Kyla, 38 and Her New Slave Pt. 01

Cameron, Cam to his friends, had been without a female in his life for some time, ever since his girlfriend had gotten spooked when he opened up about his wish, no, his need, to be dominated by her. In retrospect he should have just kept his mouth shut and put up with the boring sex, satisfying himself with masturbating to femdom videos online, which is what his sex life pretty much amounted to now.

At 25, he had had his fair share of female partners, but was never one for one night stands, and since he could remember had had a thing about older women. So, when browsing some porn sites an advert popped up asking 'Would you fuck an older woman?', he immediately said 'Yes' out loud. Good job there was nobody near him in the public library!

He clicked the link and flicked through the photos. Most of them were old enough to be his mother or even his grandmother, and he wasn't quite ready for that. He had had sex with his Godmother, who was his Mother's friend, but she was still gorgeous and had fantasised about her since his first boner and when the opportunity to kiss her had presented itself at a family wedding, when he was aged 17, he couldn't resist. It was as good as he'd hoped, as were her small but perfect breasts, as he kneaded them clumsily. Her impatience had caused her to grab his wrist and push it down and up her short summer skirt. He almost came in his pants as his fingers found the hot damp gusset of her knickers, but his pleasure was cut short as she pulled away, pushed him back and said to him "if you're interested in learning then phone me on Tuesday around 10 a.m. My number is in your Mother's address book."

With that she kissed him gently on the mouth and then skipped away, back to the party.

He snuck away and found a small cupboard in the hotel where he wanked himself frantically, leaving his semen dripping from the handle of the vacuum cleaner, something that disgusted the housekeeper come Monday morning, who clearly knew dried up spunk when she saw it.

Anyway, I digress. You can find the rest of that story elsewhere. Trust me, it's hot, if you like that older woman - younger man dynamic.

Nobody on that older woman site really appealed to him, but then a new pop up caught his attention: The Hot Milfs Society. He flicked through some biogs, one of which caught his eye Kyla, 38, shapely brunette, WLTM submissive young man for training and worship, 4 miles from his location. Her photos were quite discreet; brunette, white, nice figure, well dressed. Her shapely legs clad in grey stockings in a short darker grey knitted dress showed a hint of stocking top, no more than that, but he sat transfixed by her.

Although her figure was, in his opinion, perfection, she wasn't what you would call a classical beauty, her face was, well, more handsome than pretty. Yes, a handsome woman, he concluded. She certainly wasn't repulsive by any means, and kind of looked like Nigella Lawson, the TV chef, but not nearly as voluptuous.

He browsed through to her biography: She was a single woman, independent, and with all her own teeth. She obviously had a sense of humour, and the aforementioned teeth added to a nice smile, her face framed by a chestnut bob, kind of like that Rachel or Jennifer Anison cut.

He looked at a few more profiles, but came back to Kyla, 38, and the more he looked, the more his imagination ran riot. By the time he got home and closed the door to the outside world, his cock was hardening and he hurried to his bedroom, stripped naked and lay on the bed, tablet in hand, fantasising about Kyla. He imagined she would order him to kneel before her and perform cunnilingus on her. His cock was rock hard and he pulled back his foreskin, wetting his index and middle fingers with saliva, before rubbing them around his glans, the skin of the purple head became hard and shiny and soon absorbed the wetness. He repeated the procedure, fantasising that Kyla, 38, was licking his cock. He changed his grip and began pumping his foreskin back and forth, squeezing his erection until his cock head went from from shiny purple head to almost avocado like skin. He liked it when that happened, which it only did when he was exceptionally turned on. His wanking got faster and faster and of course in his wanktasy, that is a fantasy whilst wanking, you're welcome, she came just as he did, his come spurting out of his pulsating cock head, two strings of spunk hitting him in the neck and shoulder. He had never come that much or spurted that far before, and his orgasm was powerful and lasted several seconds, his head spinning at its ferocity. He lay back, breathing hard, the options racing through his brain. If thats what looking at a few photos of her could achieve, what would actual sex with be like? A-fucking-stounding! he surmised.

He wiped the cum up, and couldn't resist sniffing the tissue. He had always enjoyed the smell, but had never plucked up the courage to taste it. Oh how that would change!

