Blackmailed Sissy – How Jessie became a sissy fuck

It all began when an older gentleman 55 years old in good shape sent me a message about how he has been watching my activity on the site and watched me in a sauna once and that I’ve met him before when I did an anonymous meet where I was blindfolded waiting with door open. As I read on with a stiff cock remembering that time it disappeared as quick as it came.

There were pictures of me blindfolded sucking his cock, pictures of me bent over my dining table taking his cock and a picture of my face covered in his cum then a screenshot of my social media page he had found out who I was and that I was married.

Fuck. As anyone in this situation would be, I was angry I remember saying to him (the guy) that no pictures are to be taken, I know I’m stupid probably to either mention it or do an anon meet I’m aware of that now!! So i composed a message back angry and requesting he delete those pictures and why is he sending me this message. That’s when it happened he replied with ” I don’t think your the one barking orders here are you been a naughty boy haven’t we, imagine if your wife sore these pictures and the video I have of you!”


“I heard you enjoyed the sauna last Sunday my mate certainly enjoyed your ass of yours and with out a condom your getting a right slut! You was so adamant I had to use a condom! Shall we try your reply again then boy?” I looked in the mirror and slumped into my hands and sat on my bed, he had me where he wanted me I couldn’t do anything but ask what he wanted, I had always thought this day might happen but again didn’t expect it to. Fuck, I thought to myself what have i done. I love my wife and happy with my life so I couldn’t afford for this to come out I’d lose everything, so i replied “I’m sorry what do you want from me?”

He made me wait 2 days before he replied and all he sent was “Good boy, that’s better” another day gone by I’ve been nervous as hell waiting for my wife to shout and ask what the fuck are these. It was Friday night 4 days after the initial message. I hadn’t even been replying to the other people on the site as I was worried who knew me, that’s when his message appeared it was an address and a time, I thought I’d try my luck again and replied to him with “What’s going on, what am I doing with this information.” He said “Meet me there or I’ll send a message to your wife.” I’d been thinking about this and thought I’d call his bluff and said “No you won’t message her.”

My god do I wish I never did that – about 45 seconds had passed when my wife calls me from upstairs asking if i knew a David, I said “I’m not sure whys that?” she said “He’s just messaged me asking if I’m your wife”. My face turned white and I immediately replied to him “Okay I’m sorry ill meet you there” His reply….. “Good boy, but it won’t be just me there haha”. So that time arrived and I was walking down the street that it was on and my heart was racing I thought he would want to talk about the situation maybe I teased him too much maybe he wants money, I got to the door there was lights and music I knocked on the door.

A man answered “You must be James” he said to me,I instantly said “Why are you doing this to me?” “Not me mate, he’s the guy you wanted to talk to” he replied as I followed his finger where he was pointing a man 6ft tall slim build with his top off walked around the corner. I knew this was the guy instantly from his profile photo, just waved me into another room at the end of the corridor as I shut the door I heard a round of cheers coming from the living room I had passed. I never looked into it but this sinking feeling had hit my stomach like nothing I’ve ever felt before. The door shuts behind me as I walk in and look around the room it’s just a normal office space computer desk chair book shelf, my heart starts to slow down maybe he just wants to talk.

“Take a seat James or rather Jessie!, right thank you for coming here today I thought I was going to have to send those photos at one point and no one wants to ruins someone’s life over a bit of fun do they!” He said with a smile and a wink “Okay I understand but…” he interrupted before I could finish my sentence ” Shut up, let me cut to the chase and explain what’s going to happen here, you have arrived here on your own free will correct?” He asked me ” Well yes I…” again he stopped me mid sentence. “Perfect thank you, right now I think it’s very unfair you treating some men differently when you meet, it should be a fair game across the park, now I’m very glad I took these photos and this video” he picked up a remote and pressed play on a TV behind me.

