Tess' Friend - Part Five, Dressed So
The following is the Fifth chapter. This is the continuing story about
Tess and her friends. Please consider reading the earlier submissions
to understand the development of these special Ladies.
What was I doing ! I had selected the file including my image and
pressed send. I hadn't consider the possibility that Charles would
react negatively to my looks. Well, maybe I was a bit anxious. I had
been living as a woman for nearly seven months when I ventured out as
Louisa. I had made the images almost a week ago, after having spent two
and a half hours preparing myself; I wanted just the right outfit, my
long blonde hair styled and my face on. I liked to wear my hair up
during the Spring. The affect showed my long neck with a simple pearl
pendant.
Nothing of consequence developed from my sending the image file.
Charles and I had been connected on a dating and chat service. After
both having completed the usual profile the service's computer had
matched us. Actually it had produced over 80 matches for me and I'd
selected Charles as the best after studying the numerous candidates. I
hadn't misled anyone but in the profile the question and boxes for
gender offered a chance to be less specific and I checked "not saying".
Together with my image I felt it was clear I was a transwoman. My other
attempt at the on-line matching, before I'd completed my transition,
had produce a lot of attention but from clearly a group of men
interested in a one night sexual relationship with a tranny.
I had decided that I would only continue using a dating service if I
could attract normal guys, and I wouldn't conceal my personal
situation. The profile questions didn't require a declaration of my
sexual history hence I didn't volunteer I was born a good-looking boy
of 69" height and near a 160 pounds. The "not saying" selection in a
profile was just for someone like me. A guy interested in gender girls
wouldn't cruise the "not saying" selections, or might he?
After a strict exercise and diet regiment over nine months I now fit a
size six, though my hips were naturally wide at just less than 38
inches. Having lost those 28 pounds had been a lot easier than I'd
thought possible when I'd started. My body had acclimated to the
workout and eating healthy foods and salads turned out to be
delightful. I just wish my hormones hadn't produced my bosom. I was now
a pert and full 35 C cup; I wanted more of an athletic chest, say a B
instead of the attention grabbing points I developed. I was getting too
much attention around town, even waiting at Starbucks, mostly from
married caffeine addicted businessmen.
At the start the job search had proven to be a challenge as well. I was
trained as a Graphic Illustrator having completed my Masters at Pratt
ten months ago. After many employment rejections I simply found a
physician in a small eastern state with a less aggressive policy
towards gender changes. The doctor had to certify my new sex and my
attorney prepared the documents. I easily changed my license and it was
a lot easier to describe myself as female rather than explain away my
genitals during an interview. But to protect myself from discovery I
decided not to entertain the numerous dating requests from colleagues.
After three months of working in the Ad Design office I spoke with the
Managing Partner about the behavior I described as 'near harassment' I
was encountering. I'd taken to wearing a ring on my left hand but the
comments regarding my 'coldness' and social exclusion were troublesome.
Fortunately my skill level had developed quickly and it allowed the
firm to grant my request to work from my home office two or three days
a week.
But back to Charles's respond; he was so taken with my standing shot! I
had worn a knee length dress of a simple design and a tall pair of
heels, but the dress hugged my slim frame and wide hips and he wants to
meet this coming Saturday. My cautious approach made me set the date
for 4:30pm at a nearby wine bar. We'd try a short date with the
agreement to not lead into dinner. I thought that provided a sufficient
amount of time to discover something about each other. A second date
might be arranged but I didn't have to promise. I was in charge of the
conditions. At least that's what I thought when we spoken by phone
Monday evening.
I must share that I found getting ready for this new experience to be
exciting. I'd met up with other men (and several women and 'girls')
prior to my transition but each of these dates had taught me that I
would never be treated as I wished. Though very passable I knew I felt
I wasn't truly ready and therefore it affected my behavior and my
date's attitude. The men sometimes noted something that brought a
question. Never an outright question such as 'are you a guy', because I
easily passed as a twenty-something girl. With each it was something
different. Several were aware I might be concealing a past and found an
excuse to leave quietly. Two were a bit too turned on and made
salacious requests that I won't dignify be reviewing.
I did date more than one man, several in fact, who clearly enjoyed my
sexuality. Michael was one who was special and caring. We spent several
nights together at a Hotel, he was a great lover and we enjoyed
ourselves. He was beautiful and caring but was a bit too gay for my
life. We're still friends and I can count on him in a pinch, in fact we
hooked up again right after I went fulltime.
