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You’ll have butterflies in your tummy when you see him

Still smelling of the bubble bath where you’d soaked after shaving your legs, as you read your romance novel, you finished off your nightly skincare routine. You loved how much better your face looked after the laser treatment, and it made it so much easier to be really serious about your routine without that gross hair making you feel weird. You looked at the time and realized it was later than you thought. Time to get some sleep.

It took you a minute to find your phone, but there it was, right where you left it earlier on the couch, where you sat with your tea after work and watched some of your favorite Vogue beauty secrets videos on YouTube. You set your alarm for the morning and went back to the bedroom for the night.

There it was, next to the bed, standing upright on the nightstand. Not it, there He was. Mike. You picked up the hefty dildo and kissed it on the top gently. “Love you, baby. Good night.” You thought of his solid frame and confident swagger. The way he walked through the office like he owned the place, despite being younger than most of the other executives. His chiseled jawline and piercing, intelligent eyes. You gave the shaft a gentle once over with your soft hand, then kissed the head again, for a bit longer this time. Again, with your mouth still touching it, you whispered, “I love you,” this time a bit more slowly.

You turned off the lights, then pulled back your duvet and climbed in on top of the silk sheets, your smooth and hairless body gliding on the soft surface. You smoothed out your nightgown and absently touched your flat metal chastity cage. For whatever reason tucking didn’t feel right at night. You preferred the cage, which didn’t pinch as much as being tucked as you tossed and turned in your sleep, yet still prevented your body from attempting a nocturnal erection, even though you were pretty sure you weren’t capable of that anymore anyway. Better safe than sorry, right?

After remembering a few things you needed to get done, your thoughts drifted back to Mike. Images of the two of you holding hands at a romantic restaurant, walking along a beach at sunset, sharing a profound conversation while watching the sun rise. Him strutting around the office, better than everyone but not arrogant about it. You wondered what he was doing right now, thought about him in his bed. Did he ever think about you as he drifted off to sleep? Maybe he sleeps naked…

You reached over in the dark to your nightstand and grabbed the dildo, rubbing it against your face, nuzzling it. “I love you, Mike.” You kissed the tip again, lingering for several seconds, then kissing more, gently sucking on the head as you tickled the shaft. His face in your mind, his powerful hands. You moved your mouth down the shaft, wetting it with your saliva. Slowly up and down, a little further gradually. Picturing his powerful body above you, imagining running your fingers along his abs. Sucking greedily now, hearing his moans in your mind. You imagine he unleashes a torrent of hot semen into your mouth with a loud groan of pleasure.

As you reach down to your cage, your soft penis, imprisoned in its metal confines, has leaked your runny juices into your panties. You gather up as much as you can and bring them to your mouth, imagining it’s his cum, earned from your mouth’s zealous attention. His wouldn’t taste like this, you imagine. It would be more… manly. But it’s the closest you have.

Again, you place the dildo on your nightstand and sigh. “Goodnight, Mike. Daddy. Goodnight.” You drift off to sleep, the taste of the dildo and your secretions mixed in your mouth.

————-

It’s the next day, and you sit as your desk, boy clothes covering your smooth, soft body. You do your best to look stylish, but omg male clothes are so boring. Ugh. You’re always wearing a pair of cute panties, your little male bits securely tucked away, but over that… blah.

Your desk is near the other secretaries. People call you “the girls” collectively, and that always makes you happy. It’s a holdover from before you were hired, when the company had never had a male secretary. Well… “male.” You know, close enough. You’d gotten friendly with the “other” girls, after there being some separation at first. It had been awkward to have a man as a secretary, but they figured out soon enough that you were just… you, you know? Not really a man, not like that. They never asked you about your sexuality, but you were pretty sure they could kind of tell. Maybe more than kind of?

You hung up the phone after transferring a call to Mr. Santos and almost gasped when you saw him. Mike, right there at your desk, waiting to talk to you.

“Morning, Bobbie.”

Your legal name was Robert but everyone called you Bobby. You always imagined them saying Bobbie instead of Bobby though. So much cuter that way.

“Oh, um… hi, Mike. How are you today?” Your cheeks felt like they were on fire. His hand was on your desk and you marveled at how powerful it looked sitting there. The things it could do to you…

“Good, good. Hey, would you be able to call Chesterton and make sure they send those forms on time this week? The brass really doesn’t want another order to get delayed. If they give you any pushback, let me know and I’ll handle them myself.”