Back in the real world, he put in his credit card details for a three day trial on the Hot Milfs Society website, quickly made a profile, added a few pics, and then sent Kyla, 38, a message.

Within an hour his email beeped and his fingers twitched as he hovered over the hotmail button. He hit the open button and the email sprang onto the screen.

Kyla, 38, was, it said, very interested in his profile, and he hit the read message button.

Hot Milfs opened and he logged in, he went straight to his Inbox. He was surprised to see there was more than one message but he by passed them all, and opened Kyla's message. Sorry that should have read Kyla, 38's message:

She was very interested in him, liked younger, submissive men and suggested they exchange some more emails, before they went further. Her email address was there and he added it to his contacts.

The next three days were filled with short poignant emails, her likes were, of course, cunnilingus, plus obedience training, spanking, mild bondage, humiliation and orgasm control. He asked for further details of the last four but she merely said that she would prefer to save it until they met. That last phrase until they met made his cock pulse, and the next, asking him for a full naked photo and a close up of his erection and scrotum had his hand shaking.

He took several photos and cropped them before emailing them off. He didn't have to wait long for a reply, but the content shocked him: what did he mean by sending her a penis pic without shaving his scrotum first? Oh, and while he was at it, crop the rest down to a number two. She expected a reply, with new pics within the hour. He stripped and set to work. Having never shaved his pubic hair before, it wasn't a short process, but he completed it without drawing blood, thankfully, and then having got himself erect once again, re-took the photos. He pressed Send five minutes before the hour was up, and sat back, absentmindedly stroking his cock to full hardness again before wanking himself. Her reply pinging back to him before he came, luckily for him, in hindsight. She was pleased with his handiwork, commenting that an erect penis always looked bigger after the pubic hair was shaven, adding that she hoped he hadn't masturbated without her permission.

He took his hand away automatically, not wishing to disappoint her.

Her email went on to say that if he wished to serve her, then he would, as of now, only masturbate after asking, and receiving, her permission. He was to email her back immediately agreeing to her conditions.

He replied that he didn masturbate, which is true, kind of, and that he agreed to her conditions.

Her reply told him, not asked him, to send his mobile phone number, and then to kneel at the side of his bed, naked, and await her call.

He quickly sent his number and did as she ordered. His heart was beating almost out of his chest and his erect cock pulsed and jerked spasmodically as he knelt and waited.

After ten minutes he phone buzzed; it was a text message - "Are you kneeling as I ordered?"

"Yes" he replied.

"You will address me as Miss Kyla, until you have earned the right to call me Mistress. As of now, you will no longer be called Cam, you are simply Slave. Do you understand?"

"Yes, I understand, Miss Kyla" it took all of his willpower not to add "38" after her name.

The next text asked him if he had a Skype ID. He didn't, and said so.

"Can you download the app to an iphone or tablet? If so, do it and tell me when you have downloaded it and set up an account."

"Yes Miss Kyla, I'll download it now."

The download went fairly slow, along the lines of a watched kettle, but eventually it completed and he opened it and set up an ID, as Slave Cam, and texted her back.

He opened Skype and waited. Within five minutes, with Cam kneeling throughout, the familiar Skype calling tone sounded on his tablet. Cam swallowed, cleared his throat and pressed Answer.

The video screen opened and then Kyla, 38 appeared on his screen. She was dressed all in black, black blouse, black skirt, black tights or stockings and sat with her legs crossed, the hem of her skirt demurely covering her right knee.

"Well, well, well, who do we have here?" she asked, a little laugh in her voice.

"I'm Cam, Cameron" he replied, quickly adding "Miss Kyla."

"No, no you aren't, and I shan't tell you again!" She snapped.

"Apologies Miss Kyla. I'm slave, Miss Kyla."

"Quite" she replied, then surprised him by asking "Do you have an erection slave?"

"Yes, Miss Kyla."

"Show me." She commanded.

He angled his tablet down and steadied it on his erection.

"Hmm, not very big is it?" her first humiliating comment, but certainly not her last.

"I...I thought you said it looked bigger when shaven, Miss Kyla?" he asked.

"I suppose, but not really long enough and certainly not thick enough to satisfy a real woman." Her second humiliating comment.

He had always thought his cock was a good size, nice head, a little bend in it, not too pronounced, and had even been told he had a 'pretty' cock by one girlfriend.