One of the women I met was just terrific. She enjoyed helping me dress
so our dates started at her apartment. I had only been crossdressing
when we met a little more than two years ago. I was even then very
passable but my behavior and manner of moving was a dead tell. Donna
enjoyed helping me but she offered instructions only by full immersion.
"I'd love to teaching you Lulu, but I'll do so only when you're fully
dressed. You look like a woman dear, but you do not act like one of us.
The walking, sitting, the manner of your speech and subtle movements
are an important part of being a woman. Your body and face are going to
shake up any boy or girl that meets you. But you need to adjust so many
small actions. Now let's get you dressed and do your face. Your rats
nest needs some serious care as well."
Donna loved to play with me in bed after these lessons and I loved to
explore her body too. During the next few months she taught me how to
buy clothes that fit properly, shoes that weren't too slutty, and how
to treat my skin and cuticles properly. My near the shoulder hair was
always an issue and therefore when I'd let it grow out she took me to a
hair salon for an appropriate longer style. We had spent nearly three
months hanging out when I asked her to fuck me. All of our previous sex
hadn't included penetration. She was in charge in bed and she agreed on
this occasion to insert a special toy and do me right.
"Lulu I want you on the bed, atop the pink wedge. Yes, young Lady, lie
across it, bum up please dear. Lulu I can't see your tight little
hole."
Donna was dressed in heels and a chemise but without a thong, "Come on,
spread you legs a bit. That's better, and so cute."
She move to the edge of the bed and her fingers were playing at my rim
and her tongue licking lightly, "Make it wink at me Lu."
I listened and complied, she liked my willingness to submit, and I
wanted to have her thick play cock sliding deep inside me. "ohh that's
delightful Donna." She teased my bum for quite a long while.
"Women love to have our bums licked though most of us don't like anal.
Humm, I enjoy seeing the garters framing your bum. I hope you're wet
dear, this is the big one" she approached the bed and probed my tight
opening with first her long finger and then slipped her middle digit
inside me.
"Remember that you wanted it this way Louisa."
She came behind me and slowly slipped the head into my bottom. Donna
paused for some moments before she started to press her fake cock into
me. "Does this feel good sweetie?"
"Oh yes Donna, but slow, that's better. Maybe angle downward a bit;
yes, yes, Donna" I said looking over my shoulder. A moment later she
was completely buried inside me. She seemed really focused and I
considered whether she was enjoying the scene.
"Do you like fucking me, filling my bum mistress?" and then I saw her
smile.
"Yeah Baby Lu, I do like this, and the toy is getting me off as well."
Her orgasm arrived a bit before mine, but her cock didn't stop and I
exploded into my tight thong. She moved beside me on the bed and we
made out until she was ready for another try.
"I'm happy you're enjoying this type of play Donna." She reached into
my panty and lubed the cock with my wet seed. And than she rolled me
and mounted me again, though this time I could see her smile and eyes.
"Well, I just didn't see how I might enjoy stuffing a cock into an ass.
But yours is quite an ass Louisa."
The lessons continued for many months while I completed my studies.
After we'd been dating for nine months she told me she wanted me to
prepare for SRS. She had come to regard me as a lesbian like herself
and she wanted a partner. She wanted to share everything, and I was
surprised and couldn't dream of letting her know it wasn't in my plans.
She was 32 and wanted a baby, ours, not an adopted child. The idea of
me making this commitment, just after having completed my degree, than
to move into her home and get a legal marriage?
"I love your little cock Louisa but I want you to have a true pussy.
Fucking your ass is just not the same dear girl. We'll save some of
your essences for the right moment ok?"
I had moved toward being a bit submissive but I knew than I needed to
end our relationship. Her doctor had helped me arrange a better,
focused, hormone treatment and my breasts were so perfect. Being with
Donna had allowed me to evolve and my personality and manner had
developed fully; I was feminine. My closets were full of everything
except long gowns. We'd shopped together when we found an opportunity
and her advice helped me develop a complete wardrobe. She had made me a
more aware and dainty girl, and my tight bum could accept all of her
various toys, but I wanted something she didn't have. I wonder about
moving out and away but I knew what I had to do. I wanted a man and his
warm phallus. We parted badly, and she cried so much. Eventually Donna
adjusted and after a few months we are now friends, but we no longer
sleep together. In fact she's found a new girlfriend whom I really
like.
