First Pain Turns to First Pleasure

The phone rang and I cursed. No-one knew I was at home, so it must just be a sales cold caller. I knew how I was gong to put them off.

"Hello, Pain and pleasure, your pain is our pleasure," I said, on picking up the phone.

A familiar voice said, "Oh, sorry, I think its the wrong number. I was looking for Andrea." The voice belonged to Fay, a colleague of my partner who I remember seeing at regular functions, and who was, if I remembered rightly, quite starchy yet very hot. What on earth have I said!

"Hi, Fay, its OK, Andy here. Just wanting to put off the window salesman. What can I do for you?"

"Oh, I was hoping to chat with Andrea, I thought she would be about", she said, sounding flustered but there was something else there in the slowness of her reply that I couldn't figure out.

"Away, couple of days on that conference she needed to go to. Can I take a message and get her to call?" Andrea was my partner, and worked with Fay allowing me to meet her and a couple of other undeniably sexy co-workers at social events.

"Ermm, away, couple of days.. well, no, it can wait, thanks, see you soon I hope," came the slightly husky reply. With that she hung up.

I went back to work, wondering at my daft opening lines and what Fay and Andrea would say about it. I was deeply involved in some long-winded report when I was disturbed again, this time by a knock on the door. I tried to ignore it, but it came again. Heaving a sigh I went to the door prepared to vent my wrath on the unfortunate sales person, but was taken aback when I saw Fay at the door.

"Oh, well, I thought I said Andrea was away," I said, lamely, as I admired Fay from the safety of my hall.

"You did, but I, er, I wonder if I could have a private chat about something. Erm, well, I seem to recall something about pain and pleasure. What was it? Your pain is our pleasure?? Mmm, I wonder if we could have a, well a private chat about this? You know, off the record, not something we might share type of chat?"

Forward, but with a hint of nervousness, and I stepped aside to invite her in. I watched her pass me by and enter the house, just wondering what this might turn into. Fay is a tall, striking lady with a full figure. She was showing this off nicely in the smart but tight dark greye business suit, pale red silk blouse and shiny seamed nylon covering her legs. Her height was emphasised by the red stilettos she wore, making her already tight figure even more attractive.

I quietly locked the door and went through the rear room. Here we were not overlooked, and closing the door to the front of the house I motioned Fay to sit down. Offering her a drink (she asked for wine to calm her nerves!) I asked her what had made her call to discuss my rather offhand remarks.

She took a gulp, uncharacteristically nervous, and said that the words struck a chord and she wanted to know if I was joking or was there something I could do to help her. Go on, I asked, and she looked at her wine and explained that she was surprisingly excited by the words I spoke when answering the phone, and even whilst talking about the mundane, of meeting up with my partner, her mind was wondering what I meant. She had to come and ask, and see if I was able to explain or even demonstrate.

I stayed quiet, nodding occasionally and then asked her if she had any experience of what she thought I might have meant when I said that her pain was our pleasure. I waited for her response, wondering where on earth this was leading, but not at all willing to let it go before finding out. Here was a very smart, attractive lady about to tell me what sort of pain for pleasure she might be willing to entertain, and with the chance of me providing the pain, it was already turning out to be an interruption I would not forget.

"Well, not much, but what I have tried I was so aroused by I know I need to try and find out more. I had ignored it, thinking it would go away, but your voice and those words made me think again. Perhaps there is a safe way to see what I, well, what I can endure and enjoy at the same time."

"Go on, what have you actually tried?" I asked, watching her wriggle a little as she took another gulp of her wine and lowered her eyes a little.

"Just a little spanking from my husband. i don't think he was very good, and I so wanted to continue but after what seemed barely a few swipes, he gave up thinking he had really punished me. I just felt I wanted more but couldn't explain to him, so the desire is there but not the experience."

"So, why did you come over, do you think I can help? Do you want to experience pain and pleasure from and with me??"

There, I had said it and given her the option to back off now, but she didn't. She just nodded, gratefully, and said, "Yes, I think I do. When you spoke those words, it triggered something and I know I can trust you from all our chats when we met at the work socials. I know this might be behind Andrea's back, and its certainly behind David's, but that is not a problem for me."

