The following week, I was back to normal, well, if being a whore for hotel guests is considered normal.
However, none of the cocks that fucked me gave me the same level of pleasure as Dan's had or the stranger's cock at the forest car park that night, which had sent me into an unbelievable orgasm.
However, I knew my role as a whore was about their pleasure and made sure all the guests were left satisfied.
I always talked to Sir and was open and honest with him, so we did discuss the subject.
"Well, it seems you crave those bigger cocks, Evelyn. Not totally unexpected, as also being such a huge pain slut, you may need that feeling of being stretched, of being full of cock, almost feeling pain as well as pleasure before you can be fully satisfied sexually," Sir told me.
After listening carefully to Sir, I replied, “Yes, Sir, I think you might be right, that pain turning to pure pleasure definitely does give me such a high.” I said this sheepishly, hoping I wasn't offending Sir.
"Well, I will just need to ensure that cunt of yours is filled full from time to time, Evelyn," he told me.
Then I changed the subject, “Sir, can I ask something?"
"Yes, what is it, Evelyn?" he could see I had a quizzical look on my face.
“It's about Dave. I know he is spending time with Mistress Fiona 24/7 as Sabrina Sir. Is it her intention to fully feminise him, like those others at that mansion last weekend?” I now asked calmly but curiously.
“I'm not really sure, Evelyn. What happens going forward will be between Mistress Fiona and Sabrina. Although I can say from chats I had with Sabrina before introducing her to Fiona, she has a very strong feminine side,” he said, although I noticed he always referred to Sabrina or her when he spoke of Dave now.
No more was said, and I settled down with Sir to spend a lovely evening together, as I knew he was going away on business tomorrow for a few days and knew I would so miss him.
When I woke up the next morning, Sir had already gone. I could see there was an envelope taped to the mirror on the dressing table.
I got out of bed and walked over to the dressing table, tearing off the envelope.
I removed a note that was inside and began reading to myself.
‘Morning, my sexy little whore. Didn't want to wake you so early.
However, get yourself ready and be at the Penthouse suite by 11.30 am. I have hung up what you are to wear in the wardrobe.
Your guest will arrive at 12 noon.
Enjoy my darling
Sir xxxx'
I looked at the clock, it was just gone 9 am, so I headed to the shower.
I was already horny, wondering what Sir had in store for me today, and the water cascading down over my body just increased this horniness in me.
However, as I was lathering my body with soapy suds, I couldn't resist the temptation to dip a couple of fingers in my hot, needy cunt.
Gently at first, but as the desire and need to cum flowed through my whole body, I was plunging three fingers deep and hard in and out of my cunt.
I could feel my orgasm build and build until my body shook as I cum hard, squirting my juices all over the shower basin.
I leaned against the shower wall until I recovered from my orgasm and was able to stand, and then finished showering and dried myself off in the bedroom.
Once fully dried, I then opened the wardrobe and took out the clothes hanging up for me to wear today.
There was a red corset, red suspender belt, red stockings with a thin black back seam, a very short, tight black skirt and black 5" high heels with ankle straps.
Once dressed, I looked at myself in the full-length mirror with my bright red nails and lipstick matching the corset.
I looked every bit the slut I had become.
After grabbing a quick bite of breakfast, just some toast, I brushed my teeth and headed out to the waiting car to take me to the hotel. My body was tingling with anticipation of what might await me today.
I reached the Penthouse suite just after 11.30 and waited patiently, although the minutes seemed to drag from now until noon.
Eventually, I heard the buzz of the lift as it came up to the suite.
I stood up, waiting as it arrived. The doors opened, my eyes now opened wide in shock, but a smile formed on my lips as the man from the car park last week stepped out, and there was also another man with him.
“Didn't I tell you she was gorgeous?” he said to his friend.
“Fuck yes, she is”, he just replied.
” Hi, Evelyn, I'm Bill. I didn’t introduce myself last night, and this is my friend Terry," Bill now said to me.
