Happily Ever After- A Princess at Disney World Part 4
Just want to give a warning. There is going to be a delay between the
this Part and Part 5. I ran down to Disney World for some additional
research and between that and other commitments I haven't had as much
time to write. I promise Part 5 is coming along with Part 6 after that.
I apologize for the delay.
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I had woken up about six fifteen and tried to go back to sleep. It had
been after midnight by the time we crawled into bed last night and I was
hoping to sleep a little later. We had a great time and I had honestly
loved wearing the Tinkerbell costume that Sarah, Pat and Jordie had
surprised me with. They had been Wendy, Ms. Smee, and a sexy female
Captain Hook.
Sarah and I had a few ups and downs again, although I think by the end
of the evening, we were okay. I was beginning to think I was just going
to have to accept that was going to happen and it was a part of her
acceptance, or maybe it was how she tolerated my crossdressing, along
with my interest in sex with men.
As I thought about the later part, I reached down and twirled my
engagement ring on my finger. While I knew it wasn't real, it did make
me smile, and I liked knowing that in two days I would have a chance to
spend time alone with Steve. I also thought about how much I had
enjoyed flirting with Matt, who I had just met. I don't think Sarah
realized how much their attention, and attraction to me, made me feel
like the female me was accepted.
I gave up on sleeping and slipped quietly into the bathroom to pee and
for a quick shower. My legs were still smooth, so I did not shave them,
but I closely shaved my face again after I got out. I dried off and did
my make up.
I didn't want to run the blow drier, possibly waking Sarah up, so I did
the best I could to dry my hair with a towel and put my hair into a pony
tail. I could hear Sarah snoring and looked at the time on my phone.
It was a little before seven o'clock, she wouldn't be waking up for
about an hour.
I slipped on a pair of pink bikini panties and a pink bra. Stepping
back into the dressing area I slid my forms into the bra and get a new
panty liner for panties. I had laid out the khaki shorts I had worn
yesterday morning and pulled them on. Then added my pink Disney
Princesses t shirt with Girl's Just Want to Have Fun written on it. I
grabbed my pink Magic Band, sunglasses and put on my flip flops,
admiring my toe nail polish.
I slide out of the room, gently opening and closing the door. I wanted
to get some coffee and I knew the machine in the room would have woken
Sarah up. I headed to the restaurant I got a coffee and yogurt. I took
them to the outside tables and sat to watch the resort come to life.
I scrolled through the Photopass pics on the my MyDisney Experience App.
I loved seeing the smiles on Pat's and Jordie's face on the pics they
were in. I also enjoyed seeing myself. It seemed like my smile was
different as Brandi. Maybe it was the make up making my eyes more
expressive but there was a difference.
"Hey Tinkerbell. Sorry, I couldn't resist. It is Brandi, right?" I
looked up and Matt was standing next to the table I was at.
"Good Morning Matt. Yes, it is Brandi. Tinkerbell went back to
Neverland." I smiled.
"Did she go back to Neverland without finding Peter?" He had a cocky
grin and looked right at me.
"Oh, that was good. You are definitely better at this than me." I
bated my eyes as I said it.
"Thanks, I think. What are you all doing today? Going to the parks?"
he asked.
"Yes, going to Hollywood Studios a little later in the morning, the
others are sleeping in. What about you all? Where are your kids?"
"They are still sleeping, or at least I think they are. My daughter
wanted to do a sleep over in my sister's room last night with her
cousins. And my son stayed in my brother and his wife's room with his
cousin."
"So, you were all alone in your room last night? That must have been
lonely." I winked at him.
"Okay, maybe you are better at this than you give yourself credit for."
he replied. "Can I ask a personal question?"
"Sure, and I might answer it." I think the confidence in my voice had
diminished.
"Fair enough. I see that ring on your finger, although you obviously
enjoy flirting with me, which is okay flirting is just flirting. What
puzzles me is I also see how, I think it is Sarah, and you interact or
look at each other. What is going on there?" He had definitely lost
confidence as he spoke.
I took a few seconds and then after a deep breath replied. "Not sure if
this will shock you, anger you, disgust you, maybe all of those things,
especially after the flirting. You seem like a decent guy, so I am
going to tell you the truth."
"Pretty sure you aren't going to shock me, or any of the other things,
if you say what I think you are going to say, the only bad thing will be
having to admit to my little sister she was right and I will owe her a
drink from our bet." He gave me a half grin.
I glanced up him still trying to find the courage to say it out loud and
disappointed that I had to. I was going to miss the flirting even if it
was just for today.
"Yea, that figures. A woman would definitely pick up on it sooner. So,
to get right to the point Sarah is my wife and she isn't a lesbian,
which is my cryptic way of telling you I am not what I appear to be. I
hope you understand what I am saying because I don't want to actually
say it. Although this week she is more of roommate and one of my
girlfriends. We are still trying to figure all of this out."
"I understand. And I won't make you say it. If... if you explain the
ring and the flirting."
"That is fair. So, the ring is a cubic zirconia engagement ring to be a
Disney Princess. I was proposed to at the Magic Kingdom on Wednesday
afternoon. Sarah set it up so I could experience being proposed to as a
woman." I had gained a little confidence as I spoke.
"Wow, really? So, Sarah proposed to you, while you were dressed up?" he
asked.
I chuckled. "Umm, no. I can't decide if it is because I am embarrassed
telling you these things or if I am just assuming you would know things
that you would have no way of knowing."
He laughed. "Don't be embarrassed. This is all fascinating to me and I
promise you I won't judge."
"Thanks, so I have only been out to Sarah as crossdresser since early
March. We were on a Disney cruise when it all came out. I also told
her that I was interested in certain, let's say experiences with men
while we were on the cruise." His eyes widened as I said that.
"We met a family on the cruise and became friendly with them. The
husband of the woman and I became, uh, close." I had lowered my face as
I said that.
"Really, like real close? And Sarah and his wife were okay with that?"
His tone wasn't judgmental it was curious.
"Yes. Sarah told me she wanted me to have those experiences and
honestly intimacy isn't really a part of our relationship these days.
The wife and he had an arrangement before they met me. She allowed him
to be with other people who were willing to do certain things, she
didn't want to."
"Things?" He raised an eyebrow and smiled.
"I will let your imagination go wherever you want with that." I winked
at him. "Anyways, they surprised us, or me actually, on Wednesday and
showed up at Disney and Steve, that is his name, proposed to me in front
of the castle by asking me to be his Disney Princess."
