Looking for Tess, Dressed just So
by MadQuill
Please remember this is a copyrighted work and all legal disclaimers
apply.
This story is a subtly revised version of the story "Dressed So". The
intent is a response to a comment from a reader. She suggested that the
story "belongs in the Lesbian category. I arrived here from a 'stories
like this reference'. I found myself captivated by your series that was
romantic, with character development, and quite different; re: lesbian
and transwoman. Never thought about this possibility in real life. You
created a beautiful story that really excited me erotically to a
different possibility.
Looking for Tess, Dressed just So
As evening approached I entered my dressing room and set the glass of
Chardonnay on the bureau. I had planned to wear a simple black dress but
decided the white V-neck with a fitted waist and open back would look
best. I'd lost nearly two kilos due to my work regiment the past two
weeks and decided to enjoy the slimness this evening. The mild winter
allowed some freedom from the boots and long sleeves and a sheer nude
pair of hose' would suffice. After trying several pairs of shoes I
selected white pumps with a 110mm heel, and ran the seven bangles passed
my left wrist. I pulled my long hair up into a simple knot and grabbed
my evening bag, pausing at the mirror I checked out the outfit and
smiled sure I was ready.
Dressed just so I would search for my lovers in bars downtown, near the
river, where the lesbians were of no notice. I'd come to this process by
accident a few years ago while visiting a friend at a Cambridge college.
Sarah was a tall brunette beauty I'd met late in high school. She was
from a rival town and I hadn't realized, that she was gay and that she
was attracted to me. I'd blossomed late and at seventeen years old was
over 175cm tall and a bit chucky at 70 kilograms. As my senior year came
rushing on I'd lost the weight and settled at 178cm. My mother had been
a stunning tall maiden my father had said many times but I'd taken
little notice of her beauty since I had been clearly an awkward teen.
Anyway, Sarah had come into the restroom a moment after I had finished
in a stall and was washing my hands. She stopped when she caught a view
of me in the mirror.
"You're not like these others girl. With no makeup, dressed like that,
and just running out? Not even a little lipstick?"
I'd not realized she was addressing me until I turned to my left as she
crowded me. The others seemed used to her and just muttered.
"We're hunting here girl, and you don't seem to understand the
importance of presentation? Granted you are lovely but these smelly
jocks with bad vision need help with their gene selection. Mating is
what keeps us going and you're not helping them nor yourself."
We became friends that weekend and when she'd traveled east for college
I did so as well. The second month of college I traveled on the train to
stay with her for the weekend. After a simple dinner she brought me to a
club that had a lot of women, shit, it was only women. As we entered and
she started to introduce me to each of her friends I realized she was
gay. The looks of near rage and hate passed back my way showed me that
they had deduced I was her lover. Maybe she had prepped them, maybe not,
but several of the girls we met were pissed.
At the bar and on the dance floor there were women of all types, cute
and slim, large and butch; some were dark and angry. There was another
group of quite well dressed girls as well. I tried of the aggressive
stares from Sarah's friends and moved across the room and started a
conversation with a lovely blonde in heels. She smiled when I said I
liked her skirt, a soft olive green but of cashmere.
"Thanks, I'm Gerri. I love the feeling on my legs, and it was on the
discount rack at the Limited. Most of the other girls here don't share
with us. What's your name?" I was about to give her my name but thought
about her comment.
"Why won't they 'share'? Are you from a different College or planet? Or
worst, the visiting team?" At that moment I felt my arm being grabbed
and turned to find Sarah at my left.
"We keep to ourselves Maddy. These 'girls' aren't female. They may look
like us but their fakes."
Sarah had me across the room quickly, "Couldn't you see that 'she' was
actually a boy? Come on Maddy! The bar allows only 'women' but doesn't
discriminate so those girlie guys get passed the door."
Maybe it was her sense of style or it might have been her studied
beauty. Instead of wearing jeans and flats with just a bit of makeup
like Sarah and me this woman was dressed; hose', jewelry, the heels,
even her hands were beautiful. As Sarah went off about 'them' I
wondered about Gerri. She didn't leave my mind the rest of the evening.
Thinking back to that weekend eight years ago I know Gerri affected my
life as well as my personal style. I've found I loved preparing for each
day whether to just go to work or to go out on the town. I'd realized I
loved being dressed beautifully and at a significant cost all of the
time.
Late that night years ago Sarah seduce me. I became aware of the loving
women offer. We were discussing the differences of lesbians and 'them'
for over an hour when I'd reached to grabbed my beer and she kissed me.
Our pent-up sexuality had control and she led me to her bed. I watched
her lovely bottom as she removed her jeans. Seeing a bare mons for the
first time I realized I had much to learn. I loved the nakedness, the
smooth skin near her pussy and she was very good at loving my body as
well. I had touched myself but Sarah was my first lover. We made love
atop one another in what I later learned was sixty-nine. She had some
very good cannabis and soon we were hungry.
On the walk to the Diner we saw the same group from the bar and the
discussion started between us again. To her these other girls weren't
quite right. To Sarah they stood for all the wrong things and messed up
the queer agenda. It took more than ten years for Sarah and her type of
female to accept that these other girls were in fact in need of support
and could add to the agenda rather than distract from it. I didn't care
for any of her mis-directed politics. The subdivision and attitude of
belonging to a group was destructive. Near 3am I'd stated what I
realized. I was attracted to girls who had a penis. She cried a little
and we hugged. Early as the sun entered her room I awoke to see her
naked bare body and I stirred her with my tongue. We had the best
release when scissoring each other; her naked pussy on my furry mons. I
knew I was going to love women from that day on.
Now I live in a Canadian city where the subculture of sex isn't treated
as a negative, just part of life. My friends are from many political
camps, and lifestyle issues aren't cause for segregation. My career has
evolved to provide me with an ample salary and the freedom from the
office suite. My professional work allows me to set my schedule and for
whom I'll produce. But my love life has stalled. I've had many women
lovers but my interest in beautiful women with a special bump hasn't
been sated.
After school I lived with an older high femme and she nurtured and
developed my appreciation of style and the role it has come to play in
my life. Clara also helped me become aware of my omnisexual nature. At
thirty-five her body was still taut and smooth. I loved the nakedness of
her vulva and her spirited loving seemed like an adventure. Each night
she would find some new way to get my attention and bring us to peak.
Her loving was as special as were her relationships. The time spent with
her girlfriends and her toys slowly helped me understand my nature.
Meeting independent females whose appetites were so varied was
important. Her friends and ex-lovers were of course years older then me
and there was an openness to our relationship. She taught me the
importance of submission as well as penetration. Her world was
comfortable due to an inheritance and we loved each other sincerely. I
think she wanted me to stop working but she had shown me that I was
still exploring and growing. Having been her lover for sometime I'd
eventually introduced some of my girlfriends.