Blackmailed Sissy,
And there it was I recognised my front door and then the door opened and I was on my knees blindfolded of which you can hear me say “Use me daddy, I consent to anything and everything you want from me from this day forward” Fuck…..I remember he wanting me to say this as it turned him on little did I know this would be a lot worse than I thought. He paused and looked at me with a smile “You see Jessie I now have on tape you consenting to anything and everything I have planned for you, so you can’t deny this it’s there in video form. Come on you didn’t really think I wouldn’t record you being such a slut, I’ve been looking for a guy like you for months”

“But that was just something you wanted for the role play” I replied “Oh how naive you are, right I’m getting side tracked strip naked Jessie and remember the consequences”

I paused and looked at him and I could tell in his eyes that he meant it, I was stuck I was now this guys personal slut. I stripped naked and put all my clothes on his desk, he immediately grabbed them all and shut them in a draw behind him and locked it. He then stood up and began to unbutton his trousers, he pulled them down and grabbed his cock from under his boxers and began to wank it in front of me, he motioned for me to suck him off, I took a big breath and walked over to him. He grabbed me by the hair and pulled my head down to his cock i parted my lips and he thrust his hard throbbing cock all the way down my throat making me gag, he holds my head in place as my eyes begin to water and my breath is taken away from me, he ever so slightly withdraws his cock this head is now at the opening of my lips and he thrusts back down again he continues this for a good 5 mins before he then starts to thrust really deep and hard and his helmet begins to swell.

Blackmailed Sissy,
I get ready to swallow his load but he withdraws and cums all over my face some lands in my hair and some over my eyes. I reach up to wipe his cum away from my face but he slaps my hand away and grabs me by the wrist, he then proceeds to grab my other wrist and pulls them behind my back and begins to tie rope around them. I start to resist and pull at his rope which only angers him and he then proceeds to tell me if i don’t let him tie my hands together he will really release the new video of me taking the face fucking that just happened which starts with me agreeing to it. I’m fucked I think to myself so with that I loosen my arms and hands and begin to be tied up with a face full of cum.

Once my arms and hands are tied and I’m completely unable to move he starts to walk back around to my front and informs me to turn around and walk out the door. “But, I have cum on my face and you have a house full, can I clean myself up first?” He laughs and tells me to move. I walk out the door and he instructs me to go out the front door as well, I was relieved that no one saw me like this. There was a van parked outside his door the side door flings open and he tells me to get in.

I’m inside the van it’s cold and dark I struggle to get comfortable I can feel the van moving but I have no idea where we are going. The cum is starting to dry on my face when the van stops suddenly and the side flings open, I’m pulled out of the van and lead into some woods I’m dragged for about 10mins to the centre of a circle of trees I couldn’t see anything but bushes and trees, I’m then instructed to lean over the tree stump in front of me, as I comply my neck is then tied to the stump and my feet are pulled apart and tied to nearby branches. I’m unable to move and in a very vulnerable position!

“These are the woods that you suspected to be used by men and women to fuck, so we are going to see how many people fuck you tonight and see if your correct. I’ve put a post out on all the sites so we will see” This made my cock twitch and he noticed “Oh slut don’t think I didn’t see your cock twitch then. We are going to make a good whore out of you yet” he said as he spanked my ass hard and started to laugh! He then proceeded to spread my cheeks apart and spat on my hole he was working his thumb into my ass when I heard a rustle in between the bushes in front of me as I lifted my head up I was in absolute horror and shock.