Then he continued, “I was surprised, but so pleased, when I got a call from your Master asking if I wanted to fuck you again”, smiling as he said this.
“I wasn’t going to turn that offer down, as there are not many women who can take my cock as you did. And when I mentioned to your Master about Terry being in the same boat, he told me to bring him along, too. So here we are,” he laughed.
My mind was now working out from what he said that Terry must be as big as he is.
“Well, let's not waste time", I said, smiling at them both, as I began tugging at Bill's belt, undoing his trousers and pulling them down to his ankles.
His large cock sprang free, which I took in my fingers before kissing the tip.
Terry began undoing his own trousers and pushing them down to his ankles too, my eyes watching him as I stroked and licked Bill's cock, feeling it get harder in my hands. I so wanted this cock in me again.
As Terry slipped his pants down, my eyes widened as his cock looked even bigger than Bill's, not by much, but definitely, maybe an inch.
Bill laughed, “I thought you'd like Terry's cock, Evelyn. He didn't believe me when I told him you had taken my cock fully"
I was mesmerised staring at Terry's cock.
“Right, get on the couch on all fours whore,” Bill now ordered me.
I stood up and walked over to the couch and knelt on it with my head over the arm.
Terry came around and, now having removed his clothes, waved his huge cock in front of my face.
I opened my mouth and flicked my tongue around the tip and head of his cock.
“Open wide slut,” Terry told me.
I felt the tip push against my lips as he slowly fed me his cock now.
I really was struggling to open my mouth wide enough to take it in my mouth, but somehow I managed as I felt the head push in fully between my red lips now.
“Oh fuck Bill, I can't remember the last time anyone took my cock like this,” Terry spoke to his friend, as he now pushed deeper in my mouth until I felt the head of his cock bump against the back of my throat.
He just held it deep in my mouth, savouring the feeling of my lips tight around his cock.
Bill spoke to him now, “I did tell you she was a wonderful, dirty whore, Terry. Just give Evelyn a minute to adjust to your cock, then fuck her mouth.” Terry just nodded.
Bill got on the couch behind me now, “Lift that ass, Evelyn.” As I did as told, raising my ass higher.
I wanted to moan out as I felt Bill insert fingers in my cunt, but with Terry's cock filling my mouth, nothing came out.
“She’s fucking soaking already, it's now time we fucked this whore.”
Having adjusted to the size of Terry’s huge cock, I was now able to begin sliding my lips up and down his cock, my lips clamped so tightly around it.
I felt Bill remove his fingers, but these were soon replaced by his big cock, which he just shoved deep in my cunt. Again, I tried to moan as I felt that cock stretch my cunt lips wide, but no sounds were able to be heard.
They then began to spit-roast me, both seeming to push deeper and deeper with each thrust. Pushing so deep that I felt that, with the size of them both, that eventually their cocks would meet in my stomach.
Bill was fucking me so hard and deep now, and I could tell he was in my cunt to the hilt as his balls began slapping against my skin.
Terry saw this: “Jesus fuck Bill, you weren't lying, she's taken you all”
This inspired them to just fuck me harder at both ends, suddenly without warning, as I was unable to speak through the cock stuffing my mouth fully, I cum, squirting my juices out around Bill's cock.
I don't know if it was because no one had managed to suck Terry's cock in a long while, but he tensed and shot what I can only describe as a torrent of cum down my throat and as he slid out, shot the final couple of strings of cum over my face.
I could now concentrate on the cock in my cunt, and as I was now able to moan out, I was begging Bill to fuck me harder and to fill my cunt with his spunk.
“Fuck what a dirty, wonderful whore”, Terry said as I felt Bill just shove his cock deep, tense and flood my cunt with his spunk.
Terry couldn't wait to replace Bill and had been stroking his cock, getting hard again easily, it seemed.
However, he took my hand, “Over here slut,” he said as he walked me over to the full-length window.
He told me to lay my hands on the window and push my ass back.
He then ran his cock over my wet, cum filled cunt before he started to push the head in.
