Date: Fri, 21 Jan 2022 16:46:04 -0800
From: Tiffany Cox <tiffanytvslut@gmail.com>
Subject: My First True Love

My First True Love

To give you all a bit of history about myself, I am an early 40's part time
CD who has been spending every single moment of my free time since my late
20's as my feminine alter-ego Tiffany. I would spend at least one weekend,
sometimes two or three weekends, per month living en femme and enjoying
everything single woman could enjoy. I had a number of regular sexual
partners and also loved to continue to expand my social network.

Now to refresh, I am a full figured gurl who stands 5'10" and weigh about
235 pounds. I have a fair complexion (highlighted by some sexy thong tan
lines on my ample bottom and my budding B-cup breasts) and keep my body
hair free from the neck down, save a cute little patch above my 5"
clitty. I wear a lightly curled long brunette wig that falls well past my
shoulders. I have a pair of piercings in each ear and a bellybutton ring.

One Fall weekend I had set a date with a new man I'd met online and I was
super excited to finally meet him in person. Alexander was the name he gave
me and he was soooo handsome. He was tall, 6'2" and well built with a very
muscular body. He had stunning eyes and a disarming smile. We had been
conversing online for quite sometime and had exchanged pictures and had
even had a couple cam sessions. I generally don't like to cam with guys but
there was something about him that made me want to bend to his will.

Alexander was quite the gentleman and was very complimentary in every one
of our conversations and exchanges. He really loved to see me get off when
we would interact and kept telling me how much he wanted to see me take his
thick black cock in my tight sissy pussy. After a couple months of
misaligned schedules we settled on a Saturday afternoon in a local hotel. I
agreed to get the room and let him know when I would be ready for him. I
couldn't wait to add another notch to my headboard ... haha.

Saturday arrived and I got an early check-in so we could enjoy the entire
afternoon in each others arms, making each other feel as amazing. I got
there, immediately jumped in the shower and cleaned up, shaved and douched
to make sure I was as clean as could be. I got out and toweled off and
started in on my makeup. I did my eyes in a sultry look and added a bright
red lipstick to finish off the look. I put on my cute wig and added a
diamond stud and a large silver hoop to each ear as well as a black choker,
tennis bracelet and a couple rings to round out my jewelry.

I slipped on a black waist cincher, black stockings and a black thong
before hooking my black bra and adjusting the shoulder straps. I then
stepped into a cute black velour micro mini skirt that barely covered my
thicc ass and finished my ensemble with a floral black blouse that was
low-cut and gave him a great view of my cute little cleavage. I slipped on
my over the knee black suede boots and adjusted everything. I was ready.

I texted Alexander to come to my room and sat back with a glass of
champagne to try to clam my nerves. Even after a couple hundred encounters
I still get the butterflies in my stomach when I'm meeting someone new.

Within 20 minutes I heard the knock on my door and got up to let me new
beau in. I unlatched the lock and pulled the door inward and just stood
there with my hands on my hips, hoping he would like what he saw. Alexander
smiled and asked if he could come in. I waved him in and planted a big kiss
on his lips as he leaned in to hug me. We exchanged hellos and compliments
on each other's looks but it didn't take a minute for us to be in each
others arms on the couch kissing and snuggling.

I just felt right with him, right from the get go. I don't know what it was
but there was a connection I hadn't felt before. I just wanted to be with
him no matter what. I'd always felt like I couldn't transition because I
was older and had an established career and friends. Alexander had me
questioning this stance from the first time I felt his hands on my body.

I couldn't help myself, I dug my hand into his pants and fished out his
huge cock. It wasn't overly long but it was easily as thicker than a can of
Red Bull. I massaged it with my hand as I sucked on his tongue. He was
squeezing my tits and rubbing my nipples as a moaned out my pleasure. I
felt his dick grow as I stroked it and I couldn't wait any longer. I
lowered my head into his lap and kissed the giant mushroom head while I
cupped his balls. He leaned back on the couch and spread his legs even
further to let me slide into position.

I dropped to my knees in front of him and continued to work his cock with
my hand as I dipped under and took each of his balls into my mouth and
massaged them with my tongue. After giving them some loving attention I
moved back up to his rock hard spear. I am a very good deep throat artist
with a ton of experience but I couldn't get his massive tool past the back
of my mouth. I felt disappointed but worked his big head with my mouth
while I slid my hand up and down his shaft. Alexander sighed deeply and let
me know he was enjoying the blowjob. He told me it was his turn to make me
feel good.

