Date: Tue, 7 Nov 2023 09:56:15 -0800
From: Tiffany Cox <tiffanytvslut@gmail.com>
Subject: Tiffany on the Rebound pt. 4

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

Part 4: The Weekend

As I walked back thru the parking lot I saw Manny walking. He was a big
man, probably 6'3" and close to 300-pounds. He was in imposing fellow but
such a sweetheart and he looked so handsome in his uniform. He offered to
carry my bag for me but I told him I was ok. He complimented me on my
outfit, a pair of tight jeans and a t-shirt with a light pink zip up hoodie
and white converse. I knew it wasn't anything special but it was still
super cute of him to be so nice.

I knew what he was doing but I was totally wiped out. I let him know I had
plans and wasn't available that night. He looked so disappointed I felt
bad. We were almost to my door and I couldn't let him go away all sad. I
told him I had a really fun time with him and wanted to spend some time
with him again, it just couldn't be that night. His eyes lit up a bit but I
could still tell I had dashed his hopes in the moment.

"Manny, thanks for walking me to my door," I said thanking him, "Do you
work tomorrow?"

"No, I'm off on Sundays but I could come visit you if you want," he said
with hope in his voice.

"Ok, let me see, I may have plans in the afternoon and evening," I told
him. "Could you come by in the morning, maybe around 10 a.m.?

His eyes brightened, "Yeah, that would be great, Do you like football, my
Rams are playing the Patriots at that time, we could watch the game if you
want."

"Stop it," I said pushing him playfully, "I'm a huge Patriots fan, I have a
giant crush on Tom Brady, haha. That will be fun and I'm sure we can find
some other fun things to do during the game."

He blushed when I winked at him, he was such a nice guy.

"I, I, I'm sure we can," was all he could come up with.

I gave him a quick peck on the cheek and told him thanks for being such a
cutie as I headed into my room.

I spent the rest of the night just chilling and tending to my "injury"
while I binged Sex in the City and scrolled thru my social media and looked
at comments and messages from my profile. I hit the sack early and got
another great night of sleep. The day "off" was a huge help, I was still a
little sore but nothing like the day before. I was looking forward to Manny
coming over and the fun I'm sure we'd have.

I also had a couple guys lined up from the dating site. One was a new guy
who was a manager of a car restoration business one city over. He told me
he wanted to take me for a ride in one of the cars they had just finished
working on, it was a 1968 convertible Camero. He was super cute and had
been a total gentleman in our conversations over text. His name was Jon but
with no H.

He had said how much he enjoyed the videos that Jesse had posted of us but
made it clear he was not expecting anything just because we were going to
meet up. Like I said, what a gentleman. I'm sure he probably knew I was
about as sure a thing as there ever was but he treated me with the utmost
respect and I appreciated it.

I also had a late night date with Heath. He was one of the most dominant,
degrading and hung guys I had ever been with. He made me do things that
pushed my limits but it was always so exhilarating when I spent time with
him. He always surprised me in a good way but he could also be scary
because I never knew what was coming. He couldn't meet until after he got
off work at 10 p.m. so I knew it would be a late night, good thing I got
such good sleep the last couple nights.

Anyway, I wanted to look cute for Manny so after my morning shower and
shave I got to work on my makeup. I did my face in a bit heavier fashion
than he saw me in the day before. I did dark eye shadow, heavy liner with
cat eye touches outside of each lid and put on a deep red lipstick. I
applied my thickest, longest fake lashes and styled up my long curled
brunette hair. I put on a pair white cotton boy short panties with pink
lettering on the back that said Daddy's Girl and covered those with short,
short daisy dukes with frayed edges. The shorts were super tight and showed
off my thicc cheeks nicely. I pulled on my knee-high Patriots socks with
the old Pat Patriot logo on them and added some cute black booties. I
hooked a white cotton bra over my little boobies and finished the look with
my #12 Tom Brady jersey tied up in a bitch knot at my waist. I looked in
the mirror and was happy with my look. I hoped Manny like it too.

At about 9:30 a.m. I got a text from him, "U ready baby? I'm heading your
way."

I texted back a selfie of me in my Pats outfit and told him I couldn't wait
to see him.

"U r sooo fuckin hawt Tiffany other than the ugly jersey lol," he answered.

"It will look pretty good when its crumpled up on the floor tho," he
followed up.

"LOL," I answered.

Not 10 minutes later I heard a knock on the door and it was my cute
security guard. I kissed him on the lips as he entered and we hugged
intimately. He was wearing an Aaron Donald jersey and athletic shorts and
flip-flops. He said he loved my shorts and that they made my ass look even
better than before. I told him thanks and offered him some water. We sat
down on the couch and started watching the pre-game show that was wrapping
up. I slid in close to him and laid my head on his shoulder while he
wrapped his arm around me. We chatted and joked about whose team was going
to win and made a bet. If the Rams won I would have to wear a Rams jersey
for our next date and if the Patriots won he would have to wear a Patriot
jersey for our next date. Neither of us wanted to lose that bet.

