a single night of sex (with a man)

My first turned me  …fabulous

I’m lying in the bed of a man who picked me up outside a gay bar a few hours ago, listening to the sounds of his gentle, contented sleep. Contented from my having given him delicious head, contented from him having fucked me with my stockinged legs wrapped around his shoulders. I’m lying here, looking at the trail of clothing that marks our evening: my strap-y heels, an exquisitely hand-painted silk scarf and tube mini-skirt just inside his front door, my bangles, earrings and necklace at the far end of the bed and next to me a little camisole top and a gorgeous leather bag with its usual date-night collection of lotions, condoms, spare undies and makeup.

I know I’ll have to get up, skip into my panties and top and go to his bathroom where I’ll put myself together, but before then I will continue to lie here, grateful for the sensation of fullness that lingers for hours after a man has pulled out of me and about the memories of this evening, of our passionate kisses, his sucking on my earlobes and nipples, of my exploring his cock with my lips and my tongue, about how i love the smell of the man on my face and neck, and about his taste.

And lastly, I will think about the fact that it’s only Tuesday evening, and that there’s a whole week’s worth of men I’ve yet to meet who will want me as their sissy cum slut!

I wasn’t always like this. In fact, it was only a few years ago that the world knew me as a somewhat unremarkable guy, a hard-working, mid-30s, professional who kept pretty much to himself but who, everyone agreed, was a good guy to have as a friend. Kind, considerate, responsible. Of course, what no-one back then knew was I’d long had had a nagging question in the back of my mind on what it would be like to be in bed with another man.

I considered it a fairly simple wish; a single night of sex with another man just to say I’d “tried it.”

Like most guys of my generation and background, I’d had my share of exposure to gay sensuality. There was an old roommate who once insisted on taking me gay bar-hopping, getting me kinda drunk along the way, and launching into some pretty sloppy and wet making-out in the front seat of his car. There was the guy I met on a hiking trip who found his way into my tent one evening to give me a hand job. And a drinking buddy who an annoying habit of giving long on-the-edge-of-passionate goodnight ‘hugs’ and who finally kissed my ear and asked if I wanted more. I had always declined to reciprocate because, I told myself, it wasn’t who I was. I had girlfriends, some platonic some not, and while I could never have been considered movie-star material, I was content in my modest sex life.

Years passed, my career seemed to progress nicely enough – I still had girlfriends but to the ongoing amusement of friends and colleagues, I had yet to meet “the one. And always, in the back of my mind, sat the “what would it be like” question. Society’s openness to accepting being gay had advanced dramatically over the last decade and it became clear to me that it was finally time I did my touristic excursion into an evening of gay sex. One of the alternative newspapers in San Francisco gave me a wealth of options as I cruised through the M4M personal ads. I came across one from a “caring and supportive gentleman” – Brian was his name – “who loves to take men on their maiden voyage.”

We met at his house in a kinda posh area in Marin County, had some awkward small talk in his living room and at a point when he must have thought I was ready, led me by the hand to his backyard studio that had little more than a futon, a bed-side table with a hand-pump jar of lubricant and a tasteful little bowl of different packaged condoms.

The moment we started kissing I knew something was just very ‘right’ about this, this moment, this decision. Without thinking, I found myself un-self-consciously stripping off my T-Shirt, my jeans, and my boxers – and in doing so developed – to my surprise and undoubtedly his pleasure – a lovely hard-on. We stood there, him fully clothed and me naked, embracing, kissing, fondling. When he took me into his bed where I undressed him and found myself almost immediately sliding down to between his thighs where I began kissing. The kissing moved up. And up. And soon I was licking his shaved balls, completely comfortable with something I had never done. And then, I started on his cock. I loved every aspect of it, its smoothness, the softness of the skin and the hardness of the shaft, the cute head and the oh-so-sensitive spot just at the base of it, it’s musky sweetness. I loved how he responded and I was utterly thrilled that I was the source of that erotic pleasure.

