I mean, I
really liked wearing the dress. It was exciting wondering when you were
going to put your hand up it and touch me. And those panties! Man, they
were great."
"Well, they are back where they belong," Cheryl pulled her dress up
displaying them.
Don reached over with one hand and rubbed the front of them. "You're
right, can't really see anything but it is still exciting. I'm getting
a boner again."
Cheryl laughed, pushed his hand away and pulled her skirt back down.
"You better pay attention to the road. I don't want to get into an
accident after all we've been through tonight. Are you saying you'd
want to wear a dress again?"
"I guess," Don answered weakly, "does that gross you out?"
Cheryl thought about it before answering. She thought about lifting his
dress and touching him. "No, I'm really surprised. I thought the thing
at the cabin would be funny, and then tonight you'd try it and that
would be it. But, it was kinda fun and sexy."
"Maybe we can try again one day," Don suggested.
Cheryl rode along thinking about that for a while. "What are you doing
tomorrow?"
"Working for a while, eleven til six, why?"
"How about shopping?" she suggested. "Men hate going shopping, I know,
but we know you can wear my clothes so we are going to buy you your own
dress and underwear. How's that?"
"What would I do with it?" Don stuttered. "I mean where would I hide
it?"
"I suppose wherever you feel you can," Cheryl answered. "Look, I didn't
mind lending you my dress tonight, but I think you should get your own
and I will get to see what you like. And you are definitely getting
your own underwear. You can even have a bra if you want. Totally up to
you. You'll pay for whatever you want, but I'll shop for it because I
know that could be tough for you. This will be interesting."
Chapter 6: The Shopping Trip
Cheryl walked into the mall holding Don's hand. They decided to just
walk around first window shopping. She watched Don eying the clothes in
the windows, and the girls walking around the mall. She didn't feel
jealous at all, she knew he was looking at the clothes, although the
way he looked at that girl might be more than that. She pulled his arm
when she felt he was staring a little too long.
After walking around for about an hour Cheryl decided it was time for
action.
"Have you decided what you want to look for?" Cheryl asked.
Don looked around to be sure nobody would be able to overhear him, "I'd
just like something simple, easy to put on, y'know."
"Well, that still leaves a lot of options," she continued. "Would you
like it to be long, below the knee, above the knee, really short? Have
you thought about maybe a skirt and blouse or are you set on a dress?"
"A dress, I think," he whispered. "Short, above the knee like the one
you let me wear, but not too short."
"OK, let's go in here and see if we can find something," Cheryl pulled
him into one of the women's clothing stores.
She led him to an area of the store that had dresses in her size. She
looked over each of the racks looking the dresses over. She pulled one
off the rack and held it against her. "What do you think of this one?"
Don looked it over. "That would look really nice on you," he spoke a
little too loudly.
"Relax," she instructed him. "Nobody is going to care unless you bring
attention to yourself trying not to bring attention to yourself. Now,
do you like it or not?"
"Yeah, I like it," Don nodded.
"OK, I'll try it on for you," she draped it over her arm and went on
looking.
She collected three dresses and went to the changing room. She tried
two on and came out to show Don, but told him the third didn't fit
quite right.
They left that store and went on to another. Cheryl was really enjoying
doing the modeling and trying to imagine Don in each of the dresses she
tried on.
After the fifth store she was starting to tire of changing over and
over. "Have you changed your mind?"
"No," Don answered. "Since this is going to be my only, ah, one, I just
want to be sure I have something I really like."
"I understand that," Cheryl nodded in sympathy, "you could buy two or
three."
"No, just one for now," Don objected. "I'm afraid if someone else finds
out, like my parents, then I'll have to get rid of it. So better it
just be one."
"OK, let's go."
Eventually he selected a yellow, short sleeved dress with a high
collar, it fit Cheryl tight to the waist then opened to a short full
skirt.
"OK, now you need something to wear under it," Cheryl led him into one
of the large stores. "I'd take you to a lingerie shop but the prices
there would scare you. We can find something nice here. Have you
decided on a bra or not."
"Oh, um, no, not today I don't think," he answered and followed her in
between the racks of bras and shapewear on the way to a couple tables
with panties spread around them.
Cheryl picked out a style she really likes, showed him some that he
couldn't wear, not enough material to keep him in. He picked from the 3
for $20 pile and found some that were what he considered sexy enough
with lace, sheer and satiny material to make him happy.
Cheryl stood at the register and paid for the panties.
"So, will I get to see you in your new outfit sometime?" she asked as
they walked through the mall back toward the car.
"Of course," Don answered, "I just don't know when. I'm scared to go
back out to the lake for now. And I don't know anywhere else that would
afford us the privacy we need."
"I'm sure we'll figure something out," Cheryl told him.
They got in the car and she leaned across the seat, kissed him and
slipped her had into his lap. "I would hate for one bad night to ruin
what we've been doing for the rest of our year."
"Me too!" Don mumbled against her lips.
Chapter 7: Opportunity Knocks
Cheryl waited anxiously for Don's arrival. Her parents had gotten
tickets to a concert and had wanted her to attend with them but she
begged off saying she had homework and wasn't that interested. Truth
was she was interested and would love to have gone along but there was
something else she wanted more.
The knock on the door she was waiting for came. She rushed to let Don
in; they would have several hours together in the house alone. She
chose to wear the same brown dress she had loaned Don that disastrous
time at the lake when the cop showed up. She hoped he'd be more turned
on knowing he'd worn the dress she had on than reminded about the cop.
And if it wasn't enough, the panties she's picked out would certainly
get his attention.
She briefly wondered how much planning she actually had to do where a
teenage boy was concerned but she enjoyed playing the vamp and hoping
it was her that got him going more than raging hormones.
She pulled open the door. Don wrapped his arms around her, the paper
bag he carried bumped her back.
"I'm so happy this worked out!" she exclaimed. "Get in here." She
yanked his arm and pushed the door closed. "We should have at least
until 11:00, maybe later, but that will be plenty enough time."
"You're sure they won't come home early," Don looked around. "I'd
really hate for them to come in and find me in my dress."
"Babe, finding you in a dress will be the least of our worries if we do
the things I hope we do," she gave him a sly look. "Now, if it will
make you feel better, I'll turn on the radio to that classic rock
station they listen to. If anything changes, they'll be announcing it,
and they may even say when the concert ends so we can start cleaning up
if it is earlier that we expect. OK?"
Don nodded, still nervously twisting the bag in his hands.
"OK, do you want to change in the bathroom?" she asked and felt a
tingle run through her body.
Again, just a nod in answer.
"OK, you know where it is," Cheryl waved her arm in the direction of
the bathroom. "Don, put your clothes in the bag so you can change fast
if something does happen, doesn't hurt to be prepared. And relax, we
are going to have a really good time."
"OK," he finally managed to speak again and disappeared from the room.
"Meet me in my room," she called to him and proceeded to her bedroom.
She went to her room a little disappointed. He didn't say anything
about the dress she wore, didn't give her the lusty kiss she had
wanted, didn't even seem notice that she was not wearing a bra either.
She began to worry his paranoia might ruin the evening. "Well, it's the
first time we've tried this. Maybe I should be a little more worried,
too."
She sat down in a chair in the corner of her room. She checked her
dress to make sure it was arranged just right. She wanted him to get a
good look at her legs, but not see too far, not yet.
