DRESSING: PHASE 1 - A HOLIDAY IN VENICE
Barry Robbins and I have been best friends since we were three years
old and met in the Reception Class at Nursery School. Naturally as two
active, competitive little boys we had our moments and our spats, but
it soon became clear to our parents and teachers that we functioned
better together than apart. As we grew up it was apparent that our
talents and personalities complemented each other. Barry was the
imaginative one; I could come up with how to translate his dreams into
practical reality. He was the one for taking risks; I was more
cautious. Not overly so however, as the one trait we both shared was a
commitment to seeing through a 'dare'. If one of us ever 'double dog
dared' the other, we knew that come what may we had to see it through.
My name is Terry Alexander, by the way.
Our two families live close to each other in a leafy suburb of
Southampton in Hampshire. My Dad is a doctor in the local GP practice,
whilst Mum, who had trained as a lawyer, works for a Housing
Association. Barry's Mum didn't work but his Dad ran a thriving haulage
business. When we first knew the Robbins', Mr. Robbins worked all hours
to make a success of his newly formed business. Gradually however, it
grew and grew until, by the time Barry and I were in our teens, it was
very successful and the Robbins had moved into the most palatial house
in the district. The fact that Barry's Dad could, and did, indulge his
every whim, spending money like water, didn't affect our friendship;
whatever Barry had he shared with me. And it wasn't as if my parents
were short of a bob or two either; it was just a question of
relativities.
Somehow or other Barry and I managed to reach our teens without
incurring any serious injury. Given some of the things we dared each
other to do that was little short of miraculous. Then at about the age
of 14 puberty struck and our hormones kicked in. I suddenly discovered
girls weren't quite as boring as I had always considered them, whilst
Barry had a similar revelation in respect of boys. Yes he discovered he
was gay whilst I was straight!
We started dating and, when we each had partners, we naturally tended
to see less of each other. But we still played sports together; were in
the same class at school; and, anyway, teenage romances never seemed to
last long so our preoccupation with sex didn't really cut across our
friendship. I can honestly say Barry's gayness never concerned me at
all. He was my 'best mate' and something as trivial as sexual
preferences wasn't going to get in the way of that.
What did finally part us, however, was university. I wanted to work in
the field of fine arts either as a curator, conservator, or for a major
auction house. I dreamt of discovering an elusive, lost work by one of
the great masters. (Well we all need to dream!) For his part Barry had
long since decided his future lay in the field of European politics. He
fancied working for the Diplomatic Service and decided to study
languages, with particular reference to Italian and Spanish. Barry's
ideal course turned out to be in Manchester whilst my desires led me to
University College London. We both therefore went 'North" - (not
difficult when you live in Southampton!) - but Barry travelled somewhat
further than me.
We were both fully occupied during our first year at university but
just about managed to keep in touch via the odd email and on Facebook.
Come the summer vacation at the end of our first year, I for one was
ready for a break. Both Barry and I arrived back in Southampton at
roughly the same time - mid June. The summer stretched enticingly
ahead. Naturally first night home we met up in the pub for a drink and
to catch up on what had happened to each of us during the previous
eight months.
We soon discovered that each of us was just emerging from the ending of
brief but passionate relationships. My situation was quite
straightforward. My girlfriend had dumped me towards the end of term in
favour of a fellow classmate whose father had a yacht in the Caribbean;
no contest! Barry was more reticent in explaining why he and his
boyfriend had parted and I didn't press him. He would confide in me
when the time was right.
Anyway Barry had much more exciting news to impart. "My Dad has a
friend who owns an apartment in Venice," he started, "and Dad had
rented it for me for the summer so that I can practice my Italian. It's
a 2-bedroom place so of course you must come with me. You don't have
any other plans, do you?" he added anxiously.
"No, of course not," I replied, "and I'd love to accompany you. The
chance to see those wonderful Venetian paintings in the locations for
which they were commissioned is something I have always dreamed of
doing!" And so it was agreed; the two of us would set off for Venice
just as soon as we could sort our travel arrangements.
Whilst the most obvious way to get to Venice was to fly, for some
reason Barry seemed set on going by train. As I was relaxed either way,
train it was. I discovered why he preferred this mode of transport when
we arrived at the station. My luggage consisted of one medium sized
suitcase for my clothes and another, smaller one, stuffed with art
books and painting materials. Barry, on the other hand, appeared with a
trolley laden with three of the largest suitcases I had ever seen.
"What on earth have you got in there?" I exclaimed in amazement. "I
thought you were studying languages; that should mean that you need
less stuff than me but you seem to have at least twice as much!" "None
of your business," Burry replied in a huffy tone. "We are going to be
in Venice for several weeks and I don't want to get out there and
discover I have left anything important behind." Well, each to his own,
so I left a porter struggling to load all Barry's cases, plus mine,
into the luggage van and the two of us set off to find our seats.
We took the Eurostar train to Paris where we had to change stations
from the Gare du Nord to the Gare de Lyon for the overnight train to
Venice. We enjoyed a very pleasant meal in the dining car and then
retired to our sleeping compartment where we slumbered comfortably
whilst the train rushed across Europe. A wakeup call and a welcome cup
of coffee greeted us as we approached Venice and the light glittering
on the lagoon as we crossed the causeway was spectacular.
Barry tracked down a porter with a substantial trolley and tipped him
well to transport our bags from the station to our apartment in
Cannaregio. We decided to walk. Emerging from Mussolini's 1930's
railway station onto the Grand Canal was like stepping through the
portal of a time machine. Although we knew we were in a bustling modern
city, our initial impression was of being transported back to the time
of the Renaissance. Gleaming water taxis and black and cream Vaporetti
were as nothing against the backdrop of polished marble and crumbling
stucco on the facades of the various palazzi lining the Grand Canal. I
was eager to start exploring, but that would have to wait until later;
our first priority was to find and get set up in our apartment.
Cannargio is a district of Venice lying to the north of the Railway
station. It is off the busy tourist route and a relatively quiet part
of the city. Our apartment was on the top floor of a building in the
Campo Santa Fosca. I was surprised at how spacious it was for a two
bedroom flat. Clearly it had once been part of a much larger
establishment. There was a living room with comfy if battered seating
at one end. At the other was an antique oak dining table that would
comfortably seat eight. A modern kitchen led off at that end of the
room. French windows led out onto a vine-shaded roof terrace with more
seating and eating space. The two bedrooms were each equally spacious
and furnished with heavy antique furniture. Both rooms were en suite.
We would be very comfortable living here for the summer.
The owner's agent had bought in basic provisions so that we had a meal
ready for that night, together with a few bottles of wine, coffee etc.
We could stock up our provisions leisurely tomorrow.
