Note. This is an idea I started playing with over 30 years ago when I
was an undergraduate, after I met my first transsexual in a supermarket
round the corner from the slum bedsit where I was living at the time.
Winters Blessings
By Trish
It was in 1996 when I was finally freed from nosy social workers,
guardian's and boarding school. Having been orphaned in my mid teens I
was technically classed as in care but I was never in the system as
such, I was not from a broken family or anything like that, I was just
unlucky. First my dad, a lieutenant commander in the Navy lost his life
when his ship was hit in the Falklands conflict. Then my mum who was a
doctor in the Royal Medical Corps was killed in a helicopter accident.
I was fifteen when mum died and at boarding school, but because the
military look after their own I remained at school and did not go into
the state system. Instead a family friend from the Royal Medical Corps
volunteered to act as my guardian until I was old enough to go to
university. After the restrictions of boarding school and my army
officer guardian getting to university was great. For the first time in
my life I had genuine freedom and I worked hard, but also made the most
of the social activities on offer until my course workload began to
increase.
Although I enjoyed the madness of student housing mid way through my
second year I realised I need to make a choice between partying and
college work. As both my parents had been serving officers who died in
the line of duty I had a considerable inheritance tied up in a trust
fund which allowed me to move out of the student ghetto close to the
University and into a nice one bedroom flat on the outskirts of the
town. The flat had a two great advantages for me, for one it was far
enough away from the student union to remove the temptations of the
union bar and the second was having the privacy to indulge in my secret
hobby. Although the primary reason for passing my bike licence during
my first year was to have transport so I could get away from the
distractions of student housing I also chose to ride a bike because no
one would ever think it odd if a biker type had long hair and pierced
ears!
I was riding home during early December towards the end of the autumn
term and the route I usually took from college was closed because of a
gas leak. This was a bit of a problem as I wanted to get to the
supermarket and the diversion took me over the river through a part of
the town I did not know very well. Guessing correctly that the
diversion was going to take me out to the ring road I was trying to
decide if it was worth riding half way back into town to Tesco's when I
saw a Gateway where I could do my shopping.
In those days the internet was still in its infancy so other than the
odd sensationalised newspaper article I was not really aware that I was
not alone in my hobby, or that transsexuals existed until I went to
University. Other than on the internet I had never seen a transsexual
in my life until I walked into Gateway that afternoon.
I was collecting the usual staples and was considering treating myself
to something nice for dinner when I saw her walking down the aisle
towards me. Her make up was rather heavy, she was tall and quite
mannish under the supermarket uniform dress but to my eyes she was also
beautiful. Like I said I had never seen a trans person in real life and
I was gob smacked by both her presence and bravery. As she walked
briskly past me I saw her name badge said Cheryl. Needless to say from
then on I started using that supermarket rather than Tesco's. I guess
it was the end of the month between Christmas and New Year before I
said anything to her, but eventually she happened to be on the
checkouts when I came to the tills and exchanged a few words with her.
Finally able to look at her close up I guessed she was a few years
older than me and spoke with a surprisingly feminine sounding southern
accented voice. I had thought she was attractive when I first saw her
but now I was close up I was smitten, and I prayed my helmet hid my
blushes as I paid for my shopping. Anyway to cut a long story short
over the month following we chatted over the tills a couple more times
and got to the point of exchanging smiles when I walked in.
I really got to know her one really foul afternoon in late January. I
was riding home from college when I saw her on the side of the road
struggling with a flat tire. Wearing only a light jacket to protect
herself from the icy wind-driven rain she was trying to get the jack
under her car. Stopping my bike in front of her car I guess I must have
looked pretty intimidating in the twilight because as I came towards
her, she looked fearfully through the pouring rain in my direction.
Pushing up my visor I said, "Hello Cheryl, can I give you a hand?"
Clad in from head to toe in my black waterproof suit, for a moment she
looked at me like I was from another planet and then recognition
bloomed in her eyes as she said in a shivering tone, "Oh it's you, the
student with the motorbike."
"Yeah, I'm Alex by the way," I said. "Here let me do that as I wont get
soaked lying on the deck."
Protected by my waterproofs it only took me a couple of minutes to jack
the car up and switch the wheels. A few minutes after that the car back
on to the floor and ready to drive, and closing the boot I said
cheerfully.
"Well that's my good deed done for the day."
"Thanks Alex that was really good of you," Cheryl said, "I could kiss
you but..."
"No need, but I'd enjoy tha..." I broke off what I was saying when I
noticed that she was absolutely soaked to the skin and shivering
violently. "Christ your soaked."
"Yeah," She said through chattering teeth, "I know."
"Look don't take this wrong, and I'm quite harmless but I only live
round the corner and you need to dry off and get warm."
"No Alex, thank you for the offer, but trust me you don't want to be
seen with the town freak!"
"Cheryl, listen to me the way you're shivering you're only a step from
hyperthermia and its too wet and too cold for any of that sort of
nonsense just now. You need to get warm and soon, oh and for your
information I don't think you are a freak, a pervert or anything like
that, hell I think you're incredibly brave, certainly braver than me."
She looked at me shaking.
"Look, I know you're a bit taller but I think I've got a cotton skirt
and top that will fit if you want to lob your uniform in my dryer."
That stopped her. "Really?"
"Yeah," I said blushing brightly.
"You!" She exclaimed through her chattering teeth. "You're a
crossdresser?" I nodded as she said, "So that's why you're always so
nice to me when you come in."
"Oh you noticed." Under my helmet my blush got even brighter as she
nodded, which reassured me enough to admit, "Yeah, I like dressing as a
girl, so unless you enjoy driving in soaked clothes that are going to
chill you to the bone my offer still stands."
"I'll come," she said getting into her car. I could feel her eyes
watching me with interest as I threw my leg over my bike and thumbed
the starter.
When I said round the corner I meant it as two junctions up the road I
turned left in to the car park of the modern four flat development
where I lived. As each flat had its own outside door, only minutes
after her wheel was changed I led her into my place. Telling her as I
closed the door pulling my helmet from my head.
"If you straight up the stairs my bedroom is the door on the left,
there is an ensuite door into the bathroom where you can get out of
those wet things. You'll find a clean towels in the bathroom cupboard
and I'd recommend you have a shower to warm back up."
