Finally a Princess (Part 4)
Part 4 of a Disney loving crossdresser who has come out to his wife on a
Disney Cruise. With a lot of help, and some Pixie Dust, dreams do come
true.
For the third morning in a row I woke up and saw just a little light
streaming into our stateroom. My wife Sarah was sleeping on the bed and
I could hear her lightly snoring. One of the reasons we rarely slept in
the same bed. I was on the couch that converted into a bed.
As I had the past two mornings, I spent a few minutes reflecting on the
day before and everything that happened. I had spent another day as
woman. This included time on Disney's Castaway Cay in a woman's bathing
suit, and the night wearing a favorite lace dress and heels. My wife
was supporting this and I was getting plenty of help from our friend Pat
and her adult daughter Jordie, who were on the cruise with us.
I also woke up feeling very nervous. I had a date this morning, with a
man, and a man that I was finding myself more attracted to when I spent
time with him. Last night we had danced together and he had pulled me
close to him and I felt like I was on fire. For some reason, at least
so far, Sarah was supporting this also.
I got up and headed to the bathroom to pee. Looking in the mirror I
knew that I would have to shave. I also decided that I needed to shave
my legs and underarms again so I hopped in the shower and again loved
the feeling of running a razor over my legs. Sarah had told me that if
I had to do this all the time I wouldn't enjoy it as much, but right now
every feminine thing I did gave me a feeling of joy.
I quietly left the shower and moved across the room, being careful not
to wake Sarah. I grabbed a pair of my purple lace edged bikini panties,
now that I had my full collection of panties available, I could save the
thongs for when the outfit called for them, or I needed them to keep
things tightly controlled. I also put on the bra that matched and
slipped my breast forms in the cups. I pulled on a borrowed pair of
shorts and my new Castaway Cay woman's pale lavender shirt. My new pink
hat completed my outfit and I headed out the door.
It felt good to know I was wearing mostly my own stuff, especially my
own, panties and bra. Sarah, with the help of Pat and Jordie, had packed
a lot of my girls stuff that had been hidden at our home. After
discovering I was crossdresser, by coming across open web pages on my
Ipad, she had found my stash of stuff. With Pat's help she had set up a
scenario where I had been forced to borrow women's clothes for two days
because my luggage was lost. After I confessed I was a crossdresser,
she confessed to knowing and the plan that she and Pat had hatched.
I made my way up to the top deck and grabbed a cup of coffee before
heading to the bow to watch us approach the Port of Nassau. Again there
was a large number of people along the rail doing the same thing I was.
The sun was now brightly shining and, as I felt it on my skin, it was
giving me energy along with the coffee I sipped.
"Good Morning Girl Friend." The loud voice behind me belonged to Susan,
the wife of the man I had a date with later this morning.
"Good Morning Susan." I had moved closer to her to greet her because I
knew the one thing that definitely gave me away, was my voice. "How are
you this morning?"
"I am great. It is beautiful out. The bigger question is how are you
this morning? Big night last night, how are your feet and calves doing?
All that dancing in your heels must have made them sore." She grinned
and winked at me. The wink, I think, was because of the slow dance I
had done with her husband Steve.
"Actually, they are fine. If they were sore it would have been worth it
though. Last night was honestly like a dream."
"I am happy for you. It is wonderful that you are getting to experience
all this. You should know that I had to hold Steve off last night. I
think that dance with you had him ready to burst. Are you looking
forward to your date?"
"I am. I have to ask again, are you sure you are okay with this? I
also have to be honest with you. If I get the chance to be intimate
with Steve I am pretty positive I am going to take it."
"Intimate. That is sweet. You mean if you get a chance to suck him off
or get plowed by his dick don't you?" She must have seen my eyes grow
wide. "Relax, I am half teasing. I learned a long time that when it
comes to talking about sex, it is better to be frank about it. When we
use euphemisms or hints we tend to cause confusion or not get what we
want."
"Okay, yes that is what I meant. Especially the sucking him off part.
I have really wanted to the experience doing that and this seems like
the prefect opportunity."
"Again, yuck but more power to you girls who enjoy that. So you aren't
as positive about the being fucked in the ass part? Because I can
assure you Steve wants your ass."
"I am more scared of that honestly. Umm... I am not a total virgin
there. I have had dildos and vibrators in my butt before, what I am
scared of is not being in control of it."
Susan smiled. "Understandable, I have tried it. I hated it. It is
why I let, and even encourage, Steve to find others for that, I have
heard that having a prostrate can make it feel a lot better. My advice
to you is lots of lube."
We both laughed as she said that. We were entering the small opening of
the port now, something that amazed me that could be done with these
huge cruise ships.
"I struck out with your wife last night. I also understand that Nancy
and Melissa struck out with Jordie. I guess we will have to look
outside the group for a little fun."
"What about Pat? I told you, if I was going to pick one of the three of
them who would be willing to let you lick their pussy, it would be her.
No, idea if she would return that favor but, I bet, given the right
circumstances she would let you go down on her."
"Okay, maybe I will cozy up to her while we shop today. I am off to
shower and get dressed. I enjoy our morning chats."
"I enjoy them also. I am already looking forward to seeing you here
tomorrow morning." That was a true statement.
I decided to head back because I wanted have as much time to get ready
as possible. I realized that I still needed to pick out something to
wear today. None of the women's clothes I owned before this trip would
be appropriate for a visit to the museum or Margaritaville. I guess I
could wear what I had on but I was hoping for something that was more
girly than this.
Sarah was just waking up when I got back to the room. She is definitely
not a morning person so I always tried to be careful about being to
cheery first thing. I made my way to the other side of the room and sat
down so she could keep waking on her schedule.
"Hey, good morning. How did you sleep? Did you watch us pull into
port? See anything interesting? Have you showered yet?"
I guess she decided she was awake. "Good morning, I slept well
actually. I did watch us pull in, still amazing to watch that. I have
showered and the only interesting thing I saw was Lisa."
"How was Lisa this morning?"
"She was fine. She was disappointed she struck out with you." I
laughed a little as I said that.
"Did she actually tell you that? She literally has no filter does she."
"She did actually tell me that."
"Did she say anything about Steve? Is your date still on?"
"She told me he is raring to go. And the date is still on as far as I
know."
There was a bit of an awkward silence for a minute before Sarah
responded. "And how about you? Are you still excited about it?"
"Truthfully?"
"Yes, I have told you I want the truth with all of this."
"Yes, I feel like I am in high school. I can't wait to spend time with
him."
"Well okay GIRL, let's get you ready then."
I saw her typing on her phone and I assumed she was sending a message to
Pat. I am not sure why but I suddenly realized how strange this was.
My wife was working on getting me ready, to make sure that I looked
girly and attractive for a date with a married man, whose wife was
encouraging this. I heard her phone vibrate and she smiled when she
read the message.
"Pat and Jordie are all set to get you ready. We had picked out an
outfit for you that I thought you would like for our at sea day but I
wasn't ready to spill the beans that day. Besides, the weather that
morning wasn't really that great and this is more of a sunny day outfit.
The best part is it will be perfect for today."
We got up and headed to Pat and Jordie's room. After exchanging good
mornings and lots of smiles Pat told me that she was just going to fluff
my hair some, then Jordie would do my makeup. Sarah again told me I
need to watch what she was doing so I could start doing it on my own.
Once again I was amazed at her work. She seemed to go light on the eye
shadow but heavier on the eye liner and mascara. The result is my green
eyes really seemed to stand out. She had also done my lipstick in a
deep red color.