"Well, that explains the ring. What about the flirting with me?"
"Honestly, you are really the first man I have done that with besides
some with Steve on the cruise. You are good at it, it is fun, and it
makes me feel more feminine and like a woman. Plus, your kind of hot."
I smiled at him.
"Kind of?" He laughed. "Well, you are fun to flirt with too, you
definitely look like a woman, and you are hot. My sister hates that you
have such a great ass and legs, she doesn't think it is fair."
I laughed. "Tell her it is some genetics, but it is also a ton of squats
and hours on the stair machine. You never said what you all are doing
today?"
"Animal Kingdom this morning. Then pool time and having dinner at
Hollywood and Vine tonight followed by Fantasmic," he responded.
"I love Fantasmic. We are going to watch see it on Monday evening, our
last night."
I looked at the time on my watch. I need to head up to the room and
change into my tennis shoes plus make sure Sarah was awake. I stood up
and put my hand on Matt's forearm, surprised that caused a little charge
to run through me from just that small amount of intimate contact.
"Thanks for a great start to the day you are so easy to talk to. Maybe
I will see you at the pool later this afternoon? I would love to flirt
with you some more." I smiled and headed back to my room.
"I really hope so. Have a great time this morning Brandi." I looked
back over my shoulder and saw him watching me walk away.
Sarah was up and finishing dressing when I entered the room.
"Hey, what have you been doing this morning? What time did you get up?
You look like you are ready for the day except for your shoes," she
asked as she walked towards the dressing area.
I hesitated to answer, worried what her reaction would be. "I got up a
little after six, just woke up wide awake so I showered and got ready.
Then I went to get some coffee and ran into Matt, so I was chatting with
him."
She quickly turned her head around when she heard me say Matt. "Really?
What did you all talk about? And you just happened to run into him?"
"I was sitting at one of the outside tables and he walked up. Umm. He
actually asked about you and me. He, and his sister, I guess had picked
up on.... things..."
"Really, and what did you tell him?" She had moved closer to me.
"Pretty much everything. He was very easy to talk to." I was finishing
putting my tennis shoes on.
She sat on the bed next to me. "And he was okay with you or you know...
that you are actually not a woman?"
"Yes. Even told me he hoped to see me later so we could flirt some
more." I wasn't sure why I was so proud when I said that.
"Wow. Just be careful with that. What do you think Steve would say if
he knew? Don't mess anything up for Sunday, a lot of work has gone into
that." She had put her hand on my thigh and looked directly at me as
she said it.
"Well, I don't plan to tell Steve. And it isn't like this is real." I
held up my hand to show my engagement ring. "Plus, it is just
flirting."
"Okay, but I bet given the chance you would be happy to do more than
just flirt, right?"
"Uh, probably," I said now looking down.
"I knew it. Slut!" She laughed and stood up. "Honestly, glad you are
getting this experience."
I quickly touched up my makeup, grabbed my Rose Gold Ears and back pack,
put my pink Magic Band on and I was ready. I noticed Sarah was wearing
shorts today. They were longer than mine, but they fit her butt well.
I was behind her as she pulled up the door. "Hey, you look good. I
like those shorts."
She laughed. "You like my butt in these shorts. I know you. Speaking
of butts, wow Jordie. You know Disney is a family place."
I hadn't seen Jordie when Sarah first opened the door, but she was
leaning against the railing with her back and butt to us. Sarah was
right, she had on a pair of short, tight, white shorts that hugged her
curves. When she turned around you could see her makeup had been done
to match her lavender v neck shirt. She looked fantastic.
"Wow, girlfriend, you look amazing," I said.
"Thanks. You look good also, pink is a good color for you." She
smiled.
We headed to breakfast, all of us choosing share beignets and avoiding
covering ourselves with powdered sugar. Sarah and I told Pam and Jordie
to make sure that they would be hungry for dinner tonight. We quickly
ate and took our coffee and coke with us to catch the bus.
We lucked out and the bus was pulling up right as we got to the bus
stop. Hollywood Studios was a quick bus ride and because we were going
after the rush to be there at rope drop, it wasn't crowded. Bag check
and security were painless and soon were headed to Tower of Terror, our
first Fastpass.
Hollywood Studios is smaller than all the other parks which makes it
easy to get around. We quickly arrived at the ride. The theming for
the Tower of Terror is fantastic. We heard a family behind us talking
about how scared they were. When they asked if we had ridden it before
and if it was really scary, we told them no. We did tell them that the
anticipation was very scary and that is what made the ride fun.
The ride ended and we headed out through the gift store. We saw the
family that had asked about the ride while we were in line, they told us
we were right about the anticipation being the worst part and they loved
it. I told them they had to ride it again because the drop sequences
changed and that we had only had a fair one. They thanked us and headed
out.
We walked out and made the short walk to RocknRoll Roller Coaster. This
was Sarah's favorite ride. The standby line said it was a forty-five-
minute wait, but we could see that the single rider line was inside the
door. We explained to Pat and Jordie that it would probably be twenty
minutes or less.
We entered the line and got held up just inside the door for five
minutes before we were moved through to the pre-show area and eventually
the single rider queue line inside.
"So why is this your favorite?" Jordie asked.
"I don't know. I just like it. It is fast, the music is fun. The only
bad thing is it is over way too fast. It only lasts about 47 seconds,"
Sarah replied.
"Oh, sounds like my ex-husband." Pat laughed.
"Mom! TMI, that is my dad you are talking about," Jordie said but she
was smiling.
Our line moved fairly quickly. "Same bet as Everest?"
"Sure," Jordie said quickly.
"I am in," Pat added.
"What is the bet?" Sarah asked.
"Whoever gets the hottest ride partner has to buy drinks at the pool
this afternoon," I said.
"Okay, and for an added side bet. If you win AND your song is "Dude,
Looks Like a Lady" you have to buy two rounds." Sarah grabbed my arm as
she started to laugh.
"What is the song part?" Pat asked.
"Each ride vehicle plays different Aerosmith songs while you ride, it
definitely adds to the fun," Sarah told her.
"Okay. I will take that bet."
We moved up and Pat went first. Her partner was a young teen girl.
Jordie was next and she ended up with the mom of two tweens who were the
seats in front of her. I was next and got a balding, beer bellied
husband and dad, whose wife and kid were in front of us. Sarah was last
and she was partnered with the grandfather of a family group. He was
probably early sixties and looked good for his age. His face showed he
was pleased with his ride mate.
