πŸ“š dressed up for a bi surprise - Part 2 of 1
Part 2
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Dressed Up For A Bi Surprise Ch 02

Dressed Up For A Bi Surprise Ch 02

by sometinesbistocingsguy
17 min read
4.5 (2700 views)
adultfiction

This is a follow up to my first story about my adventures with Mags, a deviant escort who over years led me on a kinky journey culminating in being forced to suck and fuck another guy while dressed as a schoolgirl. Although straight and not finding "normal" guys attractive, the thought of being made to play with other guys by a dominant woman is a real turn on.

The story can be read on its own, but I think the build up from part 1 makes it much better.

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"Hi - can you chat?"

The message was ominous, in 15 years, Mags had never contacted me unless I had reached out to arrange a session. After our last meeting where I'd been dressed up as a schoolgirl and fucked mercilessly by her and a crossdressed "headmaster" my brain had been in a mess. On one hand, I was still turned on and woke most mornings thinking about it as I played with my cock, but on the other, I was slightly disgusted with myself. More importantly, I was worried that the photos and videos she took would somehow get out.

"Yes" I replied as I happened to have the house to myself.

"Yes WHAT, bitch" came the immediate reply.

"Yes mistress" I quickly corrected.

"That's better. I've had a kinky request from some other clients and you're going to help me make it come true. They're 2 TVs who want to have a sissy slave join us for a special session and I've chosen you. It's Thursday evening for 3 hours from 7pm."

It had only been a few weeks since our previous encounter and it usually took a few months for me to build up horniness for a new session. Even though my partner was away on business and I was free, it wasn't floating my boat.

"Sorry. I don't think that's something I'd be into." I typed.

There was no response for a few minutes and I realised I was still staring at the 2 blue ticks willing her to respond and my other hand was rubbing my hardening cock through my jeans.

Eventually I saw her creating a response and, oh shit, not words but a picture. A picture of me, my lipstick coated lips wrapped around a cock with cum coating my lips, cheeks and eyes.

"I wasn't asking, slut. you've got 5 minutes to say yes, or..."

A new message arrived. this time it was a video. My stomach churned. it was me on my back being fucked, arms wrapped round the guy, pulling him into me with my legs, kissing him and begging him to "please...fuck...me....sir..."

"Shit, shit, shit" I thought. I hadn't realised that she'd filmed our whole session. But as I watched the 60 second clip my cock had hardened and I automatically took it out and started stroking. The video was hot. It had felt so good. I wanted to be a slut again.

"Yes mistress" I texted, well within the 5 minute window.

"Good slut. Be here at 7 sharp. Wear your black suspenders and stockings, knickers and lacy black bra. Put on red lipstick and eye liner before you get here. Even better wear a white shirt so your bra is obvious and come to the door in high heels."

I was panicking, the entrance to her flat is on a busy road and even though at this time of year it would be getting dark and the shops would be closed, it was very likely that there would be people about.

I considered begging her not to humiliate me but my hand was a blur on my raging hard on and the final text sent me over the edge.

"I know you're wanking your big, hard, sissy cock, cum now and clean it up cocksucker... and send me a picture as proof. You have 2 minutes..." accompanied by a picture of me getting rammed from behind while my head was between her legs licking her pussy.

FUUUUUCK. My cock gushed and spasmed as memories of that day flooded my mind.

As usual, as soon as I orgasmed, I lost all interest in following Mags' orders but I couldn't deny her now. I scooped up my cum with my fingers and dribbled and wiped it on my lips thinking I'd take a pic and wipe it off with some tissues when I got 1 more text.

"I've changed my mind, I know you don't like eating your spunk after you cum, so in case you try to fool me, I want a video. NOW"

Switching my phone to video and pointing it at my messy lips I tentatively stuck out my tongue and licked a small amount from my lips. It didn't taste bad so I tried again, this time getting a bit more. Finally. I used my index finger to push the rest into my mouth before sucking it clean like a tiny cock. I opened my mouth to show I'd swallowed it all, stopped the video and sent it to her.

"Good girl, now no more wanking until we meet."

Fast forward 2 days and I'm sitting in my car about 100 metres from Mags' flat. This is the closest I could get and there's a couple of guys hanging about near her door. As ordered, I'm wearing stockings, suspenders and a bra under my normal clothes but no makeup or heels just yet.

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The lipstick goes on easily in the semi darkness but the eye liner will need some more light to use the mirror. I pull down the visor and open the mirror with the light and get to work. A couple of times I think I see the guys down the street looking in my direction but put it down to paranoia. What the hell, I tell myself. It's 2 minutes to 7 and I'm going to have to walk towards them in high heels that I'm not used to so let's go.

I slide on the heels and get out of the truck, lock it and walk to the kerb. I can see one of them pointing and laughing. My heart is in my mouth and my cheeks burn with shame as I walk towards the door and ring the intercom bang on 7.

"Fucking faggot!" I hear and 2 of the guys are laughing, but one is just staring at me as the buzzer goes and I quickly escape into the stairwell.

