Alissa came to me the next day and said, "I'm so excited! I booked us
for a week at Beaches Turks and Caicos! They have a great scuba program
and it's all-inclusive, so we don't have to worry about a thing! I
booked the last week of October, we have 3 months to shop and make sure
we have the right outfits. How exciting is that, Amy?" I excitedly
said. "That's awesome Alissa, I always wanted to dive there, it's
supposed to be amazing" she quickly agreed and said, "I knew you always
wanted to go there, so I decided to splurge since it's a girls only
trip" which she finished saying with a big smile. I was as excited as
she was pumped. I know she will put all of her effort into making this
a great vacation. She said, "look, I have already made a list of things
we will need" as she handed me the list. It said:
1. new scuba suits each 3 - one piece
2. 3-4 bikinis each - beach and pool
3. 2-3cover-ups each
4. 2 maxi dress outfits each
5. 2 mini sun dresses each
6. Beach bag
7. night sandals, wedges and pool shoes
8. purses and accessories for Amy
9. clubwear, dresses and heels
10. check nail polish
11. Travel outfits
12. Tattoo
13. xx
I saw this and thought I was already in for it as I agreed. I was
nervous and excited at the same time. I asked her about #12 on the
list, and said, "Alissa, what is number 12? You say a tattoo? What is
that about?" She quickly responded, "oh, right. I was going to tell you
that I wanted you to get a tattoo for me. I was planning on sketching
up a few options and you can pick one. You will have the choice of what
you want." as she walked away. I just panicked a bit..a tattoo, I have
never wanted a tattoo, why would she do this?
A few days later we started shopping. We went to a scuba shop about an
hour away that we liked to buy some outfits. I had my guy clothes on of
course to start. In the car before we pulled out of the garage, she
reached behind the seat and asked me to change my shoes. She handed me
my Clarkes sandals that were similar to mine but a slight 1.5" heel on
them and they were open-toed. My toenails were polished a light beige
this time so they did not stand out. She also asked me to put on a
touch of mascara that she pulled out. I was fine with this, flipped
down the mirror and put on the mascara and we drove to the store. It
was a pretty big store and not too busy at the time. We selected some
swimwear and scuba wear and just used the change rooms ourselves as no
one else was in there. Alissa was bringing me scuba suits to try on.
She had to help me with each as they were all so tight and form
fitting. I was surprised when I looked into the mirror on the first
one. Alissa saw me and squealed and clapped. "OMG Amy that looks
amazing on you! Look at your curves, they are showing. Your ass looks
delicious and look at your boobs." When I looked in the mirror, I was a
little shocked. My hair was up in a man bun, I let it out and shook it
around. As Alissa smiled, and when I looked at myself in the mirror
from that back and side, I was thrilled! I looked sexy. As I was
admiring myself, there was Alissa coyly playing with her nipple. I just
smiled and she said, "Amy, you may need to suck my nipples and make me
come in here before we leave. You look so amazing in that." That make
my cock twinge in its cage. I was so excited on how the scuba suits
looked on me, we were both all smiles. She looked so incredible when
she tried hers on and I couldn't wait to get all dolled up beside her.
I tried the black and white one on last and after seeing it on me, she
yanked me behind the curtain, just standing in her bra and panties
asked me to suck her nipples right then. I closed the curtain; she
pulled her suit down exposing her gorgeous tits and I went to town on
her. She came so hard just standing against the wall with me and
finished with a big smile. I was thrilled that I made her come so fast.
I went back to my change room and we tried on another outfit each and
settled on our purchases. As she was done, she came in my room and
helped me out of my last outfit, she also pulled down my panties. She
then reached under her sun dress, pulled hers off and swapped them with
me. Her panties were soaked as I suspected, but I was actually thrilled
to put them on. Which, by the way now, were fitting me a bit better to
my form. We got ourselves together and ended up buying me two short
black scuba suits ones and one flowered black and white design. All
three were the short style and the ones she got were full body wet
suits that covered her legs, she liked that look for herself. We paid
and left the store. As were walking to the car, I was thinking to
myself, I wonder what it would feel like to have a pussy and get my own
panties wet. We got into the car and she asked how my panties were and
I just said, "They feel so good and wet, I love them." She just smiled
and said, "Amy, that was awesome, let's go look for some regular
bathing suits and clothes now." I thought, oh wow, she is on a roll as
that would probably end the same way too. She said, "Thanks for wearing
those cute sandals, your toes look so pretty and I love the bit of heel
that gives your legs and ass a nice look, you should be wearing some
kind of heel more often to show off a little." I just smiled.
Alissa said she would drive and started driving to another place. I
asked where were going and she said she arranged for an after-hours
appointment at the Beach Bunny store. I knew the store and have always
loved their stuff. I asked what were going to buy and she said, "I
thought it might be a store where we could get most of our shopping
done for the trip. Since we both love their stuff, I called and spoke
to one of the managers that offered to stay late and help us. I told
her all about you and she was excited to help. I was hoping to get you
all dolled up first, but this will have to do today. Her name is Serena
and I asked her to treat you like one of the girls." I said okay and
was excited to have the store closed so I would not worry about being
seen by others.
We got to the store and knocked on the locked door. Selena answered and
she was this 40+ year old drop-dead gorgeous blonde. She must have been
a size 2 and looked fantastic. She greeted us both with open arms and
called me Amy right away. She locked the door and told us about the
layout and said she expected us to be a couple of hours and to take our
time. Alissa saw the swimsuits first and said to her, "Thanks Serena,
can we start with swimsuits? We want a few bikinis each and maybe a
one-piece for Amy." Serena said, "Absolutely Alissa, please make some
selections and I will get you set up by the change rooms. Please keep
in mind that people cannot see in our windows, so feel free to browse
anywhere in the store if you happen to be in the middle of trying
something on." Alissa grabbed my hand and we went for the suits and
Serena went towards the change rooms on the other side of the store.
Alissa was like a kid in a candy store. She quickly picked out a bunch
of suits for both of us in various sizes, I was a bit nervous, but
Alissa was comforting me and asking me to get ones I liked. I grabbed a
few as well, we went to the change rooms. Serena asked that we leave
our underwear on, which I quickly thought, oh no, I now have on
Alissa's wet pink silk bikinis. What was I to do? I just went for it.
Alissa had my panties on which looked like white silky bride panties
with some lace.
I went into the change room and Serena wheeled over two clothing racks
to put beside our change rooms. She had a little sign on each that
said, "I want these" and the other said, "I don't want these." The sign
was in the middle of the bar and a little arrow on each pointing out.
We each had our own rack. Serena obviously did her homework and was
ready for us. I went into the change room, let my hair down and got
dressed in the first bikini. I admired myself in the mirror in the room
and Alissa asked me to come out. She looked like a goddess in a
beautiful black bikini. I was in a similar flowered patterned one. My
top was a triangle type of style and hipster bikini style. Both Alissa
and Serena both stood speechless when they saw me. Serena said, "Oh
wow, Amy. I had no idea you had such a cute body under those nasty guy
clothes you were wearing. You look beautiful, please give me a spin." I
gave a cute little spin as Alissa watched. I could tell Alissa was
getting turned on, which was great. Serena said, "Amy, I have a feeling
we will be finding many outfits for you today. If you wear them half as
good as you wear this bikini, you will certainly be getting a lot of
attention from the guys." I said a polite thank you. Alissa said, "Put
that one on the rack as a keeper" and I said the same for hers. I went
into the change room for the next and she came in with me with her
purse. She dropped to her knees and said to me, "hold on, I almost
forgot." She took down my bathing suit bottom and my panties. She
shuffled in her purse for the key to the cage. She unlocked it and
pulled out one of those fancy tuck tape things. She put it on my which
pulled my cock and balls back and out of sight. She said, "now that
should make you look even better; I am sure Serena will notice how much
better you can look." And then she left my room. She was so right, it
looked so smooth with no evidence of my cock and balls showing. This
certainly did help.
