First Night Out As A Sissy Pt 2 (By Crystal_ed) free porn video

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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 to call it a night before I realized the bar tender still had my card because I hadn’t closed my tab.

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So it was the perfect excuse to wander back inside and relish in the feelings I was having. I very much enjoyed the slutty feeling of having just been fingered and giving my first BJ all the way to completion. I was happy I always had the foresight to pack a small bag of necessities which also included some other girly clothes I wanted to be seen in. I freshened up and walked back into the place pretty light headed from either the few drinks I had or the sensation one gets when a fantasy comes true.

I returned to my place at the bar and was immediately attended to by the same female bartender. From earlier, it already seemed she was very familiar with the group of guys I was teasing and she had this incredible smile on her face like she knew what I had just done. I didn’t care; I almost wanted to kiss her to share the lingering taste of his cum just to see what she would do. I decided to pass but just as the fantasy was fading I felt the warmth and strength of someone’s hand slide firmly across my butt.

I turned with my eyes somewhat closed expecting to see “my guy” instead it was one of his friends and his girl. I could tell she didn’t seem to care for me but was playing along with something. This new guy asked, “hey, come back to our table, there’s always room for an ass like this” as he patted his hand on my butt. I loved being talked to like that as it made me feel so sexy and I could just feel the sissy personality I never let out overcome me. I accepted the invitation and was well received by the group. They all seemed pretty close and I imagined they had fun in many ways together.

“My guy” was not really acknowledging me and I didn’t feel too bad about it. I could tell he was getting a bit jealous and was trying to hide it. Since the place was more of a sports bar type hang out, the only source of music was a juke box just behind our table. Wanting to be seen by my group, I pretended to be interested in finding a song so my back was turned towards them. Just then, a sexy tune filled my ear and I began to move slowly, gracefully and as seductively as I could. I imagined one or all of them watching me move and I hoped they were imagining what it would be like to have me.

The gal that had come over with the new guy to invite me to their table came up beside me. I was apprehensive having already felt the bad vibe from her. My instincts were confirmed as properly calibrated when she leaned into my space and said “better stop shaking that ass or someone’s liable to put something in it”. I didn’t let her comment phase me one bit and let the music and the lust I was feeling take me over. She stood there for a moment and having seen me unaffected by her comment returned to wherever the hell she came from.
Still lost in the music and the mood, I was suddenly brought back to reality by two hands on my ass. Playfully, two guys from the group had come to either side of me and each had their hand on my butt. It was exciting to feel them enjoying my booty; I was really enjoying my night. They would both go down my thighs, between my legs and somewhat spread my ass as best they could in my tight jeans. A third guy joined us directly behind me with his crotch right up against me so I could feel his excitement. He put his hands on my waist while his friend continued to hold my butt. He reached around to my crotch and pulled me back against him saying “let’s go – party’s moving”.

We arrived to what I could describe as a total bachelor pad. There was a pool table in the living room, video monitors all around, a small but incredibly stocked bar. I had my small bag in hand that contained many essentials for a fun night. The house was already somewhat full of people us walking in made it about twelve, mostly guys. There was a guy that began to use a video camera and the signal was being transmitted to the various monitors throughout the house. I was amazed at the clarity and quality and I could see some pretty hot chicks were putting on a little show. It almost made me want to forget all about my own sissy passions for a moment and go hit on those chicks. But then I imagined how I myself might look on their many screens acting like a whore as the girls were.

Renewed in my sissy-quest, I slipped away along with my bag and found a private restroom in the master bedroom. I felt a little bad taking such liberty, but felt I would make up for it somehow. I removed my jeans which had already served their purpose and put on my favorite stockings and tiny skirt that matched the panties I already had on. I continued to freshen up and just then, there was an abrupt knock on the door. I quickly put on my wig of long flowing dark hair and looked at myself in the full length mirror adjusting my skirt to show the bottom of my sweet sissy ass. I dimmed the light and opened the door and it was “my guy”.

