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Amateur

I’m a sissy slut with natural boobs and a high-pitched voice. I come from a conservative country where sex was taboo and same sex even more so. So I continue to remain in the closet, chickening out of any encounters because it could mean losing my reputation, my career, everything.

But online is where I can be female without inhibitions as long as I browse incognito and remember to log out when done. I masquerade as a woman on sites where sexually repressed men from my country seek release of their frustrations. I know it’s not ethical, but there’re not many takers for a crossdressing sissy who wants to be treated as a woman and a slutty one at that.

I don a female persona, but otherwise I try to be as authentic as I can be. So I tell them straight off that I’m old, heavy and repressed. Amazingly, I still find plenty of takers.

They usually get attracted to me by provocative statements I make on bulletin boards and seek me out on chat. I had put out my secret fantasy: “Having my boobs sucked by two guys while I play with their dicks. And that’s just the beginning.” MR responded to it. “If you ever wish to have dirty role play chat about you and two men I can definitely help you.”

And that’s how we started chatting.

Me: Wow…great

MR: Yesss

MR: I take it you don’t live in the US?

Me: No

Me: India

MR: It’s ok- we just have to time our chats right

Me: Ok

MR: But we will definitely explore any fantasy you have.

Me: Mmmmm

MR: And we can be as nasty and taboo as you wish

Me: Wow

MR: Nothing is off limits.

MR: your age?

MR: Truthfully

Me: 52

MR: Ohh my- I’m 55

Me: Great

MR: Tall white slender athletic build- brown hair

Me: I’m the opposite

MR: Explain

MR: Or if you want send a pic- doesn’t have to be nude

Me: Short and heavy, brown with greying hair

He sent me a pic of his, tanning on the beach.

MR: Me

Me: Handsome

MR: Thank you!

MR: Juhi-will you send a picture?

I was expecting this request the moment he sent his pic. A lot of guys are wary about chatting with anonymous women, figuring they could be sissies like me looking for cock. Usually, I fob them off, saying I would like to preserve my privacy. It works for some time. The problem is, I don’t look around for a quick online fuck.

What satisfies me is a long-term online relationship where men gradually discover the woman I am – sometimes I spill my fantasies out to them, sometimes I act coy, sometimes I chat about mundane things unrelated to sex, sometimes I wait for them to spice it up, sometimes I spice it up for them. In such long-term relationships, you can fob them off about a pic for some time, but as they begin desiring you more and more, there is no way you can keep doing it forever.

Luckily, I know someone who’s my age, has my heavy build, looks unsexy, and looks and feels like the repressed woman I am that’s waiting to explode out her sexuality. I share her pic with them. Yeah, not ethical, I know, but a sissy’s gotta do what a sissy’s gotta do.

When MR asked for a pic, I didn’t want to fob him off. I was liking where this could take me, and so I shared my friend’s pic with him.

MR: Yes you are beautiful

MR: And your sexual experience?

Me: Thx

I had to log out at that time. I had to get ready and go to work, and at work, it wasn’t safe for me to be chatting with men. You never know when they will send you a dick pic. It must be pretty late in the night for him too. He might have waited for a reply, before logging out.

He pinged me in the evening, morning his time: “Good morning!” I was able to check the chat only a couple of hours later. And this was the message I found. “Juhi- do you not wish to chat?”

Here was a guy who was waiting to chat with me! But this wasn’t the right time. “I m out having dinner,” I messaged back. “Then please message when you are free,” he replied.

Later that night I messaged him: Hi

MR: Hello lovely

Me: How r u

MR: I am well and you?

Me: Same

MR swiftly got down to business: Tell me about your sexual experience.

Me: Like?

MR: What things have you tried?

I was honest with him: Blowjob, ball sucking, rimming

Me: Missionary

Ok, “missionary” wasn’t quite true. I haven’t been penetrated yet.

MR: Mmm I do enjoy rimming

Me: Boob sucking

As I said earlier, I’m heavy and chubby and have had my boobs sucked often.

MR: i should quiz you then

Me: On what

MR: So cock sucking- can you deep throat?

Me: No never tried

Me: I gag a lot

It’s true. I prefer pleasuring a cock gently. Face-fucking is not for me.

MR: This needs to be worked up to slowly

MR: been with a woman?

I’ve been with a woman, but never as a sissy. So, “No,” I replied.

MR: Okay- rimming do you enjoy it? Receiving AND giving?

I’m a sissy, I’ve only given, I tell him

MR: Anal?

Me: No

MR: And only missionary with one man?

“Two,” I said. (I’ve been physical with one man and two women, actually.)

MR: But not at the same time?

Me: No

MR: Married?

Me: ısparta escort Ya

MR: And your husband?

Me: What about him

MR Does he not pleasure you?