I tried on the next one and came out, Alissa said, "OMG, you look so
hot in that bikini too. I did not realize how the hormones were making
your tummy and waist look so feminine as well. I think we should look
at some shorts and crop top sets here too. I am making your panties wet
now, hope you don't mind. That suit is a keeper too." she said with a
sexy smile as she went back into her change room. We ended up there for
three hours and bought tons of clothes. Serena was awesome, I think I
must have tried on every item in the store. We bought four bathing
suits each, three dresses each, shorts set, shoes, cover ups and even
some lounge wear and workout clothes. I was in heaven. There was a maxi
dress and long skirt in the same material that was my favorite and
really cute on me. The material was black with little red hearts.
Alissa was finished and as was finishing up in my change room putting
my original clothes back on, she came running into my change room and
told me to try on the one last dress she just found on the way to the
cash. It was the same material as the maxi dress in a mini wrap dress
form. It was a really nice dress and fit me perfectly. I came out the
room to show her as she was at the counter with Serena. I sauntered up
to them. They both stopped and were staring for a a few seconds and
didn't say anything. They both almost said at the same time, that i
looked so beautiful and the dress was stunning. They said that it was
the best dress ever on me. Serena said, "I think I have a perfect pair
of wedges to go with that," and ran off. We waited as she proudly ran
back to us with them. Alissa loved them and said, "those are perfect
Serena, great choice. Amy put these on." I slipped them on and they
both had a huge grin, ear to ear. Alissa said, "Serena, you have
outdone yourself, those wedges look perfect. Amy, take these earrings
and leave the dress and shoes on. You will wear this home. Go into the
change room, gather your things and put on the earrings and lipstick."
Then then both smiled and went back to the checkout counter. By the
time I gathered my things and went out, Alissa was ready with all of
the bags and took care of everything. Serena came over and gave me a
hug and said I was beautiful and thanked me for shopping there. She
held up a finger to gesture "wait a second" and ran to the counter and
back after grabbing a couple of things. She had a hair comb that she
quickly pulled back and tied my loose hair from the sides to pull back
and then she then misted me with a bottle of their store perfume. It
was so feminine smelling and I felt wonderful. She said to us on the
way out "Amy you look stunning, you should dress this way all of the
time! Have a great holiday!" I proudly wore my new dress and 4" wedges
to the car carrying our bags.
We got into the car, I sat gingerly and smoothed my dress as I
navigated my heels and keeping my knees as close as I could. I sat, and
looked at Alissa. She was staring at me in silence. She said, "Wow, you
did that so graciously and in such a feminine way. You are looking so
hot Amy. That was probably one of the most exciting evenings I have
ever had in my life. That was so incredible, you tried on everything
and looked so good in everything. I think you were meant to be a girl!
I know we couldn't do this with Serena but I think I need you to suck
my nipples and pussy right now in the car." We both got out of the car
and jumped in the back seat. She reached under my dress and pulled my
panties down. She pulled off the tape device and my cock actually
sprang to attention, which surprised me. She said, "Maybe you need to
stick that cock into me right now," as she pulled the top of her dress
down exposing her nipples. I put my cock in her soaking pussy and
leaned in to start sucking her nipples. She came in one minute. She
pushed me back, and started playing with my cock under the dress and
talking to me. "You looked so hot tonight, I am sure you would make
many cocks perk up wearing your new clothes. I am sure you would love a
big hard cock in your mouth right about now, wouldn't you?" I exploded
allover her hands. "Good girl," she said. "Now lick this delicious cum
all off my fingers." Which I did without hesitation. She started
calling me and teasing me while I was doing this saying, I was a cum
slut and don't I wish I had come in my mouth every day. I just moaned
in agreement. I was pretty happy to come, especially after an exciting
night.
Alissa had me drive with my wedges and we went home. She knew our son
was out, I spent the rest of the night and a few glasses of wine in my
pretty dress and wet panties. We went through our purchases and started
to pack our bags already for our trip. I really felt like her
girlfriend this night. She asked me to keep her panties on, put my cage
on and thanked me for one of the best days of her life. She gave me a
pink silk nighty to almost match my panties to sleep in and admired my
perky nipples sticking through the fabric as she put it over my head
and down on me. She gave them a quick little feel that sent shivers
down my spine..in a good way. She gave me a hug and reached around and
squeezed my ass and said, "Amy your ass feels so delicious and jiggles
just right, especially in these little silk panties." I smiled and
said, "Goodnight." I didn't say anything in the moment, but for some
reason with her grabbing my ass like that it was a complete turn on. I
also felt my nipples twitch rubbing up against her when she reached and
grabbed my ass. It made me feel sexy and maybe a little passive, but it
was hot.
We still had a few things to get for our holiday, but easily got that
done. I was left in corset training again until our trip as she wanted
me to lose another inch off my waist for our bikinis in Turks. We
followed a good plan for a couple of months to make it happen. She said
the goal was to leave the corset at home.
The tattoo became a focus after that. Alissa was a bit of an artist;
well she could draw. Her favorite thing was butterflies, she collected
butterfly things and if clothing had a butterfly, she often bought
those items. When it came to the tattoo, she wanted me to have she
presented four drawings to me at dinner one night. She asked me to pick
one. Each one she sketched was for a different area of the body. All of
the butterflies were the same in her designs, they were all outlined in
black and pink and white in color. Each was scaled to fit each area.
The first was a tramp stamp for my lower back. It consisted of two
butterflies together and a curly line beside each. The butterflies were
about 3 inches wide and 2 inches high and then the lines. She said this
was her favorite as she thought it would be nice for her to look at
when she fucked me from behind. The second was a smaller double
butterfly image that she would want just above my right ankle. The
third was the same but for under my right wrist and the fourth was a
smaller version but to go on my ring finger with the butterflies on the
top side that looked like a ring itself. She said the only way to hide
the ring one would be to wear my wedding/engagement ring. Only the
tramp stamp one could be hidden, but not all of the time. It would be
exposed probably in female clothes, bathing suits and my new crop tops
and short outfits for sure. The ankle one may be hidden more, but I was
wearing shorter cropped pants more these days. I was not sure what to
select. She said I can pick any one I like, but I will be getting it
tomorrow as she already made my appointment. For the tramp stamp and
ankle tattoo, if I selected those, I would need to dress appropriately
to get them done. I asked what that would be and she just said it was a
surprise. It was a dilemma and I took a glass of wine to think about
it. I told her I would do the ankle one.
She said, "good choice! I was going to have you wear that cute little
white pleated mini that looked like a tennis skirt for that one. But I
think you can just wear some skinny ankle jeans or capris; I will let
you decide. Either way, I think you should also wear those brown casual
lace up shoes we bought that have the 2.5" rubber heel." I just said,
"okay Alissa." Obviously, this was something she planned carefully and
I will do it for her. She said, " I was originally thinking to have you
get a tattoo that looked like pink and dark colored hair above your
cock like your bikini area that was lasered, in a little feminine
triangle, but I could not draw it well. I am still considering that and
think it would be very cool on you."