He pulled me up off his mammoth dong and motioned for me to move to the
bed. He had me kneel and pushed me forward to I was in doggy style. He
pulled down my panties and began to rub my tight little flower with his
fingers. Then he began to lick around my sissy twat before plunging his
tongue as far as it would go. I let out a gasp and began to urge him on as
he ate my pussy with a passion I'd never felt before. He reached between my
legs and started to rub my soft gurl cock and it felt amazing. I was
moaning out how great his ministrations felt as he continued his oral
assault on my hole.

Alexander pulled away and stood behind me. He brought his huge cock up to
my pussy and began to rub it all over my opening. I looked back at him and
asked him if he brought the condoms like he said. He said he didn't have
time to grab them. I only had regular Trojans, no way that was going to fit
his giant cock. I had to have him so I asked him to please make sure he
didn't cum inside me. He lubed up his cock and began to push himself into
me. I tried to relax myself but it really hurt when he began to push
anything beyond his head into me. I've had a lot of different cocks inside
of me before, some were longer but none were thicker than his monster. I
readjusted a few times but we couldn't seem to get him any deeper than an
inch or two. He was getting frustrated and so was I.

I turned around and started sucking his cock again. Alexander said it felt
good but he also said he couldn't nut from just oral sex. He asked if we
could try again saying, "I wanna get some more of that pussy."

I laid on my back and lifted my legs up onto his shoulders as he placed his
cockhead at the opening of my boi cunt. He rubbed it around and then began
to push his way into me. He smiled as he stared into my eyes as he inched
his way in, I gritted my teeth and tried to smile back as I felt him invade
my cunt deeper and deeper. It hurt soooo bad but I was determined to make
this my man feel good.

Alexander leaned down and kissed me but he could tell I was in pain. He
eased back out of me and asked if I was ok. I told him it hurt but I wanted
to please him. He told me he couldn't do anything that he knew I wasn't
enjoying. He was so sweet. I told him I would give him head all night if I
had to but I didn't think I could take him in my pussy anymore. He smiled
and said that it was ok.

I settled back into giving him as good a blowjob as I could and worked his
cock for close to an hour. He wasn't lying, he couldn't get off from just
head. He told me to lean back and to please myself and he would masturbate
himself. I laid back on the bed and began to rub my little cock as I
watched him stroke his cock. It didn't take five minutes and I could tell
he was ready to cum. I scooted over and rest my head under his dick in
anticipation of my reward. Rope after rope of hot jizz exploded out onto my
face and into my mouth as he jerked his twitching cock just inches from my
nose.

I kept rubbing my cock and when he erupted it sent me over the edge. I
began to shudder as my climax racked my body and I squirted out my gurl
juice all over my tummy. As my breathing subsided I grabbed his dick and
put it back in my mouth and sucked out every last drop of his nut.
Alexander thanked me as I popped his cock out of my mouth.

We began to snuggle again, with him making sure I didn't get our cum on him
... lol. We talked and laughed for a while before he got up to use the
restroom. He asked if he could take a shower and I said, "sure." I got up
and washed his hardened cum off my face and mine off my stomach. I laid
back on the bed and waited for him to come out of the shower.

He came out of the bathroom after drying off and stood there naked. I could
see his muscled frame and it was a sight to see. I must have been leering
at him because he laughed and asked me if I liked what I saw. I said, "you
are just so hot baby and you have a great cock. It looks amazing hanging
down between your legs."

He said it was a shame I couldn't take the whole thing.

I was crushed.

I told him I was sorry and he said not to be, it wasn't the first time a
gurl couldn't handle his girth.

I told him I would do everything I could to make sure I could handle him
the next time we got together. He chuckled and said, "we'll see."

It was like a challenge.

Alexander said he had to go and gave me the sweetest kiss before heading
out.

When I got back home the first thing I did was head to my favorite online
toy shop to find a fat dildo to train my pussy with.

We continued to chat via text but with my work schedule and his things just
didn't line up for us to get back together. We were both disappointed but
our relationship still seemed to be growing as we explored so many
different topics in our lengthy conversations. We also continued to cam
when we could. As we got closer he opened up to me and told me his real
name was Kai and that he wanted me to know that he was in love with me and
that he had to see me again soon.