"So, this is between you and me. You are happy to trust me to treat you like you have never been treated before, and like you think you want to be?"

Fay nodded, breathing in and looking me straight in the eye before she said, "Yes, I think I am ready to try this, its been on my mind for so long I could not miss the opportunity you gave me. Assuming you still want to play...?"

Did I ever. Here was a highly attractive lady willingly giving me the right to spank, whip or anything else I fancied in the name of creating pain for mine and her pleasure. I knew we could do this, I knew exactly where I was going to start and this was indeed going to be fun for me, and undoubtedly painful for Fay. Only time would tell if it would be pleasurable.

"Mmm. Listen and nod only when I ask. You will now do as I ask. If you don't you will be punished. Sometimes if you do, you will be punished because I feel like playing and you are my plaything. It might be physical pain, it might be mental teasing, it will mean you may not have as many clothes on at the end of our session as you do now. It will mean you will be pleasured by your experience. You have an opportunity to decide this is not for you, and thereafter you only need to say the word 'beyond' to indicate the game will stop. I will honour that safe word, but no other pleadings will get you release. If you use it, that will be the last time we meet to do this. If you don't, and I end the session when I want, you may ask for another meeting which will follow the same rules. Are you remaining here?"

Whilst I spoke I saw a spark appear in Fay's eyes, but not of defiance but of hunger, of desire. She nodded, sitting with hands clasped on her lap and awaiting my choices. I wanted her to squirm, to use erotic language, horny language in public with me, something which most women are really uncomfortable with. This is the start.

"Describe the last time a cock entered you, in detail, and how you felt about it."

"Sorry, the last.. ... Oh, sorry".

Fay had started to query my instruction, but realised a little too late that this was now for real, and doing such a thing was not a good idea. I beckoned her towards me and sat down, motioning her to my right side. Indicating she was to bend over, I placed my hand in the small of her back. She knelt initially and leant across my spread thighs, easing herself into perfect position with her covered ass up in the air and her head and hands hanging down. I rubbed softly across the tight fabric of the business suit for the first time, and felt Fay shiver. The faint outlines of a suspender belt were showing now the fabric was so stretched into place across her full cheeks. Her dark, nylon covered legs were so close and tempting, but instead I just hooked my fingers under the hem of the skirt and pushed it smartly up and onto her ass. Presented before me was a perfect sight, the round, firm flesh barely concealed under a pair of skimpy red, lacy knickers. The straps of the suspender belt showed dark against the pale flesh, three broad bands of fabric holding up those black, slinky stockings.

Without warning I brought my hand sharply down on her right cheek, and she gasped audibly though more from shock than pain. It was a warning blow, and I rained a few more down on both cheeks, sharp but not too hard and all the while with the soft red fabric taking some of the sting from her. After a good 5 or 6 spanks on each cheek I stopped and rubbed lightly over the red marks appearing at the bottom of the fabric, where my hand had strayed and caught some bare flesh. Teasing and stroking that most erotic of places, the ass cheek turning into full thigh and sliding into stocking covered leg, I sampled the firm, smooth flesh of Fay for the first time. Then before she could get too comfortable I reached up to the top of her knickers and slowly but surely tugged them down, She lifted slightly to let them slip off her bottom and I moved them as far down as the tops of her stockings, exposing all of her fantastic fleshy globes for the first time.

I swiftly brought my hand down on the now exposed flesh, and it was a satisfying result. Fay started a little and a small gasp escaped her lips for the first time. The feeling of the smooth skin under my bare hands was much more erotic than through the silky knickers, and the impact of the blow was clearly greater. I continued, raising my hand ever higher and bringing it down with some force onto each cheek in turn. Fay groaned with each blow, the skin of her cheeks beginning already to show darker red as the blood came to the surface. The heat of the tortured flesh was apparent as I rubbed gently across her ass before completing my first punishment with three more lusty blows on each upturned cheek. Fay was breathing a little more heavily now, but had taken it very well and seemed to have understood that noise was to be kept to a minimum.