I ended up wearing the skinny jeans and the shoes she wanted. I had to
go alone and the tattoo artist was a girl named Jaz. She was quite an
artist. She had instructions from Alissa and everything was taken care
of. It hurt like hell. She said Alissa asked her to add some red to it
to brighten it up, which she did. It was quite amazing when finished,
but it was also very feminine looking. She said she made it a bit
smaller than Alissa wanted and blamed the size of the area. She said,
"I feel bad for you having to wear this. But in a way, I think it suits
you well. I will let Alissa know I had to do it a little smaller,
please wait." Jaz took a quick pic and sent it to her and then she
called Alissa as she walked to the back. They spoke for about 5 minutes
and she came back. "Alissa said it was fine and loved the design and
color, so I saved you a bit there. But, she also told me about your
next tattoo and wanted me to check your area for size," Jaz said with a
bit of a grin on her face. I said, "What? What did she say?" Jaz said,
"She wants me to draw a new design as she was having difficulty and she
liked my work. She asked me to take stock of the canvas area and draw
up a design to send her. She asked about making it look like a nice,
clean 3D feminine muff with some pink. Can you please lay on the table
and push the front of your pants down a bit so I can, see?" I moved
around on the table and laid down. My pants were tight so I unzipped
and wiggled them down a bit as she drew the curtain around me. I was
holding my pants down a bit and she said, "That's good." And she
grabbed the top band of my pink panties and pulled them down to see.
"Oh, you are all nice and smooth, that's perfect. I was thinking we had
to shave you and deal with stubble, but you are prefect. I even like
the pink tone in your panties that I may use for the color." I wiggled
and zipped up and she said, "Don't worry, I will make it look so real
and beautiful. I am really good at the 3D stuff and I am sure you will
both love it. Please make sure you wear very loose-fitting clothes when
we have it done. I think a loose dress or skirt without panties or
underwear would be best. And don't worry, we can keep it all private
here, unless Alissa asks for different." Oh my, I was not sure what to
say. I just agreed, had a few compliments for her work and graciously
left.
On the way home, all I could think of was having to wear a dress or
skirt out for the next one. I have to be careful; will I need to do
myself up and venture out that way? If so, well, I must then, but she
was right about wearing a loose dress, it would help for comfort after.
But hopefully Alissa does not get wind of the possibility of having
this done to me for the whole shop to see. I hope that does not come
up.
I made it home and showed off the tattoo to Alissa, she LOVED it, it
was feminine and a big move for me. I was nervous for the kids to see,
or anyone so I tried my best to hide it. Alissa was actually glad it
was smaller as she did not think it would be that bright with the extra
red. Alissa told me to go upstairs and change. There on my stool was a
new outfit. Black lace matching bra and panty set, a little black
pleated mini and a sheer black blouse with my mascara, new earrings and
lipstick. I quickly let my hair down and got dressed. The top was
completely see-through, but that was the idea. My bra looks so nice
under it, so feminine, I loved the look. I applied my lipstick and
mascara as Alissa came into the bathroom.
"You look so cute in that outfit; I just love how you seem to be
filling out woman's clothes so much better these days. You getting that
tattoo made me so wet and hot thinking about the permanence of it all.
Then when I saw it, I almost came in my panties. I knew I had to fuck
you today. I love that bra too, it pushes up your little titties just
enough to show some sexy shape, I think we may need to bring this
outfit to Turks, maybe you can wear it on the plane." she stated. That
did make me squirm, I could feel my cock tighten slightly in my cage.
'Why don't we get you out of that cage while I fuck you," she said as
she went to get the key and pulled out her strap-on as well. "For being
such a good girl today and getting that beautiful tattoo, I want to
fuck you and make you come as your reward." She knelt down in front of
me, lifted my skirt and took off the cage. She said, "Oh my, it looks
like you are excited as well. This skirt looks so cute on you, I
thought you would look good in it. Don't you love the way it feels on
your skin? So light and delicate."
It did feel amazing. She started to put on the strap-on and told me to
bend over by the bed and assume the position. She came over and teased
me with it rubbing it over my ass and skirt with her hands feeling my
skirt and making me so horny. She reached and pulled up my skirt and
said, "I was dying to see how your ass looked in these new panties, and
I must say, it looks so sexy. Any guy would want to fuck you after
seeing that." She pulled my panties down to my ankles and I stepped out
of them. She lubed up her cock and told me to spread my legs, which I
did bent over on the bed. She slowly inserted her cock and then started
chatting me up. "Seeing you bent over the bed like this is so sensual,
I love that blouse, you can see your sexy bra and I am imagining what
your nipples feel like right now. Do they feel like mine?"
It felt so good going in me. She put her hands on my hips and waist as
she started fucking me, it was wonderful. I came not a minute later.
She commented "It looks like you enjoyed me holding you that way while
I fucked you. Just like a girl, I think you are coming well into
womanhood." She told me to take my blouse and bra off and lay on the
bed. She striped her blouse and bra off, took the strap-on off and put
on my panties that she just took off of me. She then and jumped on me
and told me to start sucking her nipples. She then pulled back and
started sucking mine. OMG, it felt so weird and good. It was wonderful,
my cock actually sprung up a bit, which she noticed and just let out a
little moan. She them started rubbing our nipples and it was so
wonderful. My face lit up and she knew she had taken me to a whole new
place. I started sucking them again and she came so fast. We were spent
and it was only just before dinner.
Our son was not to be home so she told me to get dressed in the same
clothes and that we would order dinner in tonight. She tossed me my
panties back and just smiled at me. I was more than happy to put them
on, but they were soaked. I got dressed and she asked me to fix up my
makeup and finish an evening look. She left the bedroom to order the
food and I sat down at the makeup table and did my thing. I did a
sensual smokey eye look and fixed my hair a bit. I looked pretty good
in the outfit and had some confidence walking around. I felt my boobs
looked good for what they were. I went downstairs and we cracked a
bottle of wine and talked in the kitchen. Alissa commented on my outfit
again and said how beautiful I looked. She came over and hugged me and
kissed me. She put her hands on my ass and it felt wonderful in my
skirt. After the kiss she looked at me and said, "You better run up and
fix your lipstick, the delivery guy will be here soon." I just looked
at her in shock and said, "Do you want me to answer the door?" She spun
and said, "Of course I do, I don't have any make up on, or as cute and
outfit. Don't worry, you look so hot. He will probably get an instant
hard-on when he sees you." I blushed and just said, "Oh stop" and went
to fix my lipstick. I also decided to quickly put on some small false
lashes to make them look a bit fuller to complete the look. I came back
and Alissa noticed my lashes right away and said, "I am glad you
thought to add the lashes, good call girl."
The delivery guy came and I nervously answered. He was a young guy and
he was staring a bit. I was trying to be a little sexy for him and
quickly checked his pants for any tenting. I could not notice in the
quick glance, but thought to myself, I wonder if I should offer to give
him a special tip? Oh no, what was I doing? As much as I wanted to, I
think I only have Alissa to lead me into that.
I brought the food into the kitchen and Alissa said, "we should have
invited him in for a tip" as she gestured with her fingers like air
quotes. I just smiled and said, "maybe next time", her eyes just stared
at me for a second and she smiled. Uh-oh, what did I just get myself
into?