My ride partner almost fell over climbing into his seat and struggled to
get seated. I was surprised the effect my breast forms had on getting
the restraint to sit comfortably down over my shoulders. I laughed when
the ride started, and we shot down the track into the loops and realized
that the song was "Dude Looks Like a Lady." I looked over at my ride
partner and was a little worried he was going to wet his pants. His
daughter's screams from the car in front of almost drowned out the
music.
At the end of the ride, we all met in the gift shop and walked out,
stopping at the little girls room just outside of it for a quick pee
break.
"Okay, I think I am with Sarah, that has been my favorite ride so far,"
Jordie said. "I also think Sarah owes us drinks."
Pat laughed. "Well, I know that you and I aren't the ones buying."
"So, you all are saying you didn't think Brandi's partner wasn't hot?"
Sarah laughed. "He definitely thought she was hot. He almost fell over
getting in the ride because his eyes were glued to her ass while she was
getting in."
"Is that what happened?" I asked.
"Yes. The best part is I think his wife saw it also. Oh, did you get
the song?" Sarah was smiling.
"Yes. Guess he didn't know he was living it." I chuckled.
We were headed to Toy Story Land and had some time to kill before our
Fastpass for the Slink Dog Roller Coaster, so we decided to catch the
Little Mermaid show. I knew Sarah would like that and it would give us
a chance to sit in the air conditioning for a little while. The show
was becoming a little dated but still cute.
We left the show and tapped our Magic Bands for our Fastpasses for Slink
Dog five minutes before their start time, which was acceptable, so we
got the green circle that allowed us to enter. The ride is a family
roller coaster so not as fast as RocknRoll or Everest, but it is a fun
ride.
We were off it at just after twelve o'clock and headed over the Baseline
Tap House. We each got a beer flight and ordered two pretzels. This
was a must stop for me when I was here as Brad and Brandi had decided
that girls can enjoy a beer also.
"So, Brandi spent the morning with Matt," Sarah announced.
"Define, spent. You didn't have a protein shake to start the day, did
you?" Pat laughed.
"No, I had coffee, seated at one of the tables, and he stopped at
chatted with me." I gave Sarah a harsh look.
"What, just making conversation." Sarah winked at me.
"Was he flirty McGee with you this morning?" Jordie asked.
I blushed. "A little. He knows about me and we talked about that and
did flirt some, even after he knew the real deal."
"Oh. Very cool. How is it though, once again, you are in the lead in
the most likely to get some dick competition?" Jordie said while
winking.
I was surprised to hear that come from Jordie, but I laughed.
"In the lead... she already won. She got some the second day,
remember," Sarah said.
"Oh, yea, that's right. Slut." Jordie winked at me this time.
"Jordie, even you? That is the second time today I have been called a
slut." I smiled at her.
"Well, if the come fuck me heels fit." Pat laughed.
We finished our flights and pretzels, then walked the short distance to
Star Tours, our last Fastpass. In comparison to Flight of Passage at
Animal Kingdom, or Soarin at Epcot, the motion simulator technology is a
little outdated but Pat and Jordie enjoyed it. It was the first time
Sarah and I had ridden it a few years.
On our way to the front of the park we decided to check out the single
rider line for RocknRoll Roller Coaster. The line for single riders was
just outside the entrance door so we decided to ride it one more time.
None of us got a ride partner worth noting and we were at the bus stop
for the ride back to the resort right after three o'clock.
On the bus ride back Jordie asked, "What are you wearing tonight? I know
it isn't super dressy."
I quickly looked over at Pat and Sarah. They weren't paying attention.
"Um. You are right but I am wearing a new dress tonight that is a
surprise. Sarah hasn't seen it yet. When I unpacked and hung it up, I
hide it behind a couple sundresses."
"Oh, is it really dressy? I brought a new body con dress but thought it
might be a little much?"
"I don't think so, but I am sure Sarah will think it is. She always
thinks I am overdressing. If you wear your new dress I won't stand out
as much." I smiled.
"Okay, what about shoes? I have some heeled wedges."
"Those would be fine. I have a pair of peeped toed sling backs with a
three-inch heel I am going to wear. Sarah isn't going to be happy. I
am glad you will have heeled shoes on, I won't stand out as a giant when
we are walking." I gave her a big grin.
I was honestly really looking forward to dressing up tonight. I was
loving being able to be a girl the whole time, but I was missing dresses
and heels. Sarah sometimes chastised me about wanting to wear heels all
the time saying that most women couldn't wait to take them off. I
understood that but she didn't understand that I was trying to make up
for over thirty of not being able to wear them.
We got back to the resort and made plans to meet at the pool after we
changed. I had changed into my bathing suit behind the curtain of the
dressing area and found Sarah laying in the middle of the bed still in
her clothes.
"You really look good in that bathing suit. Just so you know." Her
tone was genuine, and she was smiling at me.
"Thanks, do you want me to wait for you to change?" I asked raising an
eyebrow.
"I think I am going to take a nap here. I might come down later. I
have a little headache plus it is pretty hot out, not really my thing,
but you enjoy that warm weather."
"I am sorry. Anything I can do?"
"Nope, thanks. Just turn the light off on your way out."
I gathered a couple of things to take with me and headed out. When I
got to the pool, I noticed it was a little more crowded than the last
couple times we had been there. Jordie had found two lounge chairs and
when she saw me, she pointed them out. She told me her mom was at the
pool bar getting a drink. I put my stuff down on one the chair and went
to meet Pat at the bar.
"Can you add one more of whatever she ordered?" I asked the bartender
and he nodded yes.
"You really look great in that suit," Pat said to me.
"Thanks. I like your suit also." I eyed her cleavage as I said that.
She laughed. "Well, it does let me show off my best feature."
"Your best feature is your smile, but those are a very close second." I
winked. "I would show them off also if I had them."
The bartender handed us our drinks and we walked to the chair.
"Do you wish you really had them to show off? Not forms but ones you
had all the time?" Pat asked as we walked.
"I think so. I don't know. Please don't say this to Sarah but I think,
if it weren't for family things, I think Brandi would be here pretty
much all the time. I really don't know."
"Oh wow. I won't say anything but wow. That is a huge step," she
replied.
