Rehabilition of Margaret Jenkins

"Thank you Eric, you explain the situation nicely. Margaret, I've been hoping that we can help you. I am perfectly willing to do what I can for you to discover if there is any reason to advise you against anal sex, to be honest I don't imagine there would be. More important for you, whether it is likely to be satisfying for you and your partner. The only way to find out is for us to try it. Yes, you and me.

When I am assisting Eric with a patient, as I am most days, my involvement is fairly anonymous. Nothing wrong with that, it doesn't belittle me, in fact I like it that way and it is quite liberating for both of us. The patient can speak or display things they might be uncomfortable about with their doctor. I put myself at their disposal regarding their needs, which might involve emotional or physical solace. They might want me to hold their hand, they might want to flirt, they might want to touch me through my uniform. I have no problem with that, within reason. Had I not been away yesterday I would have been looking after you during the enema and afterwards. I would have agreed your request for anal sex straight off."

I was quite astonished. Here was this young nurse coming right out and saying it would be fine for her to test my affinity for anal sex even though she didn't agree it would be right for the doctor. After a few moments thought, I realised she was perfectly correct, at least if she didn't have any personal issues with doing such a thing. Perhaps she already had with other clients.

But I was still rather nonplussed. Of course, she could fuck my ass with a dildo or something similar and that would be enough to know how I would feel, but not how a man would feel. Only a live cock would suffice. I still didn't want Jim to have anal sex with me and not find it satisfying. I'd sooner that I didn't enjoy it but he did. I looked at Eric who was clearly paying attention, but his expression wasn't giving anything away. Nor was Natasha's. However, she continued, "Why don't we try it. If you agree, at least you'll know how it is for you, and I think I can make a decent judgment as to whether your partner is likely to. Can you go with me on that, Margaret? From your records I don't think you have a dislike of intimacy with a girl."

There was nothing I could reasonably argue with.

"OK, I'm game."

Eric told me that he normally left Natasha to provide TLC to his patients as she didn't need any help from him, and suggested the two of us adjourn to somewhere suitably private while he relaxes downstairs in the company of the TV and what was in the kitchen.

Natasha and I went upstairs and I showed her into my bedroom. She was clearly impressed.

"Hey, what a lovely big room. All those fitted closets and you have a king size as well, what more could a gal want?"

"Yeah, I like it. It would be even better with someone to share it with."

She seemed really excited by it and took my hand in hers as I pointed out the furnishings. Her hand was warm and she leaned in against me, the way someone would when sharing a confidence with a close friend.

Now the time had come, I suddenly felt tongue-tied and unsure how to talk about the business. I was still collecting my thoughts when she went on, "I don't have my uniform to act like the nurse, so why don't we both get undressed?"

With that she pulled her shirt from where it was tucked into her jeans and started to unbutton it. I did what was obvious which was to unzip my dress and let it fall onto the floor. Now devoid of any covering I felt a bit more brazen and stood flaunting my body as I stood before her with my legs slightly apart and my hands behind my head. I knew I wasn't a film star, never had been, but I felt I had aged fairly well.

"I hope you don't mind seeing an old lady with her sagging breasts and her hairy pits and cunt."

Natasha stopped and stood, open mouthed, for several moments with her shirt off and her jeans down around her knees. As I suspected she was braless, in fact her small breasts and delicate nipples were almost childlike, rather as if they stopped developing in the middle of puberty. I'd expected to see a sexy little thong, but instead she was wearing black full-cut knickers of thick stretchy material. More or less a control garment which seemed illogical on a young woman, especially one with such a trim figure. Nude, she confirmed my suspicions that she had been an athlete or a dancer.

"You hope I don't mind? Wow Margaret, you look great, I always like to see a woman with body hair. And I hope I'll look half as good when I'm your age, I wish I looked that good now. Your tits and nips are to die for, not like my little things."

It was obvious and blatant flattery, but I enjoyed hearing it anyway.

"Natasha, you're much too kind. I would have killed to have your figure!"

She finished removing her jeans but kept her panties on. To my surprise she took my hands in hers and kissed them, then stroked my armpit hair. My pits are sensitive and my thoughts drifted in the direction of seeing her totally undressed.

