Never waste cum - even if you missed it the first time!

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Today's Document

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YOU ARE THE REASON
Sade Olutola

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@charlenamariekc
Never waste cum - even if you missed it the first time!
I re blog it every time
Yes i do…
Omg yes, especially together, during a hot sexy MMF 3sum with my beautiful sexy wife and our hot bi CD boyfriend mmmm 🔥 af … 💜💋
I love her hair.
And then you’ll eat his cum out of my fucked pussy and suck his cock clean
Ohh yess thank you baby
I would love doing that for you baby
Best position
Definitely the best cuck position
How about I luck your clit while he's fucking your pussy?
I prefer "sexually confident and adventurous" but, yes. 😈
I love a sexy woman who is a slut. Some of us though, want to be as filthy as they are.
Here is another very old and very short erotic story of mine:
It Kneels to Reason, Sissy by Meganprincess (2021):
That's right, sweetheart. The time has passed for your little excuses. It just stands to reason or maybe it kneels to reason?
Remember what you told me that first night when I caught you wearing a pair of my panties under your pajamas in bed? You had just moved in with me. You blushed a bit then you claimed the panties were just more comfortable than your regular underwear. Softer on your rough skin and so on. I laughed inwardly and used my little pinkie to trail along your tiny penis until it grew hard in the pink satin. I wasn't really surprised to find out that you were an effeminate sissy wimp. My girlfriends tried to warn me but I thought you were sweet. You're sweet alright lol. And so I encouraged you to shave your legs since it would make you 'more comfortable'. Stockings and pantyhose came so naturally to you as did your increasingly subservient position to me. You put up no fight when I painted your toenails and had you walk in your first pair of high heels. It was funny asking you if they were 'more comfortable' than your boring loafers. I sent pics to my girlfriends. Then I began slipping you hormones and allowing you only to masturbate - first only to me and on my shoes, then to femdom porn and in your hand, then only to gay porn with strict instructions to lick and swallow the cum from your hand. Oh, you fought me on the gay porn at first but it was easy to convince you to just 'play along' for me as I batted my eyelashes and stroked your legs in your nighty. When your little nubs began to grow, your nipples were super itchy and puffy, so I left a little soft pink nylon training bra out for you. You began wearing it, of course, and I added more and more feminine clothes until I had you living as my sweet girl 24/7. As your hair grew, I hinted that I should take you to a salon to have it styled but you cried and begged not to be taken outside as woman. Such an emotional little sissygirl with the increased doses of hormones raging through your system! On the pretense of saving you from being so emotional and fragile, I convinced you to lock yourself up in a little pink cage for me. Snatching the key, I let you know that there would be no more jacking off at all. That's for boys. And you are not that.
That brings us to last night. Look at the pic I took of you, panty pansy. Aww. It was so sweet to see you reach your breaking point. The point at which, after deliciously teasing you with my sexy outfits around the house and my soft caresses to your cage for a month, you began to beg. I acted like I didn't hear or understand: "What is it you want? What does my sweet girl need? Tell me." And you fell to your knees in front of me and begged to be allowed out of your chastity. You were so frustrated and desperate to cum. You kissed the little key hanging on my ankle bracelet. You offered me money and jewelry. You said you would do absolutely anything to be allowed to cum. SLAM! The trap sprung and I gave you only one way to earn release which was to come out with me and suck your first dick. You balked. I laughed. You said no. I smiled and began teasing your trapped, weeping cock and bloated, heavy sissy balls with my high heels relentlessly for an hour until you agreed. I could hardly contain my joy as I sent you upstairs to get dressed. You came down, visibly conflicted, wearing exactly what I demanded: your sluttiest black high heels, sheer black stockings, black panties, and black corset top lingerie. Your makeup perfect after hours of supervised training during previous weeks. Your hair, I pulled into a high ponytail before handing you a shiny black purse hanging from a thin gold chain. A cheap purse. The kind a hooker would carry. In other words, perfect for you.
And then I explained: "If you are going to wear girl's clothes, then you're going to act like a girl and that includes making men happy with your pretty little mouth. Don't worry, sweetie. I have already arranged it with Carl. He's waiting for his new cumrag in an alley downtown. You remember your old work friend, Carl? Ya, we've, umm, 'been in touch', if you know what I mean, since you first introduced us. Anyway, don't be nervous, babydoll, I will hold your hand as you kneel on the pavement in front of him and whisper in your ear just how he likes his dick to be sucked. I'll coach you as you unzip him and softly take his cock in your wet mouth. If he cums on your face or in your mouth, then I will bring you home and let you masturbate. Or…you can just stay locked? You don't want to stay locked? Good. Where was I? Oh yeah, I just want you to know that you don't have to worry, precious; if he calls you a sissy faggot, I know you only dress like this because it's 'more comfortable', right?".
