Clementine in Hand-me Downs

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Clementine is dressed by 'M' and watches a video.
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Clementine was quite eager to see 'M' again at his house. Their time together at the office was so impersonal, no-one there could have guessed that Clementine had any type of off-hours relationship with "the boss!"

Clementine rang 'M's doorbell and he quickly opened the door and let her inside. At first he did his usual (what she called "inspection") routine, of having her stand still and turn slowly so he could absorb what she was wearing. Today she had worn a lovely plaid straight knee-length skirt over a girdle, white slip and tan seamed nylon hose, along with a sheer 1950's era blouse and sweater. It was one of her "librarian" outfits, the conservative outfit only offset a little bit by the somewhat kinky dark-brown lace-up high-heeled oxford pumps she wore. The nylons and shoes were a definite hit, she could tell from the way 'M' ogled them.

'M' had her face-away from him and she felt him come up close behind her, he gently wrapped an arm around her waist and bent his head to nuzzle at her hair. "You look truly lovely today my sweet. That outfit captures the era in question to a 'T' and brings back many happy memories for me, of the lovely ladies dressed just as you and the pleasures they provided.

Clementine felt 'M' turn her around in his arms and he gave her a long hug. She relished the lovely warm way he held her and she was enveloped in his wonderful warm manly smell.

"Kneel, Clementine," 'M' said after breaking their hug, and Clementine obediently sank to her knees in front of him.

"Kiss it," 'M' said and not-so-subtly thrust his crotch forward at her face.

Clementine placed a well-aimed, lingering kiss on his bulge, where she knew the penis was nestled against the balls inside his pants.

'M' casually held her head against his crotch as he spoke, "today I have a special treat for you my lovely vixen. I have picked out a certain outfit from my wardrobe of treasures from ages past, you will find it laying on the bed in your room upstairs. I want you go upstairs and dress yourself in the outfit and return here quickly so we can continue our game. Is that understood, my sweet?"

"Yes, I love you and want to make you happy and please you in every way, dear Mentor" said Clementine and she meant every word, kneeling there, her face against his bulging manly crotch.

'M' grunted approvingly. "Very well, off with you then! I will be waiting for your return in the sitting room in front of the tv." 'M' then stepped back and allowed Clementine to rise to her feet. They shared a deep passionate glance, and Clementine went upstairs to what they had begin calling "her" room.

Upstairs, Clementine found some clothes had been placed on the bed. There was a black, plain, long nylon slip, sort of ugly to tell the truth. There was a pair of sheer black nylon panties, there was a white cotton plain-jane garter belt, there were some nylons, off-black in shade, with seams. And a pair of wild (and sort of ugly) 1970's era wooden high-heeled sandals with leather ankle straps. The outfit reminded Clementine of some of the things she had seen the ladies in the 1970's Swedish Erotica loops wear. And it seemed these clothes had been worn before. They smelled subtly of perfume, maybe even faintly of sweat, the stockings had the little picks that stockings get when they're worn, and the slip had some stains or smears along the back.

The whole situation was a little strange, Clementine could not figure out 'M''s intention. She did not think he had owned any of this stuff, she knew he was not a crossdresser himself (thank God!), whose stuff was this? And why was it so out-of-date?

Well, it did not really matter, to please 'M' Clementine would certainly wear these things. Not to mention, feminine finery of any sort gave her a lot of pleasure, and these clothes had the additional pleasure of obviously having belonged to someone else at some point, they were not new... Clementine liked to dress in "worn" clothes and imagine herself living the lives of the people who had worn them. Each frock, each skirt, each blouse had a story to tell in Clementine's fevered imagination.

So, with shaking fingers Clementine removed her street clothes and shoes, and tried on these things 'M' had left for her. Beginning with the garter belt, she found it fit her at the waist but the hips were too big, whomever this had belonged to had had bigger hips than Clem. Then the stockings, each one was a little too big and long, so combined with the loose garter belt the stockings drooped a little bit, bagging into lovely nylon wrinkles at ankles and knees. Clementine herself loved these little wrinkles, but would 'M'?