A moment later Don came into the room. He placed the bag on the floor
by the door bending his knees to do it. Her first thought was how odd
he looked, a boy in a dress. Then she allowed her perception to shift,
to try and do away with those notions. He looked cute. The dress fit a
little different that it should due to the body type, but his legs
looked nice, better than some of the girls on the dance team really.
"So, is this the first time you've put on your dress or have you tried
it before?"
"Well," Don moved over to the bed and carefully sat on the edge. She
watched as he made sure to pull the skirt under him as he sat. He
crossed his legs at the ankles. "At first I hid this stuff in the trunk
of my car, but after a few days I worried that my dad would need to
borrow my car for something and get in the trunk and find them. I
thought I could just tell them they were yours but then I would have to
explain why I had a dress and underwear of yours in the car."
Cheryl listened to his story, he was going into so much detail but she
also saw that he was starting to relax. She had taken the chair so that
he would sit on the bed if he chose to sit. At least so far that had
worked out.
"So," Don continued, "I decided I could find a place in my closet in my
room. There's enough junk in there I don't think anyone would find
something unless they knew what they were looking for. Then, one night
I woke up, everyone else was asleep, and I decided to try everything
on. It was amazing, I was so excited. I couldn't wait to find a way for
us to share this. And now, here we are."
"Here we are," Cheryl grinned. "In my bedroom, alone in the house."
"You're wearing the dress I had on when the cop caught us," Don pointed
out.
"Yeah, I hope that isn't freaking you out. If is it I can change and
put on a different one," she offered. "I just thought maybe you might
like to see me in a dress you wore."
"Actually, you wore this one, too," he smiled for the first time. "When
you tried it on at the store for me."
"Oh, you are right," she got up from the chair and sauntered across the
room to the bed. She sat on it beside him.
She leaned over and kissed him. She was thrilled when she felt him
return the kiss without hesitation. She reached over and caressed his
chest seeking his nipple. She found the hard little nub in only a
second and he took a deep breath. She was happy to feel he also took
the hint and reached for her breast.
"Are you wearing a bra?" he gasped and started down at her breasts.
"You can feel I'm not, neither are you," she teased and leaned in to
kiss him again.
She was getting hotter by the moment. She wanted to lift his dress and
see which panties he wore, and what he looked like in them. She also
ached for him to get under her dress. She decided she couldn't wait any
longer.
"I want to show you something," she purred as she stood. She watched
his eyes as she slowly raised her dress until a small shiny patch of
black fabric appeared to him. Then she slowly turned around so he could
see her bare ass. "I haven't worn a thong before but I kinda like it.
What do you think?"
"Oh, wow," he said as he reached out and squeezed her ass. "I'd say I
like that a lot."
"Good, I hoped you would," she let her dress fall slowly back into
place. "Now, I really want to see yours." She reached for his dress and
began pushing it up his legs.
"Wait," Don placed a hand on his leg holding the dress from moving.
"Let me stand up and do it. Just like you did."
Cheryl grinned and turned and sat on the bed. He was really into it
now. And so was she, she was really aching to see under his dress.
Don stood and began to slowly raise his dress up. Cheryl's eyes were
riveted on the hem as it creeped up his thigh. She wanted to tell him
to hurry but knew he was doing the same to her that she had done to
him. Finally a bit of white appeared, then a little more, she could see
the bulge from his balls and his cock. A stitched flower pattern began
to appear and then the lace above it. And through the lace more of his
hard cock. Finally the top of the panty revealed that it was just big
enough to hold him in.
He slowly turned around, just as she had, and showed the backside. Like
the front there was a pattern and lace. The panties were cut high on
the leg so they had already started to imbed themselves in the crack of
his ass, half his cheek bare.
"My, my," Cheryl leaned forward and caressed his ass, then placed her
hands on his hips and turned him back around. She traced his cock
through the lace and the satiny flower pattern. "Are these your
favorite of the ones we got you?"
"Actually, I liked them all a lot. I thought you might like these the
first time."
"I do," she reached up and pulled them down. She grabbed it, slid
forward and immediately engulfed it with her mouth.
"Oh, God," Don groaned.
Cheryl licked and sucked and stroked. She had so desired this moment.
She felt Don starting to move in a rhythm, starting to fuck her mouth.
At first the thought excited her and she tried taking him deeper into
her mouth but then she remembered she didn't want it to end this fast.
She wondered briefly if she let him come in her mouth now, would he
recover faster wearing these panties and dress? It obviously excites
him, and me.
"Ok," she leaned away, "not yet. We have time." She pulled his panties
back up and gave his dick one more rub. "You aren't going to come in
your panties now are you?"
"Only if you keep touching me like that," Don panted.
She pulled his dress back down. "OK," she thrilled at the feeling of
control she had.
"May I?" Don came forward and gently pushed her back. He raised her
dress and rather than pull her panty down he moved the tiny scrap of
fabric to the side and began kissing her.
"Oh God," she did realize she had just used the exact same term as Don.
She was even more turned on feeling the thin band of the thong moving
against her ass as he moved it to get to her various parts. A few
moments later she couldn't resist humping against his face. She reached
out placing her hand on his head helping him go just where she needed
him.
"OK," he pulled away and slipped her underwear back in place. "Not
yet."
"Oh, that sucks," she cried out laughing at the same time. "Get up here
beside me."
She moved around on the bed to make room. Don move onto the bed beside
her and adjusted his dress as he got in position.
They kissed and Cheryl tasted herself on his lips. Again a mental image
of Beth down between her legs just as Don had been flowered in her
mind. She pushed it away and visualized Don's panties and the gift it
held for her.
They kissed and touched until Cheryl couldn't handle more. She sat up
and pulled her dress off. Next she leaned over directing a nipple
toward Don's mouth.
After a moment, "Do you want to take your dress off? You can leave it
on if you want but I want to get on you like at the cabin. I'm going to
pull your panties down and I'm not sure but you might get your dress
kinda messy."
Don stopped sucking on her tit, "I better take it off for now."
He sat up and Cheryl helped pull it off him. They tossed both dresses
off to the side. Don lay on his back; Cheryl moved to straddle his
legs. She pulled his panties down to where his balls still nestled in
them.
She moved higher and slid her panty along his shaft and shivered at the
feel of him. Don grabbed her breasts and began licking and sucking
them, switching back and forth, kneading and pinching the other while
she slid up and down his cock stimulating her clit. Then it happened,
the tiny little panty slipped away to the side and his cock slid
directly against her. She gasped and stopped her eyes wide.
"What's wrong?" Don gasped.
"I want to do it," Cheryl stated before she was even aware she was
going to speak the words out loud. "Wait here a second."
She swung her leg off Don and got off the bed. She went to her closet
and pulled an old towel from inside. "Did you bring a condom?" she
hoped.
"No, I didn't think we'd be going that far," Don sighed.
"Well, we don't have to if you don't want to," she stood holding the
towel at the edge of the bed. "But if you want to, you have to promise
me that you won't come inside me."
"OK, I promise," Don immediately answered. "What do you want me to do?"
"Get off the bed, you need to be on top," Cheryl answered and began
pulling back the bed clothes and placing the folded towel on the bed.
"Beth told me the first time can be messy, and painful, so please try
and be gentle, and if you think you are even close to coming you better
pull out."
"I'll try," Don answered, "to be gentle!" he quickly added when he saw
the look on Cheryl's face. "And I'll pull out at the first sign."