I remember reaching around and massaging Brian’s ass, and looking up into his eyes. He smiled down at me and uttered something that will stay with me forever; “Oh you ARE a natural cocksucker aren’t you? You will soon LOVE thinking of yourself as submissive sissy… trust me!” And I found myself, in a soft almost feminine voice that came from .. who knows where? .. saying “ohhhh darling, yesss…yesss…yesss!”

We spent the next hour or so as I learned the mechanics of gay sex, but more importantly, learning something about my very essence. I went home that evening and fought back waves of emotions. What had I done? What just happened to me? What was I feeling? Was it real? Was this the real me? And maybe most tellingly, how could I put this behind me and return to my normal life? My goal, my simple wish, had been fulfilled. It was time to move on.

Two days later I got a call from Brian and he coyly asked if I would like to come by to get either trimmed or shaved ‘down there’ because “you know, it is SUCH a sexy thing for a sissy cocksucker to be totally smooth” There is was again, a reminder of how he saw me, a sissy cocksucker. The memories of those hours in his studio along with the sound of his marvelous voice made me melt and I said I could be there early that evening. I rationalized the visit that evening with him as a final gay encounter, that I would thank him for his kindness, his patience, and his gentleness.

He met me at the door wearing knit boxers that covered everything – but hid nothing, holding a glass of wine to invite me in. We embraced, kissed, he played with my nipples and rubbed me through the front of my jeans. We drank more, embraced more, and as I got increasingly horny he said “well, time for what you came for.”

Back to the studio and he took out an electric razor and started on .. my legs!

“Wait.” I cried, “I thought we were talking, you know, crotch!” He laughed and reminded me that such “gifted cocksuckers are smooth everywhere, except…” and again words that will stay with me forever – “except maybe in a little tuft of pussy fur that you’ll use to turn men.” His words flowed through me like nothing I’d never known. I was his. For Brian, my darling sexy Brian with his full lips, his firm body, his beautiful cock, I’d do anything and he could do anything to me. A half hour later I looked into a full-length mirror to see a reflection of myself with hair in precisely two spots: atop my head and within an impossibly tiny triangle surrounding my cock. It was, I was … lovely.

Over the next several months I would go back to his place at least twice weekly. For sex with him, for 3-ways, and for enjoying porn together on his huge screen TV as we masturbated each other, He was a loving and patient teacher and I began to realize how much of a willing and receptive submissive I was turning into.

We started branching out. He and I started going to gay saunas and baths, we went to sex clubs, i would don corsets and bustiers to go to fetish and fantasy dungeons, we went to costume parties, and private gatherings.

And my changes were dramatic. I was turning into an utterly fabulous queer. I started growing out my hair and going to salons for coloring and styling; i shaped my eyebrows and got full body waxes, I became skilled at makeup and my wardrobe evolved to something in between Forever 21 and Victoria’s Secret. I had become an unmistakable femmy slut. Brian loved it. I loved it. As did many – many – men.

The point of all of this is all began with a simple wish. I wanted to see what a gay encounter felt like. It was to be a one-time visit to another way of being. In fact, as I later realised, my encounter with Brian was like having a switch flipped. A switch I’d never known about but nevertheless, a switch once toggled that could never go back to where it started from.

I have become a new person. A better person. I take pride in my feminine attributes and mannerisms, I love being pretty, I love feeling the kind of power I have over men with my sensuality and I love – no – I live for – the pleasures a man can give me. I’ve begun full body electrolysis and just in case anyone doesn’t see me as the sissy I am, I’ve had large areola tattooed over my nipples and on my upper right thigh, the tattoo of a fabulous wedding garter. My unremarkable male persona is gone forever; I wake up thinking of cock, I stare at men’s bodies throughout the day and am shamelessly flirt-y whenever I can, and in the evenings i dress up in anticipation of the unbelievably satisfying eroticism of having a man who will fill my boi pussy.

