All for Charity Parts 1 and 2 of 4
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All for Charity (Part 1)
Charlie is volunteered to help with a charity fundraiser at a friend's
salon. Old feelings come back and as does an old crush. Susie from "The
Dress" series makes her return in this story.
Chapter 1
I got home early on Friday, as I usually do. I have time to change from
my work clothes into jeans and a denim Ralph Lauren shirt as I wait for
her to arrive from work. I open a bottle of wine -- a Argentinian
Cabernet, one of her favorites -- to let it breathe before she gets home.
I cut a few slices of cheese, lay out some crackers and check on the
music. All I have to do is set up my materials and we're all ready for
our weekly routine. It is the same routine we've followed since I moved
in with her 18 months ago. One I learned when I was a teenager.
As I start to think back to how I got to this point in life, Tina enters
the apartment. She's dressed in a tailored blue pinstripe business suit,
with a teal blouse. She's worn a suit or dress every day since she
started nine months ago at Darcy's, the fanciest boutique in town. She
is wearing long, geometric-shaped drop earrings, and a matching cleopatra
style necklace. This morning, her shoulder-length brown hair was pulled
back in a neat bun, a few strands sexily flowing over her forehead, the
way she typically wears it. But tonight, it has been let down and
accented by flowing soft curls. That's right, I remembered, Tina stopped
by her friend, Rita's, salon this afternoon to get her hair done. It's
an indulgence, to be sure, but it also is part of her composition. She
is totally committed to her friends, and she loves to spend time with
them. Even if it is for a hair styling that she doesn't really need.
I'd love her anyway, but I especially admire her ability to make strong
loyal friendships.
Rita did a wonderful job. I can't get over how beautiful Tina looks.
With her hair down like that, I can't help but see the resemblence to her
mother, God rest her soul. Tina looks so much like her mother, like my
mother. Like our mother, I should say.
"Our mother?" Yes, even though people often are confused, Tina isn't my
girlfriend; she's my sister. She's my older sister, two years my senior.
I've always been close to her, and she has always taken care of me.
Especially after what happened to Mom and Dad.
I stop myself from falling back into that old story. Instead, I greet
Tina with a hug and a kiss on the cheek. I'm careful not to touch her
hair. I don't want to undo any of Rita's magic. Still, I can't get over
how much Tina looks like Mom -- like Mom did before everything happened.
She is young and beautiful. She's confident and classy. She's about the
age Mom was when she married Dad. Tina still has their wedding picture
in a frame in her room. I've seen that photo so many times, it is almost
etched in my brain, like a visual ear worm, only more soothing and
happier. Tina has Mom's spirit from back then. Not the sad, beat-down
spirit Mom muddled through in her final couple of years, after we lost
Dad. This is the "I'm going to do great things" spirit. One that Tina
carries with her but I can't quite pull off. Maybe that's why I'm 23 and
living with my sister. Something about that spirit, and my admiration,
almost jealousy, of her for it, probably also explains why people often
mistake us for a couple.
I compliment Tina on her hair. She thanks me, and then notices the
bottle of wine. She has an excited glow about her as we sit at the table
for our weekly ritual.
"Wow, Charlie. My favorite wine. You spoil me sometimes," she remarked.
"Well, you look especially beautiful tonight, and a beautiful woman
deserves a fine wine. Nothing is too good for my sister."
Tina leans over and gives me another kiss. "Oh, Charlie. You are
something. But why are you fawning over me? You should be paying
attention to Connie instead of me."
"Connie is at her parents' house this weekend. Anyway, I'm not sure it's
going to work out between the two of us. She's intimidated by you, I
think."
"You're just making an excuse. If you would just try for once, you could
find someone."
"You might be right, but I don't feel comfortable with Connie. Besides,
she will always see you as a rival, and has been trying to drive a wedge
between us since we first met six months ago. She's not right for me."
Tina lets that remark go. She pours us both a glass of wine, takes a sip
from her glass and then lays her hands out on the table. And, with that,
I grasp her hands, look her in the eye and say, "ready?"
