Alan And The Doctor Ch. 01

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Doctor finds solution to Alan's sexual problems with wife.
3.5k words
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Part 1 of the 3 part series

Updated 06/07/2023
Created 02/08/2016
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Quietoldie
Quietoldie
1,002 Followers

Alan Slater likes his doctor and trusts him. His GP Dr Greenbank has helped him with his medical problems for twenty years. But when he goes to see him about an embarrassing personal problem he finds he has retired. His new doctor is Edward Newman. Dr Newman is a tall imposing man who immediately impresses Alan. He falls under the man's spell and Alan decides he can speak freely about his problem.

"You see doctor I'm just turned 60 and I'm finding it difficult to keep my wife happy sexually. She's 10 years younger than me and has always loved sex. She can't get enough of it doctor. What am I to do?" Alan is blushing but feels glad he's been able to confide in someone at last.

"I can see that might be a problem for someone of your age." He pauses. "There may be a way to help but it's a bit unusual. It's important that you trust me and do what I say. First of all I want you to take these pills every day and come back to see me in two weeks time. You must masturbate frequently in the meantime. Do not have sex with your wife. Tell her you are getting some help from your GP okay? I'll speak to her. She will understand. You'll need to look at these websites. They will help to arouse you when you are masturbating. At your next appointment I'll see if I can arrange some posterior stimulation. It will help with your erections."

The GP produces a lacy pair of women's panties.

Put these special underpants on, wash them at night and wear them every day for the next two weeks" Allan slips them on and his penis stiffens.

The doctor smiles. "Good boy. I can see the treatment is already working."

Alan has not been called a good boy for a long time. The doctor inspires respect. His air of authority is such that Alan is entranced. He loves hearing the compliment. He feels his cock pulse and stiffen even further. The doctor notices but makes no comment.

"Okay Alan, you can put your trousers back on. I'll see you in two weeks".

"Thank you doctor. I will do as you ask. It's so kind of you to take so much trouble."

Over the next two weeks Alan looks at the videos and reads the stories on the websites provided. They all follow a similar theme; female domination and male cross dressing. He wants to please his new doctor and be a 'good boy' so with this mindset the websites arouse him and he finds to his surprise that he can masturbate almost every other day.

Dr Newman arranges to see Lindsay, his wife a few days after his meeting with Alan. She is amused by what he tells her and agrees to fully cooperate with his plan.

He'd looked through her notes before she came in and discovered she had made lots of unnecessary visits to see Dr Greenbank over the years demanding a full thorough examination. Her previous GP explained that she was getting a sexual thrill from her visits.

"Whilst you're here I may as well examine you Mrs Slater." Dr Newman says as she arrives for her appointment.

"That will be fine doctor. But you can call me Lindsay." She starts to undress in front of him and he doesn't try to stop her. He can tell she's put on her sexiest underwear.

"Do I need to remove my stockings doctor? My panties are over the top as you can see."

Soon she's naked apart from her high heels and black stockings. He's trying to remain professional whilst fully erect under his clothing. He checks her lungs and heart deciding it would be silly to do a blood pressure test on a naked woman. He carefully examines her breasts with his hands. Her nipples become hard and she begins to pant. Her face is bright pink and, as he moves down to examine her vagina, he sees it has become swollen and red. He pushes one finger in, delighting in her wetness. She gasps opening her legs a little more. He then pulls her cheeks apart to check her anus.

"Everything seems fine Lindsay. Put your clothes back on please." She can't hide her disappointment but complies.

"As you know Alan came to see me recently asking me if I could help him. He doesn't think he can satisfy you sexually these days. I am proposing an unusual solution. I want to fuck you myself."

Lindsay's mouth drops open. "That would be fine doctor but Alan would never agree to that and I don't want to go behind his back."

"If my plan works he'll be begging me to do it before very long. With your help we can put him in the right frame of mind. I've already got him wearing panties. Please play along with it. Tell him you have fantasies about him in women's clothes. Get him to wear your things. Make it sexual play of an evening."

The doctor went on to explain other aspects of his plan.

As she was leaving he says, "Now don't forget to undermine his confidence but be subtle about it. He needs to believe that he has a small penis for this to work."

"Yes doctor and I'll register with Dr Smith down the road as you suggested. I don't want you getting struck off."

A few days later as they are getting ready for bed Lindsay makes sure she is there watching as Alan is undressing.

