A story of Agony Aunts ...and an Agony Uncle (part 1 of 2)

Thirty years ago I was finishing my first year of studying literature at a university in a northern English city. I’d gone there primarily because they’d have me, but also because it was only about seventy miles away from my home town, meaning it was a bit too far to commute – so I’d be living away from home. However it was still close enough to return for weekends if ever I felt homesick or there was a family function (or football match) I needed to attend.

I was all set to spend the summer back with my parents and expected to be working, as I had in the previous summer, as a labourer at the metal factory where my dad worked. It was a skive really, with plenty of overtime available, and volunteering for the dirty jobs got you extra pay too, so what was not to like!

Unfortunately, during the last week of term, a parked car with a dodgy handbrake decided to roll down a hill – and into my parents’ house, luckily while nobody was at home. My parents had to temporarily move in with my grandparents in their small flat, meaning my free lodgings for the summer would not be available unless I was prepared for a couple of months of nights spent in a sleeping bag.

Dave, one of my flat-mates, was a year ahead of me at uni and he pointed out that this could be an opportunity as well as an annoyance. The rent for our flat was already paid up until September, and that meant I could have it to myself for the rest of the summer since all of the others would be away. One of Dave’s former flat-mates had done the same the previous summer and got himself a job at the city’s local newspaper, The Evening Dispatch, and he’d really enjoyed it. So Dave offered to phone his old mate for me if I wanted, and to ask him if he could put in a word for me at the paper.

That didn’t seem a bad idea to me, so phone calls were made, an interview with the deputy editor was arranged and attended, and a job offer was made and accepted, albeit with noticeably smaller remuneration than the labouring would have provided. “But needs must” I thought.

I arrived bright and early the following Monday and the receptionist sent me to the personnel department for the usual form-filling, followed by the induction lecture that every new employee would receive. I was then handed over to a girl who gave me a tour of the building. Serena was, I’d guess, around nineteen, like me. She was pretty and lively, and on the way round I learned that she also was a student, back home for the summer from one of the Bristol universities and living in the city with her parents. She had worked for The Dispatch the previous summer too, which was how she already knew the ropes. I also learned that… she didn’t have a boyfriend!

Serena then took me to see George, the deputy editor who had interviewed me, and who would now be my direct boss. He reminded me that it was only a holiday relief position so I could find myself doing lots of things in the editorial department – mostly mundane stuff like filing, checking expenses forms, sharpening pencils and who knows what else.

He then asked Serena to show me to my desk and introduce me to my main task, which had been hers the previous year – being in charge of the Spot-the-Ball competition. Those competitions now seem to have disappeared (along with most local papers) but back then they were good little earners for newspapers.

A form, printed in the Saturday edition, would show an action photo from a recent local football match, from which the ball had been airbrushed out. Readers would put crosses on it to show where they guessed the ball had been. They’d then send the form to us with a cheque or postal order for the entry fee.

My job was to open the envelopes, process the fees and stack the forms (one stack per mailbag – of which there were quite a lot.) Then on the Friday I’d grab a handful of forms from each pile, mix them up and find one winner plus five runners-up from among them, using a transparent overlay sheet marked up with the actual position of the ball. Finally I’d pass on the prizewinners’ names to a journalist who ensured they’d appear beneath the following week’s entry form.

Having got up to speed on that job, George gave me something very different the following Monday. As I hadn’t yet passed my driving test, he told me to go by bus to pick up the copy (i.e. text) for that week’s Dear Molly agony aunt column from Molly’s husband. She worked from home and had completed that week’s column but had been taken ill before she could post it to us – email was yet to take off. Now she was in hospital and unlikely to be back out again and writing her column for a few weeks at least.

When I collected the copy I sympathised with Molly’s husband and hoped she would be well again soon, before setting off to return to the office. On the bus, I read her article but wasn’t very impressed. When I brought it to George, he asked me if I’d read it, and after I said “Yes!”, he asked me what I’d thought of it.

I said “To be honest, I was a little disappointed with it!”

George thought for a moment, then said “Well, we now need to find a temporary Molly over the next few weeks so why don’t you see if you can produce a better answer to the same question?

So I spent an hour pretending I was Molly, writing my own reply.

Most agony aunts were, and probably still are, women, because they generally tend to be the more caring gender. But not being a woman, I worried that I perhaps could do with some feminine input to make sure I didn’t make that week’s problem worse rather than better. So I had a word with Serena. Well, it was a good excuse to do so, anyway!

The outcome was that she agreed to go with me to a pub, straight after work, where we found that several of the journos had beaten us to it, loudly demonstrating what they’re infamous for. We then quickly moved into a quiet corner of the pub’s other bar and I showed her both mine and Molly’s versions, and asked her for her comments. She said mine was better but pointed out several things which I hadn’t noticed that women might have a problem with, so I was glad that I’d asked her. I also asked if she’d mind if I added her suggestions to my version so I could present it to George as a joint effort, and she said that was fine.