Pulling on the lovely sheer black nylon panties Clementine noticed a few stains on them too. What was that stuff? Was it from storage or ...? She half wanted to sniff the stuff but decided not to. The panties too were a tad big, Clem's hips were simply not big enough to fill these panties out, but at least they did not slip down, they were just a little baggy, which sort of accentuated her ass-cleft when the material became trapped there as she stood up. She pulled that ugly plain black nylon slip over her head, it came to just above her ankles, showing her pretty nyloned feet to good advantage but as a whole the slip was ugly and shapeless. Finally, Clementine put on the high-heeled sandals, they were (she had to admit) sort of sexy, almost the entire foot was visible, held in place by thin leather straps at the ankles and at the toes. Her stockinged feet were forced into lovely arches by the shoes' bindings! And the heel height made her buttocks visible beneath the slip. Looking at herself in the mirrors that covered one wall, Clementine felt her clitty stir in the panties as she considered her somewhat slutty appearance, the plain black slip was drawing attention to the stockings and those shoes! Again, images came to Clementine of the many 1970's era porn-loops she had seen, where the ladies sometimes dressed like this. Clementine smiled to herself and considered if she could afford a quick wank before she went back downstairs. But wanking now would feel like cheating 'M' so Clementine carefully made her way back down the stairs and into the sitting room.

'M' was sitting on the couch in front of the tv, the television was on but there was no picture showing. 'M' had poured himself a drink of some sort but he did not offer one to Clementine. When she appeared 'M' put down his drink and just looked at her. After a few moments she slowly turned around so he could see her from all sides.

"My God, Clementine, if you could only understand what I am feeling seeing you in that outfit!" exclaimed 'M' in a somewhat uncharacteristic manner. "You look lovely, my dear girl! Let me enjoy your appearance for a few moments more, then come here and kneel beside me".

After a few moments Clementine teetered to where 'M' was sitting and she carefully sank to her knees on the floor in front of him. "Does he want me to suck him?" she wondered but then 'M' used his hands to gently position her in a kneeling positon, on hands-and-knees to be exact, with her ass towards him, her ass against his thighs where he sat on the couch, and her face towards the television screen.

"My dear Clementine," 'M' began, "I am going to show you a film no-one else has ever seen except for myself. It is only recently I have come to appreciate the pleasures of those of the, shall we say, third sex, like yourself. Until I met you I have devoted myself exclusively to girls and women. I want you to appreciate what a compliment it is for you to receive these affections and interest from me, it is because you are genuinely pleasing and attractive to me that I have allowed you to join that select club of the women in my life, the lovely ladies that have been privileged to serve me and of course it has been my honor to serve them!"

"In any case, let me share this movie with you. It features myself and my lovely wife and takes place in the mid-1970's. The evening the film was taken we had been out playing bridge with our neighbors the Williamsons and my wife had taken every opportunity to tease and torment me secretly underneath the card table as we tried to keep up appearances. I am sure she had planned to excite me in this manner, in the hopes I would treat her in the way you will witness..." And 'M' used the remote-control to start the movie.

The video opened showing a handsome mature woman, dressed in the same outfit Clementine was wearing. The lady was sitting on the edge of a bed and was talking to someone off-camera, she had a very flirty expression on her face and she would tease by sitting back and spreading her legs (visible underneath the slip thing) and then sitting up again and keeping her knees together. Finally she laughed and Clementine watched her turn around and climb up on her knees on the bed, her ass facing the camera. The lady looked back over her shoulder at the camera and then she went down on her elbows to raise her ass (still covered by the slip) higher. She looked back again, and then shifted a little on the bed so her ass was center-frame. It was obvious she was being directed by whomever was running the camera.

At this point the camera shuddered a little and suddenly the body of a man appeared, totally naked, very strong looking and nicely hairy. His large, almost fully stiff cock was hanging ponderously from the bush of his pubic hair and there was a mass of hairy balls visible beneath it.

"That was me then, I haven't changed all that much, have I my sweet?" said 'M' while he began to stroke Clementine's buttocks. Clementine looked at the man's cock in the movie and reminded herself that she had in previous encounters sucked that thing, she had even taken it deep in her pussy, it seemed impossible that such a huge thing could fit but it had, and the idea remained incredibly exciting, the thoughts alone sending what felt like electric jolts of urgency all through her body!