"OK," Cheryl answered. She pulled the little thong off and moved onto
the bed. She spread her legs wide.
"Do you mind if I leave my panties on like this?" Don asked.
"No, that's fine, now come here," she spread her arms.
She watched as Don carefully climbed onto the bed and up between her
legs. He moved forward and she felt his cock bump against her. It
wasn't quite in the right place. She reached down and guided it toward
her. He moved forward a bit at a time, she gasped as she felt him part
her lips and begin to slip inside. She raised her knees to try and
facilitate him. He withdrew a little and pushed again. Then she felt
pressure. She groaned a little and Don backed off.
"It's ok, keep going," she begged.
Again Don pressed. Cheryl wrapped her legs around him. "The second time
is a lot better," that is what Beth promised. She wanted Don so bad now
she wasn't going to stop. The pressure became pain and suddenly it
faded. Not completely away but less. She could feel Don moving freely
in her now. She could feel her breasts bouncing as he buried himself
over and over.
Suddenly he gasped and was gone. She felt his hard cock trapped between
their bodies and suddenly there was a liquid warmth coating their
stomachs.
"Wow," Don panted. "That was amazing."
"You were wonderful," Cheryl praised him, stroked his hair with one
hand, let her foot fall down between his legs. She felt the only item
of clothing either of them had on rub against her calf, the cool feel
of his panties. "We are going to have to do a little cleaning up here.
The towel is old and I'm going to throw it out so if we can use it,
let's. OK?"
"Yeah," Don nodded and slowly extricated himself.
They worked to get all cleaned up, Don helped her remake her bed.
"It's only a little after nine, we still have more than an hour before
the folks will get home. Are you going to put your dress back on?"
Cheryl asked as she pulled her panty back on.
"Yeah, if you don't mind," Don smiled as he picked up both dresses from
the floor. He had already pulled his panties up once they were clean.
He handed Cheryl her dress.
They walked back into the living room and turned on the television.
They snuggled up together on the couch. Cheryl idly played with Don's
bare leg while they watched.
Cheryl glanced at the clock and saw it was about 10:30. "Probably ought
to change clothes and head out. My parents will likely be home sometime
soon."
"Yeah, I guess," Don stood up and smoothed out his dress. "Be right
back."
Cheryl waited alone replaying the evening in her head: Don showing up,
Don in his dress, all the sex, finally sitting together. It flowed
through rapidly and Don soon appeared again.
"I had a great time tonight," Don told her once again toting his paper
bag.
"I bet you did!" Cheryl teased. Then she went to him and kissed him.
"You were wonderful. Thank you."
She walked Don to the door and watched him leave. Once gone she went
back to her room and slipped into a nightgown, double checked that
everything looked to be in order and then went back to the living room.
"No more virgin," she told the television. It didn't answer her but a
smile graced her face.
Chapter 8: Senior Prom Night
Cheryl waited in a floor length, light blue dress that sparkled all
across the large skirt. It was strapless and left her shoulders bare,
the bodice stiff that held her breasts. She wished she had bigger boobs
to look like she really filled out the dress but there were more
important things going on.
She had been sneaking around between hair appointments, and nails
appointments, which she went to with Beth, taking care of a special
surprise for Don.
At last the doorbell rang and Beth's father answered the door.
"Good evening, sir," Don stepped inside. "Is Cheryl ready?"
"Yes, she's been waiting for you," he went back to the living room to
join Cheryl's mother. "Cheryl! Don's here."
Cheryl had heard everything; she was just waiting to make her entrance.
She walked into the room and looked Don over. She tingled all over
seeing him in his tux. He looked so handsome. His hair had grown out
over the year so that it lay an inch or two down his shoulders. It
glistened a golden yellow against the deep black of the jacket.
"I still think there ought to be more to that dress," her father
stated.
"Behave," her mother slapped his arm. "She looks beautiful. And Don
looks very handsome. You will be the best looking couple at the prom."
"Hardly," Cheryl answered. "There are some really pretty girls at
school."
"Doesn't matter to me," Don answered. "You are the only one I care
about."
"Oh, that is so sweet!" he mother cooed. "Come on, over here, we need
pictures."
Cheryl smiled and posed until it seemed like it had gone on long
enough. "OK, we need to get going. The dance will be over before we get
there."
"OK, ok, get going. Have a good time, be careful," she waved.
"Not too good a time," her father added.
"We'll be fine," Cheryl huffed, "and remember we will probably be going
to other parties so I might not be home until the morning." She turned
and left before her father could make another comment.
Don opened the car door and she slid into the seat then pulled the rest
of the dress in around her. Lot of kids found ways to rent a limo or
borrowed their family's fancy car, but neither her family nor Don's had
anything that fancy nor the money to splurge on a limo. Besides, this
worked best for her plans.
They arrived at the prom, had another picture done and went and found
their table. Within a couple minutes Beth walked up in a gold dress.
Hers had spaghetti straps, the front draped low enough that half her
boobs were visible and bounced as she walked. The dress itself was a
tight-fitting column with a slit that ran up her right leg to mid-
thigh.
"I'm glad you decided to come tonight," Don told her.
"Wasn't too sure I wanted to be a loner but it is the last event except
graduation," Beth told him. "I'm sure I'll have a good enough time."
Dinner was served to everyone: salad, followed by a choice of chicken
or fish with fingerling potatoes and a combination of green beans and
shredded carrots, then dessert of chocolate cake or cheesecake.
They finished eating and the band started ramping up the music to get
the soon to be former students on their feet. Don and Cheryl danced
several numbers together, Beth sometimes joined them or sometimes found
someone else to dance with.
Cheryl was having a great time when the music slowed. She moved close
to Don and they swayed to the music.
"Having fun?" she asked.
"Yeah," he whispered back. "Long as we are here together I couldn't ask
for anything more."
"What would you think of leaving?" she asked. "Like in a few minutes."
"Why? Are you not enjoying it?" he stopped moving.
"No, I am," she gave him a little push to get him moving again. "But,
I've been working on a little surprise for you."
"Really?" his voice rose a bit. "What kind of surprise?"
"If I told you, it wouldn't be a surprise," she teased him pleased to
hear the excitement in his voice. "Two more songs and then we'll sneak
out."
"I hope they're short songs," Don told her.
They danced to the next two songs and went back to the table to take a
few sips of water.
"You heading out?" Beth called as she came off the dance floor.
"How'd you know?" Cheryl replied.
"You just have that look about you," Beth answered. "Maybe we can catch
up later. There are enough people here to keep me entertained for a
while. Still pretty early."
"OK, behave yourself," Cheryl laughed.
She took Don's hand and led him back to the car. "You drive, I'll tell
you where to go."
Don wove his way through the streets making turns as Cheryl directed
him and finally into the parking lot of a small motel.
"What's this?" he asked as he parked in a spot she pointed out.
"It's a Dairy Queen," she groaned. "What do you think it is? It's a
motel. I got us a room. It isn't upscale but it is clean and when I got
the key earlier I had to promise I wasn't bringing a bunch of kids back
for a loud party. But we get to have some time just to ourselves
tonight. No worrying about parents coming back."
"I wish I had known," Don answered. "I might have helped."
"If you had known, it wouldn't have been a surprise! How many times do
I need to keep telling you that?" she pulled a green plastic diamond
shape from her purse, a key dangled from one end. She handed it to Don.