I guess the picture shows us all what your decision was. What it doesn't show is Carl coming home with us to move in. It doesn't show you being locked back in chastity and not being let out until you sucked two cocks in one night the following weekend. The next weekend it was four in a filthy gas station bathroom. The blowjob requirement was soon changed to full-on fuckdoll duties for release. Predictably, you are now on your back with your legs spread and your mouth open most days of the week in a motel room as you accept your new life. I'm just glad you are more comfortable now.
--------------------------------------
Hope this little caption and story tease made a little wet spot of precum appear at the front of your panties. Be a good girl and leave a sweet review unless you want to spanked by Meganprincess!
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 💋
intim-a-sissy part 3. the club bathroom 🪩💄
the bass from the club is vibrating through the bathroom floor.
the neon lights are buzzing.
it's just the two of you in front of the massive mirror.
the air is thick with the smell of hairspray, sweat, and expensive perfume.
you feel so small next to her. so utterly outclassed.
she turns to you, pulling a glossy fenty tube from her tiny little clutch.
she steps directly into your personal space.
"hold still, babe…" she murmurs.
her soft, manicured fingers gently grab your chin, tilting your head up.
the intimacy of it makes your knees go weak. you're completely frozen.
she carefully swipes the sticky, sweet-tasting gloss across your bottom lip, then your top.
she presses her thumb to the corner of your mouth to clean the edge.
she steps back to admire her work.
but her eyes trail down. past your chest. down to the waistband of your jeans.
you bent over earlier, and you know exactly what is showing.
the delicate, scalloped edge of your pink lace thong.
she doesn't gasp. she doesn't laugh.
she just smiles this warm, totally accepting little smile.
"omg… wait…" she purrs, leaning her hip against the sink.
"those panties are sooo fucking cute on you btw…"
your male ego completely flatlines.
"liiiike, where did you even get them? the lace is giving pure angel energy… they look sooo tiny, do they even hold your little situation in?"
she winks at you.
she sees the sissy lingerie. and she thinks it's cute.
you are officially one of her girlfriends.
it's giving… bathroom touch-ups, exposed lace, permanent girlie pop. 💋🪞
BIGGER NEW LIST OF SEX QUESTIONS
This is a mix of all the best questions I’ve come across on here, with a few new ones suggested by my mutuals.
They’re are all in a random order so you won’t know which ones are being asked…
And they’re meant to gender neutral and for all ranges of experiences! (Let me know if any aren’t and I can edit it)
—
Tag your biggest tumblr crush.
Do you eat ass? Do you like to have your ass eaten?
Have you washed your hands since you last had an orgasm?
Have you ever posted a nude to your own blog?
What’s the best orgasm you’ve had in the past few months?
Have you ever masturbated to someone you know who isn’t your partner?
What’s the soonest after meeting someone that you’ve slept with them?
What position or angle or specific technique never fails to make you cum?
When was the last time you watched porn?
What is the hottest thing someone has ever done with you in bed?
Do you prefer tongue or fingers?
Are you a top/dominant a bottom/submissive or a switch?
Have you ever had your own underwear in your mouth? Have you ever had someone else’s underwear in your mouth? Has your underwear ever been in someone else’s mouth?
What’s your go-to nude pic to send to someone. Describe the angle, lighting, body part etc.
Do you ever suck on a dildo while you masturbate?
Do you have a sideblog? Is it more or less NSFW than this one? Is it secret or can we see it?
Has anyone ever watched you masturbate live online? Have you ever watched someone masturbate live online?
Do you have anyone from Tumblr’s nudes on your phone right now?
What underwear do you have on right now?
What’s the most surprising discovery you’ve made about your own body?
Has a neighbour ever seen you naked? Did you like it?
What’s the hottest sex dream you’ve ever had?
Have you ever watched people having sex?
Are you open about your sex-life and sexuality?
Does anyone you know in real life know about this blog?
Do you have any of your own nudes on your phone right now?
When was the last time you had sex?
Have you ever masturbated to any of your friends? Do you think any of your friends have ever masturbated to you?
Describe a typical masturbation session.
How do you feel about threesomes? Have you ever had one, and if not, would you ever have one?