My advice to all you bi- or gay-curious darlings Out There who might be thinking of the briefest of visits to ‘the other side?’ Be careful what you wish for. I’m not saying it won’t be for the best, but, be prepared for the possibility of a one-way trip to become someone very, very different.

Thank you J from Mistress Alexa – some of my favorite clients will love this!

Pelvic Floor Fitness Is Hot!

Mistress Alexa tests her sissy recruits with the latest feminization exercises before she converts them into happy life-long clients.

“This is it, sissy-girl. This is your only opportunity to prove to me that you are worthy of being turned into a woman!”
Before I take you on, before I rub your breasts with estrogen cream, and watch your rosy nipples bud like a bride, before you grow an ample bottom and a full womanly shape, I will test your pelvic muscles and see whether you are ready to be my client.

Then she covers your shrunken little maleness with one leather glove, and hikes up your skirt with another. Bend over, she says, “You will be tested on your muscularity as a girl, not as a boy.”

Smoothly and quickly she pulls down the panties off your behind and positions her gloved finger. “I have found the “sit-and-squeeze” technique is boring, so we are going to use the LOOP on you.”

LOOP is a complete fitness system that provides real-time results that I can see and feel. You will contract and relax your pelvic floor muscles as though you are lifting weights with your pussy hole. You will complete a certain number of repetitions and I will time them.”

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“How Does LOOP Work?,” Mistress Alexa asks.
“I will tell you,” she says, inserting her finger in and out of the test area, then connecting the Bluetooth-enabled mobile device via a free app that offers pre-programmed exercise routines and visual feedback she can see every time you squeeze. “LOOP’s high-accuracy pressure sensors detect even the slightest muscle movements and map out those movements on my screen. Squeeze, Girl! Again! Again!”. Mistress Alexa continues with the exam.

“LOOP is designed to fit and function with a woman’s intimate anatomy. Its asymmetric shape makes it easy to insert, comfortable to squeeze, and easy to adjust and twist for a perfect fit — if you are a woman.” “If you are a sissy, if you have been practicing …with dildos, with balls, vibrators, ticklers… it should be a treat!”

“Then… you will dress up for me and I administer the Smartballs test. The Smartballs Duo by Fun Factory is a vaginal exerciser used for increasing PC muscle strength and overall vaginal tone. Alexa uses the double ball version to test for strengthened PC (pelvic floor) muscles. The ball inside of the Smartballs moves and “vibrates” when you move around, do your chores, service your mistress, dress up, masturbate, and pose for your Sissy Photos. The more you do, the more the vibrations inside you stimulate the sissy muscles to contract.”

“Personally, Im LOVING this heavier set of Smartballs. They are more disruptive internally but travel friendly. No one can tell when you’re wearing them — another plus. This means I can send my sissies out to work wearing SMARTBALLS…”

Pelvic floor fitness is hot! It is also Alexa’s favorite way to make sissies more like women, chemically, hormonally, and pelvically….



I always knew I was a cocksucker. From the moment that I looked at cocks in the shower  after playing football, or soccer, or hockey…

As a teen I was able to pick up men. I learned to suck them off – without hands. That’s also where I learned the beauty of the uncut cock.
I had all these girlfriends who would joke to me about different things, but I didn’t really get it.

They would tell me that I was a pretty boy, or they would tease me about putting on their panties, and sometimes they would take me shopping with them because they loved making me try on panties in the dressing room.
One of them started taking photos of me in drag. I didn’t think much of it until she showed me a roll of film with me in lingerie, in stockings, with a garter, with lipstick, shaved, smiling, cherry ready to be picked.
One day I walked in to her apartment after work, looking hungry and usable, and found her with a black man in bed; her on top, his 9 incher sliding into her from below, glistening, hard, veiny, and uncut.

I got hard watching… him, not her.

And that night when I came, I fantasized about him, not her…

Mistress Alexa, Make me gay!


Amanda’s Adult Store Fantasy

Hello, Alexa:

I am having my adult store fantasy again. I hope we can do it for real soon.