Our trip time came quickly upon us. We packed for Amy, and Aaron was
only allowed two outfits because she wanted me to travel as Aaron,
there and back because of customs and identity info. She didn't want to
create a stir either way. I was fine with that. By the time of our trip
my ass had gotten a just little bit bigger and I had a little more hip
to me. My guy pants were tough to fit and felt pretty uncomfortable.
Alissa suggested I do the usual and wear my bulky guy shirts like I do
and they may cover up the new narrow of my back. And then I can wear
some unisex looking woman shorts that we had, so no one would notice.
She did say that my ass was looking really cute though and I should
show it off. She mentioned that she could not wait to see me in my new
bikinis. Okay, I was nervous and excited about our trip. And, Alissa
said she was taking care of all of the planning and schedules for our
trip and that I was on a need-to-know basis, as she expressed jokingly.
We packed and left for the trip. For traveling, I wore my guy clothes
and we found some generic looking shorts. We got in okay and took the
shuttle to to our hotel. We arrived there about 12:00 pm, with the time
change. We got our room unpacked and got settled. Alissa said she
wanted to go down to get something to eat by the pool bar and have a
walk on the beach before our mani and pedi. She said our appointment
was for 3:00, which was fine. And from now on, no more Aaron. I was
actually looking forward to this now. Alissa then said, "Okay Amy, this
entire trip I want you to get yourself changed and ready and pick out
what you want to wear. I want to see how you do with getting your
outfits together for the functions and bringing it all together. I will
help you of course, but I want to see how you do."
"What do you want to do for now? We could wear shorts and crop tops for
this or even our bathing suits and cover ups, or a cute sundress. what
do you want to do?" I said, "how about a sundress, with our sun hats,
and sunglasses" She responded "great choice Amy, let's get dressed." We
left me cage at home, but Alissa pulled out a box of the tape things to
pull my cock back and hide my manhood. She handed me the box and said,
"make sure you wear these all the time when we are out. You will need
to put some in your purse if you need to change them." We both got
dressed and she had me do some light makeup for her and for me too. we
put on some of our new flat sandals, grabbed our purses and hats and
went to the pool restaurant to get some food. It was awesome, I loved
the guys looking at me with that male gaze and I know Alissa was
enjoying it too. I'm not sure if they were looking at me really because
Alissa was so beautiful, but it felt good anyway. She said I looked
amazing and no one would even think I was a guy, she said she was so
proud and hot as well. She mentioned that we may be running to our room
here and there to keep her satisfied. I excitedly agreed to do whatever
she needed.
We had a nice walk on the beach with our dresses blowing, I felt so
sexy. And made our way to the spa for 3:00. We got our manis and pedi
and decided to let each other pick out the polish. I selected a coral
bright red for her and she picked a coral bright pink for me. We had a
couple of drinks at lunch and were a bit giggly but it was great. I
felt so feminine and my nails turned out great. On the way-out Alissa
asked if we should ask about a massage and the masseuse staff, which I
quickly agreed to do. When the spa attendant Maria, suggested we book
with Carlos she said with a smile "you will not be disappointed. And
NO, he is not married and does not have a girlfriend", we all laughed.
They only did single massages so we booked back-to-back times for the
day after next.
We went for an early dinner and had watched the sunset by the pool with
another drink or two. We were both pretty tired by 10 and decided to
turn in. We went back to our room and got ready for bed. I selected a
pink, to match my nails, silk babydoll and matching panties. Alissa
mentioned how cute I looked and said I was getting better with my color
coordination. She wore a black long nightshirt and we passed out
quickly.
Day 2 and we woke to bright sunshine from a great sleep. Alissa said,
"today we are going to have a light breakfast and go lounge on the
beach and start working on our tans. I want to get one of the beach
cabanas early so we don't have to lie on the sand. We will be able to
get service from them as well and have the ocean to cool us off. At
3:00pm we have our first diving session with a small group to go to one
of the 3 areas we will dive while on our trip.
I had a shower, grabbed a new strip to hold my cock back and found a
new bikini while Alissa jumped in the shower. I selected my white one
with the bright pink edging. The bottom was a full back and the top
helped with a bit of push up. I grabbed a white pullover that was like
a loose crocheted look and my big sun hat. I did a light makeup and was
ready for Alissa. She came out and saw me. "Oh god Amy, take that cover
off and show me what you got!" I peeled it off and did a little spin
for her. She was just staring and said how good I looked. She grabbed
her phone and snapped a few pictures. She then went and got ready. She
had her black bikini, which she looked so amazing!! We both scrambled
to get a few bracelets and she pulled out my anklet and put it on me.
She said I should keep that on the whole trip, which I gladly agreed.
She said my suit even matched my tattoo! She asked me to do a light
makeup for her and we both applied lotion to each other. We then made
our way down to the cabana on the beach. Here we were, two girls out on
the beach, dipping in the water to keep cool with admiring eyes on us
every time we went down to the water. There were not many people on the
beach, but I tried to flaunt a bit, but Alissa was the master. She was
drawing so much attention, but she was so gorgeous! We had lunch
ordered from the servers and also had a few drinks.
I was suntanning my back, face down on the lounger fading in and out of
a nap and Alissa said I looked so cute with my suit and ass and
delicate curves. She was so impressed how feminine I looked. I just
thanked her as usual, but I knew she was getting horny. All of a sudden
I hear a familiar voice say "Alissa, is that you? she answered, "OMG
Roger, what are you doing here?" It was Roger from over a couple of
blocks from our house. He was our daughter's soccer coach and a distant
friend to us both. I was not sure what to do and faked that I was
sleeping. I hope it did not seem rude but I could not let Roger know
who I was. I didn't hear his ask her, but I think Roger motioned to
gesture who was next to her because I just heard Alissa say "oh that's
my girlfriend Amy", with a bit of a whisper, "we needed a girl's week
away." He asked how Aaron was and she just politely said, "he is good."
He said he was there as he brought his daughter and her friend for a
vacation. Roger's wife passed a few years back from a bad car accident.
He was just happy to get away. They had a bit more chit-chat and Roger
left.
Alissa turned to me and said, "nice job pretending to be sleeping,"
with a smile. "I think that was a good move." Although you didn't see
Roger, he was having a hard time taking his eyes off of your ass as we
were talking. I think you would have been quite impressed by his cock
in his swim trunks Amy. It looked very nice as far as I could tell. I
guess he is at the resort here, but it's so big, I'm sure we won't
worry about seeing him again." She said all of the casually, like we
were girlfriends and matter-of-factly.
At 2:00 we decided to go up to get changed for our scuba session. I had
some great tan lines going and Alissa was lifting my straps and suit
checking it all out. She squealed when she saw my tan lines from my
top. "Amy, you are going to have to even those out, they might last for
a long time. I'm so excited to be able to see you in your scuba outfit
and we can finally dive together again." We went to the room and
changed fast. Alissa helped me with my suit and I did the same for her.
We were hot looking. Alissa said, "I hope there are a few guys in our
group to tease. I can't believe how your ass is looking in your suits,
it's really turning me on. I can't wait to fuck it later." That's all I
needed to hear from her. I think I had some shape going from the
hormones as I mentioned. Not a lot, but now it was enough to notice.
