Chapter Seven - Grace Does Dallas
"Good morning sweetie," Grace said. "Did you sleep well?"
"Yes. I did," I smiled. "Did you?"
"Yeah. I did. I guess you have to get going?"
I frowned. "Yeah. I do."
"I'm going to miss you this week."
So far, we had not seen each other even once during the work week. It
was like Grace reserved me for weekend play. I asked, "Why don't we get
together for dinner?"
"Oh baby. I'd love that," she replied. "But I've got to go out of town
this week. I won't be back until Friday night."
I was disappointed to hear that. She hadn't mentioned it all weekend.
"Really? Where do you have to go?"
"There's some stupid oil producer's meeting in Dallas that my boss is
the chairman for. I have to go help run the meetings."
"Oh," I said, even more disappointed now that I heard who she'd be with.
All I could think of was Grace being down there with her boss and those
other oilmen. For nearly a week. And I'd be here alone, wondering what
she was doing.
Seeing my disappointment, she said, "It's okay. I'll be back Friday
night late. Maybe you could come here and meet me?"
"Uh, okay," I said, glad that she was choosing to have me welcome her
home.
"Now you better hurry and get your shower. I'll fix coffee while you
get dressed."
When I came into her room from the shower, I found that Grace had laid
out my clothes I'd worn over on Friday. And next to them was a set of
sexy lingerie, which I assumed she expected me to wear under my clothes
that day. She walked in with two cups of coffee as I was surveying the
delicates on the bed.
Seeing me looking at what she'd laid out, she asked, "You don't mind -
do you? I like thinking of you in pretty things during the day when
we're apart."
"No. It's okay," I assured her.
"Do you mind if I watch you get dressed?"
Seriously? I don't know why, but it was one thing to wear the clothes.
It was something else altogether to get dressed with her watching me.
It was, somehow, more embarrassing to have her watch me go through the
ritual of donning the feminine attire. But I couldn't think of an
objection she wouldn't shoot down, so I said it was okay.
I picked up the red ruffled thong and slipped it up my legs, settling my
penis inside the tiny cup, nestling the thin strip of nylon into my
crack. I then secured the black net garter belt in place. The
stockings were black silk, with dark black polka dots, Cuban heels, and
a wide grey welt. I picked up each one in succession; carefully
gathering the soft fabric into a bunch as I slid my toe in, and then
gently pulled them up and fastened them to the six clips dangling from
the garter belt. I couldn't explain it, but there was something
intoxicatingly sexual about the act of putting on stockings that I'd
come to enjoy. Next came a pair of silver and black tap pants and a
matching camisole.
I'd noticed Grace intently watching me as I dressed for her. When I was
done, I turned to look in the mirror. I could see her watching me from
behind, sizing up my response to the sexy, feminine lingerie.
"You look very pretty Danni. Pretty and sexy. Don't you think?"
Unsure how to respond, thinking it almost sounded conceited to agree,
although I did feel that way, I said instead, "If you think so."
"Hmmm," she thoughtfully considered my reply. "I suppose that is true.
A woman usually has in mind pleasing someone other than herself when she
wears sexy underwear. But it's important to please herself as well.
You like it too - don't you?" she pressed.
Embarrassed and ashamed to admit it, I looked down and said shyly,
"Yes."
"It's okay. I'm glad you like feeling and looking pretty for me Danni.
Will you wear something everyday for me? So I can think of you like
that? So you can feel sexy under your boy clothes?"
I didn't want to seem too eager, but I did want to. I wanted to please
her. I liked wearing the lingerie for her. It made me think of her
when I wore it.
"Yes. I will," I answered.
"Thank you," she said as she moved behind me and held me gently in her
arms, stroking my penis through the nylon tap pants. "I suppose you
should get dressed. Besides, I have to get ready to go to the airport."
"Would you like me to drop you off?" I asked. "It's on my way home. I
can be a little late getting to work." I found that I didn't want to
leave her just yet.
"Really?" she asked animatedly. "That would be really nice! You could
help me pack and get dressed. Would you like that?"
"Su, sure," I said, suddenly concerned about what that might entail.
"Great! I'm just going to jump in the shower real quick. My suitcase
is on the floor in my closet. Get that out for me. Then you can maybe
choose my lingerie for the week and lay it out for me? Okay?"
"Su, sure," I replied as she disappeared into the bathroom.
I went to her closet and found her luggage. I carried it to her room
and opened it up on top of her bed. I then went to her lingerie drawer
and looked at her large selection of intimate wear. I struggled with
what to select. If it were for me that she'd be dressing, I'd want her
to wear the sexiest outfits possible. But it wasn't for me she'd be
dressing. Not that she'd be dressing for the conference attendees, but
they'd certainly benefit from her beauty. The thought of that made me
feel a pang of jealousy.
But I knew Grace by now. She'd want to look nice, and for her that
started with sexy lingerie. I began selecting sets of matching panties,
garters and bras. I then picked out several pairs of stockings for her
to wear. I added a few slips as well. I was looking in her closet for
outfits when I heard her come in from the bathroom.
Speaking to me from her room she exclaimed, "Oh Danni! What excellent
choices!" Giggling, she added, "If I didn't know better, I'd think you
were trying to get me fucked while I'm off with the boys."
I froze when she said that. No! That wasn't what I intended at all!
That was the last thing I wanted. I returned to the bedroom to let her
know that wasn't so. As I entered, she was putting on one of the sexy
sets already.
"Grace!" I said. "Are you going to wear that on the plane?"
"Of course! I wouldn't hurt your feelings by not wearing what you
selected."
"Bu, but I didn't mean for you to th, think wh, what...you said. About
you ge, getting, you know. I didn't mean that. I jus, just thought
you'd like to we, wear ni, nice things."
"It's okay sweetie. I'm flattered that you want me to be as pretty and
sexy under my clothes as you will be under yours. It'll be fun! That's
half the fun of wearing sexy lingerie. Us knowing what they can't see -
but would love to. We can each think of what the other is wearing while
we're apart. I don't care what those oilmen think. Shoot! I'm going
to be the only woman at the meeting. They'd probably want me no matter
what I wore."
Ouch! That didn't actually make me feel better. I hadn't really had
time to think of who all the people were going to be at the conference.
Now that Grace emphasized it, I pictured a bunch of tough, roughneck
cowboy type men. They'd all be lusting for Grace. Dressing her in sexy
clothes wasn't going to help matters. She could see the hesitation in
my eyes.
"Don't worry Danni," she said sweetly. "I love you. Don't fret over
what men might think of me, or who else might want me. That's not love.
Not like what we have. Come on," she said, taking my hand and leading
me to her closet. "Help me pick out some dresses."
Reluctantly, I followed. Suddenly, I wasn't in the mood to pick out her
dresses for her. If it were left to me, I'd pick out the least sexy
ones in the closet. Instead, she began picking out the dresses. Each
one she'd pick, she would ask, "Do you like this one? Would I look good
in this one?"
The answer was always yes. There wasn't anything in her closet that she
wouldn't look good wearing. The problem was that she'd picked out the
shortest and sexiest dresses in her wardrobe. The outfits she chose
would all highlight the sexy lingerie I'd picked out. I felt like I was
an accomplice to her seduction of the oilmen.