"We need her nails to match the lipstick, plus honestly red nails look
really hot on a hand wrapped around a penis." As Pat said that both
Sarah and I burst out laughing. "What, they do. Plus they will match
her outfit." Pat grabbed my hand and started her work.
"Ready to see the outfit?" Sarah asked when she had finished.
I just nodded and Pat went over to the wardrobe and pulled out two
hangers. On one of them was a red with white polka dots skirt. The
other had a black short sleeved shirt on it. This was definitely an
Minnie inspired outfit. I was smiling but it looked like the skirt was
pretty short and the shirt was small.
"Oh wait, what color are your undies?" Jordie asked that.
"Umm, purple, why does that matter?"
All three girls laughed and Pat said, "Because I am pretty sure this
outfit is meant to be worn with either black or red undergarments.
AND... if a girl thinks she is going to have sex she wants to make sure
she has the right underwear on."
I was beat red but Sarah had moved to the door and left the room. She
was back shortly with a red bra and red bikini pants. I took them from
her and started to move to the bathroom to change. Sarah told me to
just change into the bra and panties and to step back out. I started
to protest but remembered Pat's comments about if we were all going to
be girls on this trip we needed to be comfortable in towels, nighties
and undies in front of each other.
When I came out I was nervous but Jordie broke the ice. "If I was
Steve, or I liked girls, I would jump all over that." Her smile lit up
the room.
Sarah handed me the shirt first. I pulled it on and realized it was
tight across the chest and maybe was a little short. I moved to the
mirror and noticed if you looked really close you could see the out line
of my bra straps and a little bit of the contour of lace on the cups of
the bra.
"Yea, we had a different bra in mind with this outfit when we picked
out. As Pat said yesterday I think, no one had you, at the top of the
most likely to get some dick pool at the start of the trip. But, I
think this is perfect for your date." I still couldn't tell if Sarah
was being angry, sarcastic, or trying to be funny.
I stepped into the skirt and pulled it up. There was a small zipper on
the side and once that was pulled into place the skirt fit perfectly.
The waist was a little higher than what I was use to but now I realized
why the shirt was a little shorter. The skirt was a skater style that
flared out but stopped about mid-thigh, I was going to be showing a lot
of leg.
When I looked in the mirror I knew I was to old to be wearing this
outfit, I also knew that I was going to wear it. I loved it. The make
up with it was perfect. While it was obvious I wasn't a twenty
something year old girl, Jordie's makeup could only do so much magic, I
was definitely a girl. I also decided that before being asked, or maybe
because I wanted to feel a little control, to do a quick twirl in the
mirror.
"Yea, you will need to be careful doing that in public or everyone is
going to see your pantie," Pat said.
"Oh My God. Do that for Steve one time and he will be begging to put
his cock in your ass." Again Sarah's tone and facial expression didn't
completely match.
I ignored her, instead I asked, "What about shoes? I don't think my
flip flops will go with this? Sarah can I borrow your white t strap
sandals?"
"Yep, she is definitely a girl now. Worried about making sure her shoes
match her outfit." Jordie was smiling and her tone was warm and
friendly.
"Yes. I will grab them and then we need to get to breakfast so you
won't be late."
The walk to the back of the ship interesting. My outfit got lots of
looks. There was about an equal combination of raised eyebrows,
appreciative smiles, and several men doing double takes to get a better
look at my legs. Once again I walked next to Jordie and I heard Sarah
telling Pat that skirt was doing a good job of teasing a great ass under
it.
I had a small breakfast. The table was kind of quiet this morning. A
few comments about the weather. Sarah told Pat and Jordie what to
expect as we got off the boat and would be accosted by Bahamians outside
the gate. We confirmed the plan to meet at the Margaritaville for a
drink.
Pat then picked up a banana. "Ready for your lesson?"
I turned red. "Here?" I wasn't sure if I meant in public or in front
of Sarah.
Sarah saw my quick glance at her. "Don't be embarrassed about it
because of me. It isn't like I don't know what you are planning on
doing."
Pat had peeled the banana and placed it in her mouth being able to get
about half of it easily in. She slowly slide it back out. Stopping and
she opened her mouth to show she was circling the top of the banana with
her tongue.
"That's all there is to it for the beginner lesson. Get as much as you
can in your mouth, use your tongue, watch out for your teeth, and act
like there is nothing in the world you would rather be doing than
sucking on his dick. We can work on deep throating and being throat
fucked later."
All three of us looked at her with shocked expression at the last two
comments.
"What?" She laughed.
"Are you planning on swallowing?" I was a little surprised that Jordie
asked the question.
Another quick glance at Sarah whose eyes showed she waiting for the
answer also. "Yes, I think."
"Gross, but you do you," Sarah said quickly.
"It is an acquired taste." Followed by her amazing laugh, Pat broke the
ice again.
I had been dying to tell someone this since dancing with Steve last
night. I started to say something to Sarah in our room before bed but
held back. I decided at this point it wouldn't matter.
"Last night when we were dancing. He pulled me tight against him and I
could feel it against me. It was hard and felt like it is pretty big.
I am a little nervous about that."
All three of the others laughed out loud at that.
Sarah jumped in. "Welcome to the club of having been grinded on. Of
course I am sure I speak for the three ofus, when I say that happened to
us the first time a really long time ago. Like a really time ago at
some of the first dances we went to in school." She had glanced at Pat
and Jordie who were nodding.
"I am sure you will be fine. If it is big and begins to hurt your mouth
or jaws. Remember the tongue right behind the head and some hand action
will go a long way," Pat interjected.
"Yes, and some ball licking and plenty of eye contact, especially with
the eye makeup I did today, and you will be done sooner." Everyone
giggled at Jordie's comments.
I wanted to go back to the room and freshen up just a little, plus I
needed to grab the back pack I had bought a couple nights ago. Jordie
was hoping to get a picture with Goofy so she was running off to do
that. Pat said she wanted to sit on the pool deck and drink some coffee
for a bit before heading into town.
"Let me walk you back, Pat and Jordie I will meet you in the lobby at
10:30," Sarah said as she stood up.
The walk back to the room was silent. I think reality was hitting us
both. I was dressed as girl, a very girly girl, getting ready to go on
date with a man. There was also a better than average chance that I
would have the opportunity to have sex, at least oral sex, with this
man.
In the room I brushed my teeth again, teased my hair some more, and
reapplied my lip stick. The last two things made me feel warm
throughout my body. I had to admit to myself that everything happening
right now made me happier than I had been in a while.
Sarah was sitting on the end of the bed when I stepped out. "Listen, I
want you to know that I am excited for you. I am happy all these things
you have dreamed about and fantasized about are coming true. I also
will want to hear every detail about it this afternoon. Please,
remember I love the person that is inside of all that feminine
clothing."
We both had tears in our eyes and I sat next to her and hugged her
again. It was ironic, we had shared more hugs in the last two days,
while I was dressed as a woman, than probably the last three years.
"Okay stop. If you start really crying you will mess up Jordie's makeup
work. You need to get going. Are you okay to walk there by yourself?"
I nodded yes. Scared to talk and that my voice would crack.
"Have a wonderful time. Every girl always remembers her first date.
And be sure to DO things I wouldn't do." She forced a laugh at the end
of her joke about me wanting to blow a guy and have a dick in my ass.
I laughed and said a quiet thank you as I pulled the rose gold sequined
back over my shoulders and headed to the door. I am not sure why but
the click of the stateroom door closing sounded like a slam to me.
