The Catch Ch. 01

CHAPTER 1 -- the first catch

There had to be a catch. There always was. And I fell for it every time. I was gullible and generally crap at life. I went to a crap school on a crap estate in a crap town. I wouldn't say my parents were crap, just a bit disorganized. They loved me and each other, just incompetently. I inherited their lack of talent.

When the catch came, it didn't seem too bad. Of course, the catch was that it was not the only catch, as I was to find out later.

I was in a pretty sticky spot financially. Now I was being offered a rather nice flat for half the rent I was paying on my present crap one.

"You have cooking facilities, and ensuite shower and toilet, so you can be quite private, if you like. As you see, there is a TV, computer and internet access. Plus a large desk for marking."

Marking! If you have any thoughts about teaching, let me tell you it can be rewarding, but marking is the biggest catch of all. The hours you spend marking, which no-one else appreciates. And here was a perfect teacher's pad.

The person offering to be my landlady was the former head teacher at my school where I teach maths. Unlike my school (where the maths teacher was an unwilling biologist) I actually had a degree in mathematics. A third class one from a second-rate university. A crap one, but I had a degree. In fact, I think the only reason I seemed to be successful as a teacher was that I was even a bit crap at mathematics, so I understood the pupils' difficulties.

"If you choose, you may also have meals sometimes with me and my husband Charles, and really regard us as family rather than landlords. There is just one thing requiring a little discretion. Are you still interested?"

Here comes the catch!

"Yes, it all seems very nice, and extremely generous of you Mrs -- I mean Gladys."

Although she had retired, I would have to try to get out of thinking of her as my boss. (And also a wonderful teacher, and the most organized person in the world.)

"I am sure I can trust you not to talk about this, particularly at school, but Charles occasionally likes to wear a dress at home. It is a harmless foible he has, and should not affect you in any way other than to treat him in a civil fashion as if he were my sister, Charlotte."

Some catch! But then, where was the harm in it? As teachers, we are increasingly being told to respect pupils who have different gender feelings.

Charles was some high up official in a bank, very imposing with his grey hair and smart suit when he came home from work. But at the weekend he became a smart older woman called Charlotte with a wig and dresses which had been adjusted to fit. It was actually no trouble to treat him as a woman. Increasingly he also changed for the evenings, though in a more casual way with makeup at least, and a dress or skirt and blouse, till I rarely saw Charles except in passing to or from work.

CHAPTER 2 -- the second catch

I should have guessed that something was coming, when Gladys started asking certain questions. How I was finding my accommodation, were there any ladies I would like to bring to my flat? Or perhaps gentlemen -- they really wouldn't mind, and would be happy to meet any companions. (Of course, there were no companions in sight.)

Finally it came out.

"Malcolm, as you may have observed Charles is pretty much always Charlotte at home. I don't know how to put this, but to be blunt it also applies in the bedroom, and I am rather feeling the lack. Now I realise I am somewhat older, but if you have sexual needs it occurs to me that we could help each other."

"You mean, you...?"

"Yes, Malcolm. To be absolutely clear, I am asking you to fuck me occasionally. Could you do that, do you think? At least until you get a girlfriend?"

(In the same way I had often been asked to look after games this afternoon, or cover second year geography this once, or do some of the administration. Could you do that, do you think?)

Had this prim and proper headmistress actually used the word 'fuck'?

I looked at her. To tell the truth I am a bit shy and was not meeting available women socially. The other female teachers were either married or lesbians, and the parents of pupils were hardly appropriate (or for that matter available). My marriage had not been a roaring success, so I was not God's gift, either. After nearly ten years, my former wife had a child, a nice flat, a considerable share of my wages and a lesbian lover. She was a great deal less crap than me in organising her life. I think we had been in love, as far as I could manage, and the sex was good. At least, it was sex. But we parted, on good enough terms for me to be able to visit my daughter once a month.

I had never thought about my head teacher as a sexual partner. Not only was she my boss, she was obviously out of my league. It took a moment to adjust to the possibility. Yes, Gladys really looked all right despite her age. At least she had decent size tits and (I supposed) a cunt. I um'd and ah'd but a shag or two would make a change from wanking. And where else could I get accommodation at this price? Fucking the landlady was something university students were supposed to do: maybe I was getting my due finally.

What can I say? The 60s-year old woman was as good as my 37-year old wife had been! She had nice round warm boobs and a welcoming pussy. The only difference was that she always applied a bit of lubricant to both of us, which actually was better. And of course, no periods. And no worries about contraception, just joyous thrusting and coming (at least for me). Oh, it was so good to have a curvy body in bed, to get my hands and face on her roundnesses, to suck her tits and best of all to pump hard into a welcoming cunt!

I think either her husband did foreplay, or she did it herself, which was good because I had been quite crap at it. Thus, she tended to arrive lubricated and, as the lads say "gagging for it". Just ready for cock! I kissed, nuzzled and groped her for my entertainment, but not for long, and she was so grateful when I thrust in, and pleased afterwards however long or short it was.