Next she picked out a few sexy nighties and held them out. "What do you
think?"
I felt sick to my stomach. Why did she need such sexy sleepwear?
"Uh, uh," I stuttered. "Do you really need those?" I asked, referring
to the sexy nighties.
"Oh!" she replied, raising her eyebrows. "You'd rather I sleep nude?
Is that how you want to think of me Danni? Naked, easily accessible?"
she teased, clearly relishing seeing me so uncomfortable.
"No!" I protested. "That's no, not wh, what I meant?"
Grace was smiling at me as I stumbled over my words. "Then these?" she
asked holding up the sexy nighties.
"I gu, guess," I said.
"You're funny Danni," she giggled. "You don't want me to look sexy for
anyone but you?"
Huh? No! Of course not! What was she saying? Was she going to? Look
sexy? For someone else?
Seeing my confusion and discomfort, she reassured me. "All I'm saying
Danni is that I like wearing my sexy nighties. I like how I look in my
sexy clothes. Why do you think I've bought so many? Just so I can
excite men to get them to fuck me? Believe me, men would do that no
matter what I wore. Or didn't wear," she added, laughing hysterically
at the thought.
Once again, her reassurance was anything but. Nonetheless, I could see
I was fighting a losing battle. Plus, we needed to get going so she
could check in at the airport and I could get to work.
Grace went to her closet to pick out something to wear on the plane and
I began packing the clothes we'd chosen for her trip. I hadn't noticed
it earlier, but she'd laid out a very skimpy bikini with a matching,
see-through cover up. I almost said something, but realized it would be
a waste of time to challenge her. I fought against imagining her lying
by the side of the hotel pool wearing that skimpy piece of fabric
though. All I could see were other men drooling over her. I folded the
tiny suit and placed it in her suitcase. Once everything was packed, I
zipped it and set it on the floor.
Grace exited her closet wearing a short, red leather mini-skirt and a
tight white top. Her bra was visible through the top and it was obvious
she was wearing stockings under the mini. In fact, it was the same red
leather mini-skirt I'd worn for her the previous Friday night - the one
she'd said made me look slutty. So, Grace intended to fly to Dallas
looking like a slut, according to her own description of the outfit.
I must have given away my reaction by the look on my face. She asked,
"What? Don't you like my outfit?"
"Er, ah, it's just that, well, you said, that skirt, ah, looked sl, slu,
er, that you thought I looked, you know, the other night." I couldn't
say the word. I was afraid to say the word. It was one thing for her
to call me a slut. I dared not call her one.
Grace examined me appraisingly. "I don't understand Danni. I thought
you liked this outfit. You wore it for me the other night. Now I'm
wearing it for you. Hmmm?"
I didn't know how to respond. "But, you, you're going to Dallas. I
won't see you wearing it."
"Truuue," she said. "But you can think of me wearing it for you.
Wouldn't you like that?"
I could not give a right answer to her question. If I said yes, then I
was giving her my consent to look like a slut. If I said no, then I
insult her choice of skirt. And so I said, "You look amazing in that
skirt. Compared to you, I didn't come close to doing it justice."
"Why thank you Danni," she cooed. "But don't sell yourself short. If
we'd gone out the other night with you dressed like this, I have no
doubt you'd have had men everywhere wanting to fuck you."
There! She did it again! She complimented me. I think. But what I
heard her say was that men everywhere are going to want to fuck her when
they see her wearing this skirt. I was beaten. And all day I'd be
tormented thinking of her walking through airports dressed like a slut.
I hadn't put my shoes on yet and sat down to do so. The heels she was
wearing were probably four inches, which, of course, caused her to tower
over me. Grace cleared her throat as I reached for my socks.
"What?" I asked.
"It's nothing," she said. "Actually, it's, it just doesn't seem right
to cover those pretty stockings with socks. Would you mind not wearing
socks?"
"Bu, but Grace," I implored. "Someone might see," I whined.
"Oh I don't think so. Won't your trousers hide them? No one looks at a
man's ankles anyway. Please?" she begged.
I sat there holding the sock in my hand. Damn it! I didn't feel good
about this, but I couldn't tell her 'no' either. Relenting, I put the
sock back on her bed.
Smiling after so easily getting her way, Grace came to me and hugged me,
kissing me on the mouth. A healthy smidge of her lipstick transferred
to my lips and when I raised my hand to wipe it off she shook her head.
"Leave it. You can barely tell."
I bent down to pick up her bag. "Ready?" I asked.
"Yes kind sir," she giggled as she took my other arm.
We laughed as I played her chauffeur on the way to the airport. I
dropped her off and we kissed goodbye.
"Call me when you get there?" I said.
"If I can baby," she said noncommittally. She raised her hand, kissed
it, and blew me a kiss. I returned the gesture, not considering how
girly the act appeared.
I then drove home and went inside to put on a suit for work. I paused
to look at my reflection in the mirror. It was off-putting to see
myself dressed in such feminine clothing. It also was arousing and
exciting knowing that I'd be dressed that way all day and no one would
know except Grace and me.
The biggest drawback to wearing sexy lingerie all day was that I
couldn't go more than five minutes without thinking of Grace. Even
remembering some of the things she did to me excited me. I found myself
reliving sucking her dildo and urging her to use it on me more
vigorously. And then there was the matter of her fucking me with it. I
felt so weak because of letting her do that to me. Worse, though, was
reliving how good it felt once she penetrated me and began really
fucking me hard. Hell! I couldn't believe I came without even touching
myself. I was dripping throughout the day due to my continual increase
and decrease in arousal.
In the middle of the afternoon I received a text message from Grace. It
read simply. "I've landed safely in Dallas baby! Hugs! G."
Happy to finally hear from her I quickly replied, "Glad you're there
safely. Hope you had a good flight. Hugs back!"
I waited for a reply, but none came. I was disappointed. I was hopeful
that we'd text chat for a while. Nearly constantly concerned about
acting overanxious or clingy, I didn't attempt to text her again.
Instead, my day continued on to conclusion. My best effort to
concentrate on work related matters was a drain, as all I could really
think about was the lingerie I wore for Grace which, of course, led me
to think of her and what she'd be doing in Dallas for the rest of the
week with her boss and his oilmen colleagues.
When I arrived home I shed my suit, but not the lingerie. Instead, I
slipped on the six-inch spike heels that Grace has sent me a few weeks
ago and went about my evening activities dressed like that. I thought
about why I stayed dressed as I was when there was no one around to
insist upon it. I convinced myself that I did so because I knew that
was what Grace would want.
When it got to be near ten o'clock, I decided it was time for bed. I
took off the lingerie I'd been wearing all day and took a shower. I
then went to the drawer where I was keeping the nighties Grace had sent
me and picked out the light blue baby-doll and cover with matching sleep
panties.
Wishing Grace would call or something, I snuggled under the covers and
began reading a book. Before long I began to doze and drifted off to
sleep. I thought I must be dreaming when I first heard it. Then I
realized that my cell phone was ringing. I had no idea what time it
was, but I immediately thought it must be Grace calling. I scrambled to
get to the phone before it stopped ringing.