When Tina nods her assent, I take her right hand and begin to give my
loving sister her weekly manicure. As I'm removing last week's polish
from her nails, I can't help but laugh a little at the absurdity of that
thought. This is most unusual. Here I am, Tina's brother, painting her
fingernails. This is not something a guy does. Guys don't play with
nail polish. Not normal guys, I tell myself. Nail polish is one of the
quintessential feminine products, like tampons (which have a hygenic
purpose at least) and lipstick. No, painting fingernails is a feminine
activity, despite my joy in doing it. For me, giving my sister a
manicure is a form of relaxation. It is a precise task that requires
skill and patience. It's a great way for me to de-stress, sort of like
those adults who have taken up coloring books recently. The difference
is that my solace isn't child-like; it's just girly.
I should be comfortable with this aspect of my life. But I'm not. It's
still a secret. No one knows. Well, almost no one knows, but that was a
long time ago, and she doesn't live here anymore, not for a while.
Still, in part because of the secrecy, this feels strangely intimate.
But intimate in a platonic way. Tina is my sister, someone I love but
who is not my love interest. Most definitely not a love interest. Tina
is more of a mutually convenient foil for my quirk. She knows I enjoy
painting her nails -- she introduced me to the phenomenon that summer
eight years ago. She's willing to indulge my habit. She also gets a
clear benefit from it; I'm pretty accomplished, if I may brag a little.
In fact, I have to struggle to hide my pride when someone compliments
Tina on her nails. But Tina steadfastly protects my secret -- our secret
-- brushing off compliments with ambiguous statements about how she does
them "at home" not in a salon.
Tina's weekly manicure also gives us time to talk, just the two of us,
away from all the distractions in life. For those 15-20 minutes, Tina is
captive, with nowhere to go and no need to check her phone constantly. I
guess we both get a little solace from this ritual.
I compliment Tina again on her hair. Rita has done a great job.
"Yes, she did," Tina replies. "And you know she's such a sweet person.
She can get anyone in a conversation so easily. You just can't help but
wanting to unload your thoughts and troubles, and share everything with
her. Sometimes, more than you intend, you know?"
I don't know, but before I can ask, Tina continues. "Um, I may have
messed up a little with Rita this time." The pause lingers in the air a
minute. By now, I've finished removing Tina's polish, filed her nails
and fixed her cuticles. I have the burgundy color Tina had selcted in my
hand, almost ready to start her first coat of polish.
"What do you mean?" I inquire hesitantly.
"Oh, Charlie, I'm so sorry. I didn't mean to say anything. I just
slipped. But it's fine, really." She quickly continued, "You see, you
know how Mother's Day is coming up? And you know how Rita always has her
charity benefit at her shop? You know, the two-day event benefitting the
battered women's shelter. They cut the public's hair one day, donating
all the proceeds to the shelter. Then, the next day, they take in the
women and children at the shelter, give them haircuts and make them look
fancy. It's a highlight of the year for Rita.
"Well, this year, Rita is preparing to expand her shop's services. In
addition to hair, she finally is adding manicures at the shop. She
expanded the shop to add four stations, but she's only hired one nail
technicial so far. That's where I slipped."
Tina took another drink of her wine. I took a gulp of mine. I'm still
holding the burgundy polish in my hand, waiting to hear what she did.
"Charlie, I messed up. As I said, Rita only has one nail technicial so
far. She wants to use all four of her stations for the charity benefit;
otherwise the waits for customers will be too long. So, Rita commented
to me that my nails are always so impeccable. She asked which salon I
use, so that she can contact them to see if they will lend a person or
two for the event. 'After all,' she said, 'your nails look professional,
so I know they would do a good job.' That's when I told her that I do my
nails 'at home,' like I always say.
"So then, Rita asks me if I would be willing to volunteer for the event.
That's when I laughed and said, 'I'm such a clutz, I couldn't do
someone's nails!' She asked so quickly, and I responded so quickly. I
wasn't thinking, I mean it. But I knew I had messed up."
"So you told her that I did your nails?"