As we snuggled I looked up at him and he knew I needed to be kissed. He
leaned his head in towards mine and our lips met softly. It was apparent he
really wasn't that experienced but that was fine with me. I took the lead
and pushed my tongue into his mouth before pulling it back and letting him
take over. He pushed his tongue into my mouth and I intertwined mine with
his. As he withdrew I gently nibbled on his lower lip and he returned the
favor to mine. As he pulled away ever so slightly, I gazed into his eyes,
biting my lower lip and smiled at him before telling him just how big and
sexy he was. He got all flustered and started trying to compliment me about
how good a kisser I was and how he had been thinking about me non-stop
since he first saw me in the window getting fucked. He was stammering and
getting all handsy but it was actually refreshing and cute how bad he was
at this. I thought he was sweet and in contrast to all the guys who just
want to fuck and that is it, I was happy to help him work on his "game."

I grabbed his hands and tried to settle him down a bit. I slipped my hand
behind his head and ran my long nails thru his hair as I "shushed" him.

"Thank you baby, you are the sweetest ever," I told him, "relax and take a
breath love."

I dove back in and kissed him as I climbed onto his lap. I could feel him
underneath me, as hard as can be. I grinded on him as I wrapped my arms
around his neck and hung back. He broke our kiss and began kissing my neck,
ravishing me. As he was kissing and sucking on my neck, Manny moved his
hands to my tits and lifted my bra over them before pinching my nipples and
massaging my budding breasts. I cocked my neck and kissed him on the
forehead and told him to kiss me.

Manny kissed me deeply as I reached down as I pulled my jersey up so give
him access to my boobs. Manny moved him mouth down to my nipples and sucked
on each of them, sending shivers down my spine. He reached under my ass and
lifted me up a bit before standing up. Now I'm a big gurl so this was very
impressive to me and I just held on around his neck as I kissed him
again. He carried me over the the dresser and set me down in a sitting
position. I began stroking his hard cock thru his shorts before I tugged
them and his underwear down, freeing his fat dick from its confines.

I grabbed it and began to stroke it as he leaned back in for another
kiss. I pushed him away for a moment and told him, "Look the game's
starting, I don't want to miss Brady throwing a TD right at the start."

I don't think he thought it was very funny, haha. He stepped back and
looked disappointed again. I told him I was just kidding and knelt down on
the ground in front of him as he sat down on the bed. I took his dick in my
hand and stroked it, pulling his foreskin back as I looked up at him and
told him how much I had been looking forward to feeling him deep inside my
sissy pussy.

"Sissy pussy, what do you mean by that," he asked.

"Uh oh," I thought to myself, "this guy has no idea I'm not a CIS girl."

I was fully clothed when I gave him head the other day, he couldn't see my
genitals from the window when he saw me getting fucked, he didn't pick up
that I might not be a girl when we walked thru the parking lot on my way
back from the store (yay me on that one--I knew I was getting more and more
passable all the time) and he hadn't felt my hard clit thru my shorts when
I was just grinding on him. Crazy.

"Well darling, I'm a transgurl. I used to be a boy but I've been living
full-time as a gurl for the last couple of years," I explained to him
hoping he wouldn't get upset.

"Oh my gosh, I had no idea," he stammered. "Can you still have sex?"

"Yes, I can still have sex silly," I told him, "I just have my sissy pussy,
my ass for you to fuck."

"And you have a cock, like me," he asked.

"No," I said, "my cock, or as I like to say my clitty, is nothing like
yours. Yours is big and thick and mine is very small and petite. Very gurly
actually."

"Can I see it," He asked.

"Sure baby," replied as I stood up and moved to the bed next to him.

I undid my shorts and unzipped them and shimmied them down my legs. I
rubbed my bulge in my boy short panties and let him see the outline of my
clit before I rolled over onto my. Knees so he could see the writing on my
backside.

"Daddy's Gurl, eh," he said. "Does that make me your daddy?"

"If you want to be Daddy," I cooed.

I slipped the panties down a bit and rolled back over and took my 5" clit
in my hand and began to stroke it. He just sat there in shock as I wiggled
and thrust my hips while I worked my hard little clitty. I could feel the
beads of precum gathering at the tip and smeared them all round the head,
making it super slick. I then brought my fingers to my mouth and lapped up
the remaining gurl juice, it was delicious.