She tried to make out that I was fucking her whenever I wanted, but the truth was it was whenever she wanted. Which quickly became as regular as a school timetable. Four fucks a week, to fit in with schoolwork, in which she still took an interest.

Which suited me down to the ground. No more wondering if tonight was going to be the night. No more trying to suggest, or wondering if there was a hint. No feeling obliged to try and make her come. That was not requirement -- I think she got orgasms in other ways, but wanted the experience of a fuck. She was still my headmistress, the boss, and I was in my natural state of following a regular routine on someone else's responsibility.

Having done my duty, I would have to inform her of the progress of the school, staff and pupils in her absence. I really had nothing else to tell her.

I liked maths, I liked my job, I liked my flat; I could put up with marking. Most of all I could put up with a decent-looking woman wanting a shag, and allowing me to suck and fondle her boobs. The fact that Charlotte liked to wear a dress was hardly worth mentioning. In fact, I should be grateful for his making the cunt of his lustful wife so available. Not really a catch, after all.

CHAPTER 3 -- the third catch.

As Charles and I were working, it was not unreasonable that Gladys did all the shopping and housework, and she quite enjoyed it. She volunteered for a charity, doing a couple of half-days a week in the shop, or sorting donations.

I roughly made my own bed, but she cleaned and tidied my apartment during the day, changed the bedclothes and washed my clothes. I rarely made my own meals except when they went out together. She made me sandwiches when I did not fancy the school dinners, and reminded me to get a haircut.

In fact, I realised that she was no longer my boss, but effectively my mother, getting me ready for school. (I just happened to be a teacher, not a pupil.) She made sure I had decent clothes and was generally presentable each day. I accepted her choice for what to wear. I went to my room to do my homework -- i.e. marking -- but otherwise socialized with them. Sometimes we watched TV together, sometimes I watched in my flat when we wanted different things. She was always interested in what I had done in school today, and praised me for my success when the exam results came out. Our school did better than average in maths, and had more girls taking A level in the subject. We were both so proud when one of the girls went to Cambridge to read Maths!

My own mum had never been so organized. Obviously, I loved her in a way I did not love Gladys, but otherwise Gladys was the perfect mother. And I was fucking my mother! When I was marking, she would often bring me a cup of tea about 9 o'clock with her boobs out, and invite me to enjoy them for a little break. She felt so good to hug and kiss and fuck and was always pleased with my efforts. I had never been so happy in my life!

Charles had been changing quite noticeably, and I was eventually told he was taking hormones. Actually, I was beginning to find time with Charlotte very pleasant. Charles had been a bit intimidating: a clever successful man, knowledgeable and generally superior to me in every way.

However, Charlotte was a nice lady (and definitely a lady). Even better she liked maths! Charles had done accountancy and his natural talent had helped his banking career, but actually envied my experience doing maths at university.

I lent her a copy of "Why Beauty is Truth" by Ian Stewart (on mathematical symmetry) which she loved, and allowed me to teach her something about the maths behind each chapter. More books and discussions followed, making her the perfect girlfriend for a maths nerd. Apart from the sex, of course which I was getting with Gladys.

I gathered that Charles had been quite virile and their sexual activities had actually been quite kinky, though I did not know the details. Who would guess what this proper respectable headmistress and bank executive got up to in the bedroom? Other kinky people had been involved somehow, and eventually I got to meet some of them.

Jason and Lucille came round for dinner one day, and I was asked to join them. They were a gay couple, with Lucille being a man in women's clothes, but more convincing than Charlotte. Jason was a great big rugby player, and rather handsome. Apart from the clothes, there was nothing kinky or sexual about the evening. Just some intelligent, well-educated people having a pleasant time. Plus me.

There was no hint about what their relationship had been, except that at one point Jason called Charlotte 'Cindy', and they were both embarrassed.

After they had left. Gladys remarked how nice Jason and Lucille were as a couple, and I of course agreed.

"Don't you think Jason is handsome?" she added quietly.

Oh, I thought, here it comes! The big catch! I am going to have to fuck Lucille, which means a man's arse, and either suck Jason's cock or be buggered by him. It was all plot to get me into their kinky circle!

"I suppose so," I said grudgingly, adding quickly "but I don't fancy men!"

"Oh Malcolm! I didn't expect you to, my dear. But Charlotte and I do, and always get quite turned on by him. So I just wondered if you could see your way to letting Charlotte suck your penis, as she hasn't done it for a long time."

As she pointed out a suck does not depend on anything but the mouth, and I could close my eyes if I wanted.

"And imagine that Charlotte is some lovely young girl on your first date, if you like..."

What could I say?

As it turned out, Charlotte was rather good and very glad to do it. I now had a girlfriend who was happy to let me tell her about maths and keen to swallow my spunk. When I wasn't fucking my 'mother' of course. They told me there was no need to pay rent any more.