Donna's new lover is Sarah and she has been advising me since she and I
met about a month ago. She told Donna when we met that I could become a
very special transfemme if properly nurtured. Sarah had worked as a
catalog model and knew several transgender people in the City. She
introduced me to a dear older transfemme who offered guidance on the
legal and emotion issues I was addressing. There were of course
obstacles, my genital package should be addressed. Her friend
recommended I have my testes removed as soon as possible. I struggled
with the suggested but had the procedure done later that week at a
clinic specializing in gender cases.
I was ready to be treated as a woman, albeit without a vagina, and now
I hoped this possible new friend Charles would do so. He seemed to be
interested in me as such. I'm unconvinced he knew then how my world had
been changed. We met in a chatroom for singles, without any
pretensions. He was a handsome guy and I was, a girl, just looking for
someone to care for and be cared for, maybe to be loved? He didn't act
like the others, and I think I was somehow different as well. I didn't
go on line unless I was completely prepared; I didn't chat in a robe
and slippers. Maybe because I was dressed, my hair and face done it
affected my demeanor, and my personality. I guess its because now
looking back, I was a woman. I was no longer a boy who wore a dress.
That night we started our chat I wasn't dressed to go to a club, sexy
hose and sky-high heels, a short skirt, but in a simple yet beautiful
print dress and pantyhose, and black heels about 3" in height, with a
shell necklace and earrings. I'd touched up my makeup for the evening,
having shower when I returned from the office. My dinner was a small
salad and fruit, to help keep my skin clear, and my waist slim. I was
surprise when he came on line, a bit forward yet his icon included a
small image of him smiling. He made an introduction, I guessed by our
very near addresses; we were in the same city. He seemed to treat me
with respect and I wonder whether we'd met. On further thought I
realized that wasn't possible. After we'd stopped chatting I still
wondered about his kindness and almost an awareness of my recent past.
He was sensitive without prying.
Three months earlier I used another dating service based from Philly
hoping to have some anonymity. I'd met someone, a tall blonde haired
man about 31 years old from that City, and we were clearly attracted to
each other. After two weeks of chatting we arranged to meet in
Princeton. I'd gotten a room at an in town Hotel to prevent a difficult
Saturday night drive back to New York. The drinks at 6pm lead to
dinner, and then a long walk in the moonlight on the old Campus. He
seemed to understand my sexuality, though I'd been a bit bonny,
enjoying his nearness. We paused and he hugged me close and his hand
moved to my near flat mound, as if assuring his decision to bed a
transfemme. He kissed me,
"Don't run away Louisa, I want you just as you are."
I returned his kiss, deeply frenching his tongue, "You don't have to
ask twice," I said.
We walked back to his large suite overlooking the Square. I wasn't
drunk nor was I looking for a longtime lover. I just wanted to suck his
cock and have it deep inside me. I slipped my black A-line off of my
shoulders and approached him in my chemise still wearing my heels. I
pulled away his trousers and pants to find a thick and semi-hard cock.
My tongue ran down his length before I settled my mouth on his helmet.
This man was getting hard while I was getting excited.
"I love your cock, especially because I'm making you hard with my
mouth."
He smiled at my comment. "Suck me Louisa, I'll get bigger still dear
girl. Ahh, watch the teeth honey, ohh, wow, you've got me deep baby,
into your throat?"
I couldn't though I tried; he was huge now. I stopped for a moment,
stood and pulled him holding his cock toward the bed. "I'll get a bit
more comfortable" as I removed the chemise and my bra.
"That looks so sexy Louisa, I like the thong too, and wow to your
stockings."
I had prepared to attract him and it was having an affect. I bent to
release the clasp at the left hose. "Please leave them on honey."
"I'll bet you want to fuck me with my heels on too big boy?" I said
smiling lewdly, and rolling my hip.
"Come and sit on my nice cock dear girl. I want to fuck you." I moved
slowly toward him, dancing while I watched his dick quiver. I felt so
beautiful, but my small clitty was concealed and hidden with the thong
panel. I didn't intend to remove it; I liked keeping my clitty out of
sight, therefore out of mind. I was a sexy woman and he wanted some
pussy.