You could smell him. Clean, fresh, but like… strength? He smelled so good. You had a silly smile on your face.

“Sure, I’ll get that done right away, Mike! I know the girl who handles those forms, she’s super sweet, shouldn’t be a problem. But I’ll let you know if so, okay?”

“Thanks, Bobbie, appreciate it.” And he walked off purposefully. You didn’t know you were holding your breath until Stacey spoke and snapped you out of it.

“You in for lunch today, Bobbie?”

Stacey was super sweet, cute despite being a little past her prime and a few pounds overweight after giving birth to two kids. She always contoured a little too heavily but took super good care of her skin, which really helped at her age. The subtle, tasteful wings on her eyeliner were a bit uneven today. She had a new manicure, which you noticed first thing this morning and loved. The accent nail went perfectly with her earrings.

“Of course!” You inhaled sharply, still visibly flushed, as your eyes never left Mike while he walked away down the hall. As he rounded the corner, you turned to her. “I meant to tell you, your nails look so cute, by the way.”

“Oh my gosh, thanks! I tried this new place my sister told me about and I think I’m gonna go there from now on.”

“Totally. Big w for your sister.”

Alicia, two desks down on your other side, broke into the conversation. “Maybe at lunch we can talk about Mike,” she giggled. Alicia was funny but sometimes didn’t know when she’d crossed a line.

“Alicia!” Stacey whispered sharply. “Be nice.”

“I’m just saying. I think Bobbie would enjoy that conversation.” Another one of the girls giggled under her breath. You didn’t notice who.

“Anyway,” Stacey started up again, cheerfully, “maybe that new sandwich place down the block. I hear their salads are so good.”

You knew you should feel embarrassed, but for some reason all you were focused on was the spot on your desk where Mike’s hand had been a few moments ago.

You weren’t gonna wait until after your bath and makeup videos tonight. You were gonna get home, change out of your boy clothes, and head straight for your nightstand, you already knew…

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What you put in is what you get out!

(Reminder not to actually do this. DIY hormones can be very dangerous, I just thought the idea of this was really hot)

Good girl! Now, check out this lip gloss I discovered…

Do you know any cute single guys she could date instead?

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You can have sex with men, obviously. Women aren’t an option for you in that regard. But it’s good for you to view men with suspicion, as dangerous, as different. Get your head right, babe

It’s not for you. Don’t be a disgusting animal and ogle her when she doesn’t want you to

Your fetish has a cost, babe. But maybe that’s what you wanted all along…

Your jokes are literally the funniest!

She just continues her monologue about her jerk of a boyfriend while she changes clothes, completely at ease around you, because literally why wouldn’t she be?

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Is it true that the more that men make me cum, the more attracted to them I will become?

Well, that’s complicated. It’s true that classic Pavlovian conditioning is a thing. If you get pleasure while you’re exposed to a certain kind of stimulus, your brain will unconsciously begin to respond more positively to that stimulus on its own.

Here’s the obligatory part where I have to point out that I’m not saying you can change your sexuality. People have taken me to task in the past when they think I might have implied that. The last thing I’m doing is advocating for conversion therapy when I’m talking about this stuff. But like, it’s kind of part of the fetish, you know? Idk what to tell you. I’m not going to explain more because it ruins it, to the point where I almost didn’t respond to this question. We’re all just having a good time here, okay?

Now that we’ve got that out of the way, I’ll repeat myself and say a totally straight man isn’t going to become gay if he cums to men enough. That’s just silly. But you can, let’s say, encourage certain impulses that are already in your brain if you go about it intelligently. So how do we do that?

I’m not going to explain all the Pavlov stuff, which most intelligent people should already know about anyway. But the basic idea is, you give yourself positive reinforcement for the stimulus you want to build positive associations with. Make sense? Good, let’s apply it to what we want to do.

So the basic outline is just like you said, let men make you cum. But what does that mean, exactly?

