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Tranny in Toronto - Chapter 4 - Valentine's Day Threesome

2022-09-30 01:09:46

I wrote this story in an hour, let me know what you think about it. Have a happy Valentine's Day.

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Discreet Couple Look'n For Valentine's Day Fun - mw4t (DownTown T.O)

Wife and I want to fuck a lovely female tranny on Valentines Day. Must be bisexual, message me.


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Hello, I hope you're having a wonderful Friday night.

My name's Lizzie, I am a transgender woman who is also bisexual. I will be happy to meet up on Valentines day, for the right price. Please contact me at 647-241-****.

Have a great day.

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Today is Friday February 14th 2014. Valentine's Day. I saw an ad on Craigslist asking for a transgender woman for a threesome. Of course, I decided to give it a try for the right pay. I received a phone call from a man named David saying he and his wife, Janet, wanted to have a threesome in which all three of us can have fun on this "very special" day. They are both straight human beings, but have always been curious of having a threesome, especially with a "tranny." So after he gave me his address, I decided to give it a shot.

After discussing the price and details on the phone, I went to their home. It was a cool breezy night. 8:00pm. I drove to their apartment and parked my car in the visitor parking spot, it seemed like everyone in this area decided to stay home on this special day judging by all the cars around the apartment. I then went to the front of the building where I found myself not knowing how to get into the building because I didn't know the couple's last name to use the buzzer. All the outside doors were locked, so I decided to just stay at the front of the building, and waited for someone to open the door for me.

It was a dark building, well that's just from the outside. On the inside, it was very bright, full of lights but again, the main lobby door was locked. At least now I was inside the building instead of out in the cold. It wasn't as cold as the past few weeks, but still a chilly day, no snow. Fortunately, two men came in, gave me a quick glance, and opened the building door using their key and I walked in.

"I guess they live here," I thought as I went and pressed the elevator button. When I turned around, I saw the two men staring at me. I smiled and they smiled back, but I decided that I wasn't interested in them, so I just took out my cell and pretended to actually do something, like most girls do when in a tight situation. When the elevator door opened, I went inside, followed by the two men. I pressed the 4th floor button, while they pressed the 6th floor and 7th floor buttons. I got off at the 4th floor, and then had to decide which way Apartment 407 was.

I decided to try the left side first instead of my right; apparently I was right as I found it. I knocked on the blue wooden door.

A man opened the door, he was about 5'8, white, in his late 30's with some facial hair. He seemed to stare at me as he opened the door, maybe I'm at the wrong house?

"Hi, I'm Lizzie..." I said as he stared at me with his light blue eyes. He was really cute and seemed to examine me for a few seconds.

"Yeah I know, I'm David. Come on in," He said.

I walked into their apartment home, which appeared to be like a jail cell. Clothes on the living room floor, small t.v, not very bright lighting, dirty carpet, small couch. Basically it was a small home, I wonder where his wife is? I went into the small living room, and decided whether or not I should even sit down on these maybe cockroach infested couches, just an assumption of course. Did they even have enough money to pay me?

"Would you like something?" David asked while opening the fridge in their kitchen.

"No thanks, I'm good." I replied back.

"We have some cold beer." He continued.

"No, it's okay, I've drank before I came."

"You know, drunk driving is illegal, right." He said with a smile. I smiled back.

"Oh hey, you must be Lizzie." The woman said as she entered the living room, she must have been in the washroom when I was allowed in.

"Hi, you can call me Liz." I said as I shook her hand.

"Welcome to our home, I'm Janet and I guess you've already met David" she continued, "I know it's probably not as good as you'd expected but well, we like living here."

"Well, if you're happy living here, I'm happy for you. And it looks like a decent home." I lied. Sometimes one wrong thing you say could ruin everything.

Janet smiled, "So let's discuss the deal..."

~~~

To skip the boring details, we discussed the deal would be $200.00 for the night. The couple said they were okay with oral, but must wear a condom when having intercourse. I agreed as this is usually the deal I give to my customers.

I followed the couple into their bedroom. Even though they lived in a one bedroom apartment, it was pretty big. As well, it was clean, having a beautiful bed, everything sorted, and vacuumed. That is when I realized that they had probably made this place look better, just for me.

~~~

The couple both began to remove their clothing, all at once. I never expected that. But I followed their lead, turning around from their view and removing my sweater, my tank top, my bra, and then removing my jeans. I decided to keep my stockings on, but decided well, they do know I am a transgendered human being, right? So there I stood, nude. When I turned back around, I was amazed to see them both naked as well and staring at my naked body. They probably have never seen someone with breasts and a penis.


I walked over to their bed and jumped on, they both followed my lead this time by coming onto the bed. l leaned over, held Janet's face very gently and began to kiss her on the lips, very softly. Our hands began to explore each-others bodies as we kissed passionately, bringing in tongue to show her husband who was masturbating his penis while watching us and moaning a few feet from us on the bed.

She stopped kissing me, "I never thought you'd moan seeing me kiss someone else," She said while smiling at her husband on this beautiful day of Valentines. I smiled as well, then took Janet's breasts onto my hands and squeezed them which got her to giggle a bit. I licked her breasts very softly while using the most saliva as I could, savoring the taste of boobs. Her breasts were a little bit saggy, but looked very cute, and I gently bit into each one which got her to moan even louder.

I turned around to see David very close to me, coming closer to my body.He began to kiss slowly up and down my neck, my eyes began rolling into the back of my head from the pleasure he quickly gave. He moved up, kissing my cheek as he went along, before moving onto my lips which he gently caressed with his, slowly moving his tongue in and out of my mouth. I returned the favour and allowed my tongue to enter his mouth which gave me great pleasure. I can tell he was horny as well.

