Tranny In Toronto

Tranny In Toronto

Craigslist Ad:

Married Couple Looking For Fun Time - mw4t - 40's (Toronto)

We are a married couple, looking for a bisexual trans for some fun. We host. Message if interested with times you're free.
To: [email protected]
From: [email protected]
Subject: Re: Married Couple Looking For Fun Time - mw4t - 40's (Toronto)

Hi, my name's Lizzie Elliott. I'm 18 years old, a m2f trans looking for fun. I'm safe and clean. Free every night except for Sundays. Can travel all around Toronto.
To: [email protected]

Hi Liz, can you come this Friday night at house... 9pm. My husband is really excited to meet you. We can discuss payments at our house. Can't wait to see you, don't let us down. If you cancel, here's our number...

I drove my car to Gerrard Street and Woodfield Road, then I searched for their small house. Once I found it, I parked my car outside the home and waited a couple of minutes putting on my make-up and perfume. Once I was ready, I left my car and approached their front door. It was a small two floor home, white in colour, and a old vintage-like red Honda car parked in their driveway. It was almost 9:00pm when I first rang their front door bell. It was a wonderful cool night tonight, no wind, no heat, just plain air all around you.

I was about to ring their doorbell for the second time when I heard footsteps approaching louder and louder from inside the home. It stopped really loudly, and then their door opened. And a woman appeared from behind the front door.

"Hi, you must be Lizzie, my name's Maureen. Come on in." Maureen said. She looked like she was in her 50's. Her hair was really short and grayish. She had some wrinkles around her eyes but she looked pretty good for her age. Her blue eyes were still bright however and her skin was pale. She was skinny, kind of cute, and she had this wonderful smile at me as I entered their home. She was wearing a black and red long sleeved shirt and black skirt, like she just returned from work.

She walked into the living room, with me following right behind. Their home was pretty small and clean, not many items in the home and really quiet. I entered the living room where she told me to sit down on her couch and asked if I needed anything.

"No thanks." I said to her as she sat down beside me on the couch.

"So Paul's waiting in our bedroom, I thought maybe we could do our transaction here."

"Okay then," I said as I opened my purse.

Maureen opened her purse as well which was on her living room cabinet beside the sofa. "How much do you charge?" She asked.

I thought about how much I should charge contributing the factors. We were gonna have sex in their home, I drove my car here, minimum wage is $10.50 but these people are elderly so they must have lots of money. This was their first time with a transgender, and the husband wanted me really badly. Hmm...

"$150.00 per hour." I said to her hoping she'd take my offer.

She smiled and took out some bills of money from her purse. She and I both counted $300.00, then she handed it to me.

I smiled at her as I put the money in my wallet and followed her upstairs into their bedroom.


Once I was in their bedroom, I saw an elderly man watching t.v while sitting on their bed. He was overweight, fat, big boned, whatever you wanted to call it. He had a big stomach, blue eyes, and a bald circled face. He was only wearing his shorts. His jaw dropped when he looked away from the t.v and saw me.

"Holy fuck, you're beautiful." He said to me. He got up from his bed and walked towards me.

"My name's Mike," he said as he took out his hand for a handshake.

"I'm Lizzie, call me Liz." I said to him while shaking his hand. He was staring at my breasts. He then put his hands out stroking my long blonde hair and then he leaned his face over and kissed me. I kissed him back and we shared a passionate french kiss before he backed off.

"You're such a wonderful kisser." He said.

"Thanks, why don't you undress me now." I said to him. I turned around but Maureen wasn't there, she must have left.

Mike began to undress me, removing my shirt, bra, and my small skirt. He began to suck my nipples which got me excited. We both moaned as he bit my nipple and then moved on to my other breast to do the same thing. His mouth was trying to suck everything from my breasts, and it felt so good. My nipples were hard when he pulled his face away and started to take off my panties. My penis was unleashed, 6 inches uncircumcised sprang out. Mike smiled when he saw it.

Mike pulled down his shorts as well, revealing his 4 inch circumcised cock. He then laid down, on his back, on his bed and motioned for me to come over.

"Let's fucking do some 69 Babe." He said to me.

I went onto his bed, climbed over him, turned my body around and motioned so that my cock was on his face and his cock was on my face. Then we both sucked each-others dicks dry. Using tongue, saliva, and teeth, we vigorously sucked each-others cock. I was scared of having my first cock in my mouth, but it didn't taste like anything. As we sucked, We moaned during this time as the pleasure filled our bodies. I felt myself about to cum in his mouth as he vigorously suck the contents of my dick. He was squeezing and slapping my ass every few times, the once pain was now pleasure and I loved it. Then he began to gently massage my testicles and fingering my asshole.

I felt his dick start to twitch as if he was about to shoot in my mouth. He stopped sucking my dick. "Stop." He said. "I don't wanna cum yet, I won't be able to get hard again. Here lemme fuck you."

I stopped sucking his cock which was still 4 inches hard and fat. I then got into doggy style position and he got up and started kneeling behind me. He then put his hands on my ass and started pulling them apart exposing my asshole to him.