On the walk to the elevator and the ride down to the lobby I felt like
my breathing was suddenly off. I was just now realizing how anxious and
excited I was. As I got out of the elevator a woman told me she loved
my outfit and my confidence. I mouthed a thank you because I wasn't
sure if she was saying that about an older woman wearing the outfit or
she knew I was actually a man.
I saw Steve in the lobby standing with Lisa. I was a little surprised
to see her there and wondered if something was going on. Steve also had
a red rose in his hand . I walked slowly up to them, Lisa saw me first
and she smiled widely as she recognized me. Steve following her eyes,
saw me next, and his eyes immediately went from my face, to my tight
shirt, to the short skirt. I then watched his eyes travel up and down
my legs.
Lisa stepped away from him and came to me for a hug. "You look
fantastic sweetie. Are you excited?"
I whispered yes into her ear. I broke away from the hug and stepped
towards Steve who was holding out the rose to me.
"Thank you." Again trying to speak softly. I hated my voice right this
minute.
"You look amazing." He was speaking to my chest and not my face as he
said it.
I decided to try and lighten the mood and leaned in and whispered.
"They are still fake. Tinkerbell didn't come in the middle of the
night, sprinkle pixie dust, and I suddenly grew boobs."
He laughed. "Sorry. If she could do that would you want her to? And I
will try and make sure I just stare at your legs and ass instead since I
know they are real."
I was suddenly flustered again and I looked down at the rose in my hand.
I was actually wondering about his question about suddenly growing
boobs. And I loved that I knew he was sincere in his compliment of my
ass and legs.
"Let me take your rose. They won't let you take it off the boat I am
sure. I promise to take care of it for you. You two have a great time
and Brandi make sure you DO the things I wouldn't do." Lisa gave me a
huge wink.
I laughed and said, "Sara told me the same thing."
I felt Steve hand in the small of my back and he guided me towards the
elevator we would need to take to get off the ship. He asked how my
morning went and told me he had heard that I had seen Lisa earlier. I
told him it was good and confirmed that running into her in the morning
was starting to be a regular thing and that I enjoyed it. I then
wondered if I was being stupid talking about his wife. So I quickly
changed the subject.
"So were you in the gym this morning?"
"Yes, I start most of my mornings there. I find if I don't do that
first thing the chances of it happening are way less."
"Well, I can tell you that your efforts in the gym definitely pay off."
I flashed him a big smile as I said it.
We reached the point where you disembark and Steve motioned for me to go
first. When I touched my Key to the World card on the scanner the
Disney Cast Member suddenly looked alarmed. He motioned for me to stop
and step off to the side. Another Cast Member quickly stepped up to him
and he pointed at the screen and then me. She nodded and asked me to
step over in a corner.
I immediately knew the problem. When we checked in at Port Canaveral I
had my picture taken with Sarah. I definitely did not look like Sarah
and I didn't look a lot like Brad.
"Uh... I know what the problem is. My appearance doesn't match my pic
right?" I had moved close to her and was speaking as quietly as I
could. "I am transgendered and came on the boat in my boy stuff but
since I have been on it I have been pretty much in girl mode."
"No problem. I understand. You look great. I love your outfit. I do
want you to be cautious though sometimes the local's don't take kindly
to members of the LBGTQ community.
Are you with him?" She pointed at Steve.
I nodded and smiled while looking at him.
"I am sure you will be fine then. Have a good time."
I moved through the line and Steve took my elbow in his hand and
steered me to and down the gang blank. He asked if everything was okay
and I gave him a quick review of what happened. I was fairly
embarrassed telling him. He sensed that and stopped and hugged me.
"Trust me. I see a woman when I look at you, there is no reason to be
embarrassed."
I was glad I had put on my sunglasses, or actually a spare pair of
Sarah's, so he couldn't see the tears building in my eyes. He asked me
what direction we needed to head and I found my hand in his as we ran
the gauntlet of vendors offering jet skiing, taxis, tours, etc.
The walk to the museum was about ten minutes and we didn't talk much.
The streets were noisy and I think we kind of needed to reset and get
back to date mode. Steve went to the desk and paid for us both even
though I protested and offered to pay.
We moved through the museum and discussed the different things we saw.
I explained that I found the age of piracy fascinating. I also said
that I understood that pirates were, basically , people that did
terrible things but I choose to like the more fictional, romanticized
version of pirates. Whether it was the book Treasure Island, or the
Pirates of the Caribbean movies.
He asked me if I had watched the show Black Sails and I immediately lit
up. "Yes, I loved it. I have actually watched it twice."
"So, which character do you identify with the most. Elanor, Max, Anne
Bonnie or Flynn?"
It was a really interesting question and honestly it made me a little
more attracted to him. Elanor and Max were definitely the most girly
characters. Elanor was bisexual who used men to advance her own
ambitions. Max was obviously a lesbian but as a prostitute slept with
men. Anne Bonnie, who was based on a real person, was heterosexual
female pirate but definitely a tom boy. Flynn, was the only male in the
group and was bisexual but eventually fell in love with another man.
"I think if I was picking who I would want to be it would be Elanor. If
I was picking who I would want to do, it would be Flynn." I gave him a
big smile with a blush as I said that. It was true. I had a big crush
on Flynn during the show, the guy was hot.
Steve smiled and took my hand in his as we moved through the rest of the
museum. My heart was once again racing and I started to think about
what would eventually happen today, or at least I hoped would happen.
Would he be bold enough to make the first move. How would we get to a
situation where we were alone and in private.
We got to the end of the tour and it emptied us into a gift shop. I saw
a clock and realized that we had about a hour to kill before we were
supposed to meet the others at the new Margaritaville. I figured it was
about a 15 minute walk. Steve glanced at his watch, I think was doing
the same math.
"Do you like Bloody Mary's?"
"I love them. Why?"
Steve asked the woman working the gift shop counter where we could get
the best Bloody Mary and she told us about a bar right around the
corner. It was on the second floor and had a deck that looked our over
the harbor and you could see the cruise ships. He thanked her and we
were on our way there.
We enjoyed our drinks and discussed our previous Disney's cruises.
There was a tension in the air and I sensed that he was thinking about
what was going to happen if we were alone. I got bold and made sure
that while not messing up my lipstick to much I left red marks on my
straw. I saw that Steve had noticed that. When I pulled the celery
stalk out of the glass and slowly sucked it into my mouth his eyed
widened.
"We probably need to head over to the Margaritaville so we can at least
make an appearance before heading back to the boat to go to the pool."
Steve nodded and waived the waitress over for the check. She
complemented me on my skirt and when he paid, as he counted out the cash
to pay, her she mouthed to me, he is hot. I nodded vigorously and we
both laughed. He gave her the cash which included a generous tip and
she thanked him and walked away.
As we walked out onto the sidewalk he asked, "What were two you to
laughing about back there?"
"It was a girl thing."
"Seriously, you can tell me."
"She mouthed; he is hot. I let her know that I totally agreeded with
her." I told him while grabbing onto his arm with both hands and
pulling myself against him.
The walk to the Margaritaville was about 10 minutes or so and again
because of all the road noise we didn't talk much. I was also a little
nervous that once we meet up with the group the date would be over and I
really wanted at least the opportunity to kiss him. Oh hell, I was
kidding myself, I wanted to at least suck his dick.
We stepped into the lobby of the bar area and of course the first person
we heard was Lisa yelling that they were all over here. We slowly made
our way there and got to the long table. They had saved us two stools
on the end next to Pat and Lisa, and across from Sarah and Jordie.
