First Meeting With Dom Sissy Mistress free porn video

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I was a longtime secret panty sissy who played in private and only dared dream of finally meeting someone face to face when I met Miss Jamie on xhamster. We had an immediate rapport online and before long she suggested meeting. Of course, with her long experience as a sissy, and with me being an obviously natural submissive, she would take the role of teaching me my proper place as a submissive sissy. This is the account of that first meeting.

Miss Jamie's logistics were simple:
I was to park at a nearby shopping center and wait for her.
When she arrived, I was to get in her car.
She would take me to the house and have her way with me.
When she was done with me, she would drop me back at the shopping center.

Her rules were equally sparse:
I was to arrive at the shopping center wearing panties under my street clothes along with any other feminine under items I possessed.
I was to arrive with my sissy hole plugged.
Sessions would begin when Miss Jamie picked me up and end when she dropped me off.
Limits and safe words were to be discussed thoroughly before and after sessions.
During a session, I was only to speak when told unless given permission.
During a session, I was to do everything asked of me with no exceptions.

That morning my emotions were a tumult. I was nervous, my thoughts were s**ttered, I was more than a little scared; but I was also very aroused! When Miss Jamie emailed me that our meeting was a go and to be at the shopping center by 12 o'clock, my heart was pounding, and all the more sitting on my plug in the parking lot with the minutes ticking down to noon and finally seeing her car pull up next to mine.

Miss Jamie just watched me for a few seconds after I got into her car. Then she caressed my cheek and said, "Hey, baby." I think I was blushing. She put her hand on the inside of my thigh and slid up to my crotch. I spread my knees submitting to her touch. She felt my erection and smiled. She took my hand and placed it on her crotch. "I'm excited too, baby," she said. I thought about her many lewd emails and knew that her sissy cock would be in my mouth before long.

She reached down between her feet and picked up a bag. "I brought you a present," she said and pulled out a realistic, and quite large, black dildo. "Put this in your mouth and don't stop sucking on it until I tell you to stop." She watched me for a minute then started the car and pulled out of the parking lot. It was not far to the house, but far enough that we passed two or three cars on the way. She watched me blushing as the cars passed and asked if I thought she should honk to draw their attention. Later Miss Jamie would explain that it is common for sissies to enjoy humiliation to varying degrees. It was one of the things she noticed about me in our online exchanges and she knew it would embarrass me terribly, but excite me even more. And in fact, though I was relieved that the garage was behind the house and that there was a privacy fence, I was now very, very aroused! I felt like a slut and wondered if any of the other drivers had actually noticed what a slut I was. More than that, I hoped they had.

Inside, Miss Jamie showed me to a hall bathroom and instructed me to strip my male clothes and then wait for her, kneeling in the hall, facing the master suite, wearing only panties and thigh highs with the rubber penis still in my mouth. I did as I was told, thinking of how different it was to be sucking a latex dick in front of someone instead of in private. Then thinking about what it would be like with a flesh penis in my mouth. And then I was watching her walking toward me in a zebra striped dress.

She stood in front of me, her crotch at my eye level, lifted her dress, took the dildo from my mouth and said, "Kiss my clitty." Her sissy cock was visible through sheer white panties and the smell of her filled my senses as I obeyed. She pulled her panties to the side and I took her into my mouth. Her clitty cock continued to harden until it filled my mouth. She caressed my hair as I sucked her and after a minute or two, pulled me into her forcing me to take her balls deep. Miss Jamie received my attention for a few more minutes and then stood me up, pulled my panties to the side and led me by my erect sissy clitty to the bedroom.

In the bedroom, Miss Jamie shared her deep experience as a sissy dedicated to pleasing men. As she lectured, illustrating with many personal stories, she used me physically.

It began with her laying back on the bed and me face down below her so I could look into her eyes and suck her while she taught. She explained that it sharpened a sissy’s concentration to have a dick in her mouth. She talked about how to please a man and had me practice on her sissy dick. She had me spend time licking her balls and then sucking them, and then taking both of them in my mouth. I had read about sucking balls and had tried it on a dildo but molded balls don't roll around in your mouth and rubber doesn't have that soft texture of the skin of a real scrotum. It was a new and exciting experience but not the only one.

Miss Jamie raised her knees to expose her beautiful sissy hole and ordered me to tongue her. She explained how many men liked to humiliate a sissy by making them rim them during a blow job and told me stories of her first experience of a man making her lick his ass hole. I had tasted my own ass on my fingers and dildos during play at home, but this was an entirely different thing. Again, I felt the humiliation and as Miss Jamie had suspected, the excitement. And so I pushed my tongue into her hole as far as I could and thrilled at the texture and taste of her. Miss Jamie observed that I was very much a natural submissive sissy and how readily I accepted her instructions.

Miss Jamie had seen from my online profile that I was a spanko. And she told me this was also a useful trait in a sissy since dominant men often like to spank their sissies. She bent me over an exercise bench and cuffed my wrists to the legs. In this helpless position, I felt her lower my panties and begin to play with my plug. Soon, she removed the plug and worked my hole with a variety of fingertip toys. I was startled when she slapped my ass with her open hand. She spanked me methodically, rubbing my cheeks hard. She switched to a hairbrush and the sting was multiplied. I was moaning and panting in arousal. she released me from the bench and took me over her knee turning my bottom into a red hot flame with hairbrush and belt.