As it was his father renting the apartment, naturally Barry had first
pick of bedroom. There wasn't much to choose between them and I was
well pleased with the one I ended up with. It was furnished with a
vast, antique, double bed; and enormous walnut wardrobe; matching
dressing table; writing desk; and a comfy armchair. The window gave me
a view over the red, pan-tiled rooftops towards the spires of a number
of churches. Knowing that many of these would contain stupendous works
of art made me eager to get out and explore. If I leaned out of the
window and looked straight down, I could see the narrow canal that
skirted our building. Just at the moment there weren't any boats going
up and down but later I was to discover that working boats used this
route to service local shops.
It didn't take me long to unpack my suitcases and put my clothes away.
They looked lost in the spacious interior of my wardrobe and I wondered
whether, like Barry, it would have been sensible to have brought more
things; too late to worry about that now! I laid my books, writing, and
painting materials out on a small bookcase and sauntered back to the
lounge ready to meet Barry and set off exploring. But he wasn't there.
I waited...and waited; he seemed to be taking ages to get unpacked. I
called out to him; "Hey Barry, what's keeping you? Even with three
cases to unpack you should have been ready by now." A grumpy voice
responded, "I'm nearly ready; don't be such a fuss-pot; have a glass of
wine and chill out!" So I took his advice; poured myself a glass of red
wine and went to sit on the roof terrace. It was gorgeous! Just sitting
there soaking up the sun, smells, and atmosphere made me realize I was
actually in Venice at last.
Barry finally appeared looking hot and flustered. "Sorry" he apologized
"but I had to put everything away carefully and make sure nothing had
got creased during the journey. A few things had, so I had to iron
them." Ironing the first moment you arrive in Venice? This didn't sound
like the Barry I knew but, hey each to his own. I poured him a glass of
wine and we sat companionably side-by-side letting our stresses and
strains soak away.
Eventually I did manage to drag Barry away and we set off for an
initial exploration. I, for one, wanted to experience the major sights
- St Mark's Square; the Rialto; etc - when they were not full of day-
trippers. I planned to get up early and go and visit them before the
hoards arrived. Fortunately Barry was of a similar mind, so this
evening we limited ourselves to a walk around our immediate area.
There are three long, parallel canals running through Cannaregio and we
gently strolled up and down them. This was a residential area, but
there were a number of small bars and restaurants dotted about and we
made a note of some we liked the look of and which we though would be
worthy of further examination on a future occasion. I had picked up a
map of Venice at the station and discovered that we were very close to
the original 'Ghetto'. Venice was one of the first cities to segregated
Jews into a specified location in the middle ages, and the name for
this area of the city was subsequently adopted as the description of
all such places throughout Europe.
Nowadays the Ghetto is a peaceful area with high buildings set around a
couple of piazzas. (When you live in a confined and demarked area, the
only way to expand is upwards!) I was surprised how small an area the
Ghetto actually occupied.
By now we were getting hungry, so decided to head back to our apartment
for dinner. The letting-agent had laid in some antipasto; lasagna that
only needed heating through; a fresh salad and some biscotti and Vin
Santo. This repast, washed down with a bottle of delicious Valpolicella
went down a treat.
We were ready for our beds after supper and turned in. The following
morning I awoke early - (having set the alarm on my phone); knocked
loudly on Barry's door and, in spite of his protestations, insisted he
get up and join me on my visit to St Mark's Square. The walk through
the awakening City was magical. As we crossed bridges over narrow
canals, we could see the working boats plowing up and down, delivering
supplies and removing refuse.
Arriving in St Mark's took our breath away. The light glittering on the
mosaics of the Cathedral; the Doge's Palace; the Campanile; all set
within the asymmetrical but beautiful proportioned square, fully
justified Napoleon's description of it as "the drawing room of Europe'.
We didn't rush to visit any of these famous landmarks; we were content,
on this initial visit, to just sit on the steps and soak up the
atmosphere. After a while Barry suggested a coffee. I knew, from my
researches, that it would cost an arm and a leg to sit down at one of
the cafes that lined the square. But what the heck; it was our first
day and the place was relatively deserted, so we took a table at
Florian's and sat sipping our espresso coffees contentedly and in
silence.
At about 9 o'clock, as tourists started arriving in significant
numbers, we paid our bill and headed off to find breakfast. Using my
map it didn't take long for us to find a quiet piazza off the regular
tourist trail that had a small caf? within it. We chose one where the
tables were in the sunshine and ordered more coffee, rolls and jam. It
was delicious.
Now I can bore for England on the delights of Venice, but I am sure
that readers would soon give up if I did, so I won't recount all the
places we visited that, and subsequent days; nor the amazing works of
art we oohed and aahed over. Suffice it to say that my expectations as
to the magnificence of what we hoped to see were greatly exceeded. My
pen and paintbrush were kept busy. Barry's linguistic skills were put
to good use, soliciting directions to some of the more obscure
locations; ordering us delicious meals in cafes and restaurants; and
generally ensuring we were able to understand the context and
significance of what we were seeing.
However, back to that first full day in Venice.; We spent the morning
dipping into a number of different churches; took lunch in a small
trattoria; and retired to our apartment for an afternoon snooze!
I awoke about 5:00pm and called out to Barry to enquire what ideas he
had for the evening. He shouted back that he had " taken the liberty of
booking a table at a restaurant recommended by the owner of the
apartment we were renting". Our booking was for 8:00pm and until then
he was going to rest up! Fair enough; I took a couple of my reference
books out onto the terrace and spent an enjoyable couple of hours
reading up about the treasures we had seen that morning. At about
7:00pm I decided I ought to get cleaned up ready for our evening out
and went back to my room for a shower and shave. This didn't take long
and by 7:30 I was back on the terrace refreshed and smartly, if
casually, dressed. I poured myself a glass of prosecco and waited for
Barry to appear. Eventually he did so and, on his entrance onto the
terrace, I nearly chocked on my wine!
For the person who emerged from his bedroom wasn't the Barry I had
known for some seventeen years. The figure I saw before my eyes was
dressed in a tight cream dress; high heels; had shoulder-length blonde
hair; and was wearing makeup! "What the f***!" was my initial response.
To his credit, Barry blushed and avoided my astonished gaze, casting
his eyes down to the floor. "I'm sorry, I know I will have shocked
you," he started. "But after much thought, I came to the conclusion
that there was no way I could explain to you, so thought the best thing
was to let you see for yourself'."
"But why are you wearing a dress and pretending to look like a woman?"
I enquired in a strangled voice.
"It's because I am a transvestite," Barry answered simply. "Look I can
explain, but first of all can you please pour me a drink; I really need
one!"
I did as he requested and he sat down in a chair opposite me, crossing
his legs in a most ladylike fashion. "I realize this must come as a
real shock to you," he started. "It all began in Manchester when I went
to university there last October. I hadn't been there long before I
discovered that there was this amazing area in the city known as 'The
Village'. It is right in the centre - around Canal Street - and it is
THE place to go for 'gays'. Naturally I went there at the first
opportunity to check over the talent. I soon felt at home and made
friends with a number of guys and the sex started to flow!" ('Too much
information' as far as I was concerned!) "Anyway" Barry continued, it
wasn't long before I discovered that as well as being the place for
'gays'; The Village was also the area where transgendered folk meet up.