On the walk to the diving area, I told Alissa that I seem to be
smelling a lot better and it may sound crazy, but it seems like I can
actually smell guys. She stopped and grabbed my arm and said, "Amy,
that's the hormones. You are probably smelling what I smell. Did you
smell Roger today?" I said I did, and said I think he smelt pretty
good. "He did" she exclaimed "Amy, this is so exciting. Just wait for
the next cock you suck; I think you may really enjoy it. It could go
either way but I want to find out soon. " We found the place to go and
found our guide. All of the tanks and equipment were ready. I had a
hard time with mine because of my nails and I was trying so hard not to
chip them, but we got it all done. One of the guides Ken, got nice and
close to me to help me with the suit and he brushed my "breast", I felt
my nipple really twinge and sent a quick shiver down my spine, in a
good way. Alissa noticed and just smiled. She then came over and said,
"Ken looks like he could use a tip" we both laughed. We had a great
time and Alissa was teasing me and touching my ass in my suit
underwater and being very playful and loving. It was awesome.
We got back to our room about 6:00 and decided to have a shower and go
for dinner. I ended up wearing my short new black wrap dress with the
red hearts and open toed wedges. Alissa wore a striped sundress that
was a little more flared than mine with flat dressy sandals, she looks
amazing. I did both of our makeup, I put my hair up from the sides with
a small barrette and we grabbed our purses and went for dinner. We
decided to have a drink at the bar before dinner.
As we were sitting there and pretty close to each other, I got a tap on
my shoulder. I quickly turned around and it was Roger! I turned back
and looked at Alissa with a frightened look and she said, "Oh hi Roger,
what are you doing here?" He said, "I am meeting my daughter in about
15 minutes. I thought I recognized that tattoo from earlier on the
beach" while luring at me with a puzzled look. Alissa quickly jumped
in, "Roger, this is my friend Amy." He did not respond and was still
staring at me. It was pretty awkward, but then he said in a inquisitive
voice, "Aaron? Is that you?" I was frozen and not sure what to say. he
then added "Please tell me that is you Aaron, you look beautiful!"
Well, when he says it that way, I had to say "yes, it is me Aaron,
well, please call me Amy." His face lit up, and he said, "Wow you look
simply amazing. Look at you. Are you transitioning? I'm fascinated by
the Transgender community. Are you transitioning Amy?" I was not sure
what to say. But then I said, "Not transitioning but I love being one
of the girls and we will see where it takes us. I am not out; we just
spend time alone like this trip to experiment with a few things. I hope
you can keep that between us." "Absolutely," he said with some
excitement. This whole time he was practically undressing me with his
eyes and staring. But he did smell good and I made sure I was able to
get a glimpse of how he was in his pants and he looked like he actually
had a hard-on. He excused himself as his daughter and friend caught his
attention to join them across the bar. Once he was gone Alissa said to
me "It looks like the cat is out of the bag Amy. I was not sure what to
say or do. I was going to say you were Aaron's cousin or sister but it
all happened too fast. You said it in a good way. But I am not sure if
you noticed, but his cock seemed to grow pretty quick in his pants
after he discovered you were Aaron. I don't know how he walked across
the restaurant like that." we both chuckled.
She then said, "I have to ask, but did it run through your mind
wondering what he would taste like?" I looked her in the eye and said,
"Absolutely. He smelt good and I felt like reaching out and grabbing
his cock right in his pants right here." Oh my" she said, "you are one
dirty girl. I would have liked to see that. Maybe we should ask him to
our room for a nightcap tonight and you can find out." I was not sure
about that because we knew him and he was our neighbor and kids'
friends. Alissa was quick to remind me that it was for both of us and
sometimes it's better to trust the guys you know.
We had dinner and chatted more about it. It seemed we were talking
about clothes, fashion makeup and guys, it was a very good evening. I
guess after a few drinks I was open to her suggestion to talk to Roger
some more and see where it goes. On our way-out Roger came running over
to catch us and asked if we wanted to have a nightcap at the bar. We
said we were tired but could maybe do one drink. He asked us to grab a
stool and give him a few minutes to send off his daughter and friend.
Roger came back a minute later and joined us as we were getting our
first round. He pulled up a stool between us and we chatted for some
time. We both keep glancing at his hard on, but he was obviously
looking more at me. Alissa kept gesturing me to grab his cock, like a
little game. We were a little tipsy now and we were giggling a bit.
Roger was pressing us on why we were laughing and a few jokes were
getting a bit sexual. I had a couple more drinks at this time and Roger
caught me checking out his bulge. There was a break in the conversation
and Roger sensed something and asked, "Is everything okay Amy?" All of
a sudden, I just said, "Alissa wants me to grab your cock and see what
happens." Alissa went red in the face, "I do not" she exclaimed. We
went back and forth with some comments to each other and he put his
hands up and said, "Stop girls! Why don't we go to your room and you
can grab it all you want Amy!" We both looked at each other and I said,
"Okay Roger, let's go." He was shocked and thought we were joking. Once
he realized we were getting up, and serious, he just said, "okay, what
the hell, you two are a lot of fun. And Amy, truth be known that trans,
and more specifically you right now turn me on." Alissa then said, "me
too Roger." I tried to put on my sexy walk in my heels and think it
worked. Roger was grabbing my ass as he walked behind us. He put his
hands around my hips once and mimicked my walk behind me, it was quite
sensual.
We got into the elevator and he went in first and I was in the middle
and Alissa pushed the buttons. We were laughing and giggling. Roger
reached out, grabbed my waist and pulled me into him from the back.
Wow, what a feeling, here was this strong guy pulling me in and his
cock was rock hard in his pants. I could feel it against my ass and I
wiggled a bit when Alissa wasn't looking. His hands were on my hips and
holding me like Alissa does when she fucks me. I couldn't help but
think what it would be like to bend over and have him fuck me the same.
Although, the fact that I was making him hard was more than enough for
me. It was clear he wanted me over Alissa, probably because I was a guy
because Alissa was so much sexier and more sensual than me as a woman,
hands down. I tried to stand firm in my heels making my legs look long
and hoping my ass looked good. I loved the loose dress I had and the
flirty feeling on my thighs. We made it to the room.
We decided to make a drink and have some more small talk. I was up and
down a couple of times from the couch and edge of the bed trying to be
as sexy as I could for Roger. Roger was in the single couch seat in our
room. It was a little lower than the bed and I thought it might be good
to suck him from the chair. At this point I was dying to have him in my
mouth. And Alissa was giving me the eyes, as if to say "c'mon girl,
what are you waiting for?" I went into the bathroom, had a quick pee,
put my hair up in a ponytail and touched up my mascara and lipstick. I
came out an asked Roger to stand up, which he quickly did. I went
close, put my hands on his shoulders and started feeling his chest,
arms, shoulders and back. I slid my hands from his shoulders and
reached down for his cock. I started to feel his cock in his pants and
it was growing, it felt so good in my hands and I felt pretty and
powerful.
I looked up at him and said, "Roger, I'd like to cap off this night
with your gorgeous cock cumming in my mouth while Alissa watches. Can I
have the pleasure of giving you a blow job?" Roger said, "yes, please
Amy, that will be a good start and you have been making me horny since
I first saw you on the beach. I was hoping I could fuck you, but a
blowjob would be nice." I smiled, unzipped his pants and let them fall
to the floor. I put my hands in his underwear band and pulled them down
as I dropped to my knees. His beautiful cock popped out into my face
and I looked up and smiled at him. He then pulled out his phone and
started taking a few pictures of me while I started to lick and admire
it. It was big and beautiful and he smelled so good, it made my cock
twitch. I was in the moment and didn't really care about the pictures.
I looked over at Alissa and she had her panties off and dress up
playing with herself. She was also pinching her nipples and really into
this. I moved a bit so she had a better view of me.