"How about we get on the bed for you to penetr ..... I mean ... " Again it was difficult for me to find the words.

"... you mean for me to fuck your ass?"

"Yes, for you to fuck my ass. On the bed, like lovers."

Superfluously, and rather stupidly, I added, "Have you got something to use, dildo or something."

I went to the bed and pulled away the duvet to uncover the large expanse of white cotton, freshly laundered. My mind must have been wandering while I did that, because the next thing I saw was she had taken something from her bag and was holding it against her panty-covered crotch so her "cock" stuck out proud. It seemed to make her look bigger and more assertive and I stared at it, transfixed. Such a simple object, but mighty in its connotation, a flesh-coloured rubber phallus. It looked big against her petite figure, but wasn't really. I guessed hardly any larger than Jim's or Eric's, but its shape and contouring were realistic. I was sure it would feel nice in either my ass, and in my cunt for that matter. I wasn't sure if I'd want to suck it though.

She twisted and stroked it, traced a fingertip along its length, circled the head and spiralling in towards the hole. I imagined a man doing similar with his real thing. It seemed strange that the size didn't change.

"Touch it, Margaret. Tell me if it's what you like me to fuck you with. Think about how it would feel up your ass, pistoning in and out, stretching your ring, making you squirm."

As if on automatic, I reached down and stroked, twisted and squeezed it. It was the right colour, size and shape, good flexibility. But I couldn't help being disappointed that it didn't grow in my hand, and no drop of sticky fluid appeared at the tip where the hole should be. No life though. I didn't say anything but Natasha must have sensed my disappointment.

"No, it's not the same as the real thing. Isn't that what you want Margaret, a real cock?"

Of course that's what I wanted. I remained silent, just nodded. Natasha let it drop to the floor.

"I can still use it on you if it is what you want. In any case I first need to feel your entrance and inside with my fingers, the way Eric did earlier. He told me what your anus and sphincter were like, so I already have some idea, but I have to do it myself to properly get a feel for how your ass responds, and how gently or ungently I should take you. Are you OK with that Margaret?"

"Yes, I'm OK with whatever you do."

Natasha directed me to go on my elbows and knees in the middle facing the headboard, and raise my butt as much as I could. She took a pair of white latex gloves and the lube from her bag and I thought she would immediately make for the dark valley between my cheeks and home in on my rosebud. Instead, she knelt behind me with her legs between mine and leant forward so our bodies were touching, her girly little boobs against my back. It was heavenly. She then feathered her hands very softly over my body, starting with my flanks, my legs, then my belly and my breasts. Fingertips teased my nipples, the touch very light and slow, making them stiffen. A perverse little part of me wanted her to pinch them, pinch them hard, hurt them, but she desisted. I hoped she would move down to my crotch and explore my swelling labia, and the wet slit between, but I suppose she gauged I was already suitably aroused. Probably as well, I would probably have orgasmed.

"I'm going to start on your ass now, Margaret, and will be using plenty of gel and going inside. Do you want to put a towel down under you so the sheet doesn't get soiled?"

I said I preferred to feel the cotton sheet directly on my skin and didn't mind if it got dirty. There was a mattress protector as well so it wouldn't be a problem.

She donned the gloves and gently prised my cheeks apart.

"Good, hardly any sign of the exam and enema. To begin with just relax and don't try to clench or squeeze."

I heard a squishing as she lubed her fingers, it sounded as if she was using a generous amount. Next thing I felt a finger tracing along the bottom of my cleft, stop and spiral in towards my anus and slowly penetrate through my outer sphincter. She performed exactly the same movements as doctor Eric had done, but the touch felt more sensitive.

I yielded to the finger's invasion as if welcoming a friend. Then another. I couldn't sense the depth of her fingers, but they weren't as long or thick as Eric's so they wouldn't fill me as deep in my rectum.

"I can feel the walls of your bowel, they are in great condition, smooth and elastic. You obviously follow a good diet. There's not very much shit, just a little, not enough to make you feel you should have gone to the bathroom. There won't be much mess when I pull out."

That was a relief, not that I would have minded but I would have been ashamed to have her fingers in my bowel when was full with stool, she probably would think I was really gross.

