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  • Alan And The Doctor Ch. 03

Alan And The Doctor Ch. 03

12

That night Alan is allowed to choose any of Lyndsay's outfits and underwear. Lyndsay has bought him a pair of size 8 high heeled shoes from a fetish shop. Once he's put on the suspender belt and dark stockings he slips his feet into them and finds that they fit him perfectly. A pair of pink frilly panties follow and even before he'd got into the black miniskirt and white semi-seethrough blouse his penis is as stiff as a poker. Lyndsay looks at her husband and can't help admitting to herself that he is well on the way to looking very feminine. She adds the wig and makeup and the transformation is complete.

"Oh Alice," she says. "You look gorgeous. I'm convinced you'd pass as a woman if we had a night out together. Are you willing to take the next step? I'll get your ears pierced tomorrow and we'll find you a more expensive wig."

"No Lyndsay, I couldn't do that. What if we met one of my mates or some of your friends. They'd pretty soon work it out. Let's just confine it to the bedroom if you don't mind." Alice says.

"Okay sweetie, but I can see how excited it gets you." She moves her hand up Alice's skirt and gives her cock a tug. "Your little willy seems to like the idea. Maybe we could have a couple of nights away in another town. It'd be such fun don't you think?"

"You always said I was big down there. I was always your big boy. Now every time you mention it you're describing it as small or little." Alice says. "I always thought of myself as average sized."

"Sorry dear but maybe it's gone a bit smaller lately. I know I shouldn't but I keep comparing it with the vibrator you bought me." She says pulling the strap on out of her bedside drawer. "Anyway that darling man the doctor won't let you use your cocky wocky on me will he? I'll have to make do with this for now. Strap it on sweetie, I'm already hot for you. I won't need any foreplay tonight, just shove it straight up."

Alice slips the panties down and straps on the 8 incher adjusting it so it's above her own penis.

"Hang on a sec," Lyndsay says. "I've just had a thought, just you lay back on the bed and I'll straddle you, good girl."

Lyndsay quickly lowers herself down on the rubber penis facing away from Alice and begins bouncing up and down on it, at the same time stroking her clitoris with her fingers. She's pulled her nightie over her head and is completely naked. Alice is not getting much sensation herself and feels a bit humiliated. Her cock is still hard, so she reaches down and strokes it, rather awkwardly as her thumb comes into contact with Lyndsay's bum each time she comes down against her body.

"Move your hand out of the way sweetie, I want to feel the whole length in my cunt. Mmmm, it's getting to parts of me a cock has never been before. I love it. It's not quite as nice as a real cock but I like this position. I can pretend I'm fucking with somebody else. You don't mind do you?"

Alice accepts she's not in control and being submissive seems fitting whilst she's dressed en femme.

"It's okay dear I really don't mind. I expect you're thinking of Sue are you? She fucked you with this didn't she?" she says.

"No it's a man I'm thinking of." Lyndsay says panting with the exertion but now into a delicious rhythm. "Some women imagine it's George Clooney but I like to fantasise about somebody a bit closer to home, you know, somebody we both know. It works for me. I always was a dirty girl wasn't I?"

"I know you were pretty wild before you met me but you've been faithful since we met right?"

Alice is thinking about the stories and videos she looked at earlier. She realises she wants to hear some kind of revelation from Lyndsay despite knowing how upset it will make her. What's happening to me? she wonders.

"You must know I'd never go behind your back sweetie. I've often been tempted, many times in fact, but I've never done anything naughty unless you'd count my regular checkups at the doctor's." Lyndsay says, slowing her movements. She's decided this is a good time to tell her en femme husband about it, she's interested to see her reaction.

"So you liked Dr Greenbank then?" Alice says, already feeling signs of more arousal.

"Oh yes. Our old doctor was very dishy and doctors are allowed to take liberties with their patients aren't they? I'd go and see him on any pretext I could think of and insist on a full examination. I loved to strip off for him and feel his hands on my body. He must have realised what I was up to but he was always polite and professional. My nipples would stand out as he checked my breasts and I was always well lubricated down below. I enjoyed seeing the bulge in his trousers each time. The examination always took a lot longer than was necessary. You're not mad at me are you dear? Should I have let you know?"

