Weekend
Getaway Turned Fifty Shades
My
friend, Nick, a well established businessman in town, would often take me out
to beautiful restaurants and treat me to lavish nights out. We always had such a great time together
which would often end with me spending the night at his five bed/five bath
mansion, overlooking the Strip.
One
morning I get a text from him, asking me if I’d
like to go on a weekend getaway with him to his second home in Palm
Springs. He further explained that his
other place was just down the road from a few wine tasting restaurants and we
would be meeting a few other couples there for a fun, wine tasting weekend.
How
could a girl so no to that?
“Of course,” I replied.
He replied back with “Wonderful” and told me to pack for a leisure
weekend of wine tasting and site seeing.
Also reminding me, since I always wear heels, that it would be best to
bring shoes for walking on grass and uneven yards.
I
replied with a “wink” and told him I couldn’t wait
for the weekend to arrive.
So
as every trans woman does, I packed way too much. I brought a few of my favorite summer
dresses, sweater dresses, and my favorite skinny jeans. I picked through my shoe closet and pulled
out a few pairs of wedges and one pair of flats. Not that I was planning on wearing the flats
but I figured I’d take them with me anyway.
So
the weekend had arrived and he picked me up as usual in his new Rover. He just started laughing at me when he saw me
dragging my huge suitcase out of my townhouse and to the curb. He hopped out and said while laughing, “I’m surprised you’re only bringing one suitcase. The trip is a whole 2.5 days!”
I
just stuck my tongue out at him in response.
After giving him a big hug, we both hopped in his Rover and headed
west. We had a fun and leisure drive
with fun filled conversation and played a few road travel games to pass the
time. Upon arriving at his vacation
home, we pulled into a beautiful ranch style home overlooking a plush green
golf course. It was starting to get dark
but the solar powered lights lining the driveway and back yard made it all look
so luxurious.
After
dropping off our luggage in his house, I quickly freshened up in one of the
marble tiled bathrooms, and threw on one of my favorite sweater dresses. The air had cooled a bit outside so I thought
that my red knit dress would be perfect for a quick dinner out. He said that we would just grab a quick
dinner tonight and retreat back to his place for a night cap of wine
after.
After
dinner, we took a short walk down Palm Canyon Drive to stretch our legs a bit
from the long drive. And walk off some
of those calories we just ate from our meals and dessert. Upon returning to his golf community house,
he started a fire in the main living room and I slipped into a long black silk
gown. It was such a romantic evening,
sipping wine by the fire place, snuggling in his arms, and kissing like we were
teenagers. After a short while, I could
feel his massive erection through is plaid pajama pants and knew he was ready
to collect his price. I slowly reached
down and unbuttoned the front of his pants and softly reached in to caress his
engorged head. He was so hard I thought
he was going to exploded right there. He
wrapped his arms around me and slowly lowered me to the floor, just in front of
the crackling fire. It was such a hot
moment between us and the fire was making it even hotter.
I
quickly reached down and pushed his pants down with my hands and then pushed
them further to his ankles with my feet.
He continued to caress my breasts through my silk night gown and then
pulled the spaghetti straps from my gown down off my shoulders.
We
continued kissing and massaging each other.
With his assistance, we reached down and lifted up my long silk gown to
expose my black lace thong I was wearing.
He savagely removed my panties and stated “You
won’t be needing these anymore.”
“Where’s your lube baby?” He whispered.
“In my purse hunny,” I replied.
With
my legs still wrapped around him, we rolled onto our sides to retrieve my purse
setting on the floor next to the couch.
I quickly grabbed the bottle and squirted some KY onto his throbbing
cock. He slowly lifted my left leg up
and onto his shoulder, with my right leg remaining wrapped around his
waist. He had put me into such a
submissive position and he was about to take complete control of my entire
trans existence. With one quick thrust,
he jolted into me and I screamed with equal pleasure and pain.
I
reached down to grab his butt checks with my freshly manicured hands and could
see my red painted toes nails twinkling from the fire light. The moment was so surreal and I knew I was
his possess for the weekend.
He
continued jolting into me and I could feel his now full balls slapping about my
ass with every thrust.
Slap! Slap!
As he continued to possess me.
Fully knowing that soon, the fullness of his balls would be emptied
inside me. As he continued to drive me
further into the floor and kiss me with each thrust, I could feel him getting
harder and more swollen. I knew we were
both close to getting the prize we both wanted.
With
one last climatic thrust, his volcano erupted into me and I once again,
screamed in pure pleasure. He slowly
lowered my leg from his shoulder and I wrapped both legs around him. Squeezing him tightly against me and feeling
the warmth of the fire engulf our naked bodies.