First, a lot of sissies will cum to pictures or videos of cocks. I don’t think that’s the way to go. A closeup of a cock depersonalizes things. It’s just a disembodied sexual organ. It might be a hot take, but I don’t think it’s necessarily “gay” for a man to cum to cocks. A hard cock means sex, it’s an unmistakable symbol of sexuality. So to some degree it’s sexual to everyone, even if most straight men will have some repulsion towards it.

No, what you really want to do is just what you said, have MEN make you cum. It’s great if the men are naked, and it’s great if you can see their dicks. But you should be able to see the entire man, not just his crotch. You want to build associations with men, and that means entire men, not just body parts. Switch it up too! Maybe sometimes fully clothed men: focus on their handsome faces. Maybe sometimes partially unclothed men… ugh, their powerful chests and arms 🥵

Second, don’t just rub one out in a hurry. Take your time, make the entire experience as pleasurable as possible: dress up, put on some music, light a nice scented candle, get comfy. Let all your senses be happy while you’re looking at men sexually. They all send messages to your brain that your brain will remember for the future.

Normally I wouldn’t say it’s ideal to masturbate like a man, but while you’re doing this just masturbate however is easiest and most comfortable to you. If that means stroking your sad little dicklet, it’s okay during this process. You just want to feel good.

It’s better if there’s some emotional connection behind it. Have you just finished watching a romcom? Hopefully you were aggressively empathetic for the female lead and falling for the male lead along with her character. Try masturbating to him while thinking about your feelings during the movie. Pretend you’re the female lead. Get your heart into it. Remember what we talked about, the more ways it makes you feel good the better, and emotions are SO powerful.

Let him make you feel good!

You’re going to want to do this over and over. It’s not just an activity, it’s a whole process. Do it as often as you can, commit to it as much as you can, and it will work better.

You’ll see a sexy man and your brain will start to think, oh, that’s the kind of person that makes us feel good sexually. And that’s exactly what you want.

There’s another side to this. You want to feed the man = sexual pleasure association, but you want to starve the one that sexualizes women at the same time. This is important for a couple of reasons. First, if you ONLY get sexual gratification from men, it’s easier for your brain to make that connection. If you’re still orgasming to women, however, it’s harder for your brain to connect its pleasure to men because it doesn’t always come from men. Second, we don’t want to look at women sexually anyway, do we sweetie?

So you should absolutely not be looking at women when you’re having your little sexy time or it just ruins everything. We don’t want your brain to get confused here, we want to keep the message very simple and straightforward. Men are for sex, women aren’t.

Solo male videos and female POV videos are fun, but there are so many pics of hot guys, clothed and unclothed, that you can look at too. Just make sure there aren’t any women.

But that’s not all! I want you to watch as much content with women as possible in a NON-sexual context. Women women women all the time, not being sexy, just being normal. I’ve talked a lot about makeup tutorials, but it can just be any women doing regular stuff. When you’re seeing whatever content you consume, your brain should expect to see women.

That makes it even more pronounced that when you’re making your little cummies, there are no women to be seen. You’re used to seeing a woman talking to you, women talking to each other, women going about their business. But when you get sexual gratification, there are no women anywhere and that only reinforces that sexual pleasure comes from men.

You can also incorporate negative reinforcement into your routine, but that can get kinda dark and so I’ll leave that to your imagination because we’re all sugar and spice and everything nice here 😇

Take it into everyday life too! In some ways this is the most important part. Start to look at men you see in the world as potential sexual partners, potential boyfriends. Evaluate them on their looks, their bodies. Conversely, if you find yourself having any sexual thoughts about a woman, gently remind yourself, “no, that’s not right for me.”

Do this for a long time, regularly, and stick to it. Then who knows, maybe you won’t even need the help anymore? 😉

She knows you just need a little push, but this is the best thing for you

Id like to start by saying i love your work. As someone who quits often but comes back at what point should I start committing, like is there a point where this is just my truth. Also what do I do to make it more of a for sure thing like I cant quit you know? 💖💋

I guess it depends on why you’re quitting, doesn’t it? Not all purges are the same. I think some people purge because they’re in denial about their own desires, some get scared, and some try to consciously will themselves to be something they’re not.

In general I think accepting yourself for who you are always helps, but that’s not necessarily going to address your situation because I don’t know why exactly you want to turn away from this side of you.