They left the car and Cheryl patiently waited while Don attempted to
get the door open. His hands were shaking so badly he was having
trouble getting the key in the lock. At last it slid home and the door
swung open. He held it while she entered and he closed it behind them.
"This is nice," Don spoke as he took in the room.
A king size bed was against the far wall, lamps on little end tables
near the headboard, a picture of a cabin by a mountain stream above the
headboard. A dresser with a television and it appeared the bathroom was
around the corner of the opposite wall.
Cheryl stood waiting for Don to finish his assessment of their
accommodations for night. He turned back to her, took her in his arms
and kissed her. She let herself melt into his arms.
"What did you think about the dance tonight?" she asked as they
continued holding each other.
"It was ok," Don answered. "Food wasn't bad, music was pretty good.
There just aren't that many people around that I want to spend a lot of
time with."
Cheryl stepped back. "And what do you think of my dress?" She rotated
her hips making the skirt swish back and forth.
"I told you I thought you looked beautiful," Don answered.
"I heard you, and I'm thrilled you think so," she smiled again, "but I
want to know what you think of my dress."
"Oh!" Don blushed. "I think it is amazing. I, well, ok, I wish I could
have worn something like that rather than this tux. All the guys looked
the same almost. A little different here or there but essentially the
same."
"Were you looking at other girl's dresses?" Cheryl pushed.
"Yeah," Don dropped his head a little embarrassed.
"Don," Cheryl took his hand. "Why are you embarrassed to talk to me
about this? I put you in my dance uniform, helped you shop for two
dresses and panties. We've had some fun times playing dress-up when we
can get the house to ourselves. Do you not think that I looked at all
the dresses the other girls were wearing? I wonder about if I could
look as good in some of them, and know I would look better in some, and
have to admit that I wouldn't look as good in some too."
"No, I think you'd look incredible and in any of them," Don tried to
defend her.
"Really?" she pressed, "You think I would look as good in Beth's dress
as she does? I mean sometimes I am so jealous of her boobs. And don't
even try to pretend you didn't notice. Every guy in the room probably
noticed."
"OK," Don snickered. "Maybe the top would have been a little less
impressive, but you have great legs and ass to make up for it on the
bottom."
"Fine, nice save," Cheryl leaned in and kissed him again. "But I have
another question. Do you remember the dress I wore to the Junior Prom
last year?"
"Oh yeah," Don answered. "Dark blue, long skirt like what you are
wearing but it actually had something that went up to your neck. Your
shoulders were still bare, but you looked great in that as well."
Cheryl walked toward the bathroom. She reached into the closet and
pulled the Junior Prom dress from the closet. She stepped back around
the corner holding up. "Would you like to try this on? Or would you
rather just make out? And before you tell me what you think I want to
hear remember two things: One, I brought the dress with me, and Two, we
have all night."
She watched as Don's eyes travelled the length of the dress. She
reached over and fanned the skirt out to remind him it was as full a
skirt as the one she had on. There wasn't as much sparkle on this dress
but it had its embellishments at the waist and bodice.
"Yeah," Don's voice shook as he answered. "I'd like to try it."
Cheryl smiled hoping he would want to. Through their recent games she
had learned that he really enjoyed dressing up with her, and she with
him. She took to watching him closer when they were out and saw he
looked at women in dresses and skirt, or slacks if she were really
pretty, but ignored the guys entirely. She had no doubt he was into
her. This was just a lot of fun for both of them and she wondered how
far he would really like to take it. It was time to find out.
"Take off your clothes," she instructed. "I have more surprises."
Don immediately began stripping off his jacket, shoes, tie, and all.
One piece of clothes after another landed on one of the chairs in the
room. Cheryl walked over to straighten out the clothes so they wouldn't
be too wrinkled when the time came to put them back on.
"I'd say you are looking forward to this," Cheryl grinned eying his
erection standing proudly between them. "So, I brought more than the
dress, of course. Are you ready?"
Don nodded.
She turned and pulled open a drawer just enough to reach inside. She
didn't want him seeing anything until she was ready for him to see it.
She turned and held a black, lacy garter belt in her hands.
"I thought you might like to try some stockings," she went to him and
wrapped it around his waist. "You haven't worn any hose before, but I
think you'll like this. Sit on the edge of the bed."
Don moved to the bed, Cheryl went back to the dresser. She came back to
him with the stockings hanging from her hand. She separated one and
laid the extra on the bed. "Watch now." She found the top of the
stocking and began working it up onto her fingers until the toe was
touching her fingers. "Lift up your leg." She fit the stocking over his
toes and began working the stocking up his leg. When it was all the way
up she took the strap and showed him how to press the tab under the
edge of the stocking and hook the clasp over it locking the stocking in
place. She adjusted it and then did the back one for him. "Now, you
try." She handed him the other stocking and watched him get it on.
"I didn't get one with seams because keeping them straight can be a
challenge the first time. You're doing great. Stand up so we can make
sure they are adjusted correctly, I think I got this one close." She
fined tuned one side and Don worked on the other following her example.
"Now, your panty," she pulled the panty from the drawer and held it up.
A black lace triangle displayed to Don, he licked his lips. "Now you
put this on over the garter because if you need to go to the bathroom
you don't have to mess with them. Let's see how they fit." She handed
them to Don.
He looked to see which way they went on and stepped into them. He slid
them up along the stockings and then into place, the waist almost as
high as the garter belt. Cheryl was happy to see they fit tight, his
cock pressed flat but still hard, easily seen through the lace. She
stepped around to look at his ass, also partly covered in lace. She
tingled with excitement wanting to touch him but she had so much more
in mind.
She went back to the dresser and pulled out a bra. When she turned back
before saying anything she watched Don absorbed in running his hands
across his legs, butt, and dick. "Ready for the next thing?"
"A bra?" Don was surprised. "I thought the dress would be next, I've
never worn a bra before."
"I know," she moved forward, "but I thought you might want to try it
all tonight. If you don't want to then we can skip it."
Don hesitated, she waited a moment then turn as if to put the bra back
in the drawer. "Wait." He called.
Cheryl turned back. "I thought you might. We've done a lot but surely
you have to be curious about the rest. You have on stockings that
you've never worn before, you seem to like them. Imagine how beautiful
that dress is going to look on you when we finish getting you ready.
This bra has straps that cross in the back so that they won't slip down
since there are no shoulders in the dress."
She helped him get it on, it was black as well, the band was lacy but
the cups were solid.
"I even devised something for you," she pulled a couple lumps from the
dresser. "These are made up of rice, and tissue, and some tape. They'll
fill out the bra, and give a little weight so you will feel like you
have breasts. Sorry, they are small like mine."
"I think it's amazing," Don squeezed his new boobs. "I can't believe
you've done all this. Now the dress?"
"Well, remember up at the cabin?" she moved to another drawer. "We put
some eye makeup and lipstick on you and Jake? Well, if you don't mind,
I'd like to do a real make-up job on you. It will take some time and we
should do it before you put on the dress."
"Oh," Don moved a little, Cheryl could see he was looking at himself in
the mirror. "If you want, I think it would be ok."
She smiled because she knew he wanted it but was still too unsure about
admitting anything. "Come sit over here, I need the light."
She went to work on his face adding color to his cheekbones, coving
part of his eyebrows, she thickened his lashes, and finished off by
painting his lips. "Now, I don't want you to look yet, let me get the
dress."
