Tiffany On The Rebound By Tiffany Cox (tiffanytvslut@gmail.com)
Part 1: Wednesday
If you read my last story about my whirlwind romance with my dream guy Kai, I regret to inform you things eventually took a turn for the worse and he could not get over his family's reservations about me being a tgurl. I caught him in a few lies and wound up finding videos of him and his ex girlfriend having sex. It was a traumatic experience for me and left me reeling for the better part of a year.
I was sooooooo in love and we had such a great time together, I thought that we would spend the rest of our lives together in loving bliss. But, alas, it wasn't meant to be and after a few months of soul searching and keeping to myself as I embarked on my healing journey, I decided it was time to get back out there.
It had been a couple years since I'd been with anyone other than Kai and I was a bit hesitant to look for anything serious so I jumped on an old trans dating website I had a profile on and advertised my availability for the coming weekend. To no surprise I had a bunch of interest from old regular partners I'd known for years as well as some new exciting contacts that looked like they would be fun to get together with.
I decided to take a few days off and booked an extended stay hotel, from Wednesday to Sunday, to get away and just have some fun. I began to plot out my long weekend date schedule and the calendar started filling up fast. I had also posted my Kik handle on my profile and I was being inundated with requests (and dick pics...lol). I had forgotten what it was like to be so in demand after being in a committed LTR for so long.
Well, I decided to do the easy thing first and agreed to meet up with Patrick, an old friend with benefits who never fell out of touch while I was dating Kai. We hadn't been together in a couple years and I could tell he was excited to get together again. We planned a meet up at a seedy motel up near where he lived. It was about a 30 minute drive for me, we'd met there a dozen or so times before.
It wasn't the nicest place but the rooms were always clean and they rented them by the hour. I loved parking in the back of the lot, as far away from the rooms as I could, and taking my time strutting across the parking lot in my cute sexy outfits. Patrick loved seeing me show off in front of all the people just hanging out at the motel. I would get whistles and stares from the men and the evil eye from some of the hookers who were wondering who this white slut was, prancing thru their parking lot.
I swayed my hips as I confidently strode to room #6 where I saw Patrick standing in the doorway admiring me with a giant smile on his face. My ass, barely covered by the tight black ruched mini skirt that was so short everyone could see my stocking tops, bounced with each step of my sparkling black high-heel platform pumps. I surveyed the row of men on the balcony above our love nest clocking me and blew them a kiss as I approached the room.
"Hey baby, how much to do all four of us," shouted one of them. "We know how to treat a slut like you bitch!"
I just feigned being horrified, smiled and kept walking right up to Patrick. He greeted me with a sweet kiss and a warm embrace as he ushered me into the room and closed the door behind us. It didn't take long for me to be on my knees in front of him. This was our routine back when we were seeing each other regularly. I would give him head until he was rock hard and then he would fuck me until he nutted in me. Sometimes I would end up cumming before he did and it would usually send him over the edge.
I'm not sure if it was the fact that we hadn't seen each other in a while but he was raring to go from the start. He pulled his big eight inch black cock out and shoved it down my throat. He began to rock his hips and thrust his hard meat way back into my throat. He was telling me how much he missed me and how my sweet mouth felt amazing but he couldn't wait to get in my warm sissy pussy. I did my best to deep throat him but I couldn't help gagging a bit. I was drooling all over the place as he rammed in and out of the throat.
This was just what I needed.
It had been months since I had been with a man, since the night I found out that Kai was cheating on me and stupidly had sex with him after he promised it wouldn't happen again. Only a couple days before he broke up with me for good. It was good to know I was wanted and could still please a man.
I pulled Patrick's hard rod out of my mouth and stared up at him as I licked his balls tenderly as I stroked his manhood. I told him how much I missed him and how I was looking forward to getting pounded by him. He told me to turn around and get on all fours.
I did as I was told and he saddled up behind me, teasing my rosebud with the head of his massive dick. He rubbed it all over my hole and slapped it on my cheeks and sissy pussy as he told me how hard he was going to fuck me. I arched my back as I peered over my shoulder at him, urging him to impale me on his giant tool.