"May I ask a question Miss Kyla?"

"Go ahead" she replied.

""If my cock is too small, what size do you prefer?" he asked.

"Well my lovers are eight and eight and a half inches long, the shorter one is a little thicker, but they are both the thickest I have ever had." She said, matter-of-factly.

All he could muster in response was "Oh!"

"So you cannot hope to satisfy me with your cock alone, your role would be as my tongue slave,"she paused momentarily, "if I choose to add you to my stable. Anyway, before we get to that decision you need to provide me with your health report. No report, no intercourse, it's as simple as that."

"How do I do that, Miss Kyla?"

"You go to a G.U.M. climic and get checked out."

"What is G.U.M. Miss Kyla?"

"Genitourinary Medicine, the clap clinic, basically."

"Oh, I see, Miss Kyla."

"So, when terminate this call, I want you to call the clinic and see if you need an appointment or can just walk in."

"Yes, Miss Kyla."

They talked some more and she set out her rules: obedience, fidelity, for him, not Her of course, no masturbating without permission etc. She asked him if he had any fetishes.

"Only, stockings, suspenders and high heels Miss Kyla."

She stood in front of her laptop. "Would you like to see my stocking tops, slave?" She asked, rather surprising him.

"Yes please Miss Kyla." he replied meekly.

She slowly inched her skirt up her thighs rather teasingly, until her stocking tops came into view, then a little higher until her creamy white thighs filled his screen, and he saw the lacy suspender attached to the wide lace stocking tops. She stopped short of her crotch, disappointingly, but then turned around. The backs were attached to two suspenders on each thigh, her suspender belt was a six belt article. He'd only seen pictures of such before and it excited him a lot to see her wearing it.

She completed the turn and sat back down.

"Is that the kind of thing you like?" She asked him.

His mouth was suddenly very dry and he could hardly reply, the "Yes, Miss Kyla" coming in a hoarse whisper.

"And lingerie? Do you like lingerie?" She asked as she sat back down.

"Yes, Miss Kyla."

"Lacy knickers perhaps?"

"Yes, Miss Kyla."

"In which case, I expect you to wear them whenever we have a session. Are you a virgin?"

"No, Miss Kyla."

"Oh, so when was the last time you had your hole penetrated? Was it a strap-on or a penis?"

"Er, neither Miss Kyla."

"So,you are a virgin? You've never actually been fucked deflowered? Do you suck cock?"

"No, Miss Kyla."

"Hmm, I won't pretend I'm not disappointed. Anyway, as you're a virgin, you will wear white lace knickers. Make sure you go out and buy a pair, the lacier the better."

"Yes, Miss Kyla."

"And while you're shopping you can buy me two pairs of black stockings, lace tops, I take size 6 shoes and my legs are 32 inches long, in case you need to know."

The thought excited him, the feel of the lace against his cock, the knickers stretched tightly across his arse, and he could see himself kneeling in front of Her, putting the stockings on her shapely legs, and fastening the three suspenders to each one. He glanced at the clock and thought that if he could get to the shops in the next hour he could buy something appropriate, or inappropriate, depending on your point of view.

Her voice snapped him back to reality and She asked if he would like to see more?

He did, of course he did, and he was transfixed as she uncrossed her legs and opened them, slowly pulling her skirt up her thighs, teasing him, until the hem was up to her hips and she opened her legs to show him the crotch of her lacy black knickers. He was surprised that she was unshaven or at least not completely shaven, an inverted triangle of pubic hair visible through the sheer nylon, but the gusset covered her cunt lips.

"Like what you see, slave?" She asked.

"Yes, Miss Kyla, you are extremely beautiful. Thank you so much"

"Well, you wont be seeing any more until you enter my service."

She looked at her watch, then back at him, and stated she had an appointment shortly, and that she expected him to do as she had told him in the next hour, and to expect a call back then.

Some further small talk was interrupted by her saying "A-ha, there's the doorbell, remember, back on your knees, naked in one hour." and with that she cut the call, before he could reply. He knelt there, looking at the blank screen, and said "Yes, Miss Kyla, 38."