I felt so happy and told him I loved him too. I thanked him for trusting me
and told him I would love to see him again. We settled on a weekend later
that month and began to plan our lover's rendezvous.

I continued by "training" every night. I kept assuring him I would be able
to handle him this time and he kept teasing me about not being able to take
his entirety. I was determined to show him how much I loved him.

As our date approached I decided to go all out. I headed to my favorite
online shopping spots and purchased some new outfits, lingerie as well as
some extras I didn't usually deal with. I got some very long burgundy nails
and extra long fake eye lashes. I also ordered a large butt plug to help
keep me ready for my man.

I was giddy the entire week leading up to our date. I kept sending sexy
texts and promising to be able to take him for as long as as hard as he
wanted to fuck me. He would send back cute texts but he kept questioning if
I could live up to my word.

Then Kai sent a very sensual text, telling me everything he wanted to do to
me. It was very explicit and had me extremely turned on. It ended with him
saying he wanted to share his love with me in the most intimate way and
that he really wanted to finish by cumming deep inside of me.

OMG!!!

I had only had a couple of guys cum inside me before and they were only
with one guy who I was with monogamously for over a year and another guy
who I lost my virginity to. But I was intrigued. I really was falling for
this guy, I was head over heels for him and wanted to please him so badly.

I asked him about getting tested and he said he would. I told him if he had
a clean test I would love to share the most intimate experience two lovers
can have with him.

Saturday morning arrived and I headed over to the hotel to get ready.  Kai
said he would be available at 4pm. I got to the room at 11am and checked
in. I decided to work my dildo to make sure I was opened up. I knew I would
have to do it periodically throughout the day before Kai showed up. He was
massive and I didn't want a repeat of our first encounter. I laid on the
bed, facedown, and opened my legs. I reached behind me and lubed up my
sissy pussy. I grabbed the big dildo and began to work it into me. I felt
the head pass by my outer ring and I left it there for a moment before
pushing it further in. It was about 9 inches long and I eventually had the
entire length inside me before I took a break.

I ran a bath and filled it with my favorite bubble bath. I sank into the
steaming hot water and relaxed for about an hour. I had to refill the tub
with more hot water on a couple of occasions but by the time I was done I
was ready to get ready for my man. I moved over to the shower and made sure
I was smooth all over and then toweled myself off.

I moved to the vanity and sat down to get ready. First I painted my
toenails a pretty burgundy to match the long fake nails I would attach
next. I always love doing the fake nails but they are such a pain I save
them for special occasions. Side note, they make me feel so gurly,
especially when I have to text on my phone, they make it so difficult but
worth it lol.

After getting my nails on I moved to my makeup. I did my best to create a
sexy look. I put on my foundation and blended it perfectly. I added a
little blush to highlight my cheekbones and then set to work on my eyes. I
added the liner, thick with small little cat eye extensions at the
corners. I used the shadow to make my eyes look dramatic. Big fake lashes
were next and then a ton of mascara. Deep red lipstick highlighted my
pouting lips, I looked sexy.

I then put on my wig, combed out and then put it up in two pigtails. Put on
my jewelry, a cute silver necklace with a "T" pendant for Tiffany, a number
of bangle bracelets and some massive hoop earrings. I had also gotten a new
bellybutton ring for this occasion. It was a Queen of Spades pendant that
dangled down off the piercing. I hoped Kai would like it.

Next I decided to dispose with an outfit, I would just wear my lingerie. I
pulled up my white waist cincher and then I rolled on some sexy white
fishnet stockings and attached them to the garters on the cincher. I tucked
my tiny little clitty into a sexy white cotton thong and then added a cute
white babydoll nighty. I slipped into my white platform heels and decided I
was ready for my man. I looked like I could be a bride on her wedding
night.

I was sooooo excited to see my man.

It was only 3pm, I had some time to kill before Kai would be there so I
decided to play with my dildo some more. This time I placed the dildo on
the coffee table and sank my pussy down on it. I slowly worked my way all
the way to the base. I grinded on it for a bit and then began to work my
ass up and down it's entire length. I could feel my orgasm approaching so I
backed off and slowed my pace. I lifted myself all the way to the top, with
just the head staying inside me, then slammed back down on it a couple
times before deciding it was time to clean up and make sure I was ready
when Kai got there.