With that out of the way we then had an enjoyable chat for an hour and then for a while longer as I walked her home, which wasn’t much out my way. I asked if she’d like to go with me for a Chinese meal at the weekend. She said she’d love to, and I arrived home very happy.

Having been spotted together by the journos, by the end of the next day the grapevine now regarded us as an item and I think that both of our profiles at The Dispatch had been raised as a result. In the meantime, I’d modified my Molly article to incorporate Serena’s suggestions and showed it to George, who showed it to the editor. Serena and I were then called up to his office and, to cut a long story short, she and I got to share the job as Molly’s temporary replacement, both of us getting a pay rise as well.

It had been agreed that we’d continue to use Molly’s byline, but we were over the moon just to have our own regular column for a few weeks. Molly had always worked at home, away from the hectic office so, with me having a flat, I thought it might make sense (and Serena didn’t disagree) for she and I to work there together – and away from office distractions.

That meant we needed to start work on a new column before the weekend so we agreed that we’d walk from the office to the flat on the Thursday, have a ready meal, work on the column, and I’d walk her home to her parents’ house by 11pm. And that’s exactly what we did, having chosen some less-than-taxing problems for our first column, and the co-operative writing went well. We had left a few days spare before the deadline so we could do some tweaks if necessary, but were both reasonably pleased with our efforts, as subsequently was George. When we arrived at her parents’ house, if Serena’s mother had looked outside after hearing our footsteps by her front door, she’d have seen our first brief kiss.

Saturday soon came around and I went to Serena’s to be introduced to her parents before we walked to the restaurant for our Chinese meal. It was good, with plenty of laughter and without any flying chopsticks, although we left a somewhat messy tablecloth. My offer of coffee at my place was accepted and, being a perfect gentleman, I again escorted Serena home at an acceptable hour, but any onlooking parent may have needed a longer look this time.

We arranged to make Wednesday our regular ‘Molly’ day so on the next one we arrived at my place with a takeaway meal and the following week’s crop of Dear Molly letters. They included one from a lady whose husband liked to dress in women’s clothes. She’d accepted it before they married but now it was putting a strain on their relationship and she didn’t know whether to leave him or not. I’d not had any experience of such things but Serena said her Uncle Jim was also her Aunt Jemima, a drag artist, was quite open about it and was a good laugh.

She then looked at me for a few moments.

“What?”

“Oh, nothing really. I was just thinking that you’d make a good-looking woman.”

“You can’t be serious!” I said.

“I am. You’re not too tall, quite slim and I think that with a bit of makeup your face could look quite cute. Even pretty.”

“Really?”

“Yes, really! In fact, why don’t we find out at the weekend? If you make me dinner on Saturday, I’ll bring some stuff over and we’ll give it a try. I’ve often wondered what it would be like to sleep with a woman…”

...And she had me there. Hook, line and sinker! I was lost for words!

Eventually I said “Er, er… I think we need to get back to work!”

We agreed that we’d put that particular letter back in the pending folder and go for one about a gambling addict instead, and Molly’s reply to that was finished well before we needed to begin our walk to Serena’s. By now I’d have been surprised if either of her parents had wanted to see what they knew would be going on outside their door.

So more mailbags came and went and, in what seemed like no time at all, Saturday arrived. I had a busy day, cleaning and tidying, especially in my bedroom, then shopping for and preparing a meal that I hoped would impress Serena, as I’d be cooking it from scratch. She’d have to take pot luck with regard to flavour and under- or over-cooking though, as I wasn’t a great cook.

She arrived looking wonderful, and carrying a suitcase which seemed a bit large for an overnight stay, but who was I to find fault with a lovely girl having an overnight stay with me?

The meal worked out well, went down well and the evening was going well.

So after I’d said we’d leave the dishes until the following morning, Serena said “Right, it’s suitcase time!”

I hoped that might mean a bit of bedroom activity with a nightie which she may not get to use for very long, but I hadn’t recalled all of Wednesday’s blockbuster statement.

She dragged me into my bedroom and said “Strip!”

I excitedly took off my shirt and then she said “Stop! That’s enough!”

She felt my face and chin, looked all round my naked torso and said “That’ll do for now but you’ll need to shave your face a bit closer next time and lose some hair from your body and arms – and probably your legs too!”

“Will all that really be necessary? And is there even going to be a next time?”

“That’s what I’m here to find out!” she said as she produced a large makeup case to begin turning a pig’s ear into a slightly prettier pig’s ear. At last my memory returned and I now knew what she was up to."

