High School Sweetheart
Chapter 1
It was 1971 and Halloween had come around once again and I was dreading
it. It fell on a Sunday this year so I knew some time during the day my
mom was going to tell me I would need to escort my brothers and sisters
on their rounds tonight since my dad was working. I was in my freshman
year of high school and felt that I had become too old to dress up and
beg candy. I sort of regretted the candy part but I would probably extort
some candy from my sibling's bags as an escort fee or something.
"Tony!" my mom called out.
"Here it comes," I thought to myself. "Yeah. I'm in my room."
She appeared at the door. "Good, I need you to take the kids trick or
treating tonight."
"Really? What a surprise!" Sarcasm is big with me.
"Funny," she answered. Then she stood for a moment looking at me.
"What?" I asked.
"I think you ought to dress up tonight while you take them," she
observed.
"Don't you think it is a little late to be trying to figure out a
costume? It's 2:00 now, we'll be going out about 6:30. I don't think
there is enough time. Besides, I don't need a costume to babysit them
while they go knocking on doors."
"Actually, I already have an idea. I'll be back in a couple minutes."
I sat there staring at the empty doorway for a minute wondering what she
was up to. I didn't like this at all.
About 15 minutes later she was back at my door with an armload of
clothes. She laid them on the bed and then tossed me a small bundle.
"Put these on and then we'll work through the pile. This should only take
a few minutes to decide. Come see me when you are ready with the first
one." She pulled the door closed as she left.
I looked down at what she had tossed me and it was a pair of white
panties and nude pantyhose. My blood ran cold and I felt my stomach turn
over. I went to the bed and sorted through the clothes. Dresses of
varying lengths and one hot pants set. I recognized them easily enough
because I had been trying them on occasionally when I was alone in the
house. Was this her way of saying she knew and was calling me out?
I leaned out the door and hollered, "Are you serious?"
"Just get started. We have time but not all day."
I closed the door and looked again. The terror was passing and I was
feeling excited and anxious at the same time, it reminded me of the first
time I got to ride the big roller coaster. I dropped what I had in my
hands on the bed and stripped off the clothes I was wearing. I put on the
panties and pantyhose; I loved the feel of them. I felt I was lucky in
that I hadn't gotten a lot of body hair yet. Some of the other boys in my
gym class already had large amounts of thick, dark hair which I thought
was totally grotesque. I prayed often to be spared of that.
I picked through the dresses and found a maxi peach halter dress. It was
one of my favorites because the material felt so good against my skin. I
put it on and checked myself. That started me reacting in ways I was
accustomed to when dressing alone but a few adjustments and I felt I hid
the excitement I was feeling fairly well. It turned out it wasn't really
necessary as it quickly disappeared when I reached for the doorknob to go
see my mother.
I checked the hall, nobody was in sight. "Where are you?"
"In the kitchen, don't worry, everyone else is outside playing."
I went to the kitchen and found her sitting at the table brushing out a
blond wig.
"Come over here," she beckoned with the brush.
I went to her and she put the wig on my head, the hair coming down well
over my shoulders. She brushed and adjusted for a few moments.
"OK, step back and let's have a good look."
I stood in the kitchen wondering what she was seeing. I had a rough I
idea of how I looked having looked at myself in the mirror on those other
occasions. I was still young enough that I thought I would be fairly
passable but I wasn't sure. Even without breasts I knew this dress looked
good on me. I wondered how much the wig helped.
"Why did you pick that dress to try first?" she asked.
"Uh," I hesitated. I couldn't tell my mother the real reason. "I just
thought it would work best." I spread the skirt out a bit. "Being long it
would cover me up more."
"Hmm, yes," she mused. "Hold on a second." She left me standing there. I
started looking around for a shiny surface to see what I looked like in
the wig. Before I could find something suitable she returned.
"The color actually looks good on you but I don't think it will work
tonight though; you don't have any chest. There is another long dress, go
try that one. Oh, and put this on, too."
I caught a bra that she tossed me.
"For now, just wad up some socks or underwear to fill the cups. I need to
see the dresses on you with a chest. Go on, next"
I turned and went back again, hiking the skirt so I wouldn't trip. My
knees were a bit wobbly.
I took off the dress and put on the bra. I spent a few minutes trying to
stuff it with various things until I found a way to ball up a couple t-
shirts that seemed to fit the bill. I grabbed the other long dress, it
had a black sleeveless top, high collar that appeared to be as choker
with a triangular cut below it that didn't go far enough to expose the
cleavage I didn't have. The skirt was an Indian print and a wide black
belt wrapped around my waist.
"Well, that took you a while, but it looks like you did a good job." This
time she walked around me, then squeezed each of my breasts trying to
even them out a little more. "Do you like this one?"
"Yes," I blurted before I thought to stop myself from appearing too
eager. I found I was really starting to get into it now. "I mean, I think
it fits pretty well and it has me pretty covered up."
"Yes, it does, but the length might actually be a problem now that I
think about it. You'll be trying to keep up with the kids and needing to
climb stairs. I don't want you to trip and ruin the dress. Next."
So the long dresses were out. That was too bad really because I had found
I liked wearing long dresses more than shorter ones. I looked through the
shorter dresses and picked up a red dress next. It buttoned down the
front to the waist where it flared out in a full skirt that would reach
around my knees. A wide belt hung in a couple string loops. I put it on
and plodded back to the kitchen.
"This dress makes me think of Donna Reed," I announced as I came back in
the kitchen.
"Well it is actually shorter than the dresses she would wear," mom
informed me. She tugged and smoothed it while I stood waiting. "It fits
pretty well. Do you like it?"
"Yes, it's comfortable," I answered.
"OK, go try another," she waved me away.
I nodded and went off to my room. Two more outfits remained: the hot
pants, and a little black dress. The LBD was short, about mid-thigh, and
very fitted. I decided to try it next because I hadn't tried wearing it
before afraid I might stretch it out but since she wanted me to I didn't
have that worry this time. Once I squeezed into it I went back to the
kitchen.
"Wow, that is a little tight. Sorry, but it is too tight where you don't
want it to be. If you really like that one you'll have to try and make
some adjustments"
I tried looking down the dress but my breasts blocked my view. I had to
mash my breasts down to see what she was talking about. I had a definite
bulge where one didn't belong. Now that I was aware of it I could feel
that it was about to become even more prominent. I quickly turned my back
toward my mother pretending to try and examine the back of the dress.
"Yeah, well I am sure you could find a way. With that dress I think I
would put you in black hose as well. It's your choice."
"What if I decide I don't want to do this?" I asked.
"Oh, well tonight I am not going to include that as a choice. I think you
need to do this. I can tell you've been going through my clothes and I
understand you are probably curious. Tonight, you get to experience it
and it is the perfect time for you to do it. Halloween is a dress-up kind
of night. Not like you getting caught in a dress in July for instance."