She went back to the closet and retrieved the long dress. She unzipped
the back and removed it from the hanger. She held it while he carefully
stepped into the dress and she pulled it slowly up his body. It had to
be pulled a little to get past his hips, then he slipped his arms
through the large holes and she pulled it up to his throat. She
adjusted the bra straps a bit to be sure they would stay hidden and ran
the zipper up his back. The choker collar was a little tight but seemed
fine.
"What do you think?" Cheryl asked as she pulled the skirt a bit trying
to make it lay right.
"I feel amazing," Don ran his hands down the dress. "Can I look now?"
"Not quite yet," Cheryl moved to go back to the closet and emerged with
a pair of sandals with a three inch heel. "I think these will fit,
it'll lift the dress a bit so it doesn't drag the floor so much. Sit on
the bed and pull your dress up a bit."
Cheryl squatted down and fought her own gown out of the way. She
slipped the shoe onto his foot and was satisfied that it fit him. She
buckled the strap around his ankle. Then she did the other foot. She
couldn't resist stroking the silky calf that lay in front of her.
"OK," she pulled his dress back down as stood up. "Let's let you take a
look."
Don stood and tried to find his balance atop the slender heel.
"Take your time," she instructed. "I hope those shoes aren't too
treacherous for you but I thought they would look really great with
that dress. And you need some kind of heel due to the length."
"I'm ok," Don took a tentative step. "It'll just take me a minute."
True to his word, the second and third steps became increasingly more
confident. He held his dress so as not to trip and moved toward the
mirror.
Cheryl watched him get there and look, then she moved closer and
wrapped an arm around his waist. "What do you think?"
"I can't believe this is me?" Don turned and stuck his chest out a
little more looking at his profile. "I mean, am I fooling myself here
or if you saw my out somewhere would you think I was really a girl?"
"Magic of makeup," Cheryl hugged his waist. "A little coloring here and
there helps hide some things and accentuate the others. Someone looking
close would probably be able to tell. Now, we could maybe do a little
something with your hair."
Both jumped at the sound of a knock on the door.
"Who's that?" Don whispered in a panic.
"I have no idea," Cheryl whispered back. "Go into the bathroom, I'll
see who it is."
Don quickly fled into the bath, only the rustle of his dress and the
click of his heels once he hit the tiles could be heard. Cheryl waited
a moment then walked to the door. She turned the knob and pulled it
open before she realized she should have asked who it was first.
"Took you long enough," Beth marched into the room without hesitation.
Cheryl felt her heart starting to slow down as she realized who it was
but fear was replaced by confusion.
"What are you doing here?" she started. "And how did you know I was
here?"
"Well, I got bored with all those stiffs we've been going to school
with these many years. Too many boys trying to make time with me,
really regretting that reputation I've developed. College will be so
different. Not going to just jump into bed with every Tom, Hairy Dick,"
she laughed.
"OK, fine," Cheryl was getting annoyed now. "But how? I didn't tell you
where I was going."
"Oh, right, sorry," she sat in a chair that didn't have Don's clothes
in it. "When we were at the nail salon this afternoon you went to the
bathroom and left your purse behind. I wanted a mint and didn't have
any. I also found that green plastic diamond shape thing with the hotel
name and room number. I figured I'd give you guys a couple hours to get
your jollies and then come get you to go have some fun. I know a club
that we can get into. Don! Come on out, I've seen you naked, or at
least close to it. Come get dressed and let's go party some more."
"Beth," Cheryl started.
"Wait," Beth furrowed her brow trying to piece together the puzzle.
"Why are all his clothes out her and you are still totally dressed?"
"Well, I had some ideas about tonight," Cheryl started but hesitated
trying to find a way around telling her everything.
"Holy..." Cheryl saw Beth's eyes go wide.
She turned and saw Don had come back into the room.
"You really need to stop being so pushy," Don spoke quietly.
"This is amazing!" Beth leapt up and walked around Cheryl. "You look
incredible! This is so much better than the cabin. I thought a couple
hours was enough for you to get your bed thing on but I can see this
must have taken all that time. Is this your dress from last year?"
"Yes," Cheryl answered. "I thought he might like to try it."
"You look taller," Beth observed. "You wearing heels?"
Don raised his dress and stuck his leg out.
"Oh, and I bet those are stockings rather than pantyhose," Beth
giggled. "Show me."
"Beth," Cheryl stepped back in. "Don't tease him. This was my idea."
"Oh, I'm not teasing him," Beth walked a circle around Don. "I love it.
I bet you got him some really sexy panties too. I wish I could have
been in on it with you. So, this is great! You are both ready, let's go
to the club."
"What!" Don reacted.
"Beth, you can't be serious," Cheryl responded.
"Why not?" she grinned. "It's actually not too far from here, the club
is fairly dark inside, nobody would get a decent look at him, not
enough to tell anyway. We'll go, we'll dance, have a drink or two then
you two can come back here and finish whatever you had in mind."
"Beth, Don isn't going to want to go out to a club," Cheryl protested.
The image of him standing there in a dress with a cop interrogating
them came to mind. She decided she wasn't sharing that story. "Besides,
don't you think we are a bit overdressed for a place like you are
talking about?"
"That is exactly why nobody will notice Don is Don," Beth crowed. "If
they take any interest they will be so busy looking at the girls in the
long gowns that they won't take the time to notice one of them might
not be as feminine as they should be, no offense Cheryl."
"Bitch," Cheryl gave her a little shove.
"Do you really think we could do it?" Don asked.
Cheryl whipped around to look at him surprised. "Do you want to try?"
"I think I might," Don answered his voice cracking. "Look, how many
opportunities will I get like this. Beth, Cheryl and I have been
playing dress-up since the cabin. It's fun, I like it. Of course it
hasn't been anything like this but I feel amazing and if you both think
we can do it without getting into any trouble I'd like to do it. I'll
be scared as hell at first, I'm already shaking, but I think I can
settle down."
Cheryl was ready to go as well but still harbored a lot of concern.
"Are you sure? I don't want you to do something just because you think
I want it."
"No, I want to," Don answered standing a bit straighter on his heels.
"Did you notice that Zach wasn't at the prom? He missed out on so much
this half of the year because he wore a cheerleader skirt for a day
because his girlfriend turned into a wimpy bitch. You thought it would
be funny to put me in your dance uniform, helped me when I told you I
wanted to try more, and then did this for me tonight. If you want to
go, I'm willing to go to."
Cheryl felt a tear start to form in the happiness she felt. Because of
the trust he had in her? She wasn't sure. "So, what do we call him? We
could call him Dawn, you know, D-A-W-N."
"That's boring," Beth answered. "I think he should be Kimberly."
"Why Kimberly?" Don asked.
"Don't know, just the name that came to me," Beth grinned. "Ever gone
outside while you two were playing dress-up?"
"Uh, just once," Don answered. "Don't want to do that again."
"Well, I think before we go out we need to do something about his
hair," Beth opined.
"We were actually just talking about then when you knocked and scared
the bejezzus out of us," Cheryl laughed.
"Well then let's get to it," Beth turned and moved Don back toward the
mirror. "I think a brush and some hairspray ought to cover it, don't
you?"
Cheryl nodded and they went to work. It only took a couple minutes for
them to get it into an acceptable state.
"Too bad we couldn't cut it," Cheryl mused. "I think he'd really look
cute with bangs, he has the face for it."
"Well we can't do it so let's take what we've got and go," Beth started
for the door.