I gave her a grin and said, "Don't worry I have a good quality shampoo,
conditioner and body wash, but it's your choice," and knelt down to
undo my boots and waterproofs leg zips.
"Just go up and get warm, I'll be a while fighting my way out of this
lot. Tea or coffee when I am done?"
"Coffee, white please," Cheryl said. Her teeth were chattering, and she
was shivering violently as she hung her wet jacket next to my helmet
the wall hooks next to the door.
As she started up the stairway I added, "If you lob your wet stuff out
of the other bathroom door I'll pop it in the dryer while you help
yourself to anything that fits in my wardrobe."
Glancing back at me she gave me a smile her weather washed face looking
more clearly more masculine as she said, "I will Alex, thank you."
By the time I had got out of my boots, wet socks, waterproofs and
leathers, and padded barefooted up stairs I could hear the shower
running. On the floor outside my bedroom was her wet uniform. Picking
it up I walked into the lounge kitchen checking the labels to see that
I could safely put it all in the machine.
As usual my first move was to put the kettle on, and then I removed the
washing I had put in before I went to college. Dumping it on the
counter I pulled one of my student girl uniform cotton skirts from the
clean washing and pulled it up my legs blushing to myself when it
occurred to me that I was about to let someone see me in a skirt for
the first time. Cheryl's uniform was covered in road grime and make up
runs so rather than just drying it I put it in on a wash and dry cycle,
with my wet socks and made my self a mug of tea. Sorting and folding my
clean washing into two piles, I could hear my hair dryer in the back
ground as I separated my ironing from my bike thermals and fleeces.
About twenty-five minutes after she arrived Cheryl walked in the living
area commenting. "I like your flat Alex, when you said your place I was
expecting some student slum not a place like this!"
I was bending down putting the oven on for the casserole I had made
that morning and I looked looked up to see her looking much warmer than
when she arrived. She was wearing a pair of black leggings, another of
my student skirts and a baggy university sweatshirt. Rather than the
heavy full face make up and elaborate hair style she wore at work, her
hair was tied back in a lose pony tail and she had repaired her face as
much as she could. Giving me wide smile said. "Thank you Alex, I did
not realise how cold I had got and that shower was a god send."
"You're welcome," I grinned, "but for next time keep a good waterproof
in your car." I passed her a mug of coffee over the kitchen counter
that divided it from the lounge area saying, "Have a seat. Your uniform
will be about half an hour as I had to give it a wash because it was
covered with road shit and make up runs."
Cheryl laughed and said, "Very domesticated," adding with a chuckle as
she took the coffee, "No wonder you had that maids uniform in your
wardrobe."
"I could not resist buying it," I admitted, embarrassed about seeing
that and letting her see me in a skirt. Trying not to show how
embarrassed I felt I picked up my mug of tea and joined her on the
sofa.
Cheryl laughed lightly. "Nice skirt Alex but it really does not go with
the rest of your look."
"I know," I said with a blush, "but my leather jeans were wet, you were
in my room and I did not want you to find me in my knickers!"
She gave me an arch look and said with a chuckle, "How do you know I
would not have liked that Alex?"
"I didn't, but I'm not that much of a tramp to walk round in my undies
in front of someone I know over a supermarket till!"
"So tell me what's your girl's name?"
"I've not got one," I said.
"Okay what would you like to be called?"
"I don't know... I've never thought about it?"
"You should," Cheryl said giving my leg a pat before asking, "So when
did you discover you liked to dress as a girl?"
"I can't remember, early enough that I can recall being jealous as hell
of the girls clothes at primary school, but I never got to actually
dress up until played Juliet in boarding school play, which was
wonderful but after the misery the other boys put me through I did not
dare put myself forwards for another girls roll."
Cheryl nodded.
"Then when started at the university, I was living in a shared house,
so I had no chance of dressing even though I had by then bought myself
a few things. Anyway after a year and a term of living in the student
ghetto around the university, I got the solicitor to release some of my
inheritance to get this place, and buy a bigger bike to get to college
on."
While I was telling her my dressing history Cheryl was sipping her
coffee and looking me carefully over. I was relaxing a little by now
and admitted that I did not start riding bikes because I wanted to be a
'biker' but because it was the perfect camouflage for my long hair and
earrings.
Then out of the blue she commented, "You know I bet you'd look great
dressed up, miles better than I did when I started! Do you fancy going
and dolling yourself up for me?"
I blushed and said, "If you want..."
"Oh I do," Cheryl said giving me a naughty grin. "I'd ask you to wear
that maids dress, but I think I'll leave that until we know each other
a little better and you've got your name, so how about just dressing as
you would for a normal evening?"
"Okay." I nodded red-faced forgetting all about putting my casserole in
the oven. "Help yourself to another coffee if you want, you'll find
everything next to the kettle, and the milks in the fridge."
I did not have a clue if I was doing the right thing but I did as she
asked. Grabbing a quick shower it took me about 40 minutes to get
changed. I could have done it faster but I decided to crimp my hair. It
was my favourite way of doing my hair at the time, and it was a popular
style with my 'hippy girl' female course mates. Holding my hair back
with a couple of hair slides I carefully did my make up. I was not very
good at make up, but after a lot of practice I was able to make up my
face in roughly the same way as one of the girls on my course did hers.
Swapping my studs for a pair of long dangling earrings, and fixing my
lips with a fashionably red lip stick I slipped my feet into the pair
of ballet style flats I wore as slippers and turned to the mirror.
Checking my reflection I took a deep breath and walked back into the
lounge to face Cheryl.
"WOW!" She exclaimed looking at me with an ear to ear grin, "I thought
you'd look good but you're bloody gorgeous and definitely not an Alex
any more!" She spun her finger indicating I should give her a twirl,
"My god, you might have been born an Alexander but you make a great
looking, Anna or may be Angie?" She had a musing tone in her voice as
she went though a couple more names beginning with A before coming up
with, "Abigail, yeah Abigail definitely an Abigail. I'll call you that.
What do you think of Abigail, or Abby for short?"
I shrugged and said, "I like it."
Cheryl gave me a pleased look and said, "Good, then from now on as far
as I am concerned you're Abigail."
Her eyes were all over me, examining every inch before she said, "Fetch
me another coffee Abby, I want to watch how you move so I can find out
what I have to teach you before I can take you out, because your too
good-looking to hide yourself behind your front door!" She giggled as I
walked to the kitchen and commented. "You might look great but your
posture is all wrong, and you're walking like a bloke... You need the
pair of shoes with at least a three-inch heels for starters, not only
will the heels make your legs pop but they'll also make you more aware
of your posture, which helps develop a feminine sway into your walk."