I was a bit mind-blown the first time I encountered a cross-dresser in
a bar, but once I had chatted to a few I came to realize they were just
guys like me doing 'their own thing'. Who was I to criticise?"
"After a while I became fascinated by these guys. What was it about
female clothing that turned them on? Of course I asked one or two whom
I had got to know reasonably well, but they all told me there was only
one-way to find out - to try it for myself; so I looked up 'transgender
- Manchester' on the Internet and found a 'dressing service'. I booked
a session and was dressed and made-over into the semblance of a woman
by this amazing lady. I thought I would be really embarrassed, but
Madeleine made me fell right at home; as if cross-dressing was the most
natural thing in the world. I was amazed at the result she achieved; I
really looked feminine. At that moment I decided I needed to take this
experiment further. So, to cut out the boring detail, I put together an
outfit of female clothes from a number of charity shops; purchased a
basic makeup kit from Boots and a set of underwear from M&S; bought a
cheap wig; and made myself a set of boobs from a the feet of a pair of
tights and bird seed!"
"After practicing a bit in my room, I finally summoned up the courage
to go out 'dressed'. And I loved it! I soon made a whole new circle of
friends amongst the transgendered community and haven't looked back
since. That's not to say I dress all the time; I don't. Gays aren't, in
the main, attracted to cross-dressed males; why would they be? They are
interested in relationships with other men; not men who like to pretend
they are women. Also, and I found this surprising, the majority of
cross-dressers are 'straight' and are not looking to get off with guys.
They might enjoy flirting and some, of course, do take it further, but,
in the main, for most cross-dressers it is the 'dressing' that is the
attraction."
However, I soon discovered there is a whole pool of guys out there who
like to think of themselves as 'straight' and, in some way I don't
quite understand, think that if they go with men who are dressed as
women; then they aren't homosexual! Still their self-delusion doesn't
worry me; I have had great fun getting off with guys who think I am
pretty!" Brian started giggling, and in spite of myself, I couldn't
help joining in. "You are incorrigible," I finally managed to blurt
out; I can just envisage you as a right little slut out on the prowl
for a quick 'trick'!"
"But seriously," I continued, "whilst I can sort of understand your
going on the pull dressed as a woman in Manchester, why are all frocked
up here in Venice, on holiday with me - your oldest and best mate?
Surely you aren't hoping to seduce me?"
Barry punched me in the arm in a familiar gesture. "Of course not," he
laughed, "Even if I fancied you - and I don 't - I know I could never
get off with you. After all we have shared together, it would feel like
incest!"
"So why?" I queried.
"Well, so far I have only dressed in an environment where that is an
accepted practice," Barry explained. "I thought that it would be fun,
and interesting, to spend time 'en femme' 24/7 in somewhere, like here,
where no-one knows me and see whether I can get away with it. I don't
really care if someone 'reads' me - although, of course, it would be
nice to be taken for a real girl - as I am interested in finding out
how people react to me once they do discover that underneath my
feminine finery I am actually a bloke."
"Bloody hell, you are living dangerously!" I expostulated. "And you
expect me to go around with you like this and take my chances of being
beaten up by a bunch of homophobic thugs do you?"
"I'm sure it won't come to that," Barry hastened to reassure me. "But,
yes, it would be nice if you were to come out with me. In fact I have
booked the restaurant tonight in the name of Mr. & Mrs. Alexander, so,
unless you are really going to be a right drag, tonight we are going
out as a newly married couple!"
This took my breath away a bit but I managed to rally, "Just so long as
you don't expect me to take you to our 'honeymoon bed' afterwards!" I
joked.
"Of course not," responded Barry. "But does that mean you are up for us
going out together like this tonight?"
I was slightly hoist with my own petard, and reluctantly had to agree
to go along with Barry's scheme. "But just this once mind," I insisted.
"Let's wait and see," was Barry's somewhat evasive reply!
I poured myself another large glass of wine and downed it quickly in
the hope that it would fortify me for what lay ahead - (it didn't)!
Still a deal is a deal, so, taking a deep breath I said, "OK, let's go
for it."
Barry smiled his pleasure and, after gathering his handbag and checking
his hair and makeup in the mirror, we set off. As we crossed the piazza
outside our apartment, a thought crossed my mind. "How am I going to
address you tonight?" I enquired. "I can hardly call you 'Barry' whilst
you are dressed like this."
He blushed and avoided looking at me as he replied, "My femme name is
'Sylvia'," he confessed. "So for tonight I am 'Mrs. Sylvia Alexander'
here in Venice on my honeymoon with my gorgeous husband 'Terry'." Well
now I knew!
The restaurant 'Sylvia' - as I must now think of her - had booked was
on the Rio della Misericordia, only a few minutes walk away from where
we were staying, so I didn't have much time to get used to the idea
that for this evening at any rate I was going to have to behave towards
my best friend as if 'she' were the love of my life. The restaurant was
small and unpretentious, but there were a number of other people dining
and about half the tables were occupied. Trying to keep my voice calm
and steady, I spoke to the waiter who greeted us at the door; "My name
is 'Alexander'; my 'wife' reserved a table earlier today." He consulted
his Reservations Book; "Of course Sir" he responded with a smile.
"Please come this way. Is this your first visit to our restaurant?" I
told him that it was and that we had only recently arrived in Venice.
"You have chosen well Signore," he announced with pride. "Our
restaurant may be small but our chef is excellent. As we are tucked
away here, it takes a discerning tourist to track us down. I hope you
will enjoy what we have to offer."
By now we were at our table and the waiter seated Sylvia, who sat down
in an elegant feminine manner, carefully smoothing her skirt underneath
her. The waiter put menus down in front of each of us and handed me the
wine list. We sat and studied them. The list of dishes and wines on
offer wasn't long, which pleased me. I'm rather fond of my food and
drink and prefer establishments that go for 'quality to quantity'. "You
seem to have chosen well," I murmured to Sylvia as we studied the bill
of fair.
"I looked it up on the internet," she confessed. "I wanted somewhere
close by and this place came top of the list of recommendations."
We settled on our choices and, as would be expected of the 'man' in the
party, I ordered for both of us. We decided to share a plate of
Antipasto - which was delicious, comprising a variety of meats, fish,
and pickled vegetables. I followed this with 'liver Venetian style'
whilst Sylvia opted for a veal dish. I decided to try the local 'house
wine' and it proved an excellent choice. I was amused to see how
daintily Sylvia ate and observed that she left quite a bit on the side
of her plate. "What happened to your appetite?" I joked, leaning over
the table so that only she could hear.
"Wait until you try eating a big meal whilst laced into a tight
corset," she grumbled. I smiled, totally failing to note her choice of
words!