I also want to make it clear that it’s not the end of the world if you do purge. Sure you might throw some stuff away, but those are only possessions. Possessions can be replaced. Desires come and desires go. It’s natural to want to step back sometimes when there are other things in life to focus on. You shouldn’t beat yourself up about it.

Having said all that, your specific question was how to make it so you can’t quit. If that’s what you want to do, it’s simple. Tell people. If people know, you don’t have anything to be afraid of. Once you’re no longer scared of people finding out or living a double life, I think you’ll find the desire to quit is also gone. Your desires can wax and wane, as I talked about, but it’ll just be an aspect of you that’s always there at some level or another.

You can also do things you can’t take back. Start laser hair removal, get a girly tattoo, incorporate more feminine elements into your wardrobe and wear them publicly. At a certain point it just becomes silly to think about “quitting.”

When you’re talking to someone, think about how your new role model would express what you’re thinking. Pretty soon it will just be how you talk, and everyone will be able to see you for your real self 💅

She thought it would be a fun way to spice up your marriage. But now you’ll be a cocksucker forever and that’s not what she wants

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You don’t really have the right mindset if you have to think about it. Of course you see it her way, she and you are alike! Why would you have to think about it? Maybe he’s in the right, but he has to overcome your initial bias to prove that to you. You know what team you’re on 💅

christina-tiara

Hi Sissies!! Happy Pride 🏳️‍🌈

If you’ve followed my blog, there’s a good chance you’re a sissy looking to have sex with men! I’m here to help you with that 😘

A little background on me first! 5 years ago during pride, I worked up the courage to hookup with a man for the first time! Since that night, I’ve hooked up with dozens of men dressed as Christina.

I’ve learned a lot in that time and wanted to pass on some of that knowledge to any sissies who might be taking their own leap into the world of gay sissy sex this pride month!

A picture of me right before I had my first hookup with a man.

Are You Ready for this Sissy??

The first step is to admit to yourself, “I’m a Sissy. And I want to have sex with men.”

For some it’s not hard, but some sissies still hang onto their heterosexuality. This won’t be a fun experience if you’re constantly second guessing yourself. You need to commit. You can tell yourself you’re just experimenting, but at the end of the day you need to accept you want to have gay sissy sex. Just enjoy it.

Now that you are going to finally let your sissy side have some fun, how do you get ready?

If you’re like me, I was dressing up well before I had sex. And nothing makes a sissy feel sexier and hornier than looking pretty. Never shaved your legs? It’s time. Do you only wear panties? Time to upgrade your wardrobe. Still learning makeup? Lock in sissy.

No shortcuts. No half measures. It’s time to bring out your inner woman. 💋

Finding Mr. Right

You’ve accepted this is happening. You are confident and looking your sissy best! Time to find your man.

Tell me sissy, what is your type? Ever thought about it before?

Personally, I love a tall, strong and dominant man. I love if he dresses nice, has a little facial hair, and if he has big muscles. While I won’t find exactly what I’m looking for, it’s important to set standards. With all this in mind, he has to be in good shape, 6ft, and clean up nicely.

Think about what kind of man you want to be pounding you sissy pussy and don’t settle. There’s plenty of men who want to fuck sissies and if you settle of a mediocre guy, you probably won’t have as much fun as you’d like.

Wow! Isn’t he sooo hot 🥵

Anyways Sissy! Where do you find your man? You’re probably not going to many coffee shops dressed as a sissy.

I have 3 places I find men.

1. Grindr - I find 90% of my hookups on Grindr. It’s full of guys looking to fuck asap. Don’t be shy when filling out your profile. Tell them what you want and post pictures. No one is going to find you and expose you. Especially if you’re in full makeup. The big downside is not every guy understands the sissy fetish on Grindr.

2. Fetlife - It’s less of a dating app but more of a kink website. The guys you meet will definitely understand the sissy kink. The big drawback is most men won’t be local or they are looking to sext. Good for online fun. Not so much for irl hookups.

3. Reddit - This one seems weird but I’ve met a couple guys off Reddit. There are subreddits like r/sissypersonals where you can put out personal ads looking for hookups. Kinda gives Craigslist vibes. I get tons of suitors messaging me here but again not all are serious!

On a side note I have the second most popular post on the sub. 🥰 insane to think 900,000 people have seen my sissy self!

Here’s some general advise in finding the right guy on these platforms.

