Date: Tue, 7 Nov 2023 09:50:53 -0800
From: Tiffany Cox <tiffanytvslut@gmail.com>
Subject: Tiffany on the Rebound pt.2

Tiffany On The Rebound
By Tiffany Cox (tiffanytvslut@gmail.com)

Part 2: Thursday

I woke up Thursday morning with plans to meet another old friend, really
more like a daddy to me. Richard is his name and he's such a great guy. He
has looked out for me for years and was always there for me when I needed
him. He's in his seventies but still in great shape and he's such a
gentleman. He loves to take me out to great restaurants and to the movies
and he loves to show me off whenever he can.

We've kept in touch the entire time I was in my relationship with Kai and
he was there for me to talk to as I worked through all the emotions I had
when we broke up. All that time he never pushed me to do anything I wasn't
comfortable with and was a total gentlemen, waiting for me to let him know
when I was ready.  I knew I'd see him as soon as I decided the time was
right and Thursday was going to be our night.

He had a big date planned, dinner at this cozy Italian place down by the
water and then a movie. We'd wrap up the evening at his place for some late
night fun. I had planned on spending the day lazily getting ready for our
date but I kept getting Kik messages from this guy who said he saw my
profile on the dating site I mentioned. He was relentless and eventually,
after trying to ignore him, got my attention.

His name was John and he was so obnoxious. His first pic was a cute face
pic but then he followed with a dick pic. He was MASSIVE! I tried to ignore
him but he kept after me saying how he like my pics and how cute I was and
how much he loved my big fat ass. Then he sent me a picture of him on his
Harley. I love men who ride motorcycles, I don't know why but I do.

I asked him if he would take me for a ride and he told me he would, and
that he'd take me for one on his motorcycle too. LOL, he got me to laugh. I
knew I'd be adding him to my date list this weekend, I just didn't realize
how quickly. He asked me when I could be ready and where he could pick me
up.

It was 11 a.m. and I wasn't meeting Richard until 7:30 p.m. If I got ready
quickly maybe I could spend a few hours with John before having to be back
by 5pm to get ready for my evening date. I told him where I was, he said he
could be there in 15 minutes. I told him I needed at least 90 minutes to
get ready so we planned on him being there at 12:30 p.m.

I jumped into action and got myself showered, shaved and dolled up over the
next 75 minutes or so. I picked out an outfit, tight jeans and a tight
white tank top with white cotton thong panties and no bra. I wore black
chunky heeled hiking boots and a black leather jacket. My hair was up in
two pony tails with cute pink and white bows and I wore some sexy giant
silver hoop earrings. As you can probably guess, I keep my nails long and
well manicured.

I was ready to go when he pulled into my hotel parking lot. I heard the
bike before I saw him and headed outside to meet him. He pulled right up to
me and told me to hop on. He handed me a helmet and helped me with the chin
strap. He ripped out of the parking lot and I was immediately on an
adrenaline rush.

He told me he knew a good ride that was not too far into the foothills
above the city. I told him I thought that would be fun and we headed north
out of town. I love the feeling of the bike vibrating beneath me and being
able to snuggle up behind my man. Riding is such a great thing to share
with someone.

As we made our way into the hills the traffic thinned out a lot and pretty
soon we were the only ones on the road. It was exhilarating taking the
tight turns and accelerating out of them. We were about an hour into our
ride when told John I would have to use the restroom soon. He was a
gentleman and stopped at the next rest area/picnic spot and I was able to
relieve myself. I reminded John, as I put my helmet back on and got back on
the bike, that we had to be home by 5 p.m. but I was all his until then. He
smiled and said why don't we go for a little hike here then. I dismounted
and said I thought that would be a great idea.

We meandered out the back of the rest area down a trail that led down to a
small canyon. As we walked we held hands and chatted. I mostly giggled
since I was so infatuated by him. As we got out of view of the deserted
rest area John slipped his hand out of mine and placed it on my right butt
cheek and gave it a squeeze. I cooed and asked him if he liked the feel of
it. He immediately pulled me close to him and began kissing my neck,
telling me he liked everything he could feel.

He slipped my jacket off and began to massage my perky little boobs before
grabbing by ass with both hands and pulling me in for a passionate kiss. I
sucked on his tongue as he probed my mouth with his, all the while groping
my butt cheeks and grinding his already hardening cock against me. I was
ready to pull that monster out and see what I was working with.

I dropped to my knees and began to work on his belt and then his jeans. It
isn't always easy with long fake nails but I eventually got them down
before pulling his underwear down and revealing his giant member. It had to
be eleven inches and while it wasn't the thickest cock I'd ever seen it was
definitely the longest. He just smiled as I looked up at him as if to say,
"I told you so."

