Love in Middle Age

Story Info
Stanley becomes Sadie and finds mature lovers.
5.7k words
4.59
12k
7
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I think I must be the luckiest and most satisfied woman on earth. Does that sound smug? I fear it does, and I know that is one hell of a claim, but I believe I can convince you of the truth of it. I am forty-six years old and I moved into number two Riverview four years ago. Mine is the second in a row of five bungalows built sometime in the nineteen thirties for weekend fishermen. Each has a garden running down to the river and all have boathouses or landing stages. We look across the river to a row of willows, fields and a straggly wood. Just in sight from my landing stage is a rather good Italian restaurant, the 'Dolce Vita', to which, on special occasions, some of us row ourselves for a meal. After number five there is nothing on our side of the river except farmland. At the back of the houses each of us has another, smaller garden then there is an unadopted road which ends just beyond the last house in the row. In the other direction this same road takes us to our nearest village, two miles away. We are virtually in a world of our own and this is what has attracted each of the residents to come here.

I was an engineer. God knows why I chose engineering. It is such a macho profession and I have always been, in my own mind, a girl. Certainly, sexually I am entirely a gay bottom, who loves to dress as a woman and wear makeup, not, I hasten to add, at my workplace, where I was as macho as I could make myself. When I didn't marry some may have suspected I was gay but, except for the occasional snide comment, I was left alone to get on with my work. However, I hated the whole environment of my working life. I managed to find boyfriends in the clubs but nothing which lasted and nobody wanted me as a woman, only as a man who fancies other men.

Then, when I was forty-two I won the lottery, not millions and millions, but enough to give up work and live as a woman. I looked for somewhere where I could start a new life, carrying no baggage, and being myself. I made enquiries of several estate agents and Riverview seemed ideal. For one thing it is an entirely male community so I wouldn't be sussed out by women as being different from themselves. For another, I suspected that, given the ages of the other inhabitants, as described to me by the agent, a local man, it would be possible to lead as solitary a life as one wished. Of course, I hoped that I might meet a man who would want me as a woman, but it seemed unlikely. The agent assured me that, although the men might be a little shy of me, a woman, at first, they were all nice people and he didn't doubt that they would be glad to lend me a hand. When he said it he looked amused and I wondered why for a moment and then forgot about it.

I arrived in my little red Fiat just before the removal van. The men brought everything into the house and positioned the furniture where I told them. Mostly things fitted where I had expected but, as always in these situations, some things looked wrong and I should have to rearrange them as I got used to the house. I had just decided to make myself a cup of tea when the doorbell rang. It was my next-door neighbour from number one, who introduced himself as Bernard Singer. He said how nice it was to have a lady coming to live in the row and asked if I needed any help. He was a pleasant-looking man in very good shape for his age and as I sized him up I had the impression he was doing the same thing to me and I had the distinct feeling that he liked what he saw. I became rather helplessly feminine and even flirted with him a little. He responded very satisfactorily and I thought I saw the beginning of an erection in his rather baggy trousers. I thought I had better play it cool for a while, though I certainly decided that I wouldn't say no for ever if he wanted to be more intimate. However, for the time being, I expressed my thanks for his offer and promised that if I needed assistance I should come to him. I waved to him before closing the door and he went away with a big smile on his face.

Next to call was Richard Upton from number 3, eighty years old but clearly as strong as the proverbial ox. He saw me through the window trying to move a heavy dining table and without asking he came in, picked it up as if it was practically weightless and deposited it where I wanted it.

'Don't mention it, dear lady,' he said as I started effusive thanks. 'A pretty lady like you shouldn't have to do such things. You need a husband to do things like this.'

I replied that I was unmarried and gallantly he said, 'I can imagine that a lovely girl like you can pick and choose and you just haven't met the right man yet.' I came over all feminine confusion when he continued rather archly, 'Perhaps we can hope to change all that.'

His eyes twinkled at me and I cast down my own eyes in maidenly modesty. He may have been eighty years old but he still had what it takes in oodles.