Not surprisingly Sylvia declined the offer of desert and, as I was
quite full myself, I did also. We both enjoyed a cup of espresso and I
had a glass of grappa before asking for the bill. I paid and we walked
outside. "Well that seems to have gone off OK." Sylvia breathed a sigh
of relief and I suddenly realised what a strain she must have been
under, wondering all the time if she would be exposed as a fraud.
"You were brilliant," I reassured her. "At times even I forgot that you
are really a man."
"Did you?" Sylvia asked, smiling up gratefully at me, "Only I was so
nervous. That is partly the reason why I could only eat a little of
that delicious meal."
Sylvia was so obviously delighted at her the outcome of her first
outing that I hadn't the heart to protest when she tucked her arm in
mine and snuggled into my side. We strolled slowly back alongside the
quiet canal, enjoying the warm evening air and the romance of the City.
Back in the apartment Sylvia announced that she was wacked with the
emotional strain and was going to turn in. "What about tomorrow?" I
enquired. "Are you planning to be 'Sylvia' again?"
"I will if you don't mind," she smiled. "I have really enjoyed tonight
and am looking forward to seeing how I get on in daylight. Thank you
for being so understanding and for giving me such a memorable evening."
Leaning forward she kissed me on the cheek and, before I had time to
react, had vanished into her bedroom.
There was still one glassful of prosecco left in the bottle we had
started earlier, so I took it out onto the terrace and sat quietly
trying to gather my thoughts. There was no doubt that Barry made a
convincing, even pretty, woman. I had enjoyed 'her' company. How did I
feel about that? It was a difficult question to answer and one I didn't
resolve that night. However, by the time I retired to bed, I had come
to the conclusion that I owed it to our long friendship to support
Barry as much as I could in his desire to explore his feminine side.
I slept surprisingly well considering all the excitements of the
evening, and awoke early and refreshed. Slipping on a shirt, pair of
trousers and my trainers I nipped out to the local bakery for some
fresh croissants. I also picked up a bag of ripe oranges at the
greengrocers. So, by the time 'Sylvia' emerged, it was to the smell of
freshly brewed coffee, warm croissants and freshly squeezed orange
juice. This morning she was simply dressed in a vee-necked purple and
white-stripped tee shirt, white capris, and low, wedge-heeled sandals.
Her blonde wig was pinned up and her makeup lightly applied, eminently
suitable for daytime wear. Somewhat to my surprise I found myself
thinking how pretty she looked!
"Gosh, you have been busy," she gushed, "I feel really spoilt. My turn
next time." Sitting down we tucked in and set about planning our day.
Given how little she had eaten the previous evening, Sylvia made a
surprisingly good breakfast. "I have skipped on the corset this
morning," she confessed, "I just couldn't face walking around Venice in
the heat with that constricting my tummy. Is my figure too boyish?" she
enquired anxiously.
"Not at all," I reassured her. "You have never been that large and to
my eyes you look just like a slim young woman. In fact you look
fabulous." I blushed as I realised what I had just said. 'Sylvia' was
delighted however. "Thank you," she gushed, "you don't know how much
your opinion matters to me."
"That's OK," I mumbled in reply, "I wouldn't have said it if it wasn't
true."
Avoiding any further potentially embarrassing conversation, we returned
to discussing how to spend our day. We finally settled on a walk across
the Rialto Bridge into the San Polo area and the Basilica dei Frari
with its wonderful works of art by Titian, Bellini, Donatello, and so
many others. After lunch, if we still had the capacity to look at yet
more art, we could stroll on to Le Chiesa di Angelo Raffaele where the
organ case is decorated with paintings depicting the story of "Tobias
and the Angel". These paintings have achieved a certain notoriety since
the novel 'Mrs. Garnet's Angel' became a best-seller.
And this is exactly what we did. The Frari exceeded our expectations
and I, for one was blown away by the sheer quantity of masterpieces in
one church. Sylvia, whilst not as into art as I am, also enjoys visits
to galleries and museums. She too was overwhelmed by what we were
seeing. The best news however, was that so far Sylvia seemed to be
escaping detection. We were able to stroll around the church quietly
discussing the paintings and sculptures without my being aware that
anyone was looking at us oddly.
We picked up some filled rolls, fruit, and a bottle of wine as we
strolled through the narrow streets and lunched alongside some
unremarkable canal in a little square. That is one of the delights of
Venice; there are so many outstanding places to visit that off the
beaten track areas unmentioned in guidebooks tend to be very quiet.
After lunch we relaxed in the shade whilst I read up on what we had
seen and Sylvia made copious notes in her diary. Finally we thought we
ought to get going again before we fell asleep, and strolled on to
Angelo Raffaele and the Tobias paintings. They were sweet and charming
and the area around the church if not distinguished by great
architecture was very characterful with small bars nestling alongside
little canals. We enjoyed a couple more glasses of prosecco!
After this we felt we had done enough for the day. Sylvia complained
that her calves ached from being in heels - (albeit low ones) - all
day. I, laughingly, told her to stop complaining. "Girls have to pay a
price for their appearance you know," I joked. If only I had known how
I was laying myself open, I might have thought twice before making such
glib remarks!
Although the streets and alleys twist and turn and it is easy to become
disorientated, if you have a reasonable sense of direction and are able
to read maps, it really isn't that difficult to navigate your way
around Venice. Hence it only took us some half hour to walk back to our
apartment via the railway station bridge.
Having enjoyed a full and busy day we decided to eat in that evening.
Sylvia set about making a spaghetti ragu whilst I nipped out for more
wine and bread. I also managed to pick up the makings for a salad. It
was very pleasant to chill out on our terrace. Not overlooked we were
able to relax and chat freely. We started off discussing all the
delightful things we had seen today but perhaps inevitably, our
conversation slowly drifted round to the 'Barry/Sylvia' dichotomy.
"Whilst I still don't understand your need to dress and present as a
woman," I started, "I have to admit that you pass very well for a girl.
I wasn't aware of anyone 'reading' you today."
"No, I was pleased and relieved at how well things went," Sylvia
confessed. "I have really enjoyed being out and about en femme and hope
I will be able to keep it up for the rest of the holiday."
"If you don't mind my asking," I enquired nervously, "but what do you
do with your cock? I couldn't help noticing today that even though you
have been wearing tight fitting trousers, there is no sign of a bulge
where there ought to be one!"
Sylvia giggled. "I wear an extremely tight gaff," she explained. "It is
a sort of cross between a thong and a jock-strap but contains a lot of
elastic so that when I have tucked everything away it is all held in
place. If you aren't too squeamish I could show you if you like." Now
after 17 years of friendship growing up, there were no secrets for
either of us about the other's body and, as I was genuinely intrigued,
I nodded my agreement for him to go ahead.
Standing and pulling down his/her capris, Barry/Sylvia revealed first a
lacy white thong and then, under that, what appeared to be a g-string.
