Preface: This story is told in a series of first person accounts by the parties
involved. The story is, of course fiction, but is inspired by a number of
personal experiences. Hope you enjoy it. The author welcomes criticism of
any kind.
Where Angels Fear to Tread - Part I
By A. K. Remenko
Chapter One - Pam
In retrospect I'm glad things turned out the way they did; I never had it so
good! At the time however, it was frankly upsetting and I came very close
to walking away from the whole thing any number of times. I was
married once before, a real macho jerk that loved himself a lot more than
he ever cared for me. He's been married and divorced twice since so I
guess my judgement was vindicated. At any rate, I'd only been married to
Phil (seems funny to use that name now) for a little over 2 years and it was
crushing to think I'd was involved in a second failed marriage.
That's exactly what I thought I'd been confronted with. My ex, Jake, had
been a philanderer of major proportions so I thought I recognized the
signs. They were the usual things like a tube of lipstick under the seat of
Phil's car and some weakly explained absences. I figured I wasn't going
to put up with this again so I decided to do a little snooping. I really hated
myself for it but I wasn't about to put up with that again. Jake used to
hide little "souvenirs" of his adventures; not too bright but all men are
fools. I figured Phil would do the same. What I found absolutely floored
me. When I found the lingerie I thought it was "the usual", but then I
found the videotapes and the magazines. (Jake and Phil had one thing in
common, they both thought the garage was a safe place.)
I had no idea what to do, or even think. The only person I felt I could talk
to was Cheryl.
Chapter Two - Cheryl
When Pam called me and wanted to meet for lunch I thought nothing of it;
we'd do it often enough. We met at work, though I've changed jobs since,
and became good friends quickly. We never did the "couples thing"
much, as the guys had always seemed like excess baggage when we did
try it. Pam tells me I was really there for her during her divorce from
Jake, but she would have done the same for me. Happily enough, I don't
have THAT problem with mine. Jake was a charmer though.
I could tell Pam was upset the moment I laid eyes on her. It was a
Saturday so we had a glass of wine before lunch and Pam lit up a cigarette.
I hadn't seen her smoke since her divorce so this had to be something big.
I could see she couldn't bring herself to start so after the usual chitchat I
tried to get her to talk.
"Smoking again?" I asked. Pam had already finished her first glass of
wine and was casting her eyes about in search of our waiter. "Haven't seen
that since you-know-who." I added and saw it hit a nerve with that one.
"No, it's not like that at all" Pam replied, "it's just... just...oh...damn."
"Out with it honey. You obviously didn't call me to drink wine and
smoke." I said and leaned forward.
"Well" she stammered, "it's Phil, I think...well, I found...he's a
transvestite or at least interested in it."
I sat back and smiled, then chuckled a bit and finally just laughed. Pam
was furious with me.
"Cheryl, this is NOT funny. I thought, of all people, I could depend on you
to help me through this and you're treating it like a joke and believe me,
it's not."
I quieted down and leaned forward again and said in a conspiratorial tone,
"I'm not laughing at you, I'm laughing with you. George is a crossdresser
so I know exactly how you feel...at least I think I do."
By the look on her face it was obvious I could have knocked her over with
a feather.
"George?" she croaked, "why didn't you ever say anything?"
"Listen dear" I said, "I had no reason to and frankly it was really not your
concern. I dealt with it and continue to."
She was amazed. "But why?" she queried.
"That's easy" I sighed while motioning to the waiter for another round and
a clean ash tray," there's no reason not to." I added somewhat slyly "And,
there ARE...uh...compensations."
I continued, "George is a decent guy, a hard worker and a can be lot of
fun. I'm comfortable with him. He's not much in bed, but how many are?
My guess is Phil is pretty much the same. Do you really want to get
divorced again and start all over? I sure didn't. What guarantee would
you have that the next one would be any better or, God forbid, worse?
You're pushing 30 dear and still in good shape, but have you checked out
the competition?" I nodded toward a couple of early-twenty-something
girls seated to our left who were very pretty.
That gave her pause. "But..." she hesitated, "well... I mean... maybe
they're gay then?" This was clearly of concern to her so I launched into
my standard spiel.
"Look, NOBODY is 100% heterosexual, or homosexual for that matter.
Think of it as a continuum and a sort of sliding scale for TGurls. Some
TGurls are more attracted to guys when in gurl mode, but that doesn't
make them gay. George has no interest in guys when he's 'George'." I
hooked my fingers to indicate quotation marks. Frankly now, how is your
sex life? Sounds weird I know but this might provide a boost."
Pam took on a somewhat wistful expression. "Well...... ." she managed at
last, "a little on the staid side I guess." She cast her eyes down a bit, "Phil
is sort of... well... small there".
I thought "not like Jake" but didn't dare say it. Pam wasn't exactly
inexperienced when she met Jake but had mentioned more than once,
usually after a few drinks, that Jake was generously endowed. That, and
his apparent skill, may have been why she put up with him for as long as
she did.
"Yeah" I responded, " the person that said 'it's not size, it's what you do
with it' was definitely of the male persuasion; you'll be pleasantly
surprised at what can happen there."
"Look" I continued, "play it smart; think it over and don't do or say
anything 'til you have. Reserve the greater option. OK?"
She thought about that.
"What was your first clue?" I asked.
"Found a tube of lipstick in the car" she replied.
I told her to put it back where she found it and to say nothing: the poor
Tgurl was probably going crazy trying to figure out where she left it.
We ordered lunch and ate quietly; Pam was very pensive but gave me a
big hug when she left.
Chapter Three - Pam
I was in a bit of a funk for a while after my lunch with Cheryl. I vacillated
between feelings of acceptance, anger, insecurity and panoply of other
emotions. After a time I settled on being upset that Phil would deceive me
like this. I admit it wasn't as bad as what Jake did, but it was still lying
and sneaking and very aggravating. Phil had put me through an emotional
wringer and I'd done nothing to deserve it.
I had taken Cheryl's advice though, and good advice it was. After a bit, I
cooled down and thought it would make sense to talk to her again,
especially since she had experience with this. I called her for lunch during
the week but she was busy so we decided to meet for drinks after work
instead.
We decided on Cooper's which was an after work/dinner crowd, busy but
not too busy. A good chat atmosphere and handy to home and work. I
arrived before Cheryl and had to put up with the suit-and-tie married
Romeo's for a time, but nothing I hadn't handled before; they are so lame.
We grabbed a table, Cheryl ordered a drink and looked at me and said
"And?"
She made me smile. "And" I emphasized, "I followed your advice, I have
given it some thought and decided I needed to learn more. Who better
than you to learn from?"
She chuckled, "One of the reasons I like you so much is that you're so
smart. How can I help?"
"Well", I replied, "we both know knowledge is power. I have this
knowledge and power and don't know what to do with it. There are many
things I could do but I don't know which is right, or even best. I'm an
educated woman but I am at a loss here. You've been there before and
must have considered the options and are clearly at ease with this" and
added with a smile "you bitch."