Making Cheryl another coffee like she asked I was listening to her
chattering away about the differences between male and female body
language and presentation when I noticed that the casserole was in the
oven and said, "Oh you put my casserole in, I'd forgotten about that?"
"Yes, I saw it in the fridge and noticed the oven was on. So I put two
and two together and popped it in," Cheryl said absently watching me as
I made us the hot drinks.
"Since your uniform is still drying and you put my dinner in, do you
want to stay for a bite to eat?"
"If it's not an imposition, I'd like that."
"It's not," I said carrying the drinks back into the lounge.
We spent the next four hours talking. I told her how I lost my parents
and found out in return that she was from Cambridge and lived 20 miles
away in the regional centre. She was six years older than me and was an
art school graduate who had worked as a photographer before she started
her transition. She explained that she was now fourteen months into her
real life test where she had to live and work as a female for at least
two years before she could be considered for the surgical procedures of
gender reassignment.
"I've not made up my mind if I'm going to go all the way, but it will
be nice to know I can once I've passed my RLT," She said smiling, "not
that I need to think about if yet, because I want to get my boobs then
face done and then I'll think about starting saving up for the final
surgery."
I nodded and asked about the RLT?
"Its great, but also a real pain in the arse," Cheryl admitted,
"because they want to see certain things, and its easier to do what
they want than argue with them. That's why I took the job at the
supermarket so I had an in roll income, while quietly keeping my photo
studio going," She gave me a naughty grin and admitted that she could
have easily got a better paid gender appropriate job but the
supermarket worked better as typically feminine employment for the
psychologists who had to pass her social and psychological adaption to
proceed to the next step of the reassignment program.
She was honest about the side effects she had felt since her hormone
treatment had started affect her over the last nine months or so. She
also made no secret of her frustration at the rather dated version of
femininity that the psychologists expected her to portray. "I do what
they want, and how they want it, but I don't like it very much. They
seem to think we all should adopt a super feminine 50's home maker type
gender role, and if I let them know that I'm actually business minded
and competitive it would be tantamount to resigning from the program."
"So how did you get on the program?" I asked full of curiosity.
"That part was actually remarkably easy. After god knows how many years
of questioning my gender and orientation I went to talk to my doctor
about how twisted up I felt and he referred me to a gender specialist.
I guess I saw her for two or three sessions before she agreed to let me
go on the program," Cheryl said with a smile. "I was on a very light
hormone regime and an anti-androgen to knock back the testosterone for
the six months or so before I started my RLT. Once I started that they
increased my hormone dosage, and have done the same every six months
since. I noticed the psychological effect of them first when they upped
my dosage first time. I lost a lot of my emotional control, and had
some hellish mood swings for the first few months until my body adapted
to the changed from testosterone to oestrogens, but I did not feel any
physical changes until almost year after going on hormones," She
giggled, "My nipples got really sensitive and then tissue began to
build behind them."
After exhausting that topic for now, Cheryl looked at me and asked if I
had a girlfriend?
"No, not at the moment," I admitted, "I've been more interested in my
studies and dressing myself than girlfriends."
"Boyfriend?" Her eyes glittered with interest.
I blushed and admitted, "Not since school."
Cheryl nodded. "So no friend then."
My positive reply brought a smile to her face, which gave me the chance
to ask her the same question.
"Not recently for either."
Before I could probe any further she started telling me how she started
dressing. Much to my amazement she revealed that there were clubs for
'girls' like us in London. Seeing my excitement at her revelation she
teased, "Play your cards right Abby and I'll take to some of them."
In the end it was gone nine before she said. "Oh god look at the time I
better get off home! Thanks for a lovely evening Abby, its been really
nice to spend an evening with someone who's not trying get in my
knickers so they can brag about shagging the local sex change freak."
"You're no a freak!"
"Course I am!" She laughed. "You just don't see it because you're one
too!"
As I had washed and dried her uniform I suggested that rather than risk
getting it wet, she might as well as go home in my things.
"I'll be home from late afternoon just drop them in when you finish
tomorrow."
"I won't be finished until eight tomorrow Abby, surely you'll be out on
the town like all the other students on a Friday night?"
"They might be, but no one who wants a good grade from my course will
be, we've all got a mountain of work to get finished. We've final
projects due in at the end of term, as well as a half-dozen assessed
papers for this terms course work," I said pulling a face. "I'm in my
final year and they really pile the work load on this term."
"What are you studying?"
"History," I said, "which is lots of reading and even more writing.
Thank god I can type!"
Cheryl nodded, and then said, "Okay I'll drop in on my way home, how
about I pick up some dinner since I ate what you had planned to have
tomorrow's dinner?"
"Up to you, but I don't mind cooking something. I find it a good way to
clear my mind after college," I said following her down the stairs to
the door.
"Okay, if you insist," she said not putting up a fight.
"Anything you fancy?" I offered.
"No surprise me," Cheryl said adding, "Have it ready for half eight."
Giving me a look as she pulled her still damp jacket on and then with
out an warning suddenly grabbed me. Holding me in her arms she gave me
a very serious kiss on the lips, which made me want to melt as she
said, "I've wanted to do that all night! Thanks for being such a star
Abby and I'll see you tomorrow night."
With the power of Cheryl's kiss still making me zing when I went to bed
I found it hard to get to sleep as my mind was full of her. However
once I feel asleep I actually slept very well, and woke up the
following morning to one of those perfect winter days. Rather than
lingering like the weather guesser forecast the rain had blown through
over night leaving the sky crystal clear and the weak winter sunshine
felt great as I rode into town. As my big waterproof suit was still wet
from yesterday I risked just wearing my leather's. It was a bit risky
because with the rain blowing through I early I was a little worried
about the snow forecast for the weekend would arrive earlier than the
radio weather guesser predicted, and made up my mind to head home
early.
Thankfully I had a lot to occupy my mind and it was almost three in the
afternoon before I got out of college. The weather was still dry but
the wind had changed direction and was coming in from the north-east
driving the temperature down like a falling stone! Deciding to get home
as soon as possible when I saw how the hills to the north, which had
been crystal clear during the morning were now clearly white through
that hazy distortion you get when you're looking at something through
falling snow. For once I did not head home the longer but quicker way
past Gateway, and instead went through the town centre to Tesco's as it
had a petrol station where I could fill my bikes tank and get my
shopping at the same time.