Manny was staring so intently as I pleasured myself, I could tell he was
turned on. I grabbed his hand and brought it to my clit and asked him to
gently rub up and down the shaft. He was a bit hesitant but relented and
engulfed my thin little clit. His hands were so much bigger than mine, the
little head sticks out when I grab the shaft, with Manny's hand there was
no sight of it, the head was down in his palm.

I started to thrust my hips into his closed hand and it felt amazing, I was
moaning and writhing. I glanced up and saw him stroking his cock while he
stroked mine. I motioned for him to bring his dick to my mouth so I could
continue sucking on it. He rearranged himself and soon I was back to giving
him head. I felt myself getting close to cumming so I wriggled away from
his grip and released his dick from my mouth. I told him I wanted to feel
him inside me now. He agreed that he wanted to fuck me and I pulled my
shorts and panties all the way off and got on my hands and knees facing the
TV. Hey, I wanted to watch the game too, lol.

The Pats had the ball and Brady was moving them down the field. I told
Manny they were going to score, just like him and he laughed before telling
me they were going to get stopped. He got up on the bed behind me and I
felt him clumsily rubbing his cock around my hole. I spit in my hand and
reached back between my legs and rubbed it into his throbbing cock. I
brought it back and spit again and massaged it into my, much less but,
still sore sissy twat and then guided his cock to my opening.

I rocked my hips back while coaxing him to push forward by grabbing his
balls and pulling them towards me. He got the message and began to stab
forcefully. I told him to relax and push gently, to just let it slide in. I
fondled his balls as he finally got the hang of it. Just then, LaGarrette
Blount broke a 43-yard TD run only a few minutes into the game and I told
Manny to get ready for a lot more scoring. I don't think he cared, this may
have been the first time he ever got laid and he was enjoying the warm and
wet welcome of my dick garage.

Manny began to pump his fat dick in and out of me and he was breathing very
hard. Again, I knew he wouldn't take too long and within a couple minutes
he was grunting out a powerful orgasm. He clenched my hips and hammered
away until he was totally spent. He collapsed on top of my back, heavily
breathing, and said that was amazing. I told him he was even with Brady,
one score each, lol. And that I was losing so far since I didn't get to
nut. I told him I was just kidding and that I was sure I would get to enjoy
a great climax at some point that day.

He was such a docile giant, he pulled out of me and laid back on the bed. I
nestled in close next to him and we watched the game as he stroked my
forehead and cheeks with his big but gentle hands. I periodically leaned
over and kissed him on the cheek or on the lips if he met my lips with
his. We watched about a quarter of football before Brady struck for a long
TD pass to Chris Hogan. It was 14-0 and I told him he better start shopping
for a Pats jersey. He just laughed and said the Rams were only down one
since they were favored by 13. I feigned surprise since we hadn't agreed on
a point spread but I really didn't care. I said, "fine, they're going to
win by way more than this anyway."

The Pats added a FG right before halftime and the score was 17-0. I was
gloating as I lay there snuggled up with Manny in just my Brady jersey,
shoes and socks. I tried to ease the blow by lightly tickling his balls
with my long finger nails. I could tell he liked it as his breathing
deepened and I could see his cock starting to get hard again. I peeked up
at him and asked if he was ready for another round.

"Yeah baby," he eagerly replied, "I want to fuck you again, it feels so
good inside you."

With that I took the lead and moved my head down to his crotch where I
began by sucking on each of his balls, licking them firmly as I held them,
one-by-one, in my mouth with my lips. This had him rock hard before I even
got his dick in my mouth. I released his second ball from my lip grip and
licked from the base of his cock to the head with just the tip of my
tongue. His dick spasmed as I repeated this a couple times. I peeled back
his foreskin and rubbed the head across my lips before I spit on it and
swallowed his entire cock down to the root. I knew he would last longer
this time, I just didn't know how long.

Manny placed his hand on my head before quickly removing it. I looked up
and him, released his dick and told him it was ok if he wanted to guide
me. He put it back on my head and pushed me down just every so slightly. I
worked his cock for a couple minutes before asking him if he was ready to
fuck me. He acknowledged he was ready and I rolled over to my back and
spread my legs. He kneeled between then and placed his swollen cock head on
my rosebud and gently eased his way into me ... hey, this boy was learning.

I wrapped my legs around him and began to lift my hips a bit to meet his
pumps. I could see the pleasure on his face, his eyes were closed and his
head tilted back as he thrust his fat cock in and out at a steady pace. I
reached up and rubbed his chest with my hands, threading my long nails thru
his thick chest hair. I then moved them down to his ass and pulled him into
me harder. He got the message and began to slam in and out of me in a much
harder manner. I reached down and began to work my clit a bit and got it
hard.