I started tugging at it a bit as I admired the sheer size and heft of
it. His balls were very large and hung low, weighed down by a huge load of
cum I hypothesized. I took them in one hand and fondled them before taking
one into my mouth and gently sucking on it until I popped it out of my
mouth and moved onto the other one. John just laid back against a boulder
and told me how good my mouth felt. I moved my way up to his giant rock
hard cock and took the head into my mouth. I swirled my tongue around the
ridge of the head and flicked it at the sensitive underside. He put his
hand on the back of my head and gently guided it down the shaft of his rod.

I began to move up and down in a slow rhythm until I had about half of him
in my mouth. I could tell he wanted more as he kept up the pressure on my
head so I decided to try to take as much of him as I could. Now I have
deepthroated a lot of cocks in my time but never one this long. I was
determined to see what I could do but even I was surprised when my nose
nestled into his pubic hair. I had taken eleven inches down my throat, I
was so proud of myself. That pride was short-lived as I began to gasp for
air as he held my head down on his big dick. I struggled to pull up off his
dick but finally he relented and let me up.

He told me I was the first gurl to ever get it all down and he was hoping I
would be able to do it again. I told him, "Sure, but please don't hold me
there, I need to breathe too."

I went back to work and began to slide his dick all the way down my throat
and back out over and over. John was writhing in pleasure as I deepthroated
him. He told me he was going to cum if I kept that up and I told him that
was fine with me. He said he really wanted to make sure I got to enjoy
myself too. I told him I was and that it was fine if he wanted to cum in my
mouth or on my face. He said he had a better idea.

He pulled me to my feet and lifted me up on the boulder he was leaning
against. He unbuttoned my pants and pulled them and my panties around my
knees. He lifted my tank top over my head and tossed it to the ground
before he moved in closer to me. He kissed me and told me what a good
cocksucker I was. I thanked him and kissed him back sweetly. He then bent
down a bit and took my hard clit into his mouth and began to tenderly suck
on it. OMG, this felt amazing. He moved a finger to my honey pot and
started to open me up a bit. As he continued to suck he moved another
finger and then another into my hungry asspussy as I begged him to keep
going. John had me on the brink of orgasm when he pulled his head up off my
clitty and his fingers from my now-dripping sissy pussy. He told me it was
time for me to see if I could handle him. I told him I was ready and slid
down off the rock and bent over for him.

John entered me standing and took his time letting me get used to his
size. It didn't take long for me to be ready for his entire length. He
pulled my hips back into him and seated his cock inside me, balls deep. It
was an amazing feeling, he was touching spots no other man had touched
before. His thickness was good, not too wide but just right and he was
hitting me in all the right spots. He eased himself in and out at a nice
even pace and the constant pressure on on my P-spot had me leaking right
away.

He could tell from my moans that I was close and he leaned forward and
whispered in my ear to just let go. "C'mon baby, gimme that nut, I know
your close. Give it to me Tiffany, give it to me!!!"

I just melted and began to shoot. It was only my second ever hand's free
orgasm and let me tell you, it was amazing. John held me up when my legs
gave out. It was overwhelming, feeling his huge cock slide in and out as my
climax raged thru my body, I could barely see straight. Then he told me to
hang on, he was just about there too.

As I was coming back to my senses, I could hear him growling in my ear,
"Baby, where do you want me to cum?"

I told him, "Wherever you want baby!"

He said he wanted to cum inside. I said, "Yass daddy, please cum inside
me!"

He began pulling at my hips wildly and pounded away until going as deep as
he could and then unleashing a torrent of his babies deep in my sissy
womb. He panted and grunted for nearly a minute as he seeded me, coating my
insides with his manly spunk. I just stayed as still as possible and milked
his dong with my pussy.

He finally withdrew and it was like a flood ... lol.

Everything came out and drained down my right leg and onto the dirt. It was
a giant puddle and I cousin't stop staring at it. John told me that was
normal for him and that he could do the same thing again in 45 minutes. I
just winked at him and said I guess we'll have to see. He laughed as we got
ourselves back together and headed back to his bike.

Our ride continued on thru the beautiful scenery but we knew we had to
start heading back. I told him I'd love to give him a blowjob when we got
back to my place but we'd have to hurry. He rode like a madman to get back
in time and we arrived about 4:40pm. I invited him in and told him he
better not take forever. He laughed and said he was sure I would be able to
take care of him in 15-20 minutes.