"Hello!" I spoke anxiously into the phone, barely awake, not focused
enough to see the time.
"Danni? Are you awake honey?"
"I, I think I fell asleep. Grace? What time is it?" I asked.
"It's nearly two baby. Oh! Did I wake you?"
"Two?" I repeated. By now I was able to focus upon the clock on my
night stand. It said five till three. "It's almost three Grace!" I
corrected her.
"Ooops!" she giggled. "I forgot about the time difference. It's only
two here. I just wanted to call and say goodnight."
My mind was still fuzzy, but I could figure out that Grace was up late,
no matter which time zone she was in.
"You're just going to bed?"
"Well, not exactly. But I am just going to sleep, and I wanted to say
goodnight. I'm sorry if I called too late. Would you rather I not call
baby?"
"No! No!" I quickly answered. "I'm glad you called. What have you
been doing?"
"We went out to dinner, had a few drinks, and then came back to the
hotel."
"We?"
"Yeah. My boss and I."
"Oh. How has the conference been?"
"The conference doesn't start until tomorrow. How about you? How was
your day?" she asked, as if she was attempting to change the subject.
"It was okay," I answered. "I miss you though."
"That's sweet Danni. I miss you too. Hey! What are you wearing?"
"Uh, uh, I'm wearing the light blue baby-doll you gave me."
"Ooooh! That's sexy! I wish I could see you. I'm glad you're wearing
it."
"Wh, what are you wearing?" I asked, getting in to her phone sex play.
"Me?" she teased. "Do you really want to know?"
"Yes," I replied.
"I'm not wearing anything."
"Nothing!?" I asked, surprised.
"Nude."
"Oh. I didn't think you slept in the nude."
She giggled. "Well I don't usually. But I haven't been sleeping yet.
Why? Would you like to think of me in a nighty? One of the one's I
brought?"
"I, I don't know. I just was wondering." What I was really wondering
was why she was naked, hadn't gone to sleep yet, and was calling me so
late. But I couldn't say that.
"Danni?"
"Yes?"
"Guess what I'm doing?"
"Right now?"
"Yes."
"I, I don't know," I answered, unsure where she was going with this.
"I'm touching myself."
My penis throbbed to attention. "You are?"
"Yes," she said seductively. "How about you?"
"Me?"
"Yes baby. You. Are you?"
"Am I wh, what?"
"You know. Say it."
"Touching myself?"
"Um hmm," she moaned.
"No," I told her.
"Will you?"
"Uh, okay," I agreed. I slid my hand between my legs and stroked my
growing penis outside of the panties I wore.
"Are you rubbing outside of your panties?"
"Ye, yes."
"I love that you are wearing them while I'm gone. You must like it."
I didn't respond, afraid to admit it to her.
Pressing the issue she continued, "Do you Danni?"
Avoiding the issue, I answered, "Do I what?"
"Danni! Don't be coy! You know what I mean. Say it."
"Ye, yes. I do."
"Why?"
"Why?" I repeated her question.
"Why do you like wearing panties?"
I hesitated. She made me so uncomfortable when she pushed me like this.
"I, it makes me th, think of y, you."
"Ummm! I like that. What else?"
"Else?"
"Don't tease me Danni. Why else do you like wearing them?"
"Th, they feel go, good," I blurted.
"Yes. They do. Don't they? Girls love wearing panties."
I didn't know what to say. I felt I should say something. "I, I'm, n,
not a gi, girl."
"No. You're not. Hmmm. But you like wearing panties and pretty girl
things. Hmmm."
What did she mean by that? I'm not the other thing either. I'm not a
si, si, sissy either.
"Are you hard Danni? Is your penis hard?"
"Ye, yes," I stuttered.
"Rub it harder Danni," she commanded. "I want you to cum with me."
I rubbed my penis outside of the panties. I was getting close.
"Are you rubbing yourself Danni?"
"Yes!" I moaned.
"Me too. You wouldn't believe how wet my pussy is Danni. I wish you
were here to lick it out."
"Li, lick it out?" I groaned.
"Yeah! You know how much I like it when you do that."
What was she saying? 'Lick it out?' Did she mean 'Lick it?'
"Do you wish you were licking me clean Danni?" she continued.
She did it again. 'Lick her clean.'
"Danni?"
"Yes! Yes! I wish I was licking you now!" I moaned as I reached my
peak. I began cumming in my panties, soaking the nylon with a huge
burst of semen.
"Danni? Did you just cum baby? In your panties?"
"Ye, yes," I admitted.
"Oh God! That's so hot! You came thinking of licking my pussy clean!
Taste yourself Danni," she ordered.
"Wh, what?" I asked, hoping she didn't mean what I thought she meant.
"Taste your cream Danni," she repeated. "Put your hand in your panties
and taste yourself."
I knew she wasn't going to give up until I did it. I slipped my hand
inside the front of my soaking wet panties and squeezed my penis, a
large glob of sperm filling my palm. Withdrawing my hand I stuck my
tongue out and licked the thick cream out of my hand. I was becoming
more used to the taste.
"Are you doing it Danni?" Grace interrupted my thoughts.
"Yes," I answered. "I did it."
"Oh Danni! Thank you! That is so erotic baby. Don't you love it?"
"I, I gu, guess so," I reluctantly acknowledged.
"I understand," she assuaged me. "You would rather lick sperm out of my
pussy. Right?"
"M, my sperm," I added.
"Of course," she agreed. Sighing, she went on, "That was fun! Did you
like that sweetie? Our first phone sex!" she laughed.
I laughed with her. "Yeah! It was fun."
"Oh yeah! I almost forgot to mention something Danni. Mandy is having
a party Saturday night."
"She is?"
"Yes. Would you like to be my date?" she asked.
"Sure!" I readily agreed.
"Super!" Grace replied. "Well, I guess I should get some sleep. It's
been a long night and tomorrow will be a busy day. Night night baby,"
she whispered sexily.
"Goodnight," I answered.
"Danni?" she asked.
"Yes?"
"Don't forget honey."
"Forget? Forget what?"
"Tomorrow. Under your suit. Wear something pretty? For me?"
"O, okay," I agreed.
"Thank you. And one more thing. Don't forget to wash the panties you
soiled tonight."
'Soiled?' "Okay," I answered.
"Bye baby," she said and clicked off the line.
Normally, after sex, I'm ready to fall asleep. But I was wide awake
now. The things she'd said about me cleaning her out. About her
needing to be cleaned out tonight. Did she? Would she? She said she
loved me. Why would she - with her boss - if she loved me? She
wouldn't. She was teasing me. It was just phone sex. A fantasy. That
was all. Still, I couldn't sleep.
I lay in bed thinking about Grace. Worrying about her being in Dallas
all week with all of those macho oilmen. They'd all be lusting for her
the whole time. And she'd be teasing them - keeping them all keyed up -
by wearing sexy outfits and skimpy lingerie. Lingerie I'd chosen for
her. But she loved me. I was her boyfriend. She wanted me to go to
Mandy's party with her.