I broke our kiss and began to kiss his chest, moving downward while kissing and blowing on his body until I reached his limp penis. I was just about to start sucking his penis when his wife interrupted.

"Wait," She said. "Honey, lie down on the bed while Liz sucks you, that way I can suck hers as well."

He didn't look to happy with the idea but proceeded to listen. He lay down on his bed on his back, and I went onto my hands and knees in between his legs, and began to suck his penis. I leaned forward and started licking and sucking down the side of his shaft as I heard a soft moan. I slowly moved back towards the tip which I licked around in circles a few times before I couldn't wait any longer and finally put my lips over the head of his penis and began to suck his shaft down towards the back of my throat. I started off going about halfway before moving back to the tip while stroking the rest of his penis. I continued to bob my head up and down his uncut penis for another minute or two before I got the courage to start deep throating, gradually moving my mouth all the way down to the base of his penis so the top was touching the back of my throat and my mouth was touching his crotch.
I noticed his dick wasn't even that large, maybe four inches which helped me deep throat him.

His wife now lay down in between my legs, took my penis into her mouth, and began to suck it at the same time. The pleasure I was receiving and giving was incredible.

David began to moan loudly as I fought the gag reflex for a second or two. It calmed down and I stayed in that position for a good ten seconds before I gently drew back along the length of his shaft and allowed it to leave my mouth with a slight popping sound. I looked up at him with a cheeky grin on my face. "You like that?" I asked while stroking him off. A low groan was all he could reply with but it answered my question well enough. "I thought so".

My attention was then drawn to his balls, which were smooth and completely hairless. I leaned in towards them and, while continuing to stroke his manhood, took one of his balls into my mouth and set about rolling it back and forth over my tongue. I kept sucking on his ball for another minute before I let it slip out of my mouth. I could see by the look on his face that he was disappointed I'd stopped but he wouldn't be for long as I stopped stroking his now fully erect penis and instead pointed it towards my mouth and took the entire length in straight away this time.

I moved my mouth up and down his throbbing member, each time taking it in all the way to the back of my throat before withdrawing so far that only my lips and tip of my tongue were touching it. After a while, he gently put his hands on my head and began to slowly push downwards each time I was going down on him. I took this as a sign he was getting close and I increased the speed of my sucking to which he responded with louder moans. As I stepped up the speed further, his moans got even louder and more frequent. I could tell he was on the verge of an orgasm so I started sucking as fast as I could, deep throating each time.

"Okay, now I wanna fuck you babe." He said pulling my head away from his 4 inch erect cock which looked like it was about to blow.

Janet stopped sucking my cock, which was now stood 7 inches long, full of saliva. I went into the doggy style position as David and Janet got up and looked for something.

"Oh here they are." Janet said grabbing the bottle of lubrication and a pack of condoms. She ripped one condom out as well as handed her husband the bottle of lube.

"I want your cock inside me, NOW!" I yelled.

David quickly opened the bottle of lubrication and released some onto my asshole. The feeling of liquid flowing down my manhole felt so awesome. David then opened the packet of condom, took it out, and placed it onto his 4-incher. I helped him by spreading my ass-cheeks with my hands, he lined his cock up and slowly shoved his prick into my ass.

"Oh shit, that feels amazing." I moaned while he pushed his prick all the way inside. "Oh yeah, go faster."

David began to fasten his pace, fucking me doggy-style harder as well. He began moaning louder and louder as he fastened his pace.

"Your asshole is so fucking tight, fuck!" He kept on fucking me faster and faster as we both began moaning.

"YES, FUCK ME FASTER HARDER FUCK ME FUCK ME HARD!" I screamed as he grabbed my tits and squeezed them tightly. Her wife came right in front of my face, held it, and began to kiss me aggressively, like a crazy person on drugs. We were having the roughest Valentine's Day sex ever!

"I'm cumming, HOLY FUCK!" David screamed as he shoved his dick all the way into my asshole. I felt his dick begin to shake, felt his body tense and freeze, and within a couple of seconds, felt his penis erupt and shake all into my asshole. I felt myself filled with pleasure, while Janet continued to shove her tongue into my mouth and explore me.


David pulled his limp dick out of my asshole. Janet was still kissing me but I slowly moved away and turned around to David. I held his limp dick onto my hands, pulled the condom off of his cock, held the condom above my head, tilted my head up, and let his seeds flow out of the condom all into my mouth. David and Janet watched as I smiled, showed them David's white sperm in my mouth, and swallowed. The look on their faces was happiness, but also surprised I would do such a thing/

"Okay you must leave now." David said as he got off the bed.

"Wait, I want to have sex with Liz." Janet said. "What do you mean?"

"I don't want her fucking you, I've had my fun and I'm happy, that's what you wanted right?" David said to Janet, "Well, that's all. Thanks for the fun."

"What's so fucking wrong with you!" Janet screamed, "We were both supposed to have fun this night, but you fucking ruined it all."

David got off the bed and went to the washroom, slamming the door after he went in and turning the shower on. I began to put on my clothes and gathering my things.

"Here's your pay." Janet said as she handed me the cash for the night.

I smiled. "I'm sorry you didn't get to have any fun," I said.

"Hey, I had a lot of fun... Liz, um, let's say I phone you and maybe ask for us to meet up and you know, finish off. Would that we okay?" Janet whispered scared her husband might come out of the washroom and hear.

"Of course." I said as we kissed each-other a farewell on this wonderful Valentine's Day.

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Let me know if you want more. I don't read comments, so private message me please.
Happy Valentines Day.