[TM] Dicked down in the Big Apple (FTM)

*Skip to ***** to skip the trans 101 and the backstory*

Just to recap what I’ve said in my previous post: I’m a passable female to male trans guy who lives completely stealth. Which basically means that I’m a man and nobody knows that I have a vagina.
Because I live stealth in my home city, its harder for me to find people to hook up with and for that reason, I like to take advantage of the times I travel and am surrounded by people I don’t know to go a little wild…

This summer I decided to take a trip to New York City on my own. I took my two weeks off and rented a cute AirBnB in Brooklyn. And once I was settled in I did what I would never do in my home city: I went on Grindr and uploaded a picture of my topless self with the tagline ‘FTM’ followed by a downwards arrow emoji. I then went for a walk in the neighbourhood, leaving my profile on to see if I could meet somebody interesting on the way.
A dozen faceless dickpics later I receive the first respectful message yet. A black guy in his mid twenties with a ripped body covered in tattoos asking if he can smoke me up. He also tells me that he would love to fuck the shit out of me but he wants me to know that he’s cool if it doesn’t happen. So I say yes. And a short walk later, I’m waiting for him outside his building.

[MF] Met at a nude beach

So a little about myself. I’m 30, a little on the heavier side, but I wear it well, with enough muscle mass to offset my more chubbier side. In the summer, I often go to the local nude beach, not to be creepy or anything, but because I like how freeing it is and I find it relaxing.

Every time I go, I go to a meetup website for the beach and see if anyone is looking for company to hang out with, since I don’t have any like minded friends that want to go to nude beaches. That day I was in luck. I’ll say her name was Lucy and she was a married woman looking for nudist friends to hang out with. I sent a message, then headed to the beach.

When I got there, I kept on my shorts walking around as I looked for her where she said she’d be and her colored towel. When I found her I introduced myself. She wasn’t skinny or anything, but nowhere near fat. A cute kind of chubby that I kind of gravitate towards. She was just wearing bikini bottoms, her boobs already free. Her nipples were like erasers, almost naturally sticking straight out, but her boobs were just a handful, the perfect size, in my opinion. But that wasn’t why I met up with her. After all, she was married, and I was fine just having other nudist friends.

[F]ucking my sisters college roo[M]mate on Halloween

My sister is 2 years older than me and we went to the same college. My freshman year she went to her bf’s college (out of town) for halloween and her roommate, let’s call her Kelly, invited me to come to the party she was going to. Of course, as a freshman without a fake ID, I said sure as I had met Kelly plenty before since she lived with my sister for 2 years.

Kelly was not hard to look at. She was short, maybe 5’1, long straight black hair, full C cup and worked out regularly. I dressed up as a pirate in my dorm and walked to her place to start drinking before the party. When I arrived I saw her in a fairy/princess costume with a tiara, tight pink crop top, a short white skirt and pink fishnet leggings leading to her white high heels, she looked great. My sisters friends were there, maybe 15 of them drinking and when the time came we all headed down to the party.

[F]ucked by my Sir [M] and punished.