The bulge in the dress was totally gone now. Hell, I wasn't even sure I
had a penis any more. I felt the color had drained from my face.
"Don't worry about it. I'm not mad. I just think it might be time you
stop sneaking around, at least from me. I think if you relax and let
yourself enjoy this as a Halloween dress-up you might actually have a
really good time. And maybe even satisfy that curiosity. Or maybe you
will have more questions. This is life and sometimes it takes longer to
figure things out. Now, last outfit, go!"
I returned to my room and sat down on the bed for a few minutes. I ran my
hands down across my knees, down my calves to my ankles and back up
again. I repeated the motion over and over as I thought about what my mom
had just told me. I thought I had been so careful when I borrowed her
clothes trying to put everything back exactly as I had found it but she
knew. I wonder how long she has known.
"Are you coming back?" she called from the kitchen.
"Yes," I shouted through the closed door. "Be there in just a couple
minutes."
I peeled the little black dress off and carefully laid it on the bed. I
picked up the hot pants outfit. It was hot pink with white pattern
lightly tracing all over it. I pulled on the shorts which felt smooth and
sleek. They easily slid up the nylons on my legs and instantly got me
turned on again. They were, of course, very short barely covering my butt
cheeks. The top was the same material actually looking like a mini-dress.
Once on, the skirt was just long enough to cover the shorts by less than
an inch. The front of the skirt had clear crystal button of which the
bottom couple were undone revealing the shorts whenever I took a step.
"Oh, my! Your legs look so long!" my mom exclaimed when she saw me. "Hold
on a second," she left the kitchen.
When she returned she had a pair of white boots in her hands. "Here, put
these on."
I sat and squeezed my foot into the first one. It was tight but the hose
allowed me to slide in. I zipped the side up and looked at it. It had
about a 3 inch heal and the top was about an inch below my knee. I put
the other on and stood up. I wobbled a bit at first but the heels weren't
that narrow and after taking a few steps around the kitchen I was walking
fairly well.
"Well, first of all you look great. Secondly, if you were my daughter
there is no way I would let you out of the house looking like that," she
stated. "Third, you are my son so there really is no way I am going to
let you go out like that."
"Hey, these are your clothes and you wanted me to try them on!" I
protested. "Besides, wouldn't this seem like more a costume for your
son?"
"Yes. Do you really like wearing that outfit that much?" she shook her
head to show she wasn't really expecting me to answer. "Well, daughter or
son, you are 14 and there is no way you are wearing that."
"Great, so the one thing that has pants is no longer an option even
though it looks great and would work as a good costume."
She reached behind me lifting the skirt and running a finger across the
bottom of my bottom below the shorts. "No, not appropriate for a 14 year
old and especially since you are going to be walking your brothers and
sisters. I am taking this option away.
"So, we have eliminated the two long dresses and the hot pants," she went
on.
I watched her eyes as she talked, she couldn't stop eying my legs and I
was feeling a little weird about it. I think she was too because she kept
trying to look away at other things.
"Which of the dresses do you like better? The black or the red?" she
finally asked as she looked at something on the table.
"I think I'd rather go with the red dress. The black is very tight, a bit
short and I'm not sure I can be out in public in it. It is going to be
tough enough wearing the red dress." I offered.
"The black is too short but you want to wear the hot pants? That doesn't
make a lot of sense to me but I can go along with the red dress. It makes
sense," she nodded. "Follow me."
We went to her bedroom and she started going through her lingerie
drawers. She pulled out a red bra, black panties and pantyhose. She
examined the hose, put them back and selected another pair.
"Here, take these and change. Bring all the clothes back in here and I'll
put them away," she commanded. "Oh, and don't stuff the bra yet. I have
an idea for that."
I returned to my room and stripped down again. I put on the bra and
panties and as I put on the hose I noticed they had a fake seams running
up the backs of the legs. I did my best to get them straight; I then put
the dress on. It seemed odd looking down at the front of me now with a
dress and no boobs but I was certain that would be resolved soon.
I put the rest of the clothes back on their hangers, gathered the used
underwear up and took it all back to my mother's room. I laid it all on
the bed and noticed a pair of black high-heeled shoes beside the bed. The
heel appeared to be a bit higher than the boots and a lot narrower. I sat
on the bed and slipped them on. There was an ankle strip and it took some
work but I finally got them buckled up.
Just as I stood up my mother came back into the room.
"Oh, good, you found them and they fit. Can you walk in them?" she asked.
I took a couple tentative steps and my ankles threatened to betray me but
I persevered. It didn't take long before I was able to walk around the
room without worrying about a trip to the emergency room.
"I think you are going to need this too," she stated as she reached into
the closet. She pulled out a black half-slip with the top part a solid
silky material before it spread out in a stiff netted material. "It will
make the skirt stand out some, like the old poodle skirts, but not as
dramatic."
I took it from her and put it on getting it all the way up to my waist.
It was a challenge trying to do it in the heels but I managed without
killing myself. I pulled the dress back down straightening it over the
slip. It had more volume but it wasn't over kill.
"Ok," mom started as she began unbuttoning the front of my dress, "now we
fix your chest."
She had brought a couple of sandwich bags, the type that fold over
themselves to seal, and filled them with sugar. Placing a bag in first
cup she molded it against my chest and into the cup of the bra. She added
a bit more sugar from the other bag and after pulling the front of the
dress open and closed a few times and adjusting she finally decided it
looked right.
"I need more sugar," she announced, "let's go back to the kitchen."
She fixed my other breast and then sat me down on a chair. "Last step,
let's do your makeup."
I sat down on a chair and my mom went to work. She muttered to herself
and said a few things to me as she applied all the various products
instructing me to turn this way, turn that way, open your eyes, close
them, blink them, and purse your lips.
Just as she was finishing up, Joann, my mom's best friend, came into the
kitchen. We rarely locked the doors during the day because of the kids
playing outside and Joann rarely knocked when she came to visit.
"What are you up to?" she asked as she sat in one of the chairs. "She's
pretty, isn't that your dress she is wearing?"
My mom didn't reply, she just looked at me, "OK, that should do it. Stand
up and give us a spin. I want to see how it all looks."
I nervously glanced over at Joann. Joann was a knockout. She worked at a
bar near downtown and was obviously on her way to work. She had long dark
hair that was lightly curled and reached down to her ample bosom. She had
on a turtleneck sweater and tan shorts, they covered about as much as the
ones as I had worn earlier. Dark hose and knee high boots covered her
long legs. She smiled over at me, and then her eyes narrowed a bit as she
tried to figure out who I was.