Roger was taking a few pictures of her as well but we did not seem to
really think about it. I think I was getting good at sucking cocks, or
so I thought, and Roger came in about 15 minutes. I felt him swell and
he started to explode in my mouth as I tried to pull back a bit. I
chocked a bit, he just smiled when I looked at him doing this. I then
pulled him back just out of my mouth so Alissa could see him squirting
in my mouth and I was trying to let it pool before swallowing. I made
sure I got all of his cum so I could taste and gulp it. It was so
delicious, and I did cum in my panties at the same time as I felt his
cock pulsing cum in me and I think Alissa did as well when she saw his
cum going into my mouth. I was careful to get the few leaks and drips
and sucked my fingers dry then gave him a good cleaning as he was
softening. I said, "Thank you Roger, I hope you approve." Roger looked
down at me and said, "Amy, that was the best blowjob I have ever had. I
think we are going to be doing this again real soon." I was not sure
what to say, I was not thinking long term. He pulled up his pants and
underwear and reached down and lifted me to stand. He kissed me on the
lips and wrapped his arms around me. He then said, "Amy, I think you
should be a girl full time, you are so feminine, soft and you know how
to suck a cock, you didn't have to spit-lube me once. Let's keep in
touch and see how we can mingle in the future. I thanked him again,
with hug, and he left. I did like how he ran his hands across my back
and felt my bra as we hugged. It was a little thing but it felt sensual
to me.
Alissa grabbed my hand after the door closed spun me around and started
kissing me wildly. I could feel our boobs touching and my nipples and
cock were twinging. She then led me to the bed and pushed me back on
it. "You smell like cock and taste like cum." I just smiled and she
said, "such a good girl, I love you, you make me proud. How did he
taste? I noticed he had a lot of cum." I replied "Alissa, he tasted so
good, I can't tell you. Definitely the best I have had and he smelt so
good too. He was a little musty but it was almost addictive, I wanted
to smell him some more. Do you think it's the hormones? He did have a
lot of cum and I have to say I did feel like a little dirty girl not
wanting to waste a drop. I can still taste him." as I licked my lips
and teeth. She took off her dress and quickly shed her bra and leaned
down and told me to get sucking. Her boobs felt so big and her nipples
were huge. She leaned into it and came two minutes later. She then
moved up on me and told me to eat her wetness and suck her dry. OMG she
tasted like candy. We finished up washed, got our makeup off and got
dressed for bed. I wore a baby blue satin top and short set with white
satin bikinis. I was thinking about Roger's cock a lot and what we had
done. In bed I said I was thinking about it to Alissa and she asked
what part. I said, "the taste, his smell and seeing the smile on his
face when he was cumming, and yours, I guess all of it. I am afraid I
am wishing I had some of his cum right now in my mouth." She just
smiled and replied "oh goodie, that was so erotic for me too and I was
wondering how we could do that again. He looked so into you and I am
sure he would have stayed to cum again. I think he has quite a thing
for TVs. I'm sure he would really love you in your cute pajamas. I bet
you he's going through his pictures right now."
Then it struck me, oh no, he has pictures of me and us. What if someone
else finds out. Alissa said, "don't worry, I trust him, I don't think
he will be that way." We were both spent and had a good sleep.
The next day Alissa said it was beach and massage day. She thought we
can have a few drinks on the beach and work on our tans and finish with
a nice relaxing masse. It sounded great. I went to shower first. I
stopped and plucked a few eyebrows, Alissa yelled in asking what I was
doing. I told her I was plucking a few strays and she urged me to get
in the shower fast so we can get the good beach chairs. I showered and
finished up. on the way out of the bathroom Alissa said, "I'm going to
wear my flowery tanga and I suggest you wear your black tanga." okay, I
thought. I was nervous about letting my butt hang out, but I have to do
it sometime. The top was a triangle style with very small strings. I
put a new sticker on for my cock and got dressed in my new bikini. She
came out as I was checking myself out in the mirror. "OMG you look
amazing! I told you how awesome that looked in the store, you actually
seem to fill it out just a bit better now, wow. You just watch how many
guys will be checking us out." I put my hair up and some small hoops
for earrings. I wore a beige mesh coverup, hat and beige and white flat
sandals with some really nice beading on them. Alissa looked so good in
her tanga, she took the white coverup and some white 2" wedge sandals.
I did some makeup for both of and, we loaded the beach bag and went
down to get our seats. We decided to order breakfast lunch to our beach
chairs. I definitely need to work on my tan lines as i had some lines
from my other suit, which was a fuller back. The top fit me good,
although I did need nipple covers as they were really sticking out and
hard the last few days.
On the way Alissa said, " when you were in the shower, I called the
salon to make an appointment. Tomorrow after a dive, we will be going
for a mani, pedi to change our polish and we will also be getting our
hair and makeup done. I figured we would go to the one of the fancy
restaurants tomorrow night and get all dolled up for it. I said, "that
sounds like a great idea. I've been dying to wear one of my nice
dresses and heels." She said, " I also asked them to do our brows as I
figured we may as well have them do it rather than ourselves. We are
here to be pampered, aren't we?"
We were at the beach, it was beautiful. We had some food and drinks.
Alissa excused herself to go to the bathroom by the pool area. She was
gone a really long time. I was starting to worry and hoped she was
okay. She finally came bouncing back and was all giggles. You will
never guess who I just had a quick drink with at the bar by the after I
went to the bathroom. 'Who?" I said, she quickly blurted out "Roger, of
course. We had a nice little chat. You should have seen him in his
tight boxer trunks, it probably would have given you some cravings of
some sort. He was asking about us so I told him we were really just
having fun with your sexuality and I was loving it and helping wherever
I could." I asked, "well, what else did you say or talk about? Did he
say anything about me?" "Glad you asked, she said. He said you looked
very cute and feminine and really turned him on. He said you gave him
the best blowjob he has ever had. I told him you REALLY enjoyed his
cock and you commented on how good his cum was." "OMG Alissa, you DID
NOT! I said, she just smiled and said, "of course I did" with a big
smile. "I wanted to see if his cock started to get hard, and it did. He
really likes you, Amy. I asked if you could suck it again", and we
laughed as he said, "I was just going to ask you that Alissa." "I also
told him about our arrangement and that I was present at the time.
Normally, I would expect a guy to ask me to be part of it, which he
didn't, so I know he is really into you. Anyway, I told him we can text
and will be on point for your planning." I was happy with that and was
thinking more about sucking him off again rather than anything else. I
asked Alissa "okay when?" She said, "Not so fast Amy, you dirty little
slut, I suggested tomorrow evening after dinner." I responded "great,
that sounds wonderful. What will I wear? I want to be really cute for
him." Then I remembered Alissa booked a salon appointment to get all
dolled with her and then a nice dinner. "I was thinking that my short
black wrap dress with the hearts would be perfect for tomorrow." Alissa
responded "that is a great choice, Amy. That dress looks so cute on you
and now with a tan, you will look amazing. Maybe a red polish will do
you well. Did we bring your red panty and bra set? Imagine how hard
Roger would be with you in your bra and panties, matching nail polish
and matching lips. It might be a 2-load night. Will you take off your
dress for him?" I was not sure what to say and was thinking. It may be
exciting, but I don't want him thinking he can fuck me. But I was
getting excited already.