We got to the chairs and didn't see Jordie. Pat finally spotted her in
the pool and asked. "Want to join her and have our drinks in the pool?"
"Um, I probably shouldn't so that. Uh, I am wearing something to make my
front flat that probably shouldn't end up the pool. Not sure what would
happen. How about I sit on the edge and you all can enjoy the pool."
"Sounds good."
Pat and Jordie stood in the water, while I sat with my legs dangling in
the water. We pointed out a few of the dads to each other and I also
got up and got us a second round of drinks. Pat had decided the drinks
had made her ready for a nap in the lounge chair and got out of the pool
and went and laid down. I was getting ready to join her when I saw Matt
and his kids enter the pool area. He saw me and waved which I returned.
"He is definitely cute, and he is into you. You can see it in his smile
when he saw you." Jordie chuckled.
"I don't know. I mean I know he is cute, obviously. Not sure about the
into me. I think I am novelty to him."
He had found a lounge chair and put the kids' stuff on it before
spraying them down with sun screen. He had his back to us as he took
his shirt off and when he turned around, I might have gasped. It was
obvious he spent some time in the gym. His stomach wasn't a six pack,
but it was definitely toned and flat.
"Oh My!" Jordie said.
"Yes, oh my, my, yes that is impressive." I watched him walk into the
pool as both his kids jumped in.
They started on the other side of the pool area but were slowly making
there way across to where we were.
"I think I am going to go join mom and take a quick snooze. Looks like
you will have some company soon. Have fun." She winked at me and made
her way to the stairs and out of the pool.
Sure, enough Matt and his kids were close by a few minutes later.
"Wow, Emma you are great swimmer. Are you sure Aerial isn't your
favorite princess and you actually a mermaid?"
"No, I told you Cinderella is my favorite. See." She had climbed out
of the pool and was showing me her Cinderella swim suit.
"I do see, and you did. That is a very pretty bathing suit."
"Thanks, watch this." She yelled as she ran and jumped into the pool.
When she came up out of the water I was clapping and told her it that it
was amazing. Austen was being thrown into the water by his Dad and I
was admiring Matt's muscles in his arms and shoulders each time he
tossed him. I heard him tell Austen one more time because he was
getting tired and then Matt was next to me.
"I was hoping I would see you. How was your day?" he asked.
"I was hoping I would see you also. It was good. How was Animal
Kingdom?"
"Fun, the kids prefer the Magic Kingdom though. Do you have a favorite
park?"
"Honestly, I like each of them for different reasons. I really don't
have a favorite."
I heard his kids yelling and looked over and saw that the other kids
from the their group had just got into the pool. Emma asked if they
could go over to them. He told them yes but to stay with the group. He
waved to his sister-in-law who waved back while shaking her head but
smiling.
"Was the head shaking what I think it was?" I asked.
"What do you think it was?"
"A subtle, you are hanging out with her again, with a questioning tone
on the word her, and a heavy accent on the again."
"You are probably right about the again part. She would never question
the word her, in fact she was telling me how brave she thought you were
earlier." He smiled up at me.
"Really? Why were you talking about me earlier?" I grinned at him.
"I was telling her and my sister that they were right while also telling
them how much fun I had chatting with you this morning." He winked at
me.
"You were? I had fun also. It was a nice start to my day."
"What are you all doing this evening? Going back to the parks?"
"No, we are having dinner at the Yachtsmen. It is the best restaurant
here in my opinion. Plus, it will be a reason for me to get a little
dressed up."
"Dressed up at Disney? I thought that was one of the great things about
being here, a t shirt and shorts is the dress code everywhere." He
laughed.
"Yes, dressed up. It is a girl thing you wouldn't understand." I
laughed.
"I probably wouldn't but I think I am going to be disappointed that I am
going to miss seeing it." He gave me another fantastic smile.
"Hey Brandi, we are heading up. What time do we need to be ready to
go?" Jordie yelled.
"How about a little after seven. We can have drink at the bar there
first if you want?"
"That sounds good. We will be ready then," she replied.
I turned back to Matt. "What are you doing after dinner tonight?" he
asked.
"I don't know. Probably coming back and going to bed," I responded.
"Well, if I can find someone to watch the kids maybe we could have a
drink either at the bar here or over at Port Orleans Riverside?" He
actually looked a little nervous and raised and eyebrow as he spoke.
"You really want to see what I looked like dressed up huh?" I grinned.
"Yes, but I also just like chatting and flirting with you. So, you
interested?"
"Yes, how will I find you tonight?" I asked.
"Do you have your phone down here, I will give you my number and you
text me when you get back?"
"Yes, over with my bag." I got up and walked over to the chair.
When I got there, I made a point of bending over at the waist to get my
phone out and then peaked back to make sure he was checking out my ass.
He gave me his number and I put it in my phone. I decided it was time
to head up to the room. I had already planned to go a little heavy on
the makeup this evening before I had a potential date now, I was
wondering if Pat might be able to do a little more with my hair also.
"I am going to head out. I will text you later. It was great to see
you this afternoon, have fun watching me walk away." I winked at him.
"I definitely will." He smiled.
I was really surprised at my level of confidence in flirting with him.
I couldn't decide if I was more comfortable being Brandi these days, or
I was feeling more comfortable flirting, or if Matt just made it easy to
do. It was probably all of those things together.
I entered the room and Sarah was laying on the bed in her towel. I
quickly moved through the room and got in the shower. When I was done,
I let the steam escape and she moved over to start drying her hair. We
each took a turn doing that and were starting on our makeup.
"Was your new guy at the pool?" Sarah asked.
"New guy? Do you mean Matt? If yes, then he was there," I said a little
defensively.
"And? Did you all talk or anything?"
"Yes, we talked. He is easy to talk to." I was still defensive and
wasn't sure I wanted to tell her about our plan to meet later.
"Who do you like better, Steve or him?" She was looking right at me as
she asked.
I hadn't thought of that yet. "Honestly, I don't know. Steve is great,
treats me nice, the sex is fun but it seems like when it is all said and
done, sex is really what it is all about with him. Not that I mind." I
laughed a little at the end.
"Do you want to have sex with Matt? Or is it something else, do you
have, feelings or something for him?"
"Feelings? I wouldn't go that far, it is just, easy to talk with him
and honestly flirt with him. It seems natural or something." I was
literally thinking and talking out loud.
"And what about sex? Do you want to have sex with him?"