His
now semi-erect cock, slowly slid out of me and I could feel some of his
volcanic lava dripping out of me. He
reached over and grabbed a few pillows and fleece blanket from the couch and
wrapped us up in it next to the fire. He
wrapped his arms around me and we fell into a deep sleep in such a romanic
setting.
The
next morning we awoke to a pile of ashes in the fire place and gave each other
a quick morning kiss. I hopped up and
wrapped the blanket around me, leaving him laying there, naked and
exposed.
He
curled up and said, “Hey what about me?”
I
looked over my shoulder and blew him a kiss as I ran to the bathroom for a
morning shower.
After
a long, hot shower, I pranced into his bedroom and rummaged through my suitcase
to find the perfect outfit for the day.
He said we would be traveling to a few different places and meeting a
few of his friends for wine tasting.
So
I picked out one of my favorite long sleeve, deep V neck blouses, a pair of
skinny jeans what were frayed at the bottom, and a cute pair of wedges. I also grabbed a flowing, capped shaw it case
it got cooler in the evening.
Little
did I know, it was going to get very hot that night.
We
arrived at our first tasting venue in the early afternoon and Nick introduced
me to two of his friends, Kipp and Hannah.
Kipp was your stereo typical, tall, dark, and handsome and Hannah was a
petite blonde with big boobs and curves in all the right places. They were such a warm and welcoming couple
and Hannah gave me a big hug to welcome me to the group.
Throughout
the day, as couples often do, the men huddled together and chatted about guy’s stuff and the ladies did the same. Hannah proceeded to tell me that they had
been married for 8 years and it was both their second marriages. She told me that she went to a swinger’s club
years ago as part of a bachelorette party and met Kipp there. She introduced me to a few of her
girlfriend’s at the second tasting venue and they all welcomed me with open
arms.
Hannah
continued to tell me that they had a nice home just down the street from Nick’s place and she and Kipp would love for us to join them
later that night for a night cap at their place.
Nick
and I enthusiastically agreed. Little
did I know, I was the night cap that they’d all
be enjoying.
Later
that evening, after a light dinner, we all hopped in an Uber and headed to Kipp
and Hannah’s place. It was equally as beautiful as Nick’s place
and in the same golf course community.
After
having another glass of wine, which I didn’t
need, I was already quite tipsy, Kipp suggested that Hannah show me her “to die
for” closet.
It
was huge! She had racks and racks of
shoes, in every color and style. The
mirrors and lighting was just superb and every woman’s dream.
Hannah
then opened another closet that revealed her lingerie collection. She had just as much lingerie as she did
shoes. I was so envious. She picked out a black lace babydoll and held
it up against me.
“Perfect!” She
said.
“Try it on!” She said
next.
“OMG really, here, I can’t.”
I replied.
“Oh yes, please. The
boys will love it!”
“The boy’s will love it?”
I thought.
“Here I’ll wear this one.”
Pointing to a dark red teddy which was just as luxurious.
Without
hesitation, Hannah stripped her clothes off and stood in front of me bare ass
naked. He had the most perfect tits and
shaved camel toe pussy that I wish I had.
She grabbed the skimpy red teddy off the padded velvet hanger and
stepped into it, pulling it up over her perfect tits and onto her shoulders. She looked so gorgeous.
I
just stood there in awe. She handed me
the tight lace babydoll and said, “Here
put this on, you’ll look so sexy in it.”
So
I unbuckled my wedges and stepped out of them, wrestled my skinny jeans off,
and removed my blouse. I was a bit shy
and hesitated to take my bra off, due to me only having a small natural A
cup. She quickly stepped behind me and
unhooked my bra and pulled it from me.
As I stood there wearing only my black gaff panty, she softly slid her
hand over my left nipple and smiled at me.
“You have such beautiful breasts hun,” she whispered.
“OMG, they’re so small compared to yours,” I replied.
“Oh hunny, yours are natural and so beautiful. Now here put this on, the guys are waiting
for us.” She demanded in a sexy voice.
“The guys are waiting for us?” I asked in an unsure tone.
“Yes, hun, they’re waiting for us in the Red Room,” she
replied.
“The Red Room? What’s
that?” I asked.
“Just come with me hun, you’ll see.” She said as she grabbed my hand to lead me
down the hallway and to the back of their house.
As
we entered the room in our lingerie, both Nick and Kipp were standing in a room
that was decorated in mostly red decor and lit with soft red lighting. I quickly looked around and couldn’t believe what I was seeing. The entire room was equipped with sex toys,
flogs, hand cuffs, ropes, chains, and many other sexual contraptions that were
sure to make even the strongest sexual creatures submit to their captor.
Both
men smiled at me and Nick reached out his hand to me.
“Babe, you look so sexy in your lingerie,” Nick whispered to me.