Me: No, he is much older

Me: He cannot do it any more

I am married, but of course my husband is fictitious. I’ve made up this story of a sexless marriage with someone eleven years older than me to explain my lack of sex.

MR: Oh I see- and so you wish to chat with someone to explore your fantasies?

Me: Ya

MR: Are you open to new ideas?

Me: I think so

MR: Very good. As we chat you must participate- tell me what you are thinking and feeling

“I want to be a submissive slut,” I blurted out

MR: Ahh yes you will learn.

MR: Will you be touching yourself as we chat?

Me: Ya

Me: Nipples are hard and boobs are heavy

It was true. I was quite excited about where this was heading.

MR: Ready to begin? We will explore your desire for two men

Me: Ok

MR: as we chat your pussy will definitely become wet

My little sissy cock was already hard.

MR: i invite you for dinner and drinks. What would you wear?

Me: A sexy black dress

MR: After dinner and much flirting we go to have a drink. As we are there a friend of mine joins us

Me: Mmmmm

MR: he is a handsome American as well

MR: We are all chatting and enjoying ourselves as the bar announced closing time

Me: Hmmm

MR: Where should we go my friend asks?

MR: Juhi where would you like to go? We can drink some more.

Me: I don’t mind anywhere

MR: We will go to my place I announce. As we drive I rest my hand on your thigh

MR: The friend is in his own vehicle

Me: Mmmmmm

MR: Squeezing-

Me: Mmmmm

MR: we arrive at my place- we all go in and I make us drinks. We sit in the sofa you in the middle

Me: Hmmm

MR: We seem to be getting a little tipsy.

MR: My friend puts his arm around your shoulders, my hand on your thigh.

MR: your lady friend is quite beautiful he tells me. I smile in agreement

MR: Juhi- do you like my friend?

Me: Yes I do

MR: I tell him- Juhi is a submissive slut. She will do as I tell her. Isn’t that right Juhi?

I have only once before had an online chat with a dom. But I had read a lot of master-slave fiction and I knew I had to call him Sir.

Me: Yes sir

MR: Give him a kiss Juhi!

Where did he want me to kiss him? On the cheek? On the lips? On the tip of his cock? I thought I had better seek a clarification lest I be accused of disobeying.

Me: Where sir

MR: On his lips. Show him how masterful you are

Me: Yes sir

MR: He leans forward- what do you do?

Again I felt the need to clarify. Was I just supposed to peck him? Or give him an intense experience?

Me: Shall I also use my tongue sir

MR: I brush your cheek- yes of course- kiss him like you kiss me

Me: I slip my tongue in his mouth

MR: Mmmm

MR: my hand sliding up inside your dress

Me: And feel his tongue with it

MR: Up your thigh

As a submissive slut, I decide I am not going to take control of this roleplay at all. I will just follow the instructions given and won’t say anything unless I’m ordered to say.

Me: Mmmm

MR: As you kiss my friend I tell him although you are a very good slut, you have never been with two men at once and experienced the pleasure of two cocks

Me: That is correct sir

MR: My friends hand now on your breast

MR: Explain to him why you wish to experience two cocks

Me: Mmmmmm

MR: My hand now finding your panties under your dress

Me: I want to be a submissive slut sir

Me :And fulfill all your wants

MR: He looks at me- I tell him she will learn today how to be a good cumwhore.

MR: Mmm he moans-

Me: Mmmm

MR: Keep kissing him dear

Me: Yes sir

Me: I let him suck on my lips

MR: you instinctively spread your thighs apart as my fingers caress your pussy through your panties

Me: And invite his tongue into my mouth

MR: I reach up and undo the zipper on the back of your dress.

Me: And I suck upon it like it was his dick

MR: instantly his hand slides in fondling you

Me: Mmmmm

MR: Pull your dress up I tell you

Me: Yes sir

MR: His rough fingers finding your nipple- pinching it softly at first, then harder