I was shivering when I got home and the sky had taken on that heavy
grey snow is coming colour so it was a relief get myself and my bike
safely home. Getting in I removed my helmet and gloves, before going
back outside to lock and protect my bike with a weather cover just in
case it did snow more heavily than the dusting they had forecast for
us.
Rather than risking messing up my outfit I made a chicken pie, chopped
a few potatoes so I could braise them in the oven at the same time as
the pie was cooking. With dinner fixed and a bottle German wine cooling
in the fridge in case Cheryl decided to stay over and have a drink
rather than risk driving home the now falling snow.
Finally with dinner prepared I went to get ready.
Although I was tempted to wear the maids uniform I had bought mail
order from a hotel supply firm instead I chose a little black dress I
had found in Oxfam. Under the dress I wore my best lingerie, a pair of
black stockings and my only pair of black high heels. I crimped my hair
again but this time held it back with an Alice band before I tried to
do my make up. I completely failed at doing a more complex evening make
up and had to wipe it off and start again. Telling myself to relax I
went and popped the dinner in the oven before doing my make up again
and this time I did it like I had the night before. By now it was gone
seven and I barely had time for a cup of tea as I set the table before
Cheryl was at my door a half hour earlier than I expected, and when I
opened it for her it was snowing, boy was it snowing!
"Come in," I said, with a welcoming kiss adding, "Dinner's going to be
about an hour, as you're a little early."
"Yeah, as I was in early a couple of days last week and the boss
decided to let me go early because of the roads are getting bad,"
Cheryl said handing me a case before she shook the snow from her
umbrella and closed the door.
"That was nice of him," I said leading her up the stairs. "What you
going to do? That snow does not look nice to drive in, so if you want
to skip dinner and get home I won't mind."
She gave me a grin and said, "I was temped to do just that when I saw
the forecast Abby, but since you had offered to make dinner, and now I
can see you have clearly dressed up for me I'd feel really guilty just
dropping your clothes in and running." She gave me a sheepish look as
we walked into the lounge. "So I packed an overnight bag in case it did
snow and you'd let me stay over."
"If you want," I said, "I've a bottle of wine in the fridge since
you're not driving, and you can sleep in my bed and I'll use my camping
mat and sleeping bag."
She gave me a naughty giggle. "How about we skip the camp bed and just
use yours I promise I'll be a good and not lead a young thing like you
astray."
I blushed and said, "What if I want to be led astray Cheryl?"
She snickered and said, "Do you now!"
"Trying to impress me Abby?" Cheryl said taking the laid table.
I blushed again and said, "Yes."
"I like that." She grinned, adding a cheeky tone. "Were you tempted to
wear your maids uniform?"
"Erm yes," I said.
"I half hoped you would, but looking at you now I don't mind that you
didn't, because you look very sexy in the LBD. Will you make me a
coffee while I change out of this?" She waved to her uniform.
"Sure, you know where everything is," I said. "How long will you be so
I can check dinner will be ready for about a quarter of an hour after
you're ready?"
"Twenty minutes or so I suppose."
I checked the pie and the braising potatoes and decided that they would
be ready on time, before setting a couple of wine glasses beside the
places on the table. I was still pottering about in the kitchen when
Cheryl returned carrying a bottle of wine and looking very different.
Her hair was pulled up into a high pony tail, and she was wearing a
black satin blouse, tight leather mini skirt, sheer black stockings and
high heel boots. Giving me a naughty smile her vividly made up eyes
were bright with humour. "What do you think Abigail goddess or gutter
snipe?"
"Goddess." I gasped with my eyes on stalks, adding without thinking, "I
really should have worn my uniform with you looking like that!"
"Perhaps you will darling," she said setting the wine bottle on the
table and strutting towards me. "But for now I think I like you as you
are. Now give me a kiss Abby."
I eagerly obliged, and felt my heart leap as she took me in her arms
and dominated me with her kiss.
Giggling as he broke her lips from mine. "You may fetch me a coffee
Abby." She turned and picked up her discarded bottle. "Oh and put this
in the fridge."
Perhaps because she now trusted me Cheryl was more tactile and
affectionate, and our conversation ranged all over as we ate dinner.
Politics, student life, gender, music and films all came up as we ate.
"You're quite the little domestic Abby," she commented with a smile as
I cleared the table. "My gender psychologist would love you! You
already have the kind of mind set she likes to see." She giggled.
"Someone who wants to make a smashing wife one day!"
"Is that an offer?" I laughed as I rinsed the plates and cutlery before
popping them in the dish washer.
"We'll see," Cheryl laughed.
"Coffee or more wine?" I asked.
"Oh wine, definitely more wine."
Giving me a faint smile, Cheryl said, "Can I ask you a question?"
"Of course?" I said opening the bottle of wine she had brought with
her.
"Do you fancy me?"
I blushed and said, "Cheryl! I've fancied you from the moment I set
eyes on you last month."
"I like you a lot Abby," she said her tone suddenly becoming more
serious. "But I'm not willing to be someone's secret girlfriend. I've
been down that road before. So I'll tell you now if we did start
something between us then it would have to be out and proud in public,
where everyone can see you're my girlfriend." She stressed the 'my
girlfriend' watching my reaction. Seeing I was about to say something,
she put her finger over my lips saying, "Not yet. I'm talking Abby."
I nodded.
"After being hurt far too many times I made myself a promise that I'd
only get involved in another relationship if it was with someone who
was willing to be seen everywhere as couple. Sexually I'm attracted to
people rather than genders, but my dream was always to find someone I
clicked with who was also openly trans." She gave me a naughty giggle
and added, "Which I'll insist you'll have to become if we get
together!"
I blushed and nodded.
"Now I know you have college commitments for the next few months that
mean you can't be the kind of openly trans girlfriend I want, and it
would not be fair on you anyway to insist on that yet. I know how hard
you have to work to let you risk your degree Abby, and I'm not going to
be a spanner that causes a problem." She gave my leg an affectionate
squeeze, and added before I could say anything. "And putting it bluntly
as Alex the bloke you're not at all what I'd look for as a boyfriend,
but as Abby the transgirl you're close to being my ideal girlfriend.