"You've made me hot seeing you in those panties." She says. "Let me get a better look dear." He moves closer, feeling self conscious, his cock beginning to grow bigger.

"I saw the new doctor as you know. He's lovely isn't he? How are you liking the treatment? By the looks of that little prick of yours the pills seem to be working. It's a shame you're not allowed to fuck me dear. I've often imagined you dressed in my things. Why don't you put your head between my legs, sweetie. I'd love a good tonguing down there right now."

" That's it, get your tongue inside. Don't stop. Sorry I'm a bit sticky and smelly, I've not had time to shower. I believe some men prefer their wives that way. Dirty buggers. I'll bet that Dr Newman won't go down on his wife. You're such a good little hubby aren't you dear?"

Lindsay chats away as he licks her until her orgasm builds when she stops talking and begins to moan pulling his head closer in.

"You need a reward darling for giving me such a nice orgasm. I was imagining it was Dr Newman down there. You don't mind do you?"

Alan blushes a little. He really doesn't mind, in fact her comments made his cock stiffen. He's not sure what's happening to him but at least his penis is responding well.

Lindsay smiles taking his silence as approval. She takes his cock in her hand and tugs on it. He's still in his feminine underwear and she does it through the panties.

"Dr Newman wants you to wank off doesn't he? He won't mind if I do the wanking this time will he?"

"No, I'm sure he won't mind." Alan says quietly not looking at Lindsay.

"You'll make sure to tell him won't you dear? He'll want to know everything. He's such a good man."

Alan nods, he's enjoying the feel of the panties rubbing on his cock and Lindsay's conversation.

"Would you like me to put you in some of my outfits another night at bedtime sweetie? We are about the same size aren't we? I'd love to see you all dressed up, maybe with some makeup on too. Would you like that, I know I would?"

Alan nods his head again and, as he does so, he spurts into the panties.

"Mmmm, it looks like you're keener on playing dress up than I thought. Take Dr Newman's panties off and I'll put them in the wash. I know he said to wear them every day but he suggested that mine would be just as good. You can wear those pink frilly ones tomorrow. You like those don't you sweetie?"

"Yes," Alan says reddening a little.

The next morning Lindsay takes him to a sex shop.

She gets behind the wheel and Alan finds himself meekly getting into the passenger seat. He usually drives when they are in the car together.

"Dr Newman suggested we get a vibrator dear for times when you can't get it as stiff as I like it. You can use it on me can't you or if you're away working I can play with it myself. You are okay with me masturbating aren't you? All women do it you know."

Lindsay is not showing the slightest embarrassment and Alan tries to follow her lead.

"Er, no dear, I don't mind it if you er, masturbate."

"Of course it's no real substitute for the real thing. As you know I love it when you penetrate my cunt with your stiff cock."

Alan is unable to think of a reply to this, his cock almost bursting out of the frilly knickers he's wearing.

The sales person is a woman. Lindsay recognizes her from somewhere and the woman smiles and winks knowingly. She nods with approval when they bring a very lifelike penis shaped eight inch vibrator to the till.

"I'm sure you'll be very satisfied with that one dear," she says with a leer.

"Yes, it's the one our doctor recommended." Lindsay says with a grin. "He thinks we need a bit of help."

Outside the shop Alan's confidence is low. "You didn't have to say anything to that woman. Are you determined to make me a laughing stock?"

"Sorry dear, it was only a bit of fun. It's not like I'm gonna discuss it with all my friends is it?" She pulls him in for a hug and kisses him full on the lips. "Is that better?"

He smiles and nods. She notices that she's left lipstick all over his top and bottom lips but doesn't say anything.

They wander through the shopping mall nodding to a few of their friends. Later they are in a women's clothing shop when he catches sight of himself in one of their mirrors. He quickly rubs it off.

"Hey, Lindsay, why didn't you tell me?" He says.

"To tell you the truth darling, it was making me wet. Why don't I drive you back to the house and we can try out our new sex toy?"

Back at the house Lindsay asks Alan to put the cock (as she calls it) into a large vase full of warm water. She takes off her jeans and panties then has an idea.

"Why don't you slip off those trousers sweetie so I can see your panties. It will help to get me in the mood."

"Okay, no problem." Alan says.