At this point, any full-blooded man might have objected – unless, like me, they were on a promise! Thus I meekly went along with it, asking only that she wouldn’t do anything to me that would look obviously female once I became Paul again.

“Aha, so that means you’re used to not being Paul ALL the time then! You’ve done this before, haven’t you! I bet you even have a female name!”

“No! I didn’t say anything of the sort, or even imply it!”

“OK, I was only teasing! – But if you were to have a female name, what would it be?”

“I’ve never thought about it, but I doubt I’d want it to be as obvious as your uncle’s. Jim and Jemima might be a bit too close for someone who didn’t want to be identified as a transvestite, and I most certainly wouldn’t, and that’s assuming you’d ever get me to do this again.”

All the while she was doing stuff to my face that I couldn’t see, using stuff that I could see and smell, which was being applied with all sorts of brushes and pads.

“So, you haven’t told me your middle name. Do you have one?”

“It’s Emerson. My mother was into Ralph Waldo Emerson, the American writer.”

“Ah, that would be perfect. If you had a female name it could be Emma! Which is nothing like Paul.”

We carried on chatting about anything and nothing while she worked on me, until she said my face was done. She wouldn’t let me see the mirror yet, though, and produced a wig, which she fitted, followed by a bra and some wobbly pink things. She fitted them to me, then put a loose-fitting blouse over them, before finally putting a necklace around my neck and attaching some clip-on earrings which pinched a bit. Then she pronounced me finished, “At least for this first attempt.”

I did notice the last part of that but said nothing – being on a promise and all that! She then took me over to the mirror and I was gobsmacked. She was right, I did make a good-looking woman.

She said she hadn’t bothered with my nails and lower body as what she’d done wasn’t too size-critical or difficult to remove, but if I’d like to see the full effect she’d need to take my measurements and find clothes and shoes that fit. Some of hers might be ok but we’d have to check that out.

With that, we retired to the sofa to drink wine, chat and have a bit of close contact before I (or was it Emma?) was led to Paul’s bed – after ensuring we had both removed our makeup of course! And, contrary to my earlier guess, the suitcase had in fact contained two nighties, both of which of which were worn, but not for very long. And the front door of Serena’s parents wasn’t darkened at all that night!

So the next day, after the delayed washing-up, we had a leisurely breakfast and then Serena measured me everywhere, which took a while as we were both getting frequently diverted. Then we had a shower (ditto) and got ready to tour the shops. I (as Paul) was ostensibly accompanying my girlfriend while she looked for new clothes for herself. We didn’t get much, other than a bra and pantie set that she bought in my size, but the experience was mainly an introductory course about women’s clothing.

Serena was determined to get me to go the whole hog with the crossdressing, and I must say that her enthusiasm, plus the memory of how I’d looked in that mirror, was getting me more intrigued too. So we made a plan for the following week, to find out out exactly what we could make do with and what we’d need to buy on the following Saturday morning.

Serena was aiming for us to go clubbing on the Saturday night, but I thought that was a terrible idea because I’d be found out. However, she said that Saturday night, being more crowded, would be better, as more people to look at meant less time spent scrutinising any of them. I didn’t really believe a word of it but gave her the benefit of my lust.

I was able to go round to Serena’s on the Tuesday while her folks were out and, with us being not too dissimilar in size, I tried on some clubbing dresses that she’d laid out. She had some slingbacks that would do at a pinch (pinch being the word), so I was more or less sorted with minimal outlay and, seeing myself in her mirror dressed in her gladrags, I was starting to look forward to dancing in them.

However, she also provided me with some jeans and a top for the shopping trip, a coat for the evening, plus some other stuff I’d never have thought of. And I was able to take all my new wardrobe additions back home with me but needed several large bags.

So, on Wednesday, once Molly was out of the way, our evening morphed into a dressing-up practice, a girlie talking and walking practice as well as a sleepover practice. The next morning, our bleary-eyed appearance provoked a fair few knowing glances, and their assumptions weren’t incorrect!

Soon it was Saturday morning again and Serena arrived in time to relieve me of some hair – in fact most of it below my nose, and even some of it above – before she turned me into shopping-mode Emma, for which I used my own new tennis shoes. We booked a taxi to take us to a neighbouring town and thus minimise the chances of me being found out, despite Serena’s confident assertion that even my own mother wouldn’t recognise me!

We bought most of what we’d need for the evening and had lunch in a shopping centre pub. I noticed a few lads looking at us but none of them spoke – which was just as well as, although I was becoming more comfortable as Emma, I wasn’t there yet. But gradually I got more used to it by just thinking of myself as one of two girlfriends out shopping, albeit I was the plain one while Serena was the gorgeous one. Which perhaps took the pressure off me.