However you need to know before we go any further I'm a bit of a pain.
I have trust issues because of previous relationship and I like things
my way or no way. I'm also naturally bossy when it comes to being in a
relationship, and that has I know that bossy side of me has been
contributing factor in my unsuccessful relationships because I do like
to be the one in charge, dominant you might say."
"I sort of guessed that part Cheryl," I admitted with a smile. "And I
actually like it that you are the bossy type." She nodded as carried
on. "I'd love to go out with you as your girlfriend, and have a
relationship with you. Spending time with you over the last couple of
nights has been more satisfying that any I ever have had with someone I
have been attracted to. May be it's because I don't have to hide this
side of me with you." I waved at my dress. "Or perhaps it's because
you're also trans I feel more in common with you than anyone else. I
don't know why, but all I do know is I've not been able to get you out
of mind since I first saw you a couple of months ago."
Cheryl nodded saying, "I hoped you might say something like that. Now
am I right in thinking that you have a holiday at the end of term?"
I nodded. "We get four weeks at Easter, and all my course work,
projects and the like have to be in before we break to give us a chance
to recharge the batteries before its nose to the finals grindstone."
"So you can take a week or so off?"
I nodded. "I was planning to."
"Right then because I know for sure that you're a tranny I'm willing to
take a risk about keeping our relationship discrete, but not secret
mind, at least for now. I'll not be sneaking in and out from here and
your neighbours will notice that I'm staying over some nights." She
blushed slightly. "They always do, and that will make them nosey enough
to notice you leaving with me at times dressed as Abby, so they will
find out about you and us."
I blushed and nodded. "We don't really take that much notice of each
other. The only people I ever say hello to are Nick and his boyfriend
Terry in the flat bellow as their front door is next to mine, and they
won't care, as they are gay."
"Well expect them to ask questions when they see you with me, but if
they are gay they are unlikely to cause you any grief," Cheryl said.
"Now I not going to ask you to introduce me to your university set or
be part of your life there unless you graduate, and decide to stay for
masters. However I will be introducing you to all my friends as my
girlfriend and expect you to accept it."
"I can do that," I said eagerly, "but I'll need some help before I'd
feel comfortable going out?"
"Don't worry about that, I'd be with you and I'd make sure you look
right before I took you anywhere." Cheryl looked at me steadily over
her wine glass.
"I think I can do all that."
"Good, now how are you fixed for money?"
"Pretty good just now," I said. "I've not touched my military dependant
grant money yet, and still have about ?800 of this terms allowance
left."
"Okay so you can afford to come on holiday with me as my girlfriend
over Easter?"
"Easily."
"Good, I'll put a deposit down at the travel agents next time I'm in
town."
"Okay, if you tell how much you need off me I'll get it from the ATM in
the morning."
"Good." She nodded.
Cheryl sat back sipping her wine studying me carefully before saying,
"But if we're keeping discreet round here I think I'll ask you to
accept a couple of conditions?"
"What are they?" I asked blushing.
"They are not hard or intended to make a fool out of you, they are just
to insure that my girlfriend remains mine until I decide I want to take
us a stage further, or if we separate you have as much to lose as I
do."
I nodded. "I'll do anything you want Cheryl!"
"Anything?"
I nodded.
"I'll ask you to prove that in a little while. Now don't worry about my
conditions I'll explain them later, let just see how tonight unfurls
Abigail." She smiled, before asking, "But for now pass me my handbag,
and go stand by the kitchen counter."
I did as she asked, and blushed when she produced a small 35mm pocket
camera. "Photo time Abby. I'll print them over the weekend and give you
copies."
I willingly posed how she wanted. It was a laugh as she got very David
Bailey on me directing me this way and that as she teased me about
being a photo whore as she encouraged me to show my stocking tops,
suspender straps and flash my panties for her. Finally satisfied she
dropped the camera letting it hang round her neck and said, "You said a
little while back that you'd do anything to prove that you'll be what I
want in my girlfriend?"
"Yeah," I nodded.
"Then prove it!" she said with a grin. "Come, kneel down in front of me
Abby?"
I blushed but did as she asked feeling more than a little submissive as
I slipped to my knees before
her. Looking down at me Cheryl gave me a delighted and very naughty
grin as she reached behind her and released the catch and zip of her
leather skirt. With her eyes dominating mine she said. "Remove my skirt
Abby."
My eyes were wide as I obeyed her command and slid the soft tight
leather down her legs revealing her flat fronted panties, framed by a
matching red and black suspender belt, and her stocking tops. In a
hoarse whisper she said. "Now lean forwards and kiss my panties, then
look up at me and ask for permission to pleasure me Abigail."
I felt my blush burn over my face as I lent forwards and kissed her
panties before I leant back on my heels and looked up at her saying,
"May your girlfriend pleasure you Miss Cheryl."
"Oww Miss Cheryl I like that Abigail." She laughed, and then said, "Yes
sweetheart, you may remove my panties now Abby."
My hands were shaking as I eased her panties down and saw her rather
large penis suddenly pop out from between her legs. From above my head
I heard her purr. "Good girl, now get to know your girlfriend Abby, and
make her feel so good."
I hesitantly leant forwards again and kissed her now rapidly swelling
cock and then gave the head a tentative lick.
Above me I heard her camera click, which made me pause until she firmly
said. "Keep going girlfriend, I'm just keeping my word about being able
to hurt you as much as me Abigail."
Following her instructions I licked and then sucked on her cock,
looking up into the lens of her camera when she asked.
As I brought her cock fully hard she continued snapping away until all
of a sudden she grabbed my hair and gasped. "You're quite the
cocksucker Abs... Oh fuck are you!" As she gasped. "Yes!"
Holding my head she started to fuck my mouth and I enjoyed letting her.
Her cock was filling my senses and then all of a sudden she stiffened
and I felt her cock jump on my tongue. Letting out a squeal of pleasure
she exploded into my mouth gasping after the first surge, "Swallow it
Abby, swallow it all!"
As I tried to swallow everything she produced, I could hear her making
little sounds of pleasure as I suck and swallowed. Eventually her cock
stopped spurting and she gasped. "I can tell you've done that before
Abigail!" For perhaps 2 minutes she held me there before pulling my
head up so she could look in my eyes as she demanded, "Now clean me up,
and replace my panties and skirt like a good girl... And then you can
thank me for letting you be my girlfriend!"