We finished the day with a nice massage back-to-back. I got to undress
and dress in the ladies change room and they gave me a pink robe. It
was quiet and no one else was the at the same time. We ended up going
one after another and I guess I was thinking more about the sure thing
with Roger, rather than trying to do something with our masseuse. He
was really not that hot, but I did like showing off my tan lines. He
did have nice strong hands.
The next day we had an early dive and I got to wear my black wetsuit.
It seemed to show my little curves best, but Alissa loved the way they
made my ass look. Alissa looked stunning as usual in her long version,
her curves and body were just amazing. I received nice glances, mostly
the male gaze and the guys, but Alissa, everyone looked at her, even
the woman. She had an amazing body and looked so gorgeous. People did
tend to actually stare at her, she had that affect.
We had the appointment for the salon at 5:00, so we decided to go for a
walk around and a game of lawn chess. We went back, showered and
changed. I wore a cute little white flared pleated mini and a camel-
colored light crocheted top. I wore a lacy white bra and matching white
satin and lace string bikini panties. I picked out some beige 1.5" open
toed sandals and a white purse. Alissa wore an amazing blue jumper and
looked fabulous. She asked me to do a little spin and said I looked
perfect! She loved my little skirt and said in the right light you can
see the outline of my panties and said how hot it was. She came over
and ran her hand up my ass under my skirt and felt my pantries, it felt
so good. I did a light makeup for both of us and we went for a walk.
Everyone was looking at us, I loved the attention, I was getting used
to this. We found the chess game and started a game. I didn't realize
it was so windy and Alissa was getting turned on by the little teases
of my panties she was getting with the odd gust. We ended up string and
have a drink rather than finish the game. It kept my skirt down as
well. I had my hair up so it was off my back and with my fancy
sunglasses I felt so cute and feminine, it was awesome. Alissa kept
complimenting me that this was the ultimate outfit as I looked so cute.
Alissa said, "Well Amy, it looks as if you are playing the part quite
well. Here we are outside sitting by the bar, you all pretty in your
cute outfit. You didn't even think about what you were going to wear,
not asking for my approval and having some feminine confidence. It's
sooo sexy. You have no fear. Maybe it's your A cup breasts and your
beautiful butt that helps as well. Since you have some curves, the
clothes fit better, you look sexy and people notice you. I am in awe of
you and your femininity and not sure if it's the hormones or really the
Amy inside. I was thinking at the salon to have your brows just cleaned
up a slight bit and get the loose ones. But if you want more, I will
leave that up to you. Having a nice shape and thinner brows can really
make you look so much more beautiful, but hard to explain to the kids.
But, so may your tans lines and A cups. I think I am going to have to
start rubbing our nipples more in the future. My panties are so wet
watching and being with you. I'm debating just taking them off or
putting on a pad. I won't make you wear them because they are dark and
I don't want to ruin your cute outfit. Seeing the outline of your white
panties through that skirt is quite erotic for me, and for everyone
else, I am sure." I was not sure what to say, Alissa had her soft hand
on my leg just going up my skirt a bit.
We went back to the room and she asked if I would stay dressed with
what I had on and maybe put on a 4' white and brown wedge, which I
agreed. She said, "Please keep it on since you look so good. You can
wear your other dress maybe tomorrow. Roger will freak out when he sees
you, it's making me so wet thinking about it. And besides I was just
thinking a while ago that it might be nice to have the salon do your
nails in a white polish today for the outfit, what do you think?" She
undressed in the room jumped on the bed and had me suck her nipples to
a quick orgasm. My cock was twitching as it was tied back. She said,
"Don't worry, I'm sure you will be coming in your panties tonight when
Roger comes in your mouth. You are going to be one lucky girl tonight.
Let's not miss our salon appointment so we can attract some attention
tonight and I want you to feel pretty tonight as I take my wife out for
dinner."
She cleaned up and put on a gorgeous sun dress with some casual strappy
heels. She looked wonderful. I straightened my clothes, fixed my hair
and we went to the salon. She was teasing me and putting her hand up my
skirt on the way, it was so playful and I enjoyed it. People must have
now thought we were lesbians, which Alissa did not mind one bit. She
was so confident and carried herself so well. I think it's what
originally attracted me to her when we first met.
We arrived at the salon. Apparently, Alissa ordered the "Date Night"
package. We had our toes and nails done, then our brows were touched
up. I chickened out of having them waxed and fully shaped, but they did
clean them up so they were clean and possibly a bit more feminine. We
then had our makeup done, with some great false lashes and then our
hair styled. OMG, it was wonderful, they did such a nice job on us, I
felt so pretty. I even felt special when they put a cute pink full
smock on us to make sure we didn't get anything on our clothes. I just
thought, if this is what girls get to do, then sign me up. I could tell
Alissa was squirming and getting all wet as we were getting worked on.
She leaned in and whispered to me "I really don't know why this gets me
so wet seeing you like a girlfriend with me, but it's wonderful. We
should have been doing this years and years ago. My panties are
completely soaked right now, but I brought another pair because I know
how well you go with your outfit. OMG I can't wait until Roger sees you
tonight." I just smiled and "'me too!"
The girls put my hair back in a broad over some of the long, it was so
pretty. I changed to a pair of diamond studs, which this style really
seemed to show off. The focus was on my lashes and otherwise light
makeup and pink lipstick that seemed to go so well with everything. I
felt so pretty and thought Roger would be in for a surprise. Alissa
looked beautiful, she looked so classy and a natural beauty. We hugged
after and it was a long one, we were both so emotional for some reason.
I did notice my boobs on hers when we hugged, it was pretty nice and my
nipples twinged a bit. Oh no, I thought, can you see my nipples? I had
to ask Alissa and she said I was fine, then she asked about hers, which
I said the same. It was a nice moment actually.
We had a nice dinner. We both freshened up our makeup in the washroom
after and went for a drink in the bar where Roger was going to meet us.
After a couple of drinks, Roger came up behind us by putting his hand
gently on my shoulder and keeping it there as he popped in between us
to say hi. He said how beautiful we looked and asked me to stand and
let him see. I coyly got up and gave him a quick spin. My skirt flared
and I embarrassingly pushed it back down. I hoped no one in the bar saw
anything, Roger was too close to see up my skirt. Then I thought, I
actually hoped someone did see my panties. I have to say that my outfit
was sexy and I felt so sexy in it.
Roger pulled up a stool between us again, had a drink as we chatted. He
put his hand on my thigh after 5-10 minutes, I must say, it did not
feel bad. His hand was warm and I felt a little dirty or submissive.
Alissa noticed and gave me a brow raise and a cute smirk. She gestured
her eyes for me to look at Rogers crotch, OMG he had a huge hard on. I
wanted so bad to rub it through his pants and get a feel, but then
thought, how are we going to get him out of here without anyone seeing
him? I guess that was a guy problem for him to deal with.
We finished our drinks and decided to head out to our room. We fumbled
a bit and he was all over me. He was holding my hand, my ass, touching
my skirt and leg..I think he was ready!!! We got to our room and
grabbed a drink from the bar, sat down and had a few more laughs. I was
more playful with him, sitting on his crotch sexily and feeling his
hard on on my ass. I teased him a little rubbing his cock in his pants
as Alissa encouraged and smiled. When I started this, she quickly got
up and went to get her dildo. She came back, sat down and immediately
put it in her pussy and started rubbing her nipples inside her top. She
then was back and forth rubbing her clit. Roger noticed this and knew
it was time. He stood up from the couch and I unbuttoned his belt,
undid his zipper and slid down his pants. I took them right down and he
stepped out of them and I stayed on my knees. I turned a little so
Alissa could see it best. He came at me with his cock, I took it by
hand to start, as I looked up at his thanking his for letting play with
him tonight. I then started to suck him, he was so hard and delicious.
