Claires New Hire Saves Me Ch 04

☆ Note - this is not for everyone. There's probably bondage, gay sex or references to it and definitely images of extreme sex, questionable consent, outright non-consent, and blackmail and there might be verbal degradation and abuse. I know this. No need to comment if you are just going to attack the author for writing it. You kept reading it.

What does that make you?

This is a complete and utter fantasy that will never ever happen - it's the same as elves and dwarves and a faithful wife. NOT REAL. You've been warned.

I woke up tangled in something. The sheets were between my legs. My head felt stuffed with cotton. My muscles ached. My cock felt....used. There was an odd lingering taste in my mouth. I kept my eyes closed trying to avoid the headache I could feel growing from the base of my skull.

I tried to take stock of where I was and what had happened last night. There was something.....

It was then I felt the slight movement, The familiar weight of a warm body laying next to and partially on me. One leg thrown over my hips and a head on my chest. I missed waking up like this. Ana had enjoyed using me as her body pillow and I had felt so alone after she left.

I moved my leg a little and discovered that I was tangled in this girl's nightgown and not the sheets as I had originally thought. I tried to open my eyes to see who had snuck into my bed only to realize that I was blindfolded somehow. I tried to bring my hands to my face to remove the blindfold and discovered that I couldn't. What the actual fuck?

Taking stock again, I figured out that I was flat on my back, blindfolded and my hands were bound to the headboard.

Then I remembered what had happened yesterday evening. Oh, Shit. I got milked. Worse than that, I got milked by a man. Worst of all I got milked into a man's mouth. Then snowballed. And...he was kinda cute. Fuuuuck. Me and Claire really needed to talk about this blackmail bullshit. Maybe I should take my money and go somewhere else. Where no one knew me. Find a new lover. A FEMALE lover. I mean, I was a horny bastard, but I wasn't gay.

Then the girl sharing my bed moved over on top of me. I felt soft warm kisses on my chest and a tongue on my nipples, sucking and nibbling, turning them into hard pebbles. My cock was starting to respond and she kissed up my chest to my neck. Her tongue traced under my chin and across to the other side. Her warm tight body gyrated gently on my hips, massaging my cock between her thighs. I could feel her warm breath in my ear and then her soft lips on mine. I felt my cock fully hard and I bucked upwards a little, unconsciously looking for a warm wet hole to satisfy my mounting desires.

More kissing followed and then her hands traced down my sides, stopping to tease my nipples once again as she raised herself on her knees.

I could feel her pulling up her cotton nightgown while she slowly rocked on my cock. Seeing nothing, I was still envisioning a hot little thing in my mind. A sexy, curvy sexpot named Carol. She was light on my hips and her sexy movements had me desperate to get inside her.

Then she reached down and grabbed my cock. I could feel the lotion or lube as she rubbed it into my hardness. It was cool but soon warmed up and started to tingle. Oh, I liked that a lot!

Then I felt what I'd been waiting for. Her holding my cock straight up and sliding herself down, slowly onto my pole.

Damn, this little thing was tight. The tightest pussy I'd ever had, This was no free range fuckslut I had slowly posting up and down on my cock while emitting sexy little gasps and sighs. This was as close to virgin territory as any man could get.

My cock was gripped tightly in that hole as she fucked me down. She took me all the way to the base and back up and never lost her cunny's grip on my throbbing cock.

She got into a steady rhythm. Not particularly slow but not fast enough to make me cum. I felt one hand reach up to my mouth. Tracing my lips. Toying with my tongue. Pressing in and pulling out in time with her posting.

As she started to speed up slightly, she stuck two fingers deeply into my mouth and I began to suck on them.

I felt her other hand toying with the blindfold obscuring my vision and I started bucking up harder. Trying to increase the pace and fill her up with my cum. I was going to finish soon no matter what happened.

As the blindfold was removed and my eyes opened two things happened at once.

First, I saw Sweet Billy in a white cotton nightgown riding my cock with huge smile. His tongue held out of the side of his mouth, between his teeth, like a fuck drunk cockpig. His Lolita pink lipstick only slightly smeared and his tiny little cock and balls were bouncing on my abs while he rode my cock.

Second, both his hands left my face and moved down to pinch and twist my nipples as he threw his head back and increased the tempo of the railing I was giving his tight ass.

Sweet Billy never stopped his ride. Not as I screamed from the mixed pain of my nipples and the pleasure of my orgasm. He didn't even stop after my orgasm was over and shame overwhelmed me.

William Seaworth, my body man, fucked me like a cheap whore all the way through his own orgasm.

I watched with an open mouth as his semi erect little dick dribbled a large load of cum while flopping up and down, striking first my abs and then his tight hairless belly.