I headed to the bathroom and douched my pussy. I applied more lube and put
my panties back on. I grabbed a glass of wine and sipped it on the couch as
I waited for my man. At 4pm sharp I heard the knock on the door and rushed
over to let him in. Normally I wait a minute or so, not to seem so anxious
but I didn't care, I wanted my lover.

I threw the door open and posed for him, I didn't care if anyone saw me. My
neighbors would be hearing my screams of pleasure soon enough, I didn't
care if they knew my man was there to fuck me. Kai wasn't so sure that was
a good idea. There were a lot of people milling around and he scampered
into the room, closing the door behind him.

He said, "You must be happy to see me baby."

"I have been going crazy with desire since we set the date luv!"

I lept into his arms and wrapped my arms around his neck and pulled him to
me. Our lips met and I swooned. He kissed me hard and passionately, my
knees buckled. Kai held me up and moved his lips to my neck. Kai picked me
up and carried me to the bed where he laid me down on my back. He kneeled
down on the ground and pulled my panties off. He lifted my legs and spread
my cheeks and began to rub his fingers over my rosebud. Then he pulled my
legs back down and grabbed my limp clit between his fingers, stroking it
lightly.

Kai then surprised me by engulfing my still-soft cock in his mouth as he
fingered by cunt. I was in shock, this was totally unexpected. I writhed on
the bed in ecstasy as he continued to finger bang me while sucking on my
hardening gurl cock. I began to moan loudly, screaming out my love for this
man who was making me feel so good. I told him I needed him inside me right
now. Kai stood up and turned me over. He pushed his cockhead against my
sissy twat and began to ease it in. There was some resistance at first and
he questioned whether I would be able to accommodate him again. I asked him
to use some more lube and he obliged. His now glistening cock once again
began to slide its way into my love canal. Kai was gentle but firm as he
inched forward until he was all the way in, balls deep. I had done it, just
like I promised.

Kai was such a good lover, he let me adjust as he caressed my back, butt
cheeks and upper thighs. He leaned forward and kissed my shoulders and neck
and when I turned my head to meet him, my lips as well. I told him I was
ready for him to make love to me and he postured up and began to ease out a
bit, only an inch or two before pushing all the way back in. I gasped but
reassured him that I was ready for this. He began to make longer strokes
and soon I was pushing back into him as hard as we could go. It felt
amazing as I adjusted to his thickness.

Kai was an amazing lover and he made sure to tell me how much he loved me
as he piston'd his rod in and out of me. He ran his hands up and down my
sides, cupped my little titties and pinched my nipples. This was the best
sex of my life! I truly was in love with this man.

I told him I wanted to see his face as he made love to me so he pulled out
and let me roll over to my back. He pushed my thighs up and lined up his
dick with my sloppy pussy. He slid right in all the way, filling me to the
hilt. I pulled him down by the neck and kissed him wantonly. I moaned out
my love for him and told him I needed his cum deep inside me. He kissed me
back and told me he couldn't wait to fill me but he was going to get me off
first. I told him how much I loved him and he told me he loved me too.

His dick felt so good stretching me more than I'd ever been stretched
before. The weight of him on top of me made me feel so gurly and feminine.
He moved in for another kiss and then sucked on both of my nipples ... I
was getting close. Kai pulled me to the end of the bed and stood up on the
ground. He used this increased leverage to really start to pound away at my
pussy. I could feel my orgasm welling up as he stroked my clit in rhythm
with his fucking. I tried to lift up to meet his thrusts but could barely
muster any movement as his cock impaled me.

The waves of pleasure rushed thru my body as I squirted out my orgasm, Kai
telling me how good my spasming cunt felt as it clenched around his big
dick. I screamed out my love for him as I covered my tummy and tits with a
massive explosion of cum. Kai continued to pump his swollen member in and
out of me as I came down from my climactic high.

He pulled out and ordered me back to my knees. As I sat up he kissed me
deeply and told me how much he wanted to plant his seed inside my sissy
womb. I told him I was ready for him and looked forward to sharing that
close experience with him, consummating our love. He grabbed my hips as I
got to my knees and pulled me to the end of the end of the bed and slammed
his fat dick all the way back in me. I felt him begin to pull me by my hips
and I knew what he wanted. I began to rock back and forth, sliding his
cock's full length in and out, my ass taking it to the root and then back
to just the head over and over. I reached under and caressed his low
hanging balls with my long nails as I rocked my hips back and forward over
and over.