Manny saw my hard clitty bouncing around and grabbed it in his hand while
he continued to fuck me. I pulled him down and kissed him. I told him I
loved being his gurl and I was very happy we were able to enjoy each others
bodies. He sat back up and sped up his pace, both on my clit and on my
cunt. I was just getting into it when I felt him clench up and I knew he
was about to fill my pussy with his cum once again. His face got distorted,
his body jerked a few times and he released my hard clit from his hand and
grabbed me by my waist as he convulsed and spewed his babies into my tranny
womb. I squeeze my sphincter as tight as I could and told him how amazing
he felt as he unloaded inside me. I had been close yet again but could not
get over the finish line myself. The problems of a young, inexperienced
lover. I guess we take the good with the bad. He was such a sweetie I
couldn't be mad at him.

He was still panting when he laid his body down on top of me, his head on
my shoulder and his left arm across my chest with his palm over my right
tit. I stroked his hair and cheek, kissing him intermittently as he caught
his breath. We lay there like that until halftime ended, him atop me, his
cock still inside me and us exchanging darling little kisses every minute
or so. He had just nutted in me no more than 10 minutes before and I could
feel his dick starting to harden again, still inside of me.

I asked him what he was doing as he began to rise back to his knees and he
just said he was ready to go again. I was shocked.

"How old are you again," I asked.

"21, how old are you," he replied.

"46," I said sheepishly.

I knew he was young but didn't think he was that young. "Damn," I thought,
"I guess we're going for round three then huh?"

He didn't say anything but he did start to slowly pull himself right to the
edge of my cunny, with just his head still inside me. He pushed back in and
I heard an awful sound. The gurls know what I'm talking about. As he pushed
his cock back in, my well-used pussy, full of his seed, made the loudest,
wettest fart sound. I was horrified. I think it took Manny by surprise too
but he got a good chuckle out of it as I recoiled in horror. It was the
same thing the next 10-12 pumps, as I tried to readjust to make it
stop. Manny couldn't have cared less, he just fucked away, lost in the
pleasure he was feeling. I finally got to a point where I got the noises to
stop and I finally could relax and enjoy the fucking I was getting.

It didn't take long for me to get back to the brink, I had been on the edge
twice already and my clit was oozing again, ready to burst. I was tweaking
my nipples and trying not to touch my clit, it wasn't going to take much to
make me pop. Manny saw me working my nipples and brought he head down to my
left one and sucked on it. If felt amazing. My clit was now rubbing up
against his stomach as he leaned down, I was afraid he was going to make me
cum and I really wanted to make it last a little longer considering I
thought he would take longer since he'd already came twice.

I pushed him up and asked him if I could get on top. He agreed and rolled
over onto his back. I mounted him and guided his cock to my hole and sank
down on it slowly until it was balls deep. I rocked forward and back on it
and could tell Manny really like that. I leaned in and kissed him as I kept
grinding on his cock, he grabbed my tits and squeezed them before wrapping
his arms around my back. He held me tightly and began to pound his dick up
into me. He said my pussy felt great and he just wanted to fuck me all day.

My clit was trapped between our bodies and I knew I was gonna bust. I had
so much sexual energy stored up and it came crashing out in waves as I
coated our stomachs in sissy cummies. Manny kept hammering away as I lay
there spent but it wasn't long before he splattered my insides with another
torrent of white hot man sap. We lay there, him still inside of me after
two nuts now, our bodies coated with my cum, in a deep embrace, locked in a
kiss. It was such a beautiful scene.

I finally slipped off of him and felt his cum rush out of me onto the
bed. "Guess I'm going to need housekeeping today," I thought to myself. I
was totally satisfied. My legs were still shaking a bit, my heart still
racing and I had yet to fully catch my breath. This young man who had no
idea what he was doing had given me one of the best sexual experiences of
my life. I have always felt a greater connection to the sweet guys even
though I've had much more memorable sex with aggressive dominant guys. I
don't get it but I guess I don't have to.

I kind of drifted off as we lay there entangled with each other and before
I knew it I looked up and the game was over. 26-10 Patriots was the score.

"I win, I win," I shouted, startling Manny.

"Sure, whatever," he replied, "I'm the clear winner today," he said as he
pulled me in for another long deep kiss.

"What a sweetie," I thought to myself as he held me in a tender embrace.

I told him what a great time I had with him and said I had to get ready for
some afternoon plans with a friend. He asked if it was a guy and I lied and
told him no, it was with a gurlfriend and that we were going shopping. I
think he bought it but wasn't totally sure. He was getting attached and I
had to be a little careful. He was way too young for me and even thought I
knew I wanted to keep him as a friend with benefits I was wary he might be
too clingy at this point.