Cheryl chuckled and asked "Where are you with this?"
I replied telling her about my emotional roller coaster and all the feelings
I'd experienced but she cut through that quickly.
She looked at me and asked, "If you had to come up with one feeling, the
most prevalent one, what would it be?"
I stated reflectively, "Given that, I guess I would say, pardon the
expression, pissed off. Pissed off about the lying, deceit and the rest of it.
I can't believe Phil did this...treated me this way...especially since he
knew what Jake did and how I felt about that."
Cheryl slowly closed her eyes, rolled her head slightly and hissed,
"ehhhhhxcellent." She added "I'm not the only bitch you know... there's
another...her name is Paybacks." I sensed I was about to meet a Cheryl I
never knew existed before.
Chapter Four - Cheryl
After I left Pam at Cooper's I headed home with my mind whirring away.
I hadn't been this excited since I'd launched my little campaign with Lexi.
Lexi is my husband George but I just don't think of her as George
anymore. She's been Lexi for so long I've grown accustomed to it. I've
felt so alone in this it was a treat to find my best friend was now involved
in it as well. I needed Lexi's help but didn't dare tell her. She spends
hours on the phone with her TGurl friends tittering away about anything
and everything. Frankly the high-pitched giggling is a bit much at times.
Lexi is a gossip and would gleefully spread the word about what was
going on. Everyone seems to be web literate these days and the TGurls
have a real network. I couldn't take the chance that Phil was out there
under a pseudonym and capable of being tipped off.
When I got home my sissy was not only online but on the speaker phone
as well. She was in a bra, blouse, slacks and a pair of flats and looked
sweet. Her makeup was flawless and I envied her that; she is, I believe,
better at it than I am. I could tell dinner was ready by the wonderful smell
coming from the kitchen. I stuck my head in the office door and said "Lexi
dear, have dinner with me tonight." This was a treat for her and she was
quick to log off and end the phone conversation. (Brenda I think; I
recognized the voice having called Brenda's wife a number of times.)
Dinner was, as usual, superb, pasta with shellfish, salad and rolls and a
very nice Chardonnay. The little slut can cook. She was hot to find out
the cause of the occasion but I waited until dinner was done and we went
to the family room to finish the wine.
We sat and I began, "Sweetie, I need a favor. Check the web and get
male/female clothing size conversions for me would you please?" "Oh,
and the most complete list of TGurl and transgender website URL's you
can put together easily."
Her eyes positively shone and she asked me what they were for. I just
looked at her. Quickly she lowered her gaze and mumbled an apology.
She periodically tests me by trying either to resurrect her lost manhood or
strive for some form of equality; both are futile efforts. I honestly think
she doesn't want either but my consistent discipline serves to remind her
how much I do care for her.
She asked when I needed the information and I replied that Thursday
would be soon enough. I told her I was tired, a long day and the drinks
with Pam I guess, so I would pass on my bath and would shower in the
morning instead. I gave her a goodnight kiss on the cheek and headed for
bed. As I passed her room on the way to mine I noted how neat it was. I
marveled at the fact that she worked a full day and still kept the house
spotless. I made a mental note that she deserved a little surprise gift again.
Chapter Five - Lexi
Cheryl was certainly pumped up about something: dinner with her and I
get to do her a favor to boot. (Love those, it means I have a treat coming!)
I tried to find out what was up but no luck. The pasta recipe I got from
Anita at work was a killer. The size thing is no problem to locate but it
reminded how I only think in women's sizes now. A few months ago I
needed new men's shoes, a funeral to attend, when the clerk asked me my
size I told him ten only to find them to large. It finally dawned on me that
I wear a ten in heels. Blonde day I guess.
Chapter Six - Pam
Cheryl called me the morning after our get together at Cooper's and asked
me if I had Saturday afternoon free for a little shopping. Phil was
spending the morning and afternoon golfing and his golf buddies were
coming back to our place for their monthly poker game afterward. Phil is
a junior partner of a manufacturers rep firm so golf is sort of stock-in-trade
for him. I could therefore look forward to a free afternoon and evening, in
addition to the house smelling of cigars for a week.
Cheryl also asked me to get all of Phil's clothing sizes and whatever
measurements I could muster together and email them to her at work. Phil
was not big but in decent enough shape, not flabby but not muscular
either. Phil was sort of rounded rather than angular. Jake was a real
beefcake and I'd been subconsciously been turned off to that I suppose. I
read the obvious inference from Cheryl's request but was more intrigued
by what was to follow our shopping spree for Phil.
I'd always done most of Phil's shopping (he hated it) and was therefore
familiar with most of his sizes but the measurements were another matter.
I didn't have much there and would have to make some educated
estimates. Cheryl and I agreed to meet for a late brunch and a little
planning before embarking on the day's work. I confess that our little
conspiracy had captured my imagination and looked forward to Saturday
with some anticipation.
The balance of the week passed uneventfully with one exception. Phil
made a big effort to clean and wash our cars, something he almost never
did. A car wash was so much easier and faster. I noted a little sense of
urgency in this and was very glad I'd taken Cheryl's advice and returned
the lipstick to Phil's car. I put it on the floor beneath the driver's seat
between the side of the seat and the console. I made it hard to find so the
little sneak would have to work a bit. He did my car first, and fairly
quickly too. His car took somewhat longer because he really went after the
interior. Surprise surprise...
When he was done he was in much better spirits and clearly pleased with
himself. I made an excuse to take his car for a run to the convenience
store. A fast check of the floor revealed the lipstick was gone so Phil had
not a care in the world, that he knew of.
Chapter Seven - Phil
I found the goddamn lipstick. It was under the seat of the car of all places.
I'd been sweating bullets ever since I noticed it missing. It was a close
call perhaps. I'll have to be more careful in the future. Just for peace of
mind I checked the garage and everything was cool there. Life is good.
Chapter Eight - Cheryl
Pam emailed me the size list and I gave it to Lexi so she could get busy.
Emailed the URL list Lexi prepared to Pam and suggested she put in a
little study time. Pam and I agreed to meet at the food court at the mall
Saturday at 11 in the morning for a quick bite and to rough out a shopping
list. I told Lexi we were going to do a little off the cuff fashion show and
photo session because I wanted new pictures of her. I told her to get
several outfits ready and not too be too shy either. Her taste is a bit on the
trashy side for me, but that comes with the lifestyle I guess.
We took the pics and the little ham loved every minute of it. My guess is
they were scanned and all over the country hours after she picked up the
prints (made a note to get an e-cam... before e-cams came along I'll bet
TGurls added significantly to film manufacturers profits.)
All this preparation brought back memories of the early phases with Lexi,
sort of nostalgic in a way. Lexi was obviously beside herself with
curiosity about all this but didn't ask because by now anticipation was
much of the thrill. She knew I'd let her in on it in good time, very well
trained if I do say so myself.