He was confused for a moment, not fully recognizing me at first. I stood there and took his hands and placed them on my hips. They didn’t stay there long and quickly found their way under what little skirt there was covering my sweetness. As he did before, he began to kiss and suck on my neck and I could feel myself slipping away. After a moment he said “we can’t stay here – let’s go” and I grabbed my bag and we returned to the party.

It was an awesome feeling to walk into a room for the first time in full sissy attire. It took a second to get noticed but more and more people were checking me out and of course began the cat calls. I could tell my guy was loving it, he had that smirk on his face like “see – I told she was hot” referring to me. I could see glimpses of myself on one of the monitors nearby which were mostly up-skirt views of my ass (my best sissy feature of course).

I was lead across the room to a bedroom, all the while being touched by guys and girls alike. It was so exciting having the feeling of so many hands upon me. As exciting as it was, I really wanted to give myself to this guy; the guy that truly awoke my sissy passions for the first time. I was very open to whatever else might happen, but I was more than certain he was going first. I felt I was his and if he wanted to share me he could, but I felt this loyalty to him like he had to be the one to take my virgin sweetness. I say virgin which was actually very, very true at the time. The only exception being my favorite toys that I’d often explore with. Like any good sissy, I knew all about my ass. I knew how deep I could take it, how long, how hard, and of course how to make myself cum with my ass. I was always amazed at how deep I could take it, yet how tight I was. I could literally make my thick 10” toy completely disappear inside of me. I would love to dance in front of the mirror knowing my toy was somewhere in me. It was always a lot of work to get it in me and it was always a frustrating experience to get it going. I am without a doubt very tight.

So we get into the bedroom (I assumed it was his) and we started to make out with him behind me. He was still doing all the things I loved to my neck that made me feel so sweet. He kept whispering in my ear how much he loved the scent of my booty from our encounter earlier that night. He asked me to lay face down upon the bed and he flipped up my skirt and just sat there next to me admiring my sweet sissy ass. I loved it. I absolutely loved being checked out and I lay there anticipating what was to come. I could feel his weight shifting and just lay there like a good sissy should. Suddenly he began to rub his lips across my sweet little ass; I could feel his breath on my tight little hole. I could tell after a moment he had licked his lips and his kisses grew more intense and juicy.

With his thumb, he pulled my panties aside to give himself access to my sweetness. I remembered my scent on his finger from earlier that night, especially how it was mixed with the juice from his erection from when I had teased him. His lips pushed against my sweet sissy pussy and his tongue grew more and more daring. First he would kiss my hole with his lips and run his tongue across it; but now he was full on making out with it much like the sloppy first kiss between two much younger people. His tongue forced its way into me and I tried hard to relax. Sometimes it would hurt in a sweet way and I could feel myself clench his tongue and he’d moan enjoying my ass every time I did. As his kisses grew more urgent I could feel his saliva running down my sissy balls. I could feel them constricting from the breeze of ceiling fan above us. They seemed so small compared to his manly accessories he could easily take them in his mouth on demand without the struggle I had when I serviced him.

He stopped and stood up to finish taking off his pants which he had undone while giving my sweet ass a wonderful kiss. I had my ass kissed quite a few times by quite a few women, but they never made me feel as feminine and vulnerable as he did. It was very much the first time of my dreams and time just seemed to spiral while my head spun as the sissy in me had completed the takeover. As he got behind me preparing to insert and I knew I could never take him just like that. I remembered all his manly length and girth from the BJ was so fortunate to have provided earlier in the night.

I tried to tell him “no” so I could kiss his sweet dick in an attempt to get him wet, but he was not willing to wait. Instead he proceeded to rub his engorged penis against the tiny hole he had just ravaged with his tongue. He was expertly using the saliva he had left behind all over my shaved and tiny sissy balls. After a few moments of teasing me, he began to get into a better position to take me. I could feel him pushing against me while the butt-slut I wanted to be fought with the tightness of a virgin ass wanting to defend itself. It seemed to take forever before he started to pass into me. I buried my face in the pillow trying to hide the passion as well as the pain I was feeling. Still like an expert, he’d push his way into me and back out ensuring all the juiciness from his kiss was going inside of me.