"The transwomen you've been with Madeline are really more or less femme
lesbians not shemales. You seem to select only the girls able to pass
without question. They're all small-breasted girls too. Two I've met I
wouldn't have guess their birth gender if you hadn't suggested their
history. I really liked that babe from Canada. What was her name? I
would have slept with her in a heart beat."
Jenna was what had drawn me to Canada. She was amazing woman about ten
months older whom I'd met the summer after college. She had studied near
me and we'd crossed paths several times. She must have been living with
one of Clara's close girlfriends for we met again at a cocktail party in
a garden.
"It's been, what, two years Maddie?"
She looked wonderful in a vintage floral dress in white with a gradient
flower print. She was very comfortable amongst the group of successful
lesbians gathered in mid-July.
We'd kissed cheeks and I'd introduced my lover. "Jenna, more than three
but let's not count the years."
The following day Clara suggested, "I see your old roommates, these
other girls, as a research project. You are trying to decide just how
much cock you needed. I'm more casual when it involves a penis.
Sometimes I just want to suck some dick."
She and I drifted apart after spending three years together. My
professional path got in the way of her travel. She would call from some
exotic place and ask me if she could sleep with a girl she met or some
cutepie with a nice cock. I didn't want to get old with Clara but
looking back she was a mentor.
Since resettling in the north I'd been with Jenna and two other very
different transfemmes. My heart went flat last spring when Lisa informed
me that she had come to the conclusion she wanted a vagina. I love
vaginas but having my own is plenty. I needed someone or something to
fill mine. The break-up lead me to realize I had been searching now for
eight years, had lost four serious romances and yet I was a selfish
lover. Sure I had helped each, four beautiful 'girls' and two gorgeous
femme lesbians, but I'd restricted my heart. I'd told myself I was
protecting it but I was purposeful. I kept an eye on my girl's
development anticipating their next move. Maybe that was a trait I'd
learned from Clara. She wasn't to blame for my failure to commit though.
I knew there was chance each would move on, something would lead to a
breakup as their needs changed. I had felt I was in love with the four
but I was just enjoying, lusting for their individual beauty. Lisa was
the latest and near to my heart. We'd been living together for five
months. She was a few years younger and though beautiful, had real
conflicts within about her sexuality.
I'd thought we'd worked through her issues and hoped we'd be together
for a long time but as she said when she was packing, "You just love the
scent and feel of my body. The twin characteristics that make me a
special lover and a woman. But you don't love me. I'm a person that
grows and does change; I've evolved Maddie. I could have been a loving
partner. You'll eventually understand what love is but try and be alone
for some time and find out why you are you."
Her five cases were in the hall and she was dressed in a great A-line
with sheer hose and 100mm black slingbacks, her auburn hair partial up.
She had helped me become expert with my own makeup and now as I looked
into her light hazel eyes and cried, of course sad for her leaving but
more because I realized she was correct. I loved dressing her and
settling how we'd look together just as she loved making my face.
Though she seemed to be on the same wave she needed to be herself. Not
Lisa for me. I was going to miss her beautiful cock though. Sure she
passed without question, unless you found her in only a panty; it
straining to keep her 15cm flesh down between her perfectly shaped
thighs.
"You will find love Maddie just resist hooking a girl for a couple of
months and settle what and how you'll be happy. Then the perfect mate
will fall into your lap dear because you are a great lover and unique in
your interests."
I didn't go out for three weeks after Lisa fled though I did invited
several old friends in for dinner and sex. Each gave me a similar view
on my lover's query. Could I settle down and help someone just be
herself? In the past I'd needed the joy of the new to keep me alert and
sated. They each felt my needs were primary to theirs in the
relationship hence the split. Clearly my emotional maturity was at the
core of the issue. I had some work to do if I was truly to find love but
did I really want this? Maybe the rotation of beauty was part of my
need? I decided to stay single for at least six months and gathered my
various toys as a substitute and reduce my wandering. I visited only one
gay venue during this period, tending to meet others and friends at
traditional bars. I discovered more than a few girls that were
attractive but though we flirted I resisted the temptation for an
overnight. Some months into the forced behavior change I noted more
preferences, which type of woman I did need.
I also discovered that hanging with a woman in a traditional bar lead to
other issues unfolding even if society allowed gay women a place. I was
surprised at the second attempts made while sitting enjoying time with
another woman. Men would press their 'advantages' and women could be
crazy. On two occasions the risqu? behavior of women who wanted the
attention lead to or caused a short hen fight. It seems that to closeted
lesbians seeing two sexy women close at a bar is a signal.
After this period I needed to re-explore and I'd found a new club. I was
invited to a small gathering on a Thursday evening just after six. I'd
skipped the last work hour to properly prepare for the evening. A new
LBD was set out, as were my other furnishings before I started work that
morning. I had a salon visit at lunch and after work stopped home to
shower and dress for the evening. I paused in front of the tall mirror
in my dressing room; my 31 year old body still had lift, the breasts a
nice but modest size, my butt taut and without a bit of cellulite. The
dirty blonde hair fell softly to the middle of my slim back. Not quite
an athlete's body but close. I dressed in the lingerie as I considered
the new mindset. Stepping into the dress with cap sleeves and an open V
collar I reached to the zip. The hem fell to just above my knee and I
slipped on sexy slingbacks. Checking my face I felt Lisa's training
really helped with my makeup. I grabbed my evening bag and ran to the
elevator for my taxi was waiting.
The taxi pulled to the curb of a 19th century factory building. A small
deep grey plaque with white script letters just beside the door the was
the only identification: Hers.
I didn't ring due to the sound of a lock release and noticed the
security camera overhead. Leaving the large elevator, manned by a
serious hunk, I stepped toward the jazz music coming through the heavy
steel fire door. Again a big male was stationed and took my simple wrap.
Everywhere there were beautiful women dressed to kill and smiling. The
setting sun was streaming through the industrial windows at the sharp
angle of early spring. This felt like a great new start. A hostess in a
simple black maid's uniform approached me carrying a tray with flutes of
champagne.
"Welcome Ms. Quill, the staff is happy you've joined the Faunesse. Enjoy
and let us know how we can make your evening special." I smiled and
watched as this beautiful young woman moved passed, her sexy bum moving
beneath the simple fabric. I watched a moment longer then moved toward
the glazed wall where several others were gathered looking over the
City.
"Hello, and welcome, you must be our new member." I turned to my left
toward the soft voice and looked at another beauty and saw immediately
her secret, so subtle and yet I knew having been with many transfemme.
"And you are?" I said.
"I'm Juli, one of the original members. We are so happy to have you with
us. Can I show you around and introduce to some of the others?"
We moved about the space, meeting members and a few guests for over an
hour. I asked for the restroom. I passed a darken hall on the opposite
wall from where Juli had directed me. She had indicated there were
several private rooms on this floor, with full suites on the floor
above. Exiting the washroom I was bumped by a woman preoccupied as she
turned into the main hall.