Saturday morning seemed to take forever to arrive but arrive it did. I
packed up everything in a shoulder bag and headed for the mall. Lexi was
headed for her Saturday night foray to the Tclubs and would spend hours
and hours getting ready and by this time required absolutely no help from
me.
Pam had a table in the food court and gave me a "Hi" and a smile as I slid
into my chair.
"Get any web surfing done hon?" I queried.
"Oh my God I never KNEW." she gushed, "I had no idea it was like this. I
had assumed there were a few certainly but this... "
"Millions upon millions" I finished for her, a bad habit of mine. I
acquired this habit because I know what Lexi is even going to think, much
less say, before she thinks it. "Feeling a little less solitary are we?" I
added.
I pulled the paperwork I'd prepared from my bag and handed Pam a copy
of the shopping list I'd prepared. "This isn't complete of course" I told
her, "but it will do for a start. We've got a lot to do but all day to do it in.
Do you have Phil set up for his poker game tonight?"
"Yes" Pam replied, "plenty of beer, munchies, a party tray, coffee and"
she paused with a smile, " I did a little baking too."
"Ah" I grinned, "like a lamb to the slaughter". I reached into my bag and
took out the packet of photos I'd taken of Lexi and handed them to Pam
with a "Here, take a look at these."
She shuffled through them at a reasonable pace and commented that they
were similar to the ones she'd seen on the websites she'd visited. She then
began slowing down and peering at each picture a little more intently. I
didn't say a word I just sat back and watched her face. Before long her
jaw dropped.
"Oh gawwwwd" she stammered, "its...its George!"
"Not bad, huh?" I countered "A little on the slutty side, but that's her
style."
Pam had stopped on a facial close-up and was carefully examining it
"George's..."she started "Lexi" I corrected, "Yes" she continued his...",
"Her" I corrected again "Yes her..." she forged on, "...her eye makeup is
wonderful."
"Lexi is incredible with eyeliner" I told her, "best I have ever seen
anywhere. She uses liquid liner; it gives her the sort of hard look she
loves. I could never use the stuff myself."
Pam looked up at me clearly impressed. I leaned forward a bit and said to
her, "I've got a proposition for you. I'll bet you a dollar you can't do
better with Phil."
She blinked. And then a smile began at the corners of her mouth and
slowly spread to become the biggest ear-to-ear grin I've ever seen on her.
"You're on" she stated confidently, "I'll even spot you the head start.
However, I have a condition: we don't tell either of our gurls about this.
Also, for the time being, we keep them in the dark about each other."
I immediately agreed: we laughed, grabbed our bags and headed into the
mall. We forgot completely about our plan to eat first.
Chapter Nine - Pam
I always did have a competitive personality so when Cheryl offered the
wager it inspired me all the more. If we missed women's store, or
department, in that mall you couldn't prove it by me. After five hours my
feet were killing me and I was STARVED so I called a halt and suggested
to Cheryl that we grab dinner before heading home.
"We've one more stop to make first," she said. "Gift wrap!"
So we took our purchases, and an impressive quantity they were, to the
department store gift-wrap department, picked out white wrapping paper,
pink ribbon and headed off to dinner. The clerk said the wrapping would
be complete in an hour or two, as she was rather busy. This gave us plenty
of time for cocktails and a leisurely dinner. We selected one of those
prime rib/steakhouse chain places, as it wouldn't be too crowded at that
hour.
We were shown to our table and when the waitress appeared I ordered a
bottle of champagne for a little celebratory toast.
"Wow" Cheryl exclaimed, "very nice. I should have thought of it. We
owe ourselves this. What were the damages?"
I took a calculator out of my purse along with the credit card receipts and
set to work. The waitress brought the champagne on ice; two glasses and
we chatted while I worked. When I was finished I looked up at Cheryl.
"A little north of $500" I said, "plus the gift wrapping of course. We
didn't get everything but we did well, By the way, the gift-wrap was a
very nice thought; I was searching for a way to handle this with Phil and
it's given me a great idea. We always exchange small gifts on the
anniversary of our first date (Phil's idea, he can be very sensitive to these
things) and that is a week away. We always spend that weekend
together...you know...dinner and dancing...so he won't have anything
else planned. That will give me the whole weekend, uninterrupted, to get
this started."
Cheryl agreed it made sense and we reviewed the list to insure we hadn't
omitted anything crucial. Hose, shoes, makeup, bras (just two; Cheryl
suggested a lightly padded A cup but I had my heart set on something a
little more...uh...ostentatious. Cheryl said smaller is better to start.),
panties, two adorable nighties (pricey, but really sweet), an assortment of
skirts and tops (Cheryl said dresses would be tougher to fit and I'd have to
handle those later) and a few lingerie items, garter belts, etc., topped off
the list. Then it dawned on me.
"Cheryl" I hissed, "we forgot a wig!" Phil's hair wasn't that short but it
certainly wouldn't do for what I had in mind. Cheryl just smiled.
"No problem Pam, you can't get a wig for her unless it looks good on her
and to know THAT she's got to try on a variety of styles and colors.
We'll set that up after you get her started. I know you wanted a bigger
cup size on the bras, but she's got to be broken to wearing them. To do
that she has to wear one often and A's can be worn under a lot of things.
Same thing with makeup; we've got the basics but she'll need to refine her
look, experiment with brands, shades...like we do."
Cheryl was so good at this it made my head spin. I wondered how long
she'd been femming Geo... no...Lexi. I hadn't seen her gurl in quite some
time. They'd been over for a Super Bowl party Phil had organized two
years ago but that was it. Lexi and Phil had just not been compatible and
that was one reason we didn't couple up. If only they knew how much
they had in common!
Cheryl continued, "It's the same reason we went easy on the shoes. A pair
of flats and a pair of three inch heel pumps. Shoes need to fit and she's
going to have to learn to walk in heels. I've seen a lot of gurls starting out
who totter around in five-inch heels the first time out. It's dangerous. I've
got a couple of tricks I learned from a guy on the web that really help.
But, that's for later too."
Well, who was I to argue Cheryl was obviously the maestro here. We tore
into the prime rib we'd ordered with a vengeance; I can't remember being
hungrier or more satisfied with a meal in a long time. Our waitress was
excellent and Cheryl gave her a big tip saying, "She'll remember us and
that will come in handy some day."
We returned to the mall to retrieve Phil's treasures. Cheryl indicated
she'd store the things at her place ("Lexi wouldn't dream of snooping in
my office without permission.") and I would stop by to pick them up the
following Friday afternoon. I'd already decided to leave work early that
day to get ready for Phil and Lexi wouldn't be home from work yet.
I arrived home to be greeted by clouds of cigar smoke and a lot of male
machismo bullshit. What is it about poker that causes age regression in
men? I really hoped Phil was enjoying his "boy's night" because I'd
already determined it would be his last. I had no intention of losing that
dollar bet to Cheryl.