Finally the pain and fear I had been felling was replaced with his long hard warmth. After a few minutes I could feel him as deep as my favorite toy; only he felt much different, much softer and certainly warmer than a well lubed toy. Plus my toy never whispered into my ear the things he did. He told me over and over how he was going to make me his bitch and I loved hearing those words. I’d lift my hips with joy each time until the last inch of his manhood had taken me. I could feel his large smooth balls against mine and I nearly fainted in excitement as he told me “I’ve never been all the way in anyone’s ass before.” I was the happiest sissy ever.

Our passions surged and subsided and at times he’d pull all the way out of me and put it all the back in. I could hear the sounds of my juicy ass accepting him. As best I could with his weight on top of me, I would reach behind and hold myself open for him. It was so much easier with one hand which actually felt better because I could feel how much dick I was taking as he would glide across my other cheek. I could tell he was getting more and more excited and I begged him not to cum yet; there were other positions I wanted him to take me in. My begging was of no use and he filled me up with his love and I could feel the change in sensation within me. His cum had a much different lubricity to it than his saliva alone and the feeling was incredible. I felt so sexy and excited because a man had just made me the butt-slut I always wanted to be.

More and more I could feel him gushing out of me as he finished himself off inside of me. I could feel the puddle that had now formed underneath me as if I had also gone in unison with him. But I hadn’t and it was all him. I reached down between my legs and was simply amazed at how much this guy could cum. He had already filled my mouth beyond capacity earlier but this was much different because there was so much under me I could only wonder how much was still inside of me. I arched myself back as much as I could and kissed his face over and over with joy. I felt so wonderful to take him so deep and to satisfy him so thoroughly. It was bliss, pure sissy bliss.

He gave my little ass a few small spanks as he held me open as if to admire his work. And like a real man, he rolled over onto his back, exhausted from his bitch. I could see he was semi-erect and simply couldn’t resist taking him in my mouth. I felt this incredible urge to clean my man like a good butt slut should. I could taste the familiar taste of his cum as well as the sweetness of my ass. I think I’m probably the cleanest sissy ever, so I cleaned him without hesitation as his cum continued to drip from my sweet hole down my sissy balls and some down my leg. His cum gushed out of me several times as my sweet hole returned to its normal tight state.

As If on cue, the door swung open and two more guys walked in. I thought about the monitors with the live broadcast I had seen when we first arrived. I wondered if my performance as a first time sissy lover was watched by everyone there. I hoped they liked what they saw and I smiled wondering what would happen next. I was ready for anything, It felt so good to unleash the butt-slut I always knew I was.

If you like this story, I will certainly continue to tell.

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I had been denying my sissy urges for months... 10 months, felt like an eternity. I had recently ordered a cb-6000s chastity cage and when it arrived I spent 3 days in a chastity induced cock addiction I couldn't shake. My wife miraculously got called out of town for a family issue on day 3 of my self inflicted chastity, we hadn't had sex for months so I wasn't too worried about being caught... almost want it to happen. I got home from work that night and within 5 minutes I was posting an ad on...

2 years ago
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First meeting with Dom sissy mistress

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...

2 years ago
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Crystal

shelf and retrieved the video I was interested in. Her skirt barely hid her pronounced buttocks, and the slight smell of sexual excitement was in the air. seemingly, we were the only ones in the store at that time. "This video is hot, hot, hot," she said as she turned and bumped into me suddenly. Slightly flushed, I could tell her temperature was rising as we headed toward the checkout stand. I could hear the heavy "Swish" of her wetness as she walked toward the counter. "My husband and I...

3 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...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

3 years ago
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Dark Crystal

The Dark Crystal (revised and updated) by Olivia Evans "Any sufficiently advanced technology is indistinguishable from magic." Arthur C. Clarke The Dark Crystal? is a key major component of the standard survival kit of a starship. Intended to be used by shipwrecked survivors to make modifications to their bodies in order to survive in otherwise hostile and deadly. Depending on the environment some changes are merely cosmetic and minor, others involve complete restructuring down...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

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