I could tell Kai was getting close when he pushed me down and held my waist
as he power fucked my pussy. He began to growl a bit as his pace quickened
even more, telling me I was his gurl and that my pussy belonged to him and
that he was going to nut deep inside it to mark it. I felt him freeze as he
began to empty his balls into me, moaning out as he ejaculated in my worn
out pussy. I lifted my ass up and back into him to try to milk every drop
of his seed into my body.

He collapsed on my back, pinning me to the bed. I felt his fast, heavy
breathing and knew he had given me everything he had. We laid there like
that, with him still inside me, for what seemed like and hour. He stroked
my shoulders and head while I squeezed my ass every now and then to tease
him a bit. He kissed my neck and told me he loved me and I told him I loved
him too. Neither one of us wanted to move but he finally slipped out of me
and headed to the bathroom to urinate.

I felt empty but completely satisfied. When Kai came back to bed I snuggled
up next to him, laying my head on his chest. He ran his fingers across my
face and told me how happy I had made him. I cocked my head, looking
directly in his eyes, and told him I was the happiest gurl in the world
right now. He smiled and kissed my forehead and rubbed my shoulder. I
looked back down and saw his cock stirring.

I told him I could tell he was pleased by the way his cock was coming back
to life already. I slid down towards his groin and took his half-erect
penis in my palm. I brought it to my lips and began to suck the
head. Within a minute it was at attention once again. I continued to suck
the head while I tickled his balls. I felt Kai's hand push down on the back
of my head and knew he wanted me to take as much of him as I could. I took
as much of him as I could and ended up gagging a bit.

Kai guided my head up and down for a bit before asking if I was ready to
take him again. I told him I thought so and he asked me to get on top of
him. As I slid up I felt his first nut start to drain out of me and boy was
it big. I saw a big puddle on the sheets and laughed as I pointed it out to
Kai. He said don't worry baby, I'm going to fill you up again. I straddled
him and slid his cock back into me with zero resistance.

My man lets out a massive sign as I began to rock my hips and grind on his
fat cock. He grabbed my hips and began to guide me up and down, forward and
back, using me to jack his cock with my tight sissy cunt. It felt amazing
to know I could please this man I had fallen for. I leaned forward and
kissed him deeply, our tongues entwined, as he continued to direct my
motion with his strong hands.

He drew away from our lip-lock and moved his attention down to my rock hard
nipples, taking each into his mouth, between his teeth, before flicking
them with his tongue. This drew moans from me as he took my breath away
with his suckling as he kept up his assault on my now gaping fuck hole. I
was in ecstasy.

Kai looked up into my eyes and told me he loved me and he wanted me to be
his gurl. I just melted and the tears began to stream down my face. I
stopped working my ass and just froze there atop my love. He asked what was
wrong and I told him nothing was wrong, that I was just so happy to hear
him say that and I was just processing all the crazy thoughts that were
running thru my mind.

I knew I really liked him and we had been saying we loved each other for
weeks but this experience cemented everything I was already scared to admit
to myself. I had never really fallen in love and I wasn't really sure until
that moment. But now, completely assured that this was the guy, I was
overwhelmed with emotion between us and between the struggle I'd been
fighting for years ... was I really a woman?

This was a turning point, I knew from this point forward I wanted to live
my life, every waking moment, as Tiffany. And I wanted to spend my life
with Kai! As you can imagine this is a lot to process, especially when you
are impaled on a giant cock, looking into your love's eyes as he expresses
his love and desire to you.

As these thoughts coursed thru my mind I felt Kai reach up and gently brush
my tears away as he told me, "It's okay baby gurl, I know you feel the
same. I'll always be here with a shoulder for you to cry on, to share the
ups and downs with, to make you feel like the sexiest gurl in the world!"

My heart was so full and I couldn't help but dip down to kiss this awesome
man and tell him he was the love of my life. That I would be his best
friend, loyal supporter and lover for as long as he would have me.