His groin was totally smooth; no trace of 'male equipment'. "I push my
balls back up inside my body," he explained, "and then tuck my cock
back between my legs."
"That sounds dreadfully uncomfortable," I responded dubiously and with
an expression of distaste.
"Well it was a bit to start with," Barry confessed. "But you get used
to it and I don't even think about it now. You should try it sometime!"
"Don't be daft," I shot back. "I'm not a transvestite and you would
never get me into a torture garment like that!"
"Don't knock things you haven't tried," Barry responded, "who knows,
you might like it!"
"I'd look ridiculous," I muttered. "I'm not pretty like you and it
would be obvious I was a bloke in a dress."
"Who said anything about dresses?" Barry shot back. "I only suggested
you might care to try on a gaff just to see how easy it is to hide your
male bits. However, now you have raised the subject; I happen to think
you would make a really good-looking girl. We are both about the same
size and build, so if I can pass reasonably successfully, so should
you."
This conversation was getting out of hand. I had to admit it was my
fault, I had let my mouth run away with itself, but even so..... Barry
grinned at me. I had to smile back. He looked so bizarre, yet at the
same time oddly sweet, sitting there in his lingerie with his capris
and shoes on the carpet. So many of our arguments had started this way.
One of us would make a loose remark; the other would seize on it and
before you knew where you were the conversation had spun off in some
totally unexpected direction.
I tried to bring things back onto an even keel. "Fair enough," I
acknowledged, "I didn't choose my words carefully, but you know full
well what I meant."
"You don't wriggle out of it that easily," Barry continued
remorselessly. "I think that now having spent time with me as a woman,
you secretly would quite like to discover how you would look dressed
and made over. It is a similar reaction to the one I had in Manchester
after meeting cross-dressers for the first time."
I tried to answer him in a serious tone of voice, "I don't think that
is the case and, anyway, can we change the subject." My attempt to stem
the conversation was doomed to failure!
Barry continued to pile on the pressure. "Look, there are just the two
of us here this evening," he continued. "Let me make you over. No-one
will ever know and I think you will regret it if you let this
opportunity for a new experience pass."
How well he knew me. Not the dressing, that was a definite 'no-no'; but
it was true that I was always up for new experiences. Barry
instinctively sensed my doubts and pushed home his advantage. "I
'double dog dare' you!" he insisted. Now this was unfair. "Double dog
dares' were only offered when it was absolutely imperative. But once
the gauntlet had been thrown down there was no way I could resist
without breaking the habit of a lifetime and lessening myself in
Barry's eyes. I took a deep breath.
"Well as you now have me over a barrel, I guess I'll have to let you do
your worst!" I said with a resigned grin. Barry gave a very 'Sylvia-
like' squeal of delight and clapped his hands together.
"No time like the present," she said, pulling up her trousers. ('Barry'
had, of course, now vanished and 'Sylvia' was back in control).
"First things first," Sylvia stated firmly. "I know you don't have a
great deal of body hair but what you do have is going to have to go. I
am not going to be associated with a hairy woman!"
Well 'in for a penny, in for a pound,' so I trudged off to my bathroom
with a bottle of foul smelling hair remover that Sylvia produced from
one of her cases. I rubbed the stuff all over my body and waited, as
instructed, until I could bear the itching no longer. I then showered
off; watching my sparse body hair vanish down the plughole. I then
applied a coating of a flowery-smelling body lotion that Sylvia assured
me would get rid of any residual irritation. Next I gave my face a very
close shave.
Wrapping a towel round my waist I returned to the living room. "That
won't do" Sylvia scolded, "as a woman you should wrap your towel around
your breasts. OK I know you don't have any at present but that
shouldn't stop you getting the 'look' right. Sheepishly I readjusted
the towel.
"Time to get you into a gaff," giggled Barry - (for a moment my old
mate had reappeared as he contemplated the discomfort I was about to
experience.) He produced a flesh-coloured gaff. "It is brand new," he
reassured me, "never been worn." Well that was a relief! Barry showed
me how to push my balls back up inside my body and to tuck my penis
between my legs. He then held me pull the gaff into place. It was quite
a struggle and just as well neither if us was embarrassed about
touching each other's body.
The gaff was extremely uncomfortable and I told Barry so in no
uncertain terms. "You will get used to it," he insisted. "After a while
you won't notice you have it on. You can even go the lavatory without
taking it off. If you feel underneath you will discover the tip of your
penis just protrudes at the back." I felt, as instructed, and he was
right. "The only thing is, you are going to have to sit to pee like all
other women," Barry giggled.
Having got me safely trussed up, 'Barry' disappeared and 'Sylvia' once
again took control. She handed me a pair of lacy, white, bikini briefs.
I stepped into them and, having settled them in place was amazed at the
smooth, feminine front I presented. There was only a small, smooth
mound where my cock and balls had previously been.
Next Sylvia wrapped a white, satin waist cinch around my middle;
fastened the busk in the front; and started tightening the laces at the
back. She kept pulling and adjusting until I thought I would be unable
to breathe. "Please stop," I gasped, "I can't take any more."
"Don't be such a wuss," replied Sylvia. "Can I remind you that it was
you who said women have to suffer for their looks." Hoist with my own
petard I could only grin sheepishly - I had no breath left to
remonstrate.
Once I was firmly corseted, Sylvia helped me slip my arms through the
straps of a white bra and fastened the clips at the back. "You arte
going to have to learn to do this yourself" she warned me. ("Why" I
wondered. "I'm only dressing for this one evening.") A pair of silicon
breast forms were produced and slipped into the cups of 'my' bra. With
a bit of adjustment and tugging at my pecs a surprisingly realistic
cleavage was created.
By now I was curious to see what I looked like but Sylvia would have
none of it. "You will wait until I have finished," she admonished. "I
want you to experience the whole effect at once." I had to be content.
Sylvia next helped me put on a pair of sheer, nude tights. She
explained how I needed to gather them first, before carefully rolling
them up my legs. The sensation of sheer nylon on my newly smooth legs
was mind blowing and I was grateful - (for the first time!) - that I
was wearing a gaff, as otherwise I feared I would be displaying a
serious erection!
Once securely arrayed in my lingerie, Sylvia sat me down in a chair and
proceeded to work on my face. "Good, you have shaved really closely,"
she observed as she applied foundation and powder to my face. A pair of
tweezers was employed to remove a few stray hairs from my brows before
they were lined out using a makeup pencil. Eye shadow was applied to
my lids and mascara to my lashes. Sylvia then produced a pair of false
eyelashes and, in spite of my protestations, proceeded to glue them in
place. A little blusher applied to my cheeks and to highlight my
cleavage, and then it was time for lipstick. First of all Sylvia used a
lip pencil to draw in an outline which I could feel went outside my
natural lip line. Sylvia explained that this was to give me a fuller,
more feminine profile to my lips. She then applied colour using a thin
brush before sealing everything with an application of lip-gloss.
"Nearly there," Sylvia reassured me. "Just dress, shoes and wig to go.