"I'm so sorry, I'm a bit blind after that." She nodded over her shoulder
as if I'd understand.
I was dressed appropriately as the others had clearly prepared as well;
many LBD's and sexy legs were present. As the evening became darker food
and salads were presented, and the drinks continued. I met over forty
women, at least two to which I was very interested in getting to know.
Not to say I couldn't have enjoyed the company of each person I met. I
simply had a different perspective. Juli was a bit older than most of
the women, but she was still stunning, but I was looking for someone
nearer my age. I had decided to head home when I passed a table with
three women. One of them shot me a stare and stood as I walked near.
"Leaving before we've had a proper introduction?" I paused and turned
toward the table.
"I'm Tess, but I'm not a lost milkmaid. Can you stay for awhile longer?"
I liked her immediately and when she was by my side she reaching out for
my hand, but took me by the waist instead and she kissed my open hand.
"I'd liked to stay and get to know you Tess, and your friends." But when
I turned back toward the table the two others were moving off in the
other direction. "But I've got to go. Maybe I'll see you next week
okay?" She smiled and slowly released my waist.
"I'll be waiting, you're worth it and I'm sure of our next liaison.
Until then, hold this for me." As I'd turned she handed me a small stone
object that I couldn't understand. "Slip it into yourself to remember
our first meeting."
I dropped the gift into my bag without thinking or looking at it. The
doorman had hailed a cab and I stepped in and car moved away. I looked
out the window for Tess was at the curb. While riding I removed the
object from my bag. It was about 7cm long, slightly flared, than I
realized it was a discreet anal plug. I smiled thinking of how forward
this woman was. Certainly we would see each other again.
The next week of work really pushed me and I was happy when the HERS
alert text arrived on Thursday morning. I cleared my late afternoon
schedule to allow some time to prepare. As I entered the dressing I
glimpsed the plug Tess had given me on the jewelry box. I'd forgotten
about it all week. An extra cleansing was required now so I stopped
dawdling and got started. Once my bum was clean I reached for the
strapless blush bra first and settled in and hooked it into place behind
my back. I had selected a panty but put it aside for the narrow blush
thong and started to gather my pantyhose. I thought again and went to my
hose' drawer for a unique non-lycra nude pair with a red welt and seam.
I knew exactly whom I was hunting after all these years. With the
suspender in place I balled the hose' and ran them up my long legs. One
of my earlier girlfriends had purchased for me a collection of the
traditional but beautiful suspenders; six clasps with a tight waist. The
heels would be important as well; too low and I'd have the butches
chasing me, too high and I would be restricted to less movement. The
black open toe 110mm pair would be perfect with a very low quarter. I'd
selected a different LBD, slipped on my jewelry and I was ready and off.
This week the party seemed a bit more crowded and another senior member
introduced herself. Georgia was about my age, slim but slight at 168cm.
We were walking into the Bar when Tess approached smiling.
"You two know each other it seems," said Georgia. "I'll be off to help
the other newbies."
Tess moved nearer, "You look just fabulous and I hope it's snug in your
bum." meaning the plug. I considered what I might say as a retort but
instead took her left hand and brought it to my smooth backside. She
immediately traced my spine to confirm her question. "Very lovely, I
mean your butt. I'd hope you'd come prepared tonight."
"I'm always ready for some fun Tess but I worn your toy as a sign of my
quiet respect. We'll have to go slow if you want to have me to keep. I'm
emotionally soft right now and need patience. Where are your beautiful
girlfriends?"
"We'll catch up with Alexa and Emma later. Can I bring you something?" I
looked into her eyes and saw that Tess was someone special, deep within
her eyes there was spirit.
We moved to a small couch, settled and she slid her heels beneath her
bum. Now we had some time to learn of each other. I discussed a little
of my history, asked about the Club, it's name and why 'HERS' was
important.
"Rodin created a bronze called Faunesse and Juli offered the name at an
early meeting. I joined in the second year." She told me that nearly
sixty percent of the women were serious lesbians while the remaining
were all over the spectrum.
"As you noted Juli is the prima transfemme and there are nine others.
Oh, and though it may appear as if there is a dress code I assure there
are no such rules. I adore your outfit Madeline."
She suggested we complete the tour Juli had interrupted last week so
wine in hand we entered the hall.
"The private rooms are simple, a day bed and cabinet, a corner sink.
Nothing crazy tends to happen in these, but a lot of kissing and
petting."
She moved in closed and I allowed the kiss, she clearly pressing her
lead, tongue across my mouth, while her hand reached up my hem and
touched the plug. "You're moist for me. I like that in a lover."
"Please take it slow with me Tess. I want to get to know you as a friend
before you're my lover okay?" Her fingers lingered at my thong panel a
moment longer, and her long fingers spun the plug before retreating down
along my leg, passed the stocking welt.
"It will be difficult but I will await your sign next time." I had
enjoyed her touch and wearing the plug was a bit flirty.
We returned to the main foyer at the foot of the generous open stair
with a skylight "Upstairs are the more private spaces."
Once at the upper level she pointed to a Foyer with six adjoining
doorways, four of the doors closed and a subtle red light shone. "Those
are taken. You can reserve them a week ahead."
Turning to the other doors, "These two suites are available as
necessary." The doors were open and she moved to the suite on the right.
"This is an extraordinary room, what a view, and the finishes." I moved
toward the bathe.
Tess followed me speaking, "Each suite is unique and very comfortable,
one could stay here without a bother for two or three days." She moved
to sit near the window. "Granted that only happens occasionally."
I sat across from Tess and being close again I paused to take in her
outfit, details and study her manner. Now I was certain, though there
was no true 'tell'. I just knew she and I would fit. I stood when I
noted the bar, "Care for another drink Tess?"
"You're not a typical lesbian, but you of course know that. But if we
start you must be prepared for a storm. I will fill you like a wind and
push and pull you into my dance. Can you see yourself releasing for me,
humm?"
I turned back toward her, smiled and just looked into her eyes, but I
said, "Let's meet sometime over the next week Tess. I need to pause my
racing heart and consider you clearly. Can you allow me that dear
woman?"
I'd walked to door, stopped again, looked over my right shoulder to her.
She was still seated. I turned and looked up to the skylight at the deep
coming night sky.
"Somehow I'll quell the fire you've started in my panties until then.
Your plug can remain with me I assume?"
I heard the sound of her heels as she approached. Now she was beside me
and she reached for me and we turned to kiss gently. Her tongue again
slowly exploring me while her hands move across my bottom. I enjoyed
being loved by this beauty. Her ripe body might soon be mine to please.
I had to resist Tess so I moved slightly breaking our kiss, smiled and
moved to the stair and left the gathering.
While seated on the sofa at the apartment I realized I'd forgotten the
plug. I went to the bathe to remove it. Later that night I had a chance
to review the clubs members only Website, looking into the background of
several of the people I'd met. I wished to understand more about club.