"Well, I wouldn't turn down the chance. He is cute and he looks really
good without a shirt." I laughed.
"Okay, just remember two things, all of that is okay with me as long as
you are honest and don't fuck anything up with Steve before Sunday. If
you can manage that then I am pretty sure Steve will be fucking you on
Sunday." She laughed.
I didn't tell her about my plan to meet Matt later. I figured I would
do that after dinner. "Okay, I am going to tap on Pat's door and see if
she can add a little curl or bounce to my hair for tonight."
Pat was wearing a new sundress when she opened the door. I told her she
looked good which was true and asked for a little extra for my hair.
With the magic of some brushes, a blow dryer and a curling iron my hair
looked fuller, sexier, and younger.
Back in our room I finished my makeup. It was definitely the heaviest I
had done it on the trip so far. It helped make me look younger also.
While I was finishing that Sarah had gotten dressed. I stepped out the
dressing area to get my bra and panties. I was going to wear the
strapless bra from my Tinkerbell costume. The cap sleeves on my dress
would probably hide my bra straps but I decided I didn't want to take a
chance. I grabbed a white thong also.
Stepping back into the dressing area I pulled the curtain back into
place and put my undies on. I placed my forms and then slide my new
dress from behind the sundresses and stepped into it. Pulling it up I
knew I would need a little help with the zipper. First, I dug into my
suitcase and pulled out the heels I had kept hidden and put them on my
feet.
I pulled the curtain back and Sarah was sitting in a chair at the table
with her back to my texting on the phone. She looked back over her
shoulder and when she saw me her eyes widened, and her eyebrows raised.
"Wow, is that new? Wait dumb question. Wow, that looks fantastic."
"Thanks. Can you help with the zipper?" I walked towards her.
"New heels also I see. Couldn't make the week without wearing heels,
huh?"
"No, plus I think this dress required them." I grinned.
"You may be right." She said flatly.
The dress was a fit and flare dress with cap sleeves. It was a teal
color and had a pattern made of squares formed by forks, with sea shells
in the middle that matched the color of the purple surplice bust, the
hem flared at the bottom with a gold embroidered Flounder on it. Aerial
signature was embroidered on the back shoulder. My shoes matched the
purple of the bust.
"Maybe you should have had had the Little Mermaid nails done instead of
me," Sarah said. Her tone maybe a touch harsh.
"Are you mad about it?" I asked.
"No, it is okay. Why did you hide the dress and not tell me though?"
"I don't know. I think I was worried you would think it was, I don't
know, too much or something?" I was looking down as I spoke.
"Well, it is a little more than I expected. And probably more than most
women would wear."
"Most, not all. And I know I tell you this, but you have had all your
life to wear pretty, or cute, or girly stuff, or even sexy things. I am
trying to make up for lost time." I tried to say this without emotion
in my voice.
"Fair enough. Just so know, this is going to attract a lot of
attention. But at least you are going to look good while doing it." She
smiled.
"Um speaking of attention, I am going to get a Minnie Van. I don't want
to wear this on the bus, Okay?" I told her as I loaded my purse.
We stepped out the door and Pat and Jordie were waiting for us. Pat
looked cute in her sundress and I noticed again that she had choose one
that showed her ample cleavage. I was glad she was seeming more
comfortable with not wearing things that tend to just cover her up.
Jordie looked great in her body con dress. It definitely fit her curves
perfectly. I checked and she was wearing her wedge heels which made her
legs look great.
Both of their eyes widened when they saw me. Jordie added a big smile.
Pat's expression was more neutral. It made me think maybe I had
overdone it with the dress.
"Wow, that dress is awesome," Jordie said. "And those shoes are perfect
with it."
"Thanks, I am beginning to think is too much, maybe? Should I change to
a sundress?" I replied.
Sarah jumped in. "Do you want to wear a sundress?"
"Well, no, not really."
"Then don't. You look fucking amazing. Own it," Sarah said with
authority.
Pat and Sarah started walking and Jordie and I fell in behind them.
Jordie reached over took my hand for a second and squeezed it giving me
a smile at the same time. We did get a lot of second and even third
looks as we walked out through the lobby to me our Minnie Van driver.
The driver, a woman in her late thirties told me she loved my dress. We
told her we were going to the Yacht Club.
"Have you all ever stayed at this resort?" Pat asked on the drive.
"No, it is top of my list for a future stay though," I told her.
While the lobby of the resort wasn't a big as some of the other deluxe
resorts it was impressive. There was also a different feel to it, like
you were in an upscale place. Again, I got lots of looks as we made our
way through it. Most of them were appreciative, even from the women. I
loved hearing my heels as I walked across the wood floors.
We arrived at the Ale and Compass Bar, we had about thirty minutes until
our reservation. Sarah saw a group of seats at a high-top table, we sat
and each ordered a glass of wine. Running my hand under my dress as a I
sat, seeing the hem of my dress on the top of my thigh, my crossed legs,
the heels I was wearing, my nails as I held the glass, along with my
lipstick prints on it, I loved how all that made me feel right at that
moment.
Sarah must have noticed it also, her fingers touched my arm. "You love
this don't you? Being dressed up and out as a woman."
"Yes, is it obvious?" I raised an eyebrow.
"Very much."
Pat interjected. "This sort of reminds me of being on the cruise ship
and having a drink in pub before dinner."
"You are right mom, it does. It is weird because I almost don't feel
like we are at Disney World right now." Jordie said.
"Sarah and I do a lot of stuff that isn't park related when we are here.
We go to different restaurants, we have gone horse back riding, done
night time safaris, bar and lounged hopped to different resorts. The
parks are just a part of our visits."
After our drinks we walked the short distance to the restaurant. The
Yachtsmen is billed as a steakhouse and the steaks are very good. Brad
would have ordered a New York Strip, but Brandi thought that a petite
fillet was more appropriate. Sarah had the same and we split a salad.
Pat ordered a chicken dish and Jordie scallops. I think they were
reluctant to order steaks due to the price since we were paying for the
meal.
After dinner was over Sarah stopped me right after we exited the
restaurant, Pat and Jordie had wondered ahead. She asked if I wanted to
go over to the Animal Kingdom Lodge and have a drink at the bar there.
They have a drink I like a lot and she thought Pat and Jordie would
enjoy seeing the huge lobby there.
"Um, I kind of have plans this evening," I said unable to look at her as
I said it.
"Really? What plans? Why haven't you said anything?"