The guys all left around 1:00 AM (I got a lot of compliments on the
pastry) and Phil said he'd clean up in the morning. He was a little loaded
(won $100 though!) and went straight to bed. I kicked off my shoes, went
to the office and got online to check for mail. I'd sent a few emails to
married Tgurls websites in hope of contacting their wives, but no luck yet.
Darn.
I was tired too, so I headed for bed; Phil was already snoring.
Chapter Ten - Phil
Christ I hate "customer golf". Had to let that dickhead Graves take me for
fifty bucks at golf; but I got even, and then some. Told Pam I won a
hundred, but it was more like $350. What she doesn't know won't hurt
her and "Jane" will get to do some shopping. I really feel great after
finding that lipstick...my first real scare and I deserve a treat. Pam did a
great job on the poker party preparation so our "date anniversary" gift is
going to be special. I'll spend some of the extra $250 on her. On the
other hand $250 buys a lot of lap dances!
Chapter Eleven - Pam
I woke up early and Phil was still sleeping off the Saturday night poker
game. He'd promised to clean up but if I woke him he'd have a hangover
and be useless anyway. I decided to do the clean up work and perhaps
give him a case of the "guilties" to boot. It really wasn't that bad. He
turned out at 11:00AM and but that time the cleaning was done and I had a
Sunday roast in the oven. He shuffled into the kitchen blushing a bit.
"Golly Pam, I said I would clean the place up."
I gave him a kiss on the cheek and a big hug and said, "Phil, you had a
long day, golf and the card party and (tweaking his nose) more than a few
beers. All I did was go shopping with Cheryl and have a nice dinner."
"Shopping?" he asked. "What did you get?"
I laughed, "We both know what next weekend is and you're just going to
have to wait. Sit down and have some coffee; I'll make you some waffles
and sausage. "
He mumbled a "thank you" sheepishly, sat down and opened the Sunday
newspaper.
The following week absolutely dragged by. I was counting the hours until
lunch on Friday when I planned to leave work to prepare for the big
weekend.
Chapter Twelve - Phil
Chuck called me Tuesday afternoon and told me the guys wanted to hit the
titty bars Wednesday after work. I managed to pick up two pairs of
panties with my stash money but that was it, so I had nearly $250 burning
a hole in my pocket. What the hell, why not? I'd save a bunch for Pam's
gift.
Or so I thought. Went through the whole $250, most of it on a cute little
blonde number. I had a wet spot on my suit pants the size of Texas. Pam
and I never buy big gifts for this. Maybe a nice box of chocolates this
time, I've never done that before. Gotta get that suit to the cleaners before
Pam sees it.
Chapter Thirteen - Cheryl
Pam called me on Thursday and she was steamed. She took Phil's suit to
the cleaners and found a curious stain on the front of the slacks along with
a book of matches from some topless bar in the pocket with a girl's name
and phone number on it.
I made her promise to be really sweet to Phil and not let on. This is going
to be easier than I thought.
Lexi is a wreck. Saw the pile of presents in my office closet! She is going
goofy out of curiosity.
Chapter Fourteen - Pam
Friday! I left work at noon and went to Cheryl's to get Phil's gifts. The
key was where Cheryl said it would be so I was in and out quickly. I took
some time to clean out one of Phil's bureau drawers so he'd have room to
put his "gurl things" away other than the garage. I showered and put on an
extra sexy dress, one of Phil's favorites, and awaited his arrival. I didn't
have to wait long. Phil had evidently left work early too and he walked in
with a gift-wrapped box and a bottle of my favorite wine.
He laughed, "Home early too huh? You're just as eager as I am!" and
proceeded to give me a big hug and a nice kiss. "Here" he said, " your
date anniversary gifts" and handed me the box and bottle of wine.
"Oh Phil, my favorite Chablis and what's this?" opening the box.
"Chocolates, my weakness; you are sweet!" He looked at me half
expectantly expecting his gift but I was going to make him wait a bit.
"Go to the family room, take off your shoes and I'll make us some drinks
and get out the munchies" and shooed him off. We talked for a while and
I poured several more drinks into him and he became very relaxed and at
ease, not a care in the world. Finally, I put down my drink, rose and took
him by the hand leading him down the hall to our bedroom. "Now for your
surprise" I said while turning him through the bedroom door. There on
our bed was an enormous pile of boxes, all wrapped in white and pink. He
stopped abruptly, startled.
"Wow what's all this?" he said.
"Open and see" this while sitting down next to him on the bed. The closet
box contained one of the nighties (no accident there!) a really nice white
babydoll with panties. He began to open it while looking at me
quizzically. When the contents were revealed his jaw dropped.
"What the hell?" he said with more than a trace of agitation in his voice.
I took his hand and looked him straight in the eye and said "Phil honey, I
found your things in the garage." Now I've heard the expression about the
color draining from a person's face but that would not due justice to what
happened to Phil. He went positively WHITE; he started to speak several
times but just couldn't. When it finally appeared he was about to get a
word out I stopped him.
"Phil, sweetie, it's OK. I admit, at first, I was upset; frankly, most about
the fact you deceived me. I gave myself some time and did a little
investigation and got a real education about crossdressing and the whole
business. It's OK. After a while I even found it kind of exciting. You
have to admit that you haven't been exactly prolific in bed for some time
and this just maybe the shot in the arm we needed."" Phil smiled the smile
of the condemned man told the time of his execution had been moved
back two hours.
He spent the next 15 minutes blubbering a tearful apology and his
gratitude for my understanding. I was startled, I'd never seen him so on
his heels and submissive and...well...weak. Finally, to allow him the
time to compose himself, I went to fix two more drinks. When I returned I
had him start to open the remainder of the gifts.
Chapter Fifteen - Cheryl
It was Friday night and my thoughts were with Pam, wondering how it had
gone. That was forgotten however when I met Greg after work and went
to his place for the evening.
I arrived home around 11:30 and Lexi was of course still up. She'd
known I had a date. My pantyhose were in my purse and I was dripping;
Greg is a rather heavy cummer and I was still full of him. I slumped on
the couch as Lexi came into the room and I beckoned her toward me with
a crooked finger. She slipped to her knees and slid my panties off as I
raised my hips to help her. When they were off I hooked my right ankle
behind her head and pulled her face to my mound. She went eagerly to
work. After a minute she pulled her glistening face from me and smiled.
"Mmmmm" she purred, "Greg, my favorite." And immediately returned
to her task with renewed vigor. She is so good. In a few minutes I was
shuddering through an orgasm, not my first of that particular evening.
Lexi had cleaned me out pretty well but there was still more. I pushed her
to her back on the floor, straddled her face and lowered myself. Gravity
finished what she had started and I let her lap it up until I had climaxed
again.