I was almost able to get his whole cock in my mouth this time without
gagging, which I was surprised. He smelt so good and tasted even
better. The sweet taste of his precum made me want more. I sucked him
for 5-10 minutes and felt him swell and ready to explode. I moved the
tip of his cock to my lips and held my head up so I could catch every
drop and pool it in my mouth. He kept coming and my mouth was pretty
full. I made sure Alissa could see my full mouth before I swallowed all
of it. I lovingly swallowed all of with a big smile. It was so
delicious and great to have in one big gulp. Alissa's eyes bugged out a
bit she smiled and it looked like she came. I noticed she just slowed
the rubbing of her clit and looked like she was in another world
cumming. I came instantly in my panties when Roger's cock started
squirting in my mouth. I made sure not to move much and maybe keep it
to myself so Roger got the most of his excitement.
I looked up at Roger and "Thank you. that was awesome, I love your
cum."Roger replied "Amy, you are such a great cocksucker and a sexy
girl. Your outfit is beautiful and you look stunning today. I really do
think you should dress like this full time, with a smirk to Alissa.
Maybe one day I can see your beautiful titties." Okay he had me again.
He was putting on his underwear and I said, "well maybe I can take my
blouse off and you can see me in my bra if I can eat your cum again."
Alissa said, "oh that's a great idea Amy, Roger, why don't you sit and
get some energy back and have a drink or two. I'll order some room
service snacks." Great idea Alissa, said Roger. That would be my
pleasure Amy" as he put on his underwear and went to the bathroom.
Alissa said to me once he was in the bathroom, "that was so awesome
Amy. The way you showed me his cum, it sent me over the top, it was so
erotic for me. What was really nice was your smile after you swallowed
it, it seemed like you enjoyed that more than anything. Will you please
do that again for me? I think Roger will cum pretty fast looking down
at you in your bra and white skirt, get ready for it." I said, "oh I so
will be ready Alissa, it was really good. Sorry to ask him to stay but
I thought, since we have him and I feel very pretty today." I spoke.
She responded saying, "it was absolutely the right thing to do, you do
look amazing and we are here for the fun, and I think it we are having
fun, right? And if you didn't ask him, I would have. It's better it
came from you, that worked out perfectly."
We had a few drinks and I ended up doing a few spins for Roger so he
could finally see my panties and up my skirt. I did notice he snapped a
few pictures all along that way too. We were all a little tipsy and I
didn't care.
We finally got back down to business and I was ready for him again. I
stood up from the couch and sexily took off my top. My bra was a Simon
Perle set with matching bikinis. (I left my skirt on) The bra was a
combination lace and white silk plunge bra. He just stared for a minute
and so did Alissa. He quickly adjusted his cock in his pants and I knew
he was growing again. OMG did that make me feel good. I suddenly felt
my nipples twinge and my cock. He was getting hard just by looking at
me in my bra. He stared for a minute then stood up, took his pants and
boxers off and I just dropped to my knees in front of him, in clear
view for Alissa. With a big smile over at Alissa I started stroking his
hard cock and she just smiled. This time I just started sucking and
when I glanced at Alissa, she was playing with her nipples in her bra.
Roger was looking down and playing with my bra straps on my shoulders
and trying to lean down a bit to play with my boobs but he quickly
noticed it affect the blowjob so he stopped. It felt good to have his
hands on my shoulders and in my hair, added to the moment for me. He
smelt so good too, especially after coming already. I did the same
thing for Alissa and held his cum in my mouth and she just said, "OMG"
when I swallowed. I did also cum again in my panties, but she didn't.
Roger tasted so good again and I went in to dry and suck every bit of
his scent off his cock and said a polite "thank you" to Roger when I
finished. It was wonderful. I got up and kissed Roger and he held me in
my bra and skirt and rubbed his hands all over my backside. It was a
quick kiss to say thank you, it was nice. I grabbed my top and put it
back on while Roger got his stuff together, dressed and headed out to
see his daughter back in his room.
After we closed the hotel door, Alissa started on me. She was so
excited and going a thousand miles an hour, said, "wow Amy that was
incredible, you did such a great job. I came twice, you looked
beautiful and played the part so well. I think Roger really likes you.
Sucking him with your top off was so sexy, your A cups look so good in
that bra, I actually had no idea. She proceeded to remove my top while
chatting. Did they grow some more? I love what they did at the salon,
our nails were great and the way they did your hair its stunning and
perfect for blowjobs I must say. I think we need to do it this way more
often. How did you feel? did you like it was it good for you?" yes,
thanks Alissa it was awesome. I loved his cum and twice in one night
was fantastic. I loved what the salon did for us and do love my hair. I
felt really pretty tonight, but when I saw his reaction after taking my
top off, well, that was over the top. There was this look of lust in
his eyes that I had never experienced before and it made me feel like
such a woman, OMG it was divine, I can't explain it, but it felt so
good." "It looks like you are more feminine that you think Amy. These
are normally feelings many girls get in the moment. My nipples ache
sometimes when this happens." I said, "Mine too, they were actually
twitching and I thought how nice it may be to have them sucked on while
I was sucking his cock." Alissa took my bra off and pushed me on the
bed, she said, "now, sit back and enjoy as I can take care of that for
you." She started sucking my nipples and then took her top and bra off.
I can't fully explain what it felt like, but I felt like I was in a
different world. We sucked nipples and rubber them together. Alissa
came so hard. She pulled off her panties and came and sat on my face
and told me to lick her dry. OMG it was so erotic, she was so wet and
sloppy, and tasted delicious. She said, "does it taste as good as
Roger's cum?" I just moaned with a yes. She said, "good, I think you
need to smell more like pussy, as she grinned. I'm sure your panties
are so very wet with your cum since sucking off Roger. Imagine if you
had a cute little pussy like mine leaking erotic feminine juices, mmm,
when you are done here, I am going to get the strap-on and fuck you.
After your performance tonight you deserve to be fucked to finish off
the evening, like a good girl. I'm going to have you lick your cum from
your panties while I fuck you. Then while you cum, you will catch it
and lick your cum from your hands. That is going to make me so hot.
There is something special watching you eat cum. Imagine, you are going
to taste like Roger, yourself and my pussy. I can't wait to kiss you
after." The rest of the night, went just like that, it was wonderful.
We kissed after and rubbed nipples; it was so erotic. I had no idea
Alissa had these great ideas and loved to control her sex so much. It
was heaven. My holiday as Amy was more than I expected, I enjoyed being
Amy more than I thought.
We had a couple of quiet nights after that and finished up nice tans on
the beach. We visited the salon one more time and had a polish change.
Roger left the next day anyway after that last blowjob. Alissa said,
"don't worry, I did have a chat with Roger remember. He is only a few
blocks from us and I said we will have to schedule regular session with
him, he agreed. And I am sure he would love to see you in your little
white skirt again." Oh no, I thought. That sounds so great, but makes
me so nervous as well. I was hoping to be able to hide my femininity
and I sensed this might not be the direction Alissa wanted, although
she was fully supportive to help Amy be hidden. We will have to see
what she is planning when we get home. But I have to admit, I am
actually craving to taste and swallow his cum as soon as I can.