The man in the film half-sat on the bed next to his wife's ass and began stroking it, much like 'M' was stroking Clementine now. The man in the movie was more aggressive in pawing at the crease between the lady's cheeks and he quickly got to the point where he was lifting the slip up over the lady's legs and exposing her nyloned thighs until Clementine could clearly see the top of her stockings exposed.

"I was quite the eager stallion, than night, wasn't I?" muttered 'M' from his position behind Clementine.

The man in the movie suddenly stood up behind his wife and he started rubbing his cock against her ass-crease, bunching the nylon of the slip into the crease, at one point he grabbed the lady's hips with both hands and started humping against her roughly, Clementine could see the lady's feet flop helplessly as she was bopped against the man's thighs.

"Quite the stallion indeed," Clementine heard 'M' say. And as the movie continued Clementine heard the sound of a zipper opening and she could feel 'M' shift on the couch. Suddenly she could feel a very warm thing -- it could only be 'M''s cock -- rub up against the crease of her ass, still covered by the black nylon slip.

"Turn your head for a second and look," 'M' commanded Clementine, and Clementine looked back over her shoulder and saw that 'M' had indeed released his magnificent cock from his trousers, and it rose red and angry over her buttocks, resting its length against the crease of her ass. 'M' was wearing a sublime, lecherous expression as he stroked his cock a few times for Clementine's gaze. "Continue watching the movie, dear," 'M' told Clementine, and she turned back to the television, feeling 'M' continue to rub his rampant cock against her covered bum.

The man in the movie had now returned to a half-seated position beside the woman's ass, and the lady had one hand reached back and was stroking the man's cock as he further pulled up the black nylon slip and uncovered the lady's sheer panty-covered ass (the very same panties Clementine was now wearing, Clem reminded herself). As the woman continued to awkwardly stroke the man's penis, he pulled at the elastic of her panty crotch trying to dig his fingers underneath, trying to pull the panty-crotch aside... Suddenly the man gave up and briskly just pulled down the panties to the lady's knees, exposing the glorious shapely ass of that lovely mature woman!

Reaching for something on the bed the man's hand reappeared holding a tube of some kind of lubricant, the man applied the tip of the tube to the woman's anus and he then used two fingers to smear whatever the lube was around the edges of the lady's ass and then jabbed a finger and then two fingers into the woman's anus, he then applied more stuff from the tube, then the man continued to use his fingers to enlarge the woman's hole and to lubricate it further.

As this was going on, Clem could feel 'M' was pushing against her own anus using his penis and fingers, she was still wearing those panties and the nylon slip over her ass but she could feel 'M' digging through those layers of nylon to stimulate her opening and his own cock at the same time. It felt so sexy.

And then, surprising Clementine with its suddeness, the man stood up again, quite without foreplay the man just grabbed his cock and jammed it against the woman's anus and suddenly the man had breached that tight hole with his shaft halfway inserted. There was no sound to the film and you could not see the lady's face but you could tell from the way her body reacted and the way her feet, legs, hands, and fingers splayed that this aggressive sudden anal penetration had been quite a shock to the lady too.

"Sometimes you have to be rough to be kind," Clementine heard 'M' say in a husky voice. "With all that lube she could not prevent my penetration, her anus was forced open to allow my cock's entry."

On the screen the man was now fucking the woman's ass full-bore, long strokes that exposed his entire shaft, her body was bent, the upper part of her body flat against the bed, her ass in the air. The man made a show of the fucking, he would pull out completely and rest the tip of his greasy cock against her anal opening, wait a beat or two, and then plunge in again. The large balls never stopped moving. It was one of the most erotic sights Clementine had ever seen!

Behind her 'M' was still firmly manipulating CLementine's ass-cleft with his hands and penis. Clementine could not help arching her back further and she clenched and unclenched her anus in involuntary delight, obviously 'M' could feel her anus "wink" even through the layers of nylon because she heard him say, "Good girl!" and he reached forward to grab at her hips to hold her while he ground his penis into her asscleft.