Oh, plus jewelry of course." She had me stand whilst she helped me step
into a tight, floral-patterned mini-skirt. I never thought I would fit
into it, but the back zipper slid smoothly into place. A simple, long-
sleeved, violet-coloured top was slid over my head and gently pulled
into place. The scoop neckline showed off quite a bit of my cleavage
and Sylvia had to slap my hands to stop me trying to pull it up.
Sylvia then handed me a pair of nude-coloured pumps with a reasonably
chunky 3-inch heel. I sat and slipped them onto my stockinged feet.
Wearing nylon hose they went on easily although initially I had thought
they would be too small.
The final piece=de-resistance was a curly, auburn wig with blonde
highlights. Sylvia produced it with a flourish and I helped her by
holding the front in place as she set it firmly on my head and fluffed
it out with her fingers. "Mmm, auburn really suits you," she mussed. "I
glad I brought this wig along."
"You planned this from the start," I accused her. "It was always your
intention to get me to dress up as a woman on this holiday, wasn't it?
That is why you have so much luggage; you brought clothing and
accessories for both of us."
"Well I did rather hope you might be prepared to experiment," Sylvia
confessed sheepishly. But before I had time to reply, she continued,
"Anyway, let me just slip on a few items of jewelry and then you can
see what you look like." This rather took the wind out of my sails as,
having come this far, I was somewhat intrigued as to how convincing a
woman I would make.
A pair of clip earrings - ("you should really get your ears pierced",
from Sylvia;) a gold pendent on a thin chain and a chunky gold-coloured
bracelet, and Sylvia declared that I was ready for my debut.
Somewhat nervously I crossed to a full-length mirror. What would I look
like? Would I appear as some drag travesty of a woman or would I be
more convincing - as Sylvia was. The reflection in the glass caused my
jaw to drop. I wasn't anywhere near as glamorous as Sylvia, but I
didn't look half bad. In fact I could feel a stirring in my loins; I
was in danger of fancying myself! The padding and corseting had given
me quite a curvaceous figure and the wig and makeup totally altered the
shape of my face. As I was too gob-smacked to speak, Sylvia broke the
silence. "There, I told you that you would make a convincing woman" she
crowed in delight. "With practice we can get it even better. Shame we
forgot to varnish your nails but we do that later. What do you think?"
"I'm staggered," I finally managed to blurt out. "I know we are only
fooling around, but I never imagined you would achieve anything like
this."
"So you like it?" Sylvia pressed - (back in 'Barry' mode as she crowed
over winning our dare).
I had to be honest. "Yes I do like how I look," I confessed. "I never
thought for an instant that I would, but you have achieved something
amazing."
Sylvia preened, "So you will do it again?" she pressed.
"No," I retorted sharply. "I agreed to play around for this one night
only."
Sylvia pouted and looked dejected. "Never say never," she giggled. "In
many ways your reaction is similar to mine the first time I saw myself
dressed. I sincerely hope you won't stop now but at least take the
experiment a little further."
Barry has always known when he has gone far enough and when to cease a
discussion, so he deftly turned the conversation; "Well I was thinking
of suggesting we go out to a bar for a drink but I guess you aren't
ready for that yet, so what say you and I crack open a bottle of
prosecco and we toast your new 'look' here on the terrace." 'Sylvia'
was smiling so sweetly I hadn't the heart to deny her so we opened a
bottle and sat in the sweet night air enjoying our wine. We didn't say
much and I found myself starting to enjoy the sensation of wearing
soft, silky garments; the tug of my bra straps; the swish of nylon an
nylon as I crossed my legs. I found that instinctively I was tugging at
the hem of my skirt to ensure I did not reveal anything I ought not.
Sylvia/Barry grinned enigmatically as (s)he saw how I was beginning to
get into role.
Eventually we finished the bottle and decided it was time for bed.
Sylvia helped me undo and get out of my unfamiliar clothes. (I thanked
and stopped her when I got down to tights and panties; I could manage
those on my own thank you very much!) She also explained what I needed
to do to clean my face of makeup and provided the necessary lotions and
cleansing pads. "Put you wig on this" she instructed, handing me a wig
stand. (This pulled me up short as I had got used to the feel of
longer hair and had almost forgotten I was wearing a wig.)
As I retired to my bedroom, laden down with all these necessary
feminine accessories, Sylvia proffered me a slinky nightdress. "Sure
you wouldn't like to try sleeping in this?" she said teasingly.
"No way," I responded firmly and strode manfully into my bedroom - (not
that easy to do when your backside is on view through the gauzy fabric
of a pair of knickers and tights!)
Once safely in my bedroom, I breathed a sigh of relief and took off my
remaining feminine garments. I was careful to make sure the wig was
correctly placed on its stand. Even though I had no intention of
wearing it again, it was very pretty and I had actually quite liked the
sensation of hair falling over my ears and brushing my neck. Having
taken the wig off, I discovered I had also forgotten to remove my
jewelry, so off came the earrings, pendant, bracelet and rings. Next I
gently rolled my tights down my legs and took them off, taking care not
to ladder them. It took but a moment to slip out of my knickers, but
extracting myself from the embrace of the gaff was a bit more of a
challenge. However, I finally managed to divest myself of the
constricting garment and breathed a sigh of relief as my balls popped
back into place. I massaged myself gently. I was a bit numb down there
but no permanent harm seemed to have been done to my anatomy.
It took several minutes to remove the makeup and clean my face of
residual traces. At Sylvia's suggestion, I applied a moisturizer to my
skin. Climbing into bed I fell asleep smelling the floral scent of all
the lotions and potions and with my brain teeming with wild dreams of
me dressed in female finery.
The following morning I showered and dressed - in my normal male
clothes - ready for another day exploring the secrets of Venice. Barry
was already up - dressed as Sylvia. She gave a moue of disapproval when
she saw how I was dressed. "I had hoped you might be prepared to take
our experiment a little further this morning, but clearly you aren't!"
"Sorry," I replied. "I did actually enjoy the experience of being made
over as a woman last night, but as I said at the time, that was a 'one
off' and today it is back to normal."
"Spoil sport," moaned Sylvia, but she didn't press the point and after
breakfast we set off of to see what new treasures we could find.
On our way back to the apartment at the end of the afternoon, we walked
through a district we hadn't been to before. Suddenly Sylvia let out a
squeal of delight. "Do you see that restaurant; isn't it dreamy; oh we
must come here tonight." The restaurant in question was tucked away
behind a high brick wall. A small doorway led into the most delightful
garden.
"I bet this looks lovely at night when it is all lit up," Sylvia
enthused. It was truly a beautiful setting and a quick scan of the menu
showed that they offered a considerably better than 'Tourist' menu. I
had no hesitation of agreeing with Sylvia, so she scurried away to find
someone who would take our booking. "They are fully booked for the
early part of the evening" Sylvia informed me on her return, "So I have
booked us a table for 9:30 pm. I hope that is OK with you?" I assured
her it was fine for me and we proceeded back to the apartment in a
really good humour.