"Look at that Man-Pussy." He said. He then leaned his face forward and began to kiss my ass. He made his way towards my asshole and started to lick it really gently with his tongue. The feeling was exotic. It felt so tender and sweet, I groaned as the feelings of my asshole licked spread throughout my body. He began to kiss it next overwhelming me with pleasure.

"That feels so good," I said to Mike.

He stopped and now he knelled behind me comfortably in a doggy style position. "You ready for a nice fucking babe?" He asked. He held his cock, he reached out, grabbed a condom, and put it on his erect cock; then started to slowly insert it into my asshole. At first, I didn't think it would go in but his saliva and the lubrication from condom helped and he found a way to push it in. My nipples became hard, my body filled with pleasure, and my dick became erect again as he pushed his small cock all the way inside my ass. He then slowly began fucking my ass, holding my hips and ass cheeks to motion me towards his awaiting dick and to keep my ass spread. Groans, moans, and sweat escaped our bodies as the pleasure took us all in. I could feel my erect cock's pre-cum cumming out.

After a minute of getting fucked, I felt Mikes cock start to twitch.

"Holy Fuck, it's so tight. Holy CUMMING!" He groaned as he shot load after load of his spunk into his condom inside of my asshole. I could feel my asshole squeezing every last drop of spunk into the condom. When his cock began to soften up, he pulled out, took off his condom, and laid back on his bed staring at me. I grabbed the condom he took off from the bed, and held it open on top of my mouth. His sperm was coming out of the condom right into my mouth. The smell wasn't as delightful but I held my breath and licked the condom free of cum. I swallowed each drop.

Mike closed his eyes and smiled. "FUCK, That was fucking amazing." He said aloud. He started to snore; falling asleep after his best fuck.

I grabbed my clothes from the floor and left his bedroom.


As I went downstairs, I saw Maureen sitting on her couch. She looked at me as I walked in naked and smiled at me.

"What happened?" She asked me.

"He's done, I think he's going to sleep." I said to him.

"Yeah, he's gonna get some very valuable sleep after today." She said smiling.

I looked at my watch. There was still 1 and a half hours that they had paid for left.

"You got an extra bed anywhere?" I asked Maureen.

"Yes, upstairs and to the left... why are you asking?" She asked puzzled.

"Come," I grabbed her hand and led her to the empty bedroom. As we got there, I realized it was empty, just a bed, cabinet, some junk.

Maureen looked at my nude body. I smiled at her and leaned my face over to hers. And I kissed her lips. When she kissed me back, I gently held her body and laid her on the bed, still kissing her in the process. I squeezed her breasts which got her moaning and my heart racing. We continued to make out until I pulled out and started to remove her clothes. I took off her shirt and skirt. She wasn't wearing any panties which was so hot. Her breasts were really small, much smaller than mine and saggier. But her pussy looked so amazing. She was clean shaven like me, but her pussy had lips sticking out. I laid her back into the bed which got us laughing as I always kept taking her down. I went in between her legs and began sucking her pussy.

Her pussy was really sticky but it felt amazing to suck my first pussy. I started with licking it, then kissing, and finally ended with fingering her pussy. She moaned louder and louder as I finger fucked her deeper and deeper adding more and more fingers until my 4 fingers with the exception of my thumb was deep inside her womanhood . My penis was erect, ready to give my virginity away. I leaned over Maureen's body, french kissing her as much as possible. Then I went in between Maureen's legs and spread her pussy. She was moaning still as I pushed my dick into her wet and awaiting cunt.

Her body began to tremble as I slowly pushed my dick into her cunt. It was so tight, wet, and hot in there. Maureen's eyes were closed as I entered her completely; my thighs hit her thighs. We both let out a moan. I slowly started to push my penis in and out of Maureen's pussy. She was moaning louder and louder the longer I fucked her. I sped up my face going faster and faster into her awaiting cunt. Her pussy was milking me. I continued to fuck Maureen rapidly; her body was shaking and her moans were getting louder. Her legs locked around my ass as the penetration I gave her was rapid. I sucked her breasts hard and kissed her during this as well.

"OH FUCK OH MY GOD!" she said as I felt her pussy open wide, I felt her body contacting, and I felt her juices explode from her pussy right onto my dick. That was so much for me as well. I felt my semen release from my balls, gather sperm, and spurt the marvelous cum right into Maureen's pussy. Load after load was milked by her pussy.

I pulled my penis out of Maureen's pussy and I laid on the bed with her. Her body was shaking, all over. I got scared.

"Are you okay?" I asked her scared.

"That was my first orgasm, ever. Holy shit!" She said.


I picked up my clothes, put them on, and left their home. My first fuck. And it was fucking amazing. I had gotten my first anal, my first pussy, both my virginity were taken by this couple. The best part was that I got paid.

If you liked my story, please like. Feedback is helpful. All stories are real, some things were edited to hide the identity and boring stuff was hidden as well.