I stood and moved to the middle of the room. I lifted my arms and did a
little pirouette just quick enough to make the skirt fly out a bit. When
I had done a complete turn I looked back at my mom.
"Well, I think you look terrific," she smiled, obviously taking some
pride in her work. "Joann, what do you think?"
"I said before that I think she looks very pretty. Earrings and a
necklace are a definite need. Your dress looks good on her. Maybe open
the collar a bit more to sex it up a little."
"No, that won't work. Boobs are bags of sugar, can't let them show at
all," she answered trying to suppress a smile. "But you are right about
the jewelry, I'll be right back."
Joann's mouth dropped open. "Tony? Is that you?"
I smiled and gave her a little curtsy.
"Oh, my! That is unbelievable! Walk across the kitchen for me, let me get
the full effect," she gushed.
I did as instructed. When I got back to my starting point I asked, "Do
you mind if I go look at myself? I haven't seen a mirror yet?"
"Go use the one in my bathroom," mom responded as she returned. "And put
these on while you are at it. She handed me a necklace with a pendant and
clip on earrings.
I left in a hurry barely able to contain myself. I wanted to run but
didn't dare take a chance on the heels I was wearing.
I snapped on the light at I entered the bathroom and positioned myself in
front of the mirror while staring at the floor. I closed my eyes and
raised my head. Taking a deep breath I opened my eyes.
I was shocked. I didn't see myself at all in the mirror. My mother had
done an incredible job on the makeup. I looked older, closer to 25 than
14. The dress helped to make me look older as well. I twisted back and
forth looking at my profiles and feeling the slip swish around my legs. I
ran my fingers through the blond hair coming down over my shoulders and
just stared at myself.
"Are you coming back sometime today?" my mother called.
"Just a minute!" I called back and put the necklace around my neck. It
wasn't very long so I was able to have it under the collar of the dress
and be visible above the opening of the dress. I snapped the earrings on
to my earlobes.
With one last look I turned and went back to the kitchen. I noticed the
clock as I was going through the bedroom and realized it was only 4:30.
We wouldn't be leaving for another 2 hours.
I got back to the kitchen and took a seat while my mom and Joann
continued to chat. Mom was describing how I looked in the various
outfits.
"Well, Tony, I think you are an incredibly good sport to allow your mom
to do this to you. I know a lot of boys that just wouldn't stand for it.
I wish I had gotten here at the beginning of the trying on though, from
what she tells me her hot pant suit was something to see, even before the
makeup."
"Apparently, I didn't see myself but she was adamant that I couldn't wear
it. Said it wasn't proper for a 14 year old. I thought it at least had
pants and might be a little better for being outside." I gave my mother a
look trying to decide just how much Joann might have been told.
"She bragged that you looked good in everything. I hope maybe the next
time, if there is a next time, I'll get to be here for the whole tryout."
She gave my mom a wink. "Hey, maybe I have a thing or two to contribute
to the effort!"
"Halloween is already taken care of this year." I pointed out. "I don't
want to think about next year yet. I may decide not to be so good a
sport."
"Your mom said she had a really good time doing this with you today. I'm
sure she'll want to do it again. I hope you have fun and are up for it."
She gave me another radiant smile.
I listened while the two of them talked, occasionally picking at
something on my dress, trying to think of something I could do while
waiting to take the kids trick or treating. They would be coming in soon
for dinner and to get into their own costumes. I noticed both ladies
glancing over at me regularly.
"Hey," Joann said, "I forgot something at home. Tony, would you like to
take a ride with me back to my place? It will only take a minute or two.
You'll be back for dinner."
I looked over at my mom who nodded. "Sure, I'll go." I wondered why she
wanted me along.
We got into her car and I gathered the dress into my lap, careful not to
get it caught in the car door when I pulled it shut. The ride over was
short, she lived about five blocks away, and I didn't say much in
response to how much she couldn't believe it was really me. We got to her
place and reached for the door handle. Before I could open the door she
laid a hand on my arm.
"My neighbor is here watching my kids," she started. "She's about your
age, might even go to your school. I want to see if she can see you are
really a boy. I'll call you Teri. Can you soften your voice a little?"
I was terrified now. If this got back to school I'd be a bigger target
for the bullies than I already was. It wasn't bad but it sure didn't need
help to get worse. I swallowed and stammered, "I-I-I-I can t-t-try."
Joan smiled. "Just relax. You fooled me, you'll be fine."
She opened her door and got out of the car. I did a very unfeminine thing
and stared at her ass and legs as she climbed out of the car. I felt a
little better. I took yet another deep breath, got out of the car and
followed her to her door.
We walked in and I saw the girl sitting on the couch. I recognized her
immediately as a girl from my homeroom. So much for maybe knowing her, we
saw each other every day.
"Oh, Joann!" she squeaked. "You scared me. I didn't expect you back so
soon. Everything ok?"
"Oh, everything is fine, I just forgot something," Joann answered waving
a hand as though brushing something away. "JJ, this is Teri, a friend
that lives over by Marie. Teri, this is Judy Jamison, we call her JJ"
JJ waved, "Nice to meet you."
"And you," I answered.
Joann smiled and went to the bedroom to retrieve whatever it was she
forgot.
I stood there trying not to look at JJ counting the seconds until I could
get out of there.
"Would you like to have a seat?" she offered.
"No, thank you, I'm fine."
"That's a pretty dress. Red is a good color for you, goes with your hair
and complexion so well."
I just smiled and nodded as Joann came back in the room.
"OK, we are gone again. Thanks JJ, be careful taking the kids tonight.
Are you going to dress up to go with them?"
"I don't think so. I'll probably just go as I am. I'll stay right in this
neighborhood so there shouldn't be any problems. It's really too late to
put something together."
Joann laughed. "I was talking to Marie. Her son said the same thing so
she stuck him in one of her dresses and made him up. He looks pretty
good, too."
I reacted by whipping my head around to look at her and my mouth dropped
open. I almost said something out loud but caught myself just before it
came out. Too late though, I'd blown my cover.
JJ looked at me, then back at Joann. "Tony?"
"Yeah," I answered looking down at the floor but not before trying to
give Joann a dirty look. "Listen, JJ, please don't say anything at school
about this. You know how bad it can get if this gets out."
JJ snickered. "No, I won't say anything. But this is amazing. If you
hadn't jumped when Joan talked about Marie's son, you, I wouldn't have
made the connection."
"Listen," Joann started, "why don't we grab the kids and their costumes
and take them back over to Marie's? You guys can walk the kids together."
"I'm sure the last thing she would want to do is walk the neighborhood
with me looking like this," I offered.
"Actually, I would like it. And I have an idea for what I can do for a
costume. Joann, if you can get the kids together I need to run home for a
minute."
"No problem, be back here in 10 minutes. If you need you can change over
at Tony's," she said. "I am going to have to drop you and head straight
for work."