Clementine, her eyes glued to the "ass-rape" on the screen felt such a slut kneeling there in those clothes, her ass in the air, being molested by that rough lovely man behind her :) That woman on the screen had turned 'M' on, she, Clementine, had also turned 'M' on! It was such a relief this wonderful man found her attractive and worthy of his attentions!

The man in the movie had now also gotten onto the bed, he was crouched in a sublime, exquisite posture of copulation over the ass of the woman, his cock pounding again and again into her wet anus. He was dominating her fully, that age-old dance of male over female, she was the willing recipient of all that lustful energy, that "need-to-breed" that animates so much of life. His cock now looked truly huge from all that lustful stimulation, it was shiny and greasy from the lube and other fluids and it worked its magic in the woman's upturned bottom. And, because 'M' was a true sensual artist, he would sometimes pull out completely, exposing the woman's gaping anus and the entire length of his cock and its wonderfully bulbuous head to the gaze of the camera, almost as though he knew at the time of filming that Clementine would one day be viewing it!

"Lovely, don't you think?" 'M' said. "Can you believe you had that whole thing in your asscunt the other night? Like a good bitch, I might add. You're quite the natural bitch, my dear Clementine. Even now I can feel your asscunt twitching. Perhaps you're thinking of receiving this same rough treatment, wearing these same clothes?" Clementine did not say anything, she couldn't, her mind was so focussed on the erotic sight before her on the television screen, and on feeling 'M''s manipulation of her bum, and on hanging on his every word. She couldn't answer but she could hump herself back against his fingers and cock, and she whimpered slightly in her need.

"Mmmm, my little whore.... let's finish watching the movie, my dear."

The movie continued, the man continued fucking the asshole of that woman on her knees, her slip pulled up, her panties pulled to her knees. The man was now fucking harder, he was pulling out less, it was obvious he was reaching his climax as he kept his cock deeper, he fucked with shallower strokes but buried further into that ass, then Clementine could see him push hard against the woman and he was buried deeply only his balls showing -- the onscreen 'M' was cumming!

'M' spoke, "I had trained her to hold me tight as I would cum, she would use her anus to milk my cock as I came deep in her, there is no better feeling for a man than a woman who eagerly uses her asshole to milk the cum from his cock. This is something I intend for you to learn, dear Clementine, to truly become the woman I need you to be to serve me."

On the screen the man had stopped moving, the two figures were locked in that lewd canine copulatory embrace for what seemed like many minutes. Then slowly the man released his grip on the woman's hips, and he slowly pulled his penis from her anus. A great length of greasy man-meat was exposed, its entire tip covered in white cum!

Then, still crouched above the lady, the man in the film used the back of the woman's slip to insolently clean his cock. 'M' paused the film at this point, that frame of cock-being cleaned frozen onto the televsion.

"And that explains the condition of the slip you are wearing Clementine, those stains, my sperm to be exact, are more than 30 years old! I have kept this outfit as a trophy of that wonderful night, a great assfuck captured on film, and it is a true delight to see the outfit being worn again, especially by someone as lovely as you, my dear Clementine."

Clementine could not take her eyes off of the screen, her eyes glued to the image of that huge cock being rubbed with that slip she was now wearing, and to feel the real-life sensations of that same cock rubbing into and against her asscleft. It was sensual overload and she was entirely under 'M's spell.

"Now my dear, you have a decision to make." 'M' spoke as he continued to playfully stimulate her. "As you can tell I, like you, have been very stimulated by this film. Additionally I am very stimulated having you here, dressed in that outfit which brings back many memories. I would very much like to play at "ass-rape" with you, there's no gentler way to say it. I would like to fill your asscunt with lube and then I would like to fuck you in a rough manner, like we saw on the film. I can tell you the rewards for us both will be exquisite. But I will not force my rougher attentions on you without your permission. So, the decision is yours. If you would like to be treated like the wonderful lady in the movie, I want you to go upstairs to your room and sit on the edge of the bed as you saw her sit at the beginning of the film. Events will then progress from there, and I will even film our copulation so we can compare the two events later. But, if you feel you are not ready to progress to this stage at this time there is no penalty, I would be quite happy to have you suck me off as I sit here. The choice is yours, go upstairs and wait for me, or turn around and kiss my cock..."

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