She wanted Sir so bad. She yearns for his huge cock. Thinking about it makes her want to touch herself. She strains to keep from it.
Her task was to wear the plug for a full day. The longest she’d ever worn it. She’s gotten use to it. But it still leaves a full feeling. And with every step she takes, her pussy gets wetter and wetter. Making her daily tasks intense.
She awaits the next message, hoping for some release.
“Bzzzz”
There it is.
Her phone reads, “Sir”.
She looks at the message.
“Meet me, Now. 15 minutes.”
She quickly grabbed her things, as she knew not to be late for him. Ever.
She gets to their spot and sees he is already there. She enters the building and he guides her upstairs. Taking her into “The Room”.
She enters and takes her place on her knees awaiting her next order.
She’s learned her place. He enjoys his control over her. Knowing she is his to do whatever he wants with.
He walks over to his little cum slut, and tells her she is lucky because she gets to please Sir today.
She looks up at him and asks him for permission to undo his pants. He nods, and she proceeds. She undoes the belt and gets to the button, then zipper.
She smiled a little because this is her favorite thing to do.
She pulls out Sirs big cock, and fills her mouth. She starts to suck and stroke him..licking his thick head and running her tongue around the shaft.
She loves the taste of Sirs cock. She can’t help but get a little out of hand.
She didn’t listen to Sirs signs and he pushes her away.
She’s never, to try to get him off. Sir tells her when he is going to get off.
Embarrassed she sits back on her feet. He tells her to get on the bed.
She does as told, and gets into position.
She gets on her knees and pushes her face into the bed. Stretching her arms down, she puts her hands to her ankles and he ties them in place. Sir admires the jewel he’s had her wear all day.
He rubs her ass and goes to the jewel, twisting and turning it. Watching the cum seep out of her pussy. He knew this was torture for her. Not being allowed to cum.
He continues.
She lies there and tries hard not to let him know she’s about to cum.
Sir knows her body though, and feels her starting to shake. He slaps her ass and tells her she better not cum.
Taken by surprise, she jolts and tenses up.
He starts to play with her pussy, watching her juices drip down her legs.
Quickly he shoves two fingers in. Knowing she can only handle one at a time. Causing her to let out a moaning squeal.
While playing with her he twists the jewel and notices how tight it makes her get when she tenses. So without warning, he thrusts deep and hard inside her. With the jewel still in her ass.
Taken by surprise, she gasps.
Sir enjoys the expression on her face. Knowing he controls how she feels. Not her.
Thrusting harder and deeper she tries not to cum, but before she could control herself she lets out a loud moan and starts to tense and shake. He stops, and grabs her by her hair pulling her towards him.
She knew she was in trouble. She’s not to cum until permitted to.
Sir asks her if she came, and she knew not to lie. Shaking her head yes, he slaps her face.
She will pay for that. She knows.
He began thrusting harder and harder, smacking her ass and telling her she will regret that she disobeyed him.
Deeper he pounded her tight pussy. Not listening to her screams as he went too deep.
He pushes her forward and starts playing with the jewel, pushing and pulling it. Twisting it and teasing her ass.
Telling her she will pay.
Disobedience is not tolerated and he will have structure and order.
Without warning, he pulls hard making her tiny asshole pop when he pulls out the jewel.
She held herself, and showed no fear. His little slut still wasn’t use to the ass play.
He starts to take her own juices and rubs it around her asshole.
She tenses a bit and he pushes his thumbs in. Telling her she’s going to be full in a few minutes.
She feels her eyes start to water. Quickly she rubs them on the bed to keep him from seeing them.
Before she had time to open her eyes she feels a sharp quick burst of pain as he pushes deep and hard in her ass.
She tries to shift to welcome him but he just keeps going. Harder and faster, he hears her cries and moans. Feeling her pussy dripping with cum, he reaches under and starts to rub her clit. Knowing she cannot resist the urge to cum.
He is testing her. Torturing her with every flick. Knowing his restrictions on her. Deeper he goes, and faster he pumps. She feels him about to bust and he pumps faster and harder.
Before she knew it she feels her ass start to fill up with his hot cum. The full feeling she has is intense.
His hard cock throbs and pumps every drop of cum into her tight ass.
Sir pushes her off him and she feels his load oozing out of her ass and down her leg.
She lies there expecting him to untie her so she can clean herself. But he doesn’t, she hears him leave the room.
After what felt like and eternity, she hears him enter the room. But he wasn’t alone. There is another set of footsteps. She starts to shift and tense up. She’s nervous. She feels a hand run from her lower back down to her neck. To hold her still. This is not Sir. There was a different feel from the hand. Before she knew it she felt another hard deep thrust inside her ass. The pain starts again. But it’s short, and fades. He’s not as large as Sir so, she can welcome him easier.
Harder and deeper he thrusts. Pushing her down into the bed making her arch her back, keeping her ass tilted and her lower back angled perfectly to thrust deeply inside her.
With his other hand he grabs her hair and pulls her head up. Revealing Sir in front of her. And his hard cock at face level. Sir shoves his cock inside her mouth making her deep throat every inch.
She focuses on Sirs cock, sucking and licking cleaning her mess off him.
They pushed in synchronization. When Sir pushes, his friend pushes. She notices his friend getting faster and harder. Before she can think, she feels her ass get filled with his hot load. But before she can focus too much on him, Sir pulls her head into his pelvis and starts to force fuck her face. She opens her throat. To better comfort Sir. And without notice he pushes his cock deep inside her throat and busts his load. She starts to gag but corrects herself. She is not to leave a mess.
His friend already gone, Sir leans down face level and tells her to never fucking cum without permission again. He pushes her face down and unties her hands and ankles.
Then tells her to clean herself up and leave. She is to await his next orders.