"Matt wanted to meet for a drink," I responded looking at her shoes.
"Really? And you didn't think you should tell me about that?" Her tone
wasn't angry, but it wasn't friendly either.
"I was, I don't know, maybe embarrassed to tell you. Scared of what you
would think, I guess." I was looking at her now.
"Why? Are you scared I will realize you are interested in men? Pretty
sure I am in on that secret now." I think she was trying to be funny,
but it sounded more accusatory.
"No, because of Steve." I was looking down again.
"Oh, you are worried I would be mad you are cheating on the man you are
marrying on Sunday. That I would think you really are a slut, not just
someone who gets a little turned on by being called one." She snickered
at that.
I was surprised at the second part of that. I don't know if I had ever
told her that about how I reacted to being called a slut. I thought the
only one I had ever told that was Steve. She saw my face and knew what
I was thinking.
"Yes, I know that. Steve talks to Lisa, Lisa and I talk." Now her tone
was defensive. "So is this just a drink or do you plan to hook up with
Matt tonight."
"Just a drink." I then hesitantly added, "I think."
"Okay, well let's get you back, slut." She did laugh as she said that.
I again loved the sound of my heels as I walked through the lobby of the
hotel. I also loved the feel of the hem of my dress as it hit my
thighs. I caught a glimpse of myself in a mirror as I walked and loved
how the dress and heels looked together. I also saw a few admiring
looks from both men and women.
I had a brief thought that I couldn't understand why Sarah and Pat
wouldn't want this? Was it because they had already experienced it?
They had the experience when they were young, when being beautiful was
easy. I remembered Sarah wearing short skirts when were dating and how
great her legs looked. Maybe they didn't want the attention?
I suddenly wanted to ask Sarah about it but wasn't sure how to do that.
Would she think I was criticizing her clothing choices now? Or think I
was saying that she wasn't attractive anymore? I looked at her and
realized that her sundress actually did look cute, it landed just above
her knees. Her legs looked good and her painted toenails showing in
her sandals looked great.
She saw me looking at her. "What?"
"You look good tonight." I smiled. "You really are beautiful."
"Okay, glad you noticed. Thank you." Her tone and face had no emotion
as she spoke.
I suddenly wanted to have physical contact with her, to hold her hand or
put my arm around her but I knew she would not react to that well. I
suddenly got sad at that thought because I also knew that even if I was
wearing a polo shirt and khaki, and not a dress and heels, she wouldn't
react well to me touching her.
My face must have shown something because just after we stepped outside
to wait for our Minnie Van she directed me away from Pat and Jordie.
"I don't know what the compliments or how you were looking at me was
about or what is going on. I don't know what you expect from me or how
you want me to react. You are wearing a dress, heels, makeup, all of
it. You are getting ready to go have drinks with a man. In two days,
you are going to put a wedding dress on and marry a different man."
I didn't say anything mostly because I didn't know what to say.
Everything she had said was true.
"So, you suddenly tell me I am beautiful, and you look at me with puppy
dog eyes. I am flattered okay, but that doesn't change everything that
is happening with you. I keep telling you this, you need to do these
things and figure out what it is your really want or need."
She turned and walked over the Pat and Jordie just as our Minnie Van
arrived. The driver got out and began to open the doors. She was a
middle-aged woman who was smiling as she got out of the car.
"Good evening Princesses! You all look fantastic." She turned to me.
"Oh, my that dress is amazing."
I saw Sarah smiling as I thanked her. She confirmed we were going to
Port Orleans French Quarter as we got into her car. I pulled my phone
out and sent Matt a text saying I was heading back now. It seemed like
forever but was probably only two or three minutes when my phone
vibrated and saw his response saying he would meet me in the lobby.
We pulled up in front of the building and got out of the car. I wasn't
sure if Matt could see us, but I made sure that I was a graceful as I
could be as I swung my legs out together and exited the car. Sarah came
out after me and lightly grabbed my elbow and pulled me to the rear of
the car.
"First, you should let us go ahead of you. You will make a much better
entrance for him if you walk in alone. You look really fantastic in
that dress and you want him to just see you." She smiled.
Before I could respond she continued. "I also want you to remember that
you have big plans the next two days. Things you have dreamed of
experiencing I am sure. I can tell you like this new guy, the timing
kind of sucks honestly but don't mess up the weekend."
I wasn't sure what to say to any of that, so I just said. "Thanks
Sarah. You know, you look really do look great tonight also."
"Again, nice of you to notice. You know this isn't the first time I
have dressed up in the last couple years."
She gave me a big smile and a quick hug before turning and walking into
the lobby with Pat and Jordie. I stood by myself for a minute. I
watched some women give my dress a double take and a smile as the walked
by.
Once I was sure that Sarah, Pat and Jordie had cleared the lobby I
walked in, listening to my heels strike the tile floor. Matt was
sitting on a bench and as soon as I stepped in, he had stood up and took
a step towards me. He was wearing a polo shirt and khaki shorts. I
loved the smile that I saw on his face.
"Wow, you look amazing. And I thought you looked hot as Tinkerbell."
"Thank you. You look nice also," I responded trying to hold his eyes.
"So, we can get a drink here, or at the bar at the pool, or go over to
Port Orleans Riverside to the bar there, they should have some live
entertainment if you want to see that?" He was a little nervous which I
found cute.
"How about we stay here. I will let you in on a secret, these shoes
look great with this dress, but I am much happier when I am sitting
instead of walking in them." I laughed.
"Okay, sounds great," he replied.
He placed his hand in the small of my back and we walked the short
distance to the Scat Club that was off the lobby. There was a half
dozen tables spread throughout it and a couple of booth on each end.
About half the tables and booths were taken, almost all of them with
couples about our age. I was obviously the most dressed up person in
the room and received admiring glances from both the men and women.
Matt picked a table away from most of the other visitors. I told him I
needed to run off to the little girl's room. After quickly peeing, I
took a couple extra minutes freshening up my makeup, specifically my
mascara and lipstick. When I walked back to the table pretty much all
the eyes in the place were on me including Matt's and I loved the look
in his eyes.
"There is no waitress so I will have to get our drinks at the bar. What
would you like?" he asked.
"A red wine, whatever is convenient, I am easy."
I had added the last part on purpose and looked right at him as I said
it. His eyes had widened, and he blushed. I could tell he was trying
to think of a witty reply but only managed an okay. He moved easily but
confidently to the bar. I realized that I enjoyed watching him. He
returned a couple minutes later with my wine and a beer for himself.