He slowly started to move his hips as he began to thrust in and out of
me. I just sat there and stared into his big brown eyes as he made love to
me. My tears had subsided but I was still a ball of emotion as I felt
feelings I'd never even imagined before.

Kai pulled me in for another kiss and, without pulling himself from me,
rolled me onto my back. I wrapped my legs around his waist and my arms
around his neck as he kissed me deeply on the lips before moving down to my
neck. It felt wonderful, the most sensual feelings of my life.

He told me he was getting close and I told him "Don't wait for me baby."

Within a minute I could tell he was about to burst, his breathing became
heavy, his face strained, as he picked up the pace of his downward thrusts
into my stretched out pussy.  I told him to, "Give it to me my love, I want
your seed inside me baby! Make me your gurl forever Kai!"

With one final penetrating thrust I felt my lover push his massive cock as
far as it would go before he froze, then his body shook and he grunted
loudly as he flooded my bowels with his man sap. One, two, three violent
shudders signaled each shot of his ejaculation deep within my sissy
garden. He began to slide in and out a bit again as he extracted every
possible drop his balls had to offer and implanted it into me before
collapsing on my chest, his head resting on my shoulder as he panted,
trying to catch his breath.

I stroked his face and head and told him how much I loved him and how much
I appreciated him and how he had made love to me. We lay there like that
for at least 10 minutes, his cock still inside me, as we kissed and
snuggled. He finally plopped out of me when Kai rolled a bit to the side
and a torrent of his semen rushed out of me. I could feel it run down the
crack of my ass and hit the sheets, puddling against my cheeks. We both
laughed, acknowledging the fact that our lovemaking had manifested itself
in one of the biggest loads we'd ever seen.

"Holy moly!," I exclaimed.

"That's just what you do to me Miss Tiff!," he retorted.

We both laughed.

I jumped up and told him I needed to shower after he had defiled me. I
winked at him, gave him a peck on the cheek and hopped up and headed to the
shower. The scalding hot water felt good as it fell over my tired body. I
soaped up all over and then grabbed my douche bottle and filled it up. I
bent over and cleaned my now tender sissy pussy. I washed my face and then
just stood there in the steamy shower as the water continued to cascade
down upon me.

I was lost in a daydream of love and lust, running back the days escapades
in my mind and I couldn't help keep thinking the same thought ... I wanted
to be this man's woman and I didn't care who else knew about it. Not my
family, not my coworkers and certainly not any strangers on the street. As
long as my man was happy with me I would proudly be my feminine self for
the rest of my life.

KNOCK KNOCK KNOCK

Kai banged on the door and asked if I was going to save any hot water for
him. I giggled and said, "Just a minute sweetie!"

I rinsed off one final time and shut the shower off, grabbed a towel and
wrapped it around my body. I slipped my wig back on and made sure it looked
cute before dipping back into the room.

"The bathroom is all yours my love," I told him.

He thanked me and gave me a sweet kiss before heading in.

I sat back down at the vanity and proceeded to redo my makeup. I had most
of it done by the time Kai was done showering. I finished up my eyes and
began to apply some blush before pulling out my lipstick.

"I think you left the last coat on my dick baby," Kai said with a chuckle.

I just rolled my eyes as I added a think coat of deep red to my pouty lips
before pursing them in his direction. He snuck a quick kiss on my cheek so
as not to mess up my newly painted lips.

"So what do you want to do sweetheart?"

"I don't know, I'm kinda hungry," I replied.

"Cool, let's go get something to eat," said Kai

He said it so nonchalantly it made me so happy. He didn't mind taking me
out in public and that is such a beautiful thing for a gurl like me. Lots
of guys, and I mean lots, had wanted to have sex with me and hang out in
private or at T-themed events but to want to take me, a pretty passable yet
not 100% gurl, out in public was so reassuring.

"Where do you want to go honey?" he asked.

"I don't know, you pick baby," I told him.

He told me about this cool gastro pub not too far away where we could get
some good drinks and food. I told him that worked for me.

I started to get dressed and thru on a clean white cotton thong and pulled
up the waist cincher I had been wearing earlier. I grabbed my super tight
denim jeggings and pulled them up my legs and over my ass. I picked up the
bra that had been discarded earlier and put it back on and then added a
cute baby pink blouse and a black sweater to complete the look. I put on my
white converse low tops and grabbed my coat and was ready to go.