Sexy coworker w/ a bf cheated and [F]ucked [M]e after-hours

I apologize that this is a long story but there is a LOT of background and history. I promise it’s worth reading in full.

This happened my sophomore year in college. I worked at a fancy restaurant for about 4-5 months before this girl, we will call her Abbi, was hired. She worked part time as a yoga instructor and at night made extra cash at the restaurant while she was in school.

She was about 5’3, 110lbs with wavy blonde hair, blue eyes, perky B cups and a nice firm ass you would expect from a yoga teacher. She had a bf that she had been dating since high school but you know how working in a restaurant is, there’s always tons of flirting and joking around.

One night after work maybe 6-7 coworkers and I went across the street for a drink. Abbi was sitting next to me, still in her black dress as we drank and chatted. One by one people started leaving to go home as it was pretty late until it was just Abbi, me and one other coworker. Abbi was tipsy and pulled out her phone taking snapchats and what not when she looked at me and said, “why aren’t we snap friends?” I looked at her and said, “Idk if your bf would like that” half serious half joking. Then she added me on snap and watched as I accepted and gave me a little smirk. I didn’t think much of it at the time. We all got up and went to our separate houses/apartments.

I would do anything [f]or Sir.

Lately, I’ve had a lot to do at work. Most of the time I only see Sir when we sleep next to each other in bed. I have read a few stories on reddit lately, and I can see myself in so many of them.

The thing I like the most is to please my master, and to see him looking at me with a dirty look on his face. I like to dress up and look pretty and slutty at the same time and I love having red lipstick because I know that he only can think about fucking my mouth when I have it on. I can live from the look on his face when he sees the red lipstick for ages.

[MF] [FF] First Ever Foursome, Part 2

See my previous post if you need to catch up :)

After the nights fun so far I’d have been more than happy to have spent the night spooning with Ginny, Stan and Sarah but pretty much as soon as we got in bed we started fucking.

This parts a bit blurry because of the drinks but I’ll do my best.

I remember grabbing Ginny by the hips and pulling her to the edge of the bed so I could fuck her on her back with her legs up around my waist. I don’t remember a lot but I remember being surprised at just how wet and ready for me she was, she’d obviously been enjoying the night a lot so far.

Stan and Sarah had started fucking doggystyle on the opposite side of the bed facing us so Ginny could reach under to play with Sarah’s tits and I could grab her by her hair and pull her head up to make out with her, all whilst burying my cock in Ginny’s soaking pussy.

[M]y wi[f]es anal virginity.