As we now had a few hours to kill, I suggested we have a lie down. I
for one was tired from traipsing the streets of Venice and the thought
of a shower and forty winks was very attractive. I did indeed drop off
and woke about 6:30pm much refreshed. A quick visit to the bathroom to
freshen up before I slipped into my dressing gown and picked up my
journal to record the findings of the day. But I couldn't settle to my
writing. This happens sometimes and I have long since learned that when
the words aren't flowing you cannot force them. In such circumstances
it is better to leave off and return to the task later.
So I put my journal aside and looked around for some light reading
matter. My eye fell upon the auburn wig on its stand. "I know that last
night I thought that colour hair suited me," I thought to myself, 'but
I can't really remember how it looked in detail." Almost without
thinking I took the wig off the stand and adjusted it on my head. From
there it was but the work of a moment to add the dangly earrings and
pendant necklace.
The wig did indeed suit me, and I was standing there admiring my
reflection in the mirror when there was a knock on the door. I didn't
even have time to blurt out, "Hang on a minute," before the door opened
and Barry entered wearing 'Sylvia's' nightdress and robe. "I just
wondered whether you were ready for an aperitif," he started before he
fully took in what was before his eyes. There I was, clad only in my
boxers, a curly, auburn wig, and jewelry. "Well," she said with a
mischievous grin, "you didn't take long changing your mind about
tricking yourself out in feminine finery!"
"It's not like that," I tried to explain, but to no avail. To be honest
I didn't have much of a leg to stand on. As Barry said, he had me "bang
to rights!"
I quickly pulled on my dressing gown and went to remove the wig. "Don't
do that" Barry interjected. "You look great. Come and have a drink and
enjoy the feel of longer hair."
Sheepishly I followed him out onto the terrace and he poured us each a
glass of wine. We must have looked a pretty pair. There was me in a
man's dressing gown with long auburn hair and jewelry, whilst Barry was
dressed in a nightdress and negligee but with short, close-cropped
masculine hair. Neither of us was wearing makeup.
We sat silently sipping our wine until Barry finally broke the impasse;
"Go on, admit it, you enjoyed becoming a woman last night and want to
do it again don't you?" he challenged.
As I could think of no convincing repost I shrugged my shoulders and
muttered, "I guess so."
Barry jumped up excitedly, clapping his hands. "I knew you would come
round to the idea in time," he chortled. "Now you are going to have to
come out to dinner tonight en femme."
I tried to protest but it was no use. Barry was adamant and I couldn't
really blame him. After all nobody had forced me to put on the wig and
jewelry. Finally I accepted the inevitable and agreed to go out with
him in feminine guise.
By now it was about 7:30, which gave us two hours to get ready. "We
will need all of that," Barry announced firmly and, taking me by the
arm, marched me into his bedroom and sat me down in front of 'Sylvia's'
dressing table. "This time you had better look how I do your makeup,"
he announced. "Look and learn so that you will be able to do it for
yourself in future."
Well, it wasn't going to be easy to argue there wasn't going to be a
'future' dressing after today, so I kept my mouth shut and tried to
follow Barry's moves as he made up my face.
Actually the principles didn't seem that complicated although I could
see that a lot of practice would be needed before I could achieve the
same degree of excellence as he did.
Once I was made-up, Barry suggested I look through his wardrobe to see
if there was anything that caught my eye. "You might as well start
enjoying trying on different clothes whilst I get my face on" he
instructed. Until I started rummaging I hadn't appreciated just how
many clothes Barry had brought with him on holiday. I pulled down
hanger after hanger but nothing seemed to catch my eye. Everything I
looked at seemed either to tight and revealing or too brightly coloured
and likely to attract attention. (To be honest I hardly gave a thought
to what I was doing; here I was, a confirmed heterosexual, considering
which dress to wear out to dinner! And last evening I had been adamant
that my dressing up had been strictly a 'one off').
Finally I came across a simple, cream, loose-fitting, mid-calf skirt
and a pale blue, three-quarter sleeve, silk blouse. I was looking them
over when Barry appeared behind my shoulder - except 'Sylvia' was now
in the driving seat. Whilst I had been preoccupied, Sylvia had
completed her makeup; dressed in her lingerie; put on her blonde wig
and put her hair up into an elaborate French pleat!
"Oh that is dreamy," she enthused, "and so 'you'. You just have to wear
it. Come on, let's get your underpinnings in place." Suiting action to
word, she handed me a clean gaff and panties. This time I managed to
tuck myself away without her assistance. Light tan tights; the corset I
had worn the previous evening; lacy bra and breast forms were all soon
in place. Sylvia helped me into the blouse and steadied me as I stepped
into the skirt and zipped it up. I slid my feet into a pair of strappy,
silver evening sandals.
For herself Sylvia chose a form fitting, sleeveless, knee-length
sheath-dress in a floral fabric of red roses on a white ground. She
selected a pair of spike-heeled white pumps. "Tonight we need to
varnish your nails" she announced firmly. I was forced to sit quietly
whilst she painted my fingernails a deep, sexy pink. "We forgot your
toes and, as they are visible peeping out of your sandals, we can't
have that!" was her next firm pronouncement; so I had to take off my
sandals, wriggle out of my tights and patiently allow her to colour my
toes with a deeper shade of varnish. "Have some wine while we let them
dry," Sylvia said, passing me a glass. It seemed to take ages for the
varnish to dry, but eventually Sylvia declared herself satisfied and I
was allowed to struggle back into my tights and shoes.
"Now what are we going to call you as a woman," Sylvia mussed. "'Terry'
is no longer appropriate and 'Teresa' sounds a bit formal. I know, how
about 'Tessa'? That is both pretty and easy on the tongue."
I didn't have any opinion - I had never thought to have a female name!
- So I shrugged my shoulders and agreed.
"No, seriously," Sylvia continued, obviously upset about my lack of
involvement in choosing a female name. "This is what you will be called
from here on when you are dressed, so it is important we choose
something you like and with which you will be comfortable" I took a
deep breath and tried to focus my thoughts. In fact 'Tessa' was a
pretty name and after some thought I told Sylvia I was genuinely happy
to go along with her suggestion. She seemed pleased. "Good," she said,
"I like it too and it does somehow seem to suit you."
"Now, you will need a handbag for all your bits and pieces" Sylvia
announced next and, rummaging in her wardrobe, produced a cream
shoulder bag. I was amazed at all the things she insisted I needed to
put in it. But then, I no longer had pockets into which to stuff
handkerchiefs, cash, credit cards, etc. Then there were the
embarrassing feminine products; a couple of tampax; a packet of
condoms; lipstick; powder compact; and so forth. I did query why I
needed condoms and tampax only to be informed that no self-respecting
young lady would dream of going out unprepared for all eventualities.