"You get ready pretty fast there gurlie," Kai commented as we headed for
the door.

It was blowing pretty good and the late fall Santa Ana winds were chilly so
I wrapped my scarf around my neck and put on a cute pink beanie to make
sure I stayed warm.

"Okay, you're just like every other girl I've dated, you get cold super
easy," he said laughingly.

"Whatever!!!" was all I could muster as I shrugged my shoulders.

He opened the passenger side door for me and soon we were off to the
restaurant. During the short ride we chatted about how awesome it was to be
with each other and how perfect we were together. The conversation
continued after we were seated and it flowed so easily. I was so
comfortable around him and enthralled in our conversation I was totally
oblivious to everyone around us.

I'd spent quite a bit of time in public as Tiffany and it wasn't something
I worried about but I was always cognizant of my surroundings, seeing if
anyone was clocking me or if there were any people around that might be
dangerous. With Kai I didn't even think to consider what was going on
around us. I was caught up in the conversation and my thoughts were
entirely about him and I and how perfect everything was.

I think the waitress could tell we were madly in love. She commented about
how I was glowing and how cute we were together. I made sure Kai left her a
good tip, she was so sweet.

When we finished up we went down to the beach and walked along the park
path behind the sand, periodically stopping to watch the waves crashing. It
was very windy and I was glad I had worn my heavy coat and had my scarf and
hat but my hands were freezing. I snuggled up to Kai and put them against
his skin on the small of his back as I hugged him. He said it might be time
to take me home and warm me back up. I sighed contentedly and agreed, I was
ready to head back to the room.

As we drove back to the hotel Kai told me how excited he was to start round
three. I chuckled and asked him if he could even handle another round. He
just looked down at his crotch and my eyes followed. He was already hard
and bulging. Well, he was ready but I was a little worried about how my
twice-ravaged sissy twat was going to handle a third battering. I told Kai
he may have to be extra gentle and he just smiled and told me not to worry,
he'd make sure he wouldn't hurt me.

I smiled at him and told him, "That's why I love you so much babe, you are
so sweet."

Then I leaned over and gave him a kiss on his cheek and ran my hand over
the bulge in his pants, feeling how hard and swollen it was. The little
tease had him raring to go as we pulled into the hotel parking lot. He
found a space near our room and hopped out. He made his way to my door
(what a gentleman) and opened it for me. As I slipped out of the seat and
to my feet I brushed the back of my hand across his tented pants and let
out a sarcastic, "Oops!"

"Damn woman, you are so mean," Kai said with a chuckle.

He grabbed my hand and walked me past the pool where there were a bunch of
people hanging out. I asked him if he thought the people were looking at
his giant bulge and he said, "Who cares."

Then he slipped his hand down to my thicc ass and gave it a squeeze. I was
surprised and jumped forward a bit only to have him follow up with a pretty
solid smack to my bottom. I turned around and kissed him madly as we
embraced right there, for everyone to see. If they didn't know the white
gurl was heading back to her room to get some more black dick before, they
knew now.

We barely got in the room and closed the door before we were pulling each
others clothes off. I lifted his shirt over his head and began to work on
his belt buckle. I had slipped my coat off and Kai pulled my sweater and
shirt right off as I undid his belt. I yanked his pants and boxers down and
quickly went to work on his big dick with my mouth.

I spit on it and worked the head with my lips and tongue as he slipped his
hand inside the cup of my bra and tweaked my right nipple. I moaned on his
cock and began to work more of the shaft into my mouth. I was in a rhythm,
bobbing up and down on my man's fat dick when he pulled me to my feet. He
guided me to the bed and had me lay down on my back. I unhooked my bra and
tossed it aside as I fell backwards on the bed.

Kai pulled off my shoes and then peeled my skintight jeggings down my
legs. I reached down and rubbed my long-nailed finger over the head of my
cock which was still encased in the white cotton thong. I wet spot was
forming as pre-cum leaked from my clitty. Kai grabbed me under my thighs
and pulled me to the end of the bed and pulled my panties down my legs and
off over my feet. He kissed me from my ankles to my knees to my inner
thighs.

It felt so good and I let him know. "Baby, I love you, you give me so much
pleasure Kai!"