Chapter Sixteen - Pam
It took quite a while to open all the gifts. As time went by Phil became
more relaxed and began to look forward to opening each gift with ever-
increasing enthusiasm, such a little boy. We showered together and
prepared for bed. I handed him the white babydoll saying, "This one
honey, it was the first." He slipped the top over his head. When the
panties went on they barely held his erection in check. We made love and
Phil quickly slipped into a deep sleep. I went to the kitchen for a last glass
of wine and cigarette. Phil had been better in bed than he had in a long
time. I sincerely hoped he enjoyed entering me because it wouldn't
happen many more times.
Chapter Seventeen - Phil
I could've kicked myself in the ass. Those years of hiding it, all the things
I wanted but couldn't have, the fear of discovery, all for nothing! Pam
loved it. I fucked her silly; she was bouncing around like a crazy woman,
as turned on as I ever recall. Damn what a night to remember. When I
woke up, my head was a little woozy from mixing the drinks and wine I
guess. And Christ we never had dinner, just the snacks with drinks.
Pam was already up and came into the room bearing a cup of coffee.
"Up and at 'em sleepy head" she chirped, "we've got work to do. You've
got to try all this stuff on so I can return or exchange anything that doesn't
fit. Shower first so you're clean and these" she said smacking my legs,
"get shaved."
"What?" I croaked
"You're going to look damn foolish in a short skirt wearing nylons over
hairy legs."
I fought back; "Yeah, but who'll see me?"
"I will" pulling me out of bed, "and it would gross me out. I didn't do this
for you to look silly. Get going." The last came with a shove toward the
bathroom. I showered and shaved my legs from about mid thigh down,
toweled off, combed my hair and went back to the bedroom. She pulled
the towel from my waist and appraised my effort, scowling.
"Not much of a job, but it's a start. Here, panties and panty hose, we'll
start with the skirts."
The panties went on OK but the pantyhose were a pain. Pam laughed at
me and showed me the right way to put them on. As they slid up my
shaved legs I got an immediate erection.
"My" she mused, "you DO like this a lot."
We got through all the skirts without incident, save the last, an obscenely
short spandex mini skirt. She just shook her head.
"What's wrong?" I asked.
"Go look in the mirror. Notice anything?"
I did as she suggested. The line where I had started shaving my thighs
was well below the hem of the skirt and clearly visible, matted hair above,
smooth and clean below. "Yeah, well it's the first time I've done this
shaving stuff."
"That's not all. What else?"
Gulp. I saw the noticeable bulge in the front of the skirt.
"Don't you know how to tuck that thing away?" Down came the
pantyhose and panties and she showed me. "Good thing I did a little
research." We finished and she arranged me in front of the mirror. "Much
better." And it was better. The guys in college used to rib me about the
size of my dick when gang showering; it was now turning out to be an
advantage.
Everything went well except for these sort of loafer type shoes she had
purchased. They were too large and had to be exchanged. She finally put
together a complete outfit for a trial run and seated me in front of her
vanity.
"Now for a little makeup"
Oh man. But first she grabbed a pair of tweezers and pulled out some of
my eyebrows saying she had to get rid of strays.
"We'll do more as time goes by. Just a little at a time so it's not obvious."
The high heels went on OK and felt surprisingly good. She was rather
critical of my walk ("like a cow" as I recall) but we'd work on that. After
the makeup and a pair of clip on earrings she had me look in the mirror.
Not bad... not bad at all. The hair looked weird of course but the rest was
amazing. Pam looked rather pleased in fact.
"Not bad...uh..." she paused. "What DO I call you when you're a gurl?
You must have a gurl name for yourself, no?"
I muttered "Jane."
"Jane? JANE?" she snickered, "Plain Jane maybe. We can do better than
that, but no hurry. Come on grab your purse. I'm going to exchange those
shoes and you can keep me company".
I blanched.
"Oh, big sissy, don't worry you can stay in the car. It won't take long."
Off we went. I sat as low as I could in the passenger seat. She wouldn't
let me drive with the heels on, saying, until I learned, I might kill us both.
When bedtime arrived she told me we'd finish off the shaving I'd started
in the morning. After using my trimmer and a razor all I was left with was
a very feminine looking pubic triangle. We cuddled in bed and she
stroked my ass and legs.
"Mmmmm, smooth, nice, sexy" and with that opened her thighs and rolled
me on to her. Man was I ready for action. I don't think we'd screwed
more than twice a month for a long time; now it was two nights in a row
and looking like more. Hot damn.
Chapter Eighteen - Pam
I never imagined it would be so easy; Phil was like putty in my hands.
Cheryl had been right about everything; God love her. I called her on
Sunday while Jane (We'd do something about that name.) was playing
with makeup (a butcher job, but she had to learn) and gave Cheryl a
complete recounting of the weekend's events. She said I'd done her
proud. We talked for over an hour and she filled my head with dozens of
ideas, tips and tricks. The picture of Lexi came into my mind and I knew
she knew all about them by now too.
In a matter of weeks my perception of Phil had changed dramatically.
Some of the things Cheryl told me on the phone would have upset me
before but now they were not only interesting but made perfect sense. Phil
had been a very ardent lover over the weekend but it was MEN I found
attractive and Phil wasn't as much of man as I'd thought previously, and
seemed destined to become less so as time passed.
Chapter Nineteen - Cheryl
It's been three weeks since Pam's "big weekend" with Phil and Pam says
her gurl is coming along splendidly. Pam says they practice with makeup
every day after work and her Jane (I don't like the name either) is almost
decent at it. Pam has been slowly replacing the guys' briefs with panties
and has Jane wearing a bra whenever she's not at work. From Pam's input
my guess it's only a short time until she gets her gurl out. I bought the
digital camera and gave it to Pam to use for a while (Lexi was very put out
that I'd loaned it) and told her to take plenty of pictures.
Chapter Nineteen - Pam
On Monday morning Phil complained he didn't have any clean underwear.
I told him to wear a pair of panties to work, who'd know the difference?
"Yeah" he said, " but how about when I use the restroom?"
"Just use one of the stalls silly; if you don't have the panties down around
your ankles no one will notice" I pointed out.
Her makeup is coming along nicely and the slow daily plucking of the
eyebrows is starting to bear fruit. She's doing much better with the walk,
even starting to wiggle her backside a little.
I stopped after work on Monday and picked her up a pair of slacks, pale
green, and a white knit pullover top, sleeveless. The slacks have a side
zipper and the top has a short zipper at the back of the neck. The top is a
lightweight knit so her white bra should be clearly visible. When I got
home she was already dressed and was almost finished with her makeup.
"Hi sweetheart" I called on entering the house "almost done with your
makeup? When you're through come to the family room, I have a few
things for you to try on."
She appeared a few minutes later and the makeup job was the best yet.
"Oh" I enthused, "VERY nice, dear." She blushed. "Here, try these on" as
I handed her the slacks and top. The top fit fine and as expected the bra
stood out nicely. The slacks were a little small in the waist though.
"Well" I said, arms folded, "that settles it; it's a diet for you gurlfriend.