Me: Mmmmm

MR: I help you pull off your dress- you are now only in your panties

Me: Hmmmm

MR: My hand finds your other nipple and we both squeeze and pull hard

Me: Mmmmmmm

MR: Does she enjoy pain my friend asks. She does to some extent

Me: Yes I do sir especially on my nipples

MR: He has now unzipped his pants as have I and our cocks lay out for you to see

Me: Mmmmm

MR: Stroke us both I tell you

Me: Yes sir

Me: I hold your cocks in each hand

MR: Mmmm good girl

Me: And sensuously stroke them

MR: We continue to pull and pinch your nipples- stretching them out

Me: Mmmmmm

MR: My friend slaps your nipple with his fingers

Me: Aaah

MR: Juhi- kadirli escort it is time to suck his manhood I tell you

Me: Yes sir

MR: Please remove your panties first

Me: Yes sir

MR: then lay across the couch and pleasure him

Me: Yes sir

Me: I get down on my knees

Me: And lick him on the cockhead

Me: I slurp his delicious cock

MR: Yesss he moans- his large cock throbbing in front of you

Me: And I run down my tongue along his shaft till I reach the balls

Me: I open my mouth wide and swallow both his balls

MR: Oh she is skilled he tells me

MR: show him how nasty you are

Me: yes sir

Me: I lick him below his balls and make my way to his asshole

MR:He looks surprised at first

Me: I lick it from top to bottom many times

MR: Please allow her to work her magic

Me: I suck and lick his balls and asshole in turns

MR: Tongue his asshole deep. I push your face into his ass

Me: Yes sir

Me: I push my tongue into his hole

Me: And feel his insides

Me: Trying to go in as deep as I can

MR: How does it taste Juhi?

Me: Very sweet sir

MR: I kneel behind you, my fingers caressing your pussy

Me: Mmmmm

MR: My friend places his hand on your head

MR: I told you she is a good slut

Me: Mmmmm

MR: My middle and ring finger ease into your wet pussy

Me: Mmmmmm

MR: Try and see if you can take his whole cock I tell you.

MR: I tell my friend you are learning how to deep throat

Me: Yes sir

Me: I bring my mouth to his cock and take it in

I had never deep-throated a cock before. To make it authentic, I summoned all my experience of gagging during my initial days of cock-sucking.

Me: I try and let it go deeper and deeper in my mouth

Me: I gag a bit but I take a deep breath and feel better

MR: You should help her I tell him- his hands now on your head

Me: I go down and down fighting my gag reflex and go down till I feel the hair on his balls on my lips

MR: His hands pushing your head down holding it in place

Me: I am out of breath but his grip stops me from pulling away

MR: forcing you to gag on the cock head rudely pushing past your tonsils

Me: And I can feel his cock in the back of my throat

MR: He grins- I can feel her throat gagging on my head

Me: I feel like I am his slut and I belong to him

MR: He releases your head

MR: you belong to both of us now

Me: And he free to do as he pleases with me

Me: I will do whatever he says

MR: You lift your head gagging- thick spit running from your mouth

Me: Mmmmm

MR: I lift your hips up my mouth going to your asshole

MR: He forces your mouth back down his shaft

Me: Mmmm

Me: Yes sir

MR: My tongue penetrated inside you

Me: Mmmmmm

MR: His hands lifting and lowering your head on his shaft.

MR: I take my place behind you my cock in your pussy now

Me: Mmmmmm

Me: Gag me again sir

MR: She’s learning to take cock well. We time our efforts- as I slam my cock into your cunt it pushes your mouth down around his shaft. He holds your head- his head now into your throat

MR: Filthy slut he moans

Me: Mmmmmm

MR: He holds you in place as I pound your pussy from behind

MR: his hands holding your head only using the back of your throat for his pleasure

MR: Would you like to sample her pussy I ask him

At this point, I get a bit worried. It is way past midnight where I am and I have an early shift at work the next day. I don’t see any way of getting out of this situation, and I do something I should never do. I log off without permission.

I realise I had committed an unpardonable sin. And as a good sissy slave, I decided to take my punishment for this lapse. I messaged him the next morning: “I am sorry sir. I dozed off as I was sleepy. Please punish me accordingly”

He made me wait a few hours for his reply. I wasn’t sure if he would speak to me again.

MR: Very well then. My friend stands behind you and bends you over at the waist- he raps his member deep inside your waiting cunt. At the same time I grab your hair and turn your head up

MR: my hand now on your throat- my other hand slapping each of your tits

MR: Is this what you like bitch?

Me: I accept my punishment sir

Me: Please forgive me

MR: I slap each one of your nipples

Me: Aaaah

MR: I’ll forgive you when I have satisfied my sadistic cravings

MR: My hand slaps your cheek

Me:You can do as you please with me sir

MR: Then harder and harder slapping each nipple watching each turn red and swell

MR: Your pain will be my pleasure

Me: Please forgive me sir

MR: My face in yours- squeezing your throat- tell me what kind of whore you are

Me: I am a pitiful whore sir

MR: I tell my friend show her no mercy- I then grab your head pulling it to my cock

Me: Punish me sir

MR: he slaps your ass causing you to shriek- at that moment I shove my member in your mouth roughly

Me: Use me as your fuck toy sir

MR: kadıköy escort Taking long strokes I fuck your mouth

Me: I thank you sir for the punishment

MR: Pushing along your tongue- deeper and deeper- then past your tonsils into your throat

MR: yes you should appreciate how your body is being used

MR: Holding your head still I fuck your mouth roughly

Me: Treat me like a whore sir

MR: Using your throat like a pussy

He sends me a gif of a woman with saggy tits getting face-fucked.