Nancy and Melissa were across from Lisa and Pat and Susan and Devon were
on the end.
There was a chorus of hellos and questions about the museum. We asked
how the market was and in the middle of it a waiter asked if we wanted
drinks. I saw that pretty much everyone but Devon had a margarita so I
ordered one also. Steve ordered a Landshark. We were told that we had
to catch up, that this was everyone's second drink, Steve informed them
that this was our second also. We had stopped for a Bloody Mary.
The waitress dropped two huge plates of nachos in front of us and
another brought our drinks. I noticed that Sarah was watching me and
Steve intently while Jordie was watching her mom and Lisa. I raised an
eye brow to Jordie and tilted my head towards Pat and Lisa and got a big
smile and wink in response.
Steve had leaned behind me and had a silent hand signal type
conversation with Lisa. Right after that he decided that we needed a
round of tequila shots and ordered them from the waitress. I heard Pat
tell Lisa that she would need to slow down or she would be making bad
decisions. Lisa replied to her, asking if they would be bad decisions
or fun decisions. Pat gave her amazing laugh as a response. After our
shots were brought to the table, and toasts to fun times and bad
decisions were made, we all downed them.
The Bloody Mary and Margarita had got to my head I think. I turned to
Steve and my hand ran up his thigh, over his shorts and let it come to a
rest cupping his dick, which was growing in my hand. I brought my lips
to his ear and said. "Sweetie, you don't need to get me drunk. I am a
sure thing if you get me alone."
His eye widened and he announced to the table. "Well I am ready to head
back and enjoy some quiet time at the pool while everyone is off the
boat. Anyone else heading back now?"
"I am ready," I said.
Sarah half said under her breath. "Yes, I saw that you were ready." I
realized she had seen or at least figured out what I had done with my
hand.
The far end of the table said they still wanted to do a little shopping.
That was followed by Sarah and Jordie saying the same thing. Pat and
Lisa were actually whispering between themselves while suddenly looking
like they were very friendly.
Steve and I stood up and he turned to Lisa, told her to pay for all this
when the bill came, we said our good byes saying we hoped to see
everyone at the pool. As we started to move to the door Sarah reached
out and grabbed his arm.
"Be good to her. Also a little advise, save some for later and you
might be able to get some pirate booty, I promise you won't be
disappointed."
I had no idea what the second part meant but I had a sudden hesitation
to race back to the ship because of her kind words about being good to
me. Steve had replied with a simple I will, placed his hand on my back
and led me to the door. When we got outside he saw a cab and grabbed
it. Telling me it would get us back sooner.
As the cab made the quick trip towards the ship, and it grew larger, I
grew more nervous. The brief bit of confidence that I had shown right
after the Tequila shot had rapidly disappeared. I looked at Steve out
of the corner of my eye and he caught me. His hand reached out and
landed on my thigh and gave it first a small squeeze and then slowly
starting circling his fingers on top of it.
We arrived at the port and as we started up the gang blank, I remembered
what had happened when we had disembarked, I hoped that I wouldn't run
into that problem again. I took the back pack off, set it on the
scanner belt, stepped through the metal detector, and tapped my Key to
the World card and went onto the ship. No problems.
When we got to the elevator I am pretty sure that my anxiety was
starting to show. I couldn't stand still and I definitely couldn't look
at Steve, especially in the eyes. Was this how our date ended? With
silence and awkwardness. Somehow I found the courage to speak.
"So, you are going to change and head to the pool now?" I stared at the
elevator door as I said it.
"I guess, what are you planning on doing?"
"Go to the pool also I guess." I turned to him and somehow managed a
smile and heard the elevator door ding signally it's arrival. The doors
opened and two families got out. Steve and I were the only ones that
got in.
"Would it be okay if I walked you back to your room to make sure you get
back safely?" he asked with a strange grin on his face.
"Of course. That would be nice." I meant that.
In what seemed like seconds, we were standing at my door and I touched
my card to unlock it, the click of the lock releasing sounded like a gun
shot. I grabbed the handle with one hand and pushed it down while
backing into the door. Steve stood there just looking at me. I am sure
he was wondering what had happened to his sure thing.
"Uh. Okay, See you at the pool," he said.
I reached out with my other hand and grabbed his forearm and pulled him
into the room. A smile spread across his face. We cleared the door as
it closed behind us. Hearing the door shut must have emboldened him
because suddenly I was pulled tight against him and his mouth was on
mine. Our tongues found each other and we kissed passionately as we
moved slowly deeper into the room. We made it past the bed and at some
point his back was now in front of the couch.
When his hands found my ass he pulled me tight against his groin and he
was obviously hard already. I rubbed and grinded against it and then
slowly broke the kiss and stepped back. My hands went to his belt and
after a slight fumbling, I released it and unbuttoned and unzipped his
shorts. The shorts and belt fell to his feet with a thud. I ran my hand
over this cock that was still covered by his boxer brief, while he
pulled me in again for more passionate kissing.
I broke the kiss and sank down to my knees. I had fantasized many times
about being in this position, the fact this was now, suddenly, caused
adrenaline to run through me. My mouth kissed his dick through his
shorts and I could hear him moan and felt his hands run through my hair.
I rocked back on my knees and looked up into his eyes and smiled. The
smile he returned to me made my insides melt and I slowly pulled the
band of his underwear away from his body and worked them down over his
cock.
I might have gasped as his dick sprang from the confines of his
underwear. I first saw a pronounced round head with a significant ridge
around it. Then I saw the delicious looking veins that stood out just
begging to have a tongue run over them. As I pulled his underwear past
his knees I got a good look at his large balls that were neatly shaven.
I also caught an amazing, musty, manly scent.
I pulled his briefs down to his shorts and helped him step out of them.
My mouth went to his balls and I gave each one a slow lick, then traced
my tongue up his dick before giving the head a quick kiss. Again, I
heard Steve moan and his breathing start to become faster. I stood up
and with one hand firmly wrapped around his cock I kissed him hard on
the mouth before using my other hand to push on his chest and force him
to sit on the couch.
Sinking back to my knees, I looked at my hand wrapped around his dick
and the first thing I noticed was my red nails and a quick glance up saw
that Steve was noticing this also. I also realized that my hand barely
made it around his shaft, he was fatter than I was. It was also very
obvious he was longer. At least seven inches but probably eight. His
dick was beautiful.
I moved my mouth down onto it and felt the ridge of the head on my
tongue. The taste of it was a bit salty and I loved it. I got as much
as I could in my mouth and took that moment to look up at Steve and into
his eyes. I heard "Oh God" from him. My hand wrapped back around the
shaft and began to bob up and down while circling my tongue over the
head and sucking. Steve had his hands in my hair and was stroking my
head. I noticed he was breathing faster and when my other hand went to
his balls I could feel them tightening.
I was just getting started and I wanted to savoir the taste of his
delicious dick so I backed off and ran my tongue over every vein I could
find, again making sure to look up into his eyes as I did it. I then
moved my mouth to his balls and licked and sucked on them. This got a
"Jesus Brandi!" response.
I moved back to take him in my mouth again and went back to bobbing and
sucking. I was loving this and knew I would be doing this again and
again. With one hand wrapped around the base of his shaft I started
jerking, with the other hand I started caressing his nuts. I heard
"Holly Fuck" and felt his balls tighten more and his shaft somehow get
even harder. I knew that he would be cuming soon.
"Oh Brandi, that feels amazing. I am going to cum soon."
I just looked into his eyes again and, while I am sure he couldn't tell
because my mouth was full of his dick, I smiled.