Juli was listed as the most generous donor to the club. I found on the
google she'd made a killing in distressed property in the southwest
prior to 2008 and was very comfortably. She was originally from San
Francisco and wasn't married now. Her bio stated she'd transitioned at
twenty-four years old. The other fifty women had varied descriptions of
their sexuality.
Tess's information was less specific. She had been born in New York and
was twenty-nine years old. Her gender wasn't noted but I was pretty
certain that she'd transitioned. Her education listed University of
Chicago with a degree in Art History, and another in Computer Software.
Somehow she had found wealth of the necessary scale as a dealer for art
photographers but she also worked at a regular job. The picture attached
to her bio only furthered my interest. Her blonde hair fell to below her
shoulders but with blunt bangs. She listed her height at 175cm and
weight at 55kg. In the photo her blue eyes were intense, more so than in
person so I assumed she sometimes wore tinted contacts.
My past relationships weren't as sexually driven as it might seem. I
enjoyed my liaisons and affairs but most of the girls who had moved in
were in need of very specific care. I insisted on strong penetrative sex
and mostly resisted providing them the opposite. Since Lisa had moved
out I'd focused on learning to appreciate how to treat a lover's needs
as my own. Last month I'd spent the holiday weekend fucking a sexy older
woman I'd met at a party. During the long weekend she had shown me the
beauty of penetrative anal sex. Prior to her request to fuck my bum I
had only allowed my lovers to lick me there. All of the girls had wanted
me to fuck them with a strap-on and I did sometimes. But I failed to
orgasm during these sessions while bringing them off and therefore I
didn't offer this unless requested. Never had I consented to having my
tight passage entered.
The weekend with Mary I had reached orgasm as I'd fucked her butt but I
had multiple orgasms when she deeply loved my ass. This was a new
adventure and required careful cleansing. I had decided to work at it
and tried with my toys with success and learned the technique. Patience
was important. If I had further explored this act and my body with Lisa
or better with Jenna, the brunette beauty I'd lived with for 15 months
over two years ago, I might be a married woman now.
I was at the doctor when I received a cell call from an unknown number.
"This is Tess. Can you meet me for a drink this evening?"
Tonight I was busy with a client and couldn't meet, but agreed to do so
the following evening. This began a slow seduction but not by me; Tess
was after me.
Our drink turned into a light dinner but I passed off her flirting,
"We'll see each other soon enough dear."
She kept at me. Flowers arrived at the office the next morning and the
following afternoon there was a box delivered. Inside were a lingerie
outfit, quite beautiful, and a note with a poem.
She said please
she said she feels
so a young woman
like one
with desire
for a union
she must flirt
must tease and warm
with fingers
and other members to compare
The poem was just the beginning for she left a phone message, then a
sextext of her bum. Clearly we had a need to get together. I responded
to only the sextext, with a smile and an address; she had to pick me up.
I was trying to take this slow. To focus on the details I'd previously
missed in my relationships so I agreed only to meet for drinks and
dinner.
She'd found a lovely place with a mixed crowd and we weren't the only
gay couple. I was dressed to attract her eye and imagination. I selected
the pale white lingerie she'd sent me including a very delicate waist
suspender. These were fine garments and I wanted to play the part of a
submissive lesbian femme. My legs were in sheer nylon hose' with nude
colored 110mm heels. She knew what I had on beneath the ivory skirt and
white sheer blouse with a scoop neck but I worn a chemise to subtly
conceal my body and the soft lingerie.
"You're taunting me but your manner of flirting is very discreet. I'd
like to take you to bed this night. To slowly remove lovingly those
garments and play over your body with my tongue, then slip inside you."
She was trembling with excitement yet I played mute, waiting rather than
giving her any sign. Beneath the table she'd slipped her right heel off
and stroked my legs with her hose' covered foot but I simply sipped the
wine and commented on the vintage.
"When I allow you to my home you can bring this along. It's a great
Pinot. I'd love that Tess."
Then I was silent as she continued to speak of her attraction, the
massage beneath the table dressing continued. I changed the path of the
discussion, asking her to tell me of her first encounter. The story went
on nearly an hour. Not about a girl and her but of a slightly older
woman. Divorced but with a young child whom Tess help care for. Cathy
was instrumental when Tess was fifteen finding and buying her the
hormones that started the changes Tess desired. She also helped train
Tess about beauty care and makeup. Tess had worn her hair quite long but
it was a mess and Cathy brought her to a salon that helped repair and
shape her hair while still easily converted with a band to a boy's
style.
Their relationship became sexual when Cathy deemed Tess could pass and
only if they were both properly dressed, lingerie as well as dresses.
Their loving didn't include any penetration for over eighteen months.
Tess finally convinced Cathy to use a strap-on in bed one afternoon
while the child napped.
Tess continued, "Soon after that Cathy stopped calling for me to help
with the babysitting and within a month she made it clear our
relationship had been spoiled by the act of penetrating my bottom." I
saw her eyes moisten but no tears fell.
"Anyway I was off to Chicago very soon after and classes distracted my
memories. Why I can still feel this pain I don't know. Cathy was of
course a beautiful and a tender lover. I clearly needed more though and
the split was therefore a good thing."
I sat quietly listening and she suggested we head to her apartment.
"Tess I want you as well but I want us to settle a good foundation
without sex, if that's alright with you. I feel it will be for the best
dear." I reached across the table for her right hand, a diamond on the
fourth digit.
"That a beautiful stone, a gift?"
"I had a serious male admirer for nearly a year. His true gift was his
great cock but he tried to marry me as well. I just knew it wouldn't
work. I wanted his sister more than him," she laughed.
So we shared a cab home. She watched me enter the building. Than the cab
moved back into traffic.
Again the next morning flowers arrived and another box and a poem. This
time the gift was a realdoe insertable! I smiled knowing I would use it
with Tess soon.
"Stop sending me these toys to my office Tess. The distraction isn't
helping me do my work!"
She asked me for another date, Friday evening, at a surprise location.
Reluctantly I agreed so long as she didn't assume we'd be in bed that
night.
She chuckled. "I promise not Friday."
I decided that evening to research the difficulty transfemmes encounter
in the job market and business. Tess had an advanced degree in computer
software and worked in the IT department of a small international firm.
That appeared to be one of the few great jobs and the firm was on the
record as supportive of the LGBT community. Her sole art venture was due
to meeting several artists at the end of her college studies. Two of
these had become big and Tess enjoyed the fruits of their success.
She would eventually find out about all of my passed lovers as well as
my financial background. We could be every good for each other so long
as I didn't mess it up. I thought of Jenna. How I'd loved her breasts
(the best boob job any woman could get), and she had a great cock too.
I'd allowed her to simply leave and now I thought to call.
"I know you asked me not to call, but I just had to find out if you're
okay?"