“Get upstairs and get naked” my wife said to me.
I chuckled but I ran like a kid on Christmas, because I had a plan. My wife and I have lots of sex but we definitely get into a routine. Not that it’s ever bad but tonight it was time to shake it up.
I quickly stripped and grabbed a few items from our toy box. A pair of handcuffs, a blindfold, and a paddle. When she came upstairs I was laying naked in bed cuffed and blindfolded with the paddle resting on my chest. I heard her giggle and gently pick up the paddle.
“Tell me if it’s to much.” Se said.
“I will,” I replied and almost instantly felt the paddle lightly smack my balls. I jumped and moaned, she knows what I love. She began paddling harder all over my body smakcking my nipples thighs and feet always working her way back to my balls. Pretty soon I was rock hard and I could tell she wanted to ride me.
I felt her climb on top of me and then move up so she was pinning my cuffed hands to the bed. And the she pushed her pussy right to my mouth. I began licking her clit eagerly and she began to grind against my face. I could her her moaning and feel her cunt getting wetter and wetter. Soon she began to shake as she cried out in orgasm.
She climbed down from my face and said, “ you are going to be doing a lot of that tonight but right now I want you cock.”
She straddled my waist and guided my cock up to her dripping pussy. Then she slowly slid down my 7.5 inch shaft and began to ride me. She was grinding her clit against me and I began to feel her wetness dripping down my balls. She was definitely getting all worked up over this. Soon she was cumming again, her body tending and her legs quivering until she finally collapsed on top of me.
I felt her rip the blindfold off of me and then she undid the cuffs and rolled over. As I climbed over to be on top she pulled me down and said,” I have a surprise for you, if you eat me as long as I want, and then fuck me hard I will let you do what ever you want.”
“Careful,” I said, “That might be dangerous.”
“I know ,” she replied “so get going before I back out of this.”
Was this really happening I wondered as she shoved my head between her legs and smashed her pussy into my face so I could start licking her clit again. I had wanted to fuck her ass forever and she knew but she had always been pretty opposed to the idea. Now I noticed she was even moving her ass up in the air so that occasionally my tongue brushed her ass. She climaxed four times before she let me back up.
I began to move my cock back to her slit and she said,”now remember fuck me hard.” I grabbed her legs and put them over my shoulders and then pushed my throbbing shaft inside of her, then I fucked her hard and deep. My balls slapping against her and hearing her scream had me close to the edge, but I held out. I wanted her ass so bad. It didn’t take to long and she began to cum, I kept fucking her not letting her rest and put her into one of the longest orgasms I’ve ever seen. When I finally ran out of breath she pushed me off and said, “get the lube, and my vibrator.”
I eagerly grabbed both and began to lube up my cock and made sure to get some on my fingers. When I got back to her she once again pushed my head down to her cunt, but this time as I began to lick she told me to try a couple fingers. The first finger went in easy and when I felt her relax I slipped another one into her ass, still focusing most of my attention on her clit. Soon she was cumming and I though I might just from knowing she was cumming with my fingers in her ass. When she caught her breath she looked at me and said “ok, I’m ready.”
I still couldn’t believe it but I got back on top and felt her grab my cock and guide it to her asshole. It took a couple of minutes but all of a sudden I felt the head pop into her ass, she stayed very relaxed and soon I was all the way in her butt. I began to thrust slowly and then when I pulled back I watched her sink her vibrator into her pussy. When I slid back in she pushed the vibrator base against me and turned it on so she could let go and have me do all the work. It was a lot of work to keep the vibrator moving but it was so incredibly hot watching my wife getting filled by a toy in her pussy and my cock in her tight asshole. Gradually I picked up the pace and we both began to moan in extasy. She pulled me tight and moaned in my ear, “I want to feel you cum in my ass.” This sent me over the edge and I began to cum while I pushed my cock as deep as I could into her ass. She changed the setting on her vibrator and I felt her begin to shake and she climaxed one last time.
When we both caught our breath, I gently pulled out and she put her vibrator down. We payed there kissing for a long time.
“That was fun” she said. “ I don’t think I could handle it every week but maybe we could keep doing that here and there.”
I laughed. “Honey, you don’t have to twist my arm, but it’s up to you.”

[MF] Gave a classmate head so he would write my paper

The other we had a pretty big party in one of the dorm rooms at school. I was in a crop top and leggings with wholes ripped out on the legs. My friends and I were having a good time like we normally do. About an hour into the party a kid who I don’t know personally but I recognized came up to me and said “hey Natalie, what’s up we’re in the same advanced writing class” I honestly didn’t know his name, he was a fairly tall and very skinny kid. Couldn’t be more than 150 pounds. I just responded to him how much I hated that class and how bad I was doing. We talked for a bit and I eventually found out his name was bill and that he was doing extremely well in the class. We had a huge paper that was due in a few days and I honestly hadn’t even started it. So I figured I might as well ask him if he would do it, he was blatantly checking me out undressing me with his eyes the whole conversation. He said he was busy with his own work, I was a little buzzed at the time and I boldly asked him if he would do it if I gave him head. He thought I was fucking with him at first but I asked again and he agreed.

[MF] Booty call from an older man.

It’s a weeknight, fall in Oregon, a little chilly but not so as you’d complain. I’m naked beneath the covers in the dark, alternating between emails and reddit. My phone vibrates in my hand, a text from a number I don’t recognize.

*Hi, it’s Jason. Okay for me to text you here?*

There are no Jasons in my personal life. The only one I can think of is a potential client that wound up being a dead end. I conjure up his last name, text it back as a question.

*Yes. Is it okay?*

*Of course. What’s up?*

*You were on my mind. How’s your night?*

Pleasant butterflies in my stomach. It was a good meeting we had. Nothing came of it, but he was certainly memorable. Probably twenty years my senior, he heads a project to create a green sector in the city, buildings that meet exacting environmental standards, appropriate retailers, bike access and parking, that kind of thing. He was handsome, a kind face with humor and stress lines, hair and beard cropped close and groomed, halfway grey and leaning into it. Fitted suit, no tie. The drive and passion practically radiated off him. His looks got my attention, sure, but it was the pitch that reeled me in. He was magnetic.