What’s something that turns you on, but you’re a bit embarrassed by?
What is the wildest fantasy you ever had that actually came true?
Have you ever gotten turned on at work (or while WFH)? What did you do about it?
Do you listen to audio porn?
Which one of your holes do you most want to be filled right now?
Are you loud or quiet when you masturbate?
Do you own any toys? What’s your favourite?
Have you ever confessed to someone that you got turned on by them? What about masturbated to them?
Do you have anyone else’s nudes on your phone right now?
Have you ever hooked up with a stranger or had a one-night stand?
Do you like being called a slut or whore in bed?
Have you ever been caught or walked in on while masturbating? Have you ever been caught or walked in on while fucking?
How do you feel about swinging or partner swapping? Does the idea turn you on?
Have you ever masturbated to a mutual’s selfies before? Tag them if you dare.
What’s the kinkiest thing you’ve ever asked someone to do while sexting?
Has anyone ever watched you masturbate in person? Have you ever watched someone masturbate in person?
If you had 5 mins alone to get yourself off right now, without your phone, what would you do and what would you imagine?
Have you ever sent a nude via DM here?
What’s a sex act you think is overrated? What’s a sex act you think is underrated?
When did you last have an orgasm? How did it happen?
Do you shave your pubic hair?
How often do you masturbate?
Where’s the most unusual place you’ve masturbated?
What’s the most amount of times you’ve orgasmed in a day?
Have you ever been so turned on that someone noticed?
Have you ever masturbated with someone?
Have you ever gotten cum on your clothes before? Did anyone see that shouldn’t have?
Have you showered since you last had an orgasm?
Who’s the most inappropriate person you’ve ever had a fantasy about?
Have you tasted yourself? If so, what did you think?
Have you ever masturbated to someone you know’s selfies before?
How long do you usually masturbate before you cum?
What’s the weirdest porn category you’ve ever searched for?
Are you noisy?
What are your top five favourite blogs to masturbate to? Tag them!
Describe your nipples. What colour are they? What size are they?
If you had 5 mins alone to get yourself off with porn right now, what would you type in the search bar?
What is your favourite pair of underwear like? When did you last wear them? Was it special occasion?
Are you masturbating right now?
Would you like to watch your partner have sex with another person? Would you like to have your partner watch you with another person?
Start typing out your dirtiest fantasy you can think of and don’t stop til you get so embarrassed you can’t go on any longer. Just make sure it’s actually something you’re into!
Would you ever fuck a couple?
Would you do a cum-walk?
Have you ever had an orgasm that you weren’t expecting?
What’s the messiest you’ve ever got when masturbating on your own?
Have you ever worn lingerie?
If you could fuck anyone at all right now, who would it be? Do you know them in real life? Do they know you like them?
Which mutual would you most like to fuck right now? Do they know? Tag them if you dare!
What’s the last object you put into your own body for sexual reasons?
Do you have any recurring fantasies you keep coming back to? Do you think they’ll ever happen?
Where’s the most unusual place you’ve had sex? Did you cum?
Have you ever been made to/made somebody beg for it?
What’s your dirtiest secret?
What’s the most embarrassing porn you like to watch?
Have you ever put your finger in your own ass?
Do you like slapping someone’s face? Do you like your face being slapped?
Have you ever used panties to masturbate?
Do you have sex dreams? If yes, when was the last one?
Have you ever slid into someone’s DMs? Did it work? If yes, what was your technique?
Who is the coolest person you follow here? Tag them.
What is your sexual orientation?
Have you ever fucked in public? Where was it? Did you get caught?
Do you have any piercings or tattoos?
Describe your body in a way that would turn us on.
Do you like being tied up?
What’s the kinkiest thing you’ve ever asked someone to do in real life?
What was your most shame-filled orgasm? Why?
What’s the messiest you’ve ever gotten during sex?
Admit something sexual that you’ve never told anyone else before.
Put your hand into your underwear right now and type a reply to this with your other hand. Say whatever you want, so long as you’re touching yourself as you type.
—
Rules:
Send them via anon, or not. Whatever.
If you reblog this from someone then you need to send them an ask from the list.
And of course you have to be over 18 to play.
If you enjoyed these, please follow @anonanonanonanon-again :)
I want Asks!
@forgottenwifedesires I literally want to know all of your answers
Maybe you've gone too far sissy?
Now, isn't that the whole point of becoming so feminine? To become the girl of everyone's dirty dreams?