JJ hit the door on a run.
"Sorry," Joann offered. "I really didn't mean to expose you that way."
She called for her two kids.
I called my mom and explained what was going on while Joann got her kids
changed and ready to go. Ten minutes later we piled into Joann's car and
headed back to my house. Once there we got out and Joann drove off.
We ate some dinner, my mom got the kids changed and then fixed my
lipstick, JJ went to the bathroom to put on her own costume.
JJ had decided to keep the theme in play. She dressed in a man's suit and
had penciled in a mustache. It was a bit big on her but she didn't have
the help I had gotten during the course of the day. Her hair was short
already and she gelled it down for a slick look, tucking the little extra
length she had down the back of her collar. She looked pretty good
considering.
My mom insisted on taking pictures of everyone before we left, of course
a couple of them were of JJ and me together. We finally hit the road.
We walked the kids from house to house and talked a little about school,
the teachers and the other kids. We talked a little about what we did in
our free time. Not much and a lot of it interrupted by needing to call
out to keep the little kids from running too far ahead, or warning them
not to eat the candy before we could get back to the house and check it.
During the quiet moments I found myself thinking I could have been
comfortable in any of the outfits I had tried on earlier and wondering
what JJ's reaction might have been to them.
As we walked away from the last house we let the kids run ahead back
home, JJ stopped walking. I stopped and turned to face her.
"Would you be honest with me if I asked you a question?" she spoke so
softly I barely heard her.
I looked around to see that we were alone. "I think so."
"Do you like me?" she asked looking off at other things in the area.
I laughed. "Yeah, I like you ok. You spent the whole night with me
walking kids around with me dressed like this," I twisted back and forth
a few times making the dress shake, "and didn't give me a hard time about
it or make fun of me or anything like that. We've had a nice talk, I
think. Actually, I was thinking I might like to hang out with you at
school if it would be ok with you." It was my turn to find something
interesting on the ground. I pressed my dress back against my legs so I
could look at my shoes. I was happy I had managed not to scuff them up.
JJ looked at me and smiled, "That would be really nice. But why did you
laugh?"
"Because I was afraid of what question you might choose to ask. That one
was an easy one to answer."
We turned and walked back to the house and went inside. The kids were in
the living room carefully spreading their candy out for examination. My
mom would eliminate anything remotely suspect of being able to be
tampered with.
I sat on the couch, JJ sat down beside me, close but not too close.
"Are you ready to get out of those clothes yet?" mom asked me.
"Oh, I'm just glad to get off my feet. These shoes are just a little bit
on the small side and they make my feet hurt. I'll change in a minute," I
answered. Turning to JJ I offered, "if you'd like to go change that would
be ok. I'll be here when you get back."
"OK. I'd like to do that. These shoes are hurting my feet as well," she
said as she stood up. "And I don't think it is just because you think
your shoes are small. Welcome to a girl's world. Shoes like those hurt if
you spend a lot on time on your feet."
"OK," my mom called, "everyone get your candy picked up and in your bags.
My kids, go get ready for bed, school tomorrow."
I watched as they all complied. Leaning forward, I pushed the dress down
between my legs as I spread my knees and reached for an ankle strap. Once
the shoes came off I lifted my feet and spread my toes, examining them
through the dark nylon that webbed them together.
"You seem quite comfortable," my mom observed. She had taken a seat in a
chair on the other side of the room.
I let my feet drop back to the floor and evened the dress out again.
"Well, actually, I am," I glanced back up the hall to be sure JJ wasn't
coming back. "I'm glad I did this, you did this."
Mom glanced at the clock, "Your father will be here soon. He is going to
honk so JJ and the kids can be taken home. We'll talk a bit more after
they go and before he gets back."
JJ returned and sat on the couch with me again. We chatted about some of
the costumes we saw on others during our travels that evening. After just
a few minutes we heard the car horn and they headed on out the door.
"I'll see you tomorrow at school," I called to JJ.
She turned and waved.
I grabbed the shoes and went to my room where I stripped off the wig,
jewelry and all the clothes. I threw on a pair of shorts and a t-shirt
and headed for my mom's room to return all her stuff. In truth I was a
bit disappointed it was coming to an end.
We headed for the bathroom where mom went about disassembling the
masterpiece she had put together.
"So, was that enough? Are you still going to be prowling through my
things?" she asked. "And please don't lie to try and spare my feelings or
because you're embarrassed. I figured it out once, I'll know again."
I hesitated before answering. I finally decided the truth would be the
best course. I waited a bit longer until she finished scrubbing around my
mouth.
"Actually, I wish it had gone on longer. Once I got over the fear of what
someone might say or do and relaxed I had a great time. I loved the
feeling of the clothes I was wearing. I loved the fact that someone
thought I was actually pretty," I confessed. "I can see wanting to do
this again next year. And, I can try and not got through your things, but
sometimes my curiosity gets the better of me."
She stopped cleaning my face and looked me in the eye for what seemed
forever. Then she nodded and went back to cleaning. "Do you think JJ is
going to be a girl friend or just a friend?"
"I'm not sure yet. Just a friend for now, we only spent a couple hours
together but we will probably be spending a bit more time together at
school now."
"I'm also trying to understand," mom went on. "I guess I am trying to
figure out if you are gay, or want to be a girl, or what. I'll support
you in whatever you are, some choices will make life a bit tougher but
you've got to be happy with yourself."
"Well, the way I feel right now is that I am not gay. The idea of
touching another guy kind of grosses me out. But at the same time I like
wearing the pantyhose and the dresses and all the other stuff too. I've
seen pictures of girls in stockings with garters that I'd like to try
some time. I've seen other things that I don't even know what they are
called but they look sexy and sleek and I bet they would feel great to
wear.
"Thank you for making me do this tonight. I had a really good time." I
fell silent.
"OK, first, I am glad you enjoyed yourself but now I am not certain I
made the right decision in having you do it. Maybe if I hadn't your
curiosity would have eventually died out. But, what's done is done.
"Second, do not expect me to be buying you things, or buying myself
things for you to wear. I need to put some thought into where things are
going to go from here.
"Last, your father will not appreciate this. I was trying to decide if I
was going to tell him about you secretly trying on my clothes but now I
think I'll let it be just between us. Tonight was just an idea I had and
it seems you have made a new friend thanks to Joann."
We heard the door as my dad got home just as mom finished removing all
the makeup. We left the bathroom and I said good night to both my folks
and headed off to bed. It had been a long day for me but I couldn't go
straight to sleep. I lay there reflecting back on the afternoon and
evening for a long time. Eventually I did manage to get to sleep.