Beth drove because her dress was easier to get behind the wheel in. Don
got into the back seat and struggled a bit trying to get all his dress
in so the door didn't close on it.
Cheryl walked beside Don, no Kimberly she corrected herself, and tried
not to reach out and hold his hand. Not that it would be wrong, you see
girls all the time holding hands in places like this. She watched as
Beth approached the man at the door. A few moments later she signaled
them to follow her in.
They walked in; the club was indeed dark, spot lights flashed from the
ceiling across the dance floor. It was pretty crowded out there. Lots
of the tables were already occupied or had drinks sitting on them.
Cheryl felt Beth grab her hand and start pulling her off in one
direction, she quickly grabbed Kimberly's hand and they marched in a
chain around the club. Three quarters of the way around they found a
small table they could claim.
"What do you want to drink?" Beth hollered above the music.
"White Zin, both," Cheryl answered.
Beth nodded and disappeared.
"You ok?" Cheryl leaned to Kimberly.
"Fine, we got in and that had me terrified," he answered. "But oddly
enough, I think it is too crowded to be a problem."
Cheryl took in the room while waiting for Beth to return. There were a
lot of girls in miniskirt, blouses or t-shirts, a few in dresses. Only
a couple in jeans. All were in high heels and lots of makeup. The guys
were all in jeans or slacks, a few fashion tees or button down shirts.
She was surprised everyone was dressed fairly nice as casual as the
place seemed.
Beth set the glasses down. "Let's dance!"
"Come on," Cheryl waved at Kimberly to follow.
The three went to the edge of the dance floor where there was still a
little room and danced together. Occasionally a guy would try and dance
in with them, or a few guys, but the girls didn't pay them enough
attention, it was getting late and they would go trolling somewhere
else.
They went back to the table. Cheryl picked up a flyer describing drink
specials and began fanning her neck.
"I feel like I'm burning up under this dress," Kimberly called to her.
"I thought a dress would be cooler."
"Nope, heat gets trapped under there," she explained. "And sorry,
didn't realize we'd be this active. Those stockings aren't doing you
any favors in the coolness department."
At that moment the lights came up.
"Guess it is closing time," Beth pulled her cell phone from her purse
and checked the time. "Time to get you two back to what you had
planned."
They piled back into Beth's car and once the doors closed Kimberly
erupted in laughter.
"Oh, my, God! That was so much fun!" he howled. He piled his dress up
in his lap trying to cool off. "I can't believe we did it. And it was
actually a whole lot more fun than the prom."
"I'm glad you had such a good time," Beth answered as she drove back
toward the motel.
"And I'm glad you found my key and came by," Cheryl added. "You've
given us both a memory we'll never forget."
"It is a memory for me too," Beth answered as she made the final turn
into the parking lot. "You two have been so good to me, and for me,
even if you have been keeping secrets. But I understand. I'm going to
miss you both after graduation. My family is heading out on vacation
and then I'll be off to college. I hope we can stay in touch but I know
that doesn't always work out. I just want you to know how much I care
about you both. Cheryl, you've been my best friend since Junior High,
I'll miss you so much."
"OK," Cheryl sighed. "Turn off the car and come inside. I have a bottle
of wine stashed, let's have one more drink together."
"I don't want to intrude any more than I already have," Beth wiped at a
tear.
"While you may have shown up uninvited, you are definitely invited in
now," Cheryl spoke very sternly. "Kimberly, do you have any
objections?"
"No," he answered. "You've both made my night so special I'll do
whatever you like."
"Good," Cheryl answered. "Then you get us some ice. I'll bet the wine
has gotten a little warm. Let's go in."
Cheryl opened the door and watched as Kimberly grabbed the ice bucket
and headed out the door. She was a little amazed at how easily he
walked back out the door to find the ice machine at the end of the
building.
"Not quite the evening you expected," Cheryl asked Beth as she sat on
the bed.
"No, not at all," Beth answered. "It has actually been better. You kept
the secret of Don dressing up all to yourself all this time, does he
know about our little frolic that day?"
"No," Beth sighed. "I've been keeping a lot of secrets from the people
I care about."
"Do you think Don's gay? Just afraid to express that?" she asked.
"Oh, no, at least not now," she explained. "We did talk about it once.
He told me he likes pussy too much."
They both laughed and there was a knock on the door. Beth went and let
Don in.
Cheryl got up and pulled the bottle from its hiding place along with a
cork screw. Don handled the opening of the bottle and poured them each
some wine in the plastic cups over a couple cubes of ice. He sank the
bottle back into the ice bucket to try and chill the remainder of the
wine.
"So, what's up for you two," Beth inquired as she sat on the chair. Her
dress fell open exposing her legs, though not far enough to show
anything.
Cheryl swallowed, this was a question she didn't want to answer yet.
She knew what was coming next. She waited for Don to address it. After
a moment he did.
"Well, we have a couple months before we go off to our colleges," Don
wrapped one arm around Cheryl. "We haven't talked about what we'll do
after that. It doesn't seem like either of us will be home much." He
coughed a bit, pulled his arm back and got off the bed. He shook his
dress out as he walked over and got the wine bottle. He poured some
more in his glass, offered it to the girls, then dropped the empty
bottle in the trash can.
"Fortunately, there is another in that drawer," Cheryl answered. "My
original idea was to get you all dressed up, then we would get a little
drunk and enjoy as much sex as we could until we passed out."
Don nodded, opened the drawer and put the bottle in the ice bucket. He
went back to the bed and sat beside Cheryl.
"I don't want to break up," he looked at Cheryl, "but I don't see that
we'll be able to see each other much over the next four years at
least."
"I know," Cheryl nodded.
"Oh, shit," Beth moaned. "I am so sorry to bring this up. I just
figured you guys had it all figured out."
"That's the problem," Cheryl answered. "We both had it all figured out,
we just didn't want to talk about it yet and make it real. We both know
at the end of the summer we are going to have to break up so we can
live a good life at college."
Don nodded while staring down into his glass of wine.
"Well, hey," Beth tried to cheer them all up. "you still have months to
go and also hours to go tonight. I should get out of your hair and go."
She stood up. "Could I just ask one favor, and I understand if you say
no."
Cheryl braced herself for the request.
"Do you think we could get a picture of the three of us? I promise I
won't share it anywhere, I just want to remember this night, how we
looked."
"Of course," Don answered before Cheryl had a chance to say anything.
"OK, then, how do you want to do it?" Cheryl stood up.
"That mirror there," Beth pointed. "I say we fix our makeup then step
back so we can get a good full view of us."
Cheryl went to the mirror and did a little touch up and saw Beth doing
the same. She spotted Don, or Kimberly, she was having problems
deciding what to call him, standing there unsure of what to do. She
finished her work and went to inspect his face. She touched up a few
places where a tear might have leaked out then stood beside him. Beth
came back and joined them. They looked in the mirror, adjusted their
position, and Beth snapped the shot holding the camera out to the side.
They looked over the picture together.
"I want a copy," Cheryl immediately said.
"So do I," Don added.
"You guys are the best," Beth hugged them both.
"What are you going to do now?" Cheryl asked.
"I don't know," she answered. "Maybe I can find one of the parties with
someone who isn't too obnoxious. Or maybe I'll just head home. It's
already after 3."
"Stay here," Cheryl offered.
"What?" Beth looked.
"What?" Don looked.