I slid across the bed to his member and went down on his cock again,
well some of it was in my mouth. Pausing and adjusting my position I
continued and his cock slipped deeper, deeper into my throat and I
allowed it to rest there while I adjusted to the girth. Slowly I moved
a bit, than slowly removed most of it from my mouth, but I wanted it
deep inside my throat again. This continued and he seemed to understand
that I was worshiping his phallus. My mouth was atop, than my tongue
along this length, my left hand holding his balls, my tongue licking
around and than sucking it into my mouth again. Thom tasted so good. I
continued to suckle him, in and out of my mouth, the motion stimulating
my body, in than I'd slip it out, back into my throat. I felt his hand
move to the base of his cock, to get my attention.
"I need your tight butt atop my cock now girl. Come here." He moved to
sit at the corner of the bed. I dropped to my knees and returned my
focus to his cock and licked the helmet slowly and looked into his
eyes, and than I moved up toward him, straddling his thighs and we
kissed as I felt him center the helmet at my opening. He was so gentle
as he slowly entered me. I could have been in heaven as each inch
slipped deeper into my bum. For several minutes he continued his
penetration, then he paused and we kissed, our tongues racing about
each other.
"Louisa I'm about to fuck your tight pussy now, are you ready?"
I decided to take control and moved my hips off his truck and his cock
slipped out as I reached the top of his helmet again. "Oh no you don't"
I cooed, "get back in my pussy" as I positioned him and moved downward.
I fucked him like this for some moments, than he flipped to a reverse
position, his cock now sliding deep into me. Thom had his hands on my
small tits, yet I was into this, his mauling my breasts. After I
adjusted his pace he came quickly, filling my bum with seed.
"Don't go anywhere my tight little girl, I'll rise again in twenty
minutes."
I oozed a little as I laid across the bed and casually played with his
soften shaft, and sure enough he was mine again. I enjoyed sucking his
cock for awhile, as he seemed to be napping.
His cock was solid though and I wanted it, "Hey big boy I'm going to
fuck you." This time I was atop and controlled the session. I liked
this position and he awoke, as I bounced on his thighs. He slipped from
my opening shooting my ass and hose with his release.
We fucked again sometime late in the darkness of night, and I was
oozing his juice as I fell asleep.
In the morning I was sore. I awoke before him and was still marveling
at his size, but three intercourse sessions were all my tight rose
could handle. He awoke and showered while I began to re-dress in my
outfit from last evening. He opened the bath door sporting a huge
erection.
"I'm too sore to take that monster again."
"Ohh no you're not sweetie. You're going to get fucked again," he said
as he walked quickly to me, grabbing my arm.
"No please, but I'll give you a blowjob ok?"
With that I went down on my knees, in just my bra, my soiled stockings
and thong. He was so large, and he seemed bigger than the evening
before, but I managed to wet his length and was enjoying his cock,
again, when he lifted me up, swung me around and licked my hole.
"I told you were mine to fuck again." And he set me down on my tummy at
the edge of the bed and forced that sword into my boi pussy. It wasn't
loving or gentle. He was hurting me as I tried to stop his thrusts. He
held my shoulders tight to the bed, my head nearly covered by a pillow.
With his left hand he pulled my one arm back around to restrain me. He
fucked me so hard I started to cry, unable to stop him.
"I love your fagity tight little cunny and you look so beautiful when
you sucked me off. Now I'm going to fill you with my juice you little
boy whore." He came into me and then pushed me to the carpet.
"Now get out of my room you disgusting Fairy." I was bleeding from his
penetration, but somehow gathered my things and limped out.
That wasn't my first error in judgment, oh no, I'd really made a bad
call the year before out on Fire Island. I met another transitioning
friend and we were on the Ferry over to the Island enjoying a bottle of
wine. Gloria hadn't been as fortunate as me. She could get close to a
drag look but didn't pass. She was ok with that, she was so sure of her
femininity that she just dealt with the abuse directed at her. But
we're on the queer boat together and a beautiful Adonis approaches us.
Speaking to me with a pair of bright blue eyes this hunk clearly wanted
me. "Can you and your 'friend' join me tonight at a party? They'll be
many other 'girls' and boys, maybe some whom you'll know, and we've got
a DJ, plenty of booze and even a barbecued pig going."