Chapter 2
The next morning everything was back to normal. I got dressed in my
normal boy clothes and after breakfast walked to school. I thought back
on my night and remembered how the breeze felt against my legs. I also
remembered how my feet started hurting in those high heels.
I got to school and headed for my first class, homeroom didn't come until
mid-morning so I didn't expect to see JJ until then. Others in the class
were talking about the previous night, some had sibling duty like I had,
others thought it funny to terrorize the neighborhood egging houses or
covering them in toilet paper. Nobody admitted to dressing up.
I finally got to homeroom and picked a seat. This was a short period used
for announcements and other things, only 20 minutes. More kids rolled in
taking seats around the room and finally I saw JJ come in the door. She
took a look around the room spotted me and went to a seat on the other
side of the room. I felt a sickness settle into my stomach. The
announcements went by without my hearing a word. The bell rang and I went
off to my next class.
The end of the day came around and I headed out the door and down the
block, as I turned the corner I almost ran over someone. I looked up and
JJ was standing there.
"Hi, Tony," she started. "I thought I ought to explain something. I don't
want you to get the wrong idea."
"I already have an idea," I snapped. "why don't you explain and I'll tell
you if it is wrong or not."
She jumped like I had slapped her. I didn't mean to be so rough about it
but I was feeling very hurt and was certain my high school life was about
to become hell.
"I tried to catch you before you got into first period this morning but
you were too quick. Tracy, in homeroom, saw us last night. She recognized
me but not you. She wanted to know who I was with but I told her it was a
neighbor who asked me to help her with her kids since I was going out
with Joann's. I was afraid if I suddenly sat with you today she might
start asking questions about when we started becoming friends, get caught
with different stories and then she might figure it out. And you know
what a big mouth she has. I'm really sorry."
I felt like crap, a different kind of crap. How can you go from feeling
bad to feeling bad and it is two different kinds of feeling. Add it to
the list of things I really just don't understand.
"No, I am truly sorry for snapping at you. Thank you for trying to
protect me, I really do appreciate it." We started walking down the
street. "So, do we find a way to start hanging out at school or blow it
off?"
"I still want to find a way to hang out. We have too much time left to
ignore each other for that long. I really enjoyed talking the other night
and want to be able to talk more." She confessed.
I ended up walking her all the way to her house while we planned to
gradually get to know each other.
* - * - *
The next day I took an extra-long time getting to homeroom so that when I
got there the choice of seats was limited. The plan was to try this
during the week each day until we were forced to take seats next to each
other. JJ had arrived a minute before me and chose a seat with a couple
empty seats around it. We got lucky the first day so I went and sat next
to her.
I always tend to be the class clown and announcements are usually good
fodder. An announcement came on about a mandatory pep rally that would be
held Friday afternoon and I made a point of saying they had to be
mandatory or nobody would attend them. JJ immediately came back saying
everyone should want to go and support the school teams. We exchanged a
few more points when right on queue the teacher told us to be quiet so
they could hear the rest of the announcements.
"Fine," I answered, then turning to JJ, "where is your next class?"
"Why?" she responded acting a little leery.
"Because I think this might be a fun little debate and I want to continue
it," I countered.
JJ looked around at the others gauging their reaction. "306"
"OK, I'm in 202. I'll walk you to your class then can drop down the
stairs to mine," I smiled. "Unless you would rather concede the
argument."
"I'm not conceding anything," she replied sitting up a bit straighter.
The announcements ended and the bell rang. I grabbed my books and jumped
back into the debate with JJ. We continued it down the hall until we got
to her classroom. Nobody from homeroom was around any longer. I gave JJ a
wink and headed down the stairs.
Lunch rolled around and I was sitting in my usual spot pulling my lunch
out of a paper bag.
"Do you always eat alone?" I heard JJ's voice come from behind me.
"Yeah, just never seemed to fit in with anyone," I answered.
"Well, why don't you come over and sit with me and a couple friends?"
I looked at her a moment, this was moving faster than we had planned but
I gathered my stuff up and followed her over to a table where there were
a couple guys and a girl sitting. Introductions were made and JJ told
them of the debate we had that morning.
As lunch ended I thanked them all for allowing me to join their table and
JJ for inviting me. They all insisted I join them again the next day. I
walked away feeling as great as I could feel. The rest of the day flew
by.
I left school walking quickly down the street and when I turned the
corner I literally ran into JJ. I managed to grab her arm to keep her
from falling down.
"Hey," I said, "we really need to stop bumping into each other like
this."
"I think you bumped into me."
"Well, you shouldn't be hiding behind bushes. What's up?" I asked.
"Not much, I just had such a good day today and everything went even
better than I had hoped I wanted to have you walk me home again," she
beamed.
"I can do that," I smiled back. "But tomorrow I am going to fix this for
good."
* - * - *
As lunch came to an end the next day I looked across the table at JJ.
Looking right at her I said, "I want to thank you again for inviting me
to join this little group, I'd like to thank all of you." I looked around
at each of them.
"I was wondering where your last class is, JJ. If you would like, I'd
like to walk with you after school. I know you live kind of on my way
home."
JJ actually blushed a little. "Yeah, I'd like that. Why don't you meet me
by the east door?"
"I can do that," I grinned.
School finally came to an end that day and I headed for the east end of
the building. As I got close I saw JJ standing just inside the door. She
started smiling when she spotted me coming closer. We turned and walked
out the door together.
The next day I left the house a little earlier and went to JJ's house
first and we walked together to school as well.
We spent the next month spending extra time together, even studying
together on occasion though we were in different classes, a couple of our
classes were on the same pace. We talked about everything: music, books,
cars, what we want to do when we grow up, other kids, our lives. Of
course we eventually had to come back around to Halloween night and
whether I would do it again.
I told her how much I enjoyed it but also how much I enjoyed seeing girls
wearing dresses. I liked long hair and nice legs. I didn't care too much
if they had big boobs or not, I was more into legs.
She told me about what she liked about guys. Muscles, but not overly
developed, nicely groomed, tall.
There was no jealousy involved. We were becoming the best of friends. We
talked about everything and kept each other's secrets.
It was a week before Christmas when I got home from walking JJ home from
school and I got to my room and found a bag on my bed. I opened it and
inside was a package of panties and four packages of pantyhose of various
hues. There was a note:
Tony,
I am giving you these items for your use. I've decided that it isn't
going to do you any harm to have them. I've also decided I would like for
you to stay out of my lingerie drawers but may borrow from my closet if
you need as long as things get back as quickly as possible. You should
keep these things hidden. If you absolutely need something more let me
know and I may accommodate you.
Also, I know you and JJ are spending a lot of time together now and if
you decide you don't want these things leave them in the bag on your bed
tomorrow morning and I will return them.
Love Mom
I went to my closet and looked around. I found a box that I stored old
calendars in and carried it to the bed. I opened the packages and added
the contents to the box then put the box back in the closet on the shelf.