"Don," Cheryl turned to him and took both his hands. "I have to tell
you something." She proceeded to tell him of the afternoon that Beth
was so down, needed someone, and she was that someone. "We've always
been there for each other. I'd like her to stay."
"Wait," Beth jumped in. "Are we talking about just drinking up the rest
of your wine, or were you planning on having sex still?"
"I think that depends on Don," Cheryl answered.
"You are letting a teenage boy decide if he wants to have sex with two
girls," Beth snickered. "Duh!"
"Don," Cheryl was still holding his hands. "Actually, I think you might
be someone who thinks beyond just the sex. You might say no to the sex
thinking that's what I want, but I truly want you to know that I am
truly open to whatever you," she looked at Beth, "and you, are
comfortable with. This just came to me this minute and I am going to be
happy with whatever both of you decide. I just want us to stay together
tonight."
Cheryl watched Don stand there for a moment looking back and forth
between her and Beth. She could tell he was struggling with it.
"OK," Don answered at last. "First, how could I turn you down for
wanting to spend this night with your best friend after all you've done
for me. And Beth, you getting us out for an amazing night that I could
never have imagined. Of course, with two amazing women like this how
could I turn down an opportunity like this, but I will go along with
whatever Beth wants to do."
"That was diplomatic," Beth answered. "So, what is this really? Let's
just see how much of a slut Beth really is?"
Cheryl was shocked, it wasn't what she meant at all, "No, not..."
Beth interrupted. "Stop." She reached under her left arm and pulled the
zipper down, she shrugged her shoulders and her dress slithered down
her body and pooled at her feet. She stood there naked except the shoes
on her feet. "I'm trying to change, but there is still enough slut left
in me to want to do this."
Before Cheryl could recover from the abrupt change she found Beth's
tongue had invaded her mouth. Then it was gone and Beth was kissing
Don.
She wasn't really sure how things were going to go if they decided on
sex but apparently Beth had no problems just going for it. She let go
of Don's hands, watched Beth as she kissed Don and pawed at the front
of his dress. She decided it was time to shed her own dress and pulled
down the side zipper. She picked up Beth's dress and hung them in the
closet.
She returned still wearing a strapless bra and g-string. "I think it's
time to get him out of that dress."
Beth stepped back, Cheryl went and ran the zipper down the back.
"Oh, nice," Beth commented. "I think he should leave everything else
on, except the shoes. I'm taking mine off too."
"Sounds good to me," Cheryl answered.
They all began pulling off their heels and tossed them in a pile near
the wall.
"Now," Beth went on, "you get out of that bra and panty. I want you
naked."
Cheryl grinned and tingled as she stripped naked. "One more thing I
think." She walked over to Don and began kissing him, while she did
that she reached down and pulled his panty to the side exposing his
dick and balls. "Yes, I think this will work quite well, what do you
think, Beth?"
"I think that will do just fine," she walked over and joined Cheryl in
touching him. "But, I think I'd like to see things start with what I
wanted at the cabin, sort of. Do you mind if Don starts out by going
down on me?"
Cheryl remembered Beth telling her about when Jake and Don were down on
them and what she wanted. "Let's get to the bed."
Beth laid back on the bed, her legs hanging over the edge. Cheryl
crawled up beside her, on impulse she reached over and slid a finger up
Beth's slit. "You don't mind, do you Don?"
Rather than answer he dropped to his knees and buried his face in
Beth's muff.
Beth gasped. Cheryl leaned in and kissed her. She felt Beth trying to
gently direct her toward what she wanted done and allowed her to be
directed. Soon Beth's lips were kissing Cheryl's nipples and fingers
were sliding in and out of Cheryl's pussy. A moment later, she was
moaning and Cheryl knew she was coming. Don had gotten very good at
that.
Don crawled up the bed between them.
Cheryl turned and moved down. She began stroking his cock and then
started sucking on it. She looked up as she did and saw Beth had stuck
her breast in his mouth. Then she moved to join Cheryl.
"Want to share?" Beth asked.
Cheryl took Don's cock from her mouth and pointed it at Beth who
immediately engulfed it. When she let go Cheryl began sucking again.
"This isn't working for me," Beth sat up.
Cheryl looked at her, the head of Don's dick still in her mouth.
"He needs to move, get in the middle of the bed so we aren't falling
off the edge."
"Oh," Cheryl answered. She rolled over to one side, watched Don slip to
the middle and Beth climb back on.
"Much better," Beth smiled. "I kept rubbing my tits against his leg,
the stockings feel great, but I kept slipping off." She grabbed Don and
started sucking again.
Cheryl laughed. Turned so she could duplicate what Beth described and
was immediately thrilled with the new sensation. They worked over his
cock and balls and when they knew it was close both moved to the head.
Cheryl got the first load and moved aside, Beth quickly took over and
received the second. Together they licked off what dribbled out. Don
lay there panting and groaning.
"Well, two down," Beth grinned. "Get your ass up the bed."
Cheryl crawled up the bed and lay beside Don. She leaned over and
kissed him, he pinched her nipple. Beth crawled over Don's legs and
then straddled both Don's and Cheryl's leg. She proceeded to go down on
Cheryl.
Cheryl was drowning in sensory overload. The face she was kissing
looked so feminine, the face in her crotch was also her best
girlfriend. But there, lying atop black lace panties was a limp cock, a
black bra with breasts the size of hers, fake but the illusion was
there. What was she doing? The intensity built, she was about to
orgasm. She was living! She moaned loudly when the orgasm struck.
Gasped to catch her breath.
Beth moved slowly up to lay beside Don. "That was great."
"Uh huh," was all Cheryl could muster.
They lay there for a moment recovering then started again. For the next
several hours they found ways to pleasure each other. The curtains were
glowing from the risen sun by the time they lay there together
exhausted.
"Well," Cheryl sighed tiredly, "I'm afraid I need a shower before I can
go home. I'm pretty sticky. Can I trust you two alone for a while?"
"Sure," Beth laughed. "We won't do anything we haven't already."
Don groaned. "I'm not even sure I could walk right now."
Cheryl laughed, climbed off the bed and went into the bathroom. She
left the door open when she turned on the shower. She could hear them
talking but couldn't make out what they were saying. She climbed into
the spray. The warm water felt so good, her body was so sore. She
reflected on the evening, she had no idea it would go the way it did,
no idea what she expected when she invited Beth to stay, and she felt
so incredibly good about the whole thing.
She climbed out of tub and toweled off. She considered wrapping the
towel around her before going to dress again and laughed at the idea of
modesty. Both of them had seen every part of her pretty intimately.
When she entered the room she was surprised by what she saw, but not
shocked. Don was standing there in Beth's gold dress.
"Hey," Beth called. "We were talking and he said both his dresses had
full skirts like the dress you gave him to wear tonight. I thought he
ought to try a tight dress. I think he still looks pretty good."
"I hope you don't mind," Don answered, "I needed to borrow your
strapless bra, the straps just didn't look good. I mean, you can still
see the bra here, but the breasts fit it pretty good too and doesn't
look too bad."
"I told him some girls wear a bra in a dress like that but get
something special to show," Beth went on.
"Turn around," Cheryl instructed.
Don took a couple steps in a small circle. She noticed he had put his
heels on again. His leg flashed through the slit when he moved, she
caught a glimpse of the top of the stocking and knew if he could sit
down the garter strap itself would be visible.