"So, how was dinner? Where did you all go again?" he asked.
"The Yachtsman it is over at the Yacht and Beach Club Resort. In my
opinion it is the best meal at Disney, although I have never eaten at
Victoria and Alberts." Victoria and Alberts is more of any experience
than just a meal, formal dining, multiple courses, very expensive.
"Sounds nice, we ate here, the kids wanted one last evening in the pool.
It is funny they love the parks, but I swear they would be just as happy
to spend all day in the pool." He laughed.
"Yes, my kids were the same way. I am sure they are sacked out now.
Who is watching them?" I asked.
"They are sleeping in my sister's room tonight."
He looked right at me as he said that, and I think he raised an eyebrow
as he said it. I suddenly felt some butterflies in my stomach. I
sensed if I wanted to, I could be alone with him tonight and I was
pretty sure I wanted to.
"Nice, seems like your sister is a good aunt. You are lucky."
He went on to tell me about how great she had been, after he and his
wife had split up, with helping him with the kids. Especially stepping
up to babysit when he had the kids, but he needed to work. I asked what
he did for a living and told he was police officer, actually a detective
now.
I was a little surprised by that, I am not sure why. I have known a lot
of police officers in my life and he didn't really give off the vibe,
plus honestly, I was surprised that a police officer would be interested
in a crossdresser or trans person.
"How about you? What do you do for a living?" he asked.
"I am retired now, although I work part time doing safety and OSHA
stuff. Before that I was firefighter."
We both laughed at that. There is a very friendly rivalry between
firefighters and police officers and the irony of that kind of hung
there.
"How long were you on the job and how long have you been retired?"
"Trying to figure out how old I am?" I smiled. "I worked for thirty
years, I started young, and I have been retired for just over a year. I
am close to celebrating my fifty-first birthday."
He eyes widened as I mentioned my age, but he was still smiling.
"Yea, makeup does wonders. Probably takes ten years off. How old did
you guess I was? How long have you been a cop? And how long until you
retire?"
He laughed. "Honestly, I was thinking early forties, forty-five at the
oldest. I have one more year to twenty-five when I will be eligible to
retire, not sure if I am going to. Since you are trying to figure out
how old I am, I am forty-five. How old did you think I was?"
"Early forties tops. You definitely keep yourself in great shape." I
had leaned forward as I said that and moved my wine glass towards him,
that was now close to empty, letting him see the lipstick stain on it
and my nails wrapped around the glass.
"Thanks. Do you need a refill?" He nodded towards me glass.
"Maybe, it depends, are you trying to get me drunk to take advantage of
me?" I wanted it to sound like a flirty joke but wasn't sure it had
come out that way.
"Definitely not," he responded immediately.
"Oh, sorry then. In that case no to another drink. Thanks for the
drink. I hope you have a safe trip home. Where is home anyways?" I
was hoping my face wasn't giving away the complete embarrassment I felt.
How had I read this so wrong? I was getting ready to stand up to go.
"Wait. He put his hand on my arm. I think that came out wrong, sorry.
What I meant is I wouldn't get anyone drunk and take advantage of them.
Let's have another one okay because I want to keep talking."
He got up and went to the bar and got another glass of wine for me and
another beer for him.
As he sat my wine glass down on the table he said, "Home is Richmond,
Virginia or at least the outskirts of it. I work in Richmond. Where is
home for you?"
He must have seen my eyes widen. "Really? Virginia is home for me also
but Northern Virginia, just outside of DC. We are almost neighbors."
"And that is where you worked also?"
"Yep. Actually, I live like about 35 miles south of where I worked. We
probably on live sixty to seven miles or so away from each other, small
world."
I took a sip of my wine and there was silence at the table. I was trying
to figure out what exactly was the deal was with Matt's interest in me.
Was it the novelty, or maybe he was gay, or a tranny chaser? There was
an obvious silence hanging over the table that I finally broke.
"So, what is going on here? Why are you having drinks with me and
flirting with me? Don't get me wrong I enjoy it, but you can't lack for
female attention, so why me? Especially since you know the truth about
me." I had emphasized the word truth. The second glass of wine had
reduced my inhibitions. "Are you... bi-curious, gay, a tranny chaser?"
"Honestly, you fascinate me. I know what is underneath all of that, but
I really like what I see on the outside. You truly have a great ass and
legs. You are pretty, you are fun, you are a really good flirt."
I blushed. "Thank you. That was sweet. So, have you ever been with
someone like me?"
"Been? Oh, you mean have I ever had sex with a...." He stopped
suddenly.
"A man, or a man in dress, crossdresser, tranny, or a transgender woman,
whatever you want to label me." Again, the wine was making me bolder
than I normally would be.
"No." He paused. "What would you label yourself as and why do you keep
using the word tranny? That is pretty self-demeaning isn't it?"
Up to that moment I have would have said crossdresser, but I suddenly
wondered if maybe I was actually a transgender woman? And he was right
about using the word tranny, it was kind of demeaning. I don't know why
I kept using it. I really did not want Matt to think of me as a man in
a dress that was for sure.
I decided to be honest. "Up until you asked me a second ago, I would
have said I was crossdresser. Right now, I am wondering if I maybe I am
something more. As far as the word tranny, I have no idea. I am just
having a hard time wondering why a very attractive, intelligent, nice
man would be interested in me."
"Why, what about the guy that made the fake proposal to you? Did you
wonder that with him?"
"No, because I knew what he was interested in and his wife gave him
permission to do them with me, and because I was curious about those
things, it just seemed like it was a good, I don't know, fit." My
second glass of wine was finished now but I was starting to loss some of
my courage.
Matt smiled. "You don't think I like those things also?"
I looked up at him. "So that is why you are here, you want a blow job
or to fuck me in the ass?"
"Woah, slow down. I am here because I like talking with you and
flirting with you. Am I interested in you sexually, yes, but I have
never been with a man or someone like you and I am not chasing you
because of that!"
All of my thoughts and emotions were overwhelmed right now, and I was
torn between running away or running to his room. This felt so
different than Steve, who I suddenly realized I had not heard from since
yesterday. I definitely appreciated all the experiences he was letting
my have but it was obvious, Steve's interest in me was for sex. The
other things were just what he had to do get that sex.