Nobody else should be going into that box for anything. I took the empty
packages out to the trashcan in the back and pushed them down into the
existing trash.
Later that night I caught my mom's eye and gave her a smile and a wink.
She gave a little nod in return and we had an understanding.
JJ and I got through our freshman year together and got our schedules for
the next year managing to arrange it so we shared a few classes together.
We were spending a lot of time together but we were still treating it as
a friendship. I was starting to look at her a bit differently, though,
and I think she was making some changes to help me.
I noticed after Christmas she started wearing more skirts and dresses to
school. When I asked about it she said she got a lot of new clothes under
the tree and decided she liked dressing a little nicer. Her hair was
getting longer as well.
I hadn't told anyone, even JJ, about the care package my mother had left
me. I was making use of it when I could and I was in the mood. And I kept
to our arrangement, borrowing clothes only and putting them back as soon
as I could.
Life was good.
Chapter 3
Here it was, October again. I was really looking forward to it this year
again hoping it would be as big a thrill as last time. I was preparing
for it and I wasn't afraid of all the "what ifs" I was confronted with at
the last moment last year.
Halloween was going to fall on Tuesday this year and that meant rushing
home after school and getting changed in a hurry. My mom suggested
picking out the outfit Sunday afternoon so we would have that taken care
of. That would allow us to get right to work Tuesday evening when I got
home.
Sunday rolled around and the kids all got sent out to play. JJ and Joann
both showed up to help me decide on what to wear. Joann contributed a
couple outfits to the cause. My mom collected a few of hers and a bra,
something she hadn't provided for my stash. I would be wearing my own
panty and hose.
By popular demand I modeled the hot pants suit first. The boots barely
fit my feet and I am not sure the skirt actually reached the bottom of
the shorts any more. It was really close. But the looks on all the faces
told me I could still pull it off if I wanted to. And that my mother felt
the same way about letting a 15 year old out of the house as she did the
previous year. I just smiled and went back to try something else.
The little black dress was back and I changed hose to a dark pair and
went back to the kitchen. I had practiced over the last year and found I
could conceal the extra bulge fairly well. I got some appreciative
comments from the ladies.
My mother had provided a new long dress she had gotten. Nude hose again
(I should have grouped the clothes so I wouldn't need to keep changing).
It was floor length, very gauzy in three layers in the skirt, the top
looked like a wrap around and the sleeves just draped over the tops of my
shoulders. I absolutely loved it but it was totally wrong for Halloween.
I went back to the kitchen.
"OK," I told them, "first I absolutely love this dress. But I think it is
totally wrong for Halloween. Definitely a spring dress."
JJ and Joann just looked at me for a minute. "I think you might be
getting a little carried away here, Tony," Joann stated. "This is a
Halloween costume after all."
"Yeah, right," I laughed. "I just got lost in the moment. Last year was
terror but I had fun. Joann, you said you hoped I enjoyed myself and
would want to do it again. I was actually looking forward to it. Anyway,
I better try something else."
I got back to my room and took the dress off. I wondered if I had really
messed up but I decided to not let it get to me. I looked through the
dresses still yet to try and decided to go with a mini-dress that Joann
had brought. It was a lot of crazy colors and sleeveless. Reminded me a
lot of a 60's go-go dancer. Would work well with the white boots I wore
earlier.
"Well?" I asked.
"That is awful short," mom pointed out. "You won't be able to sit down!"
"No, you just have to be very aware of what you are doing," Joann added.
"I've worn it a few times. Of course, you could put a pair of hot pants
under it."
JJ blushed a little.
"Next!" I turned and left.
The last outfit was actually a blouse and skirt. The skirt was a brown
leather mini with fringe, the blouse was mustard yellow silk with big
billowy sleeves. I got them on and returned to the kitchen.
"Well, that's pretty nice and the skirt is just long enough," my mom
observed.
"Actually, I think you need more chest for that blouse," pointed out
Joann. "You can't see that there is anything there, it just kind of hangs
there."
"Well, this is what I have to work with," I pointed out.
"No, I don't think so. I'll be right back," Joann spoke as she left the
room.
She came back just a minute later.
"Here, try this on," she handed me a bra.
I just stared at it for a second and looked at Joann. I realized her
breasts were moving more freely under her shirt and I could see dimples
in the fabric caused by her nipples. She had removed her bra to give to
me.
She was as observant as I was though. "Yes, I took it off for you, and
I'll take that new lump in your skirt as a compliment. I guess we know
that girls turn you on. Now, go on, let's give you a bigger chest."
I started to leave the room but they stopped me. No reason for me not to
leave the room for the change. I looked at JJ and then I took the blouse
off feeling a bit embarrassed, took the bra I was wearing off and put
Joann's on. We got more material to stuff the cups and I put the blouse
back on. It really did make a difference, making my waist appear a lot
narrower.
"What about shoes with this?" I asked.
"What size were the other boots?" Joann asked.
"8 ?," my mom answered.
"I have size 9 brown boots that work with it. If you think that is the
one to wear this year, you can borrow them," Joann offered.
I looked over at JJ. "What do you think?"
"I like what you are wearing now for Tuesday," she answered. "And the go-
go mini-dress for Saturday."
"Saturday?" I asked. "What is going on Saturday?"
"Oh, I found out yesterday that there is a costume party Saturday night.
We've been invited. I know our friends won't think anything of this for
the party."
"So, I have gotten shanghai'd into another new experience," I moaned.
"What are you going as?"
"I haven't decided yet," she giggled. "But, now that I know what you are
going as I'll find something appropriate."
"OK, all decided. I need to get back home," Joann said as she started for
the door. "You can return all my stuff next week, perhaps when you come
by to pick up JJ for the party Saturday."
* - * - *
I got home from school Tuesday and rushed to change clothes. Once I was
dressed I headed for the kitchen so my mom could do her magic once again.
This time she went through the steps and explained why and how she was
doing each thing.
"You are going to do your own make-up for Saturday," she explained.
"Are you upset with me?" I asked.
"No, I just think this is going further than I expected. If you are going
to keep doing this, then I think you should know how to do it for
yourself."
She finished up and I headed for the living room to wait for JJ to
arrive.
When she did arrive she wasn't wearing a costume.
"Do you need to change?" I asked.
"No," she murmured. "I just decided not to dress up tonight. I'll save it
for Saturday."
"Do you still want to walk with me?"
"Yes! Sorry, just not in the mood for a costume tonight just to walk
around the neighborhood."
"OK, well why don't we gather the kids and hit the street?"
We trouped on out the door, once again shepherding the kids from house to
house. It was chillier out this year and I was wishing I had chosen a
longer skirt. I couldn't figure out how the breeze seemed to be coming
straight up from the sidewalk at times. I did like the feel of the fringe
brushing against my legs.