3 guys came out of the bushes and started to laugh when they saw me One said to his friend “Oh tonight’s going to be a good night boys” of which his friend replied “Fuck yes it will and I’m first” They walked up to me and started to unbutton there trousers, a hand had grabbed my hair and lifted my head up to the sky he then began to smile and spat on my face before saying “Oh fuck boys someone’s already cummed over this slut maybe it’s the old man fingering his pussy! Open your mouth bitch”

I began to open my mouth. I didn’t have a choice I had to do as I’m told or risk be exposed, my mouth starts to take a pounding from this man’s cock it was a nice size and thick I was enjoying sucking his cock when I felt someone pushing into my ass, I quickly pulled my mouth away and yelled “Condom!! Safe only” but my fear escalated when the man who bought me here told them “He’s my bitch, fuck him how you want he will let you…. won’t you slut?” “Yes sir” is all i could reply as the strangers bare cock is pushed into my ass until his balls are resting against mine! The man’s cock is then pushed back into my mouth and they start to seriously fuck both of my holes. The rhythm and pace is making my cock rub against the wood and start to grow

My mind runs wild I’m starting to grow to love the sense of no control and no movement I’m a fuck toy, I’ve dreamt of this for ages and it’s better than I thought possible, I begin to moan on the guys cocks and they pick up the pace. “This slut is loving my cock. Steve fuck he’s so tight I’m surprised for such a slut, shit I’m going to cum soon, and it’s going right in your asshole slut.” I’m too much engrossed in the role as a slut and just moan and nod while I deep throat this guys cock in my mouth. This is too much for him and he pushes deep in my ass and erupts his load deep inside me, pulls his cock out and replaces the one in my mouth straight from my ass.

I’ve never done that before but I was too in the moment to care I sucked his cum of every last drop, then my ass once again was filled up with another cock! This carried on for what seemed ages until all 3 guys had taken turns in my mouth and ass and all 3 filled my ass with warm cum

Blackmailed Sissy, Kraker66
I wipe my eyes from the saliva and cum covering them to see the 3 guys walking away giggling to them selves,It then dawned on me that my legs and neck was no longer tied in place I actually was free from all restraints and I hadn’t even realised. I look to my right, where the guy who bought me was and he had a video camera in his hand smiling and laughing. He had so much material on me now I knew this was going to be my role until he said to stop but when would that be? “I took your restraints off about 20 mins ago, so it made good content not being tied there but being used by 3 men! I mean it’s safe to say these woods are used for the purpose a slut” All I could do was nod. I was worn out and my throat was killing to even speak! As I began to gain some strength back in my legs and start to move a hand is pushed on the back of my head and I can hear the familiar sound of a belt being unbuckled! “Fuck Jane this hole has been used real good tonight it’s already dripping with cum” I thought to myself Jane? There’s a woman here fuck I hope I don’t know her or she recognises me! Fuck!

That’s when a softly spoken female voice is heard behind me “Yes, what a little slut. I’m jealous, wish that was me bent over that tree. How about we have our fun with him first he looks knackered, looks like you won’t need any lube. That ass is gaping.” I then felt his helmet push against my ass seeking my hole and embarrassing to say but he went straight in balls deep with a wet squelch from all the cum the last 3 guys had pumped inside me! He started to fuck me harder and harder, he then instructs me to pull my cheeks apart I look over to my right where the camera is and the guy isn’t there so I tell him “No just hurry up!”

Blackmailed Sissy, Kraker66
And then a pain so sharp it causes me to yelp hits my arse! He was behind me waiting for my response and clearly I got it wrong “Sorry” I reply and I reach back and pull my cheeks apart this is when the guy pulls his cock out all the way then slams it in, in one rough motion then back out and back in! He continues to do this and then starts wiping his cock on my cheek every time he withdraws digging out all that cum in my ass I imagined! He then fucks me faster and faster and harder, now I’m grateful his cock isn’t that big as I’ve never been fucked this quick before and I’m glad it’s not with a big cock. But my cock starts to grow and pushes against the stump I’m bent over

I then feel a hand wrapping around my cock it was soft and small I knew it had to be this lady Jane’s hand which excited me, as I’m definitely more straight than bisexual, I’m now fully erect and my ass is being pounded and she starts to wank me off, the sensation of both of these combined is really doing bits for me, then she takes my hard throbbing cock into her mouth and the warm sensation is too much for me, she must know as she deep-throats my cock and the guy in my ass pushes deep and unloads inside my ass again. That’s me! I’m cumming in this ladies mouth as stream after stream fills her mouth and throat.

