The Assistant: The Fitting

This is a continuation and it is recommended that you read the previous parts.

After my little adventure with Emma earlier this morning I took sometime to relax and get all my energy back, as I had a feeling I was going to need it all. As I didn’t know what I should wear when I meet Amy I decided to put on jeans and shirt, so I’m casually but look smart enough to get away with it.

I am walking down the main stairs as Amy is walking out of the study to the right. When she sees me coming she stops at the bottom of the stairs and waits for me to get to her side. “Follow me John.” She leads me out the front door and to the awaiting limo, held open by the chauffeur. Thank god I’m not the only guy around here, otherwise I would be worn out in no time.

As the limo starts to pull away Amy places her hand on my leg and gently rubs it. “We’re going to get you some new clothes dear.” She tells me. “A friend of mine owns this fabulous shop and if you’re working for me you’ve got to look like the best.” Her hand continues to rub my leg, moving higher up my thigh until it finally comes to rest over my cock. “It’s a good while there, so there’s no reason why we can’t have a little fun.” She purrs, giving me a wink. She presses harder against my cock and gives it a firm squeeze. My prick responds to her touch as it begins to harden.

She gets on her knees in front of me and slowly unzips my jeans to free my rapidly swelling dick. Within a few moments she has it in her hand and is slowly stroking it, making me moan softly. “You like that?” she purrs and I only groan in response. “How about this?” she asks giving my shaft a squeeze. She begins to firmly jack me off, slowly at first, gradually picking up speed. “I think we need to talk John. You are mine do you understand me? Your cock belongs to me. I own it, and I don’t think it is right for you to go giving my things to other people. I’m talking about your little romp with Emma. Oh, I heard that all right. She’s very vocal after all. I don’t want you to give away my things ever again, understood?” she demands as she hand around my prick squeezes hard, while her other grabbed my balls hard, making give a half painful, half pleasurable gasp.

“Yes, I think you get it. However, I don’t want you to feel confined by me. So this is the deal, I’m willing to let you screw every hot pussy you want but for every time you fuck a little whore you have to fuck me and tell me all about it. Ok?” she says as she looks up at me. When I don’t respond she stops jerking my cock. “Well?”
“Yes. Whatever you want just please I’m so close.” I beg. A smile crosses her face and she resumes fisting my cock with her delicate hand. Her hand wrapped around my shaft is now almost a blur as it moves up and down. Her other hand is between her legs, down her suit trousers and in her panties, furiously frigging dripping cunt and swollen clit.

She lowers her head between my thighs and takes the head of my dick into her moist mouth, while her hand continues to fist my shaft and occasionally squeeze my balls. She is breathing heavily by now as she brings her orgasm ever closer. Suddenly she lets out a deep moan as her orgasm shakes her body. She keeps her lips sealed over my bulbous head and her hand continues to stroke my shaft. The vibrations from her moans are too much for me to take and my cock swells before I shoot my load into Amy’s hungry mouth and down her throat.

As Amy comes back down to Earth she removes my cock from her mouth and licks the remnants of my cum from my slit before collapsing onto the seat next to me. She offers me her cum soaked fingers and offers them to me. I eagerly take them into my mouth and suck them clean. “We’re almost there so we had better tidy up.” We sort ourselves out and talk for the rest of the journey, during which, her hand never stops slowly rubbing my thigh.

Very soon we pull up in front of a very nice shop, with several very cool suits in the window. Amy leads me into the shop. Standing behind the counter to the right of the shop is a women in, I’d say, her mid-40s, with short blonde hair. She is very smartly dressed, in a fashionable short black skirt and a tight, shimmering, silvery top, that shows off her curves. “Oh, Amy. How are you?” she cries, coming around the counter to kiss Amy on each cheek.
“Not bad, not bad. It’s good to see you Stacy. Now, as I told you over the phone I would like some suits for John here. I don’t care how much it costs, just make him look grand.” says Amy. Turning to me she says, “Well, I’ve got to go. I’ll be back later. Now behave yourself.” She turns and walks out, with a little smile.

“Right, John would you follow me please.” Stacy said. She leads me into the fitting area at the back of the shop. On three of the walls are full length mirrors to allow you to see what you look like. There are two chairs in the opposite corners and on a large rail to hang the clothes. “Now, would you kindly strip to your underwear.” I still have a bit of a boner from the little incident in the limo and don’t her to see it. As I undress I try to think of other things to distract myself. It works, as my cock begins to shrink a bit. Before I know it I’m standing in just my boxers and my cock is only just seem-erect. I just hope she doesn’t see it. Suddenly, Stacy drops to her knees in front of me and begins to take the measurement of my inside leg. I feel her place the tape at the top of my leg and my cock begins to grow. I try to hide it but it is very hard to so when someone is on there knees in front of you and all you’ve got on are boxers. When she sees the growing bulge in the material a small grin appears on her face. She looks up at me and says, “Don’t worry, it’s quite normal.” She stands up and takes the rest of my measurements. When she has finished she says, “I’ll be right back. I’ll see what I can find for you.” She turns and walks out of the room leaving me standing in the middle of the room just in my boxers, looking at my reflection.

A short time later she returns carrying several suits on their coat hangers, which she hung on the rail. For the next hour or so we go about trying on different types of suits; different style, different colours. You name it we try it. At no time does my cock go completely soft, as Stacy is always tracing her hand up my leg adjusting the material. Occasionally she brushes my dick and she adjusts the crotch even if I don’t think it needs it, and sometimes her hand would linger a second or two too long. I might have been me though.

Eventually we have got quite a collection of suits sorted and I’m taking off the last one and begin to hand it to Stacy. As I do she says, “You know all about you and Amy.” I look at her blankly. “Oh, come on. I know why she hired you. You’re hot and I know that she fucks her employees. So what makes you different? Nothing, she’s fucking you too. I bet she was doing you on the way here.” I go red as she is saying this. “Oh there’s nothing to be embarrassed about.” She giggles. “I can quite understand it. I mean…umm…well, never mind.” She says getting quite flustered.

I am by now I’m standing in just my boxers in front of her. I see what she wants. I see the lust in her eyes as she looks at me. I step towards her and take her hand and place over me boxers. I look into her eyes and say, “Is this what you want?” she nods her head slightly as she stares down at her hand. “Well, you can have it. Do whatever you want with it.” She looks at me, with eyes wide open in surprise. Then I see the lust in her eyes grow and as it grows so does her confidence. She drops to her knees and pulls down my boxers and takes my growing prick in her hands. She licks her lips before she takes the tip into her mouth. She immediately begins to feverishly suck it. She slides more of my cock into her mouth as she moans. She is an excellent cocksucker. She teases my helmet with her tongue as she sucks the rest of my cock. In no time at all she has me m
oaning as I place a hand in hair, holding her head.
After a few minutes she removes me swollen cock from her mouth, a string of her saliva stretching from her lip to my wet cock. She stands up with a grin. “Oh, I love blowjobs. Nothing beats the feeling of a nice piece of meat filling my mouth, except maybe filling me up other ways.” She giggles mischievously. She pulls her top over her head and unzips her dress, stepping out of it she stands in front of me in just her white bra and thong. She reaches behind and undoes her bra revealing her tits, which have huge nipples that are standing erect, begging to be sucked. She then turns around and pulls down her thong, bending over keeping her legs straight showing off her ass. Looking over her shoulder she gives me a lustful grin and a wink.