Want a chapter 2?

Similar stories

Saving Daisy

John was a thirty something business owner; general construction, married young and divorced within a couple of years. He was now a happy bachelor and doing okay for himself knocking down a cool 6 figures, living in one of his spec homes and doing what he had always wanted. He didn’t go out that much because all it meant to him was another hassle like before and he had enough hassles to last him a lifetime. He had gotten quite a reputation around town for being a darn good builder and it was well disserved. He had always had this knack...


Likes 0

The Forgotten Heroes Chapter 3 "Fate is Crule."

You and Eve head off in the forest escaping the Knights of the Fifth Dragon. To kill the silence you ask Eve somethings about her. So how did you end up in the North Island? Eve grabbed her arms and got a look of deep thought on her face. I was young only 23 still a child by Elf standers but my tribe was murdered and nearly wiped out by a band of human settlers. I was spared because of my natural beauty and sold into slavery years later I ended up in the middle grounds where a wealthy Orintash tribes...


Likes 0

When Casting No Shadow

When a man who casts no shadow is of this world and Ethereal. Beware the fated love he brings for it’s your soul he comes to steal No one shall walk before him nor in his footsteps tread . For he dwells amongst the living,……… as well as the dead . - Michael Fletcher The Prologue . Torbridge , Devon . 1973 . When Elaine Hamilton finds a new born baby dumped on the church doorstep three days after the funeral of her father, Reverend David Hamilton, she saw it as a sign from God. Wrapped in just a thin blanket...


Likes 0

The Devil's Pact Side-Story: Alison and Desiree Get Married

The Devil's Pact by mypenname3000 edited by Master Ken Copyright 2014 The Devil's Pact Side Story: Alison and Desiree Get Married Note: This takes place in-between Chapters 32 and 33. Friday, July 12th, 2013 – Alison Hertz – The Wedding The day of my wedding to my Latin beauty, Desiree, had finally arrived. After today, I would be Alison de la Fuente. After getting her marriage to Brandon annulled, Desiree went back to her maiden name. It was a far prettier name then Fitzsimmons. Desiree and I spent several nights talking in bed about our new last name. Should one of...


Likes 0

A Night Out - Part 4

Part 4 We head out of the club and back up the alley to the main road. I hail a passing black cab and we climb into the seat. I give the name of a road you are unfamiliar with to the driver and we set off. You give me a questioning look, but I just smile in return, my hand rests on your knee, then slides softly up and down your thigh, each stroke venturing a little higher. You decide to lean back in your seat and enjoy the ride. The mixture of the wine you have had and the...


Likes 0

Queen Yavara: Chapter 8

Chapter Eight YAVARA I had seen Elena naked hundreds of times. During our early teens I’d been horribly envious of her woman’s form, and I often admired it. I remember how she used to blush when she caught me staring, but she never attempted to hide herself. I knew why then, but I never said anything. Homosexuality was disgraced in Highland society, and I feared for her sake. Truth be told, I feared a little for my sake, for even at the age of thirteen, I’d felt an odd tingling when I gazed upon the perfection the was Elena Straltaira. Now...


Likes 0

Summertime seduction part 1

Summertime seduction Pt 1 It was the summer of 1986 & I had just finished my O’levels at the English international college in Marbella, Spain. My family had moved there 2 years earlier. Most people at the school were friends & knew each other regardless of what age or class they were in, so obviously I was friendly with my younger sisters friends most of which were 14 & craved the attention of the older boys. The school holidays had just begun & my sister’s friend Alesha was having a pool party at her place to which I was invited, it...


Likes 0

Brandi and Jessica Halloween final

Brandi is my escort, i pay her to have sex with me. There is much more to it than that though, she is like my girlfriend. Since i started using her she has limited herself to one other client, she use to see about five. Honestly i might marry her and save her from that life. We do so much more than just have sex. I take her on dates, to movies, vacations, she stays over and so much more. She is one of the most gorgeous women that i have ever seen. She isn't too tall, about 5'6. Her eyes...


Likes 0

Tanya's horse fantasy

My girlfriend and I are seriously into some taboo fantasies! Fantasies that sadly at the minute remain that way but soon to become reality! I'm 29, she is 26! She's a size 6-8 and absolutely stunning! The day I met her I seriously fell on my feet! For several years I'd fantasised about girls with animals but never thought I'd meet someone who felt the same! When I first met we both tested the water as you do and it took nearly 8 months to actually get on to the subject of animal porn! She didn't want to admit it immediately...


Likes 0

The Medallion - Chapter 7

Monday Evening - Part 1 Jack Winters sat in his car outside of his sister's house. She wasn't home from work yet, but he knew Emily and the other two girls were already there. He pulled the medallion from beneath his shirt and gave it a good hard look, thinking about what David had told him earlier. I don't know if you're really changing me, but if you are, I need you to not mess with my head tonight, he said to the jade stone. With a sigh, he opened the door and headed toward the house. Emily answered the door...


Likes 0

Popular searches


Report this video here.