She didn't speak for a moment. "I'm with someone right now but he's in
the bath. Email or a text is more discreet girl, you know that."
She paused. "But I'm just fine. No long term relationship but I'm cool
with that. I'm staying healthy and sane, and you?"
I shared the recent past and we agreed to speak in a couple of months.
It was clear she was sleeping around. I guy? She'd not been with a guy
in years as far as I knew.
Friday evening Tess arrived by cab and had told the driver to wait. She
came into the Lobby and asked for me.
Via the phone I said, "You're twenty minutes early! But it's fine Tess.
I'll be ready in a few minutes. Come upstairs while I finish."
She entered the unlocked apartment a minute later and I called for her
to sit and enjoy a glass of Chardonnay I'd set for her. I entered the
Living Room ten minutes later ready to leave to find her looking over my
photos and Library collection.
"This one of you is beautiful but who's the girl?" Her question
distracted my attention. I was reviewing her flouncy tiered, cream-
colored dress.
I moved to her side; in my heels she was just a bit shorter, "That one
is Jenna but let's not go there right now."
She turned quickly and kissed me, her tongue finding mine and playing. I
noted how quickly my pussy became moist as she felt my breasts.
"Slow down honey," I said pausing but not ending the kiss. "I love you
in this color," I whispered in her ear.
Tess said, "We've got a few minutes," her hand running down my back and
started to lift my hem.
"No we don't young Lady! Let's go before there's an accident. My panties
are just a bit wet and not soaked yet."
In the elevator she drew me to her and I felt our breasts touching, hers
were just a bit larger. Her nipples erect and noticeable through the
fabrics of her spring outfit.
"Tess, please stop for now I am quite moist. That's what you were trying
for, so yes my pussy wants you. The toy you sent me hasn't left my mind.
It's quite stout you know."
She smiled and took my hand and caressed along the front of her
beautiful dress. Up until this moment I'd had a wonder about what I felt
but wasn't certain.
"You tuck very well. Or your clitty is quite small Tess." she smacked my
hand and kissed me roughly.
"You can't wait to see my clit can you? You've been lusting after me,
huh? Well I'm a bit more stout but also very soft, and very attracted to
you Madeline and can't wait to fuck you!"
Her hand reached the welt of my stocking. "You had better always dress
just so for me dear. I will for you too."
We kissed just as the doors opened and my middle-aged neighbor Ms.
Lester looked up and frowned. She of course knew of my girlfriends but
she didn't like the public display she'd just witnessed.
Dinner was great. The wine perfect and we didn't finish until nearly
ten-thirty. Leaving the restaurant our heels clicking on the bluestone
slabs I asked, "Shall we have a night cap at the Bar down the street?"
Tess looked pensive.
"I'm not going to sleep with you this night. I told you earlier this
week we need to go slowly Tess. I think you're too special to lose and
want our first time to be just perfect."
She turned upon her heels, a beautiful and tall pair strapped about her
lower leg well above the ankle.
"Okay. Then let's stop but at a wine bar nearby instead."
They had a wonderful cellar and Tess clearly knew what to order. The
Gamay arrived and was perfect. I failed to read the label until a bit
later, Point-G 2006. The sly smile on her face made me realize Tess had
a plan and I was the target or the prey. We were seated in a little sofa
wrapped about a caf? table. I had slipped off my heels and slid my feet
to the edge while Tess massaged my hose' covered legs. She spoke softly,
cooing her words. As midnight approached I softly asked Tess to get me a
cab home.
"Won't you let me bring you to my home?" We were reclining on a sofa and
I moved to look down at her.
"You started this evening making my panties wet Tess and I assure you I
want to return with you but I was very clear."
I stood and slipped on my heels turning to leave. She jumped up and
tried to hold me, "NO Tess, not this night. Soon yes, but not tonight."
I continued to the door, she slightly behind trying to get her own shoes
on. As I reached the door a cab was just pulling up and I had my wrap
and signaled to the doorman.
"When can I see you again?" she pleaded.
"We'll speak early next week Tess."
I turned and gave her a quick kiss then entered the open door of the
cab. I was upset and also aware I was being a bit of a tease.
I was so hot for Tess but I had settled my path. The relationship was
more important than the sex, at least right now. I thought of our
evening, of her touch and the kisses. I hadn't checked my messages in
more than thirty-six hours and on the ride home found that Jenna had
tried to reach me. The message said:
"Call ANY time"
I paused to consider the possible benefits of pursuing Tess while re-
visiting with Jenna. It could be interesting to better understand what I
had lost over thirty months ago. I quickly placed the call even though
it was after midnight. Jenna picked up on the second ring.
"I'm glad you've call. Where are you?" she asked.
"Please come see me right this moment, please?" I considered how aroused
Tess had made me and re-directed the cab to Jenna's new address.
I arrived and was buzzed passed the entry; she was waiting for me. The
mirrored metal elevator door allowed me to collect myself, straighten my
outfit and run a brush through my hair. Jenna met the elevator and
jumped to kiss me.
"Come to me you sexy Lady". We entered her apartment hand in hand and
she led me to the sofa near the windows. We hadn't seen each other in so
long yet she knew what she wanted and I think she understood from my
questions last week where to take me.
"I still love you and miss you Maddie but can you be with me?"
She paused in her excitement to settle into a reclined position that
allowed her gown to fall open. Her lovely breasts were just held by the
thin material which fell to her open thighs, just covering the tip of
her semi-hard clit. I considered her beauty and shifted closer. She'd
clearly showered and re-done her face.
"Yes Jenna, I need you tonight as well, but I've changed in important
ways since we last were together." She smiled knowingly. Previously our
lovemaking would include kissing, petting and lead to her entering me
after I played with her clit. I would occasionally penetrate her. She
simply looked over to the side table. I followed her eyes and saw the
fleshy strap-on, proud and erect.
"Is that what you mean by 'changed' sexy Lady?" She moved and kissed me,
while reaching for my skirt zip. "Is that the way we'll play tonight?"
The phallus was extraordinarily large.
She started to un-button my blouse. "Can you handle fucking me, humm?"
She caressed my breasts while releasing the bra. I felt so alive and my
pussy was so wet. Her hand came to my mound.
"Why are your panties so wet sexy Maddie? Missing me a little or has
someone else got you humming?"
I was quiet, allowing her to slip off the damp thong and remove my
chemise and bra, as she reached for the strap-on with her other hand.
"Let me settle this for you." The harness was a flesh colored material
and concealed a small protrusion. "Don't worry, we're both going to come
tonight, maybe at the same moment humm?"
I considered what I wanted to do, to fuck her like she enjoyed, allowing
her to do my ass as well? She had wanted my tight opening for so long.
My right hand reached for the large phallus as Jenna cinched the strap
tight and my mound felt the subtle vibration begin.