"Oh Fuck. I am going to cum." When he said that he removed his hands
from my head. I assumed this was to allow me to remove my mouth from
this dick so he wouldn't cum in my mouth.
I sucked harder and felt his dick began to pulse as he screamed, "I am
cuming! Jesus Brandi!"
The first shot of cum slammed against the roof of my mouth and he just
kept spurting more out. I was swallowing as fast as I could while
trying to taste it. There was so much, some of it some leaked past lips
and I felt it trickle onto my chin. He continued with small spurts.
Again, I looked up to meet his eyes and in his smile I saw content but
also something else, admiration, feelings, I wasn't sure. It made my
heart want to explode.
Once I was sure I couldn't suck out another drop. I leaned back and
looked at him while I used a finger to scoop the cum on my chin into my
mouth then leaned back down and licked up the little bit that was on his
dick.
"Well, that was yummy." Again looking right at him as I said it.
"Oh My God, that was amazing. Was that the first time you have done
that?"
I nodded as he motioned for me to sit next to him on the couch. As I
sat down, he wrapped his arm around me and gave me a quick kiss on the
lips. I wanted a deeper kiss but wasn't sure if he was reluctant to do
that since he had just cum in my mouth.
"Well you are natural cocksucker then. That was the best blow job I
have ever had."
Cocksucker. Wow. I guess that was true, I was now a cocksucker. I
smiled at him, not really sure what to say but finally went with. "I am
glad you liked it. I hope to be able to do it again."
He leaned down and kissed me again which made me feel good. I know that
lots of men, after orgasming all the sudden have guilt. I wasn't sure
if I was the first guy that had ever sucked him off but even if I was
dressed a girl, there was no denying I was guy. I stole a quick glimpse
at my at my crotch to see if my hard penis was evident, hoping it
wasn't.
"Uh. So Brandi, that was my first time with a guy. And even though I
know you looking nothing like a guy right now. I am not gay so..."
I immediately knew where he was going. "Relax Steve, I have no
expectation of you returning the favor. I wouldn't want you to, even if
you were interested. This is about you being a man, and a fucking hot
one at that, and me feeling like a woman."
I could see the relief on his face and he leaned in and kissed me
passionately again. When he broke the kiss he said. "And you are a hot
woman!"
I had snuggled in closer to him with my head resting on his chest area.
My one hand had fallen to his thigh and eventually onto his dick which I
was just softly rubbing my fingers over. One of his hands had pulled up
my skirt and was running over my panty clad ass.
"Will you tell Sarah about this?" he asked kind of out of nowhere.
"Yes, she told me she wanted to know every detail about my date."
"How will she take it?"
"I really don't know. She seems to encourage it one minute and the next
she says things that I am not sure if they are harsh jokes, or veiled
comments. I do know though without her help and support I would have
never experienced this."
I raised up and kissed him again, this one was somewhere between
passionate and tender, after the kiss I lowered my head to his lap.
This gave him better access to my ass which he was now fondling
aggressively. I took his soft penis in my mouth and almost nursed on
it. I felt it stiffen some and was a little hopeful that I might get
the chance to taste him again.
"That feels nice Brandi but I don't think he is going to be ready again
so soon. Unfortunately, it takes a little time to recover these days."
I sucked for about a minute more and then sat up and looked at him. "Do
you think he will be recovered by this evening. Remember Sarah
mentioned pirate booty later. I am hoping she was hinting at what your
hands were on a couple minutes ago."
He laughed. "I am pretty sure by this evening he will be ready to go
again." I saw him look at his watch. "Wow, we left them over a hour
ago. They will be back soon. Not sure I want them, and especially
Sarah, to catch me without my pants on."
It was my turn to laugh but I got off the couch and on my knees again
helping him put his feet into the boxer briefs. I kissed the tip of his
dick one more time before pulling the briefs over it. Next I assisted
with his shorts. I stood and kissed again. "Thank you for a day I will
never forget."
"No, thank you. Umm, you might want to work on that lipstick before
Sarah gets back also."
I turned and looked in the mirror. I laughed because the smearing of my
lipstick looked like I had spent the afternoon sucking dick. I walked
Steve to the door and told him I would see him later and gave him one
last quick kiss as he left.
Minutes later, right after cleaning up a little, which included peeing,
freshening up my makeup, and changing the panties that were drenched
with the precum I had leaked into them, I heard the door open and Sarah
step him. She stopped and looked at me, and for what seemed like
forever we just stared at each other. I felt a sheepish grin start to
form and her face followed.
"Well don't you look like the cat the swallowed the canary. And by
canary I mean cum."
We both broke out laughing.
"Details girlfriend! Yes it happened? No it didn't? Was it what you
dreamed about it? Did he treat you right? Hell, tell me about his
dick!"
So I took her step by step through it, from the awkwardness when we got
back, through the first kiss, all the way through him cuming in my
mouth, to the post orgasm time on the couch. I told her his dick was
pretty hot and she actually smiled at that. She asked if it was
anything like what I had fantasized about and I told her it was better.
Her eyebrow went up on that. When I finished she walked over and hugged
me again.
"What was that for?"
"I still can't believe you willing want to suck dick and swallow cum.
If you get the chance are you going to let him fuck you?"
I just smiled at her in response.
"You slut!" She laughed. "Well, I am betting after he sees you tonight
you will get to experience that also. I know we normally don't do much
for Pirate Night but this trip, for you at least, it is going to be a
little different. I think you are going to be really happy when you find
out what we have planned."
"Can you give me a clue what you mean?"
"Let's just say that I have noticed that it isn't just the princesses
outfits that you seem to admire at Disney World. It is just after three
o'clock now. I think we are going to need a couple hours to get ready.
So if you want some pool time I would go now."
"I think I will skip the pool today but I am going to go up and get a
drink. Do you want anything or want to come with me?"
"That sounds great. Sure."
We decided we would go to the pool bar to get our drinks and saw Jordie
sitting in the pool next to the hot guy in the bathing suit from the
other day. When she saw us, her cheeks got red and she gave a quick
wave. We looked for Pat but didn't see her. Sarah ordered our drinks
and found a shady place to sit. I pointed out that the super-hot man
and woman we had seen at the pool before were back.
"Okay, so you have to pick one of them for sex. Which one?" Sarah asked
me.
"Him," I said without hesitation.
"Wow, that was fast. You didn't even consider her."
There was an awkward silence and I didn't really know how to respond to
that.
Thankfully Jordie walked up right then. "So Brandi HOW was your
afternoon?"
"It was great. How was YOUR afternoon?" I smiled broadly at her.
She laughed. "I am going to head down to the room. Not sure if Sarah
told you but we are going to need a little more time to get ready this
evening. Can you come by the room at 5:00 so we can get started?"
"Sure. Thanks."
She walked off and I asked Sarah for some clues about what was going on
and she refused again. We did decide to have another drink, the drink
of the day today were Rum Runners. I noticed that Sarah's eyes were
focusing in on the group of young men that were hanging out with
Jordie's friend.
"Maybe you could get Jordie to introduce you to them. Is there a
specific one that has your attention."
"What? What are talking about?" Her cheeks were red and she knew I had
caught her.
"You know exactly what I am talking about."
"Okay, you caught me. The taller dark haired guy on the right of
Jordie's friend, he reminds me of Tim Riggins on Friday Night Lights."
I smiled because I remembered she had a crush on that character when it
was on TV. She stood up and said we should head back to the room. I
noticed that we took the long way to the elevator which brought us right
by the group.