"Jesus Billy," was all I could manage to say. Weakly. As I watched this tiny effeminate man buck and shudder through a milked out, ruined sissygasm. He fell forward to lay fully on me breathless and warm. His hips still wiggling on me like a girl who just had the best orgasm ever. I didn't feel his dick between us. Just the sticky load of cum he forced me to fuck out of him.

All I heard from Billy was a contented "mmmmmm." A kind of low animal purring from the back of his throat.

I don't know how long we lay there. Me, in my confusion, and Sweet Billy, in his evident satisfaction. I had just about decided that while yes, that was hot as fuck in a taboo kind of way; having been forced to have gay sex wasn't really my thing. Although, he did look a lot like a girl in that gown.

"Good Morning, Sir," Sweet Billy's voice said as the small light body on top of me stretched "I decided to stay with you last night. So I could be here to wake you properly this morning."

"Billy. Why are you doing this? I'm not gay."

"Oh, I know, Sir. But I thought we truly connected last night!" William said into my neck.

"Well. I mean. Yeah, I....look Billy. It was nice. Really nice. And you're an intelligent, professional...um person. But.. uh...I've never done that with a man. I've never touched a man sexually."

"Oh, yes Ms. Claire had said that you might be resistant to new things. That's why we installed the milking bench. I just thought that...well, Sir....you kissed me quite a lot last night. I'm......terribly embarrassed Sir. I will, of course, report that our failure to arrive at a mutually beneficial arrangement is totally my fault Sir."

William slid off of me and the bed in a single movement and quickly turned away from me towards the door.

"I will return shortly to prepare Sir for the day. Please excuse me to collect myself Sir."

He sounded so pitiful. Rejected. He was going to quit and Claire would blame me. Shit.

"Sweet Billy."

"Sir?" he said as he paused, still facing the closed door.

"Who's in contol of this? Our arrangment. Our intimate friendship. Is it Claire?"

"Why you, of course, Sir. I serve, in every capacity, at your pleasure."

"No milking bench tonight. No drugs. No Mr. Sharpe driving me. William, I'm seriously NOT in a good place with all this. And it's not you. You've definitely changed me. Maybe for the better. But there IS such a thing as too much too fast."

"Yes, Sir. Of course, Sir. Again Sir, I...I'm sorry that I presumed." William said turning half to me with a downcast expression. It appeared genuine. "I will of course submit my resignation to Ms. Claire immediately upon delivering you to your office."

"Was last night what Claire instructed you to do? Seduce me? Control me?"

William turned to face me completely and exclaimed, "Absolutely NOT, Sir! I was engaged to provide you firm support and to help you recover from the tragic loss of your late wife. And yes, the milking was an explicit requirement. The um...oral....part last night and this morning's activities were entirely.....my fault."

"William," I said, with a calm I didn't feel "I appreciate you. Cleaning me up. Taking care of me. I know I'm a mess. You've definitely given me an entirely new outlook on...well life and...everything. I'm just not....gay. I think you are an attractive man. I enjoyed....you know that I enjoyed the sex. The strange, taboo, forbidden sex, Billy. But, I can't see me ever going farther than that. Not emotionally. I'm sorry. My Ana...is still a wound on my soul. I can't do more. It's not fair to her, to me or to you, if I let you hope for more from me."

"Ms. Claire told me you were a man of perfect loyalty. To your wife. To your friends and employees. I'm ashamed that I tested that loyalty, Sir."

Poor guy was about to cry. I felt bad too. I DID kiss him. Oh my God. I just fucked him. Yep. Not going to be doing that again. Well...I mean. What the hell WERE those drugs? But, I wasn't ever a cruel man. I wasn't raised to be that way and never felt the urge. I mean, as long as he and I could get back to a more normal relationship; whatever that meant. I guess as long as he didn't hold out hope of a fabulous gay wedding I could deal with it. He DID know how to give a guy a bath after all. Jeez, maybe I could get Claire to recommend a good therapist.

"William, you are my body man, if you still want the job. But you work ONLY for me going forward or the deal is off. Just a body man. I'll need to rely on the professionalism of William Seaworth to be the rock that I rebuild my life on."

William looked me in the eyes for a long minute. I felt like he weighed and measured my honesty and my soul.

In my defense, I was being honest.

William smiled and said "Well then, we will speak no more about it, Sir. I will be your man in all things. From William to Sweet Billy. I will strive to support you ably in all things. But only as Sir requires."

With that pronouncement, William turned and walked smartly out the door. Damn. He didn't untie me. Left me sticky and naked and questioning everything but at least my butler, William, was smiling. Hmmm....what a wild night. And if I was being honest with myself, Sweet Billy knew how to ride a cock like a professional cumpig! Damn. Not being gay around my own personal twink might just be as hard as being gay around the rest of the world. Sigh.

Billy and me would work it out.

Me and Claire were going to need to have a long talk, though. Soon.

~ Ch. 05 Coming Soon ~