"Turn to me sexy Lady, I want to see your cock." I held the phallus and
nodded to Jenna. She moved close and dropped to allow my phallus to
enter her mouth. Moaning softly I watched as she ran her tongue along
the length, across the tip and deep into her throat.
She removed the phallus slowly, "I've been sucking a bit more real cock
as of late, but I need to be fucked. Can you fuck my mouth please?" I
trained my attention on the willing soft mouth and slowly began to move
into her while holding her shoulder.
"Watch the teeth Jenna, and hold my balls gently. Kiss the tip girl,
yes, run your tongue around the smooth head Jenna. I'll let you in on a
secret, I've missed your beautiful tits and your great clit too."
I pushed her to lay back and this exposed her tight opening. Her thong
now concealed her stiffness so I pushed the panel away from her pink
rosebud. I ran the moistened cock up and down her perineum, teasing her
while my fingers entered her mouth.
"Suck on these while we get you lubed."
"I won't need any dear. I'm so ready for your cock. Please enter me." So
I slowly centered the stiffness and pressed up and into her, pausing
with just the large helmet inside.
"That sooo good sexy Lady, yes go slow, I want to feel each centimeter
enter my body dear. Ooh that's just perfect, now all the way in please.
Oohh yes, all of your cock sexy Lady, press your nuts into my butt!" I
leaned forward to kiss Jenna, holding her chin with my right hand, at
the same moment I withdrew the phallus some 5cm, then slid back in
deeply.
"Oh Lady that's what I need. I need your cock, fuck me now, yes. Sexy
Maddie, fuck me!" I started at a pace fucking her slowly but deeply and
kept my face close to hers and kissing her. Her mouth, her cheek, her
ears, while caressing her breast with my free hand. We were looking into
each other's eyes,
"You still love me, after I hurt you?" I said.
"Sexy Lady you're inside me and my peak is near, yes I do. I do love
you. I love your cock inside me. I only wish it could shoot me full of
your seed. Keep fucking me!"
She closed her eyes. I had noticed the stir within my pussy though not
penetrated. The vibration began to cause my pussy to contract and I was
going to come. With Jenna's tight body wrapped about the smooth phallus.
We had never experienced a mutual orgasm like this before. I increased
the pace and the stimulation at my mound moved just to the right and I
started to come and she was gripping my body. Holding me close as the
deep fucking brought her own release. She loudly orgasmed as the phallus
pounded her tight bottom.
Afterward we lay relaxing in each other's arms in the bedroom, with a
cool white wine.
"Will you let me fuck both of your openings this night Lady?"
I turned to look at her face. "Don't be greedy Jenna, but yes. Maybe
after a rest, near morning we'll make love again okay? Why the urgent
call tonight? Were you alone or just horny?"
She started a story about her past month, with first a man, then a
woman, confusion on her part, but some great sex. The woman wanted her
to move in with her and her husband but Jenna worried it might get too
kinky. She just needed some time with a friend. My call last week had
opened the door so she'd reach for me. I was happy she had called for
the release was what I needed.
"So you decided to find out how sexy your butt is Lady? I've always
loved your little hole. Now you'll let me in, humm?"
I decided to be as truthful as possible. "I met someone who insisted I
allow her in, over thirty-six hours she fucked me repeatedly and I came
so strongly Jenna. I realize you'd tried to get me comfortable with anal
for so long. I resisted foolishly I now see."
Jenna smiled wickedly. "Turn over. I want to kiss your ass Lady," she
rolled me a bit onto my side and dove beneath the covers, licking me
with intent, then slipped her middle finger into me.
"You are accessible Lady!" She played there, licking, stroking and
rimming me for ten minutes.
Jenna was calm as she lifted my bum and positioned a pillow. She stroked
my back, and ran her hands under to grasp my breasts, thumbing my
nipples gently. She moistened my cleft with a lube and then played her
clit along my slit and then my anus. Without a word she pressed the tip
of her cock inside. I was caught surprised. It was so thick but the
penetration wasn't uncomfortable. She subtly eased a bit in, then a bit
more and stopped.
She again grasped my tits. "You are ready Lady. Never before have you
allowed me inside your bum. Can you sense my excitement? My clit wants
to come inside Lady, may we enjoy this first and special loving."
Though fully penetrated by her clit this was the first warm cock I'd
allowed in my bottom. She was smiling and looked so beautiful. Now I saw
it as something to enjoy in a new way.
"Oh Jenna, make love to my ass please? Slowly, but do fuck me please
Jenna."
I reached around and used my right hand to hold her close to my back.
"Pooch, you're so deep within me Lover. Stay with me Jenna, stay, fuck
me, fuck oohhh." I came again but she didn't pause, just continued to
fuck me. She moved off my back and we coupled in a reverse cowgirl and
fucked until her peak. I'd never felt a seed eruption inside my bum.
We stayed close and quiet until she slipped out but she quickly moved to
enjoy her seed seeping from my opening. Her tongue soothed my rear until
she felt she had retrieved most of the juice. Her lips met mine and she
pushed some of the juice into my mouth.
"Maybe you'll stay the weekend?"
- - - - - - - - - -
Tess had not been happy I'd left her Friday near midnight. Her own
history was surely filled with past lovers but she was falling in love
and therefore used the quiet time to consider the next phase of her
seduction. She wanted something to come from our meeting and felt she
was ready to commit to one woman. It wasn't strange to Tess that we were
attracted to each other. She had the advantage most transfemme never
have, having transitioned near fifteen. Her skin and hair were as
perfect as any twenty-nine year old genetic girl and her breasts had
large areolas, unusual for a transfemme. Since she was seventeen Tess
had never been mistaken for a boy. This had caused the separation of her
parents though once Tess moved away to college her parents had resolved
their issues.
She didn't see herself as anything other than a woman and treated her
penis as just a normal part of her world. She had come to Canada to
pursue a business opportunity and found the society and the
relationships so supportive she shifted her entire portfolio and bought
the loft about two years earlier. In this town the lesbians were treated
with respect not derision. Because her look was so passable she had
always been treated as a lesbian not a transfemme.
She awoke early the next morning to prepare. She had decided to focus
all of her energies on me, loving me, making me a part of her life. By
eight she had settled her plan and was outside my flat by nine-thirty
awaiting my first morning activity. Only I wasn't at home and had turned
my cellphone off. She realized something was not in order around eleven
but she had no alternative. Eventually she entered the Lobby and asked
the Doorman if he could ring the apartment. With no answer she could
only wait, but she also started to worry.
- - - - - - - - -
Saturday morning I'd awoken before Jenna and easily made myself at home.
I heard the shower just after Noon and brought her some coffee. I
watched as she readied herself.
"What is your plan for today?" she asked.
I just smiled, unsure I wanted to do anything except stay here with her.
"Is there anything you need to do Jenna? I haven't decided to do
anything though we could go downtown. There is a gallery opening I could
stop by around five but it's not required."