I decided without checking with Gloria that we were going to follow
this hunk to the end of Island if necessary. I was so randy with
anticipation; his golden hair, light beard, tight cheeks, wow. I hadn't
ever seen such a beauty, and I stopped thinking.
Anyway, the short story is we hooked up once at his party; turns out it
was his old man's party. The cutie pulled me into a room and we sucked
and fucked each other, then all hell broke lose. His sugar daddy burst
into the bedroom and pulled us apart, beating first Clarence then me
with a belt. I lost my falsies and bra but was somehow able to escape
further wrath by simply running, heels in hand, down the beach. I'd
forgotten about Gloria. Her abuse was worse than mine; four guys had
fucked her repeatedly and left her in the basement soiled and beaten.
She awoke the next morning alone and crawled back to our small rented
room. We never spoke about that night again and stopped seeing each
other shortly thereafter.
So on Saturday I allowed hours to prepare for Charles. I'd placed a
good deal of hope that this may lead to something special and possibly
sexual. I needed a real cock in me, soon, but I recognized my
anxiousness could spell doom and I re-focused on selecting my outfit.
The weather would be mild for early May and therefore I could wear a
dress and have a sweater along if it became too cool. That would
provide me a bit of freedom; the red dress would say too strongly I was
his, the lbd too sexy due to its length. Shoot I had four black
dresses, all a bit too much for a first meeting. I was eyeing the black
skirt and a soft cotton blouse. The skirt would look good if I worn
sheer nude stockings but Pantyhose would more conservative. I found my
newest set and considered the heels. I had recently bought a nice camel
colored pair but were they too tall at 4 ?" inches. Charles was tall,
6'-3" or so his profile said. I went to the Mac to confirm, so these
heels would say I was confident and sexy. But what ivory or white
lingerie set? I opened the drawer and reviewed the nine different sets.
The blouse had a modest plunge so the lacy ivory bra seemed just right.
I reached to my breasts to remind myself of how I'd changed since the
Princeton fiasco. I had to pray Charles wasn't that type. It was
several weeks after that attack before I'd been able to take a thin
dildo into my pussy. But maybe I should be a bit more discreet; the
soft cup Victoria's Secret set would be better. I would need a simple
short slip and I grabbed the first ivory one atop the collection in the
lower drawer.
My outfit was arranged and ready, now I need to bathe and pamper my
body. I decided to relieve some stress before hand and after my
ablutions I went to the club chair with my vibrator. Positioning my
legs over the sides of the chair I moistened the head of the toy. My
bottom easily allowed penetration. My favorite toy had the look and
feel of a real cock. I lubed the shaft and held the bulging end while
slowly running the tip along my perineum. As I slip the toy inside my
boi pussy I gasped, enjoying the fullness. Imagining a new lover my
mind brought my body along and within a few moments I was peaking. I
cupped my hand and caught my juice. Now relieved I now focused on
dressing just so.
So Charles agreed to a simple date, I think to confirm his impressions.
I was a Lady and would allow him to look as I studied his
contemplation. I wondered if I was I ready for a relationship, ready to
share my inner self as well as all of my secrets? Was he the right kind
of man, could he keep me sated? My sexuality was paramount; I needed to
be fucked many times a week. My toys were used daily and on weekends
multiple times a night. I'd sleep with a cock inside my pussy at least
once a week, so I knew I needed a lot of sex or I wouldn't be happy.
How does one confirm this scale of sexuality without testing the
waters? I found myself dreaming of his cock and his body atop me. I
smiled coyly, and figured that was a good sign.
While stepping from the shower I looked to the left and saw my image in
the door mounted mirror, the towel concealing my shrunken clitty. I
looked carefully at the very womanly form that was me. My friends had
always been clear, 'you're a beautiful crossdresser Patrick'. And now I
was a woman, not a part-time girl, with full high breasts and a narrow
waist. I was transfixed for a moment realizing where I been just 24
months ago.