Lyndsay climbs off Alice, turns around to face her then impales herself on the phallus again. Her knees push between Alice's legs. Alice is happy to open them to accommodate her. Lyndsay uses her knees to force her legs even wider and begins kissing her face and lips as she pushes and pulls herself in and out of the 8 inch cock effectively fucking Alice like a man as she lays there passively on the bed. Lyndsay sets up a furious rhythm, gasping and moaning until her orgasm comes and she flops on top of Alice exhausted.

"That was really lovely." Lyndsay says, rolling next to Alice on the bed. She looks across at the real penis still standing up partly hidden by the strap on. "Oh, you poor dear. You didn't come did you?"

"Don't worry I'm fine. I liked your little story about Dr Greenbank." Alice says shyly. She blushes a little and her penis pulses.

Lyndsay takes the penis in her hand and begins to stroke it. "There's a little bit more, dear. Dr Newman gave me a full examination when I saw him that first time. You'd like to hear about that wouldn't you my little sweetie pie?"

"Yes." Alice says, her voice almost inaudible.

"I wore my stockings and suspenders for him and my sexiest underwear. He didn't stop me when I did a slow seductive strip right in front of him. I kept the stockings on whilst he examined me and although he was pretending indifference, his bulge was obvious. He took his time checking my breasts. When the back of his hand lightly grazed one of my nipples I was so turned on I jumped slightly. I was already very flushy and was so excited that I "happened" there and then. I expect that the doctor noticed but he pretended not to. He got me to bend over so that he could have a look at my bum hole and then examined me around my cunt area. It was so nice to feel his finger explore my vagina. He was very thorough sweetie. Afterwards I was still feeling very squishy so I visited the surgery toilet and fingered myself to another satisfying orgasm."

Lyndsay had continued stroking Alice's penis as she talked but had stopped each time Alice seemed on the verge of ejaculating. For her part Alice was almost drowning in feelings of intense humiliation but, at the same, aroused beyond her previous imaginings until, near the end, she spurted without any help from Lyndsay's fingers whatsoever.

"Oh Alice darling, I can see you enjoyed that. Does it excite you to think of Teddy fingering my cunt?"

"Yes." Again Alice's answer is almost inaudible.

"Okay,sweetie. Maybe we could spice up our love making if we play a little game. Why not let's pretend that our strap on is Doctor Newman's cock. I could talk to you whilst we're fucking and tell you how much I'm enjoying getting a good rodgering from the doctor and you'd find that a big turn on wouldn't you, dear?"

Alice is not sure how to answer this. Lindsay's right, for some reason it would turn her on. In fact she realises that, for the future, her most powerful masturbation fantasy will be imagining Lyndsay getting intimate with Dr Newman. Perhaps she could wear her pretty clothes and bring them tea or alcoholic drinks. She frowns and suddenly gets frightened. She's about to say a definite 'No' but starts to speak then surprises herself by what comes out.

"It's his cock you really want not some rubber imitation isn't it?" Alice says taking the wig off and beginning to remove her feminine outfit. She's turning back into Alan again. "It's okay Lyndsay, you've more or less admitted it haven't you? I'm worried that you've fallen in love with him and I'm going to lose you. He's a real man and I've just found out that I'm an effeminate crossdresser."

Lyndsay didn't expect this. Alan has not been the type in the past to be this articulate about sexual relationships. Suddenly she's regretting getting drawn into the doctor's devious scheme. She doesn't know how to respond but decides to be as honest as she can in the circumstances.

Alan has removed his dress and suspender belt and stockings and is pulling on a pair of tracksuit bottoms. He's left the panties on the floor.

"You're quite right Alan. I am strongly attracted to the doctor. He's a lovely man who seems to possess a stronger sex drive than you do. He's probably capable of satisfying my sexual needs. You're my husband and I don't want to change that. I love you and want to stay with you whether you are cross dressing or not cross dressing. I'll never leave you no matter what. I think you know that I always check with you to get permission to do anything before I do it. Remember me ringing you at work about going to meet Sue? Well it's the same with the doctor. It's just sex, nothing else, I'd like to fuck him but if you say I can't that's absolutely fine. But I won't promise not to fantasise about him." Lyndsay finishes this long speech with a smile and makes eye contact with Alan.

"I get it. You've taken a weight off my mind. So you could live with yourself having those sexy visits to see the doctor. You didn't see them as being unfaithful to me?" Alan says. Lyndsay nods. "I'm okay with that. Tell me was Dr Newman the man you were thinking about just now when you were bouncing on the strap on?" Alan's more relaxed now and smiles back at Lyndsay.