I stood Fay up, but left her knickers at the top of her thighs. She made to move them, then caught my eye and just stood still, awaiting my instructions. I moved her back to her hard wooden seat, and made sure that as she sat down, the back of her skirt was lifted and the well-spanked flesh was nicely in contact with the unforgiving seat of her chair. Her business suit skirt was smoothed down a little and vaguely covered the red fabric around her thighs. The sight was arousing me, and I could feel my cock hardening again as I looked at her face and asked her to now answer my original question. This time she started without question, though as her story unfolded she became redder in the face with embarrassment, and her eyes were lowered to avoid looking directly at me.

"Five weeks ago David came home from a night out having had a few drinks. Not drunk, but certainly influenced, and he was horny. He is never horny, and we rarely get together. I was in bed, and he pretty much foisted himself upon me. I had a nightie on which he just moved up and then played with my breasts for a little while. It wasn't long enough, I wasn't getting wet enough for him and he just decided to, well, to mount me anyway. He made love to me and we finished very quickly."

Fay rushed to the end of her story, and was clearly slightly uncomfortable with the telling of such details. Good, I thought, pain of a different kind. I needed more detail.

"A good start," I said, "but not enough information. So, how did he get you wet? Did he cum inside you? Did you have an orgasm? What did you do afterwards... you see you need to be more descriptive for me. I have already decided there will be some more strokes administered to that delightful, but so far barely touched, bottom of yours. If I don't get a full, arousing description now, it will be a lot worse. Go on."

Fay breathed deeply, and started again. She was squirming as she spoke, the heat of her punished cheeks causing her discomfort, though I was sure she was also now getting the arousal she was wanting.

"Well, he toyed with my nipples, which he knows are sensitive and arouse me quite quickly. He played with them until he thought I ought to be ready for him,.. for his.. erm, cock. When he touched me, my, erm.. pussy, and found it wasn't too wet and ready, he rubbed frantically up and down my lips thinking this would be enough. Very quickly he decided he couldn't wait, so he rolled on top and pushed his cock into me. It hurt a little but just having something inside me did help get me wetter. He did it, er, well, he made love to me for not very long before he tensed, grunted and I felt him cum into me. He is very quiet and he made hardly a sound. I had not had an orgasm, and was not even near one which was quite frustrating. He quickly went soft inside me, so he got off, kissed me briefly and was asleep soon after. I could feel his.. his... cum slowly leaking out of me so I cleaned myself up and went quietly back to sleep myself."

"Mmm, better and I can see it was quite frustrating for you. Is this what always happens?"

"Mostly, yes, though when we first got together it was different, or at least the memory of it is that it was different."

"Have you ever had an orgasm at the same time as him? Has he ever come anywhere else other than in your.." And here I paused and deliberately selected my words, "other than in your cunt."

Fay looked sharply at me as I spoke the words, but quickly answered, aware of the need to keep me from administering more punishments quite just yet. "Yes, but not very often. He has cum onto my breasts a couple of times, and I have let him cum onto my bottom too. Erm, and once he tried to cum in my mouth but it went onto my cheeks instead... is that what you mean?"

I nodded, interested in that latter information as I could tell it wasn't something that Fay had done very often. I was thinking it might be something we could change shortly. But for now, I wanted more squirming, more sexy talk from this horny lady. Even more, I wanted to see a little more of what was on offer to me.

"Good, but I want to know something you may have never spoken about with anyone, even close girl friends. I want you to describe your hottest, naughtiest, kinkiest fantasy, the one you almost dare not let yourself think about. You can think what you are going to tell me whilst you take off your blouse and skirt, we won't be needing them for a while. Do not move your knickers from where they are, I need them later."

Fay stood up immediately, and reached to undo the zip on her skirt. Slowly she shimmied the skirt down and stepped out of it, revealing her neatly trimmed pubic triangle and a glimpse of already parting sex lips. She left her red knickers at the top of her thighs, and undid the blouse buttons, easing it off and dropping it alongside the skirt. Her firm breasts were lifted up by the matching silky red bra, nipples erect through the fabric and giving away how aroused she had become already.