My mind went on like that for the rest of the morning. Finally, I
decided to get up and get ready for work. I removed my nighty and put
it in the hamper. I then hand washed the sleep panties I'd cum in only
hours ago and hung them over a rail next to the sink to dry.
In the shower, I noticed my legs were a little bristly. This was the
biggest drawback to shaving. You had to keep doing it, or suffer the
stubble. I lathered my legs and underarms and went to work. My strokes
were becoming second nature, navigating the varying curves of my legs.
Once showered and shaved, I dressed, first donning a garter belt,
stockings, a camisole and matching panties. I then covered the pretty
lingerie with my male clothes and headed off to work. I was becoming
more accustomed to the fact that I was wearing women's underwear beneath
my clothes. I had a lot of work to do and, as a consequence, didn't
think much about what I was wearing,or Grace, all day. Before I knew it
I'd accomplished everything I needed to get done and was heading for
home.
As soon as I walked in the door I headed for the shower to refresh
myself. I decided to get ready for bed. I was exhausted from being up
this morning so early. I wore the yellow nighty with matching tap pants
and the sheer cover. I then poured a glass of wine and fixed something
to eat. I curled up on the couch and ate while watching the news.
I hadn't heard anything from Grace all day. I was really tired and
wanted to go to bed. I decided to try and call her. Her cell phone
went immediately to voice mail. I left her a message saying I was going
to bed, but that she could call if she wanted.
Although I was tired I couldn't stop thinking of Grace, wondering where
she was and who she was with. It wasn't exactly that I didn't trust
her. I believed she loved me and didn't think she'd cheat. But then
again, we were still new, and it wasn't like we'd agreed that we'd be
exclusive. Could I really expect that nothing would happen? After all,
she was at a conference with a bunch of oilmen. And she was beautiful
and extremely desirable.
I kept looking at the clock. It read 1 a.m. I'd been in bed three
hours without being able to sleep. It was stupid, but I decided to call
her again. I'd say I was just calling to say goodnight. It was only
midnight in Dallas. Her cell phone went to voice mail right away again.
I decided not to leave another message. Instead, I searched for the
phone number of the hotel where she was staying and called. I asked the
desk clerk to connect me to her room. Maybe her cell phone was on
silent and she didn't hear it. Her hotel room phone rang and rang. No
answer. When the opportunity to leave a message came, I just said that
I was calling to say good night, and that I loved her, and to call me
when she got in.
I was restless. Now I worried even more. Where was she?! I knew it
was only midnight there, but I wished she wouldn't stay out so late. So
what did I do? Leave it be? No. I obsessed. I called her every hour
until five o'clock EST - 4:00 a.m. in Dallas. Grace wasn't in her
room. Or, if she was, she wasn't alone and couldn't answer the phone
because of whoever she was with.
At some point I finally fell asleep. When I woke up I realized that it
was ten a.m. Damn! I never slept that late! Thankfully, I had no
appointments in the office, so it wouldn't be a big deal. I took a
shower and, without even thinking about it, selected a set of lingerie
to wear to work under my suit. I was filling my pockets when I noticed
a text message on my Blackberry. "Good morning baby! Sorry I missed
your call last night. I'll talk to you later. Love you. G." The text
was sent at nine a.m. EST. Was she just getting my message?
I texted her back. "Love you too. Have a good day."
I was disturbed that I hadn't been able to reach her last night. Or
this morning. But I knew I couldn't really challenge her. After all,
she was a grown woman. I had no right to tell her what she could do. I
tried to not think about it. Of course, that's all I did.
I spent another day without hearing from Grace. That night, after I'd
gotten home, and changed into my nighty, she called about nine.
"Hi baby!" she greeted me cheerfully. "How's it going?" She acted as
if the fact that I couldn't reach her the night before was no big deal.
"Hi!" I replied a bit curtly. "Good. How about you?"
"Tired!" she said, her voice sounding exasperated. "These guys are
running me ragged. But tonight is the last night for the gang.
Tomorrow I can relax some."
This was news. I thought the conference ran through tomorrow. But she
was staying until Friday? So she could take a day off in Dallas?
"Oh?" I asked. "Whatcha gonna do?"
"I figured I might just relax by the pool. Try to get a little tan."
She was going to spend the day by the pool wearing that tiny little
bikini.
As if she could read my mind she teased, "Bet you wish you could see me
in my bikini!"
"Uh, yeah," I said, but was really thinking about other men ogling her.
"I tried to call you last night."
"I know. I got your message. I just couldn't call back right away.
Sorry. I hope you weren't worried about me."
Worried? "Uh, actually, I was a little. You weren't in your room."
"What?!" she sounded surprised. "Why do you say that? Of course I was
in my room! When did you call?"
Was she lying to me deliberately? "I called a few times," I said,
minimizing the actual number of times I tried to reach her. "There was
no answer."
"Hmmm. That's strange," she said thoughtfully. "I'll have to check the
hotel. Maybe my ringer doesn't work. Are you sure you called the right
room?"
"I think so. I asked the desk clerk to connect me to your room."
"Well, that is sure strange," she mused, not actually saying I was
absolutely wrong. "Anyway, I'm sorry I missed your call. Hey! I have
a favor to ask you," she said.
That was a clever change of subject. "Okay. What is it?"
"Do you think you could take Friday off?"
What?! Was she going to come home early and we'd spend the day
together? That would be fun. "I think so. Why?" I asked, hoping I was
right.
"Well, this is kind of a big favor. But it would mean a lot to me if
you would do it," she said and left it hanging a moment.
"Okaaayyyyy," I said, coaxing her on.
"Actually, it's a favor for Mandy. But if you'd do it, you'd really be
doing it for me."
"Okay. Go on," I said, getting impatient, realizing already my initial
hope wasn't going to come true.
"Mandy called me a while ago, and is in a bit of a panic because she's
got a lot to do to get ready for her party..."
Anticipating where she was going, I finished her sentence for her. "And
she wants me to come help her?"
Grace seemed to hesitate. "Actually, she asked if I'd let her borrow
Sissy."
I was struck dumb. Did I just hear what she'd said? Of course I did!
"Are you kidding Grace?!" I questioned her. "You didn't say you would?
You're not really asking me to do that? Are you?"
"You said you would do me a favor Danni," Grace replied with an annoyed
tone. "If you didn't mean it, I wish you wouldn't have said it."
"Grace!" I exclaimed. "I would do anything for you! I think you know
that by now. But does she expect me to come to her house and dress up
as a maid?"
"Danni," she said, as if she were talking to a child. "She asked if I
could loan her Sissy, my maid. She didn't ask me to loan her my
boyfriend. She doesn't know they're the same person. She has no idea
you are Sissy. And there is no reason for her to find out."
Feeling trapped, I fought back. "But I've never dressed like that
outside of your apartment. How am I going to get to her house dressed?
Besides, my outfits are at your house."
Reeling me in, she countered, "No problem. I'll phone Walter at the
front door and tell him to let you in. You could even go there Thursday
evening after work and spend the night, then leave directly from there,
already dressed, to go to Mandy's house."