“Fuckkkk ohhh god”, I squealed as I felt my cunt lips being stretched so wide around his cock.
But after seeing me take Bill's big cock fully, he just pushed ahead, ignoring my moans and squeals of pain.
Once he was in, though he just held it there, “Oh fuck that feels so good, so tight”, he said, which made me laugh to myself as many now say how loose it is.
He then began fucking me, my cunt lips now being pulled out with his cock.
However, it didn't take long for my moans of pain to turn to moans of pure pleasure as his huge cock was hitting places inside no one had before.
When he cum he would likely be shooting his spunk straight into my womb. Thank god I'm on the pill, I thought.
He was just ploughing in and out of my cunt now. “Anyone looking up from the building across will be able to see what a whore you are, Evelyn,” he whispered in my ear.
Such horny thoughts flooding my mind of being watched had me cumming and my juices flooding my cunt once again.
As he was pounding away at me, I gave out a loud moan as I felt his balls slap at my ass for the first time, meaning he too was fully inside my cunt now.
“Ohhhhhhhhh fuckkkkkkkk Bill, she’s taken me all, what a woman, what a whore” as he fucked me now for all he was worth, seeming to love hearing my moans of pleasure for his cock.
He finally just rammed his cock in so deep and spewed out gallons of spunk, it seemed, straight in my womb, as I had another huge orgasm. I was standing there in the window for anyone to see as my body was shaking and convulsing as I orgasmed again and again. If Terry's cock and hands weren't holding me up, I’d have just crumpled down on the floor.
Over the next couple of hours, they both fucked me in my mouth and cunt numerous times, until Terry surprised me.
“Before I go slut I need to see if you can take my cock in your ass"
I looked at Terry, “Fuck, you're not serious, are you?” I said in surprise as I was sure I'd never manage to take that massive cock in my ass.
“Oh, I'm deadly serious, Evelyn, no woman has ever managed my cock in their ass, but no other woman has enjoyed my cock in their cunt, the way you have today either." He said before, then continuing,” and I can tell you are as much a pain slut as a whore, Evelyn. So I need to see if you can take my cock in your ass. I know it won’t be easy, and it will be painful, but I think, Evelyn, that you might be the one."
The thought filled me with trepidation, no downright fear, that, as the saying goes, he definitely would split me in two and perhaps cause me real damage.
However, the whore in me saw it as a challenge, and I was here for their pleasure, not mine.
"Okay, but you will have to use lots of lube and need to stretch my hole well first," I just heard myself tell Terry.
Looking at Bill, who had a complete look of surprise on his face, I told him, “If you go to the bottom drawer of the dresser, you will find everything you might need there.”
Bill managed to break out of his daze and went to the drawer and rummaged through its contents.
He came back carrying lots of different items.
Bill then told me to bend over a small table in the room. Then, taking ropes he’d found and binding each wrist to the table legs, keeping me securely bent over with my ass in the air.
He then did the same with my ankles. I was now helpless to move and now knew no matter what reservations my mind was having, that this was going to happen.
Terry stepped up behind me, “No, no lube first, you must", I screamed out.
Terry just laughed, “Have patience whore, I'm not ready to fuck you yet,” as said as he then spanked my ass three /four times.
I then felt the cool liquid of the lube being dropped onto my ass hole, before two fingers were just shoved in my ass, making me moan out.
“The whore definitely wants this too, Bill, look her cunts wet and dripping juices already without me touching it”, Terry said.
After opening my ass with his fingers, Bill lubed up a butt plug and pushed it in my ass.
“Oh god, just shove it in, stretch my ass if I'm to have any chance of taking Terry's cock in my hole", I just shouted out.
Bill just pushed the plug in deep with one shove, “Fuckkkkkkkkkk”, I screamed out.
He kept pulling and pushing the plug in and out of my ass, stretching it more. But I knew this wouldn't be enough.
“Something bigger”, I screamed out.
“Fuck you are such a dirty whore indeed, Evelyn”, Terry said to me.