I thought I was going to have the rest of the afternoon and evening to myself but after I had eaten my evening meal the doorbell rang again. When I answered it I found a strikingly handsome man, Michael, the other inhabitant of number one. I assumed that he and Bernard were an item. He said that Bernard had told him that I had arrived and he wanted to welcome me to the community. He made the same offer of help as Bernard and I had the impression that Bernard and he had discussed me as possible sexual fodder. His smile was just a little too intimate, even impertinent, so I turned on polite frigidity and he went away not quite so sure of himself.

'Sadie' I thought to myself as I prepared for bed, taking off my makeup and putting on an exquisite little nightdress whose pretty bows and ribbons made me feel entirely feminine, 'I think that at last you are going to have the fucking of your life but you need to play it so that you're in charge.'

I turned off the light and dreamt of big men.

Early the next morning I had a surprise. The sun was shining and as soon as I had made myself presentable I opened the front door to let in the fresh air. As I opened the door a man was unlatching my front gate. We looked at each other and I must have looked terrified for he said, 'Please don't be afraid. I am your neighbour from number four and I just want to welcome you and tell you a bit about the community.'

I gestured for him to come in and held the door open. As he passed me he smiled so sweetly I started to feel less anxious.

I indicated he should take a chair and he said, 'Hello, Stanley.'

'Sadie,' I replied, back on the defensive.

'Sadie,' he repeated. 'A pretty name for a pretty girl.'

It was Eric Lazenby, who had been my boss until two years earlier, when he had retired. We had always got on well, though maintaining a certain distance. He had the reputation of being aloof with everyone so I didn't feel excluded or anything of that kind.

Eric looked at me appraisingly, rather as I had often seen him inspecting a job. His expression told me that I should do very well. He smiled again.

'I always suspected you were gay too (the 'too' surprised me) but you were so stand-offish I couldn't be sure.'

I was astonished that he regarded me as standoffish but said nothing. I wondered what was coming.

'Away from work have you always lived as a woman?'

'No, I was too afraid, but now I intend to be myself. You see the real me here and now.'

'And does your life as a woman include being made love to by men?'

'I hope so but at my age I doubt it.'

He smiled again and said, 'I think I may be, in this instance, your fairy godmother, Cinderella. If you want to, you shall go to the ball.'

By this time I was perfectly composed. Eric always had the ability to put people at their ease though he could be a tyrant if he thought someone wasn't pulling his weight.

'Come on, Eric,' I said. 'What are you on about?'

He surprised me by taking my hand.

'Would you allow me to make love to you,' he asked.

'I don't know,' I stuttered.

'Do I repel you?' he asked.

I hastened to assure him that this was far from the case. Already I was taking in the strong face with its dark eyes, his shock of black hair shining with health, his broad shoulders and powerful arms and now, as he sat facing me across my living room, I saw the unusual breadth of his thighs and the shadow of a formidable cock lying along one of them.

'Far from it,' I gasped.

'I know I put the question baldly but would you think about it? It is deeply important for all of us.'

'All of whom?'

'The community in Riverside. We are all lovers of women like you. The estate agent is also when he gets the chance (his wife keeps a close eye on him). He knows our tastes and we asked him to find a woman who might be willing to become wife to one or all of us. You will obviously want to meet us before making up your mind and perhaps you will want to try each of us out as husbands. Does the idea appeal to you? If not we'll all understand, though, speaking for myself, I shall be very deeply disappointed.'

As he spoke my clitie had started to leak with the excitement of a possible future in which I should be the fuck toy of so many men. Eric was still holding my hand and he said, 'May I kiss you, Sadie?'

I blushed and said, 'Yes.'

Eric stood up and so did I. He put his arms around me and I remembered that he was a good head taller than me. (I am five feet six). He bent his head and, as his lips met mine, a tremor ran through my whole body and I knew in that moment that I was going to do as he wanted. I know it is a cliché to say that someone melts into a man's arms but the cliché exists because it describes a reality. Feminine 'I' melted into masculine 'him'. His tongue explored my mouth as his hands explored, deliciously, my body. We stood there locked together as he unzipped my dress, unhooked my bra and slid his hands into my panties, grasping and pulling apart my buttocks. Then he swept me up in his arms and carried me upstairs.