I told him to go ahead and shower if he wanted to, that I would go after
him. He said he was good ... ah, that's pretty gross ... and got dressed
and came over to kiss me goodbye. He asked if I would be around tomorrow
and I told him I was checking out first thing in the morning. He
volunteered to come buy before then to give me a fun sendoff. I told him I
had to work that day and wouldn't be able to do much in the morning. He
asked when he could see me again and I told him perhaps later next week or
the following weekend. He said he would keep in touch via text and was on
his way.

I got in the shower and cleaned up, shaved my legs, underarms and my bikini
line. Once the maintenance was done I just relaxed in the steamy shower as
the hot water washed over my smooth body. I couldn't stay in as long as I
wanted because I was expecting Jon in about an hour. He was picking me up
and taking me to his showroom where we were going to check out some of the
cool cars they have and take the Camero for a spin.

I'd been subdued with my outfits so far this week, I wanted to wear
something really cute and gurly for this date. I picked out a super cute
army green cargo skirt that was probably a little too short truth be
told. "Oh, well," I thought as I held it up in front of me. It was one of
my faves and I hadn't had a chance to wear it yet. I paired it with a
darling little cream long sleeve v-neck shirt that was a little tight but
showed off my perky boobies very nicely. It was long enough to tuck into
the skirt and I wore a metal loop belt to compliment the look. I slipped on
a black thong and matching bra before donning my ensemble. I finished the
look with some very sexy wedge sandals that showed off my cute painted
toenails. I added a silver anklet and a couple toe rings as well as my
silver "T" pendant and chain, big hoop earrings and silver bracelet with
dangling hearts. A few rings and I was ready to go. I almost forgot, I had
done my makeup just about the same as I had that morning before Manny came
over.

I poured myself a big glass of Tito's and cranberry and relaxed as I waited
for Jon to show up.

"Hey baby, I'll be a few minutes late," read the text from Jon, "traffic is
awful, can't wait to see you beautiful."

Well, I guess I had a little more time to check out the late games and sip
my cocktail.

"Ok, almost there," read the next text, about 15 minutes after he was
already supposed to be there. "Hope you're ready to go."

"Yep, I'm ready," I texted back. "What are you driving?"

"grey silverado," was the reply.

"K, 1822" was all I sent back.

I polished off my giant drink and grabbed my dainty little backpack and a
cropped white denim jacket incase I got chilly and headed out the door. I
saw him pulling in and waved him down as he crept towards me, looking for
my room. He rolled down the window and gave me a funny little wolf whistle
as I strutted towards his truck. I pulled the door open and climbed in
while he was clearly undressing me with his eyes. I slid in and leaned over
to give him a light kiss, he met me in the middle and we locked lips
briefly before I closed the door and fastened my seatbelt. We were off.

It didn't take too long to get to his work, maybe 20 minutes by side
streets. It was an amazing building with all kinds of cars in various
states of renovation. He showed me around and took me to see his office. It
was really cool, he had pictures of him with a bunch of famous people,
athletes, actors and politicians whose cars they had worked on.

I was also very impressed by Jon's physique. I had seen pictures and knew
he was handsome and in great shape for his age, about 55-60 by my
estimation. What really struck me was how solidly he was built. He had to
be 6'2" at the least, I was in 4" wedges and I'm 5'10" with out heels and
we were about eye to eye. He also filled out his jeans very well, he had a
great ass and a very nice bulge in the front. His broad shoulders and
chiseled jaw line, highlighted by a very short, more like stubbly beard had
my engine revving.

As I followed him around the enormous facility where they worked on all
these cars I heard him talking about some of them but really wasn't
listening to what he was saying. I was fantasizing about him bending me
over the hood of one of them and fucking my brains out.

"Do you want to take a quick spin," I heard his say, jogging me out of my
daydream, "I can grab the keys to the convertible and we can cruise down
the beach if you want."

"Ummm, sure," I responded. "Let's do it."

Jon ran off for a minute and came back with the keys. He opened my door for
me and complimented me on my "very sexy legs" as I slid into the seat. I
looked up at him and thanked him as I stared up into his eyes. He may have
sensed I was turned on because he dipped down towards me and we met in a
very deep kiss. He placed one hand behind my neck and held me there as he
explored my mouth with his tongue. I just sat back and enjoyed it. He
finally stood back up and closed my door and circled around to the drivers
side.

He ripped out of the facility like a race car driver, burning out as we hit
the street and sped off towards the ocean. We turned onto PCH and he
accelerated up to almost 100 MPH. It was exciting but a little scary. He
was a very good driver so I calmed down and relaxed as we cruised along the
beach.