Back in college in Chicago several of the 'girls' pushed me to consider
a sex change but I loved my small penis. One summer I'd had an
internship with a Fashion House. I met several other boys who were
quite beautiful when dressed as women. We spent that summer together
sharing our issues and dealing with the conflicts. Two of the group had
already transitioned, Tess was a local girl who had turned twenty a few
months earlier and had never thought of not being passable, and Susan
was from a Midwest farm. Though Susan had a very feminine face and only
a tiny Adam's apple she was being torn apart by the conflict with her
body and sexuality. I considered both of these 'girls' as more sexy and
gorgeous than myself, especially Tess. She made several passes but I
knew I didn't want that kind of relationship. I realized about this
time that I could become a good-looking young woman, and possibly I
could live a life as such. Maybe I could find a man to love what I was
without trying to 'revise' my groin. It was more than my wide hips and
thick, longish hair and soft voice that help me begin to see myself as
a woman. These boys who dressed had an impact on my thinking, on how I
considered my body and my sexual feelings.
When I was younger I'd had only one sexual encounter, with a girl near
my age, but she'd treated me to her pussy without allowing me to enter
her. Our sex play began and ended with our mouths and tongues.
"Patrick you are so soft and beautiful. I love that you take such good
care of your hair and nails. No gross hairy boy will ever be allowed
access to my pussy. Lick me again sweetie."
At eighteen I was still living as a boy but had allowed my hair to grow
even longer, and I wore genderless outfits and even heels and make-up
regularly. The girls worked for weeks over the summer to get me to
consider using hormones but I'd resisted. I wanted to be a natural
girl, I wanted to be liked by boys but not as a femme'. After an
interlude on the Pier with an unsuspecting tall dark hunk I agreed. I
wasn't prepared for a man to want me so strongly. His kisses and his
hands were touching me. I took his cock in my mouth and quickly brought
him off, my lips unable to contain his eruption.
The sexplay I'd had that summer was with a couple of the dressed boys,
their bodies slim and smooth. But this Latin man I'd met late one June
night was muscled and hairy, his phallus too large for me to consider
taking into my body. I'd been penetrated many times but the mini dicks
of the femme's I slept with couldn't match this man's meaty cock.
Afterward I considered what lay ahead and I knew I wanted to be loved
and fucked by a man, daily if possible. I settled on my plan and with
the help of Tess and others made the decision that hormones would
change my life.
I tried several combinations but Tess insisted; she brought me to her
doctor. This MD put me on a hormone therapy and of course I never
looked back. My skin started to clear and soften and my breasts started
to bud and my fat redistributed. After returning from the summer away I
was certain I would never be a boy again. The nagging question then was
'am I a gay male or a heterosexual transfemme?' but I knew I wasn't a
boy. I felt comfortable with my gender decision. I liked men, I like
their cocks, I didn't want a pussy between my legs. In fact I liked my
small clitty, reduced by the therapy.
Yesterday I'd receive an E-Mail update from my friend Tess. She seems
to have found a partner, but her search has been a difficult one. Tess
had transitioned before the age of eighteen and had become a serious
lipstick lesbian, heels, full make-up and great clothes. Finding a
woman, no, not just a woman but a beautiful woman, to love her was her
primary goal. So something noteworthy had to have occurred. I flashed
off a quick note of my personal situation, the legal ID changes, the
job, and now Charles' interest. Tess responded immediately, she was
coming to the City sometime within the next three weeks.
Her note said, "Take it slow Girl, and please be careful. I love you
Lu." She'd become my Big Sister from our time in Chicago but she
opposed me on my methods and discretion. I made a note on my calendar
and continued my preparations for the date. We hadn't seen each other
in over a year.
"I'm in love and feel great. I want the best for you, but I need to see
you soon Louisa." Tess was a good friend and we would settle the date
next week.
She was of course worried I might be gliding on my looks, not bringing
Charles to be aware of my gender history. She was a bit correct but
somehow I felt he knew, and wanted me just the same. I adjusted my
pantyhose and settled my breasts into the bra. The thong furthered the
restriction of my clitty. I was nearly as smooth as a genetic girl.
Tess's call had reminded me of the number of lesbians that were
attracted to me before I had breasts and my body was altered by the
hormones.
I checked my pocketbook for the usual protection and make-up items,
then applied a small amount of parfum. The slip and dress were adjusted
as I reviewed my outfit at the door. Some wrist bangles and a ruby
necklace were the final touches. I considered the possibility that
Charles was going to detect a surprise and run. Looking back to the
mirror I considered the possibly. No way!