CHAPTER 4 -- the fourth catch

So I had free accommodation and meals in a house which understood the needs of a teacher. Any day I did not fuck Gladys, Charlotte was glad to suck me off, so my cock was getting good exercise. And there were some nice boobs available. There had to be a catch surely?

Apparently, Charles had decided to retire and become Charlotte full-time. However, the bank was so keen to keep him that they suggested he have the necessary operation and come back as Charlotte for a few years in a higher position.

I don't know the medical details (and did not want to) but essentially Charlotte was sore for a long while but had a vagina and breasts.

It took a while for them to heal, but eventually it was for me to take Charlotte's virginity.

To be honest, Charlotte still had the basic man shape, though with some rounding, but the surgeons had done a remarkable job with her pubes. They really looked like a vulva, and so far as I could tell, she had a normal cunt, which I filled gladly, all three of us being pleased with the result.

Charlotte's boobs were different, smaller and more firm, like young ones, which I suppose they actually were. I don't know how much came from hormones and how much from surgery, but they did the job for me.

It was agreed that I should fuck each of them twice a week, then the rest (fucking and sucking) was up to me, as little or as much as I wanted. There really was no catch, other than the limit to what I could manage. Even then, a bit of sucking without coming was nice.

Gladys made sure I ate my greens to keep me healthy and fit to serve them. I was so happy that marking did not bother me.

However, I was surprised when they introduced me to two of their friends, Claire and Emily, and suggested that it would be nice if I could possibly see my way to fucking both of them.

Claire was no problem -- a woman about my age and easy on the eye. Emily was different. She had a cock and balls, and no vagina. She was Robert, part-time, Claire's husband.

This really was the catch, but finally I tried it.

Claire sucked me to make me good and hard. Emily was in suspenders and stockings and a green dress with the skirt lifted, bent over the bed, already lubricated and prepared out of my sight. (I did not want to know the details.)

Frankly it was just like fucking a cunt from behind. Quite a good cunt in fact, though the man's bum was less impressive. Soon I was thrusting hard and enjoying every stroke until I slammed it right in, and shot my load.

Finally the Summer came round, and I had the best holiday of my life! Relations with my ex-wife had become very friendly, and I was invited to join them for a week at the seaside, which included my darling daughter. She was entirely happy with her two mummies, and had got to know me as Daddy on weekend visits. It was wonderful to be trusted with her playing on the beach and telling me about her year in school and observations on the universe. My wife's lesbian partner was clearly a better husband than I had been, in many ways, and I strongly suspect sexually. Without going into details, I said I had a regular sexual partner, and my wife said how pleased she was. We still loved each other, and were glad for each other's happiness. I shall be playing more of a role in my daughter's life in future, we have agreed.

When I got back, Claire and Emily were there, as planned, for a fortnight. Gladys and Charlotte were visiting their children and especially their grandchildren, so had invited them to see if we might get along together.

Emily had a daytime persona of Robert, and acted as referee with Jason's rugby club in the winter. They still had sex as husband and wife, but were both fucked on occasion by a young man. They wanted to try an extended time with Emily as a full-time woman, and hoped I might be willing to fuck her again.

I got to know and like them as people. It was no hardship to shoot a load of spunk into either of them, and they were as grateful as Gladys and Charlotte. After a few more goes with Emily, I understood why some men like having anal sex with women. I wouldn't say it was better, but a little variety can be nice. Claire wanted me to fuck Emily as much as possible, and said it didn't matter about herself, but Emily insisted that Claire got some of my cock as well. Oddly enough, they ordered each other to do it. (Some sort of game they had, I suppose.) I did my best, fucking at least one of them every day, sometimes both and sometimes being sucked off as well. Emily got most of my spunk, as requested! There was no shortage of foreplay to get me going, and I really enjoyed Claire's tits. I don't think I could manage it for ever, but as a holiday, it was worth the effort!

They were, of course, about my age, and so we had similar experience and nostalgia for the same music eras. They did not share my or Charlotte's interest in maths, but listened politely as I explained the Fibonacci number sequence which determined the number of petals in flowers during a stroll in the park.

We made various excursions but Emily most of all appreciated just going around as a woman. Walking down the street, buying groceries, wandering a shopping centre, having a coffee in public. I understood how much it meant to her, and Claire was so pleased for her. They obviously love each other very much. She liked the experience of being accompanied by a man, often holding my arm, and glancing to give me a smile.

In my disorganized manner I did not think about housework and cooking, but suddenly realised my room was getting tidied and all the jobs were being done. Charlotte did quite a lot, but Claire was the organizer. I guess my masculine thoughtlessness suited them, or at least I hoped it did.

One day Charlotte will finally retire and will go to the seaside with Gladys. They are getting older, though Charlotte is still a vigorous businesswoman and quite good looking in her smart tailored clothes, and Gladys is still a surprisingly randy housewife.

They hope that when that happens, Claire and Emily will move in with me, and we will enjoy many happy years together.

I think I have really struck lucky. Maybe there wasn't a catch after all.

(Claire's view of this is given in Magic Dress - Emily.)