She sat back down, aware that she had been stood a while and had taken enough time to think what she was going to say.

"I think the kinkiest thing I fantasise about is.. well, I would be dressed in really kinky clothes, I think rubber." She paused, blushing furiously as she spoke about this, possibly for the first time.

"I think, a rubber dress, rubber underwear and very high heeled ankle boots. I think I would be wearing stockings," she went on, still red-faced, breathing a little harder and yet beginning to warm to her task.

"I am tied up, I think my legs are spread... a bar between my ankles... and my arms are spread and tied in front of me. I am blindfolded without warning, and... well, and you now have me at your whim. Its you that is in this fantasy, and you have complete access to whatever you want, and I cannot stop you.."

"So, what do I do, what do I touch, how does this play out in your mind when you are alone and thinking about it?" I asked, reaching forward to stroke a nipple through the silky fabric of her bra.

"Well,... you, you... oh, you stroke me all over, rubbing my body through my clothing but I never know which bit you are going to play with next.. You run your hands up my legs, under the rubber skirt and on to the top of my thigh. Your hands feel silky and smooth as if there is some oil or lotion on them. You are teasing me, and your hands leave my legs and it goes quiet. Suddenly something is nudging gently at my lips and I open them instinctively. You push your.. the... your thing..."

"My what, say it, use the language that suits the mood, the situation, what do you mean?"

Fay met my eye, turning a little pink in the cheeks as she realised what was happening, she was being forced into more mental pain than physical. "Your cock. You push your hard cock between my lips and I have to lick it and suck it. You hold my head so I can't back off, and I start to enjoy the feeling of your .. your cock in my mouth. It seems to be getting bigger and you push it to the back of my throat, almost gagging me, before taking it out".

Fay stops, seems to think a little more, then carries on, ".. and then my skirt is peeled back exposing my bottom. My legs can't be closed and I am aware that you will be looking right at my rubber covered bum cheeks. You take the rubber panties down a little and ... well, my bottom is visible to you".

"Bottom, bum? Tell me what words you think I would be using now if I were talking about what I could see, and what I was going to do. Tell me what happens next, the state of your ass, tits and thighs depend on it.."

Fay seemed to take a breath and sit up straighter, she was now realising she could not avoid using the sort of smutty, horny language normally reserved for consenting adults behind closed doors, or porn films and Literotica stories.

"From behind you can see my ass, my anus, and when you pull and stretch the rubber knickers further there is your first sight of my pussy lips. I don't know what is happening, but I feel as something slips into my pussy... a finger, possibly two, as it feels full and I start to get wet. My pussy is juicy and I feel you fill it up even more, perhaps that is three fingers and I am writhing a little now. My nipple is pinched without warning, through the rubber of the tight dress, and I yell. The fingers are removed and there is nothing, then I feel a hard smack on my bare ass and you tell me there will be more if I make noise. You slide hands now all over my legs in their stockings, and pull at my nipples in my rubber dress. I can't see what you are doing until I feel something touch my pussy lips. It pushes in, and I know its your cock, its bigger and harder and it slowly invades my pussy and vagina. I can't help it, I moan with pleasure and am rewarded with a smack on the other cheek even as you slide your cock further in. You pound me, I cannot move, my legs are wide and spread and my hands are tied. You shove harder and harder into my..." and Fay pauses, looks directly at me before saying, "my cunt. I am wet, my cunt is dripping with my juices and the situation is so horny I cum hard, quickly and without you cumming. You smack my ass cheeks as you pound away and I feel you tense before you cock empties spurt after spurt into me.. your cum fills me up before you slip out and leave me. I feel it leak out and onto my thighs... and then something nudges at my lips. You push your softening cock to me and I am forced to take it and suck it clean".

I watched Fay carefully as she related this. Sometimes she paused but only for a second or two to get the idea clear in her mind. I noticed she got more explicit as the story went on, and she settled into her fantasy, possibly even reliving it as she told it. I could see her squirming, though I doubt she realised it, but I knew she was getting excited as I could see the wetness of her cunt lips grinding onto the chair. I was hard inside my jeans, and I knew I would want to use this to keep Fay on her toes.