I wondered if it was my imagination, or had Grace already figured out
exactly how this conversation was going to proceed before we'd even had
it.
"D, don't you th, think people would notice if I walk out of your
apartment building dressed as a French maid? People don't do that
everyday," I added, sarcasm in my voice. I hoped this latest reasoning
would show her how silly it was to think we could pull off what she was
suggesting.
"Actually, I have thought of that. I think it would be best if you
packed your maid's uniform and changed after you get to Mandy's place."
Even more confused now, I asked, "You mean change into Sissy at her
house? Wouldn't that reveal to her who I am?"
"Danni! Don't be so dense. Of course not! You will have to put on
makeup and your wig at my place. Just don't dress up in the maid's
outfit right away. Borrow a pair of my jeans and a blouse to wear.
Then you'll look just like any other woman," she explained, as if it was
the simplest and most logical thing in the world.
I wasn't convinced. "What about Walter? He'll realize who I am won't
he?"
Without missing a beat, she said, "Walter is off Friday mornings.
Someone else will be at the desk, and they won't ever have seen you
before. They'll never put two and two together. You'll just be another
beautiful woman to him."
I felt trapped. There was nowhere else for me to turn. So I did what I
had done throughout my brief, but crazy, relationship with Grace. I
caved.
"Okay," I said unhappily. "But please don't do this again. I really
don't feel good about this. What if Mandy tries to come on to me?" I
asked, immediately recalling how much she seemed to have enjoyed my
talents the previous weekend.
"Danni! You naughty girl! Such thoughts!" mocked Grace. "You better
not do anything inappropriate with another woman! Especially without me
being there to watch!" she laughed.
I hated when she teased me like that. But instead of complaining, I
simply replied, "Okay. But what about her?"
"Let me handle Mandy sweetie. I'll talk to her. Okay?" she implored,
as if that would fix it.
"I guess," I finally capitulated.
"Thank you baby," she cooed, happy again to be getting her way. "Look,
I have to run now. I have to get ready for dinner. Want me to call you
later? Before I go to bed?"
"Uh, sure, if you want. Will you be late?"
"I don't know baby. I have to spend the evening with my boss and a few
of his closest colleagues. I can't very well blow them off, or rush off
to bed too early. But if it isn't too late, I'll call before I go to
bed."
"Okay."
"Bye bye baby. Love you!"
"Love you too," I said.
After I hung up, it began to really settle on me what I'd gotten myself
into. I'd agreed to spend an entire day with one of Grace's best
friends, dressed in drag, hoping against hope that she would not figure
out who I was. On top of that, I was actually going to venture out into
public - alone no less - dressed as a woman. I knew on every level that
it was crazy, stupid, idiotic, and that I should not even attempt it.
But I could not resist the pull that Grace seemed to have on me. And if
I were really honest with myself, I was excited about it. The twitch in
my panties told me the truth about that.
That night I went about my routine, or at least what was becoming my
routine. I changed out of my work clothes, showered and then dressed
back up in lingerie and a nightgown for the evening. I couldn't deny
that I loved the way the soft nylon felt against my body. And I also
could not deny that I liked the way I looked wearing the sexy feminine
garments.
I went to bed around ten, hoping that I would hear from Grace. But she
never called. I must have been suffering from sleep deprivation from
the previous evenings of sleepless nights, because I eventually fell
asleep and slept through the night.
I notified my managing partner at work the next day that I would not be
in the office on Friday. When he asked what I was going to do, I simply
told him that I was helping a friend get ready for a party she was
throwing that weekend.
On Thursday after work, I took the Metro home, changed out of my suit
and into some casual clothes, packed up some toiletry items and some
clothes for the weekend, and drove over to Grace's. When I entered the
building, Walter, the doorman, greeted me warmly at the front door.
"Good evening Danni," he said. "Ms. Andrews told me to expect you. I
understand that you will be staying overnight at her apartment?"
It continued to strike me a little strangely that he always called me
'Danni,' but Grace, 'Ms. Andrews.' It seemed to minimize my stature as
a guest of hers. But I never challenged him. It just seemed as though
he thought of me that way.
"Hi Walter," I greeted him back. "Yes, I am."
"Okay," he said. "I'll let you in. She told me to be sure to tell you
that if you needed anything to be sure to call me."
"That's very nice Walter. I'll do that. Although I'm sure I'll be
alright."
He walked me to the elevator and rode up with me. When the doors
opened, I exited, and he left me there, saying goodnight as the doors
closed. I looked around. It suddenly hit me that, although I'd spent
quite a bit of time alone in Grace's apartment, it had always been under
an expectation that she would be returning soon. I was alone in her
luxurious penthouse with no expectation that she, or anyone, would be
coming home.
I went into the guest room to survey the maid's uniforms and to make
sure that everything I would need the next day was clean and ready to
go. I'd brought a suitcase to pack everything in. Once I'd
accomplished that, I decided to take a bath and get comfortable. I
opened a bottle of wine and poured myself a glass before going to
Grace's bathroom and running some hot water. There was some bath soap
next to the tub. I sprinkled some into the water. It smelled fresh and
fragrant.
The warm water was very relaxing. I lay there for a while sipping my
wine and enjoying the luxuriousness of Grace's deep, soaking tub. I
could have stayed there for a while, but was getting hungry. I shaved
my legs and underarms before getting out, and then, after washing, I
stepped out of the tub and into the shower to rinse off with clean
water.
I toweled off and then decided that I would do a little practice dress
up for the morning. After all, I had Grace's entire wardrobe at my
disposal, and no one was going to be coming in to see what I was doing.
I found some body lotion and rubbed several generous handfuls into my
body. The lotion was lilac scented and it made my skin feel extremely
soft and smooth.
I then went into Grace's bedroom and began looking through her closet.
She had so many pretty dresses to choose from. I don't know what moved
me to do it, but I decided to dress up in one of her formal gowns. I
chose a beautiful flowing red chiffon gown with pearl appliqu?s sewn on.
Once I'd decided what to wear, I found a pair of heels to match, and
then went to her bedroom to select some lingerie to wear beneath the
dress. Grace had a red panty, bra and garter set that was perfect. I
found a pair of black stockings to attach to the garters. I carefully
pulled the stockings up my legs and then went to the dressing table to
apply makeup.
I had put my own makeup on before, but I really wanted to get it right
this time so I'd be sure I could do it tomorrow before going out in
public. I worked on my brow a bit at first, plucking a few stray hairs.
Then, I slowly applied dark eyeliner and a subtle gray shade above my
eyes. I was amazed how mascara could make my eyelashes look so thick,
long, and full. I added just a little bit of blush to liven my cheeks
and then checked out the final product. Once again, as on previous
occasions after seeing my face made up, it struck me how odd I looked
before the wig was attached. I looked like not quite woman, and not
quite man, but not exactly gay either. More like a sissy was what I
finally had to admit. I decided then that I preferred looking like a
woman than a sissy.
Next, I put on the gown. It felt light and billowy as it fell over my
shoulders. The bosom pressed out due to the large breast forms I wore.