All the while, as she moved from action to action, she continued to instruct me in how to live as a sissy ending with me on my back and Miss Jamie straddling my chest, holding my hair and fucking my sissy mouth; repeatedly driving her erect clitty balls deep down my throat.

When it was over, she held me cuddled with my head on her shoulder, caressing my hair and cheek. I was a thoroughly satisfied sissy!

Shelley

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A true story (from a blog written that day) about my first time both with more than one person and with a woman. It would have gone further with her but she happened to get her period that morning.This was actually written just after it happened a year ago. Sadly, I haven't seen them since as our schedules never seemed to match up after and I think they finally just gave up on me. A shame because they were a lot of fun.~*~So today I met up with a wonderful Dom couple.He is not at all a bad...

1 year ago
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First Night Out as a Sissy Pt 2 By Crystaled

So picking up where I had left off from my last published story…. I had just ventured out for the first time as sissy, determined to find a man. I went to a local sports bar dressed in in my tightest jeans and favorite panties and teased a group of guys. Was able to get one of them into my car for my first blow job ever and after swallowing his enormous load, his friends busted us before I could know the pleasure of him inside of me. After being busted (but feeling sweetly naughty) I was going...

1 year ago
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Ramona und das Dom Greenhorn

Ich bin glücklich verheiratet und liebe meine Frau, aber der Sex ist, naja… Ich akzeptiere das, andere Dinge mit und an ihr sind mir wichtiger als der Sex.Es gab aber eine Zeit und eine Frau, mit welcher ich den perfekten Sex hatte. Obwohl es schon eine gefühlte Ewigkeit her ist, beschäftigten mich diese Erlebnisse noch immer. Es ist auch nicht erfunden, sondern hat sich genau so abgespielt – zumindest so, wie ich es in Erinnerung behielt. Ich habe so etwas noch nie gemacht, aber ich habe das...

1 year ago
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My Dom and Her Mom

I had been asking my wife Carol if we could get into a bit of bondage, something I read about somewhere and it seemed that having ones wife as a dominatrix could be a hot idea. Her mom is a damn good looking woman, had I not met her daughter, I could be very content with her. Agnes must be like sixty five and plump. Nice ass and hips;long grey hair and plenty of bosom What I really liked about Agnes though is that I can talk to her about anything. She has a great personality. What I did not...

1 year ago
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Brandy with four Doms and two Dogs

I have several Doms I see often and even now two Femdoms that I visit infrequently. But I like variety and my sexual appetite is almost insatiable so I need to see different people for different experiences. I am upfront with them and my Doms all know about the others. Everything in my life was fine until one of my Doms contracted COVID-19, so I had to quarantine for 10 days and get tested regularly; well guess what even though I...

3 years ago
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Dom In Denial a fantasy about dominating and pre

We've been messaging each other for months, finding out more about the other, seeing what made us tick... what made us hard. We've finally met, in the bar of a hotel midway between the towns we both live in. We introduce ourselves to each other, aware of the strange feeling of meeting what is essentially a stranger that we already know. There will be another introduction later, of course - that's why we're here. That's why both of us are shaking, ever so slightly. The tension is delicious.We...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
1 year ago
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First Sissy Experience

I accepted a new job in an executive role at a company in Kansas City and obviously with the new job came a new home and new neighbors. My wife and I were really excited to move into a very nice upscale neighborhood, we looked forward to getting "plugged into" our new community as well as get to know our new neighbors. What I could never had imagined is what "plugged into" would mean for me.We moved into our new home the first week of September and were warmly welcomed by the neighborhood with...

3 years ago
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Sissy gurl meets Daddy

The doorbell rang, and Samantha's heart fluttered. She raced down the stairs and opened the door. She answered the door and managed to open her lipstick lips and say "hello sir". She stood in front of him with her Plaid skirt and white blouse, thigh highs with red bows, red mary janes and otherwise dolled up. Her hair in pigtails, he enters and follows Samantha up the stairs.he sat right down in the leather chair, asking for Sissy to pose. Samantha did exactly that, prancing around in front of...

3 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Reese Witherspoon dommed

any of the actresses mentioned below. This story is written down for enjoyment purposes only. Reese witherspoon woke up with a headache. She didn't know where she was. All she could feel that she was blindfolded. Not only that, she was tied to the bed with duct tape, unable to move her hands and legs. She also noticed that she was nude. A duct tape covered her mouth so that she shouldn't shout. All she remembered was going to a producer's home for some script reading of a film they were...

3 years ago
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A Sissy Fantasy A Day And Night With Daddy

A Sissy Fantasy - A Day And Night With Daddy Daddy's Cocksucking Princess I awoke after falling asleep after last night's escapades, and the first thing I I notice is the chastitiy, it immediately reminds me of what happened last night. I wasnt expecting to be put in chasitity last night, Daddy had hinted at it, but I did not think he was have me in it so soon. I did not really want to have my clitty locked up like that, but I really want to please Daddy, so of...

1 year ago
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Sissy gurl meets Daddy Part 2

It was finally later that night when Samantha had a moment alone to open the envelope Daddy had left behind for her after their playtime earlier that day. She unfolded the note and begin reading by her computer. The note read…..Dear Sissy, You are probably reading this tonight, because you can’t stop thinking about serving your new Daddy. If this is true, than my plan is working exactly like I thought it would. I’m going to ask that on Friday morning you take a shower and get as smooth as...

2 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

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