"Switch it on and rub it around my pubic mound. Gently please. Now press it against my clit. Mmmmm, that's nice. Now shove it into my cunt. Oh, oh, oh, this feels different from your cock. Keep pushing it in and out, sweetie." Lindsay is lying back on the sofa, her legs wide apart. She begins to moan. She's not quite getting into it due to Alan's technique but she wants him to think it's a wonderful experience for her so she fakes a loud, screaming orgasm.

"That was incredible darling, thank you so much. I love my new big cock."

Alan doesn't know what to say. His self esteem is low but for some reason seeing his wife enjoying a bigger cock is turning him on. He can't understand it. Somehow the more humiliated he feels the harder he gets.

Lindsay is racking her brains trying to remember where she has seen the shop assistant in the sex shop and then suddenly it comes to her. She'd seen her one night when she was having a night out with her friend Michelle. Michelle persuaded her to visit a gay bar. She has a number of gay friends and has told Lindsay she is bi. The sex shop assistant came over to their table, sat down and was soon flirting with Michelle. Michelle introduced her as Sue or Susan. When Michelle didn't respond to Susan's overtures she turned her attention to Lindsay. Michelle explained that her friend was straight but it didn't put Susan off. Lindsay could sense a connection with Susan but by then they'd ordered a taxi home so it didn't go anywhere. Lindsay had never spoken to Alan about it but often thought about what might have been.

Lindsay is enjoying all that is happening and can't wait to get into bed with the new doctor. Her sexual appetite has gone into overdrive so she calls into the sex shop the next day for a chat in her lunch hour. The woman prefers to be called Sue. She takes her through into the back room.

Sue smiles. "Are you here to ask for advice about that wimp of a husband of yours," she says.

"Well not exactly, although you might be able to help there too. Do you remember that Michelle told you I was straight?" Lindsay says hesitantly.

"Yeah, but I don't pay much attention to labels like that. You're curious aren't you?"

Lindsay nods, wondering if she's making a huge mistake. Sue moves forward quickly holding Lindsay by the shoulders and plants a kiss on her lips. Lindsay finds herself responding. The kiss becomes hot with tongues exchanged. They break apart by mutual agreement when they hear the bell telling them that the shop door is opening.

"If you liked that you'll be back here tonight at six o'clock when we close. Tell hubby you're working late."

Lindsay's head is all over the place but she manages a non committal nod and leaves the shop.

Back at work Lindsay is confused. She knows why she went to see Sue but hates the idea of going behind Alan's back. "If Alan agrees to me seeing Sue he might be more likely to accept me seeing the doctor in the future," she says to herself. However illogical it sounds she decides to ring him at work and put the idea to him.

Lindsay rarely phones Alan at work. He's a cleaner but subcontracts for a large firm who send him to lots of different offices around the city. Her attempts to contact him reach his answerphone but she leaves him a few messages and eventually he rings her back.

"Hi Sweetie, thanks for getting back to me." Lindsay says; she's in her office with the door closed. "I've been back to that sex shop we visited. I wanted to enquire about getting a strap on so you can put it on and fuck me if your willy isn't quite up to getting stiff the way I like it. That may be better than the vibrator don't you think?"

"Can't we talk about this back at home dear?" Alan says.

"No it's not about that. It was the same woman in the shop. She's called Sue. We got chatting and she made a move on me. Alan, I kissed her back! You're not mad at me are you?"

"No, I'm not mad at you. You never said you were attracted to women." Alan says adjusting his erection.

"Never thought I was. Sue wants to see me after work at six o'clock. She's nice. I'd like to go. Please let me. I'll tell you all about it when I get in."

"Okay, go for it. I'm working until about eight anyway." He's looking forward to hearing all about Lindsay and Sue's meeting. There's something about lesbian sex that always turns him on.

A workmate asks if he'd got through to his wife when they're enjoying a short tea break.

"Yeah, things are fine. It was just about women things, you know." Alan tells him.

Lindsay is nervous when Sue lets her into the shop. To help herself relax she asks Sue about a strap on for Alan to use on her.

"You'll need another eight incher, let's see what we've got one in stock." Sue says grinning. She finds one and picking it up takes Lindsay's hand and leads her into the back room where they kissed earlier. There's a large TV screen playing a porno movie.

They sit on a sofa watching two attractive, naked women fucking.

"You are looking a bit tense, can I get you a drink or something?" Sue asks.