Once again her camera was clicking and I did not have to be told to
look at the lens as I licked her clean and slid her panties and skirt
back into place before I blushed and said, "Thank you for making me
your girlfriend Cheryl."
Cheryl giggled delightedly and then pulled me to my feet saying, "I
think Miss Cheryl is more appropriate when your on your knees Abby," as
she ravished my lips. With out breaking the kiss she sat down pulling
me firmly on to her lap saying, "I think after that, from now on you
can consider yourself my girlfriend Abigail!"
I felt embarrassed and a little humiliated by what I had done but also
incredibly content, and Cheryl was clearly delighted as she laughed.
"Thank you Abby! You passed my willing to sexually do as she's told
test with flying colours." She gave me another kiss saying, "And it was
clear that you liked giving me a blow job because I could see your
little girl cock was hard as a rock under your dress!" She squeezed my
still stiff cock though my dress her adding, "And I'll see about
repaying the complement later sweetie, don't you worry your sweet head
about that."
I felt giddy with delight at her pleasure from what I had done, and
said with out thinking, "I love you!"
Blushing from my outburst Cheryl kissed my nose and said, "I know that
now pretty," and gave my bum a goose with her finger, "I know your not
an oral virgin but what about here?"
I blushed and said, "Once before at school Cheryl."
"It will be more than that by tomorrow morning babe because I'm going
to fuck your brains out later!"
She did as well!
We were both somewhat cum stained when we fell into bed, and I pretty
much went out like a light until I awoke just after seven next morning
aware of her spooned tightly against me. Not wanting to move but
needing the loo I lingered as long as I could before I extracted myself
from her arms and padded to the loo aware of a not unpleasant burning
in my tail.
Startled by my reflection I saw my make up smeared face and blushed
feeling more than a little ashamed of being such a slut the night
before. Even though I was feeling ashamed of myself I was also filled
with a sense of peace and satisfaction from how much pleasure I had
given Cheryl. My mental perambulations were cut short when Cheryl
sleepily called, "Since you're up Abby make the coffee."
"Here's my girl!" she exclaimed as I came in carrying the coffees in my
nightie. Patting the bed beside her, she said, "Hop in honey bunch."
I saw Cheryl in the raw that morning stripped of all the enhancements
that made her look more feminine and still thought she was beautiful
and I told her so. She was blushing like mad when her that as I slipped
back into bed with her. I'll admit I was a little unsure about what I
had got into, but I was also just as delighted that I had.
"What do you have planned for today Abby?" Cheryl asked once I was back
in bed.
"Nothing, just doing the research for the paper I was set on Thursday,"
I said after a sip of coffee.
Cheryl nodded and said, "I was planning on going home and then into
town, but now I want to take you with me, however if you have
coursework, that plan is scuppered as I don't want to have to come back
here before work on Monday."
"I could ride down," I offered.
"It's still snowing, I looked," Cheryl said pulling her face. "And
anyway riding a motorbike is not the sort of girlie girl behaviour I
want to see from my pretty tranny lipstick lesbian girlfriend," She
giggled. "If she's riding a bike it will be behind me as my biker
chick!"
"Oh!" I giggled. "I'd enjoy that."
Cheryl grinned and the added, "Also I wanted to take you to my place
just in case I need to use any of the specialist cosmetics and
feminising garments I have to convincingly fix you up. However now that
I think about it I'm not sure I have anything size wise will fit
correctly, so we'll have to pop in to a shop I know that supplies
certain useful items for girls like us, before we hit gay friendly bar
some lunch."
The idea terrified me but I said, "I can always bring my paperwork to
your place Cheryl and go to town with you today and do all my research
reading tomorrow, so long as you don't mind me being antisocial with my
nose in my books?"
"Bugger it. We'll go to my place and I'll bring you back first thing in
the morning," Cheryl decided, "because if you're with me tomorrow I'll
be tempted to distract you."
"Go and hit the shower Abby, and then dress in your student uniform
look," Cheryl decided. "Don't worry about your hair or make up I'll do
that for you because you're coming to my place."
She clearly read the fear in my eyes and said kindly, "I know it's
scary but once you've got it over first time, it gets much easier and
you said you'd be my girlfriend. I want you to prove that you meant it
by insisting that you come with me today as Abby!"
By the time Cheryl had finished with my hair and make up it was a far
more tarty looking version of Abby looking back at me from the mirror.
Because of the snow outside Cheryl let me wear my welly's and my
outdoor waterproof jacket but I had my pair of heels the over night bag
she made sure contained no male clothing. I had thought it was quite
late but much to my surprise we were ready to leave by 9.30.
"Looks like the first thing on your list for today is a handbag,"
Cheryl commented as I put my wallet, keys and lose cash in my overnight
bag. "I'll lend you one to take to town and after you've been to
Silvia's, buying a bag, and may be an outfit for tonight will be a good
objective for a first shopping trip. Oh and throw your passport in
because while your being sorted at Silvia's I'll pop to the travel
agents and book the holiday."
"Who's Silvia?" I asked, but Cheryl did not hear me as she picked up
her bags and said, "Let's go, I'd like to get out of the town before
the football fans start congesting the roads."
I was shaking with fear as I opened the door and hesitated enough that
Cheryl physically pushed me out into the snow covered car park.
Thankfully my downstairs neighbours curtains were still pulled closed,
but I was still on tender hooks as we cleared the snow from Cheryl's
car and pulled away from my flat.
"Relax Abby!" Cheryl laughed. "You've done the hard part, you're
outside in daylight enjoy it."
Although my car park was covered by a couple of inches of snow, the
roads had been cleared so traffic was flowing freely. It took us about
forty minutes to reach Cheryl's house in a nice part of a the nearby
regional centre. We did not stay though because after a quick winnow
through her wardrobe for a change of clothing for her and switching my
welly boots for my heels, she led me straight back out.
"How much money have you got on you just now?" Cheryl asked as we got
back into her car. "About twenty pounds in cash, but like I said last
night I've got a good bank balance and can get more from an ATM or use
my credit card."
"Good because you really need a couple of things from Silvia's. Better
boobs than the stuffed socks you are using, a gaff to hold you flat and
some figure shaping," Cheryl said. "If your boobs move in a more
feminine jiggle and you pull in a bit of a waist line you'll look
instantly better, and that will make you more confident. Also she knows
all kinds of little tricks you can do to help improve your feminine
posture."