When I laughed, she just smiled. It was an interesting moment of
marital intimacy, mind reading and almost silent conversation between
the cross dressed husband, who three hours ago had sex with a man, and
the wife who was checking out a much younger man.
When we got to the room Sarah asked to shower first and I took the
moment to lay on the bed and close my eyes for a few minutes. I must
have dosed off because I woke up to Sarah telling me that Sleeping
Beauty needed to get her butt into the shower. She told me if I hadn't
shaved my arms and legs recently I needed to make sure I did that and to
shave my face again.
After the shower I found the room empty but a pair of panties and my
swim suit cover up laying on the bed and figured that Sarah was in Pat
in Jordie's room. I quickly put them on and went next door.
Pat and Jordie's bed was covered in all sorts of clothes and items and I
was taking that in when Pat said "I think we should all tell each other
about their afternoon. You should start Brandi!" And she broke out
with wonderful laugh.
"I thought maybe you could tell us about your new, very close, friend
Pat," I responded smiling. Sarah and Jordie laughed at that and Pat got
red.
"Come on Girly. At least let me know if you used the lesson's I gave
you this morning."
"Yes. I did."
"And?"
"And, it was amazing."
We all chuckled and Jordie said it was time to start on my makeup. The
eye makeup this evening was heavier than normal, extra eye liner,
thicker mascara, maroon and pink eye shadow and shading and dark red
lipstick. I complemented her on another amazing job.
"Pat can you do your magic on my hair?"
"We have some different magic for your hair tonight," Sarah quickly
interjected. "That will be the last thing we do. Did you bring your
boobs with you?"
"No, I will go grab them."
When I returned Sarah said, "Okay, we need to have a quick discussion
about modesty. Getting you dressed is going to take a little extra work
so are you comfortable with Pat and Jordie seeing you in your
unmentionables? Remember it will be just us girls." She smiled.
"Yes, I guess."
"Okay, take the cover up off but leave your panties on."
I did as instructed and Sarah picked up a corset from the pile on the
bed. It was pale pink and had lots of lace built in it. There was also
garter straps hanging from it. She wrapped it around my stomach and as
she started to hook it in the back I felt it squeezing me. I was handed
a matching bra that I put on myself.
"Spin around so your back is to them." She nodded at that Pat and
Jordie. "And drop your panties."
Again I did as I was told and when I reached down to take the panties
off my foot I heard Pat say. "I really wish my ass looked like that."
Followed of course by her laugh which caused both Sarah and Jordie to
chuckle.
Sarah handed me matching thong panties and I pulled them in place. She
then took one of the garter straps and tucked it through panties,
eventually all four were done and the result was the panties were over
top the garter straps.
"I think you are going to really like what is next."
She handed me a thigh high stocking. It was fishnet with a floral
pattern on it and was honestly beautiful. I rolled it up, stuck my toes
in, and then up my legs. Sarah helped me attach it to the garter tab
and we repeated that on my other leg. I wanted to see how I looked in
the mirror but Sarah was already handing me the next item. It was a
bright pink with white lace edging, sort of peasant style dress that
looked fairly short.
"Do you recognize it yet?"
"Is it a servant wench outfit?"
Sarah shook her head no and when the dress was in place I was right. It
was short falling, above my right knee by about two inches and by at
least five inches above my left knee. It also felt loose in the stomach
area. I was actually a little disappointed with the fit. Then she
handed me a deep maroon sleeveless vest and had ties running up the
front. Once it was laced in place and a wide black belt was added the
look completely changed.
"Recognize it yet?" she asked again.
I thought I had an idea but I didn't want to disappoint her if was
wrong. It was obvious this was something she had put a lot of thought
into. I shook my head no.
"Well the one thing will definitely give it away so I am saving that for
last."
She then reached under the bed and pulled out a pair of brown boots.
My huge smile when I saw them made Sarah smile. They were hot. It
looked like the heel was about 4 inches, and the boot was suede with a
leather cuff at the top and a leather toe and leather straps across the
feet with buckles also. I immediately pulled them on. They came to
just below my knee and looked fantastic.
"These are amazing. And I am ready to guess. It is a pirate outfit and
since I am going to be wearing a wig, different magic right." I looked
over Pat. "I am assuming it is going to be a red headed wig!"
"Yes, it is." Jordie pulled a red headed wig and a maroon tri corned
pirate hat out of the closet and brought them to me.
Pat intercepted the wig and told me to sit as she attached it to my head
and made sure it sat exactly right. I stood up and put the hat on and
when I turned to the mirror I saw Redd the Pirate from the Pirates of
the Caribbean ride. I was also hotter than her because my dress showed
off way more leg and stocking than her dress and she her boots
definitely didn't have a four inch heal.
"Oh my God! This is so amazing! Thank you so much." I again hugged
Sarah.
I am not sure if Sarah really understood how deep this went for me. I
am pretty sure that 'The Redhead' who was a part of the Pirates of the
Caribbean at Disney World for decades, was one of my many crossdressing
triggers. Whenever I rode the ride, I would always look forward to
seeing her red dress, black stockings, red heels, and briefly daydream
of being her.
A few years ago Disney had decided that a red headed woman, tied in a
rope, being auctioned off was no longer something they wanted to portray
and announced it would change. Many people were upset by this but the
debut of Redd the Pirate was a hit. I found that I suddenly wanted to
be a red headed female pirate. Now, whether knowingly or not, Sarah had
allowed me to become her for the evening.
"So am I the only wearing a Pirate Night outfit? While I love it, I am
going to definitely stick out in our group."
"No, I am going to change in just a minute. I was waiting until you
were done," Jordie said.
"Okay, great. I will get out of here and let you change."
"Pat and I are doing a little Pirate Night dressing. I have some pirate
LuLaRoe leggings I am wearing tonight and she has a dress. How about we
be ready to head out at 6:15 and we can go to the lobby and see what
everyone is wearing."
Sarah and I went back to our room and she changed into the leggings with
a cute peasant top. I told her they were cute while continuing to
admire that outfit I was wearing in the mirror. She caught me and
smiled and again remarked that I kept reminding her of all the things
that she took for granted as a woman.
Pat and Jordie knocked on the door about 20 minutes later. Pat was
wearing a Captain Hook LuLaRoe dress and I complemented her on it. When
I stepped out and saw Jordie I gave her a quick wow. Like me she was
wearing boots, hers had a three inch heel on them. They were black and
actually came above her knees. Fishnet stocking covered the couple of
inches of her legs that were visible before a short skirt maroon skirt.
A white shirt with ruffles for the sleeve cuffs and at the CHEST area
along with a corset on the outside of the shirt. She had chosen a red
and black bandana to cover her head but her blonde hair cascaded out
from under it.
We quickly fell into what had become normal, Jordie and I walking
together in front of Pat and Sarah. I was really glad that Jordie was
wearing an outfit similar to mine. I also loved that with every step I
could feel a slight pull of the garter straps on my leg.
"I am sure that those two will be getting railed tonight if they want
to." Pat laughed heartily after saying that.
"Well the red head told me earlier today that she wants to be fucked."
Fortunately Sarah said that fairly quietly.
"Oh what a little slut she is turning out to be. Getting dick twice in
one day." Again Pat's wonderful laugh filled the hall.
Jordie put her hand on my shoulder and leaned closer. "You won't be the
only getting some tonight. Pool boy and I are planning to get together
later."
"Good for you! I hope to hear all about it," I told her.
We made it to the lobby and I was glad to see that Jordie and I weren't
the only female pirates. We definitely got some looks though.