"You really like wearing dresses and all, don't you?" JJ suddenly asked.
I almost fell off the heel of the boot as I stepped. I hesitated just a
second longer before answering.
"Yes, I do," I confessed. "Don't you?"
"Well, yes, sometimes. But I'm a girl! I'm supposed to be wearing
dresses, high heeled shoes, pantyhose. Are you wearing panties too?" she
asked.
"Yes, my regular underwear wouldn't look right under the dresses, too
heavy, thick seams. No shorts either, this skirt is too short."
"Last year were you wearing shorts under that dress?"
"No, all women's wear." I was not feeling as chilled as I had been.
We walked along in silence for a while.
"I don't understand this. All year long everything seems normal. I
thought maybe," she suddenly stopped.
"Thought what?" I prodded.
"Thought that you might want to be more than friends one day," she
hesitated. "With me."
"Really? Because I confess that there were several times that I wanted to
take your hand when we were walking home, or even see if you would let me
kiss you," more confessions. "I like our friendship and was afraid to
push it to another level because you would not want me to."
"Uh, really? I've been just waiting for you to give me any kind of an
indication for the last half a year," the exasperation evident in her
voice.
"I'm sorry. The first time you really talk to me I'm in a red dress. I
was thrilled to have you as a friend but afraid if I said or did
something that got you upset with me you might tell someone about it.
Because for me it was more than that one, well now two, nights. The
panties and hose I am wearing are mine. I occasionally borrow clothes
from my mom's closet when I'm alone because, as you guessed, I like
wearing women's clothes. She figured it out last year and made me dress
up hoping to discourage me from wanting to do it any longer. When that
didn't work she bought me some underthings and told me to stay out of her
lingerie. But she said I could borrow her dresses.
"I'm blurting everything out now. I'm sorry. If you didn't know enough to
hang me out to dry with everyone at school, you do now."
She turned and took my hand in hers and instead of saying anything she
kissed me. I was shocked. It was the first time I had kissed a girl, or
been kissed by anyone not a relative. I wasn't sure what to do at first.
She stood back and stared me in the eyes. It couldn't have been that easy
on her because once she was really looking at me she saw eye liner, eye
shadow, lipstick, etc.
I leaned in and kissed her back. Our arms wrapped around each other.
The kisses weren't bad for a first effort. A first for her as well I
found out later. They were old style movie kisses, closed mouth, but they
lit me up.
We leaned away a little, still holding on.
"I'm not sure how I feel," JJ started, "first the kiss felt nice, even
with your lipstick, which I sometimes wear but not now. And I found
myself thinking the blouse feels really nice and wonder if it would fit
and I could borrow it. It's so confusing."
We started walking again and just before we got back to the house I
stopped. "JJ, what about Saturday? Do you really want me to wear that
short dress?"
"Would you rather not? You've confirmed what I was thinking, which was
that you might like wearing dresses, and that was my favorite for the
party."
"So, yes, I would like to but I don't want to push you into thinking I
have to dress up like that because it is a costume party."
"No, I want you to wear that dress. Actually, it got me a little turned
on when I saw you in it." She turned away as she said it, I was sure she
was blushing. "Still more confusion."
"OK. What time shall I pick you up?"
We settled the arrangements as we walked back into the house. I went to
the bathroom to clean off the make-up and noticed my lipstick had gotten
smudged. JJ waited in the other room while I changed into my regular
clothes. She had ridden her bike over to the house and I was going to
follow her back on my bike.
* - * - *
I spent the week after school in my room practicing wearing the mini-
dress. I set up a mirror across the room so I could watch myself sit and
see if I was flashing anything. By the time Friday rolled around I was
pretty good at everything.
Next test came Saturday, time came for me to get ready and I got
completely dressed this time with stuffed bra (mom's), wig and jewelry. I
sat at the desk in my room with a mirror and tried putting on my make-up
by myself for the first time. I had several do-overs as I had to clean up
mistakes. After about 90 minutes I looked in the mirror and decided I had
done as best I could. I went and looked for my mom.
"You did pretty well," she nodded approvingly. "I think you'll be fine,
at least as far as make-up is concerned. Are you sure you can manage that
dress? There isn't a lot of room for error and you are going to be in a
room full of other kids."
I smiled and walked over to a chair. Giving the dress a little tug and
laying my hands atop the gap between my legs as I sat dropping lightly
into the chair. I turned my knees slightly away and with another tug on
the side crossed my legs.
"OK," she smiled. "Looks like you have things well in hand. Have a good
time tonight. No drinking! Or drugs!"
"Yes, Mom." I gave her a hug. "I promise."
I grabbed the rest of Joann's clothes up and put them carefully in a
shopping bag, including her bra. I decided to walk over to JJ's house. It
occurred to me how much had changed in the last year as I walked. It was
still light out as made my way down the street. I was also aware of how
tight the white boots had become after the slightly larger boots I had
worn earlier in the week. This would be the last time I would be wearing
them.
I was about 2 blocks from JJ's house when a car full of boys, probably
from my school though I didn't recognize any of them, rolled past hooting
and hollering at me. I ignored them and continued along until I noticed
they had pulled over just up the street. Either they had business there
or they were waiting for me. I decided I'd rather not find out.
I walked past the house I was in front of and up the stairs of the next
house. I had no idea who lived there but felt it would be better than
facing the boys. Fortunately, the house had two apartments and the front
door was to an entryway that housed the front door of the downstairs
apartment and the stairs up to the other apartment. I stood inside and
tried to see through the beveled glass window at what the car was up to.
After about a minute and a half that felt like an hour I saw someone go
across the sidewalk to the waiting car, he got in and they drove off. I
hadn't realized I was holding my breath until I let it out.
I opened the door to leave just as the door to the downstairs apartment
opened.
"What do you want?" a lady who looked to be in her 80s screeched through
the crack in the door.
"Nothing, wrong house," I answered trying to keep my voice soft. "Sorry."
I went out the door and down the stairs as quickly as I could before she
could ask me anything more. As I turned up the street I saw the curtains
part out the corner of my eye but I didn't turn to look, I just kept on
moving down the street.
I finally arrived at JJ's place. I knocked on the door and her father
answered.
"Tony?" the disapproval evident in his voice. "Is that you?"
"Yes!" I waved, "it's me."
"Come in, JJ is almost ready." He turned and left me there without
another word.
I was looking around trying to figure out what to do when JJ came around
the corner. We were practically twins.
"Oh, my God!" I cried. "You look great!"
"Both your dresses are too short!" her dad hollered from the other room.
"You had better not be getting up to no good tonight. I'm not old enough
to be a grandfather."