"I did, Charlie. I'm sorry," she replied, "But it's not all bad. Rita
didn't laugh, she didn't mock me. In fact, she was very accepting of it.
Many men own shops these days, she told me, it's a minority but growing
slowly. She told me that I had the most fantastic nails of all her
clients, so, she didn't care who did them: man, woman or beast. And, she
invited YOU to work her charity event. What do you say, Charlie?"
I grumble that I don't think I will. She pleads with me again, asking me
to at least consider it. "It's for a good cause. Please?" she says.
"Won't you at least consider it, Char?" Only she doesn't say "char" like
in charcoal; she said "chair," as in Charity. Charity, as in my nickname
during my summer of feminine experiences under the enthusiastic guidance
of Tina and her best friend, Susie.
I tell her I'll think about it, as I begin to apply her polish. Two
coats and a top coat give me a lot of time to think. I don't say
anything more to Tina. Instead, I'm lost in my memory of that summer.
Chapter 2
Back in 2008, our life was very different. We were a typical military
family, true red, white and blue all around. Mom volunteered at the USO
while Dad was deployed to Iraq. It was his third tour in Iraq or
Afghanistan, and we missed him dearly. Dad was the glue that held our
family together. He had met Mom when she was only 22 and he was a young
recruit of 25. They married two years later, and Tina was born when Mom
was only 26. Mom devoted her life to supporting Dad and his military
career.
Although Dad had enough seniority to avoid any real hazardous duty, he
steadfastly volunteered for his tours in the Middle East. He only had
about a month left in this deployment when, in February of that year, his
convoy encountered a roadside IUD. Dad's Humvee exploded on the impact,
and he and three others from his platoon were killed instantly.
Dad's death devastated our family. Mom lost her mission, her focus and,
in many ways, her will to live. We were forced to leave our quarters on
base and had to find a new place to rent. We moved out into the outer
suburbs of our town while Mom looked for jobs as best she could. With no
schooling and no paid experience, Mom did odd jobs whenever she could
find them. She cleaned a few houses, jobs she received mostly out of
pity.
When the summer arrived, Mom's sister offered her employment as a
waitress at a new restaurant she was opening. The place was about 50
miles away, and required Mom to be gone late into the evening. But, it
was money, steady pay and, hopefully, eventually a career as a restaurant
manager.
Because of the distance, Mom would stay at her sister's house after work
one or two nights during the week, and most weekends as well. At least
that was the reason we were told. Only later -- after Mom drank herself
to death -- did we learn that Mom was drinking a bit too much and
throwing herself at military types along the way. Our Aunt tried and
tried to help Mom through the grief, but in the end, you can't help
anyone if they don't want to help themselves. Dad's death killed Mom,
plain and simple. It took a year or two to play out, but the deadly blow
was unmistakable.
When Mom was gone, she left Tina in charge. Tina was 17, I was going on
15. I was a bit of a homebody and was going through my own grief process
at the time. So, I spent most of my time that summer following Tina
around. Tina, on the other hand, handled Dad's death much better than
Mom or I. I think she had Dad's confidence and drive (to go with Mom's
looks). Tina also made fast friends with our next door neighbor, Susie.
Susie also was 17, but closer to 18. Susie had lost her father to an
industrial accident when she was 10, so she knew what we were going
through. She and Tina became friends, and I was their collective little
brother.
Given our situation, I should have seen my summer of femininity coming.
Tina and Susie were beautiful, stylish young women. They loved clothes,
makeup and all things you would expect a 17-year-old girl to like. They
tolerated my presence with them, to the point that it almost became
natural. When Tina hung out at Susie's pool, I was there as well. If
Tina and Susie wanted to go see a movie, I went with them. When Susie
did Tina's makeup, I watched. If they wanted to go shopping for clothes,
I was tagging along too.