I’d start by calling you and making sure that we could make a day of it. I’d start at home, and call you and start preparing myself. I’d take a warm bath with some girly scented bath oil. And then I’d call you as I gave myself an enema to make sure I am squeaky clean for the time to come. I’d get dressed and you’d tell me to wear a pink shirt and give myself a hint of perfume before setting out.

I’d get to the store and I’d be very nervous. I’d be texting you on the phone to tell you I was there. When I entered the store, I’d make my way over to the lingerie section. A salesgirl would come up to me. Unlike the last time I was there, I can see that she was sharing some knowing looks with some of the other salesgirls. She’d look me straight in the face and ask me, “can I help you?”

I’d look down and mumble something like I was just browsing. She’d step a little closer and say, what’s your name? I’d say my man’s name. She’s say, “no, I mean you are Amanda, right?”

I’d be stunned, even though this was unexpected. That means that you had called the store and let them know I was coming and my fantasy name. I don’t know at this point if you had told the whole name.

I’d be blushing and say, “yes.” She’d giggle and share more winks with her friends. She’s day, “Alexa said you would be here and I’m going to make sure you get what she wants you to have. Looks like you are in for quite a night.” Then she’d tell me to call you, which I would. I’d call and tell you I was here and what next. You would tell me it is time to buy some frilly lingerie and to hand the phone to the salesgirl.

At this point, she would be very nice and be chatting with you, looking over the rack and choosing a whole intimate outfit. She’d hold items up to me to see how they might look. She’d tell you she was getting me a nice teddy, maybe a corset, a bra, all matching course. She’d check with me to make me say things, like–you need stockings now, right? And a garter belt, right? And I would have to respond to this stranger that I wanted these things.

Then she’d say, “It’s time to get some panties.” And then shed choose some to go with the other lingerie and get a few more pairs “to wear under my male clothes.”

But the embarrassment was just beginning. Then she’d say, “its time to get some toys–follow me to the anal section, Amanda.” And she wouldn’t say it to quietly. We’d look at some of the butt plugs and other toys. She’d still be talking to you and say, “Alexa said you already liked one of our big cock vibrators–show me which one.” I’d be embarrassed and show her the one that I took before. She’s say, “wow, Alexa said you took this whole thing in your ass, is that right?” And I’d have to admit it was. So she’d pick it off the rack and put it in my basket. Then she’d say, “Alexa says you like a smaller warmup vibrator, is that right?” and she’d pick a nice pink one out for me. Then she’d tell me that you told her I needed to take something even bigger to “stretch me out”, so she’d pull an even bigger lifelike dildo off the shelf–a full 9 or 10 inch realistic looking black cock dildo. “You like these black cocks, don’t you?”

Then she’d pick out at butt plug and tell me that you told her to get that, too.

Finally she would take me to pick up nipple clips and a few other things. Then she’d say, “do you need some lube?” and I’d say yes. We’d go over to the lube rack and things would get even more embarrassing. “what do you need it for?” she’d ask. “I need it for the vibrators.” “Is it for you or someone else?” (she knew the answer, but was making me say it). “For me.” She’d direct me to her recommended lube for sissies who fuck themselves with dildos. I’d think I was done, but she’d say, “don’t you need some more?” I’d be confused. She’d say, “don’t you need some to jack your little dick?” Mortified again, I’d admit that I do. “Of course you do. Now tell me what you need it for.”

“I need it to stroke my little dick.” “And what is your full name?” “Amanda Littlecock.” “That’s right, Amanda, you little sissy. All the girls here know your name. We all drew straws to see who would get to help you and I won. So come over here with me.” She led me to a darker corner of the store and a couple of the other salesgirls came over. “Show me your little dick, Amanda Littlecock.”

I wouldn’t know what else to do but obey, so I’d unzip my fly and pull out my cock, which had been hard the whole time. All the girls would giggle at it. One would take a photo. “I’m sending it to Alexa. She said she wanted to see how small it was. You are doing the right thing dressing in this lingerie and fucking yourself, because that little thing isn’t a real man’s cock. Put it away so I can stop laughing, little bitch.”