She had partially dried her hair and was applying makeup while dressed
in her fluffy robe. "I have to take you somewhere special. Can you be
ready in forty minutes?"
My evening clothes wouldn't do. "Can I wear something of yours?"
We were dressed for a party and in a cab. "Where are you so intent on
taking me?"
Jenna was beautiful in a black mesh over blush dress, nude hose and
black 110mm slingback heels.
"You'll enjoy this event Maddie. A small fashion show in Oldtown at the
Spice Gallery."
The Spice was an old wood frame warehouse near the waterfront used for
various special events. I had a curious relationship to fashion design.
I'd spent time while at college walking the catwalk for extra money.
"So you gladly loan me the star of your wardrobe," a Dior seersucker
knee length dress, "to show me off, humm?"
She smiled and pulled my hand to her, to the folds between her thighs,
"this is the only thing I want to show you dear."
I blushed as she parted them allowing my hand to reach the naked skin
above her hose welt.
"Press into me sexy Lady again tonight?" I thought about the offer and
turned to kiss her, my tongue playing with hers.
"Then let's turn this cab around. I'm hungry for you too." But we had
arrived at Spice.
The driver jumped out, I guessed he wanted to enjoy our exiting the
tight backseat, our legs and heels on display.
Once seated in the third row I looked about to see whom I might
recognize or know. Several of the women I'd met at Faunesse were near
and I noted that Mary, the lesbian who opened my back door, was off to
the right near the stage. Thankfully Jenna disliked overt public
affection. Even holding hands annoyed her. I wasn't too concerned about
word getting back to Tess. She wasn't my girlfriend as of yet just a
friend. I waved to several women and then the show started.
After the first break I saw Tess. She was near the rear, standing and
hadn't seen me yet. I recalled that she had commented on the photo of
Jenna and me so she might recognize her. Considering my options the show
began again. I was distracted thinking of the two women in my life. I
barely noticed the parade of beauty, the dresses and outfits, the shiny
thin models.
When the show finished I looked in the direction where Tess was previous
but she was gone. I was surprised that I was worried. Being with Jenna
again felt so right until now. I didn't want to hurt Tess but now I
realized I just may have. I decided to not ruin the afternoon and asked
Jenna to leave; to return to her apartment. We made our way to the
street and found a cab and I didn't see or encounter Tess.
"What caused you to become flustered?" I turned and looked at my lover.
"It's of no matter Jenna. Just hold me tight and love me again okay?"
I returned to my apartment late Sunday afternoon. My body was tired and
my bottom sore from Jenna's fucking. She used all three of my opening
several times. Her seed filled me. Even now I wore a panty liner to
prevent it leaking to soil my dress from Friday evening. I didn't look
that worn since I'd showered and settled my hair but I felt I needed to
good night's sleep. I was removing my clothes when the bell rung but
there hadn't been an announcement. Sunday the Lobby door wasn't manned
after five. I went to the door but stopped to grab my robe. I was in
only my bra and thong. Opening the door I found a crying Tess. Her
mascara was running and her face smeared.
"Why did you run off with that girl? She had her time, now I want you,
need you!" she fell into the Foyer and I stooped to catch her but ended
atop of her. Tangled by the robe's long belt.
"Oh Tess, I didn't try to hurt you it just happen. You and I will be
together. I need you too my dear. Let me help you."
I moved to my knees and wiped her face, the tears still coming. "You
poor girl, let me get you to the chair.
"I'll get you a drink." But she stopped me by grabbing my left hand.
"No stay right here. You do owe me an explanation Madeline. Then I'll
decide whether you're still worth all of my attention."
I explained how I'd come to spend the weekend with Jenna. How I did see
her at Spice and how I felt about the two of them. She listened and
continued to cry,
"So you do still love her? Still want her?"
"No Tess, it's not as simple as that. Jenna and I had something very
special and she will always be my friend. You and I are starting a
journey to find our love. To fill both of our lives with each other.
There will be plenty of time for friends, especially those in need."
She stopped me. "You did let her fuck you? Let her release inside of
your pussy? The other opening, the one I wanted to be just for me? Did
you let her fuck your ass?"
I paused to let her complete her rant. Let her exhaust her negative
feelings toward Jenna.
"First Tess, we are still NOT lovers."
I moved away but still on the floor.
"I want you to be so but I need it to develop rather than just a rush to
fuck. Second, no one owns me nor my body and especially not my tight
little ass. Is that clear young lady?"
I was upset that she felt she could control me.
"You need to back off and focus on what I thought we both wanted."
I stood and stepped toward the glass wall. I looked to the City but
could see her in the reflection as the sun had fallen.
"You can have a simple dinner with me here or you can get out and find
out what happened to the girl I was starting to love."
She stood and retrieved her bag, wiped her nose, pausing again. She
seemed to be thinking. Then she sat down looking at me then out toward
the view. She stayed there without speaking for several minutes.
I went to the bar and poured two glasses of wine. As I moved back toward
her I saw her looked down at the floor.
"I don't want to eat anything nor do I want to go. I'm here because I
love you Madeline. I have been outside most of the weekend awaiting your
return. I'm sorry to crash your Sunday evening. Maybe you can give me
that glass of wine?"
I walked a step and extended the glass.
She looked at me and said, "I'll settle down and consider what you've
said. Can I use your bathe? I need to clean myself up a bit." I directed
her to the Guest suite but was surprised when I heard the shower.
I tapped on the door. "Tess, I appreciate what has happen but you cannot
spend the night."
She called out her awareness of the time, "I just needed a quick wash.
I'll be out and presentable in a few minutes. Can you bring my bag
though?" I did so and resisted the temptation to peek inside. It was a
small black bag, the one she'd had with her Friday evening.
I turned from my chair near the window when she entered.
"I feel so much better. Can I sit with you?" I motioned for her to sit
across and she noticed the re-filled glass. "Please forgive my earlier
fit."
I smiled. "You look much more presentable Tess and let's just enjoy the
evening. Sure I can't interest you in a portion of my small supper? Its
very good Sushi from Kazi."
I went to the Kitchen to gather the plates and sauce. She had calmed
down but wasn't herself yet.
"You're typically so talkative. Let's just relax for awhile?"
She stayed until after 8pm and I was happy to see her forget how the
evening had begun. I told her I would call her late Monday evening and
we arranged to meet at Faunesse on Thursday.
I kissed her gently at the door just as the elevator arrived. With the
doors closed I returned to clear the dishes and glassware. I consider
whether this evening had any impact on my feelings but decided to forget
the negative. The weekend with Jenna was fun but something soft in Tess
was pulling me to her. Though Jenna was special I was bother by her
activities with her gentlemen friends. I couldn't imagine she was
soliciting but what if she was? She hadn't spoke about these encounters
while we'd spent the weekend fucking.