You need to take off a few pounds, especially in the waist. We'll start that
tonight. There's another thing; the top looks great on you, but not with
those underarms. They'll need to be shaved. You don't have much hair
on your chest, but clean that up too, OK? There's a little 'shadow' visible
through the top."
"Uh...well...OK" she responded, "I guess that'll be OK."
"Great, go do at least the underarms quickly and I'll make us two small
salads for dinner." She swayed off to the bathroom and I went to the
kitchen to put together a light dinner. I could stand to lose a few pounds
myself. When she returned I said, "Let's see." She showed me and I said
"Much better." I peered intently at her eyes and then commented "Big
improvement with the mascara over the last week sweetie, you're getting
the hang of it."
During dinner she commented, "I don't seem to have enough of my men's
underwear."
"I pitched some of it because it was a little worn, honey. Besides,
maintaining two complete wardrobes would cost a bit; we have to double
up where we can. I think I'm doing pretty well with this so it's only fair if
you meet me halfway." What could she say? She mumbled her
agreement and I broached another subject.
"Dear, one other thing" I continued "I work and keeping the house clean is
time consuming. I know you don't mean to, but you splash a bit when you
use the toilet, would it be too much to ask you to always sit? You'll be
doing it at work so you should get into the habit anyway." She had no
problem with this either.
Another threshold crossed.
Chapter Twenty - Phil
Well, panties to work again. That makes every day this week. Fell sort
good though, kind of a kick too. Graves called me about golf on Friday,
said we'd play at his club Friday afternoon, shower there and then grab
dinner. I accepted. After I hung up it dawned on me! How the hell could
I use the shower room there looking the way I did? All shaved and
looking...well...sort of "pussy". Called Graves back and told him I'd
have to pass on the golf as something had come up but would meet with
his group for dinner.
One of the ladies in the office stopped by. I had taken my glasses off to
clean them and she looked at me with an odd expression, oops, the
eyebrows. Made a mental note to get some thicker frames.
I mentioned the glasses to Pam at dinner (another light one, Christ I am
always hungry these days!) and she agreed. She also a suggested I try
contact lenses for when I was a gurl; she said it would be a shame to have
my eyes looking so nice and then cover them up. She is a sweetheart.
Needed a haircut this week but Pam told me to wait until the weekend as
she was working on something in that regard. Sex with Pam has been
great; she is really becoming aggressive. She was never much for giving
head but lately, wow. Damn, and when she pushed her finger up my ass
the other night while doing it drove me nuts, what a gal.
Chapter Twenty-one - Cheryl
Met Pam for lunch today to give her the address and phone number of
Emily's wig boutique and a Tfriendly salon for Phil. Pam has been
sending emailing me the pics she's been taking and that had an unexpected
benefit. We'd been chatting about her plans for the weekend when she
brought the subject up.
"By the way Cheryl, thanks for the loan of the ecam. I know I take a lot of
picture of her, even when she's changing from boy to gurl, but what did
you think?" she asked.
"Pam" I responded, "you're doing just beautifully, I think she's just
darling."
Pam blinked and looked at me. "That's it!" she exclaimed.
"What's it?"
"You given me the name...Darla...when you said the word 'darling' it hit
me. It's perfect!"
And so it was.
Greg called me at work later in the day. He said he'd shown Lexi's
picture to a bi friend of his (who absolutely adores TGurls) and the guy
was smitten. Poor Lexi's been restricted to the guys she meets at the
Tclubs or online and she was overdue for a surprise. It's been ages since I
brought a man home for her and I always enjoy it when we can do things
together. Greg said we could get together after work for a quick drink so I
could meet the guy and check him out. I've no interest in him but I have
to take care of my gurl.
Chapter Twenty-two - Pam
I couldn't wait to get home to tell Darla she was Darla now! A quick stop
had be made first at one of the local adult bookstores to pick up a few
items Cheryl had suggested. She was right; Darla had gone goofy over the
anal stuff so the balance of her training could commence immediately. I
purchased a few vibrators and dildoes in various sizes from small too not
so small and a nice strap on for me. (This while being leered at by a bunch
of perverts.) That would come later of course. I had to put THAT away
where Darla wouldn't find it (certainly NOT the garage!).
Darla loved her new name. She must have repeated it twenty times, in that
squeaky little voice she's working on. I told her we had plans for
Saturday so she should not get in to late from her dinner on Friday.
Cheryl and I are meeting two guys she knows after work on Friday for
drinks, and nothing more. I just miss the company of a man a bit I guess.
Saturday morning arrived and I set Darla to a little housecleaning (whined
a little about that) before she got ready. Friday night was great. The two
guys were fun and real gentlemen. Cheryl said the one has been after her
forever and the only way she agreed to meet him was if he brought a
friend a long for me. I am gaining a real insight into Cheryl's social life.
It was a nice evening; I needed a break from Darla.
I put Darla on the scale and she's lost three pounds, the bitch; one ahead of
me. I had Darla put on the new slacks and top I'd purchased and gave her
two more presents, a decent sized black purse and a pocketbook to put
inside. The slacks were fitting better already.
She came out of the bedroom when she was ready.
"You look great" I said, "here put this on". It was one of my favorite gold
chains and looked nice with the white top. She did look sweet, decent
makeup and the small gold clip-on earrings. I tried to do something with
her hair but it was a waste of time. I sat her down and quickly put a set of
press on nails on her after sorting out the larger sizes from two packages.
Darla had, to my knowledge, never done that and it would've taken her all
day. When I was done I said, "Gurlfriend, you and I are going shopping."
"What?" she yelped.
"Don't worry, nothing heavy, the wig boutique first, then the optometrist
for new frames and contacts. You need a haircut too. I found just the
right place; your barber is a butcher. After that we hit the shoe store.
You're doing much better with the heels so I think you're ready for a
higher heel and one pair won't be enough. We're going through a bit of
cash here so it wouldn't hurt if you cut back on the golf a bit. Come on,
I'll drive."
We went out to the garage and got in while the door was opening. When
she saw the garage door going up she moved a little faster, coward. We
headed for Emily's for the wigs, I was sure we'd get two at least. On the
way we stopped at a light and a car with four teenaged girls stopped
alongside. I'd forgotten how they scope everything. They can read a
BOOK at three hundred yards. It took one of them about five seconds to
read Darla (the hair made it easy of course) and for the giggling and
whispering to start.
Darla picked it up too, turned the color of a ripe tomato and slid lower in
her seat. It was a deliciously long light, alternating left turn lanes and
everything. The girls got a little less careful as time passed and just the
before the light went green I heard "He IS precious" followed by more
giggling. Hmmm, "Precious"...nice name...but no "Darla" it would stay.
We arrived at Emily's shortly though it must have seemed like years to
Darla. I could see her tense up until we cleared each light. She'd relaxed a
bit when the road narrowed to one lane. We were a bit early for our
appointment so we had a seat. There were four other customers there, two
women and two TGurls, one rather pretty. Cheryl had advised that
Saturday was the day most of the TGurls would come in and that might
put Darla more at ease. It did. Cheryl knows what she's talking about.