After a few minutes he reached over and placed his hand on my left thigh. I
slightly opened my legs so he could feel the soft smooth skin of my inner
thigh if he wanted to. He took the hint and began to stroke my leg softly,
almost like he was trying to tickle me, as we continued to chat about the
surroundings we were speeding by.

I eventually reached over and put my left hand on his right thigh,
spreading out my fingers and curling them as I pulled my long nails over
his jean-covered leg. He adjusted himself to move slightly closer to me so
I turned my hand over and brushed it across the growing bulge in his
jeans. He took advantage as well and slipped his hand under my skirt and
cupped my little soft clit and balls. He lightly gripped my genitals and my
clit instantly started to harden. I let out a little gasp and he knew just
how turned on I was. I could feel him hardening as well but he was trapped
inside those well fit pants. I, however, had an easy answer to my
dilemma. I slipped my thong to the side and gave him full access to my sex.

Jon fondled my little dick as he sped back toward the shop. I laid back and
enjoyed his manual stimulation. By the time we were pulling into the
facility I was leaking pretty heavily. I pulled my thong back over my
clitty and balls and prepared to walk back into the office after we
parked. Jon leapt from the driver's seat and ran around to open my door for
me. He helped me to my feet by offering his hand. I loved how gentlemanly
he was. I took his hand and walked to the door with him, he unlocked it and
held the door for me and we headed for his office.

Once inside he asked if I wanted something to drink, I declined and told
him all I wanted was to please him. He blushed a bit but we both knew what
we were there for. We tore at each others clothes as we kissed madly. He
had my shirt and bra off in one fell swoop, lifting both over my head at
the same time. I pulled his polo shirt over his head as well and went to
work on his belt. It was tight and with my long nails it was hard. He
reached down and opened the belt and unbuttoned his jeans. I grabbed his
zipper and lowered it as we continued to kiss passionately.

I slipped my hand into his underwear and felt his steely manhood pulsating
in my palm. It was pretty big and thick just like he promised. I shouldn't
have been surprised, he had sent me a dick pic with his cock along side a
Red Bull can and his dick was slightly bigger in girth and a full inch or
so longer. I squeezed it a bit as he had moved his attention to my neck,
kissing and sucking on it and my collar bone. Jon told me he had been
waiting for this moment the past couple days and was looking forward to
pleasing me. I just lightly moaned and guided his head down to my little
hard nipples. He licked them both quickly and then suggested we move to the
sofa across his office.

I shook my ass for him as I strode over to the couch, exaggerating my walk,
swiveling my hips with each step as I made my way in just my skirt and
heels. I shook my hair out and pushed it over my left shoulder before
getting stopping just short of the seating area. I spun around and asked
Jon to remove his jeans. He kicked off his loafers and slid his jeans down,
underwear and all, revealing my prize, a very fat, perfectly proportioned
circumcised penis. It looked to be about 8-9 inches and was clean shaven. I
asked him to sit down but he told me he wanted to do something for me
first.

He pushed me down and had me lay on my back. He nestled in between my legs
and pushed the back toward me lifting my ass up off the leather. He began
to kiss my pussy and was licking all around the opening to my sissy
garden. I felt his tongue as it entered me, probing my box, searching for
my pleasure buttons. As he firmly licked away at the top of my twat I began
to moan a bit and was arching my back.

"Mmm, there's your spot baby," he said before diving right back into my wet
hole. He focused on that spot for a few minutes and I was wiggling under
his touch, moaning out how good it felt.

"Yass daddy, lick my sissy pussy," I screamed as he continued to furiously
work on my pleasure point with his masterful tongue. He then slipped in a
finger, then a second and began to open me up. I was leaking even more now
but with me just cumming a couple hours before I knew it was going to take
a lot more to push me over the edge again. I told Jon how great he was at
oral but that I wanted to make him feel good too. I begged him to let me
suck his cock. He kept at it though and even took my hard little clit into
his mouth. It felt wonderful but I really need his dick. I pulled his head
up off my dicklette and motioned him up to me. I kissed his lips and told
him it was my turn to please him. He finally relented and stood up in front
of me. I sat up and began to kiss his cock. I gazed at it like it was a
work of art. Hell, it could have been, it was a thing of beauty.

I licked the underside from root to stem and finally took it into my mouth,
locking my lips around the head while my tongue worked its magic. Jon was
just staring down at me when I took a peek up at him. He had his hands on
his hips with them thrust forward like he was trying to make his perfect
cock look even bigger. I stared back at him as I worked my lips further
down the shaft before pulling back until just the head was covered.

Just as I was getting into a good rhythm I felt Jon pull back saying, "I
need to get this cock inside you baby."