"I have two fingers in you now. Your sphincter is a bit loose, it goes that way as you get older but also Eric tells me yours was dilated a lot when you were younger. Before I put a third inside you, I want you to squeeze as tight as you can, like with the doctor."

I tried to do as she said, but didn't feel as if I was applying much force. I tried when she used three fingers, and again with four, each time felt more reaction. I said as much to Natasha.

"OK, that's not surprising. My fingers are smaller so you won't feel so much, but from what Eric said I think it's the same as a couple of days ago. Fingers are not the same as a cock, apart from anything else the profile of finger doesn't allow for as good a contact. I cannot honestly say how satisfying it will be for your friend but I expect he'll enjoy the experience. But how was it for you, Margaret?"

"Well, with one or two of your fingers I didn't feel much, it was pleasant but not really stimulating. It was better with three, and four I really felt a nice stretch which was quite satisfying to squeeze down on. Are you going to put any more in?"

"No, if I tried it would stretch you too much when my knuckles went through your ring. So you have to be satisfied with just four fingers. It is about average for an erect large penis, but not the same profile. A cock would feel better for you and obviously also for its owner. Would you like that, Margaret?"

I had to admit I would like it, but I was sure Eric meant what he said. Oh well, I was sure Natasha's strap-on would be quite pleasurable.

More in hope than belief, the thought crossed my mind that Natasha might not be quite what she seemed. The thought excited me. If true, it would be consistent with her androgynous body type and girlish breasts, but surely too farfetched to be likely. Wishful thinking really.

"Yes I would, but I'm sure I'll be content with whatever you do to me using the rubber cock."

"OK, it's time to put it on. Please get off the bed now and help me with it."

I wasn't at all sure why she needed my help but I was in a totally unfamiliar situation so I did as she asked. I still couldn't understand as she knelt down and had me step into the leg loops of the harness and brought it up to my groin. This must be some kind of joke, I thought, and it was confirmed by her next words.

"First I want to see how it looks on you Margaret."

She then held the delta-shaped panel where the "cock" sticks out against my pubic triangle.

".... OK that's looks about right ...."

Puzzled I continued to follow her bizarre requests.

".... now reach behind and fasten the belt around your waist so it doesn't flop about but not so tight as to be uncomfortable ... Hey, it looks good. Now work it into place so it feels good on you and adjust the fastening of the leg loops."

It seems as if she was intending that I was the one to use the strap-on, and the receiver could only be Natasha. Did she need me to use it on her in order to get in me in the mood to be ass fucked? Or to get her in the mood? And why did she still keep her knickers on? I don't know why I carried on with this crazy game, I suppose that despite everything I was fascinated to find out where all this was leading. I fiddled around with the tension in the straps and loops and then worked the pubic panel until it was nicely against mine and felt comfortable. I couldn't resist holding it gently in my hand and giving it a few tentative strokes, as if I was a man about to masturbate. I felt very naughty and excited, especially as Natasha was staring at it with what looked like a longing in her eyes.

She handed me the gel, "Looks lovely on you, lube it up for me."

With that she pushed down her knickers. It was all I could do not to faint Instead of a sweet little slit, all I could see was something between her legs and covered over with flesh-coloured tape, making it appear as a little bump. It could only be a penis tucked and taped. It looked small and was obviously flaccid. I couldn't judge its size or her ball-sac under the tape. I stared at it, trying to visualise it engorged and hard, and wondering what it was going to feel like inside me. I was looking forward to the anal penetration, but I wanted it in my cunt as well.

"I wasn't sure how to tell you that I'm not a biological girl. I hope you're not upset. I can still use the strap-on to fuck you, but you did say you'd prefer a real cock.

As you see I am not ready just now, I mean it is not ready. I have to be like this when I'm with anyone, especially attending to a patient. So I need you to get it in the proper state. Hard but not let me cum. Can you, will you?

It's best if I go against the bed and you take my ass from behind, and stroke me at the same time."

It was a request I couldn't refuse, nor wanted to. Natasha was putting herself in the sort of sub situation I'd been in so many times with my daughter Lauren and her dyke friends. I'd try to be gentler and more loving than some of them had with me.

"Yes, I'd love to do that."