Me: Yes sir

MR: My friend railing your pussy- teasing you. Oh little slut- when was the last time you came on a cock?

Me: Fuck my throat sir

MR: Not caring if you are gagging

MR: Filthy bitch-

Me: I submit to you sir

MR: I pull out as does my friend

MR:we switch places- his cock now in your throat

Me: Yes sir

MR: however you feel my finger pressing into your asshole

MR: Pressing deeper

MR: opening you up

MR: Spitting in your hole getting it nice and slick

MR: fingering your ass

Me: take my virgin ass sir

MR: Yesss- I remove my finger and insert a second

MR: My friend fucking your face gently

Me: Mmmmmm

MR: I reach under you and gather your pussy juice coating my cock with it

Me: Hmmm

MR: Muffle her I tell my friend. He pushes his cock in your throat as far as he can and holds it there. At the same time I press my cockhead to your anus. Muffle her scream

Me: Ahhhhhhh

MR: while he holds his cock down your throat I push in your tight hole

Me: Umhhhhhh

MR: deeper and deeper. You try to scream but no sound comes out- I feel her scream on my cock!

Me: Ahhhhh

MR: I push until I am firmly seated inside your bowels

Me: Use me sir

MR: I then retract and begin fucking your once virgin anal as he fucks your mouth

Me: Mmmmmm

MR: move your ass whore I tell you. Impale yourself on our fuck sticks

Me: Fill me up with ur cum kind sirs

MR: I move your body back and forth

MR: then we hold still as you fuck your own mouth and ass

MR: you will get our cum when we allow it

Me: Mmmmmmm

Me: Yes sir

MR: I slap your ass

MR: hard

Me: Ahhhhh

MR: Hey you should try this tight shithole I tell my friend

Me: Hmmmm

MR: We withdraw and he sits in the sofa reclining back. He pulls you down on top facing away- aiming his cock at your asshole. Take it slut I tell you

Me: Yes sir

MR: Take his cock in your ass

Me: Taking it all in

MR: He pulls you back and waits for you to ride his length

Me: What about your cock sir

MR:i say wait- and go to my room, bringing back lube

Me: I grind my ass on his cock

MR: my cock will also find a home.

MR: I squirt lube on your pussy. It runs down coating your anal and his shaft

Me: Taking in his entire length

MR: pushing your thighs back I position myself between your thighs- my cock pressing your pussy opening

MR: With a push I penetrate you

MR: Moan for us slut

Me: Mmmmmmm

Me: Use me sirs

MR:Tell me it feels being filled with a cock in your pussy and ass?

Me: My body is for your pleasure

MR: Cum on our cocks

I have a cock each up my pussy (if I had one) and ass, but I feel like having more.

Me: I would like a third one as well sirs

MR: We both piston in and out

MR: oh you would?

Me: Yes sir

MR: I text my friend who lives nearby

MR: within minutes he arrives- I tell him the slut wants a good gangbang

Me: Hmmmm

MR: he strips and tells you to suck his cock

Me: Mmmmmm

MR: Mmm what a filthy whore you are

He sends me another gif of a slender girl getting pounded in all three holes.

MR: This is what you desire cumslut?

Me: Oh yes sir

Me:All my holes filled up by you and ur friends

MR: My new friend slaps your nipples hard

Me: Mmmmmm

MR: I say switch. The second friend lays down and you mount him in your pussy

MR: Facing him

Me: Yes sir

MR: the first fucking your face

MR: i insert my cock in your ass again

MR: pummeling you

Me: Thank you sir

MR: Your moans are groans filling the room

Me: It is my pleasure to serve you

MR: Is it enough for you or shall we use in in deeper more sadistic ways?

I could have gone on and on but I need to get ready and go to work.

Me: It is enough for the moment sir

This time I know better to seek permission.

Me: I request your permission to leave and perform my other chores

MR: Very well- your pussy mouth and anus being assaulted

Me: Thank you sirs

MR: permision granted. We will finish tomorrow- right now though send me a picture of your wet pussy

Me: I hope I provided you with pleasure

MR: And you have been pleasured?

Me: Yes sir

Me: It was the best roleplay of my life sir

I had cum twice through the entire chat, rubbing my cock with my fingers as if it was a clit.

MR: Show me your wet pussy now slave

MR:We will definitely have more

That was a bummer! How could I send him a wet pussy pic when I didn’t have a pussy. Sure, I could send him someone else’s pussy like I sent him someone else’s face. But I feared I would get caught out, and lose the dom that I had found. If I didn’t obey, I would lose him too. There was only one way out, I had to confess.

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