Cameron, quickly found the number for the GUM clinic and found out they were open until 7:20 pm. He phoned and was told that if he could get there in the next twenty minutes there was a cancellation. He did live too far away so took the appointment, pulled on some clothes and set off. Thirty minutes later he was all done, he paid the fee for fast-tracked results and set off into the city to make his purchases. Back home with two pairs of black stockings, one with a wide lace top, the other plain, and one pair of large white lace knickers, he ran upstairs and tore his clothes off. He glanced at the bedside clock, more than an hour had passed, but his Skype didn't show a missed call. Perhaps she wasn't calling back, perhaps it had all been a massive waste of both time and money, perhaps she was just another prick teaser. Those negative thoughts made his fresh erection wilt, but he knelt by the bed, hoping against hope for the Skype ring tone.

He'd been there five minutes and he had resigned himself to yet more disappointment, his forehead slumped on the bed. He was shaken out of his thoughts when the ring tone began sounding, surprising him. He looked at the screen, it was indeed Kyla, 38, and he pressed the answer button. The video screen leapt into life and there she was, looking somewhat different to an hour ago: her hair was messed up, her black silk blouse replaced by a black silk kimono, a hint of cleavage and black bra peeking out. She was fixing her red lipstick and totally ignored him until she finished it, before lying the hand mirror on the bed then replacing the top of the lipstick.

"So, what did you do while I was busy, slave?"

"Er, I went shopping Miss Kyla, and had a blood test."

"So soon?"

"I got a cancellation Miss Kyla, and should have the results within a few hours."

"Excellent. What did you buy?"

He held up the two packets of stockings for her to see, and she asked if there was anything else.

He put the stockings down and picked up the white lace knickers.

"Quite pretty." She commented "And why aren't you wearing them?"

He stammered a reply about waiting for her permission.

She told him to try them for size, and he stood and held them ankle high, before stepping into them and pulling them up his legs. He loved the feel against his skin and as he pulled them up tight his cock swelled against the sheer nylon. He went to kneel again, but She told him to show her and he twirled around until he faced her once again.

"Take your cock out of the side, and leave it there."

He did as she ordered, his erection sticking out of the left side of the front. "Now wank it slowly." He wrapped his hand around his throbbing erection and began to pump back and forth. Much longer and he wasn't going to be able to stop, but she ordered him to put his hands behind his back, them almost as an afterthought to kneel.

He did so and waited for her to turn her attention to him.

"So, you seem to have passed the first part of the interview. Shall we move on?" It was of course a rhetorical question and he murmured his assent.

"Do you have any questions, slave, about say, what I did while you were out?" Her perfectly plucked eyebrow arched seductively, a slight smirk on her luscious red lips.

He was anxious to know exactly what she'd been up to, but didn't dare ask or appear to be too nosey. "I didn't think it was my place to ask Miss Kyla." he replied diplomatically.

"Well, I give you permission to ask." was her curt reply.

He swallowed hard and took a deep breath through his nose.

"Did you have a visitor, Miss Kyla?" She confirmed she did.

"Was it your lover, Miss Kyla?"

"One of them, yes. would you like to know which one?" He did of course. "It was the shorter one." She laughed as she said it, adding, "in fact he's head and shoulders shorter than me when I'm in heels. Makes it easier for him to suck these." She undid the kimono and slid it off her shoulders, exposing her bra, the outlines of the hard nipples clearly visible through the black platform bra, edged with red lace. "Is that something you would like to do, slave."

He almost tripped over his words to say that he did. She took her small but perfect right breast in her left hand and caressed it outside of her bra, before slipping her hand into the cup, pushing the material aside and exposing the breast to him.

"Small, aren't they?"

"They're perfect, Miss Kyla." he replied, adding in his head "You're perfect, Miss Kyla, 38."

"Next question." She commanded, slipping her breast back into her 34 b cup bra.

Did he fuck you was too obvious, of course he fucked her, so he asked "Did you suck his cock, Miss Kyla?"

"Actually yes, I did. I love to feel him grow hard in my mouth, and the saliva helps lubricate it when he fucks me." Obviously. "Do you have good staying power slave?" She didn't wait for a reply, adding "he does. Unfortunately, he can't get another erection for hours. How do you match up?"

He swallowed and said "I can usually last twenty minutes, Miss Kyla."

She laughed "well he can last forty. So I can see that I'm going to have to teach you some self control. Ha! What use is twenty minutes to me?" another rhetorical question, "You'll spend more time with your tongue in my cunt! Next question!"