I understood, I was aching to get fucked too and I told him to sit down. He
sat back on the couch and I stood up, pulled my skirt and belt up a bit and
slid my thong down my legs as I bent over in front of him. He started
running his hands all over my ass cheeks and was pulling at me to sit back
on him. I reached behind me and lined his cock up with my ass crack and
started to lift myself up and down in his lap, letting his cock rub my
crack but I wouldn't let him inside of me just yet. He was begging me to
let him fuck me but I just kept up my little teasing lap dance.

Finally I relented and spit in my hand and rubbed it over his cock as I
lined it up reverse cowgirl and lowered myself onto him. He pulled me back
onto his chest and groped my breasts while sucking on the left side of my
neck. He spread his legs enough so my legs were no longer touching the
ground. He had all the control now as he held me in place and began to
thrust up into my snatch with his rock hard cock. He moved one hand down to
my clit and stroked it as he penetrated me. His other hand was pinching my
left nipple. I was really loving how this was playing out. He was such a
thoughtful lover.

I asked him if he wanted me to turn around and he said yes so I expertly
spun around on him without his cock falling out. I settled in on top with
my knees straddling him on the sofa. I began to lift my hips up before
sinking back down until I was bouncing all the way up until only a few
inches were still inside me before slamming my ass back down, impaling
myself on his magnificent love stick. Jon just kept kissing me and licking
my neck and tits as his hands helped guide my pace as I rode his cock. I
was moaning and screaming how much I loved his big dick as he told me what
a sexy gurl I was.

He asked if I minded changing positions and I asked him what he had in
mind.

"I'd really like to fuck you doggy style baby," he said as I sat motionless
with his cock buried to the hilt in my sissy fuck hole.

"Sure love," I told him, "that is one of my favorites!"

I lifted myself off him and felt empty as I felt his cock slip all the way
out of me. I knelt down on the couch, propping myself up with my hands and
elbows on the top of the backrest. Jon came in behind me and lined himself
up to enter me. Now that I was loosened up, he slid right back in, his
entire length feeling my gripping muscles as I squeezed tightly as he
seated his cock in me.

"Oh yeah Tiffany, your pussy feels amazing," he told me, "keep squeezing
darling, I love it."

I moved forward then back, opposing his strokes. I threw that ass back at
him as he pushed forward and slid forward when he eased away from me. He
slipped out a couple times before we got the choreography down but I
reached between my legs and slid him back in each time. Once we found our
rhythm we moved in unison and it was unreal. He ended up adjusting his
angle a bit and I felt the sparks as he rubbed across my prostate. Maybe 30
seconds of constant stimulation had me shaking and I felt my hard clitty
explode as I climaxed without touching myself. It was the second time I had
achieved a hands free orgasm this week and it was just as remarkable as the
first one. It was a full body orgasm with shock waves traveling up and down
my spine. I also stayed as hard as a rock, something that never happens
when I cum via physical stimulation.

I think I may have scared Jon a bit with the loud screams of ecstasy as I
squirted out my nut. I shook violently before going limp against the back
of the sofa. He stopped thrusting for a second but got right back to work
when I yelled at him to, "Keep fucking me, don't stop daddy!"

Jon redoubled his efforts and really kicked his pistoning into high gear
now. I think he might have been getting close himself because he would
periodically stop fucking and pull his cock out and slap it on my butt
cheeks. I know guys who have done this before to try and hold off on
cumming. I told him it was ok if he was ready to nut but he said he wasn't
all that close yet.

"Really," I thought to myself, "Ok, yay for me, I get more dick!"

I tried to adjust myself now, to try to get the prostate stimulation that
had sent me into orgasmic bliss but I was struggling to find the right
angle. Don't get me wrong, the big fat dick slamming in and out of me felt
amazing but I was hoping to make this session a double squirter.

I asked Jon if he wanted to do missionary, I really wanted him to kiss me
some more and he told me that sounded great. He pulled out and grabbed my
hand, pulling me over towards his desk. He lifted me up onto it and held my
hand as I laid back, lifting my legs and spreading them to give him access
to my love tunnel. He pulled me closer to him and he reinserted his big
penis while standing. He had tremendous leverage and began to fuck me
really hard. I told him to kiss me and he dropped his upper body down and
rammed his tongue into my mouth. I placed my arms around his neck and held
on as he moved his hips forward and back, driving his big crank in and out
of me. He sat up and I held on as he lifted my back off the desk. He never
stopped fucking me as I clung to him.

I could tell the position was very tiring for him as his paced slowed to a
crawl. It felt really good as his cock crept in and out of me but it seemed
like he wasn't enjoying it as much. I suggested we move back to the sofa
and he agreed. He gave me a good slap on the ass as I daintily pranced over
in my high heels, my legs unsteady and shaking from the great sex this man
was giving me. I feigned shock as I whipped my head around and Jon just
laughed. I couldn't help but giggle too.