I slipped the heels on my feet and then went to the closet for a wig. I
chose a long auburn wig made of human hair. It was such a nice wig that
you really couldn't tell it was a wig. Then I went to put on finger
nail polish. I selected a hot red nail polish that would go with the
gown, but would also look good the next day with my maid uniform on.
Once I was finished, I admired myself in Grace's mirror. I was truly
beautiful. I couldn't tell I was a guy, and I wasn't into self-
deception. I knew that I looked good, and was confident that I could
fool most people, especially people who did not know me.
I was so satisfied with how I looked that I wished Grace could see me.
I was certain that she would be pleased, although I was a little
concerned that she might not like that I had taken the liberty to help
myself to her wardrobe.
I poured myself another glass of wine, found some cheese in the frig and
crackers in the cabinet, then went out to the balcony to relax. I felt
so free and relaxed dressed up like a woman under the circumstances of
the evening - so much so that I wasn't even thinking about or fretting
over the next day.
After nearly finishing the bottle of wine, I decided it was time for
bed. Returning to Grace's bedroom, I carefully removed and hung her
gown in her closet. I then perused her large selection of sleeping
gowns. In keeping with the evening gown I'd worn all night, I selected
a long and flowing pink nylon gown that was edged with black lace and
had white pearl appliqu?s across the chest. There was a matching, but
more sheer, peignoir that I also wore. When I saw my image in her full-
length mirror I was amazed at how beautiful, sexy and feminine that I
looked. Any man who did not know better would have been turned on.
I was wondering if Grace was going to call when the phone rang. It was
only eleven o'clock my time, which meant it was only ten in Dallas.
"Hello," I said.
"Hi Danni," she cooed. "How are you sweetie?"
"I'm fine. How are you?"
"Ugh! I'm tired. You have no idea how exhausting it can be to lay by a
pool all day in the hot sun."
I laughed. I would have thought any woman would love to have that
problem. Instead of saying that, however, I teased her, "Poor baby."
Coming right back, she said, "Plus I had all those guys to fight off."
Now she was hitting below the belt. "Really?"
She giggled. "What do you think? You packed the bikini I wore. I'm
surprised you didn't try to stop me from taking it."
"Uh, yeah. I did. Bu, but you're ki, kidding - right?"
"Am I? What if I'm not?"
"Wh, what do you me, mean? What if you aren't?"
"What I mean is, what if there were guys coming on to me all day? Would
you like that? What if I was going to meet one of them for dinner?"
My penis twitched. "I wi, wish you wouldn't tease like that Grace."
"Who says I'm teasing? What are you wearing Danni?" she inquired
abruptly.
"We, wearing?" I choked.
"Yes. You're ready for bed I hope. It's late there. What are you
wearing to bed? Did you bring the jammies I bought for you?"
"N, no. I left them at my house."
"Oh! Are you naked then? Naked in my bed all alone?"
I couldn't lie to her. "N, no. I'm n, not na, naked."
"Then tell me what you're wearing."
"I'm wearing your pink and black gown and the matching peignoir."
"Oh God! How sexy! I love that you're wearing my clothes. If you soil
them be sure to wash them. Okay?"
"Soil them?" I asked. "How?"
"I don't know," she replied teasingly. "Are you thinking of me? Maybe
if we had a little phone sex?" she giggled.
Oh! I got it. "Ha ha," I said sarcastically.
"Are you all packed and ready for tomorrow?"
"Yes," I said. "Everything is in a bag, although I haven't decided what
to wear out of here. Any suggestions?"
"Why don't you borrow a pair of my jeans and a plain white blouse? You
won't attract much attention in that."
"That's a good idea. Do you think they'll fit me?"
"They might be a little tight. They're cut differently than male jeans,
but they're also supposed to be tight. Just wriggle your way into them.
You'll be fine."
"Okay. So are you going to bed also?" I asked.
"Hmmm. I don't know. It's early here. I might change and go down to
the bar for a drink."
I didn't like the idea of her going out alone, but knew that I couldn't
say anything. Instead I just gave a non-committal grunt, and said that
I couldn't wait to see her tomorrow. I asked if she needed a lift home
from the airport and she said she could get a ride home. "Just be ready
for me," she teased. "Wear something sexy!"
"Okay," I answered. "Goodnight."
"Goodnight angel. I'll be thinking of you lying there in my bed wearing
my sexy nighty. Smooch!" she said and hung up.
I tried to resist the thought, but couldn't fight back the image of
Grace meeting some guy at the bar who'd been lusting after her when she
was by the pool earlier in the day. I knew that if she went to the bar
alone, she was practically inviting guys to come on to her. The worst
part about it was that I thought that was precisely what she wanted me
to do. Worry. And, perhaps, needlessly. So, if that was the case, why
was I getting so hard lying there thinking about it? I stroked myself
through the soft nylon gown, my penis growing stiff as I did so. I
couldn't shake the image of Grace flirting with a big, strong guy,
inviting him to her room to play. The image that filled my brain was
one so opposite of what sex was like between Grace and me. Her man had
her bent over the edge of the bed, driving a huge cock into her pussy,
Grace begging and mewing like a horny woman who was being satisfied by a
man - the way a man ought to satisfy a woman - with his cock - not his
mouth. As the man fucking Grace in my mind pile-drove her, I began
stroking my own penis faster until, just as Grace orgasmed in my
fantasy, and her man began pumping her full of cum, I let loose with my
own wet stream, soiling Grace's beautiful gown in the process, as she'd
implied earlier. Ashamed of what I let my mind think, and even more so
with my reaction to the image, I fell asleep, Grace's beautiful gown
saturated with sperm.
I woke up early the next morning to get ready to help Mandy prepare for
her party. I also had to hand wash Grace's nightgown so that I could
hang it to dry before I left. The first thing I did was to take a hot
shower, quickly shaving my legs and underarms. I then toweled off and
rubbed some body lotion all over, covering my body with the sweet lilac
scent.
I put on a pair of plain white bikini panties and a matching white bra.
After slipping in my breast forms, I then entered Grace's closet and
searched for a pair of jeans to wear. Grace had several pair of
designer jeans, all neatly hanging in a row. I picked out a pair of
Calvin Kleins and tried them on. They were very tight going on and,
although they snapped comfortably around my waist, they felt nothing
like my own jeans and so I decided to try another pair. My penis was
outlined at the front in a way that I feared would be quite noticeable.
After trying on several more pair I realized that they all had the same
problem. Women's jeans were, quite simply, cut differently than men's
due to the very difference in anatomy that was causing me problems.
I couldn't go out in public with my bulge showing like it was. I
unfastened the jeans and tried pressing my penis backward, under and
between my thighs, so that it would not show in the front of the jeans.
It wasn't easy to do, but I finally got it pushed back pretty far, and
then held it in place by keeping my thighs held closely together. I
shimmied the tight jeans up to my waist and pulled them firmly onto my
crotch. The tight jean material held my penis in place. Once I
fastened them at the front, everything was just so. There was no bulge
whatsoever. Rather, my crotch looked just like any other woman's,
although the tight squeezing of my penis up into my ass crack was a
constant reminder to me that I was not 'any other woman,' but a man
wearing feminine clothing.