"Madeline, I need to visit a friend in Manhattan. Can you get away
later next week?" Tess was anxious about her friend. Louisa was a truly
stunning beauty but she was still at risk. She wanted men to be
attracted to her beauty and almost never explained that she was in
transition.
"I can't stay away from Louisa. She could be hurt, but maybe not. Can
you travel with me sweetie? I'd love her to meet you as well."
Dressed just so Louisa moved along the sidewalk. She was comfortable
with herself, sharing a flirty moment with a gray haired gentleman as
she stepped along on Sixty-fifth Street. The bar that Charles selected
was a mere two blocks from her apartment. As she walked she considered
the coincidence. Could he have found her on-line, her address? The
thought vanished for she had arrived, pulling open the door and found
him seated at the Bar. He stood as Louisa approached, his large hand
extended, a soft smile greeting her. She was vulnerable and knew it.
She quickly ran her eyes over Charles, missing his doing the same to
her slim tall figure. He was a real hunk and his crotch seemed to
portent a fun sexuality. Louisa resisted a too familiar hug and grasped
his hand, while he helped her to a seat. Charles observed her choice of
hose when her skirt rode up a bit. The toned material running deep
passed the hem of her dress.
Their evening went very well; sharing an hour and a half, a delicious
wine and they were both very happy to have met. Charles didn't want the
date to end but he realized that Louisa might not feel the same. He
smiled and saw when Louisa moved slightly her pert breasts encased by
the simple bra.
"Can we get together again soon, maybe Wednesday after work?"
Louisa wanted to but remembered her rule. She was very excited being
near this man. He was special and he wasn't making her feel anything
other than beautiful.
"Can we talk after the weekend is settled? Charles, I don't want to
rush anything. I do like you but I want to go slow ok?"
She paused and continued, "You're wonderful and this was a great
evening and I'm excited for our next meeting."
He smiled and grasped her right hand softly "I agree this was nice and
I understand Louisa."
He suggested that he might walk her to her corner. Along the way he
paused under a street lamp to look at Louisa.
"I enjoyed this small date Louisa, but I'd love to take you to dinner
sometime soon?"
"I had a lovely evening Charles. Thank you."
Louisa smiled and took his hand and kissed his cheek, "Actually, I'd
love that Charles. Here's my cell number." She turned and walked a few
steps. "Please call me soon." She walked north a few blocks and turned
west.
Walking away from her new friend she reviewed the subtle signs of his
awareness. She was all but certain that he knew she was a 'new' girl.
She paused to consider why she'd not just come out and said so. It
worried her that her confidence was a bit shaky. But she had an agenda;
her mind was filled with his scent, his body and she had to dream about
these details, had to plunge her pussy as soon as possible.
Tess called Louisa mid afternoon Sunday. "Can we stay with you or
should I book a room?"
Louisa was excited to see her, meet this new special lady and spent
some time together.
"I haven't an extra room dear, this is Manhattan Tess."
"Ok we'll stay at the Four Seasons. Can you meet us there two weeks
from Friday, late afternoon?"
"I generally have an meeting Friday until almost 6pm, so maybe dinner
at the Hotel?"
"Sure, that can work. So tell me about him. Have you revealed any
special news?"
Louisa instead distracted her with news of her job, her new breasts and
anything other than responding to her question. Tess could see this
trip was important. She needed to help Louisa and would be happy to
help soften the news to this new man. But she considered the situation;
three beauties in tow, and he's told two are tranfemmes? It would be
too much for any man. She needed a plan to advance Louisa's
relationship, young as it may be.
"Can we meet Charles, maybe that Saturday for lunch?"
Louisa considered the question. "We've only just started to date Tess.
Let's see how things proceed during the coming weeks ok?"
"Oh, sure, I guess I misunderstood. I thought you'd been seeing him for
more than a month."
Louisa gave Tess the particulars of the on-line relationship and the
last date. "I'll see him on Wednesday." She'd decided to pursue the
date for lunch. She was beside herself with lust for Charles, though
they'd only barely kissed. Tess talked a bit of her new girlfriend but
was reserved pending the trip.
"So we'll see you in a few weeks, be as good as reasonable Lulu."
The rest of Sunday was quiet and she decided to retire with her toys.