"No thanks, I'll be fine." Lindsay leans towards Sue and they begin kissing. Their hands explore each other's bodies and it's not long before they have stripped off completely. Sue is fingering Lindsay's cunt when she whispers in her ear. "How would you like to test drive your new strap on. There's no extra charge."

"Oh, yes please Sue darling. I thought you'd never ask."

Lindsay lays back with her legs wide and Sue swiftly puts the artificial cock on and begins thrusting, gently at first.

"Fuck me harder Sue, I want you to be rough with me." Sue pulls out and forces Lindsay across her knees slapping her hard across her behind. She uses all her strength and the noise of the many slaps are like pistol shots.

"This is what you needed isn't it-- a thorough spanking? You've been a naughty girl haven't you?" Sue says. "Bend over the end of the sofa you slut. I want to fuck you doggy fashion."

"Yes, I have been naughty- I deserve it, playing a trick on my Alan. Fuck me harder, push your body hard against my stinging bum."

After Lindsay's noisy orgasm, Sue takes off the contraption. She grabs Lindsay by the hair and forces her between her legs. Lindsay feels so grateful to Sue it seems right to be on her knees worshipping her wet quim, making her come off.

Afterwards they lay together on the sofa still naked. Sue asks; "What was all that about? Playing a trick on Alan? You don't have to say if you don't want."

"It's okay I'll tell you. You can be my confessor." Lindsay says. "You see I've got a bit of a thing about doctors and Alan's doctor is very dishy." She explains about the cross dressing and messing with Alan's head and one or two other things.

"If he's gone along with you seeing me it's not a big step to him agreeing to you and the doctor getting it on." Sue tells her. "Good luck with it. Listen, if you want to see me again you know where I am. But you've got a lot on with Alan and the doctor so I won't worry if I don't see you for a while."

Back home again Lindsay gets something to eat and has a soak in the bath. She puts on her nightie and dressing gown and goes downstairs to where Alan is sitting watching TV.

"Switch that off sweetie. I'll tell you everything about earlier but first I want you dressed up in some of my clothes. It'll add to the excitement don't you think? Let's go upstairs and we'll have a look through my drawers and wardrobes. There'll be plenty to choose from in your size." Lindsay says.

It takes a bit of time but eventually Alan has become a woman. The wig and makeup complete the picture. Alan enjoys the feel of the stockings and suspender belt. He moves around in the bedroom getting used to the way the dress feels when it brushes his legs. He's aware of how much cooler it is around his upper thighs where there is bare flesh. It's so refreshingly different.

"We'll need to find a suitable feminine name for you, Sweetie. Do you like the sound of Alice?"

Alan in this garb wants to sound more feminine. "Yes." He manages in a slightly too high pitched voice.

"Okay Alice, come and sit down here next to me on the bed. Pull your skirt up a bit, there's a good girl. I want to play with your little cock whilst I talk. I expect you'll spurt when you hear what's happened. I'm sure Dr Newman won't mind when you explain what we've been doing."

At the mention of the doctor's name Alice feels a pleasant glow pass through her body. She reflects on what has been happening recently. It's not what she expected but she's glad she spoke to Dr Newman about her problem. Her next appointment with him is tomorrow. She wonders if he's managed to arrange for the posterior stimulation and what it entails.

Lindsay gives Alice a full account of her lesbian fling leaving out her confession of course. She's pleased that the transformation into sissy cuckold is progressing smoothly.

Quietoldie
Quietoldie
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AnonymousAnonymousover 1 year ago

us old uys really enjoy your stories. Really looking forward to hearing moe especially his femme clothes. Im wearing panties now as I read

MatureandkinkyMatureandkinkyalmost 2 years ago

5 Star !

I’m very aroused imagining being Alice , and hoping my naughty fantasies are fulfilled in the next chapters …… Mmmmmm !!!

AnonymousAnonymousover 2 years ago

a great storyteller

waiting for more

suckermansuckermanabout 7 years ago
so Good

I am so excited by the thought of being forced into being a sissy cuckold but it wouldnt be very difficult. I am already wearing panties 24/7 and have the mindset to be a sissy. Also my little clitty is only 3.5" hard and soft hardly makes a bump in my panties

AnonymousAnonymousover 7 years ago
Lucky Alan

I am so hard reading this!

I wish l was Alan.

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