Admiration from the men and a couple of dirty looks from a few women,
mostly the ones who had caught their husbands checking us out. We got
into the line to have a picture taken with Pirate Mickey. We did one
with all four of us and one with just Jordie and I. Mickey mimicked
blushing for that pic.
Are we ready to head to the pub Sarah asked and we all nodded. Even
though my nod indicated yes, my mind wasn't in total agreement. I was a
little nervous about Steve seeing me like this. Or maybe it was about
Steve's family, including Lisa seeing me like this. I was also pretty
nervous about seeing Lisa. While she had told me it was okay for me to
be with her husband, that was different than having actually done it.
What I was most scared about was seeing Steve. We had not communicated
since he left this afternoon and I was really worried that he had the
time to reflect and now had regrets. While my appearance didn't show it,
a man had been the one who had blown him this afternoon, would he still
be okay with that? How would I react if he suddenly rejected me?
Lastly, what would the dynamic be between Sarah and Steve?
Way to quickly the walk to the pub was done and we entered to find that
his family wasn't there. I was now really beginning to panic a little.
We took our normal table and ordered our drinks. Being Pirate Night we
all ordered something with rum in it. I was definitely fidgeting and my
face must have shown my concern.
"Are you okay?" Sarah asked.
I nodded yes.
"Oh, I just figure it out. Worried the guy you had sex with earlier
today is blowing you off, right?"
I started to deny it, but honesty had worked really well with her so far
so I nodded yes.
"Well you are getting all kinds of girl experiences today aren't you.
First date, first kiss, first time giving a blow job, and now first time
wondering if you have just been used as a cum dump."
Pat leaned in. "Men really are asses you know. The problem is they
have that beautiful. tasty thing between their legs." She smiled,
trying to lighten the mood.
"Listen, look around, you could pretty much suck the dick of any man in
this place based on the way they are all checking you and Jordie out.
Don't worry, you will find another cock to suck or to fuck you in your
ass." I couldn't tell if Sarah meant that as a comfort or if she was
being mean.
I had just decided to ask her when I heard. "Sorry we were late getting
here some of us were trying to get pics with Jack Sparrow." Lisa said
this as she looked at Susan and Trevor. No one in their group had
dressed up but they all looked nice.
I was looking past her trying to spot Steve and saw he wasn't in the
group. Melissa saw this and came up and whispered. "He stopped in the
men's room and will be here in a minute." She winked as she moved away.
Sure enough a few minutes later Steve came in. He said a general hello
to all of us. I fought my desire to jump into his arms and kiss him.
Or was it my desire to drop to my knees and kiss him. It took a little
while but eventually he managed to work his way to where he was close to
me.
"You look fantastic. It is killing me having to keep my hands off of
you," he said quietly into my ear as he leaned down.
"I am hoping later you will have your hands on me and your dick in me."
He actually blushed hearing that.
I looked up and both Sarah and Lisa were watching us. Neither one of
them gave away what they were thinking with their facial expressions.
We all had a second drink while the trivia was played. Sarah and I told
Pat and Jordie that after the show and fireworks there was a huge buffet
so this would be a good night to go light at dinner.
Trivia ended and we all moved towards the exit to go down one floor to
dinner. I felt a hand grab my arm and pull me close and turned to see
Lisa. She smiled at me. "I heard you had a good afternoon."
"Oh, I am so glad you smiled. I have been worried that you were upset
with me."
"Well, I am upset that you look so good tonight. And I might be a
little upset that my husband is going to spend the whole time at dinner
anxiously awaiting for the chance to fuck you." She squeezed my arm and
smiled again.
"Lisa, if you don't want me to do that just tell me and I won't."
"Sweetie, if you don't get fucked while wearing that outfit, there is
something wrong with this world." She let go of me and moved up with
her group.
I noticed that unlike last night, where we walked together to the
restaurant, Steve was several people ahead of me.
Sarah caught me. "Everything okay with Lisa?"
"Yes, or at least I think it is. Are we okay? I mean is what I am
doing okay with Steve okay with you?"
"I told you, I want you to have these experiences, so yes. Remember
this just about sex okay."
We were taken to our seat in the restaurant. We were eating in
Animator's Palate again tonight. They were serving the Pirate Night
Menu and it would be the same menu in all of the restaurants. At each
of our seats was a piece of paper with the outline of person on it.
There were also multi colored markers available. Sarah told Pat and
Jordie to start coloring them in.
I choose, to the best of my ability, to make my person look like a
reasonable adaption of my outfit. I thought I had done a pretty good
job it and showed it to Sarah who agreed. There was also a spot to
write you name on it. I wrote Brandi and made a point to dot the eye
with a heart. Sarah smiled at that.
The waitstaff took our sheets and our orders. Both Sarah and I were
excited for Pat and Jordie to see what would eventually happen. The
dinner conversation was actually a little subdued. I admit that my mind
was distracted. I was trying to figure out the how of getting time
alone with Steve this evening, along with being more than a little
nervous about what would happen if we did end up alone.
As we finished up dinner all the screens in the restaurant came to life
and Mickey came on. It took a minute but it was quickly evident that
the drawings we had done earlier were now starting to appear on the
screen. Pat and Jordie watched wide eyed and both yelled out when they
saw their drawings appear. Eventually Sarah and mine also showed up.
Then they started our drawings started to move and eventually they were
added to scenes with Disney characters with Disney music. Definitely
some Disney magic had happened.
"That was so cool," Jordie said.
"Just wow," Pat added.
"We need to head up to the top deck so we can find a place to see the
show and fireworks," Sarah said.
A quick stop in the little girls room for all of us, something that I
was now completely comfortable doing, and we headed up. Because we had
done this before we found a spot on the port side that looked down on
the pool deck area. I continued to look around for Steve. It had
dawned on me that we had not made a plan and right now I was thinking we
wouldn't be able to get together later.
I leaned over to Jordie who was standing next to me. "So how are you
and Pool Boy getting together tonight?"
"We are supposed to meet at the lobby bar after the fireworks end."
I smiled. "That was a good idea."
"How about your and Steve?"
"That's the thing, we didn't make a plan."
"Oh, well I am sure he will figure it out."
I really hoped she was right. As people packed in tighter I became less
sure of that. Jordie grabbed my arm and pointed. Across the way was
Nancy and Melissa but I didn't see Steve or Lisa. As the show started I
continued to scan. The show was on the pool deck and pirates danced and
sang. Eventually Jack Sparrow should up at the top of one the smoke
stacks and rappelled down, before fireworks began to shoot off while
Pirates of the Caribbean music played loudly. Disney was the only
cruise ship in the world that shot off fireworks at sea.
The show ended and people began to move about, some headed to the
buffet, others back to their cabin. Sarah asked me what I was planning
to do. I honestly didn't want to eat but I didn't know what to do.
Jordie told us she would see us later and headed off. I told Pat and
Sarah to go ahead and do their thing and not worry about me.
"Are you okay?" Sarah looked she had genuine concern.
"Yes. Just disappointed."
At the same time Sarah suddenly began to smile I heard. "LADIES!"
loudly belted out and recognized Lisa's voice.
I whipped my head around and saw Lisa, but more importantly Steve. We
exchanged small talk as a group about the fireworks show while I was
trying to figure out how to politely say, in front of my wife and
Steve's wife, hey I need Steve to take me somewhere and fuck my brains
out.
"Are you all going to buffet?" Lisa asked.
Pat and Sarah responded yes but I said, "No, I am not hungry. I think I
might go get a drink."