I received a text from Tess Monday afternoon. She had to travel to
Quebec for a meeting Tuesday so we'd see each other at the Club.
I was conflicted; Jenna had asked me to meet Tuesday for a light dinner
but I said I was over booked at the office. I truly need time away to
consider the next step, either with Tess or Jenna.
When I got home Wednesday there was a gift package from Tess. The note
was from a Quebec lingerie store. Inside was a set of dark undergarments
from the Graphique label including an elaborate suspender and full
fashion black hose. Her poem was short; 'longing to see and feel you'.
I knew what I had to do Thursday. I called my salon for an afternoon
appointment and selected the dress for the evening. I wanted it short
enough that all who saw me would want to seduce me but especially Tess.
Getting away from the office proved to be difficult and I had to shift
my appointment. The afternoon would be more hectic than I liked.
I finished my face and settled to dressing. Tess's plug was on the
dresser and since I was clean I moistened it with my tongue and slipped
it in place. The feeling was distracting. I removed the sexy hose' and
the suspender from the beautiful box. This one had eight clasps and was
embellished with macram? embroidery and a cute satin bow about the back-
panel concealing the fasteners. The black hose' were surprising; they
appeared custom fit to my leg length. I slipped the brazilian panty up
and over. My dress was quite sheer allowing a subtle reveal of the
undergarments. The chemise added a layer of concealment but I felt so
sexy dressed and filled. The plug in my bum reminded me that tonight I
was Tess's.
I arrived a bit late. Most of the women were on hand therefore I didn't
immediately see Tess. While looking about a slightly older dame
approached me.
"I'd love to be what you're looking for. I'm Suzanne."
We spoke while I moved to the queue at the bar, still my eyes wandering
across the crowd. I was surprised when Tess came quietly from behind me
to hold my waist.
"You're incredibly beautiful dear. Have this rather than waiting for the
barkeep." I turned to her smiling face and kissed her deeply.
Taking the glass of white wine I said, "I've missed you as well Tess."
Suzanne just shrug, "I'll be dreaming of you tonight dear Lady. Touche'
to your conquest Tess!" and she move on.
After the party finished I agreed to accompany Tess to her flat. Upon
arrival I was surprised by the large loft yet the rough space was
elegantly furnished. We settled on a large sofa near the window and
started to explore each other. First removing our garments, then our
lingerie. Tess was so beautiful and I was lost in her charms. When she
lowering her mouth to mine we kissed as she moved her hands to my
breasts while releasing my bra. My hands were in her hair as I pulled
her close and slid back into her mouth, then to the side of her neck, my
hand slipping into her panty to find her rigid clit. She paused with me
holding her tightly as I removed the last of her delicate undergarments
leaving only the taut thong; my mouth now on her right breast. Her
nipples couldn't have been more sensitive as my teasing tongue caused
her to moan.
"Suck my clit." And I slipped down to engulf her sweet sex.
A mere few seconds and I was flooded with her first sweet seed. It
overflowing my lips. Tess moved to kiss me capturing it as she did and
then settled her tongue within my mouth. We rolled the snowball around.
I wasn't asleep but I'd closed my eyes as she removed the small plug. I
was smiling with her seed still on my tongue. Tess had moved to my pussy
and gently slid her fingers into both of my openings, the short finger
just barely opening my anus. Then her tongue went lower and she pushed
into the tight passage.
"The plug has helped open you. Can I fuck you here first to help us
remember how much alike we are?" I thought it a ruse but in a blink I
knew it was the right thought and reaching for her chin, nodded my
agreement.
"Don't be concerned I keep my body very clean Tess." During the past
weeks since meeting Mary I'd played with my bottom to prepare for Tess.
Now she was nearly in me and it was all I could think about. She stood
to retrieve a lube and I noticed she still had on her heels.
"Please bring my shoes here as well dear."
I slipped my foot into the first while she glanced down my slim body,
the other as she applied the lube.
"Fuck me Tess, please enter my body and share your clit with me." But
she had a different approach.
"No dear, you need to control the entry and pace. Let me lye there on
the sofa and you settle your bum over me okay?"
This was a good though and we shifted about, me slightly above her but
directing her meaty clit inward. The initial penetration seemed easy
since I lusted about this most every evening for days.
"Wow, we're together now, Ohhhhh !" Tess moaned as I withdrew a bit and
then slid right down allowing her deeply within me.
I leaned to kiss her mouth as my hands reached for her breasts than I
rested my head on her chest. She was holding me and we both were still
enjoying the connection of our bodies. Pushing up off of the sofa I
looked into her eyes.
"Now you fuck me Tess. Please fuck me Tess."
She was slow and subtle but the push was deeply felt.
"Oh yes, that's my girl, fuck me slowly, enjoy my tightness Tess! I feel
your clit, oh Tess! Wow you're getting larger as we move, yes, yes, ohhh
Tess, fuck me please."
When I played with my anal toys by myself it took at least five minutes
to reach peak but she had me so near I started to pant and moan.
Grasping her close to my face we kissed aggressively as she continued.
Her clit seemed to swell within me and then she screamed into my ear,
"I Love You !" just as the rush of her second release occurred. I was
startled but still reached my orgasm.
"Your butt is pulsing on my thickness dear. That's amazing! What a way
to start my Love."
We'd moved to the bed a bit later and continued playing until early
morning. Tess came in my mouth again and once in my pussy. I had five
orgasms that first night and early morning. Sore and tried I fell into a
deep slumber.
Tess had prepared breakfast and came to find me lying awake looking at
the juice still flowing from my bum. She smiled and ran over before I
could stop her, to lick me clean, both openings soothed with her tongue.
"I want all of you sexy Madeline. Nothing we shall do is beyond my love.
Now grab your robe and a panty and come sit with me near the window.
It's a lovely Friday. I have to leave shortly, you?"
I'd forgotten it was not a weekend and saw the clock near 10am. I was
late but didn't care.
"Can't we just shower together and return to bed Tess? I need more of
your loving."
She was full of energy and stated her intent, "I'll come back by two but
I must be at a meeting at eleven-thirty so I need to dress quickly."
I rolled onto my tummy and watched her from the bed as she prepared to
go out. I was still surprised at the pace our romance had taken and
happy as well. As I watched her a moment I realized I hadn't thought of
anything other than Tess since sometime yesterday. Realizing I'd
shutdown my phone as we'd traveled to her place I reached for my bag to
check my messages.
"I like that you shut that off last night Madeline. We had only each
other to focus on but now I need to go. What appointments do you have
this morning?" Tess said while pulling open her bureau.
My phone came to life. "Nothing urgent Tess." I saw three messages, one
from my assistant, and the others from Jenna.
"My morning meeting was cancelled late yesterday."
My assistants confirmed a late afternoon telcon arranged to resolve a
minor dispute. I could handle that offsite. Jenna wanted to see me over
the weekend. I hadn't considered her since o