"How much do you think?" I asked pointing to a Barclays up ahead.
"Because I can get some out of that cash point."
"Two hundred tops I expect. Can you afford that?" Cheryl said.
I nodded. "Yeah, I'm more than solvent." I give her a cheeky smile
adding, "If my current account gets a little thin I can always use the
savings account where I have the first real instalment of what my mum
and dad left me but if its going to be a couple of hundred I'll use my
credit card," I said. "Assuming she takes them?"
"She does."
"What about the holiday deposit?"
"Dunno, in the travel agents magazine it said it was 225 each so ?450
for us both with flights but no transfer. I've found its worth paying
the extra cost of grabbing a taxi from the airport, rather than hanging
around for ages waiting until the transfer bus is full. I'll pay that
and then you can square up with me later."
"That's fine." I nodded. "Where are we going?"
"The Canary Islands," Cheryl said pulling up by the bank. "I know a
great a resort that is gay, lesbian and transsexual friendly where we
can spend ten days and find out we really are compatible." She gave me
a smile and said, "Off you go."
"You're not coming with me?" I said shocked.
"Nope, I want you to do this on your own Abby. Its only ten steps to
the machine, and ten back."
If I thought I was scared when I left my flat this was ten times worse
even thought. Yet when I considered it at the cash machine I actually
had less to lose, no one knew who I was or where I was from. Even so
those ten steps to the machine and back were ten of the longest of my
life and if I had not been so wound up, I might have noticed that no
one was batting an eyelid to my presence as I walked back to her car.
Cheryl gave me a kiss when I got back saying, "Well done Abby!"
"Here." I handed her a stack of ten pound notes. "There's ?230 there."
"You didn't have to pay it all at once," Cheryl said stunned.
"I can afford it so better paid," I said. "I've still got 70 until I
hit my monthly limit and its the 27th now, so thought I might as well
as just pay you all of it."
After walking to the cash point and back, and having Cheryl reinforce
my confidence by telling me that no one knew who I was, the walk from
when she parked the car to 'Silvia's Ladies Wear' was not as
frightening as I expected. I'd occasionally feel eyes and hostile looks
aimed at us but as Cheryl did not respond I avoided eye contact and
kept walking. The shop was in a side street off the town centre and
seemed to have come from a different era, with its vintage signage and
window displays.
Silvia was not what I expected. I did not know what I expected but it
was the stylishly dressed thirty something woman who said from behind
the counter, "Morning Cheryl, who's your pretty friend?"
"This," Cheryl said putting her arm around my waist. "Is my new
girlfriend Abby and she needs a few enhancements in shape and a little
help with her posture."
"Nice to meet you Abby. I'm Cathy and my grandmother Silvia started the
shop in the 50's, so what sort of boobs are you interested in?"
"I'd say a C cup," Cheryl said. "What do you think love?"
"Erm yes I guess," I said feeling a little bemused as I took in the
contents of the shop.
"Not stopping?" Cathy asked as Cheryl turned to the door.
"I'll be back in a half hour I need to pop to the travel agents and
book us a holiday."
"Okay if I still have Abby in the fitting rooms ring the bell outside
when you get back and I'll let you in."
"Right then let me have a good look at you," Cathy said walking round
me before commenting, "You could go larger but I think Cheryl is right,
a C cup will look good on you Abby."
"Okay," I said.
"Great," she said with a smile and showed me a selection of false
breasts, explaining the pros and cons of each.
"Obviously you get what you pay for but in my opinion these silicone
breasts are my most popular breast in terms of what you get for the
price." She handed me a wobbly false boob. "They move, feel and look
under a bra very natural. Also they can be adhered to the skin so there
is no risk of slippage and because they were developed for use by
mastectomy patients they are VAT exempt, and being made from a medical
grade silicone they are hypoallergenic, which for ?85 is a lot of
breast. I'd also advise you to get the adhesive, skin prep and cleaning
kit which is another ?20, but lasts for ages, and means you can wear
them with a normal bra or a full cut swimming cossi."
By the time Cheryl got back I was wearing the breasts, and had been
strapped into a body shaper than gave me both a waist and made me stand
up correctly. The final items were gaffs which were basically just a
tight pair of panties that held my cock down.
"Wow, you look great!" Cheryl said when Cathy let her back in. "Did you
get the adhesive kit for the breasts?"
"Yes, she did," Cathy said with a please smile. "And I think that is a
result."
I left the shop ?250 lighter but my reflection in the shop window was
worth every penny as Cheryl took me shopping for a handbag, a couple of
pairs of shoes and new outfit, which added another 200 on my credit
card.
Although it was scary at first after about an hour I started to relax
and enjoy the sensation of being out. I sure we were 'read' often but I
took courage from Cheryl's example and tried to ignore the occasional
looks we attracted. It was pretty clear as she took round the shops
that Cheryl meant what she said about our relationship being open and
in public because she insisted on public affection.
After meeting some of her friends in the gay pub where we had lunch,
Cheryl drove me back to her place, and spent a happy afternoon teaching
me some make up tricks and giving me pointers on my appearance. This
eventually led to a long and at times emotional discussion about why I
cross dressed, and whether I was considering going on the program after
I graduated. Pulling no punches about the risks of following her
example Cheryl made no secret of the cost both in terms of losing
friends and family, and job opportunities, before she mentioned the
financial costs. It was a lot to think about, but I did admit to having
considered it myself, and that I had not long before I first saw her
actually spoken to a doctor about it.
"She said I should go and see a specialist counsellor but advised me to
wait until the final year stress was off in case my issues were down to
being under a lot of pressure and living alone."
"They told me the same Abby," Cheryl said. "But if you are genuinely
transgendered, you'll already know that stress has nothing to do with
it, and from all you have said to me, I think you should see one and
soon, because so much of what I've just listened to sounds just the
same as what I said when I was dithering about making that first
appointment," She gave me a kiss and added, "I can try to get you in
with mine if you want?"
"Erm, alright," I said, blushing like a traffic light.
