Another Time Another Place Pt 1/3

Long Story but please stick with it (giggle)


This is an account of what happened to me some years ago. The names have, for obvious reasons, been changed. Even now as I recount it, it seems like it never happened and, yet, I know it did.

Both my older b*****rs, being 10 and 9 years older, had been Boy Scouts in a troop where we had lived up until the time I was 6. The Scout Master, Richard, was my father’s solicitor and he had kept in touch, after we moved away, by writing and visiting over a number of years.

When I was 16, we went back to visit the area where we used to live. This was some 200 miles away in the West Country and my father had organised for us to have a tour around calling in, over a couple of weeks, to see old friends and acquaintances. One such visit was to Richard for Sunday lunch.

Richard lived, on his own, in a largish house on the outskirts of the town. He had never married but had a s****r Sue, also unmarried, who ran a ladies dress shop in the town and lived over the shop. Richard would have been about 45 at this time and his s****r around 40. He was a hail fellow, well met, large of frame and bulky; enjoyed rugby and beer and was very knowledgeable about the local area which he would explore at every available opportunity. He also was one of the first people to have a colour video camera and I was fascinated when he offered to show me how it worked.

He showed mum and dad some video he had taken when he had been on holiday in Italy with his s****r. I was interested in the shots of Venice and Rome and that’s when he said that he could take me when they went next time. Richard said it would hardly cost anything because they both had to have separate rooms and so he could book twin bedded rooms for me and him at the same price as a double. For the price of the airfare I could have two weeks touring Italy with them organising, and paying for, everything else.

Mum was not so sure but dad was very keen. I saw him in deep and earnest conversation with Richard about how much it would cost. In the end it was agreed I would go.


9 months later I was put on the train at Leeds to travel and meet Richard and his s****r at King’s Cross. We would stay one night in London and then fly out the next evening to Rimini.

I had no qualms about sl**ping in the twin bedded room with Richard. I was a little homesick since this was the first time I had ever been away overnight but Sue was sympathetic and the excitement of my first flight eased the problem a fair bit.

Flight proceeded as planned and we checked into our hotel in Cattolica, which was to be our base. The room was very nice with a lovely sea view and exceptionally good appointments.

Two days into the holiday I had a slight upset stomach. Richard went down to breakfast and the beach with his s****r, leaving me in the room on my own. I slept for an hour or so and woke up feeling a bit better. Anxious for something to read I rummaged around in some papers in Richard’s holdall. That’s when I found the magazine. It was for homosexuals and had some very graphic pictures of men sucking other men’s cocks. Towards the back there was an article on transvestites and how they could be straight or gay. There were pictures of some stunning TVs and as I looked at them I got a tremendous erection. I then masturbated to relieve to the excited feeling that these images gave me.

Now I know it sounds stupid but; up to that point I had thought I was perhaps the only boy who dressed up. The whole magazine got me excited. I had never thought of myself as a homosexual but a vague interest reared up inside me. I read as much as I could knowing that I had locked the door and that I could slide the book back when Richard returned.

I heard him at the door, unlocked it as I quickly put the magazine back. He came in and asked if I felt any better and would I like to go down for a bit of lunch. I said I did; and I would, and we went down to the beach café.

I kept on thinking about the magazine. It filled in a lot of blank spaces in my mind for me. It also raised some questions; was I indeed a ‘poof’ as my dad had so elegantly put it? Was I eventually going to migrate to a full sex change?

At dinner, that evening, Richard explained that we were all going to Rome the next day. We would stay for two nights and drive back, possibly staying over somewhere else on the third night. I was excited by this prospect and the business about the magazine faded into the background.

The journey to Rome was interesting and the hotel something quite special. After a full day sightseeing I was tired but happy. We had retired to our room and I was just getting into bed.

“What seems to be bothering you Charlie?” Richard’s question came as a shock.

“Nothing; As far as I am aware!” I replied honestly. “What makes you think something’s wrong?”

“Well you seem to have been a bit pre-occupied since the other afternoon – you know after you had that bit of a tummy upset – still a bit homesick?”

“No I’m fine, really!”

“Wondered if the contents of my magazine might have had something to do with it?” The words hit me like a bolt from the blue and my face obviously reddened. “I could tell it had been moved in my bag you know!”

“Look I’m sorry – I really didn’t mean to pry – it’s none of my business.” I was now extremely embarrassed.

“You know there’s no need to get worked up old chap! – Perhaps you feel a bit unsure of your own sexuality? You can discuss it with me because as a solicitor any thing you tell me must be treated in confidence.”

I was very unsure of what to say but Richard coaxed a confession about cross dressing from me. I told him about my excursion into the village and how it had excited me. He told me that I was not to worry and that it was perhaps just a phase I was going through. I relaxed a little and he went on about different types of transvestites, homosexuals and sex changes. He finished his comments by saying perhaps I needed to see someone to put my mind at rest. I agreed and we left it that he might take me to see a man he knew in Rome. I began to wonder if the earnest conversation that dad and he had had back during our Devon visit had something to do with the holiday and the trip to Rome.


The following day just after lunch Richard suggested a trip to see the Vatican. We set off in a taxi but headed to the outskirts of the city. It did not look a particularly salubrious area but Richard seemed to know entirely where he was going.

The cab took us down a road which had large and very grand houses on either side. The houses had obviously seen better days and had been converted into flats and the like. We pulled up outside one which looked to be in better condition than the others but was still quite shabby.

We mounted the few steps up to a heavy wooden door and knocked. After a couple minutes, or so, a women answered, she was about 40, heavily ‘made-up’ and dressed in quite a tarty manner. She wore quite a short skirt, high heels and seamed stockings with ‘fully fashioned’ heels. I had only ever seen pictures of women in stockings and I could not take my eyes off them and wondered how she walked in the heels.

Richard spoke to her in good Italian and, from the nods and smiles he received; it was obvious that we were expected. After a while he handed her an envelope which was thick and bulky. She smiled at me, took my arm and led me into the building. I turned expecting to see Richard follow but he walked out through the door and back to the taxi away with a cheery “good bye!” and a, “I’ll see you later!”

The woman pushed me into a room which looked like someone’s lounge. She left and I stood feeling quite apprehensive – What the hell was going on? Was I to see a psychiatrist perhaps?

Almost at once the door re-opened and a very attractive Italian girl, probably in her late teens, came in and smiled at me. “ ‘ello!” she said in a broken accent, “You are Charlie yes?” “Yes!” I replied, rather weakly.

“You come plese.” It was a request rather than a command but I got the feeling to refuse might not be in my best interest. I followed her out of the door and down a darkened corridor. She had beautiful long black hair which moved with her as she tottered down the tiled corridor on a pair of stilettos which must have had 5 ½ inch heels. Fine black, seamed stockings encased her stunning legs and her short black dress fitted her to perfection. My eyes were riveted to her legs and ankles - as around the right ankle was a fine silver chain. Every so often she turned and smiled to ensure I was following and as she did so her breasts, which were not particularly large but were very pert, bounced in a gorgeous rhythmic motion.

As I watched; this vision of loveliness climbed a staircase and I dutifully followed. At about this time my adolescent mind began to put two and two together – I was in a brothel! Dad and Richard had obviously concocted some plan for me to loose my virginity and establish that I was a bloke and not a poof. It all seemed unreal and highly unlikely - would my dad do that?

100% (8/0)
Posted by charlottekerscot
3 years ago    Views: 396
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8 months ago
well it's interesting looking forward to the next installment
3 years ago
wow some start will read the rest thanks Candi