Natasha knew the drill and leaned forward with her hands on the bed and her legs spread.

"I'm ready. Please untape me first."

I didn't want to hurt her, and was very tentative as I nervously and awkwardly eased the tape away to free her genitals. I gently manipulated them in my hands to unfurl them from the cramped, tucked up configuration. Immediately her cock looked bigger, even though it was as yet still flaccid. I continued to fondle and stroke gently and her flesh grew, as if by some miracle of Nature. Fortunately, she didn't mind my clumsiness.

"Mmmmmm, it's nice to feel a woman's hands on me. And thank you for paying attention first to where it was most urgently needed. I'm ready for your cock now, Margaret. You don't need to be gentle, just make sure you reach my prostate. I don't mind if you're rough with me, I'm well used to that. Don't worry about how well you think you're doing it, I'm sure it will be good."

I kept one hand on her bits and with the other parted her buttocks and ran my finger along her secret valley. I knelt and pushed my face in there and sniffed the rich aroma, a mix of sweat, male scent, and the earthy bitterness that could only have originated from within. I found her hole, surprised at its size and compliance. I was sure some large instruments had penetrated her, and not gently either. I resumed my position for doing the business.

I explored her valley with my "cock" until I found her hole with the tip, resting it for a moment right at the entrance. I tried to be positive, but couldn't bring myself to be rough, indeed I didn't feel I should. But as I entered smoothly, feeling no resistance as I pushed through her sphincter until the end of my shaft encountered the membrane behind which lay her prostate, the G-spot.

"Yes!!!!!!!!!!!! That's the spot. If you just draw back a tiny bit and push there again. Keep it pulsing .... yes. Like that ...... Mmmmmmm, that's lovely. You're doing it just right ...."

I stroked her penis, using some gel to help its awakening, and felt it swell and harden in my hand. It was not particularly long, but thick for its length. I would certainly feel it. Her whole body became agitated as her arousal mounted.

"Wow Margaret, you'll have to stop now or I'll cum. My body doesn't want you to stop but I need still be hard when I do it to you. Time we changed places."

I was slightly sorry because I so much wanted to give her pleasure, and almost immediately had to stop. But I was very aroused and I wanted her cock in my ass.

"Yes, I can feel you are ready to fuck me now. And I'm ready to take it."

Quickly we swapped places to keep the mood going. I got into position against the bed and spread my legs.

A pair of legs filled the space between and her hands pulled my buttocks apart. Her cock found its target immediately and its tip rested just inside the rim, but not yet pushing through. Her hands swept across my back, round my sides and caressed my breasts. The circling of my nipples made then instantly hard and yet more as she stroked and then pinched them between her fingertips. I felt the rising arousal in my core while my pussy automatically moistened. Suddenly a finger slipped along the wet groove between my labia. I was close to orgasm and would have done so had not it moved away almost as quickly as it arrived.

"Not yet dear Margaret. I'll go slowly, the sight of my cock and how it felt in your hand won't have prepared you for how it will feel when it enters your ass. Please say if it hurts"

I knew it would stretch me, having already handled it to full size and hardness. But feeling the object begin its slow but inexorable push through my ring had to be experienced to be truly appreciated. I willed myself to relax and welcome the intruder. I admitted to myself that it felt bigger than I was expecting, and harder too than when it was in my in my hand. It certainly did hurt a bit, but it was a hurt I wanted.

"It's fine Natasha, fuck me with your hard cock. I want to feel it going in and out. And I want you to enjoy doing it."

I don't know how I would have reacted if she really had shoved it in. She just continued her slow push, gradually widening my channel, but even so it was quite something.

"Nnnnngggghhh" I grunted through clenched teeth. I realised I had involuntarily clenched.

"Shhh Margaret, just relax."

I forced myself to yield and my ring opened to allow the crown to push past my muscle. I felt the easing of force after the ridge went through, then a steady invasion as the shaft penetrated deep into my rectum. It felt very stiff, and the contours slightly knobbly, and veined. She held it still for a while, letting me get used to it, and made soothing, comforting sounds, the way a mother does to her young child when he or she is hurt. The pain lessened, then disappeared to be replaced by pleasure. I wanted more, I wanted her to piston it in and out.