I can hear her gagging as my balls contract to empty all the built up frustration and horneyness into her mouth, she tries to swallow as fast as she can but ends up coughing and taking my cock out of her mouth to gain her breath back. The guy withdraws, dips his ass covered cock into Jane’s mouth and slaps my ass. The guy that bought me here then comes round to my face slaps it and says “Fuck off then slut. I’ll be in touch” while laughing and pushes me off the stump and throwing my clothes at me.

I quickly grab them and run into the woods hoping I’m going the right way as soon as I’m out of sight I chuck my clothes on still dripping with cum and head to the light I can see. I proceed through the bushes and I’m met with my road I live on, thank fuck. I live down the other end, but it will only be a 10minute walk home, I’m walking up the street and finally to my door. Straight upstairs and in the shower, I’m washing everywhere scrubbing feeling horrified that I’ve let this happen to myself, I take the shower head off and clean inside my ass trying to get to all the cum inside me! Once I’m finished I walk into my room and load my PC up to book a STD test, it’s loaded and I’m just filling in the form when at the corner of the screen an email notification comes up from Steve Edwards, subject “Whore”, my heart sinks and I open the email.

Blackmailed Sissy, Kraker66
The main body of the email reads “I thought you might like this for your records and so you know I mean what I say” I look at the attachments 2 videos and 12 photos, I click on the first photo and yep it’s me sucking a cock with my face covered in cum, the next is me looking back as my hole is being fucked, they continue like this and then I click on the video! And there I am untied being spit-roasted in the woods. I quickly turned it off. Fuck!

One week passed by and I hadn’t received any messages or emails, I’d been going to work like normal constantly watching the door to see if he comes through, hesitant when ever my phone goes off expected another message telling me where and what to do! But nothing…..its now I start to think he’s moved on he’s had his fun with me maybe there’s another victim! I woke up to my phone buzzing it’s a call from a number I hadn’t had saved, I ignored it like I do all the numbers that I don’t recognise roll over and try to go back to sleep then a text message came through “I suggest you answer that slut” is all it read.

Then the phone rings again… I answer it but say nothing. I stay silent waiting for any response and then he starts to laugh. “You have 60 minutes to get ready, I have plans for you.” and then the phone call ends, my heart started to race and I stare in the mirror take a deep breath and begin to get ready in grey joggers and a football top just my casual wear. I’m ready within 25 mins and log on to my computer to surf the Web, I’m on for no more than 5mins when my phone goes off “Your done already, good boy I love that football top

This threw me off guard completely how did he know I was dressed and how did he know I was wearing this top! I’m panicking now has he got a camera in my room? The only camera I have is my webcam just as I close my computer down, a car horn is pressed outside I look out and there’s the same van as before waiting side door open. He beeps again. I take a deep breath and go downstairs, walk out the door and approach the van. Two masked men grab me by the neck and throw me in sliding the door shut, it’s pitch black in the van but something is placed over my head anyway. I try to remember the route it took but there were too many turns for me to know where we was heading. About 20 mins past or so I thought when the side door is opened and a beam of light hits my eyes through what now seems a black clothed hood. I can see slightly out of it I’m at a house I’ve never seen before! I’m carefully lead up the stairs to the front door. When a voice says “Ah yes the sluts arrived. Get upstairs on the left everything’s there for you” My mind is running over and over “Sorry what everything? What’s everything?”

Will I ever be free?
Publicerad av cocksucker1966
2 år sedan
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8
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Kai_Maja
great- I want more
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Peter-for-TS
till JoyceLynnTV : please do write it all down!
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Peter-for-TS
so hot and horny!!
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GREAT STORY MAKES ME HOT
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JoyceLynnTV
Yummy. I've had fantasies for something similar... maybe I should write them down and post them?
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Syon5
lovely. what's next
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Yummie
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ergernebi
Nice story. I am sure nearly every sissy have a dream like that.
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