Patrick spit on my sissy twat and rubbed it in with the head of his cock before sinking it in, inch by inch until he was balls deep. I moaned out my appreciation as he began to slowly build up his strokes, in and out, as I adjusted to his girth. Within a minute or two he was hammering away at me with wanton abandon as I pushed my fat ass back to meet his thrusts, our bodies clapping and his balls slapping against my ass with each deep plunge. This doggy style assault went on for a bit, speeding up and slowing down before Patrick pulled out and had me lay on my back.
He fed me his cock straight from my sissy cunt and had me lick all our juices off of it before moving back between my legs and planting his cock back inside me. He looked down at my hard five inch clit and asked if I wanted him to stroke it. I told him he knew I loved it but that I may cum pretty quick since it had been so long for me. He smiled and said, "good."
I was in heaven as he slid back into me with zero resistance. His BBC pistoned in and out of me, long dicking me into submission as he pulled out until just the head remained inside me and than slammed it back in to the root. His hand reached out and started to tug at my hard little cock. He massaged it then stroked it in time with his thrusts. I was moaning loudly as I felt my orgasm approaching.
Patrick then slowed his pace a bit, allowing me to catch my breath. He asked me to beg him to make me cum.
"Please daddy, make your gurl squirt, please, please, please," I exclaimed.
He pulled his cock out of me and slapped it on mine asking, "How much did you miss this big cock you little slut?"
"I missed it so much baby, please put it back in me, please fuck me daddy," I pleaded. "I missed being your slutty fuck toy!"
He slammed it back in to the hilt, eliciting a scream from me, as he hammered away as hard and fast as he could. He was pounding my prostate and I knew I was about to pop. I told him I was gonna cum and he grabbed my clitty and stroked me as I exploded all over my tummy and tits. I was screaming out his name and how much I loved his big dick as the waves of pleasure cascaded over my body and my nut splashed all over me.
As I came down from my high I tried to get Patrick to slow his pace a bit but he wouldn't have any of it. He was in a frenzy as he thrust as hard and fast as he could, pushing my legs up higher over his shoulders to get a better angle to get as deep in me as he could. I pulled him in for a deep wet kiss, our bodies coming together, as close as could be as he jackhammered my pussy while we held our tight embrace.
He finally relented and pulled his upper body away from mine as he continued to fuck me. He slowed down a bit and saw my sissy juice puddling on my body. He scooped up some from my stomach and brought it to my mouth. I sucked it from his fingers and told him how yummy it was. This drove him crazy.
He redoubled his efforts on my sloppy sissy cunt and within seconds I could feel him pushing as deep as possible before he grunted out that he was cumming. He shuddered with each pulse as he emptied his balls deep inside of me. As he ejaculated into my sissy womb, I clenched my asspussy muscles to draw out every last drop of his nectar into my body. He finally collapsed on top of me, his cock still inside. I kissed his forehead and rubbed his back as he tried to catch his breathe.
"OMG baby," I told him, "that was amazing!"
He finally brought his face up out of my tits and kissed me and told me how happy he was now that I was going to be available to hook up again. He promised me many more nights like this and I smiled and said, "I hope so!"
He jumped into the shower and invited me in with him. It was little too small and I was ready to get back to my place where I had a nice big bathtub to soak in. I thanked him for a great time and started to put my outfit back together. After getting dressed and touching up my makeup I thanked him as he stepped out of the bathroom. I gave him a hug and nice kiss before grabbing my purse and heading for the door. Patrick asked if I wanted him to walk me to my car but I said I was ok. I opened the door and started my stroll back across the parking lot.
"Hey mama, I know you're not done for the night," said one of the guys from the balcony. "How bout you come up here and take care of all of us now?"
I just ignored them as I sauntered away from them, swaying my ass back and forth as I exaggerated each step. They all started whistling and yelling for me to come back. What a great ego boost!
I got to my car and started it and headed for the exit. Before I drove out though, I rolled down my window and waved to my admirers. One of them had pulled out a pretty good sized cock and was shaking it at me telling me that I was missing out on a great time. I'll be honest, I considered stopping for a second but knew I would not be safe with four strangers so I winked at him and kept on driving.
After getting home and soaking in the tub for a while I drifted off into a deep sleep, the best sleep I'd had in months. I had plans to meet another old playmate the next day and all I could think about was all the dick I was going to be getting over the next few days. After the first night I was glad I had jumped back into the dating pool and was looking forward to a few more days of fun.