No Profile Picture = Will Waste Your Time. I’ve never had anyone that anonymous be serious about meeting up.

Ask Questions.

“What all are you looking for on Grindr?”

“What are you into in the bedroom?”

“Are you clean and recently tested?”

Don’t assume he’s into everything you are. Personally I dislike having men touch my clitty. So if he’s really into that, I know it’s not a good match. Don’t let him get away with saying “i’m into everything” because that’s never true. But share what you enjoy and your limits!

Also for your safety make sure he’s tested and can show you a recent std test. You can also ask him to wear protection. Personally, im on PREP and recommend other sissies to take preventative action for peace of mind. 😇

Just make sure he makes you feel hot and horny but also safe!

The Meetup

So you found a stud who checks all your boxes. It’s time for the main event! If you feel extremely comfortable with him you can invite him to your place. But I personally love the first meetup to be a neutral third place like a hotel room. It’s a bit safer that he doesn’t know where you live. Just incase you don’t want to meetup again.

In my experience most of the time he will offer to split it, if not just pay for the room. For me it’s important I book it. Make sure it’s not a shady hotel and if I’m there first I can spend the afternoon in the room getting ready for him.

I usually send him a pic like this too. It lets him know what exactly he’s getting.

It also gives you an opportunity to make sure you’re shaven smooth, your makeup is perfect and your enema has cleaned you out. Additionally, I’d bring a dildo and some lube. Bouncing on your dildo before he arrives will both stretch you out and make sure the enema left you squeaky clean. You can also leave your butt plug in until he’s ready to fuck you.

It can be a little nerve-racking waiting for him! I like to dim the lights, have a couple glasses of wine and play some Ari or Sabrina to put me in the mood. Before you know it he’ll be knocking at your door!

Gay Sissy Sex

You take him to the bed, get him a drink, now what?

Do what comes natural and let your feminine side take over. He expects you to be a girly little fairy. It’s okay! You can be who you truly are.

Makeout. Feel his abs. Let him grab your ass. Have fun! But sooner or later you’ll be on your knees looking up at your man. It’s time to suck his cock! 🫦

Sucking Cock like a Pro

Sucking dick is a skill. If you’re good at sucking cock you should be proud! For me it took lots of practice to get to the point where guys will tell me it’s the best blowjob they’ve ever had.

Here’s a few tips for working those tips! 😘

Right around the head Is the most sensitive. Let your tongue work his head as you suck.

Lightly cup his balls while you blow him.

Careful to use no teeth. If you have trouble with this try covering your bottom row with your lip.

Don’t tell him you can deepthroat if you can’t! It looks easy in porn but it’s far from it! If you lie and say you can, you might throw up on his cock which kills the mood in a disgusting way.

I know you’ve probably never received a blowjob and never will, but keep in mind what he sees. I like to make eye contact, flutter my eyelashes and give him a nice view of my ass while I blow him.

At the end of the day, the more penis you have in your mouth the better cocksucker you’ll become.

Becoming a Buttslut

He’s had your mouth. Now he wants that sissy pussy.

LUBE THAT COCK

It’s a requirement if you want to make sure you feel good and won’t hurt yourself.

He’s the dominant one. He’s never walked a mile in your heels. He doesn’t know what it’s like taking dick. So if you’re inexperienced he could hurt you.

If you want to control the pace then you should start on top riding his cock. It’ll let you go at your own speed! Once you feel comfortable let him mount you doggy and go to town!

From there it’s easy! Bite down on that pillow and let him fuck you silly! When a stroke feels especially good let out a faggy little moan! That’ll tell him it felt good and he should keep fucking you like that.

If you’re anything like me you’ll love the submission just as much as the feeling of him hitting your sissy spot. Don’t just lay there stiff! Push back on is dick, moan all sorts of nasty stuff and enjoy your new sex life! 🥵

Good Girl

After he’s cum in your bum and left, you might feel that sissy shame. Before you purge your clothes and block his number, ask yourself “Did I have fun?”

If so text him the next day. If you enjoyed sex with a man, you might enjoy having a boyfriend!

I hope this post could help some anxious sissies who are exploring their sexuality during pride! I know it can be hard to be a sissy but you deserve to have a fulfilling sex life too! Love you girlies!

xoxo

Christina 💋

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