By late afternoon we were shopped-out and making our way towards the taxi rank when two lads recognised Serena and started talking to her. She introduced me to James and Andy as Emma, a student friend of hers. I suspected that one of them might have been an old flame of Serena’s, but they both obviously knew her quite well, were very entertaining to talk to, and involved me in the conversation. Anyway, after a quarter of an hour I was genuinely worried about the time so apologised to them before saying that we really ought to be leaving.

Serena then picked up on that, saying “Oh, gosh, Emma’s right! We’re going out tonight so we really do need to rush. It was nice seeing you both. We must meet up again some time soon.”

However, James then said “We were about to leave shortly anyway, and can give you a lift back to the city if you want.” And we did, and they did, and we all continued our jolly conversation all the way back to the flat.

As they drove away after dropping us off, I said to Serena “At first, I thought James might be an old flame of yours, but then I changed my mind and I think he and Andy are gay, Am I right?”

“What? Gay? Of course they are! James is my Uncle, Uncle Jim.”

“Oh, of Aunt Jemima fame?”

“Yes, he’s only four years older than me, more like a cousin really. Andy is his partner.”

“Let me guess, Aunt Andrea?”

“Correct. You’re getting good, Emma!”

“So, was it really a coincidence that we met them?”

“Erm…”

“I thought so! You set me up!”

“It was only as a bit of practice for you and you handled it ever so well. I’m so proud of you!”

So then it was a mad rush to have showers, grab something to eat, get dressed and glammed up and leave enough time to take some pictures of ourselves with my cartridge film camera before our taxi arrived. We had the same driver as that morning and he said “I thought you both looked lovely this morning but now you take my breath away.”

Of course that’s probably a line every taxi driver learns if he wants to get bigger tips, but it certainly worked on me!

We arrived early at the club and I was quite nervous so needed to use the loo. Serena accompanied me, mainly to make sure I didn’t use the wrong door. I was touching up my lipstick before leaving when a girl said “I’ve not seen you in here before.”

I said “No, I’m just visiting for the weekend, and I’m staying with my boyfriend.”

“Pity!” she said. “I’m jealous of your boyfriend!”

Just then, Serena came out of a cubicle, stopped and stared at me for a couple of seconds before continuing towards the hand basins, then said to the girl “I’m jealous of him too!” I didn’t know which way to look until the girl left, and we both started to laugh as soon as the door closed behind her.

So those experiences, plus chatting with James and Andy, had set me up for the evening, and, as the place filled up, my nervousness disappeared. Serena and I danced with each other, then with pairs of lads, and even each of us one-on-one with a lad at times. It was all great fun and we turned down lots of suggestions and invitations before our taxi driver returned to try out his other tip-worthy lines on us, and we ended the evening back at the flat, falling asleep as soon as our heads hit our pillows!

So, having proved I could get away with pretending to be a girl, I felt it had been instructive to see life from the other side, but having been there and done that, I also quite liked not needing to pretend that I was anything other than a man, and Serena didn’t disagree. So we didn’t bother doing it again, but the memories of it, and the photos, were good to have.

I did conclude that having a drag queen for an uncle had probably influenced Serena’s enthusiasm for feminising me to some extent, but how and why didn’t really bother me, because it had brought us closer together – and it had been fun!

All too soon, September arrived and both Serena and I left The Dispatch to return to our universities, two hundred miles apart. Sadly, Molly never did recover enough to return to her column, and I dropped out of our arrangement, leaving the column in the very capable hands of Serena, now with her own byline. I knew that our relationship, both personal and professional, had been great while it lasted, but it wouldn’t have survived in those days before everyone had a personal phone. I did miss her, though, and we still kept in touch.

The next summer, rather than returning to The Dispatch, Serena took a leaf out of my book by staying on in Bristol, working for a local paper there while I returned to my parents’ newly-repaired house and the metal works. We would notify each other of any changes in our circumstances, so I knew that, after graduating, she had taken up a full-time job as a journalist with a sister-paper of The Dispatch, but still continued to write her Dear Serena column, while I had returned to my roots and the metal works while looking for a career.

Not long afterwards, in her weekly batch of Dear Serena letters, she found one from an unfortunate woman named Emma, who said she hadn’t got over splitting up with her partner two years earlier. Emma wanted some advice about moving on with her life.

Serena’s reply appeared in her column the following week, and she suggested that the best solution would be a clean break and a move to a different town. That would force Emma to sink or swim and not dwell on old memories, while creating a new life and generating new opportunities.

She even suggested a suitable town… which just happened to be the same town where Serena now lived.

And she was so proud of that particular column that she posted a copy of it to me.

It’s now a bit faded after thirty years, but she and I still keep it, mounted in its frame, in our attic.

Dear Molly ©2024 Suzie Dalkin

[Image derived from one supplied by Freepic – www.freepic.com]