In truth, I didn't mind hanging out with them at all. Since the dawn of
time, young boys have developed crushes on the girl next door. I was no
different. I found Susie so enticing, so exotic that all I wanted to do
was spend time with her. Susie had long, dark hair that she styled a
different way almost every day. She was, of course, taller than me, and,
at almost 18, had fully reached womanhood. I know it was juvenile (but
then again, I WAS a juvenile), but her breasts seemed so big and so
voluptuous that my eyes often didn't reach Susie's head. I probably
stared too much when she sunbathed at her pool, hoping for a peek at her
nipples by some miracle. I'm sure I was a little too obvious in trying
to sit next to her at the movies. But I willingly did whatever I could
do to be close to her, whenever I could.
It was on one of Tina and Susie's many shopping trips that it happened.
Tina and Susie spent the day in the juniors department of our local
store. They tried on dresses, skirts, tank-tops, you name it. All the
while, I was following and watching Susie intently. When Susie held up
two dresses and asked me which dress I liked better, I enthusiastically
picked the sleeveless yellow sundress. It did look sexy. It had a
short, flared skirt and a halter-tie top. The belly was exposed, making
the dress look almost like a bikini top paired with a short skirt. I
knew Susie would look gorgeous in it, and it definitely would fuel my
young breast infatuation to boot! So I picked that one for her.
"Great!" she said. "Come with me as I try it on." With that, Susie
grabbed my hand and led me into the dressing room area. I hesitated, but
a slight tug was all it took to get me to follow. I had never been into
a girls dressing room before. I was nervous, afraid of getting caught.
But Susie wanted to lead me into her dressing stall, which meant that I
would get a chance to see her change. How could I pass up that chance?
Susie playfully pulled me into her stall and locked the door. She
unzipped the dress she was wearing and slid the strap down her arm,
pausing there to instruct me to turn around and not peek. I turned
around, but I would be lying if I said I didn't peek a little, trying to
catch a glympse through the mirror in the dressing stall. I could see
Susie slide her dress off her shoulders and let it fall gently to the
floor. I saw her caressing her breasts as she prepared to try on the
dress I selected. When she did this, I swear I saw her smile a little as
she looked in my direction.
As I expected, Susie looked great in the yellow halter dress. She
stepped out of the dressing room to show Tina when we both were
confronted by the manager of the juniors department. "He can't stay
here," she said to Susie, motioning toward me. I was preparing to leave
when Susie surprised me. "SHE is a girl," she said softly but firmly to
the manager. "I know she's a little tomboy-ish, but we're here to try to
get her to buy something more conventionally girlish. I was showing her
this dress to convince her to try one on herself."
The manager looked at me skeptically, but she responded, "Well, if your
sister wants to try something on, I'm sure we can accommodate her.
What's your name, sweetie?"
I froze a little, but Susie jumped in. "She's not my sister; she's my
friend, Tina's, little sister. And her name is Charity." I smiled and
agreed with Susie, not wanting to get into trouble both for being in the
girl's dressing room and for lying. "Could you find this same dress in
her size?" Susie asked. Although I don't believe the manager believed
Susie's story, she nevertheless complied - either to milk the sale or to
enjoy seeing a boy forced to try on a dress, I'm not sure which.
A moment later, the manager returned with the same dress as Susie's but
in a white. She handed me the dress and said, "Here you go, Miss
Charity, let me know if you need some help getting it on." I looked at
Susie and Tina (who had wandered over by this time), and they nodded for
me to go. Tina followed, saying that she would help her "sister" try it
on.
Inside the dressing stall, Tina gave me a quick lecture about sneaking
and lying. She said that I had to at least try it on, seeing as how I
had played along with Susie's deception. When I had the dress on, Tina
looked at me and remarked, "Wow, you really do look girlish in that
outfit!" Before she let me out, Tina fingered my hair a little and added
a barrette on one side. She quickly applied a little blush to give me a
more girlish look. Now, I had to face Susie and the skeptical manager.
I tentatively stepped out of the dressing room, to a "Ta-dah" from Tina.
Susie was overjoyed, dragging me to the mirror so I could see us as
"twins." "Ooo!" she exclaimed. "You look sexy!" Even the manager
seemed to hesitate. Perhaps I looked girlish enough to set her back on
her heels a little. I looked in the mirror, and was astounded. I
actually looked like a girl.