I picked out a loose-fitting, white blouse that buttoned three quarters
up the front, leaving a bit of bra exposure, but which I thought looked
very nice with the jeans. Finally, I found a pair of three-inch black
heels among Grace's shoes that I thought would make my look believable.
I then sat down to Grace's makeup table and applied the makeup that I
would need for the day. I next fixed in place the long auburn wig, put
on some earrings, and then grabbed the lipstick I was wearing in case I
needed to refresh during the day. I then went to the kitchen, fixed a
quick bite to eat and a cup of coffee. Finally, I double checked that
everything I needed to dress at Mandy's was packed, slung the bag over
my shoulder, and headed out to face the world for the first time dressed
as a woman. Little did I realize how ill-equipped I was to take such an
excursion alone.
My stomach was in knots as I rode the elevator down to the apartment
lobby. The only saving grace to the situation for me was that I did not
live in the apartment, so no one knew me as a man. The only person who
did know me as Dan - er, Danni - was the doorman, Walter. Thank
goodness he was going to be off this morning. So I thought I might be
able to pull it off.
Unfortunately, despite no one knowing me as Dan Thompson, I had my first
test before even reaching the lobby. The elevator stopped on the ninth
floor and an attractive, tall, well-dressed man entered the elevator.
"Good morning miss," he greeted me.
I was completely unprepared for the possibility that I might have to
speak to anyone. Of course, we speak to strangers throughout the day
during our normal lives and don't think a thing of it, until we're in
unfamiliar territory, which I was in. I couldn't be rude and not return
the casual social greeting. But would my voice reveal me as a man? My
upbringing would not permit me to be rude.
"Good morning," I whispered in a breathy, low voice.
The stranger looked at me appraisingly. What was he thinking? Had I
just given myself away?
"Looks like it's going to be a beautiful day," he commented.
Okay. That was a good sign. He was continuing normal conversation.
"Yes, it does," I agreed in my breathy voice. I had no idea whether I
sounded like a woman or not. I could only hope.
Nothing further was said as we completed the ride to the lobby. As he
exited, he smiled and wished me a nice day.
"You too!" I replied as I stepped off in front of him while he held the
door for me. That felt weird. Normally, I'd be the one holding the
door for a lady.
As I began my stroll across the marble lobby floor, my heels echoing as
I walked, my eyes must have become the size of quarters. Guess who was
manning the front door? That's right - Walter! What was he doing here?
Grace had assured me he'd be off. I prayed he would not recognize me or
say anything.
He watched me as I approached. Was he sizing me up? Did he know who I
was? As I got nearer, he went to hold the front door for me.
"Good morning Miss?" he greeted me, giving no indication that he
recognized me. The only problem was that, again, I was unprepared for
the outside world. Who was I? What was my name? I couldn't think fast
enough and so I reverted to what came natural - my actual last name.
"Thompson," I replied. "Good morning."
"Yes! Miss Thompson! Have a nice day ma'am," he said cheerfully as I
walked past him onto the sidewalk and toward my parked car.
My heart was beating a hundred miles per hour I was so stressed, and
yet, excited from the situation. Did he know? Had I ever told Walter
my last name? I couldn't remember. I hoped not. Was he smart enough
to put two and two together? I'd wonder every time I saw him when I
entered Grace's building.
Suffering from the stress overload of my first five minutes dressed as
woman in public, I hurried to my car. Although I'd become fairly
comfortable walking in heels, I'd never done it in public where I found
I was inordinately concerned with strangers sizing me up, as if anyone
was actually even noticing me. Plus, I'd never worn heels when I found
I was in a hurry, which I was. I wanted to get inside of the protective
cocoon of my car quickly so I wouldn't have to speak to anyone else
until I arrived at Mandy's. Unfortunately, unlike the even, level floor
in Grace's apartment, and my own home, sidewalks have cracks, and as a
consequence, I was unprepared for the concrete edge that, in my rushed
steps, I accidentally caught on one of my heels, leading to disaster. I
tripped and fell, my shoulder bag falling open as I did. Before I could
gather myself, I was being helped up by a man who'd seen me trip.
"Are you alright miss?" he asked with true concern in his voice.
Flustered and embarrassed beyond belief, I managed, "Yes. I think so,"
as I quickly realized that some of my maid's uniform had spilled out of
my bag. I quickly grabbed at the bra and lace lined panties that were
lying on the sidewalk just outside of the bag. Did the stranger who was
helping me see them? Oh God! If he did, what must he think of me? Who
wore a French maid's uniform other than a whore?
As I reached for the clothing, he said, "Let me help you with that.". He
managed to beat me to the panties. He held them out for me and I think
it was only then that he even realized what he'd just picked up.
"Uh, here you are," he said, holding them out to me, suddenly as
embarrassed as I was.
"Thank you," I answered, my face as red as my nails. "I'm sorry," I
said, though I wasn't completely certain what I was apologizing to him
for. For falling? For him picking up my panties? For being a man
dressed as a woman? I didn't know. All I knew was that I wanted to get
inside my car and get as far away from him as I could.
He just stood there, as if he didn't really know what to say. "It's,
it's okay ma'am. I hope you didn't hurt yourself," he offered,
returning to concern for my well-being.
Grateful that he wasn't making an issue of the panties as I stuffed them
back in the bag, I said, "I'm fine. Thank you very much," I said as I
moved toward my car.
He watched me as I put my bag in the rear seat and climbed behind the
wheel. He smiled and waved as I drove off and I gave him a smile in
return and waved back.
God! What a morning! I didn't know whether I'd survive the day.
During the drive to Mandy's I managed to relax. Even the simple act of
driving had me on edge as, at every stoplight, or whenever a man drove
by me, I worried whether I was being made as a guy wearing women's
clothing.
Finally, I arrived at Mandy's home. She lived in a neighborhood in
Arlington, Virginia that was made up mostly of young professionals. It
turned out that Mandy, despite her appearance as a blonde bimbo type,
was a CPA, with a major accounting firm in D.C.
I nervously approached Mandy's front door, concerned that I'd already
demonstrated to myself how poorly equipped I was to navigate the outside
world alone while masquerading as a female. It had been one thing to be
in Mandy's presence with Grace there as my protector. Spending an
entire day with Mandy was something altogether different. I was
worried.
I rang the bell and waited. Mandy opened the front door smiling,
"Sissy! Good morning! Thank you so much for agreeing to help me
today!" she announced cheerfully. "My, my! I love your jeans! They
look so good on you!"
Mandy was dressed in a white tennis outfit. The short skirt showed off
her tanned legs. She must play a lot of tennis I thought. That's
probably why she looked so fit.
I smiled gratefully at her compliment. "Thank you Miss Stratton," I
answered, remembering my role as maid for the day.
"Oooo! I love that Sissy!," she exclaimed. "What's in your bag?" she
inquired.
"My uniform," I answered.
"Your uniform?!" she repeated. "Oh! You're going to dress for me
today?"
Dress for her? I'd thought it was expected that I would have to dress
as a maid for purposes of helping her prepare for her party.
"Er, ah, ye, yes," I replied. "I was told by Miss Andrews to bring my
uniform."