'Which room?' he asked. I pushed open my bedroom door and he laid me on the bed.

'May I fuck you?' he whispered into my ear and I said, 'Yes'.

He was out of his clothes in a moment and was licking my pussy lips. He gave me his fingers to suck before he thrust one, then two, then three into my cunt. My back arched with the delight of it and then all other delights paled before the greatest pain, followed by the greatest delight, as he pushed his cockhead through my sphincter and he entered my velvet tunnel. The whole of life became focused on his cock and my cunt as he rammed and battered his way into the depths of my womb. We shouted together as he filled me with shuddering spurts of baby batter and he made me entirely woman.

Afterwards we lay with our legs entwined and he told me he had always lusted after me when we were working together; so much so that he regularly had to go and toss off in his private lavatory. It happened so often one of his senior colleagues asked him, concernedly, if he was having problems with his waterworks. I had come over his stomach as he fucked me and he scooped up my milk and fed himself and me with it alternately. Then we kissed and he fucked me again.

I got up and made us a basic meal of scrambled eggs and toast, followed by fruit and cheese.

We sat naked and then he asked me if I would put on some pretty undies to show him. It turned out he had a thing for stockings and suspender belts and I obliged, which made him desperate to fuck me again, and so the day progressed and we entered the next night together and I was able to enjoy his balls and suck his great cock and explore the hairy forests of his chest, his groin and thighs. By our second morning together it was obvious that I was going to have a go at being the wife of a group of virile men.

I asked Eric if they had had shared a wife before. He said they had a thirty-something who, unfortunately for them, fell in love with the barman at the 'Dolce Vita' and he and she left to run a club in London. He also said that he would organise a get together for me to meet the other men that evening at his house. To prepare me he described our group. I give the list more or less as Eric gave it to me: At number one are Bernard and Michael, two bachelors aged about sixty-five, a couple who like to take a feminine third as their playmate. Number three is inhabited by Richard, an eighty-year old widower. At number four is Eric. At number five lives Peter, a former boxer, the youngest of the group.

I said faintly that I thought it sounded rather exciting.

'Good girl,' said Eric.

'I'll arrange the meeting and we can agree a time-table for you to try us all out as husbands.'

As you can imagine I made myself as attractive as I could for the gathering; my hair, my nails and everything else was as immaculate as I could make them in the time available, and I looked, I thought, decidedly fetching in a white, distinctly virginal, full length gown of silk organza. When I saw the reactions of the men (eyes on stalks, heavy breathing) I thought I had chosen well. It was interesting to see the differences between them. Richard and Peter decided within five minutes of our meeting that I was a delicate flower and it would be their business to protect me. Bernard and Michael clearly were the awkward squad and tried to claim that they should have double my time because there were two of them. Eric and the others made short work of that. Things looked as though they might turn nasty when Michael referred to Richard as 'Elephant Dick'. Richard took great exception to this.

'That is not a nick-name to be used in the presence of a lady, particularly not in the presence of so delightful a lady as Sadie.'

Peter turned to me and said, 'If either of these poncey sods tries to make you do anything you don't want tell me and I'll beat the shit out of them.'

After some masculine huffing and puffing they settled down to agreeing a schedule with me.

During this trial week I should belong to each husband from dinner time until the next mid-morning. I had been with Eric for Saturday and Sunday night. I should have Monday night to myself, then Bernard and Michael on Tuesday, Peter on Wednesday and Richard on Thursday. After that we should review the situation.

'And think on,' said Peter to Bernard and Michael, 'Sadie's a real lady. Treat her right or I'll cut your bollocks off.'

I kissed him on the cheek as a thank you and he looked as bashful as a young boy. I think I fell in love with him from that moment.

I remember that first week so clearly. At 7 o'clock on the Tuesday I went to Bernard's and Michael's house. The men had pointed out to me that a path had been made along the whole length of the row connecting all our back doors to one another. It was visible from the river but not from the road and so gave a large degree of privacy to our movements. I knocked on the door and Bernard let me in.