Although Susie suggested I try on some other clothes, I declined. I
wanted to change and get out of there as quickly as I could. Susie,
however, convinced me to keep the white dress on, and convinced Tina to
get another color in the same style. When the manager asked if we wanted
to wear our new dresses out, Susie enthusiastically agreed, but told the
manager that I need some sandals to go with my dress, as I had insisted
on wearing my boyish shoes out here. With that, three young women,
Susie, Tina and "Charity," exited the department store in matching
dresses.
The girls wanted to get some lunch, but I begged to go home instead.
They agreed, but only after extracting a promise that their new "little
sister" would let them dress her up more when we got home. That
afternoon, to the giggles and encouragement of Tina and Susie, Charity
got a full girl treatment, trying on a dozen outfits, getting made up and
having her hair styled. If I'm honest, I had fun playing Charity for the
afternoon as well. And, it would not be the last time I played Charity
that summer.
Chapter 3
I returned from the memory of my summer of femininity as I was finishing
Tina's nails. When we were done, Tina told me that she was going out for
a late dinner. "I'm meeting up with Susie, who is coming here after
work. She's planning to move back to South Carolina soon and wanted to
meet up." I looked at Tina with puzzlement. "Susie is coming back?
Susie who used to live next door?"
"I'm sorry, Charlie. Did I not mention that? Susie called me on
Tuesday. I was so excited, I guess I just forgot to tell you. Yes,
that's why I had my hair done, and that's why I was so happy you didn't
travel with Connie today, so you could do my nails like you always do.
Anyway, I'm sure Susie would love it if you joined us. Why don't you
change into something nice and come with me?" I reluctantly declined,
informing Tina that I'm supposed to talk to Connie at 8, and it would be
better if I weren't out (or with Tina, but I didn't say that).
With Tina gone, my mind was occupied processing the possibility of
Susie's return. I finished our wine and the cheese (that would be
dinner), dreaming of spending time with Susie again. Would the three of
us be close again? Now that we're adults rather than teens, it had to be
different, right? But would it be good? Would Susie finally see me as a
boyfriend, or would my time as her ersatz "little sister" forever mar her
image of me?
With these thoughts in my mind, my call with Connie was a disaster. She
argued with me, again questioning why I chose my sister over her, and
again making accusations that "whatever you do with Tina" on Friday is
unnatural and possibly incestuous. I hung up the phone feeling more
lonely than ever.
Sitting alone on a Friday night, and feeling buzzed from the wine, I
began to dream of Susie. Well, it wasn't a dream so much as a memory
filled fantasy.
After our experience in the juniors department, Tina and Susie dressed me
up every day for a few days. They were so excited to have a little
sister to play with. I tried on a whole stock of Susie's old clothes.
With most outfits, Susie recounted memories of which dates or family
events she wore them to, how sexy she felt in them and when she would
bring herself to pleasure in them. Fueled by an intimacy of sharing
Susie's clothes, I secretly had to sneak to the bathroom to pleasure
myself in order to keep from having an decidely non-girl bulge in my
outfit. This also was the time that Susie showed me how to paint nails,
and made me practice on myself, Tina and herself in order to get better.
On day three, Susie gave me a two-piece swimsuit to wear. She convinced
me to put it on (by briefly flashing her breasts for me), but I refused
to go outside in it. I stood, trembling in the doorway for a few
moments, watching the two of them in the pool. Unable to go outside, I
fled back into the house and up to the bedroom. I changed and retreated
to my own home.
The next day, I refused to be Charity for them. I was pouting in my room
when Susie came upstairs to see me. She was wearing a short denim skirt
with buttons in the front. On top, she had a soft knit crop top that
showed just a bit of her belly. Her nails were a shiny pink (that I had
polished for her) and she wore soft makeup and a shiny pink lip gloss.
She had a small black strapped purse over one shoulder.