“OK, Amanda. One last thing. I’m going to keep your things here in this basket, but you take this lube, this butt plug, and these panties and go into the bathroom. Make sure your little dick is hard when you come out, because I don’t want you to jack off when you are in there. When you come out, you will have the plug in and panties on and your nasty man underwear in your hand. I’ll keep your phone to tell Alexa how it is going. Meet me at checkout.”

I’d be like in a fog. I’d go into the bathroom and do as she said. I’d be sorely tempted to whack off, but I wouldn’t want to risk the session I know was coming with Alexa when I got home. I’d pushed the plug in and felt that lovely full feeling, and I slipped the panties on. I pulled my pants back up, looked at myself in the mirror to fix my hair, and went out to the checkout as instructed.

When I got there, another salesgirl was there with her. She’d point to the trashcan and say, “throw your old underwear in there. Those are only for men.” Then we’d go through the long process of testing the vibrators, buying batteries, etc. I’d have to touch every vibrator as it buzzed and confirm that I’d like that. All the while, she’d keep up the chatter. “I really like this one–it makes me come. I think you’ll like it in you, too. Did you really take this one all the way in? You must like stretching your ass. Amanda Littlecock–that’s really cute. My friend here said you have a little sissy dick–is that right? Let me see the bulge–is it hard now? I can hardly see it, but I see the little mound.” People in line around me were giggling.

Finally, they gave me the phone back and you’d tell me to head back to my car and call me. The salesgirl I spend the most time with would walk me out. “Have a great time with those toys, Amanda. You will look adorable in all that sissy lingerie.” As I’d leave the store, she would give me a hard slap on the butt to jostle the plug–“have a nice ride home. By the way, that pink shirt is just right for you.”

Plugged, perfumed, humiliated, and shaking with excitement, I’d sit in my car, wiggling on the plug. I’d call you and tell you I was ready. You’d say, “Let’s go to what’s next.”


Anyway, that’s what I’m thinking about. Looking forward to talking to you next time.


Loving your control over me.

Hello Mistress. I can’t stop thinking about You and Your beautiful voice inside of me, changing me, little by little. It’s inevitable, I’ve become Your slutty little whore, hanging on Your every word, waiting for any opportunity to prove myself to You. My beautiful, powerful Mistress, please control me. I need You to take possession of Your filthy, sissy whore and force me to take female hormones so that You can then force me to do things I can no longer say no to. Please Mistress, allow me to prove myself to You. Let me prove to You how I can generate income for you swelling my slutty lips, tongue an throat by sucking men willing to pay you for it. Force me to make my slutty sissy body more usable and purposeful for You by opening my sissy pretty legs in the air to be taken by real men who desire little sissies like me to swallow their cum. Force me to stick my pretty ass in the air to be taken and have long thick beautiful cocks penetrate my pussy. Please, pleeease make my more useful to You as your prized transsexual panty wearing slut. Fill me with your words and thoughts turning me into a beautiful woman for Your use, Your pleasure. Fill my every hole with men’s cocks and cover me with their cock nectar. Have me drink of the pleasure your control over me provides. Take me and mold me into your slutty transsexual for Your pleasure and use. Your pretty pink baby doll wearing sissy panty slut waiting to be whored for Your usefulness, M.

PS please give me a sissy name like Jessica or Monica so I can feel prettier. Loving your control over me.

Faggot Slut

Role-playing: you tell me to go to a web site where you are masturbating and turned out. You look like a girl, and it takes me a long time to recognize that you are you. A slutty underwire bra and stripper’s panty hug your new sweet female body, and your mouth is moving up and down along a long mocha colored cock. One brown hand is on your cheek, reminding you that your fundamental purpose is to suck cock, and so you do. You are half excited, with one finger up your ass, getting yourself ready to be a faggot for an other big black cock…