He then pushed my legs up towards my chest and apart as he drove his tongue
into my swollen honeypot. It was a bit sore as he began to lick around my
fuck hole but that pain subsided as he continued to work with magical
tongue in and around it. He spit on it and rubbed it in with his fingers,
inserting one, then two as he began to gently stretch me back out. I
started to grind on his fingers and then he added a third. I squealed a bit
and he retracted it.

"No, please don't," I said, "it feels good lover."

He reinserted it and I continued to grind on his hand. Then I felt him
nuzzle up to my tiny scrotum with his mouth. He took the entirety of it
into his mouth and suckled on it while he ran his tongue all around it. It
felt amazing and I couldn't help but moan out. I reached down to stroke my
rock hard cock but he brushed my hand away. He released my balls from his
mouth and ran his tongue up the underside of my clit, from the base to the
head before he swallowed all five inches of it. He began to suck it up and
down as I continued to smash my pussy down on his three thick fingers,
loosening myself up for the cock slamming that was sure to come next. It
felt so great I knew I couldn't keep this up much longer, I was going to
cum.

And then it happened, I just stiffened up and screamed as I shot my gurlie
load straight into Kai's mouth. He kept fingering me and continued to suck
my cock as I clenched his head and tried to get him to stop. It tickled so
much but he wouldn't stop. I was screaming and giggling and tried to get
away but he just held me down and continued to milk every drop of my creamy
nectar from my softening cock. Finally, as the sensitivity subsided he let
my tiny limp clit fall from his mouth and he moved up to kiss me. I opened
my mouth and accepted his cum covered tongue into mine. He spit my sweet
cum into my mouth and we savored it together as we continued to kiss before
I swallowed it down.

Kai broke away from our loving kiss and lifted my legs back up. He pushed
them wide and grabbed the lube and rubbed it into my aching ass. He then
coated his big cock and began to rub it all over my opening. He gently
eased it in, inch by inch, until his full length was firmly seated in my
sissy pussy. He told me how good it felt as my cunny gripped his huge pole,
how soft and silky it was inside of me. I told him how great his cock felt
stretching me out and filling me.

We laid there, kissing and snuggling as he piston'd his cock in and out of
me for what seemed like an eternity. I just kept encouraging him as he
adjusted his stroke from slow deep thrusts to shallow quick ones and
everywhere in between. I could feel his heavy balls slapping against my ass
when he picked up the pace and began to really pound away. I was so turned
on I began to get hard again.

My little cock was trapped between our bodies and the friction was building
me up for another orgasm. I locked lips with Kai and moaned as I sucked on
his tongue. I think it turned him on because he really started to bang away
even harder with his cock slamming balls deep into me after each withdrawal
to just the head remaining inside of me. I was getting so close!

I let go of his tongue and moved my mouth to his ear. I whispered, "Baby I
love you so much, I never want you to stop fucking me daddy! Ima be your
bitch forever lover!"

This sent him over the edge.

Kai reared up and hammered his big fat cock into me over and over until he
roared out and came deep inside me. He arched his back and thrust all the
way into me and held himself there as he emptied his heavy balls. I gripped
his cock as tightly as I could with my sphincter and tried to milk every
drop he had into my body. As he gently started to move in and out again I
reached down and began to stroke my pulsing cock. It might have taken ten
strokes before I was squirting all over my tits and face. It was a huge
orgasm that swept over me and Kai lovingly rubbed my thighs and sides as I
lay there convulsing as wave after wave of climactic pleasure ran thru my
body.

My loving boyfriend then pulled his softening dick from me as he stood up
from the bed. I waved him over and told him he had earned a good cleaning.
I pulled his wet cock into my mouth and savored the taste of his cum and my
ass. I polished him up and left him limp and clean as he headed for the
bathroom.

"Oh my god baby," exclaimed Kai, "you are the best! No one has ever done
that for me before."

I just smiled and laid back in the bed and closed my eyes. I was the
happiest gurl in the world. I had a great guy who loved me and who I loved
back with all my heart. I knew we were perfect for each other.

The rest of the weekend was full of sex and conversation and more sex and
good food and more sex and snuggling. It was the beginning of what would be
a great relationship.

We are still together almost a year later and I have been living full time
as I continue to explore a full transition. Kai has been the most
supportive boyfriend and we have grown so close as we share our lives with
each other. I look forward to a lifetime of love with this wonderful man.