"Yes, I was." Lyndsay says.

Alan feels his penis stir. "There's something about that man, I don't know what it is, if I was going to allow you to break your marriage vows with somebody it would probably be him. My cock wants it to happen but let's just leave it as a fantasy for now. I'll give you my answer soon."

Lyndsay accepts this, hoping for permission soon. She's glad it's out in the open at last. She's had an idea but isn't sure how she's going to make it work. She takes Alan to get his ears pierced. There's further sexual play over the next few nights. Alan's still enjoying becoming Alice. His breasts have increased in size and Lyndsay has had to buy him a larger bra. He loves his new tits and his nipples have become very sensitive. He's also getting used to wearing the strap on. It doesn't always feel all that satisfying for him, it's more about satisfying Lyndsay. Lyndsay realises she's being a bit selfish and manoeuvres him into the sixty-nine position after she's had her orgasm sucking on the real cock whilst Alice buries her head between Lyndsay's legs. Alice soon spurts and it sometimes leads to Lyndsay "happening" a second time.

A few days later Lyndsay telephones her sex shop friend Sue for advice about taking Alice out of the house en femme. This leads to research on the internet where Lyndsay finds what she wants.

"I've booked us into a small hotel on Saturday night sweetie." Lyndsay tells Alan over breakfast. "I thought we could use a bit of a break."

"That's fine dear. Where are you taking me?" Alan quite likes it when Lyndsay takes charge. He's really a submissive by nature.

"It's in a small town called Grassington in the Yorkshire Dales. We can go for a walk in the afternoon and they're putting something special on in the evening. I'm sure you'll like it." Lyndsay says.

Alan's never been to Yorkshire but is happy to give it a try. He notices that Lyndsay has put her stuff into their suitcase and left him to put his things into a small overnight bag. She always seems to need more than him when they're away so he thinks no more about it. They arrive at the hotel at lunchtime. Lyndsay opens the suitcase and he sees the high heeled shoes he wears in the bedroom and other items he likes to put on when he's en femme.

"When we go down to dinner tonight I want you to be Alice for me. You'll be in good company. The husbands that are staying tonight are all cross dressers and they'll be wearing their finery. The hotel have put on a party for us all afterwards. It will give you a chance to meet others like yourself. You'll be in a safe environment. We've got exclusive use of the hotel. We'll have a nice walk in Wharfedale dressed as you are now. It'll give you time to get used to the idea of what is to come. Don't look so shocked, you'll be fine. You'd be surprised how many clubs and organisations on the internet go in for this kind of thing." Lyndsay says.

Alan is shocked. He could refuse to go along with it but doesn't want to hurt Lyndsay's feelings. As they explore the area on foot in the afternoon he tries but fails to imagine what the evening will be like. He's never even thought about wearing women's clothes in a public place. He's not keen on the idea but willing to do it for Lyndsay.

He wears one of Lyndsay's low cut dresses and a sexy bra to show off his larger breasts.

"Be sure to bend from the waist dear to give them a glimpse of nipple if you're flirting with anyone tonight." Lyndsay says.

"What do you mean flirting? You know I never flirt." Alan says surprised.

"You'll see. The other girly men will be bowled over when they see how attractive you are. You've never spent time with a bunch of cross dressers before. I want you to enjoy yourself sweetie." Lyndsay says. "I've decided to let you off the leash."

"I've never been attracted to men. You know that." Alan says.

"Ah, but once you've had a drink or two you're not going to be worried about what they've got between their legs. Trust me." Lyndsay says.

Alan doesn't reply but his wife's comments stay in his mind as he is transformed into Alice again. The new wig, subtle eyeshadow and red nail polish really do make a difference and as Alice looks at herself in the full length mirror she realises that she really could pass as a woman.

"Which toilet will I be using?" She asks, suddenly feeling a bit scared.

"The Ladie's toilet of course. Don't worry sweetie we'll always go together. Then we can have a girly chat about all the other guests. Aren't you excited dear?" Lyndsay gives Alice a quick hug seeing the fearful expression on her face.

"Yes, sort of." Alice says and they go downstairs to the hotel dining room.