The relief almost overwhelms me as the door closes and I walk to the first floor hearing the familiar click of her door opening. As I walk through and give Mags a quick peck on the cheek I hear voices from her bedroom and remember why I'm here and my comfort evaporates in a second as I look at my Mistress...

"Jeans, shirt and high heels off" she commands. But even though she is telling me what to do there's something different in her demeanour tonight and she's dressed very girly... in the schoolgirl outfit I wore last time.

"Do what you're told and you'll be OK" she whispered in my ear "They don't want want you to be feminine, they want to control, humiliate and fuck a straight sissy. I'm sorry...."

Mags' bedroom door opened and there stood my horror - and my fantasy. 6 feet 2" of drag queen. High boots. Stockings. Corset. Make up. Brunette wig. And a massive cock. Soft, but still a weapon.

My mouth dropped open in surprise. I'd seen this "woman" in a bar in town one night when I'd been out with my friends. She was sassy and brash and obviously male and had been with a hot blonde TV who was much more feminine. I'd speculated many times since what their relationship was and if they played together. Of course, I joined in with the lads banter about them being "fucking fags" at the time.... Now i had the words burning in my ears from the guys outside....

I hoped I would be blindfolded and tied so I could get off on being forced, but not this time. Without a word I was marched into the bedroom and pushed down onto my knees. My brain was lagging about 20 seconds behind reality and I eventually noticed that the feminine "girl" from the bar was there dressed as insanely horny woman, similar dress and makeup but obviously the 6' 2" Goddess was in control.

Both their cocks were at my eye level and Goddess grabbed the back of my head and pulled my face onto her semi hard cock.

"We can get to know each other later, now we're going to fuck. You'll do what we want, there's 2 of us and we'll take what we need. Do you understand?"

She was grinding her hardening cock into my face and I could hear the other "girl" panting, not like a women, like a horny guy, and the noise of bare skin on bare skin as she stroked her hard cock.

There was no messing around tonight. My hand went round the base of that magnificent shaft and my tongue slurped up one side, back to the base, up the other side and briefly over his mushroom and back to the base. I was rising and falling on my knees letting plenty of spit coat the veiny shaft. After a few minutes my hands were grabbed and placed on 2 more cocks, one real and one Mags' strapon. Goddesses cock rested for a few seconds on my lips, Two hands held each of my wrists and the monster was thrust into my waiting mouth.

I tried, I REALLY tried to back off a bit but it kept coming for my throat.

"SUCK IT BITCH" she shouted and slapped my face as it pushed into my throat. I was gagging. I was trying to get away. I tried to scream. My arms were pulled behind my back. Goddess put both hands on the back of my head and...

THRUST....THRUST....THRUST....

My brain was in turmoil. I'd only been through the door a few minutes and had gone from relief to being brutally face fucked. I needed time. I needed to breath. I needed to talk. I was out of luck.

"Fuck struggling against this bitch" Goddess pulled out my throat, "Let's get him tied up".

I was literally picked up and my overworked brain clocked what I can only describe as a bondage horse. Like a gymnastics horse, but with restraints.

I was bent over it before I knew what was happening and first my wrists, then my ankles were strapped to the legs, my arse and mouth at their mercy.

"Mags, you've got about 30 seconds to get him ready and I'm fucking that arse whether he likes it or not", panted Goddess.

Same drill, hands on back of my head. Massive cock slapping my face a few times. Then FUCK...FUCK...FUCK... into my throat. I hadn't even thought to scream until I was gagging again and I felt a glob of cold gel being squirted on my ass. It contracted at the feel but a finger roughly rammed straight up my ass and I screamed onto Goddesses cock.

"For fuck sake. I want him tight." she snapped. She pulled out. She walked behind me. Something huge replaced the finger.

"Please no. I don't want to do this. No. Nooo. Noooooooo."

Mags quickly put a ball gag in my mouth and strapped it tightly behind my head. I've never felt so vulnerable in my life, spreadeagled, bound, gagged and at the mercy of 3 cocks

"Give me that whip" Goddess snarled and seconds later OW... OW....OWWWWW as she went to town on my ass. I strained at my bonds trting to get away but as I squirmed the monster cock began it's journey into my bowels.

I was genuinely starting to panic. I was humiliated. I wanted to stop. That cock fucked me, going deeper every thrust. Balls deep. Pain. Being whipped. Ass cheeks burning, Ass stretching. Oh my God.....

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"I love it when they struggle like this, Im going to fuck this cunt whether he likes it or not" Goddess told the room. Dropping the whip she grabbed my garter belt and THRUST, she drove her cock in another few inches, a pause then. THRUST, another few inches, another pause, hands tightened further on my garters and FUUUUUCK...

My world went grey as that hard cock buried itself balls deep in my ass. Every nerve ending was screaming that it was too big, too long, too big, too wide, but all I could do was drop my head and scream into my gag as my ass was filled with a huge, pulsing member.

I was struggling, arching my back, pulling against the restraints begging "NO", "STOP" and screaming as Goddess mercilessly bottomed out. The only noise that came out round the gag was a muffled "MMMPPHHH" as he grabbed my hips and started to TRULY fuck me.