"Dad!" JJ blushed, clearly mortified by his remark.
"Not to worry, sir," I called back. "I'm not ready for that
responsibility either."
"Be back by 11:00 or I'll come looking for you."
I just looked at JJ. She sighed, took me by the hand and we left. The
party was only a couple blocks further down.
We arrived and everyone was shocked, as much at JJ as me I think. She
usually dressed rather conservative and not a lot of make-up. Tonight her
dress was every bit as short as mine, and her make-up made her look in
her 20s. I had a hard time taking my eyes off her.
We talked with everyone, danced a bit (almost a requirement for the go-go
dancers), ate snacks and had a generally good time. Someone snuck some
beer in but I wasn't interested.
JJ came up beside me and wrapped her fingers in mine while I was talking
to someone.
"I think we better go before my dad comes looking," she whispered.
I nodded to her even though I noticed it was only 10:00. It wouldn't take
more than 15 minutes at a slow walk to reach her house.
"It looks like you two have become an item," Brian observed. "Holding
hands, matching outfits. How did you talk him into it JJ?"
"He just couldn't pass up the opportunity to see me in a short dress and
this was the only way I would do it," she answered as she tugged my arm
toward the door.
"It was just a matter of time before you two made it official," Brian
called after us. "See you in class."
We waved and walked out the door. I waited until we got a couple houses
away before I said anything.
"Everything OK? We left a lot earlier than we needed to," I put my arm
around her waist pulling her closer to me.
"Yeah, everything's fine. I just wanted a little time to ourselves," she
laid her head over on my shoulder.
We walked along a ways and I suddenly felt her hand slip down off my
waist.
"What are you doing?" I pulled away a little.
"I want to see your panties. I'm curious. I watched you all night and you
worked that dress well, and believe me I know how hard that is. I could
feel some of the boys at the party trying to get a peek at mine all
night."
"So you think I'm going just pull my dress up right here on the street?"
"No, of course not. I just said I wanted to see them, I didn't say I
expected you to show them to me," she pouted a bit.
I put my arm back around her letting my hand wander down. "I'll show you
mine if you show me yours," I answered.
"That is really juvenile, you know?" she shot back. Then, after a minute
she said, "There is a park just a block from here. Let's go by there
before you take me home."
We walked to the park and saw it was deserted. There was a playground
with swings, jungle gym, slide, and concrete barrels. We sat on the
swings facing opposite directions talking for a few minutes. I reached
out and grabbed the chain on her swing and pulled it closer. Leaning over
I kissed her, I didn't rush it and after a minute I let my tongue slide
between my lips and touch hers. She jerked her head away.
"What are you doing?" she exclaimed.
"I was trying to kiss you. It seemed like the right thing to do," I
answered defensively.
She looked at me for a minute. "OK, try again."
Our lips met again and I slowly let my lips part and touched her lips
with my tongue. She parted hers and I pushed it further in her mouth. Her
tongue touched mine and then slid around it caressing it. I felt a small
fire light somewhere inside me. Then I felt her hand on my thigh, barely
an inch from touching my panties and all that was there. I intensified
the kiss from my side and pulled the swings closer together. I dropped my
hand to her thigh feeling the silkiness of the nylons, but my fingers
brushed higher that I had planned. She seemed to take this as approval as
her tongue surged forward into my mouth and her finger lightly rubbed the
front of my panties and the erection that lay beneath.
She snatched her hand back quickly and broke off the kiss.
"I'm sorry. I was just curious about what kind of panties you were
wearing. I didn't mean to get you all excited," she rattled off the words
so they almost ran together.
"It's ok," I assured her. "I get excited a lot when I wear dresses, and
when I kiss you, too. I really didn't mean to touch you that high. Think
we ought to stop?"
JJ nodded. Then she looked around and seeing we were alone she backed up
like she was going to try and swing up high but stopped and raised her
dress up displaying a pair of pink cotton panties with a little lace trim
at the top under the sheer hose. I couldn't stop myself from staring at
her. I could see a slight indention from the lips of her vagina. I wanted
to reach out and trace my fingers along it. Instead I backed up my own
swing and raised my dress. I watched her eyes as they moved down to take
in the view I was offering. My panties were yellow with a satiny finish.
They were very tight in an effort to keep my dress from getting that
betraying bulge so I was certain she was getting a fairly detailed look
at my penis.
I waited a second longer and then dropped my dress back down. I watched
as her panties slowly disappeared as she lowered her dress. Both our
chests were moving quickly up and down as our breathing had become very
fast.
About that time a car came around a corner on the far side of the park. I
recognized it as the same one from earlier in the evening.
"Come on," I commanded, "we better go. I think there will be trouble if
those guys come over here."
I took her hand and we left the park in the opposite direction from the
boys. A few minutes later her house was in sight. We slowed out pace as
we got closer.
"I liked that kiss," JJ said barely above a whisper.
"I don't think we did too bad for a first try," I answered.
"If we did much better I think we might have gotten into some trouble,"
JJ giggled. "By the way, I like your panties."
"I like yours too." I grinned.
As we approached the house the porch light suddenly snapped on. We both
knew her father had been watching us come up the street. I walked her up
to the door; we kissed briefly and said good night. She went inside as I
started my walk back home. I practically danced all the way.
Chapter 4
We tried to be good over the next year. We kissed a lot. We still were
limited in our privacy. A couple times JJ did some baby-sitting for Joann
and I would go and visit. A few of those times she would give me things
from Joann's closet to wear after the kids were in bed; we didn't do any
more exploring under the dresses, just too afraid of not being able to
stop. But as with most teenagers, that didn't last forever. I wonder if
Joann ever figured out how many of her dresses I wore.
In June I celebrated my 16th birthday. I went out and found a job at one
of the local stores and worked full-time during the summer. I made enough
money to buy myself and old car and be able to treat JJ to a burger and a
movie.
JJ turned 16 early in August. I saved enough to take her out for a nice
dinner. I dressed up in a suit and tie. She was dressed in a beautiful
dress, she looked radiant. Her dad gave me a look when I picked her up
but let us go without any threats. I understood the old threats were
still in effect.
After dinner JJ asked if we could take a drive before going home. We were
still a couple hours short of curfew so we drove around a bit and found
ourselves out at the lake. I went to an area that was void of any other
cars and turned off the engine. I left the radio playing softly.
"What do you think of my dress?" JJ asked as she adjusted the skirt
slightly.
"I think you look beautiful, I told you that when you first got in, but I
don't mind telling you again."
"Thank you," she beamed, "but I want to know how you feel about the
dress! As a guy you take a more unique view than other guys."
I reached over and ran my hand down the skirt feeling the material
against her leg.
"Mmm," I murmured. "I really like the feel of the material; I like the
shape of it and the style.