He
wrapped his arms around me and kissed me so passionately. I was so short without my wedges on and I
looked up at him and kissed him back. I
was so lost in the moment, that I didn’t even
realize that Kipp and taken Hannah over to a padded bench and bent her over
it. Tightly securing her wrists and
ankles with padded cuffs, fully exposing her freshly shaved pussy.
“OMG, are the guys going to fuck her like that?” I wondered.
Next,
Kipp walked over and offered his hand to me.
Nick
said, “Go with him hun, it’s ok.”
I
reached out and accepted Kipp’s hand and he led
me to another sexual padded bench. The
bench was about 2 feet wide and 5 feet long, with an additional bar mounted
across the top of the bench.
“What was he going to do with me?” I wondered.
He
told me to lay on my back and I did as ordered.
After laying on my back he grabbed both of my handed and handcuffed them
to the bar above my head.
I
was so nervous.
Then
he grabbed another pair of padded handcuffs and cuffed both of my ankles above
my head and secured them to the same bar.
I was completely cuffed and restrained to the sexual bench and
vulnerable to anyone’s desires.
Kipp
then grabbed a blindfold and slid it around my head and over my eyes. My senses were so heightened and I could feel
every sensation tingling in my body. I
could hear both of the guys unzipping their pants and removing their
clothes. The anticipation of what was to
come, was sending me over the top.
As
I lay there with both my hands and feet restrained above my head and my trans
pussy fully exposed, I could feel someone step in front of me. I heard him unsnap the cap from the bottle of
lube and then felt the cool sensation of him properly lubing up my hole.
Slowly,
what felt like one finger, was inserted into me and pulled back out. I gasped in the pleasure of the unknown. Again, but now it felt like two fingers,
inserted inside of me.
I
was in such anticipation, wondering if it was Kipp or Nick standing in front of
me.
Then
with a gentle push, my unidentified owner thrust into me, and we both moaned in
pleasure. He pushed in so deep that I
could feel him in my stomach. He slowly
pulled out and thrust in again.
Continuing to pound the end of my submissive hole, I was completely at
his mercy and taking everything that was given to me. I could feel him lean forward and grab hold
of the horizontal bar that my hands and feet were cuffed to. Enabling him to control me more and thrust
harder.
With
each thrust into me, the very distinctive sound of his balls slapping against
my ass echoed throughout the room. But I
could still hear Hannah receiving the same pleasure. With each powerful injection of cock into her
freshly shaved pussy, the bench she was submissively strapped too, would slide further
and further across the floor.
At
one point, both of our captors were pounding in unison as if their sexual
performance was planned for the evening.
After
both of us ladies getting a good fucking for about 20 minutes, they
stopped. No one said a word. They just stopped.
“What was going on?”
I wondered. “Were they done? Did he cum?”
Then
I heard them switching. The other
unknown donor had replaced the first captor and with no warning or words,
forcefully penetrated me.
I
screamed in pleasure! “Oh fuck, you’re so hard!” I gasped
out.
By
the sounds of Hannah’s pleasurable moans, she had received
her new donor too. Neither of them took
a break, they both continued delivering their powerful, ass slapping, thrusts
into us and controlling our worlds.
Just
as an extreme sensation of lust and pre-orgasm shook my body, I heard Hannah
scream out, “Oh damn, I’m going to cum!” Her anonymous thruster gave her a few last
pumps and she exploded right there while being filled with his thick
shaft.
My
anonymous thruster didn’t stop. He just kept pounding and pounding. At that point, they did to me, something that
I have never experienced.
While
my donor was continuing to dominate me, Hannah’s
captor removed her from the bench and led her to my sexual contraption. With her hands still restrained behind her
back, he grabbed her long blonde her and forced her head down to my trans
shaft. As she was bent over my stomach
and now, deep throating my trans shaft, both of our cock holsters were being
used to service our male captors. As my
male captor continued to thrust into me, I could feel him getting harder and
harder. I knew he was getting ready to
blow his load deep inside me.
“Oh fuck, I’m going to cum!”
He moaned.
And
at that moment, his entire load being held captive inside his balls, unleashed
inside me with such force, I could not hold back any longer and I also erupted
out of my trans member and straight down Hannah’s
throat. My sperm donor collapsed on top
of me just as Hannah’s donor exploded into her tight and freshly shaved
pussy.
I
could feel the unmistakable feeling of his deposit oozing out of my gaping hole
and down my ass crack. I was stretched
open for so long by two huge cocks, my trans fuck hole no longer had any
elasticity to it and was gaping wide open.
Before
collapsing from complete exhaustion, the last thing I heard was an all too
familiar sound.
The
sound of Hannah swallowing my trans load of cum.
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