For this first visit I had decided on a formal note; I wore skin-coloured lacy panties and bra and thigh high stockings, a pair of court shoes (I found true high heels excruciating) and a smart navy two piece with a plunge neckline and, a touch of daring, no blouse. I had, of course, shaved every vestige of hair on my body.

Clearly the men had also felt that formality was the order of the day. They were in jackets and ties. We ate a very ordinary meal they had prepared, which was all I expected, but for which they appeared to expect gushing thanks. The wine was plonk (I know a thing or two about good wine) and they discussed it, with much pretentious examining of colour and bouquet, intended to impress me. Immediately we had finished the meal they led me upstairs and we undressed. For their age they were in good shape with well defined abs and pecs and firm buttocks. They indicated that I should kneel in front of them and handle and lick their cocks into life. This I did and they took me turn and turn about in mouth and cunt. They were polite but it felt as though they were doing me a favour. I was there to please them and there was no thought of pleasing me. I left the next morning fearing that I had made a dreadful mistake.

I had no sooner entered my own house than the phone rang. It was Peter.

'Have those bastards hurt you?' he asked.

I hastened to assure him that they hadn't hurt me physically but that I felt used and ashamed of myself for submitting to them and I thought I should leave.

'Please don't go. What do you want me to do? Shall I go and kick their heads in?'

I calmed him down as best I could and promised I shouldn't make any decision until after he and I met later that day.

'We don't have to do anything if you don't want to. We'll just talk if you like,' said Peter but, bless his kind heart, his voice was freighted with the expectation of disappointment. I wondered how much hurt this lovely man had experienced in his life so far. 'Too much,' I thought.

I asked how he knew I was home. I was so touched by his answer.

'I've been down my garden since six o'clock this morning waiting for you to come out of their house to see how you looked, to make sure you were all right. I saw you looked unhappy and I'd do anything to make you happy, anything you ask,' he said.

I thought for a moment. 'Dear Peter,' I said. 'Let me take a shower and rest for an hour or so and then how about if you and I go out for a walk together?'

'Would you really like that?' he asked and I could hear the incredulity in his voice.

'I should like that very much,' I replied.

.................................................

I knocked on Peter's door. It opened immediately as though he had been hovering there waiting for me. We walked together through the fields, along the edge of a beech wood, over a bridge, down a deep lane, foaming with huge sprays of wild rose-hips and old man's beard, and we talked. I asked him about his life. At first he was reticent, as though it could be of no interest to me and I was just being polite in asking, but soon I convinced him that I genuinely wanted to know and he opened up. He had left school at sixteen without any qualifications and had married a girl from school the following year. They had two boys in rapid succession. He had a very successful career as a heavy-weight boxer.

Peter had what he called 'feelings' for feminine men and one evening he had gone into a gay club in his home town and there had met a man a few years younger than himself and had fallen in love. He thought the man loved him in return but, instead, the man had tried to blackmail him and Peter had beaten him up. The consequence of this was that the young man reported Peter to the police, the affair became public knowledge, Peter was put on trial and went to jail. His wife divorced him, his sons disowned him and his career collapsed.

When he came out of jail he moved away from the area where he was known, changed his name, and took work as a navvy on building sites and as a bouncer in pubs and clubs. He tried to get work as a coach but his record pursued him and now he made a living as a carrier, on his motorbike, for various firms.

We walked and we talked and I told him a little about my life and my decision to live as a woman. We found we could make each other laugh. By six pm we were hungry and in a tiny hamlet we found a fish and chip shop with a few tables outside, where we sat and ate an ambrosial cod and chips, washed down with a large beaker of tea each.

'A lady like you is used to something better than this,' said Peter, ruefully.

'This lady likes being here with you better than dining at the Ritz with anyone else,' I replied. I had fallen in love with him and I wanted this dear, lovely man to know it.

We walked back hand in hand and went straight into Peter' house and he took me to bed. He let me undress him and I encouraged him to undress me. He touched my clitie, my breasts and my pussy lips with such delicacy and he brushed his lips across my nipples so expertly that the hairs rose on the back of my neck and I could hardly breathe for my longing for him to sink deep into me and take me. This he did many times during the next twelve hours.

12