Bucket list item
So, He Wears Feminine Things
This is addressed to the wife, partner, girlfriend or other who has just discovered that the man in your life secretly wears feminine lingerie at times. Quite how you discovered this is not important, so much as how you react to it. That in turn will depend on a number of variables including your upbringing, your faith, your education, and your expectations of your relationship.
The revelation is probably a shock and leaves you with a turmoil of feelings and questions. Is he gay? Is he having an affair. Does he not love me?
First, calm down and realize that it is unlikely to be the end of your world or the end of your relationship. Your man cross dresses, expressing a deep seated feminine side of him that you did not know about because he has endeavoured to keep it a secret from you, fearing to damage a relationship he holds as very important to him.
Interestingly, men who cross dress are far more common than one would think. It is not a perversion but an expression of something that is a part of him, something he probably realized as a teen or young man and something that he has likely been ambivalent about ever since, cycling through guilt and grudging acceptance several times over.
There is in fact a wide scale between what our culture has tended to simplify as a binary system of ‘male’ and ‘female’. Your man is a little way along that scale, to all intents and purposes a male and comfortable to be so, but with an added feminine component which our culture provides very little way for him to express. Ironically, women in our modern culture can dress either in frilly feminine clothes or very masculine clothing without comment. The same latitude is not given to men, and should they publicly wear anything that is in the slightest feminine, they are called ‘sissies’, ‘queers’ or other insulting names. Cruelly, our culture has defined ‘men’ in a very narrow and confining way.
Interestingly, our native, indigenous culture has long recognized ‘Two Spirit’ people, further recognizing that such people have value among them as those with an empathy for, respect for and understanding of both primary genders. Such people are respected, not reviled.
Is he having an affair? No, those feminine items are not souvenirs of some sordid affair. He likely bought these things, one by one, on those rare occasions that the opportunity arose. He keeps these things hidden somewhere, fearing your reaction if discovered.
Is he gay? Some cross dressers are, but most are not so inclined. However, cross dressers are often attracted to other men who cross dress, when dressed, though not to men dressed as men. There is a long term for this condition, likely odd to you.
Does he still love you? Yes. Ironically, statistics show that the majority of cross dressers in a steady relationship greatly value their relationship with their partner. This increases
their fear of damaging this relationship. Most cross dressers yearn to be better understood by their partners
The worst thing you can do is to insist your man throw away his stash of feminine clothes and promise never to even think of doing such a thing ever again. He will promise. He values you highly. He will try to keep such a promise. But he will not be able to in the long run. You will simply have driven him further into the depths of the closet.
The better alternative is to accept the situation, recognizing that this is not going to go away and that there is some wisdom in the old adage ‘if you can’t beat them, join them’. The vast majority of cross dressers are ‘sometimes’ dressers, with no wish to live full time as women.
One response could be to accept that your man needs to occasionally express his feminine side, give him specific opportunities to do so, but state that you do not wish to be directly involved. It would likely be a huge relief for him to shed the cloak of secrecy, no longer fearing your unexpected early return home and the trauma of discovery.
Another response is to take an active role. Some partners help their men when shopping for clothes, either in the store or online. Some partners enjoy secretly knowing what their man is wearing under male outer clothes while out visiting with friends or at dinner and a show. Some couples buy matching sets of underwear or nightwear and enjoy wearing them together. Some incorporate cross dressing into their sex life, role playing and enjoying sex while fully or partly dressed. The range of possible responses is wide. Outright rejection is an unwise choice and will inevitably sour or ultimately ruin your relationship.
That your man is less of a man than other men you know is a false supposition. Think of him as more than a man. The current terminology is ill defined and confusing, but think of him as a man who has a female persona beneath the surface, perhaps well hidden but yearning to be expressed.
Yes, there is a risk in opening any door into your relationship. A few cross dressing men ultimately cross a threshold and seek to live full time as women, perhaps entering new relationships with others similarly inclined. A few may even commit to surgical procedures that confirm their new gender identity.
But, this essay addresses the vast majority of men who seek ‘sometimes’ to express a feminine side of themselves that is suppressed by our western culture. They seek to be better understood, not vilified. Please give them space to be who they fully are.
PS Readers, if you can use this letter yourself or know of someone to whom this would be helpful, please feel free to repost or copy.
AmandaJane70
I'll bet you that's a nice, hot and juicy glistening of cum on her lips. So kissable.
Well sticky, well oiled, well lubricated, well jizzed, well worn, well compromised, well used and well destroyed. Life, love and lust goals.