I had him sit down on the couch and I crawled up between his legs. I
stroked his big dick up and down and spit on it to lubricate it a bit. I
nuzzled up to his balls and sucked on each of them before moving my head up
to the crown of his penis. I worked the shaft with my hands, rotating each
of them in a different direction, as I sucked on the head firmly. John
reached down with one hand and began to tweak my right nipple thru my tank
top. I moaned a bit as I continued to suck his cock. He suggested I go back
to taking him down my throat, he said that felt awesome earlier. I adjusted
my position to get in a better spot to take him all the way down my throat
again. As I eased him past my gag reflex and slowly got him deeper he began
to push me down again. I don't really mind but I was hoping he wouldn't
hold me there this time. Much to my surprise, I had barely gotten him all
the way down when he was pulling out of my mouth. I should have know what
was coming but was shocked when all of the sudden my face was splattered
with a giant fountain of cum.

I just started giggling as he unloaded what had to be ten thick ropes of
cum on my face. It was in my hair, my eyes, across my nose and both
cheeks. It was the biggest load I'd ever taken. Luckily I had some big fake
lashes and the left one was absolutely coated, I could not see out of that
eye.

"Sorry," was all John could get out as he chuckled at his handiwork.

I just laughed and told him it was ok.

I went to the bathroom to clean up and was shocked at just how much he had
cum. My face looked like I took ten loads and even my shirt was
drenched. My little tank top looked like I had been in a wet t-shirt
contest. I cleaned up as best I could and headed back out to say goodbye to
my new friend. He said thanks and asked me if I wanted him to send me the
video of the blowjob I had just given him.

I had no idea he was filming and generally don't let guys film my face when
we're having sex. I was a little shocked but was eager to see how things
unfolded. I told him I didn't appreciate him filming me without my consent
but that I did want to see it. He texted the video to me and we said our
goodbyes. I took a look at the video and laughed as I saw myself flinch
when his first stream of cum blasted my face. I think I sucked his dick for
less than 5 minutes before he came, I guess he enjoyed it lol.

I knew I had to get going if I was going to be ready for my date with
Richard. He always took me to nice places so I had a lot of primping to do
to make sure I passed and was looking as good as I could. I immediately
jumped in the shower and got the rest of the jizz off my face. I shaved my
legs again and made sure my bikini line was smooth and silky. Then I soaped
up my entire body and let the hot water run over me for at least ten
minutes before I got out and toweled off.

I always dress conservatively when I go out with Richard. He usually wears
nice slacks and a button down along with a coat. He likes me in longer
skirts and dresses, classical feminine fashion like you would have seen in
the 60's. Sometimes I like to wear something a little sexier for him to get
him going but never when we're out at a fine dining establishment where it
could draw attention to me.

Tonight I was wearing a long flowing blue maxi skirt and a cute floral
blouse with a light blue cardigan sweater. I had my shoulder length brown
hair curled but down and wore conservative silver jewelry including a
necklace with a "T" pendant for Tiffany that Richard had bought me and some
diamond stud earrings, also a gift from Richard.

I took over an hour on my makeup, I like to look as good as can be when I'm
out in a public place and want to make sure I pass. My look was subdued but
clean with only my eye makeup being a bit bold. Everything else was as much
of a natural look as I could manage. I packed up my clutch with cosmetics
and my phone and slipped on some cute white sandals before heading to the
door, my Uber was just pulling into the parking lot.

I jumped into the Mercedes, Richard always ordered me an Uber Black, he is
so generous, and made some small talk with the driver, a nice woman named
Manuela. She complimented me on my cute outfit and asked what my plans were
for the night. I told her, dinner and a movie and hopefully some fun after
with a giggle. She laughed and said she hoped I would get to make that a
reality. We chatted a bit throughout the ride and I thanked her and told
her I'd make sure my man tipped her well since she was so nice and a
pleasure to ride with. She said I better take care of him tonight with a
wink. I laughed and said goodbye as I closed the door and headed up
Richards driveway to his front door.

Before I could even knock, the door swung open and I was greeted by my
handsome Daddy. He saw on the Uber app I was arriving and was there waiting
for me, such a sweetheart. He invited me in and handed me a glass of
champagne, he knows it's my favorite and offered me a toke from his bong. I
declined the pot but was happy to sip on my drink. We kissed and chatted a
bit, he said we had a few minutes before we had to leave and asked if I'd
like to give him a little preview of what he would be seeing later that
night.

He pulled his zipper down and fished out his half-erect cock and asked me
if I wanted to suck it. I told him I did and kneeled down before him,
gently kissing the head of his cock before running my tongue up and down
the underside of his shaft. I held out my tongue and peered into his eyes,
he always loved slapping his dick on my tongue and I liked making him
happy. He rubbed it all over my tongue and across my lips and then stuffed
it into my mouth. I closed my lips around it and sucked on the head while I
flicked my tongue on the sensitive underside and knew he liked it when I
heard him sigh and slightly moan. I pulled his cock out of my mouth and
said that's all for now Daddy.