"We had better each take a shawl," Sylvia advised. "It could get cool
later." She found me a soft cream pashmina, whilst choosing a black and
red silk number that went well with her dress.
Now fully and correctly attired - (at least as far as Sylvia was
concerned; I was much more dubious) - we sallied forth and set off for
our restaurant booking.
Stepping through the front door of our building into the street was the
hardest thing I have ever done. I was so nervous I was close to
hyperventilating. Sylvia took my arm in a companionable manner. "Deep
breathes Tessa" she instructed. "Honestly you will be fine. I know you
are scared of being 'read' but you look really great and I don't think
that is likely to happen. And what if it does? The worst that can
happen is that you get laughed at a bit and laughter never left any
permanent scars!"
"But what if we come across a gang of homophobic toughs and get into a
fight?" I reposted.
"Fair point," Sylvia confessed, "and in parts of some cities I agree
that would be a real possibility. But we are only walking through
tourist Venice. You have escorted me whilst I have been dressed as a
woman and have we encountered any such gang?" I had to admit we hadn't.
Our experience of walking round Venice at night had been very calm and
peaceful.
So, with Sylvia setting the pace, we gradually made our way towards our
restaurant. After some minutes I started to calm down. I could now
hear the click of my high heels striking the flagstones. It was a most
weird experience. After about fifteen minutes walking we arrived at the
restaurant and, without allowing me to pause and reconsider, Sylvia led
me through the door in the high brick wall and into their garden. It
had been pretty in the daytime; at night it was magical, lit by candles
and small lanterns. Nearly all the tables were occupied but, when
Sylvia gave the Head Waiter her name, we were shown to a secluded table
set in one corner of the garden. I sank into my chair with an inaudible
sigh of relief; our table was well away from the main body of diners
and discretely lit. This gave me the best chance of getting through the
meal undetected.
A waiter gave us each menus and we discussed quietly what dishes we
would like. Sylvia chose a goat's cheese tart for her starter, with
linguine vongole as her main course. I'm not too keen on shellfish, so
I joined her in the cheese starter and followed it with veal cooked
with butter and sage. Sylvia suggested she place the order as I hadn't
had any real practice at adopting a feminine speech pattern. I was only
too happy to agree!
The meal was as delicious as the garden setting and we took our time
over our food; accompanying it with a bottle of excellent valpoicella
and finishing off with coffee. By the time we had finished our meal I
was much more relaxed and was able to settle back and enjoy both the
food and some light bantering with Sylvia. (Her 'Barry' side could not
resist teasing me about my new role and status. I tried to give as good
as I got but fear Barry came out on top overall!)
Sylvia paid our bill and at about 11:00 pm we strolled gently back
through the quiet streets and squares to our apartment. Once safely
indoors I breathed a sigh of relief and collapsed on the sofa. "Well
done," Sylvia congratulated me, "you handled that brilliantly. Even I,
who know you so well as 'Terry' was willing to believe you actually
were 'Tessa' by the end of the evening."
This was praise indeed and tears welled up in my eyes.
"See, even your reaction to praise is typically girly," Barry teased
me. We both laughed and hugged. Barry insisted we have a glass of
grappa as a nightcap to toast my success. "To many future outings for
Tessa," he declared, raising his glass. Part of me hoped he was wrong
and that this would be the final time I dressed as a woman, but I was
also conscious that another part of me was reveling in my achievement
and wondering if further experimentation might not be a good idea. I
went to bed to sleep on it!
The following morning Barry was in my room early, before I had time to
get up, wash and dress. "Now you are going to be 'Tessa' today aren't
you?" he enquired anxiously. "If you insist," I capitulated with a
grin.
"Oh I do, I do," (s)he squealed with delight and hurried back to her
room to get dressed whilst I undertook my ablutions. After shaving
closely and showering, I set about dressing myself as a woman for the
first time on my own. I managed gaff, panties, bra and tights without
too much difficulty and even managed to fasten the busk of the waist
cinch. I couldn't tighten the laces sufficiently however and had to ask
Sylvia for her help. She was only too delighted to lace me up until I
was gasping for mercy!
"Pick yourself something pretty from the wardrobe" she said. "I would
suggest a cotton or linen dress with cap sleeves and a knee-length
skirt. That way we can go into churches without offending the old
ladies guarding the door." I took her advice and picked out a simple
shirtwaist dress in pale green linen. It went very well with my auburn
hair. Sylvia insisted I try putting on my own makeup. I made a fair
stab at it, but gratefully accepted her offer of help to 'fine tune'
the finished product. I put on a pair of cork soled, wedge heeled
sandals and used the same cream bag as I had the previous evening.
Simple daytime jewelry and a squirt of perfume and we were off.
I was much more relaxed this morning, even though the risk of being
'read' in daylight was probably greater. We explored some of the less
frequented churches in parts of the city not usually visited by day
trippers - as so many of Venice's visitors are. We had a peaceful and
very satisfying day - including lunch at a canal side caf? where we
were served without any fuss and where, in fact, the youngish waiter
started flirting with us!
After lunch we found ourselves walking through an area of small local
shops. Sylvia spotted a little jewelry shop and dragged me inside. "Now
you are going to get your ears pierced," she announced. "I insist and I
am not going to take 'no' for an answer. Lots of blokes have pierced
ears these days, so you won't look out of place when you get home and,
in the meantime, you can have the fun of choosing your own drop
earrings." Once again I could see that resistance was useless, so I sat
there whilst the shop assistant put two piercings in each ear. (I
thought this a bit excessive; one earring I might get away with at
home, but two in each ear; that would take some explaining.) Still, by
now it was too late to argue so I gave in with good grace and admired
my reflection in the mirror with zircon studs in the top holes and
small gold hoops in the lower. The assistant was a bit unhappy about my
not starting off with sleeper earrings, but Sylvia assured her - in
fluent Italian - that I would take proper care of my new piercings and
would certainly wear sleeper studs at home.
We returned to the apartment mid-afternoon as my calf muscles hurt and
I needed a rest. "Honestly, it does get easier with practice," Sylvia
reassured me. "I remember how painful I found heels after a couple of
hours when I first started wearing them. You have done exceptionally
well to have lasted out as long as you have."
I kicked off my sandals but retained the rest of my feminine attire as
I picked up my journal and went out onto the terrace in my stockings to
write up my notes.
Barry/Sylvia wasn't tired and decided to go out again for a wander on
her own. She said that whist she were out she would find us somewhere
to eat for the evening and promised to be back no later than 6:00pm.
She was as good as her word; she found us a sweet little place on one
the Cannaregio canals. The proprietor and his wife were wonderful
hosts. She waited table whilst he cooked. The food was simple but
authentically Venetian; we had a great time. In fact this restaurant
became one of our favourites and we went back several times. After a
few visits Flavia - (for that was the wife's name) - hesitated one
evening after taking our order.
"Francesco and I have been wondering," she started tentativel