Bill just left the butt plug in my ass as he went back to the drawer to look for something bigger.
“Ahh, this should do", he mumbled to himself, walking back towards me.
It was the 10" thick, black dildo which he covered in lube, before slowly pushing and twisting as I could feel it penetrating my ass.
“Fuck fuck fuck, Jesus god so painful,” I screamed.
However, Bill just kept shoving and twisting the dildo until it was all in my ass now.
The pain was like a searing heat from being prodded by a hot poker.
Bill then began fucking my ass with the dildo, stretching it as best he could.
“I think it's time, Evelyn”, Terry just said now.
Terry then positioned himself behind me and rubbed his cock around my ass hole.
“Relax, Evelyn, I know you can do this”, he told me as he slowly began to push his large head against my hole.
Even with all the stretching, it wouldn't go in; he was too big. But Terry wasn't for giving up, just yet, applying more lube to my ass and to his cock.
This time he pushed harder and could just feel his tip spreading my hole, but even that caused me such a red hot poker type pain “FUCKKKKKKKKKKKK NO IT WON'T FIT.” I screamed even louder now.
“It's going in, Evelyn, so just relax”, Terry told me sternly now.
“Oh fucking hell”, I screamed over and over as he pushed harder, the head of his cock pushing, stretching my hole a bit wider now.
“OHHHH GODDD NOOO" the pain was worse than any beating, even that I’d experienced so far.
From the first time I’d had my ass fucked by Sir to all the spankings and whippings I’d taken, nothing had given me pain like this had.
Terry just kept pushing his cock against my ass hole through my screams in pain, until I felt the head being pushed in just a bit.
“SHITTTTTTTT JESUS CHRIST FUCKKKKKKK" just swearing and cursing as he entered my ass.
“Good girl, Evelyn, we have come this far, you want my cock in your ass, don't you?" Terry was asking me or was he telling me, I'm not sure, as my mind was just trying to deal with the excruciating pain.
“NO, YES, OH GOD I DON’T KNOW", my mind and body in complete confusion now.
Terry just pushed a bit more and more, feeding his huge cock slowly into my now wide, stretched ass. My screams of pain still filled the room.
Terry then thankfully stopped and just held his cock still in my ass, letting the pain subside a little.
Fuck the whore part of me wanted this, but my mind just kept feeling the pain and visualising my ass being a huge, open gaping hole afterwards and never closing.
Would it go back to normal? I know my cunt was now much looser, open and stretched than it was before I became a whore.
“Right whore I'm going fuck that hole of yours now, I'm sure your Master will be so proud of you when you tell him you took my cock in your ass.”
Hearing the words 'making Sir Proud' was like a switch in my mind as I just screamed out now, “Yes, yes, just fuck it, fuck my ass"
That was all Terry needed to hear as he now thrust his cock deeper and began sliding it back and forth in my gaping hole, although he was still only about half to two/thirds in me.
As he now fucked me, unlike any other time, the searing bolts of pain never left, and whilst I did get the occasional feel of pleasure, the pain was still the overriding factor.
But despite the pain, my cunt still betrayed me as I somehow cum, squirting juices onto the floor.
With my ass so tight around his cock, he wasn’t going to last that long and soon after I cum he tensed and shot his final load of spunk deep in my bowels.
“Fuckkkkkkkk sooo amazing,” Terry screamed out as his cock twitched until his balls must have now been empty.
Once he cum he just pulled out and wiped his cock over my ass cheeks.
”Fuck Evelyn, Wow, wow, wow” was all he could say.
Terry then dressed, leaving me exhausted, so sore and still tied to the table.
Both Bill and Terry thanked me for a wonderful afternoon, and now that they had found a woman who could take their big cocks even in my ass, they hoped that they could get together with me more.
I watched them then walk over to the lift to leave.
“Wait, no, aren't you going to untie me?” I shouted after them, but they just laughed and got in the lift and left me, spunk dribbling from both my ass and my cunt, now making a puddle on the floor beneath me.