He said, "Just a little more my sweet gurl," before placing his hand on the
back of my head and guiding it back down on his now hardening cock. I
worked my lips up and down his shaft a dozen or so times before pulling off
and standing up to kiss him. I really wouldn't have minded finishing him
off but I knew he would not be able to go again after our night out. At his
age he could cum but then he'd be done for at least twelve hours. We had
had dates before where we fucked and he came, we went to sleep, woke up in
the morning and he couldn't even get a hard on despite me sucking on his
dick for half-an-hour. I didn't want to chance it and was looking forward
to a passionate night of lovemaking before I was going to let him bust his
nut.

He put his softening penis away and zipped up. He took a drink from his
wine glass and took one last toke from his bong and we were out the door to
the restaurant. Richard opened my door and helped me up into the cab of his
big pickup truck. We caught up a bit on the ride to dinner and he told me
how much he had missed being with me. I told him I missed him too and that
I probably should have agreed to meet him sooner but I was still hurting
from my breakup. He assured me he'd always be there for me for whatever I
needed and I thanked him and told him how much I was looking forward to our
night together. He smiled and said we were on the same page as we pulled
into the valet.

Now I still get nervous being out at a nice place like the one we were
headed to. I'd been there before and always think everyone is looking at me
and wondering why this younger (perhaps trans) woman is with this much
older man. Richard is really good at calming my nerves. He engages so well
with the wait staff and is constantly complimenting me to them, they always
end up being so nice to us, I'm sure the big tips he always leaves help too
but I genuinely feel like a pampered princess when I leave that place.

Our meal was delightful and after we wrapped up we took the short walk over
to the theater for our movie. Richard loves action movies and we watched
Equalizer 3 with the super hot Denzel Washington. I don't really care for
those kind of moves, I love me a RomCom when it's my turn to pick. I
actually don't mind when Richard picks because he actually is into watching
the movie rather than trying to sneak a feel of my boobs or snaking his
hand up my skirt to play with my clitty like he always does when I pick the
movie.

We settled into our seats, the big comfy ones that you can put up the arm
rests, and I immediately snuggled up with my head on his shoulder. Richard
put his arm around me and pulled me tight. I felt so safe with him and
honestly couldn't wait to get back to his place to give him the pleasure I
know he was looking forward to.

After the movie ended we walked hand-in-hand back to the restaurant to pick
up his truck at the valet. We got in and headed back to his place for what
I was looking forward to most. As we pulled out of the lot I peeked over at
Richard and he had pulled his cock out thru his zipper and was stroking
it. I didn't need an invitation and quickly undid my seatbelt and worked my
way over into his lap.

He sighed as I took his rapidly hardening dick into my soft hand and gently
worked the shaft up and down. And he let out an audible moan when I
engulfed the head with my warm mouth and began to suck it. Luckily it
wasn't a long drive home and we were soon in his driveway, me still with
his cock in my mouth, and him telling me he couldn't wait to bury his meat
deep in my sissy garden.

I released his dick and Richard exited the truck and made his way to my
door, opened it and helped me down from the cab. He held my hand and led me
to his doorway. After opening it, he let me enter first and then asked if I
wanted another glass of champagne. I told him I would and he came back with
two flutes. We toasted to all the fun we were about to have and then he sat
down on the couch and motioned for me to come sit on his lap.

I crawled up on top of him, my knees to each side of him and lowered my big
booty right down on his still hard cock. I placed my arms around his neck
and leaned back a bit, grinding my ass on his crotch. He pulled me back
close to him and began to kiss my neck and then my mouth, our tongues
dueling in my mouth. He then pulled my sweater off and lifted my blouse
over my shoulders and tossed it to the ground. Richard loved to suck on my
nipples and I absolutely adore it when a man who knows what he's doing pays
attention to my tits.

He went to work on each nipple until they were both standing at
attention. He cupped my little breasts and drove me crazy with his expert
manipulation, both with his fingers, pinching them ever so roughly and his
lips, sucking them until they felt like they were going to burst. I just
kept grinding on his as hard as I could, trying to repay him for the
heavenly pleasure he was giving me. Finally, I told him I wanted to suck
his cock again.

He just laughed and said, "Not yet baby, Daddy isn't done pleasuring his
little gurl."