A waiter shows them to their table. They find they have a card on each of their place settings, showing 'Alice' and 'Lyndsay'. They are on a table with two other couples. All the couples are women. Looking around Alice finds it difficult to tell who is the generic woman in the relationship but if she was guessing she would plump for the slightly more dowdy partner, not quite as much makeup, not quite as sparkly earrings and other jewellery. It dawns on her that in many cases what she thinks of as the generic woman is the least sexy looking of the two and smiles. She's beginning to relax.

Alice turns her attention to the four other women sitting at their table. She notices that there's a disparity in ages with one of the couples. Lyndsay has noticed too and breaks the silence at the table.

"This is our first time so we are a bit nervous." She looks towards Alice. "Alice has never been outside our bedroom before en femme so you can probably imagine what she's going through at the moment. I'm Lyndsay, Alice's wife.

"

The older woman speaks first. "Hello Lyndsay and Alice, you are not the only first timers. I think they might have put us all on the same table. Susan here has wanted to come along to something like this for a long time. She's single. They insisted that it was strictly couples only so she persuaded me to come along. I'm Jane her mother. She still lives at home with me."

"Yes, we're first timers too. I'm Hazel. This is my younger sister Tracey." Alice assumes that it's the generic woman who has spoken again. She looks Tracey in the eye and smiles warmly. Despite her earlier misgivings she senses a connection with her. She's a bit younger than Alice but extremely attractive. She looks quite relaxed and gives Alice an impish wink.

Alice and Tracey are sat next to each other and they chat amicably throughout the meal. Alice finds she is enjoying herself. She notices that Lyndsay and Hazel, Tracey's sister, are also getting on well. Jane keeps asking questions. Susan is keeping quiet. Jane's curious to know how Lyndsay can get along so well with a husband who wants to dress as a woman.

"She's only been Alice for a short time," Lyndsay says. "To tell you the truth it was me who got her dressing up. I find it quite a turn on. I can tell she likes it though, don't you darling?"

"Yes, my doctor asked me to start wearing panties and it's gone on from there." Alice says. "It seemed a strange suggestion at the time but I'm glad he said it." She turns to Tracey. "How did it start with you? Sorry it's a bit personal, you don't have to answer if you'd rather not."

"No problem. Me and Hazel have always been close. We've never had arguments like other siblings. We've always been able to say anything to each other and share secrets. I was always a bit effeminate and interested in fashion and what Hazel was wearing. It just seemed natural for me to borrow some of her clothes at first. I was still at school then and people started saying I was gay so I hid it away. Hazel has supported me and advised me from the beginning. She lets me wear what she wears, does my make-up and that sort of thing. I don't think she'll mind me saying but she's had to come to terms with her own sexuality and I've supported her with that." Tracey says, looking at her sister.

"Yeah, that just about sums it up. Realising I was lesbian was difficult for me but Tracey's helped a lot. We've recently moved in together." Tracey says.

The atmosphere on the table is very relaxed and all six enjoy the meal. Each couple buy a bottle of wine at the start of the meal then a second bottle when the sweets are served. The wine is shared around and Alice drinks at least four glasses. The staff rearrange the tables when everyone has finished to allow room for dancing.

It's no great surprise to Alice when Lyndsay asks Hazel to dance. There is no band; the music comes from expensive speakers via an Ipod and it's easy for anyone who is there to choose the music they want. Alice has moved her chair a little closer to Tracey's and they chat together quietly enjoying the music. Alice notices that her dress has slid up her legs a little and decides to leave it where it is. Tracey is looking from her cleavage to her legs as they talk and Alice finds this arousing. Tracey is wearing a short, tight fitting skirt. She has good legs and Alice can't take her eyes off them. Tracey has noticed her staring and shifts in her seat showing a lot more of her stocking clad legs.

"Do you like what you see?" Tracey says. Alice looks over at Lyndsay who is holding Hazel very close as they dance around.

"Yes." Alice says. Her head is spinning with the wine. She's totally out of her comfort zone but decides to be completely honest, not knowing where things are going to lead.

"Let's try to shuffle around together to this one." Tracey says as Adele's song 'Someone like you' starts.

It's not really a song for dancing but they hold each other and move slowly and rather awkwardly around the floor. When this record finishes Alice looks at her watch and realises it's getting late. She likes Tracey but isn't sure what she wants from her. She goes over to where Lyndsay and Hazel are sitting holding hands.

12
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