"Oh wonderful!" she said gleefully. "Let me show you where you can
change. Then we can get started. I can't tell you how much I
appreciate your willingness to help today."
"It's no problem at all ma'am. I'm happy to help," I responded as I
followed her to a spare bedroom where I was able to change. I removed
my blouse and jeans, folded them neatly and placed them on the bed to
change back into later in the day. I then unpacked the uniform I'd wear
as I worked for Mandy.
As I began donning the lingerie beneath my uniform, I reflected on how
much I'd come to enjoy the ritual of dressing in sexy women's under
garments. As much as I tried to convince myself that I only did so for
Grace, I couldn't deny what I knew deep down - I liked wearing feminine
attire. But I insisted to myself that enjoying the feel of lingerie did
not make me a si, si - well - what Grace kept calling me. I wasn't one.
I wasn't.
I fastened the shiny black garter belt around my waist. It was a long-
lined garter belt that rode high on my waist and provided some tummy
control, in addition to holding my stockings. Grace had provided a new
pair of stockings for me to wear. It wasn't until I opened them that I
realized that they were not like the stockings I'd ever worn. These
were fishnet stockings with a wide lace welt to fasten at the garter
belt. They had a black back-seam that had to be lined up. There was
something about fishnet stockings that seemed so much more, well,
slutty, than any others that I'd worn. Next came the panties. The ones
the stranger who helped me after my fall had seen. They were a French-
cut panty and the bottom was lined from the waist to the crotch with
white lace ruffles. I knew that whenever I had to bend over, anyone
standing behind me would see the ruffles. I suppose that was part of
the point to them as part of the uniform. I then stepped into the full,
layered white petticoat slip that would lift my dress and give it a very
sexy appearance. I slipped my five-inch black paten leather heels on
and stood in front of the mirror examining my body without a wig, bra or
breast forms. This was when I was most uncomfortable with what I had
allowed myself to be led into doing. I looked feminine, but not quite a
woman, and definitely not a man.
To remedy the situation, I shut it out of my mind and quickly picked up
and fastened the bra around my chest. As soon as I did, I filled it
with the DD breast forms that provided a full, feminine form to my
shape. I picked up the French maid's dress from the bed and slipped it
over my head, letting it settle over the petticoat and admired the way
it flared out to the side. It was shorter than the dresses Grace had me
wear while working for her. I couldn't help wondering if it wasn't
intentional on her part to dress me this way in front of Mandy. Next, I
tied the apron around my waist and then turned to fix my wig back in
place.
Looking at my visage with the wig changed my outlook. I was a pretty
and sexy looking maid. I capped the uniform off with the cute little
maid's cap and then checked my appearance once more before heading out
to go help Mandy get ready for her party.
As I walked, the rhythm of my heels clicking on the hardwood floors in
Mandy's house drew her attention to me. When she saw me her hand went
involuntarily to her mouth as she gasped at the sight of me.
"Oh! My! God!" she exclaimed. "You look amazing Sissy! I can't
believe how beautiful you are! I've never seen an actual maid who
looked so hot!"
I was embarrassed and blushed. "Th, thank you Miss Stratton," I
responded shyly. Trying to change the subject I asked, "So, where would
you like me to start?"
Still staring in disbelief of my appearance, she gathered herself and
said, "Okay, there is quite a lot to do to get ready. Mostly, what I
was hoping you could do is basic house cleanup. That's the main thing.
That will free me up to get ready for the party. When you finish with
that, then if there is still time, I may get you to help me with some
other things. Okay?"
"No problem ma'am," I agreed, settling into my role easily. "Where
would you like me to start?"
"I have a feeling that some of my guests may end up staying here
tomorrow night after the party, so I'd like to change the bed linens on
all of the beds. I have four bedrooms, so if you could start there,
that would be great. Then, if you'd clean all of the bathrooms and
perhaps, while you're at it, if you do my personal laundry that would be
wonderful. All of the cleaning supplies are in the utility room,
including the soap you'll need for the delicate items."
Delicate items? She meant for her underwear. I knew. Involuntarily,
my penis twitched inside of my panties at the thought of washing Mandy's
intimates. "Yes ma'am," I replied, and swished off to the utility room
to get started. I say 'swished,' because that is the sound my petticoat
made whenever I walked, and so it is the only way to describe how I
walked, especially in five-inch heels.
I went to each bedroom and stripped the beds of everything. I then
began the process of washing all of the sheets. While the dirty linens
were being washed, I found clean ones in the hall closet and began
remaking all of the beds. I then dusted each bedroom. I was just
finishing the last bedroom when Mandy walked in to check on me. I was
on a step stool reaching up to dust above her window frame, on my
tiptoes. I knew my lace panties were revealed clearly beneath my dress.
"Sissy?" she asked, while lewdly staring at my ass. "Would you like a
snack or something to drink?"
I was hungry and thirsty. "Yes ma'am," I answered. "That would be
nice."
"Why don't you take a break then and join me on the patio. Like they
say, 'All work and no play...'," she giggled as she walked away.
I finished the bedroom I was doing and then joined Mandy on her patio.
Her back yard was lovely! The landscaping was immaculate, with a
beautiful rose garden surrounding a water fountain that fed into a Coy
pond. Mandy was sitting a small table for two eating a sandwich. There
was a place set for me. I settled onto the seat, draping my skirt out
carefully as I sat. Mandy smiled as she watched me get comfortable.
Grinning she said, "I just can't get over how sexy you are Sissy! And
such a good maid! I've never had anyone who dusted as thoroughly as
you. You don't happen to have any free days do you? I'd love to get on
your schedule."
I blushed at the compliment. "Er, ah, I'm sorry, but I don't think so
Miss Stratton." I tried to be polite in my refusal.
Mandy didn't seem to be upset. She continued the conversation though.
"You know, I really was surprised at first to learn that Grace had a
maid. I didn't know she had a need for help around her apartment.
She's so seldom there. Of course, that was before I knew some of the
other, ah, services you performed," she said with a wink and a smile.
I shifted nervously in my seat. I was uncomfortable with the direction
the conversation was taking. I said nothing as I looked down at the
food on my plate to avoid eye contact with Mandy. When I looked down I
noticed that Mandy had her legs spread open enough that her tennis
panties were showing from beneath her skirt. It almost seemed
intentional. I was wondering what Mandy was implying when she commented
upon how she could understand that Grace would be drawn to my 'special
services.' I certainly understood what she meant by 'special services.'
And why wasn't Grace usually not staying in her apartment, as Mandy
indicated? As far as I knew, she always stayed there. On the other
hand, I was only there with her on weekends. Who knew where she stayed
during the week. Mandy, on the other hand, was a close friend. Surely
she'd know of what she spoke.
"How was it Grace said she met you again?" Mandy interrupted my
thoughts.
"I, ah, she, we, met one night in a bar," I repeated Grace's
explanation.
"That's hysterical!" she laughed. "Who would ever believe one could
find a maid, especially one as beautiful and sexy as you, in a bar!"
I laughed nervously. I wanted out of this conversation. Once again, I
found myself ill-equipped to handle