Cheryl also had a very clear vision of the sort of girlfriend she
wanted me to be, and at times seemed to be micromanaging how I was
dressed, did my hair or makeup to the point that I even teased her
about how she was making me into little more than her talking Barbie
doll. There was very little self-determination in how I looked at first
as she dictated what I wore, how I did my make up and how I should
behave, and yet I loved it. I was strange how I never once felt I was
losing my independence as I acquiesced to her directions, and the more
acquiesced the more she loved expanding her control over my appearance.
With in a fortnight of us starting going out together Cheryl made me my
first appointment to see her gender identity counsellor and made sure I
kept it. Although I was rather nervous about it, I actually felt
relieved when I came out of psychologists. He was very easy to talk to,
and said just as my hour came to an end, that he did not see any issues
with me starting the first stage of treatment as I was clearly
comfortable in role. Two session and a medical later he wrote me
prescription for a testosterone blocker and a female hormone the week
term ended and officially started my transition.
After she took me shopping that first time as Abigail, Cheryl quickly
ramped up the activities. First I met all her friends and they were
left in no doubt who wore 'the trousers' or that I would be joining
Cheryl on an RLT as soon as I finished college. At first we would just
walk around the city centre window shopping, or looking in known
friendly stores to get me used to being in public dressed in feminine
outfits, but before long we were actually shopping in normal shops. Our
first 'normal shops' shopping trip was for our holiday. As usual Cheryl
decided what sort of bikini's, swimwear and holiday outfits I should
buy, even going as far as selecting my accessories like earring and
jewellery. She taught me how to 'tuck' myself so I presented a flat
groin and made me keep it like that, which was at first little
uncomfortable but also quite thrilling!
It did not take long for Cheryl and I to work out a routine, a couple
of times a week she would stay over at my place and on her weekends off
we went to her place. Being in a relationship with her did not actually
disrupt my life to any great degree, with the pressures of course work
I had already curtailed most of my out of college student socialising,
and rarely had to worry about due date papers interfering with our
rapidly blooming relationship. Although I kept my dressing away from
college I did spend quite a lot of time in town dressed with Cheryl
especially after we started going to the towns gay pub.
As Cheryl predicted my neighbours had seen us and were curious, but did
not really ask until we bumped into them one night in the gay pub.
"Hey!" Nick said seeing us when he walked in with Terry. "I thought
that was you Al?"
"Hiya Nick," I answered as they walked up clearly alight with
curiosity. "Meet my girlfriend Cheryl, and I go by Abby when I'm
dressed like this."
"Hello Cheryl," Nick said to Cheryl. "I'm Nick and this is my better
half Terry, can we get you ladies a refill?"
"Sure," I said as Cheryl studied them before saying.
"Hello, and thank you, we'll have a couple of white wines please."
After about ten minutes of small talk I said, "Well I guess I better
mention the elephant in the dress, since you two are far to polite to
ask. Yes I'm trans, and yes I'm in transition and I'll be starting my
RLT at the end of June."
"That obvious huh?" Terry laughed.
"With all the curtain twitching you've been doing since I started
seeing Abby its kind of hard not to notice your curiosity," Cheryl said
cheerfully.
"So how did you meet?"
We ended up becoming good friends with Nick and Terry, who had many
contacts with in the universities GLTB group. Through them I met people
at college, which inadvertently forced me out to my tutor a little
earlier than I expected after he turned out to be the university
advisor to the group and was attending a meeting just before the end of
term to explain the new procedure for any claims of discrimination and
recognised me after I submitted a question about the colleges views on
toilet use by transitioning transgender females. It actually turned out
to be a good thing as my tutor straight up told me when I handed my
dissertation in the following week that being on an RLT would not have
any bearing on my conditional offer of a masters if I got my expected
results.
"I'm not planning to start my RLT until the end of next term, so it
won't be an issue for a while yet," I told him as my academic tutorial
turned into a very reassuring meeting as it was nice to know that
transitioning was not going to mess up my plans to carry on in
education.
"Well just let me know next term if you are going to come back as Abby
in September and I'll see about amending your college records, and can
even arrange for your degree certificate to be issued so you graduate
in your new name assuming you have changed it by deed poll before they
are printed."
"I'll think about Doc and get back to you," I said, before giggling
when I added, "That would set the cat amongst the pigeons with one or
two of my god bothering course mates."
"Ignore them Alex, if that's how you want it the college will back you
all the way, and after the spat at Manchester the other year, if they
have any sense they'll keep their views to themselves because, the
majority of students will not give a damn twenty-four hours later." He
chuckled. "You're not the first transgender student here and wont be
that last. Now enjoy the break and make sure you do some work."
"Will do Doc and thank you for the advice," I said as I left feeling
rather excited about the idea of graduating as Abby rather than Alex.
As we were due to fly out to Gran Canaria the following Monday morning,
right after my tutorial finished, Cheryl took me to her hairdressers to
get my hair done. Tied back with a little hair gel my new hairstyle did
not look that different to how it had looked before but when lose it
was clearly now cut in a feminine style. Cheryl however was not
satisfied with just a cut and style as she also got the hair dresser
add honey blonde streaks into my muddy blond natural colour.
Although I was travelling as Alex, everything I was actually wearing
was female fit. My jeans were bootleg cut hipsters. My top came from
Top Shop, and even my trainers were ladies Reebok's. Underneath my
clothes I was wearing a 'training bra' and matching panties, and I was
completely hairless bellow my eyelashes except for a little neatly
trimmed triangle above my tucked penis.
The flight took just over four hours and with in an hour of landing we
were at our apartment in a hotel overlooking of all things a shopping
centre, which I quickly found out was the hub of the gay friendly scene
here.
"Right Abby," Cheryl said, "you go and unpack, and then get change in
to your bikini, while I'm popping to the shop for milk and wine. Oh and
before I do, give me your left hand," Producing a matching ring to the
one she wore, Cheryl pushed it on to my ring finger and said. "Now
you're ready to become my girlfriend for real!"
She was back before I had unpacked, and before long we were both taking
in the afternoon sun on our balcony.
"I'd go down to the pool but the sun's off it now Abby," Cheryl said.
"So we'll make the most of it here before it goes down and then hit the
bars for evening."
When Cheryl said openly, she meant it because she had her arm round me
everywhere we went, as we bar hopped. The place was very gay but there
were quite a few girls like us around and Cheryl knew all the bars and
clubs where we were welcome. She seemed to know lots of people and
introduced me everywhere as, "Abigail, or Abby my girlfriend."
It was heavenly.
Trish 2018.