She looked his butt over and could see the faint outline of the lace
panty he wore. She looked and saw the g-string still lying on the
floor. She went to it, picked it up and put it on. "You'd need
something like this if you want to wear a dress that tight, panty lines
just ruin the look of a dress."
"True," Beth answered, "but he has a great ass for that dress."
"You going to take a shower, Beth?" Cheryl asked. "I need to start
cleaning off Don's makeup."
"Yeah, good idea," she crawled off the bed. "Do me just one more favor.
Go sit down where Cheryl's going to clean you up."
Don looked at her a bit puzzled but Cheryl knew she had the same
thought.
Don walked over, Cheryl eyed his ass in the dress as it wiggled. He
turned, sat and crossed his legs. The slit was so high the dress fell
open exposing his legs, the tops of the stocking and an inch of the
garter.
"That's hot," Beth grinned.
Cheryl felt Beth come up beside her. Her arm wrapped around and
caressed her butt cheek. "Ever think you'd find it hot looking at a guy
dressed up as a girl?"
"Nope," Beth answered. "But tonight gave me a lot of things that I
never thought before. I'm heading for the shower. Thanks Don!" she
slapped Cheryl's butt as she turned away.
"Ow!" Cheryl jumped.
"You want me to change so you can get dressed before we start?" Don
asked.
"Only if you are tired of looking at me," Cheryl answered, a little
doubt crept in that he would say yes."
"Not at all," Don leaned back. "You are going to be able to get all
this off, right? I can't imagine trying to explain lipstick, or
mascara, or any of this to my folks when I get home."
"Don't worry," Cheryl pulled out some cloths and began scrubbing at
Don's face. "Sorry, this is going to be a little rough."
"I don't mind," Don grinned. "I like watching your tits wiggle while
you do it."
"You can't still be horny after all that?" she continued working on his
face.
"Well, it will probably be a few hours before I could muster a decent
hard-on again, but I'm still certainly hyped," Don explained. "I hoped
we would find a way to have some private time tonight. You provide a
hotel room, then give me that great dress to wear, we actually go out
clubbing! Then we come back and we end up in a threesome and Beth has
me put on her dress. I can't imagine anything better and well I'm horny
in spirit if not in body." He reached up and slipped a finger inside
her g-string.
"Stop that," Cheryl moved away. "I'm clean and you are just going to
make me want to sit on your face again."
Don laughed. "Beth might be disappointed. I couldn't give her a place
to sit while she makes out with you."
"Oh, you wouldn't have to be hard for me to rub on you, or I could just
sit on Cheryl's face again," Beth called from the bathroom. "Did I just
shower for nothing? Are we going to take another round?"
"Good grief!" Cheryl cried. "You two are insatiable. There, you're
done."
Don stood up, pulled his dress back into place, kissed Cheryl and moved
back into the room to undress.
"This will be fun," Beth stood naked beside Cheryl who was still only
wearing a g-string.
They both watched Don unzip the dress and slither out of it. He pulled
off the strapless bra, then slipped the panties down his legs. He
unclipped the stockings from the garter belt and removed the belt. At
last he sat down and pushed the stockings of his legs.
Both girls applauded.
"Will you look at that! There's a man in the room," Cheryl teased.
"That's quite a transition," Beth answered.
"Thank you both," Don walked across the room. He handed Beth her dress
and Cheryl her bra. "I'll be out in a minute."
Cheryl strapped the bra around her and settled her boobs in it. She
watched as Beth slipped the dress over her head and let it settle on
her body. She also adjusted herself as she zippered herself in.
"Thank you," Cheryl told her and kissed her. "Thank you for coming by,
for staying, for your friendship, for everything."
"Girl, you are my one and only true friend," Beth answered. "I hope
after all the craziness that college has to offer we can reconnect
again."
"I'm certain we will, even if we live on opposite sides of the world,"
Cheryl hugged her.
"Look, would you get some clothes on before I drag you back to bed,"
Beth sniffed back a tear.
Cheryl laughed and went to the closet. She pulled her dress out and
slipped it on. She just got it zipped up when Don emerged from the
bathroom again.
"I'm going to fix my makeup while you get dressed and then I guess we
can call it a night," Beth sighed.
Ten minutes later they were squinting in the bright sunlight heading to
the cars. They said their farewells and drove off.
Chapter 9: Final Summer
Cheryl sighed content. She opened her eyes to the familiar lights
dancing atop the waves of the lake. She was holding Don's dress while
he reached for the tissues to clean up.
"At least there aren't any cops this time," Don answered.
"Don't say that," Cheryl warned. "You haven't changed yet, and this
time it might be harder to explain you wearing a bra and stockings.
Especially in the summer, nobody wears stockings in the summer."
"I like them," Don defended his choice, "and so do you. Have you heard
from Beth at all?"
"What? You wishing she were here?" Cheryl asked pretending she was
hurt.
"No, not at all," Don answered. "Oh, funny."
"No, I haven't heard from her since she left," Cheryl sighed, finished
cleaning up and pulled her clothes back together. "I really wanted to
get us a room for tonight since it was going to be our last night. I
just couldn't swing it. What are you going to do with all your Kimberly
clothes? I mean, isn't that dress new?"
"Yeah, I thought it would be nice to wear something special for you
this last night," Don answered and started gathering his clothes from
the back seat. "Do you ever wish I was a normal guy? I mean, you know,
no Kimberly."
"Actually, no," Cheryl finished smoothing out her dress. "These last
many months have been fun. Much more fun than before. Oh, the sex we
could do was great then, but Kimberly added an edge to things.
Everything just kinda rolled along."
"OK, good," Don answered. "It was your doing that got Kimberly going in
the first place. Now, I'll have to go off to college and figure out
what to do about her, and I'll be living in a dorm, so in answer to
your first question, I suppose I'll find somewhere to hide Kimberly's
things until I can get a place to myself. I wish we were going to be at
the same school, or even close enough to visit."
"I know, me too," Cheryl was saddened by the idea, but had also
resigned herself to the way the future was going to be. She was leaving
tomorrow and she didn't want to try to maintain a long distance
relationship. She wanted to tackle college life without worrying about
how Don would react if he found out about one thing or another. It may
turn out to be nothing, she may be too busy to date, or go to a party,
or whatever, but she didn't want to hold him back either. "One more
coffee at the Denny's?"
"I think I ought to change clothes first," Don smiled and proceeded to
get out to go to the bathroom across the road.
Cheryl giggled and watched him in the mirror as he walked away. "I'll
miss him a lot," she thought, "and I'll certainly miss Kimberly as
well. And Beth."
Don came back, slipped Kimberly's clothes into the trunk and then got
in. He turned the key as started the car. "Time for that coffee."
He backed out onto the road and started back toward Denny's. Cheryl
reached over and laid her hand on top of Don's resting on the gear
shift.
"You know I really care about you," she told Don.
"I know," he answered. "And I know you are right about ending our
relationship. I just hope that if things work out later that we can see
each other that the least we can be is friends."
"Of course," Cheryl gripped his hand tighter. "If we both end up here
and you have a new girlfriend, or I have a new boyfriend, then we are
still best of friends. I'll just make sure my guy knows you need to be
my friend."
"OK, I'll do the same with my girl," Don answered.
Cheryl pulled the seatbelt around a little so she could lean over and
hug Don's arm. She rode that way for a mile or two then sat back up.
Saying goodbye at the end of the night would be hard, but she knew she
needed to set her sight on the future, there was a new world to
explore.