I could tell how much he like doggy so I just assumed the position and
looked back over my shoulder and beckoned him to "fuck my brains out
daddy!" He didn't waste a second and was back at it, pounding me just like
before and let me tell you, it felt totes amazeballs. He was sliding along
my prostate again, hitting the spot and driving me wild.

"That's it baby, right there," I blurted out. Keep fucking me, you're
hitting my spot!"

I was really close to cumming again and I really wanted him to pound
another one out of me. I stayed as still as I could and let him work his
dick in and out, concentrating on the one spot inside me that was engorged
and seemed ready to send more sissy nectar splashing from my clit. But,
before I could actually get there I felt Jon pushing deeper, guiding
himself against me as he started to moan. He quickly withdrew his cock and
started spraying his load all over my ass and back.

I urged him on, "yeah baby, gimme that cum lover."

I felt him lay his big dick in my ass crack as he continued to slide it
forward and back as he kept dribbling beads of cum onto my ass.

I asked him why he pulled out he said he didn't ask me before hand and
didn't want to cum inside me without my permission. He really was super
thoughtful.

I reached back and slipped his cock back in me and told him he was always
welcome to nut wherever he wanted with me. His cock was still super
sensitive and I really enjoyed making him squirm as I made little movements
that made him shake. I wiggled my ass for him before he finally softened up
too much and slipped out of me.

I told him how close I had been to a second nut and he looked at me and
said he was sorry. I told him how awesome he was and that it was ok, after
all, he had given me one of the best orgasms of my life. He asked if I
wanted to cum again and I told him sure but I had to be back to the hotel
pretty soon. I didn't think he could go again, could he? Nope but he told
me he wanted me to stroke myself while he watched. He could snuggle with me
while it worked my clit.

I sat back on the couch and brought my feet up to the edge of the seat. I
spread them and began to work my clit. It came to life immediately and soon
I was leaking. Jon began to tug at my left nipple and pulled my chin to the
side so he could kiss me. I told him I was getting close. He reached down
and started rubbing the inside of my thigh, I think he noticed how much I
liked it from our time in the car. This had me at the brink.

I looked into his eyes and he knew what was about to happen, he pinched my
nipple hard and kissed me deeply as my hips started to buck. I threw my
head back and moaned out uncontrollably as I began to squirt again. Each
powerful convulsion sent cum flying out of my clit and it splashed down
over my thigh and Jon's hand. It hit my stomach and then petered out with
it just oozing out of me and leaking down the shaft and over my balls. I
lay there, my eyes closed, my whole body spasming from the powerful orgasm
I just experienced. I could barely breathe much less move.

Jon lifted his hand up and said, "I think this is yours," with a laugh.

I cracked my eyes open just a hair and giggled as I surveyed his cum
covered hand.

"Looks yummy to me," I commented. "You should try it, mine is super sweet
and delicious."

"Oh really, you've tasted yours before," he queried.

"Of course, if you don't want it I'll take it," I said, pulling his hand to
my mouth.

He moved it to my face and I started licking it up like a hungry kitten. I
had gotten most of it when Jon wiped the back of his hand across my lips,
making sure I got all of it.

"You really do like it don't you," he asked, clearly surprised.

"I do, its super delicious."

I asked him for a towel to wipe off my back and ass before I got
dressed. He grabbed one and began cleaning up my backside.

"Uh oh, I hope I didn't ruin your skirt," he said. "There is a big wet
stain on it."

"Don't worry daddy," I told him, "other than it being embarrassing if
anyone sees me with a wet spot there, it's no big deal. It will wash out."

"Oh, good," he said, "I was worried there for a second."

I pulled my panties back on, adjusted my skirt into place, hooked my bra
back up and finally pulled my top back over my head and shoulders. I could
feel my pussy was still sopping but otherwise I was ready to head back to
my hotel. I slipped my jacket on, it was a little chilly outside now and we
got in Jon's truck for the ride back. We chatted on the 15 minute drive and
told each other how much fun we had and said we would make plans later that
month.

He pulled into the parking lot and stopped right in front of my room. We
kissed a bit and I got the feeling he wanted to come in, maybe for another
round. I told him it was such a fun day but I had to get some rest, I had
to work in the morning and I still needed to get cleaned up before bed. I
think he understood but I could feel the disappointment from him. I gave
him a quick kiss and opened my door. I told him we'd see each other again
soon and slid out of his truck. He waved as I headed to my door. I unlocked
it, opened the door and quickly shut it behind me. I was so close to
inviting him in but I knew I would have blown off my last date if he made
it into my room and that would cause more drama than I needed.