"May I sit on your bed, Charlie?" she asked. I waved my hand and she
slowly sat down next to me, her purse falling from her shoulder. "Cute
toes, Char," she said, motioning to my shiny pink toenails. In my rush
yesterday, I didn't stop to remove the polish from my toes.
"I look like a sissy!" I said.
"Charlie, you're not a sissy." She said. "I mean, wasn't it awesome
when ratty old Miss Claire at the store saw you in that white dress?
Until then, she was sure you were a boy, and she was intent on
embarrassing you for sneaking into the girls changing room. But you came
out playing Charity and really fooled her! Twice, she quietly apologized
to me for her mistake, afraid we weren't going to buy anything. All
because of how brave you were, Charlie. That's not being a sissy."
"She deserved it."
"And wasn't the material just so soft and so freeing? I saw you smiling
when the breeze flowed up your legs in the parking lot that day." I
didn't say a thing.
"It's alright for you to enjoy the material, Charlie. Why does society
say that only girls wear those clothes? There's nothing like wearing a
skirt in the summer, am I right Charlie?" I nodded slightly, too
embarrassed to say out loud that I enjoyed wearing girl's clothes.
"It's OK, Charlie. It will always be our secret. Neither Tina nor I
would ever embarrass you. Besides, it took guts to do what you've done.
You're not like those stupid boys that try to hit on me all the time.
I'd take you over them any time."
I perked up at this comment. Then, Susie leaned over slowly and kissed
me. I could taste her kiss. She kissed me again, spreading more of her
pink lip gloss on my lips. She whispered, "Oh, Charlie," and moved my
hand to her breast. Susie took my face in both her hands and kissed me
vigorously. A moment later, she leaned back on the bed, pulling me on
top of her. She moaned "Don't stop," while I kissed her and caressed her
breasts. Susie reached inside her skirt with her hand. Shortly
afterward, she shrieked, "Oh, Charity!" as she orgasmed.
But, thankfully, Susie didn't leave me hanging. Instead, she flipped me
over, sat up on top of me and smiled. "Charlie, can I try something?"
she asked. "Anything!" I told her.
Susie reached to find her purse, which was somewhere between us on the
bed. Inside she took out her pink lip gloss and, instead of doing her
own lips, she brushed it on me. She slid off of me and said, "Kiss me,
Char" (pronouncing it like "chair" this time). "I want to taste you."
As I kissed her, Susie's hand reached down to my penis, stroking me
through my undies. She then pulled down my shorts and my underwear, and
slid me over to the edge of the bed. Susie moved to the floor and began
rubbing me with her hands. It was the first time a girl had ever touched
me, and I swear I would have cum if she continued two seconds longer. To
my surprise, Susie took me in her mouth instead, rubbing the inside of my
thighs with her hands. Right then and there, I had my first sexual
experience with a girl -- no, with a woman.
Sitting alone on a Friday night, the memory of this experience almost a
decade ago came rushing back to me. I found myself reaching down my
jeans and feeling my hard member pressing back. Wanting to feel the
whole experience again, I ran into my bedroom and stripped naked. Then,
I went into our bathroom, found a shiny lip gloss and put it on my lips.
"Oh, Charity, that's so sexy," my mind heard Susie saying. I pulled a
pink nail polish from Tina's collection, picking something that was a
close to the pink as I could remember. I rushed back to my own bed and,
for the first time since that summer so long ago, quickly applied a
single coat to my toes, touching myself while doing so.
I leaned back on my pillows, tasting my lip gloss and staring at my pink
toes. Fueled by alternating moans of "Oh, Charlie," and "Oh, Charity,"
in my head, I brought myself to climax, screaming "Yes, Susie, Yes!"
while I did.
A few minutes later, I was still leaning on my bed, my belly getting
sticky and wiggling my pink toes in the air. "Boy, you are in trouble,
Charlie," I told myself. In just the span of a few hours, everything has
changed. Your relationship with your girlfriend is falling apart, your
teen crush is coming back, your sister just outed you as a manicurist,
and, to top it off, Charity seems to be coming back into your life.
Jeez, Charlie, what's next?
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