And what about Sarah. How did she fit into this? It was very obvious
that our sexual relationship was over, she made that clear, so why was I
suddenly looking at her and admiring how she looked. Hell, I got turned
on seeing her naked the other day. What would she say, or think, if I
slept with Matt tonight? Did I want to sleep with him? The simple
answer to that was yes.
"Are you okay? You are suddenly very quiet," Matt said. "I didn't
upset you did I. I am sorry if I did. I sometimes, I guess you would
call it, think out loud."
I giggled. I knew exactly what he meant because I did the same thing.
"Matt, you are wonderful. I would really like to get to know you better
but..."
"But what?" he interrupted.
"But I think I have to call it a night. There is just too much going on
in my mind right now". I feel like I am going to regret this in the
morning just so you know." I tried to force a laugh.
"I think I understand. I can't say I am not disappointed though." He
smiled.
We both stood up and I was getting ready to lean in for hug and say good
bye.
"Let me walk you back to your room, okay?"
"Of course, I would like that, a lot. Although that won't let you watch
my ass as I walk away." I was trying to be flirty, but I felt
butterflies in my stomach. "What time is your flight tomorrow? You all
did fly right?"
"Yes, it is at four o'clock. My sister is taking the kids to breakfast
at the Grand Floridian at eight. I guess Mary Poppins and some other
characters are there? Then we are planning to hang out at the pool
until the Magic Express picks us up at 1:00."
"Oh, they are going to Park Faire. We are eating there on Sunday
morning. Why aren't you going? It is very good!" I asked.
"Police officer salary, Disney is expensive in case you haven't
noticed?" He laughed. "Seriously, I am not much of a breakfast person,
my sister loves the kids and likes time with them without me there, and
I can save a few dollars."
"Your sister sounds awesome, even if she was betting on what was
actually in my panties." I laughed.
"She is. And as I said, he has been a tremendous help since my wife
left me."
I was disappointed the walk was over, but we were at my door now. "This
is my room. I have no idea why anyone would leave you."
"Oh, I have my faults, trust me. I just try not so show them in front
of women I am trying to impress." He looked right at me and smiled.
When he said women I am trying to impress, I almost melted. I looked
into his eyes and then leaned forward and kissed him. It was gentle
kiss but there was a promise of more to it.
"Thank you for the drinks and for being so... just wonderful," I said.
"You are welcome. Can I text you later next week, just to see how the
rest of your trip went and... stuff?"
"I like the, and stuff part of that, definitely. I will be looking
forward to it." I pulled him into a hug and a quick kiss on the cheek
before using my Magic Band to open my door. "Good night Matt."
"Good night Brandi."
I saw him moving away as the door closed. Sarah was sitting in the
middle of her bed reading her Kindle.
"Well, how was your date? You are back sooner than I expected. Oh, did
you need some place to go? I could hang out in Pat and Jordie's room
for a while," she said.
Her tone sounded sincere. I was a little surprised at the last part of
that. "It was nice, really nice. Um... and no, his room is empty, his
kids are with his sister."
"So why aren't you all there right now?" She raised an eyebrow.
"I don't completely know. It just didn't seem like that was the right
thing to do I guess." I had reached down and removed my heels.
"Why not. It is obvious you like this guy. Didn't want to be a first
date slut?" She laughed as she said it.
"Maybe, a small part of it. Can you help me with the zipper?" I backed
up to her bed and sat on the edge. "Weren't you telling me an hour ago
to not mess up Sunday?"
She pulled the zipper down. "What Steve doesn't know won't hurt him,
right?"
I was surprised to hear her say that. I felt the bed vibrate a little
and Sarah quickly reached for her phone. She picked it up and obviously
read a text message as a big smile came across her face. She protected
the phone from my view as she sent a quick reply, her smile getting
bigger.
"How about you? Would you knowing hurt?" I asked looking right at her.
"What do you mean? Would it hurt me that you were with someone else?
We have talked about this. I don't care what you do with men when you
are being Brandi."
The bed vibrated again, again she picked up her phone and smiled at what
she read while deliberately making sure I couldn't see what was on the
phone. When I turned towards her I noticed she was wearing a sleeveless
t shirt with out a bra, and the angle I was at allowed me to pretty much
see all of her breasts. It was obvious her nipples were harder than
normal.
"Why don't you care? And what if I stopped being Brandi?"
She looked up at me, catching where my eyes were focused and quickly
changed her position so I couldn't see down her shirt anymore. She gave
me an almost dirty look and typed another quick response.
"First off, don't fool yourself. You aren't going to stop being Brandi.
If anything, you are going to be Brandi more and more. And second, I
have told you before, you need to do these things to figure out what it
is you really want." She was still holding onto the phone when it
vibrated once again.
"Who is texting you?" I asked.
"Why are you asking?" she replied forcefully.
"Because I want to know."
"Why do you want to know? You just got back from a date and you are
worried about what I am doing?" She smirked as she typed a quick message
on her phone and apparently hit send.
"So, you aren't going to tell me?" I ignored the part about me being on
a date.
"I actually texting two people. Pat and Eric. Okay."
"Why are you texting Eric?" I quickly replied.
"Because he texted me." She smiled at me.
"But what are you texting about?" I had some panic in my voice.
"Oh, I won't tell you that exactly, but I will say it is nice to have
someone paying attention to me and do some flirting with me. I am sure
you know exactly what I mean." She got up and moved towards the
bathroom. "You need to remove your makeup and change for bed."
The bathroom door closed. I removed my dress and hung it up and started
to remove my makeup. Sarah exited the bathroom, and in the mirror, I
saw her send a couple of messages before setting her phone down and
climbing under the covers in her bed.
I stepped in the bathroom and sat to pee. I was still in my bra and
panties. I had worn a really cute lavender thong with lots of lace. I
had chosen it because of my date with Matt and thought he might have
seen me in it. I wondered if I had a made a mistake in not going back
to his room tonight, especially with how Sarah was acting. I stepped
out of the bathroom and quickly brushed my teeth then went and grabbed
my PJs.
"That is a cute pair of panties. It is a shame Matt didn't get to see
it. You look pretty hot in it," I heard Sarah say.
I didn't respond and climbed into bed, I Iaid down and closed my eyes,
and I thought about Matt, and Steve, and Sarah. As I started to fall
asleep, I was thinking I was in the wrong hotel room tonight and I was
marrying the wrong man on Sunday.