I got a glimpse of Mags on her knees on the bed, arms held behind her back as the seemingly submissive and demure blonde took control, her impressive cock disappearing into her cunt. My eyes took in the stockings, the suspenders, the corset and did a dance around the masculine cock and feminine lingerie. My eyes were watering as the massive girth in my ass slowly, slowly pulled out until the head was only just in my ass. I felt the relief of emptiness and relaxed. Bad idea...

",..................." I silently screamed into the gag as I was impaled roughly once again. Balls deep, too big, too long, too big, too wide,

Once more the slow journey out, Relax, breathe.

'...................." as she drove into me harder than before. Tears streamed down my face as she held herself deep for a few seconds before the slow withdrawal.

Relax, breathe....

"................." it feels like my ass is gaping as I'm full once again.

Relax....

Not this time. No respite, no breathe, just a fast journey back into my bowels. I wait for the hold, but none comes, straight out, straight in. Again. Again. And again.

Every part of my body is tense as I pull on my bindings and scream into the gag, over and over. Everything that is. except my ass. It's being pounded into submission, there's no time for it to contract. After a few minutes the pain is dull and all I feel is fullness and friction. I can't take any more, but I can't make it stop.

Her deep breathing, her hands roughly pulling my hips, the slap of her thighs as she bottoms out, the brief moments of nylon on nylon, the indescribable feeling of my ass gaping begin to take over. I'm coming back from the edge and I've submitted.

Just as I start to think I've got this and push back....

SMACK...SMACK....SMACK....FUCK....FUCK...FUCK....FUCK....FUCK....

"Don't you dare fucking enjoy this" Goddess screams as she spanks me on one cheek then the other as she arches her back and goes even deeper and faster than before.

She clicks her fingers and Blonde gurl takes her condom covered cock out of Mags. Ripping it off, she takes out my gag and before I can say anything or beg for mercy her delightfully curved cock rams between my lips.

Shit. Did I just think "delightful".

Fortunately she's more considerate than Goddess and doesn't fuck my throat but instead leaves about a third of her cock in my mouth while she quickly strokes the rest. My feelings of gratefulness don't last long as Goddess really goes to town on me, fucking my ass as fast as she can. the obscene sound of her thighs on mine, her balls slapping into mine, her nylon covered legs rubbing against mine.

I think Blonde gurl is about to cum in my mouth and I find it in me to clamp my ass on Goddess. She drives deep inside me and fucks me really hard and fast and I feel warm cum shooting into my waiting ass.

Blonde gurl holds my head on her cock as Goddess pulses inside me, all pretense at femininity gone as "she" grunts and growls through "her" orgasm.

Once again I'm pulling at my bonds to get away. The way this feels, there's no condom on the cock in my ass. I can't believe this is happening and once again go into mental melt down as she collapses on top of me, making small circular motions with her hips as she bites my earlobe and growls in that way men have.

They pull out at the same time. My ass feels empty for a moment before I feel the gush of cum pour out, running down my legs and into my stocking tops. I open my mouth to protest but Mags is waiting, Mags is always waiting, and that damned ball gag goes back in my mouth as Blonde gurl's cock head starts a journey round my gaping ass, scooping up the cum. Depositing it on my raw hole. Running from my stocking tops up to my balls. More cum back on my ass. Oh my God....

That cock. The one with the delightful upward curve. That cock just took a small thrust in my ass. Again and again it runs through the cum coating my ass and thighs and pushing it into my waiting hole.

Despite everything, it feels sensuous and caring compared to the ravishing that went before and I start to moan as she keeps her cock in me more and more.

I look to the side and Mags is cleaning Goddesses softening cock with some baby wipes, but it's not softening that much. they sit back against the headboard of the bed, stockinged legs intertwined as Mags runs a vibrator over her wet cunt while Goddess strokes her cock.

Blonde Gurls cock is now fully inside me. I feel so slutty with my wet ass full of cock and cum. and she leans over me nibbling on my earlobe, stockinged legs rubbing stockinged legs, her satin corset against my back. I don't need the gag anymore as she fucks me slow and deep as I'm moaning "please more, please more". But nobody can hear me.

The noise of Mags buzzing vibrator, the heavy slap of fist on Goddesses massive cock and the squelch of my ass getting fucked has me hard and my cock is being pressed into the bench, the steady friction taking me close to orgasm. Blonde Gurl suddenly holds still and I know what's about to happen as I feel her cock swell. She makes tiny strokes deep in my ass and seconds later I feel the warm spurt of more cum deep inside me.

"Good slut" she eventually sighs as she flops out of me and gives me what feels like a friendly slap on the arse but as I recover, Goddess is hard again and I steal a look at the clock. I've been here 15 minutes and there's still over 2 and a half hours to go. My brutalised ass leaks creamy sperm as Mags gets out a leather flogger and one of her biggest strapons. I whimper as she gets off the bed and raises her arm to strike with all her might.....

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