"I was thinking I would like a drink also," Steve said.
"Yea, I am sure that's what you were thinking you would like." Lisa
shot her eyes at Steve. "Sarah and Pat how about we go to the buffet?"
They agreed.
"Brandi, you and Steve can go enjoy a drink." She smiled at us even
though the accent on the word drink made it obvious that we all knew we
weren't going for a drink.
The three of them moved off and Steve and I stood there. I smiled at
him and said, "My room."
He grabbed my hand and pulled me that way. I was hoping we would be
alone in the elevator but we weren't. When we got to the hallway we
were alone and I stopped him so I could kiss him. The minute we stepped
in the room I knew what I wanted. Steve headed towards the couch. I
stopped him at the bed.
Again, I kissed him passionately and my hand went to his dick which I
could feel through his pants. I dropped to my knees and worked his belt
and pants free so I could get his dick back in my mouth. It felt so
warm and wonderful there. I struggled for a minute in deciding if I
wanted him to cum this way again.
He took that option away from me as he took my head in his hands, and
lifted me upwards again. Standing up we again kissed passionately.
Stopping for a second, I turned to the vanity and grabbed my clutch. I
reached into it, feeling the condom, I considered that for a second but
just took the lube out of it. I handed it to Steve and he smiled before
kissing me again.
"I have never done this. At least not with a real dick. I want you
badly, but please be gentle."
"Okay. Say stop if you are uncomfortable. How do you want to do it?"
"Bend me over the bed, please."
One more hard kiss and he spun me around, pushed me over and spread my
legs. I felt my nervousness increase as my dress was pushed up and I
felt my ass being exposed.
"God, I have been wanting to see your ass like this for days." I felt
the strap of my thong pushed out of the way and then a slap across my
butt. It stung and I yelped a little, I also knew that was probably the
hottest thing I had ever had done to me and I would want that again.
The next thing I felt was lube in the crack of my ass. This was followed
by a finger circling the bud of my asshole as more lube ran down and
then a finger was in my butt and I let out a small gasp but also backed
my butt onto the finger.
Steve laughed. "Oh you are ready for this aren't you, slut." And his
other hand slapped my ass again. I moaned out loud. Then gasped again
as I felt a second finger added to the first. Once again I rocked back
and this resulted in another slap. The sting of that combined with the
fullness in butt was driving me crazy. I felt my own dick pressed
against the front of my thong and trapped between me and the bed.
He removed his fingers and I could tell he was completely removing his
pants. Then he grabbed on to my hips and I felt his dick in the crack
of my butt and he slid it back and forth several times. I tried, almost
desperately, to get my asshole to line up with the head of his dick. I
needed something back inside of me.
"Jesus, you want this dick badly don't you. You are a cock whore."
"Yes, I am cock whore please give me you cock." I know I was pleading.
I felt the tip of dick resting right at the entrance and attempted to
push back. I was prevented from doing this by his strong arms pushing
down on my hips, but he leaned towards me and the tip of dick slipped
into me. He held it there for a minute then, instead of slowly sinking
into me, he took one hand and slapped my ass again while sinking
completely into me. Both of them burned and I cried out but I also
loved the full feeling I was experiencing.
"Are you okay sweetie? Do you want me to stop?"
"God NO!"
A laugh and he rocked back slowly, leaving just the tip in me and once
again I attempted to back on to it. I was prevented from doing this but
thankfully he pushed back in and this time the tip must have hit my
prostrated because I suddenly felt wonderful.
"Please! Just fuck me!"
He started to move back and forth, in and out of me. Every time he
moved over my prostrate my pleasure grew. My own dick was being
stimulated by the panties I had on and the friction caused by being
pressed again the bed. He would speed up for thirty seconds and then
stop. Sometimes buried to the hilt and other times with just the tip
left in.
"Please Steve. Fuck me hard. Don't stop." And again I felt another
slap and his dick was again buried in me.
He stared to move faster, sawing in and out and the pleasure running
through me grew. I also heard him starting to breath heavier and a
couple of oh Gods from his mouth. "You tight ass bitch, you feel so
good on my dick!"
I grabbed handfuls of the comforter. "Fuck me, fuck your tight ass
bitch slut. I need your cock!"
"Oh holly God. Yes."
The grip on my hips tightened and he moved even faster which sent me
almost to the edge.
"Oh fuck I am going to cum," I called out.
Steve fucked me even harder and I felt my cum spurting into my panties.
The orgasm coursed through my whole lower body. I had never felt one
like this.
"Fuck. I am going to fill your ass with my cum."
"Fill me up, cum in my ass."
I heard him cry out, I felt his dick spasm in me and then I felt him cum
inside me.
He collapsed over top of me. I turned to him wanting to kiss him but my
lips couldn't reach his. I could feel him softening and as he pushed
himself up and stood suddenly my ass was empty again. I stood up also
and kissed him quickly before moving to the bathroom. I grabbed a towel
and used hot water to make part of it wet.
I returned and his butt was resting on the side of the bed. He smiled
at me and I remembered it was just a few days ago that his smile was one
of the things that had drawn me to him. I knelt in front of him and
used the towel to clean him. I also realized how much I enjoyed being
on my knees in front of him, it was truly a submissive position. After
cleaning him, I gave his cock a quick kiss and as I stood up, I felt
semen leaking from me and told him I needed a minute to freshen up.
Stepping into the bathroom, I cleaned up the best I could including
freshening up my makeup. When I came out he was sitting on the couch.
I moved over and sat down at the far end. He looked at me and raised
an eyebrow before sliding over and kissing me passionately. This is
what we were doing when Sarah entered the room. We both jumped and
quickly moved apart.
"Oh. I am sorry. I don't know why but I thought you were going to his
room. I will leave."
"No, don't do that. It is late I need to be going," Steve said as he
stood and began to move to the door.
I quickly got up and followed him. We end up in a very awkward moment
when Sarah, and the narrow passage at the end of the bed, was between us
and the door. We eventually jockeyed around each other, at the door I
kissed Steve again before I pulled him close.
Whispering in his ear. "Thank you, that was everything I hoped it would
be. I really want it to happen again."
"Thank you." And he stepped out the door.
I turned back into the room. Sarah was standing there.
"Well since the room reeks of sex I am going to assume he fucked you."
I nodded.
"And?"
"And what?"
"Was it good? Are you glad you let him? Do you want him to do it
again? Are you okay?"
"Yes." I don't know why but for some reason I wasn't ready to talk
about this with Sarah. I also knew that I was mad at her for being here
right now. I wanted Steve in the room now, not Sarah. I wanted to be
climbing into the bed with Steve in it and I wanted to spoon against him
as I drifted off to sleep.
"Yes, what? Yes, to all of it?"
I nodded. "Would it be okay to talk about this in the morning?"
"Okay, whatever. I am not sure what is going on right now but remember
you are the one who just got fucked by someone else, not me."
I had started to remove my outfit and eventually laid it neatly on the
chair. I stepped into the bathroom and removed the wig, my makeup and
cleaned myself up again. I took the towels I had used for this and for
Steve and threw them in the bathtub in the other room. Sarah and I
passed each other as she went to prepare for bed.
I climbed into my bed and realized I was exhausted but I also wondered
how well I would sleep.
"Good night Sarah."
"Good night... Brandi." The pause between the good night and my girl
name seemed to explain exactly what was going on. Was Brad possibly
gone forever now.
Thank you to everyone who has stuck with this story. I never expected
it to be this long. The final part will be coming soon.