In a few moments, Emily approached us, a rather handsome woman in her
late fifties or early sixties and asked me "Are you Pam?" I said I was and
Emily looked at Darla. "And this is?" I nudged my gurl.
"Oh" she piped "Darla."
Emily held out her hand and said "Come with Emily Darla dear, we'll get
you all fixed up." Off they went with me in tow.
We spent an hour plus there and I lost count of the number of wigs Emily
tried on Darla. We finally settled on two, a fuller blonde one and a rather
longer auburn one. They were both very high quality wigs and never
having purchased one I was a bit surprised at how pricey they were. It
was decided that Darla would wear the blonde one home so Emily styled it
for her and off we went. It was a different Darla on the way out to the car.
She wasn't in quite a hurry as she had been when going in; she had
received a real boost in confidence. We had one down and three to go.
Chapter Twenty-three - Darla
The ride to the wig place was fucking hell. I was hoping those young
cunts would be too busy yapping at each other to notice but they were on
me like white on rice. I was starting to think the goddamn light was stuck
but we finally got away. The wig place was a lot easier, and man what a
difference! I looked very good. I figured, with the hair the car trips would
no longer be so bad.
The optometrist was a breeze. He's an old guy and the joint was empty.
Picked out new frames and got fixed up with soft contacts. Pam wears
'em and she said she'd show me the ropes there. She is being so cool
about this it's scary. I'm feeling a little guilty about all the dough we're
spending on this so I'm going to have to do something to make it up to
her.
Graves was a little miffed about me not playing golf on Friday. He did do
a lot of work setting it up for me to meet those guys, but I'll figure
something out. Hell, I always do.
The shoe store wasn't so easy; it was a small women's specialty store.
Pam said there was no way I could handle the mall on a Saturday
afternoon yet. It had started to rain a bit but luckily we grabbed a parking
spot near the door and got in just as it started to really pour. Pam had been
there before, for herself, but said that since my feet weren't that large
(guy's size 9) I could probably get away with a 10W in women's and
they'd have that. The problem was the sales clerk, early 20's and well, a
bitch. Just talked through me like I wasn't even there.
When she walked up to Pam she took little notice of me as I was standing
a bit to the side "How can I help you?" she asked Pam.
"Not me" Pam said, motioning with her head toward me, "we need
something for her."
Then she looked at me again and I could see she tumbled.
"Oh" she said.
It wasn't just the word, it was the way she said it; you know the way
broads can make it more of an accusation than anything else? Well, it was
clear to me that I was lowlife dog meat as far as she was concerned.
The clerk looked back to Pam and asked, "What size does she wear?"
"She's new at this so we're not sure" Pam replied, "my guess is probably
a 10W."
"Let's measure, sit here."
I sat down as ordered (glad Pam got me the slacks) and she took my
loafers off to measure. She took my right shoe off and then looked up at
me.
"No polish on the toes?" she asked. Pam just smiled. I was fuming but
said nothing.
We wound up getting three pairs of high heels for me, one pair was really
high or so it seemed to me. The clerk told Pam I'd have to practice a lot
with the higher heeled ones so I probably shouldn't wear those home.
Pam agreed and said I'd just wear the ones I had worn into the store. The
tab was over two hundred bucks with tax! The rain had slowed way down
by the time we were ready to leave, just a drizzle really. So we jumped
into the car and headed for the last stop, the barbershop.
Chapter Twenty-four - Pam
I wonder how long sissy is going to call it a "barbershop". It's a very nice
unisex salon a little on the outskirts of town but not too far out. All of the
operators are women except for Paul. If Paul isn't gay then I'm the Pope.
I mean really swishy gay. Cheryl warned me to avoid him, as he did not
think much of what she said he called "drag queens". We got Bernice
who was very nice. I guess she does Lexi's hair and Cheryl clued her in
not to divulge that.
All the other customers were women except for a guy who looked early
20's, and very good looking at that. He was waiting for another operator
and reading a magazine. He didn't pay any attention to Darla 'til the wig
came off and then he smirked a bit but was pretty cool about it generally.
Bernice said, "Not much here to work with yet so we'll just trim it a bit.
I'll take some pictures so when you come back I'll have a few ideas for
you too consider. You might want to pick up some magazines and see if
you can find something you like as well."
Bernice did the work quickly and took some pictures. She then replaced
and quickly restyled Darla's wig. Bernice said they had some kind of
computer software that could be used to illustrate how various hairstyle
might look on a person, ah, technology. When we left the young guy was
getting his haircut and he gave me a very nice smile as I passed. He was a
hunk.
Chapter Twenty-four - Cheryl
Pam called Sunday to give me the scoop on Saturday's activities. Talk
about a fast study. I thought the bet was a sure thing, now I'm not so sure.
The pics she's been emailing are impressive and I haven't even seen Darla
in a wig yet. I guess I get those tomorrow.
"What are you up to today?" I asked after a bit.
"Not much. Darla's been prancing around in her new heels since we got
home yesterday. She'll probably want to sleep with them on." We both
laughed at that. "We forgot to bring the mail in yesterday so I told her to
do it. She did but the little priss waited 'til midnight to do it. She still
doesn't have the hang of walking in heels yet of course but if she shakes
her tush any harder it'll fall off. We wouldn't want THAT." (BIG laugh
on both ends)
"When do you think Darla will be ready for her first trip to one of the
Tclubs?" I queried.
"A couple of weeks yet I think" Pam returned, "she's starting to add more
in the way of make up and I want her looking really hot. I'm still after
your dollar you know. I'm picking up false eyelashes this week: that
should keep her busy for a while. Also, bought the toys already so our
bedroom habits will start to change this week. The thought of doing her
with that the strap on makes my knees weak but I'm saving that."
"Yes" I said, "timing is everything there. You'll break her. Just don't
spook her with too much too soon."
"You told me what a good little pussy lapper Lexi is and I'm looking
forward to that. I'll let Phil, oops Darla, screw me once or twice this week
and maybe once next week but that will be it."
I laughed. "By the way, Eric told Ted he'd love to see you again."
"He was very nice, but I'm waiting until...you know...after."
"Smart of course; it won't be long anyway. The ocean is full of fish."
"I'm looking forward to taking Darla to meet you and Lexi at one of the
Tclubs. I can't WAIT to see the looks on their faces when they figure it
out, what a hoot. It's going to be a long few weeks but worth the wait.
Are we going to settle the bet then?"
"No, that wouldn't be fair. I had a BIG head start with Lexi. We
should've figured out the timing when we made the bet, no hurry now."
"Since you told me Lexi was so good with the liquid eyeliner I got some
for Darla. She spends HOURS every day fooling around with makeup
now. I figure this will keep her focused on being femme AND it'll be
another way to settle our bet. I also got nail polish for her, she'll do my
toes, and I'll do hers. I hate doing that. Eventually she'll do both of
ours."