Richard was ready to move to the bedroom and asked me to lead the way. I
slid off him to the side and he stood up, offering me a hand back to my
feet. I accepted and once I was upright I tugged at his hand as I walked to
his bedroom. Once inside, I unzipped my skirt and let it fall to the floor,
kicked off my sandals and laid down on the big bed wearing just my pink
cotton thong. My clit was rock hard and I caught Richard just staring at it
as it strained against the tight fabric of my panties. I ran my long
fingernail along it and cooed as I fell the electric shock course through
my body.

Richard stripped naked and laid down beside me on the bed. He kissed me
gently and then more forcefully as I reached down and began to stroke his
cock again. He disengaged and crawled down between my legs, pushing them up
towards my chest a bit. He took my hard clit into his mouth and began to
work his magic as he teased my sissy pussy with his fingers while working
my clit with his mouth. I began to writhe in ecstasy as he slipped more
fingers into my tight hole, all the while sucking my clit and tonguing my
little balls. I felt like I was going to explode.

As my breathing got heavier and my body continued to involuntarily shake
Richard sensed my orgasm was building and quickly stopped everything. He
told me how amazing if felt to be inside me when I orgasm and how that is
what he's been looking forward to most. I asked him how he wanted to fuck
me and he told me to stay on my back. He pulled me to the edge of the bed
and placed his fat six-inch cock against my loosened rosebud. He gently
started to inch his way in but there was little resistance. He found
himself buried to the root in just a couple seconds and then he started to
work on my clit again.

As he thrust his dick in and out of me, Richard stroked my clitty slowly
and firmly, building up the pace as he quickened his penetration of me. It
wasn't long before I was screaming and he just slammed himself in as deep
as possible as my clit erupted and I squirted my cummies all over my belly
and tits. Richard just groaned as my sissy twat spasmed, clenching onto his
hard cock as I moaned out my climax.

Richard allowed me to relax a bit as I came down from my earth-shattering
orgasm. He just caressed my sides and hips as he remained still with his
dick bathing in the warmth of my wet sissy snatch. I finally caught my
breath and looked up at my powerful older lover, staring into his lustful
eyes I thanked him and told him how much I loved being with him. He told me
it was his pleasure and that he wasn't done with me.

I then realized I had shot a massive load. There were ropes of cum across
my boobs and a big puddle right above my now-soft clitty. I knew how much
Richard loved to taste my juices so I told him he should clean me up. He
smiled and pulled his hard dick out of me and bent down and began to lap up
my cum. He then moved his head up above mine and shared my nut with me as
we kissed. It tasted sweet and was so damn sexy. I knew it turned on
Richard as well because he was whispering in my ear to get into doggy
position.

I hopped up on my knees and elbows and readied myself to accept his hard
cock back into my body. He pulled me back to the edge of the bed and began
probing my sissy twat before pushing his way back into me. It felt great
and I began pushing back into him, out bodies meeting, slapping together as
he shoved his cock as far as it would go. Richard is a bit older and he
can't go for long periods of time so we usually finish with me on top of
him. After he hammered me as hard as he could for about three minutes it
was time for me to mount him.

He laid on the bid and pointed his hard cock straight up and motioned for
me to sit my big ass down on it. I faced him and placed his cockhead
against my sloppy pussy and sank down on it as he sighed. Richard really
liked when I would get his cock all the way in and just rock my hips
forward and back. The friction, he said, was amazing and it usually made
him cum within a few minutes. This time was no exception, after about five
minutes of my grinding on him I felt him start to tense up, his hands began
to push my hips back and forward faster and faster until I felt him grip me
tightly around my waist and he told me to stop.

He exploded deep inside me. Richard growled out how amazing my pussy felt
wrapped around his cock. He said it was like a velvet envelope that fit his
dick perfectly. I leaned forward and kissed him deeply as I started to rock
just a bit, tickling his sensitive cock as it softened inside me. He bucked
a bit at first but as the sensitivity lessened he began to thrust again
slowly until his flaccid dick plopped out of me allowing his nut to leak
out of my worn out sissy twat.

We just laid there for a while, totally exhausted. Eventually, after a lot
of kissing and cuddling, we made it to his shower where we soaped each
other up and rinsed off. He asked me to stay the night and as much as I
really wanted to at this point I decided against it. I didn't have any of
my things I needed and I didn't have a change of clothes for the morning.
He persisted but finally gave in and ordered me an Uber back to my hotel. I
got dressed and thanked him for a great evening, saying we should do it
again soon. He agreed.

I headed out when the car arrived and had an uneventful ride back to my
place. It was about 1 a.m. and I was worn out. I washed my face and brushed
me teeth and fell asleep right away. What a crazy day I thought as I tucked
myself into bed, two amazing men in one day, what would tomorrow hold?