Pam was really getting with the program. I could almost see the wheels
turning in her head as she spoke even on the phone. Once again images of
the beginning with Lexi came back Darla didn't know yet how things
would change and Lexi had probably forgotten how they were. An
interesting juxtaposition that. If they got to be good gurlfriends it would
be wonderful. Oh well, time would tell.
Chapter Twenty-five - Darla
I'm getting the hang of this shoe deal. My feet were sore because the
shoes were new and I just wasn't used to them. Had to learn to walk all
over again. The problem is that in the house I just can't walk very far.
I'm going out for the mail every night, real late, and that helps but not
much. It's only once a day after all for just a few minutes. I mentioned it
to Pam and she said not to worry I'd get more practice soon enough.
Shortened my stride quite a bit and that has helped. Pam is also showing
me how to sit, etc. I never imagined there was so much to learn.
I adore my new wigs and of course the other things Pam helped me get.
I'm keeping most of my things in a spare bedroom so our bedroom doesn't
get too cluttered. Pam thought of this too; she also said a new dresser or
bureau for the spare bedroom would make sense as well. The space is
there.
Having one hell of a time with the eyelashes she got. Just can't seem to
get them right. Either they're crooked or they fall off or some shit. Glad I
got the new eyeglass frames. The inside ends of my eyebrows now start
over the inside corner of each eye and are much thinner; I told Pam they
were thin enough but she said a little more wouldn't hurt.
One of the senior partners is having a pool party for the firm in about 6
weeks. I wonder if Pam will let me stop shaving for a while so we can go?
Chapter Twenty-six - Pam
Well the week started off with a bang so to speak. Darla and I made love
as man and wife for what turned to be the last time. Funny, I thought it
would take longer. That was Monday night, the same night we polished
each other's toes. We used the same polish, a "togetherness thing", which
was a nice bright red. I showed her how to keep the toes separated and all.
I did hers perfectly but she made a mess of mine, oh well, nothing
permanent I guess. I told her that from now on she should do both of ours,
as it would be twice the practice for her. She readily agreed.
On Tuesday after dinner I gave her a big hug.
"What's that for?" she asked.
"Because I love you and you're such a sweetie. I can tell you're sitting to
tinkle like I asked and I appreciate it so much. Besides, you may have
helped yourself. It appears as if I'm going to be putting more time in at
work so could you be a dear and start taking care of the bathrooms?"
"Of course" she replied cheerfully.
"MMMMuhh" as I gave her another big hug and a smooch on the cheek. I
noticed I'd left a lipstick smudge on her cheek so I quickly took my finger
to her cheek to remove it. When I looked at my finger I exclaimed, "My,
my, foundation and powder and I didn't even notice. You're doing very
well indeed." She was wearing thigh highs so I reached up under her skirt
and stroked her ass. "Mmmmm" I murmured as licked her neck,
"smooth."
If she had been any more pleased she would have soiled herself.
"Off with you l'il bitch" as I pushed her toward her work with a pat on the
bottom, "do the bathrooms and it'll be a treat in bed later." She minced
away with a wiggle in her walk and blew me a kiss over her shoulder. She
was progressing so very nicely.
It was later. She'd taken a shower and was slipping on her nightie top as
she came into the room. She saw some of the toys on the bed and the lube
on the nightstand.
A little non-plussed she said, "Who are those for?" and paused.
I patted the bed next to me and said, "Sit here sweet stuff we need to talk a
bit. First of all these things are for BOTH of us. You've plainly enjoyed
the things I've been doing to your little bottom lately. And, not to be
unkind dear, but you're not exactly...uh...blessed down there and you sort
of rattle around in me a bit. I've been very good about...well...giving you
head and I thought you might enjoy reciprocating. These marital aids
(lovely term) will enhance everything for both of us."
This relaxed her noticeably.
"Uh...gee...OK...I guess" she replied, "but they look sort of big for me,
you know?"
"Don't worry baby I'll be gentle, very gentle. I have confession to make.
Because of your...uh...equipment there I really don't have orgasms very
often and it's been a while for me. I am REALLY hot for you and
wondered if maybe you'd do me first OK? Maybe start with some oral
and then this" while indicating the largest dildo.
"I...gee...I know I'm not the biggest" she started. (An understatement if
there ever was one!) "And well you've been phenomenal to me and I'd be
glad to do anything that pleases you." Well, "anything" that pleases me
was not what I had in mind; I was thinking more along the lines of
EVERYTHING that pleases me but this was not the time to push that
button.
Long story short, she got her face in there and really went at me with a
will. About the time I had my second orgasm, I told her it was my first
(God, men can be so pathetic.), I had her start with the dildo while she
licked me. The thing wasn't huge but it was easily two of her and it
wasn't long before orgasms three and four hit. I still can't believe I'd
never thought of this before. I was exhausted but this was no time to risk
losing control. I returned the favor and used the smallest appliance on her
backside while I sucked.
I took her to the edge several times and back down again. When she did
finally get off she couldn't have walked out of the house if it was on fire.
After that night I literally owned her ass. For the balance of that week and
the next I worked with one plan in mind. Less and less reliance on oral
and manual stimulation and more on the toys in her butt. The ultimate
goal was of course to have her get off strictly from anal but I was saving
that for the strap on.
Chapter Twenty-seven - Darla
God bless the web. Pam didn't just study this I think she wrote a book.
My knees have been like jelly for two weeks. Not only that, the prettier I
look the better it is. Pam gets wild when I look my sexiest. We actually
did it in the family room once she was so impatient. Glad I wore the
garter belt and stockings; she would have ripped panty hose off! Pam says
she working on something for me regarding practice in walking in heels.
It could be half time on the fifty-yard line at the Super Bowl for all I care.
Chapter Twenty-eight - Cheryl
Pam has been keeping me up to speed by phone almost every day. Looks
like good old Darla's coming along nicely.
I was going to need Lexi's cooperation to help Pam so I set up a little treat
for Lexi. I made arrangements to have Greg and his bi friend Tony stop by
on a Friday evening and told Lexi we were double dating at our place. The
little minx almost juiced herself on the spot.
We started to get ready right after a fast supper. I was in the living room
having finished first. I was sipping a drink when she walked in. Wow.
Never saw her look better. Side-slit skirt with buttons opened fairly high
up, garter belt and hose showing nicely. Her hair and nails were perfect
and with her patented "I'm a whore" look makeup there wasn't a man on
the planet who wouldn't do her, TGurl or no. While she mixed herself a
drink she looked at me and winked.
"Panties on top" she giggled.
God she was ready for fast action, no fooling around there. When the time
was right her TGurl pussy wouldn't have to wait for garters to be undone.
The guys arrived fashionably late; Lexi provided them drinks, turned the
lights down and slapped one of the adult videos I'd rented into the tape
player. Lexi snuggled up to Tony on one couch; I was on the other with
Greg.
I was very horny but wouldn't miss watching Lexi in action, at lea