Sometimes Louisa would just make love simply and quickly but she had
all day. She drew a bathe with oils and while it filled she selected
some lingerie and accessories. The dark waist clincher without garters
wasn't a necessity but it slimmed her profile. The suspender was a
beautiful dark grey with a wisp of lace and six clasps. The thong was
nearly a string but she didn't need to hold a big clitty. She recalled
a mid length chemise that would go nicely with the set, but no bra this
afternoon. The hose were seamed; getting them straight would take a few
moments, but the welt was divine lace almost 4" along the top of the
sheerest black silk.
Her toys were stored in a Kitchen drawer of all places. The longest was
over a foot but slim. The shiny pink double-ended dildo was selected
and set on the bedside table. Now to the bathe, oh, she wanted some
soft background sound. She decided to run a DVD movie of a group of
wild women doing sexy play, but which one? She selected a title
"Mary's First Anal" and opened the machine.
Slipping into the water with her long hair up she relaxed and
considered the decisions and possible outcomes. The soothing water
caused her mind to pause and just enjoy. The small clitty was now tiny
and she arose to her knees and cleansed her bottom. Stepping out to the
mat and drying she saw the movie's character inserting a long dildo
into her bum. She noted her heart rate and moved nearer to the screen
as she began to dress. The girl in the movie slowly continued to slide
the toy in, a bit deeper, then nearly remove it, only to re-insert it
even deeper. Lulu wasn't certain of the girl's toys length but it
nearly disappeared into her bum.
Padding her skin dry she turned to put the clincher on her torso. The
last time she'd checked her waist was at 27". Lulu walked to collect
her fabric tape. Before placing the tight garment about her waist was
now at 26". Not too proud, she smiled and looked at herself in the
mirror. The clincher now settled on her hips she gathered the
drawstrings bring her waist to almost 24". Gathering the suspender belt
about her narrowed waist she settled the garment and reached for the
first piece of silk. Once the right three hooks were attached to the
long hose she slipped into the 5" black stiletto. With the left hose
and heel on she returned to the DVD and watched the long thin object
disappeared into the girl's back passage.
"Oh my God, she's taken that whole toy inside herself!"
She considered her toy and returned to do her face and brush out her
hair. Stopping to notice the finish on her toes needed attention. She
grabbed the soft pink colored bottle and completed the digits.
Reviewing her hands she decided they were acceptable. Out of the corner
of her eye she noted that the girl had removed the phallus and was
sucking on it greedily with a second beauty on the bed with her. Lulu
smiled realizing she was going to attempt this wick act, burying her
dildo within her ass.
Louisa was a bit excited but she moved about the apartment enjoying the
luxurious lack of purpose. The whole of her person needed to be fucked,
and she would play for whatever time. Just taking her time. She went to
the window and opened the shades, though she wasn't fully dressed. The
light cast across her upper thighs and the sun caused glare to her
eyes. For several minutes she simply stood watching her neighbor
windows, unconcerned about who may be observing her poise and dress.
Charles wasn't paying attention to the game; the Colts were controlling
the Giants. His attention was on a note he was composing, to his new
friend Louisa. A beautiful girl, in his thoughts the most beautiful
he'd ever met. His terraced glass wall faced north and therefore was
always in shadow. Hence he tended to look about at the activities
across the inner block. He wasn't curious enough to have a pair of
spyglasses but he did find the world on the northern block interesting.
Some of the neighbors didn't close their blinds even while naked.
Others were like clockwork, open during the evening but shut for
bedtime. He hadn't been able to deduce any special individuals until
now. Just beyond the edge of the flatcreen there was a beauty clad only
in lingerie standing in front of the partially open drapery. She was
beautiful but too faraway to clearly see.
Just as he stood to get a closer look the woman turned and move off,
then the drapery closed. He noted her blonde hair was atop her head and
saw she had a long neck and lovely sexy legs. Returning to the sofa he
considered his new friend and hoped she had assets as nice.
Louisa moved to her bedroom and caught sight of the two girls using a
very long black fake cock in their asses. She settled atop the bed and
considered how best to use her toy. Reaching for it she smiled and
considered the realistic head. Slipping it into her mouth she licked
about the long shaft. The length was possibly 14" or four of her hands.
Slipping her thong panel aside she moistened her rosebud. Though she
had already lubed, her saliva was nearly perfect and she tasted her
moisture from the bum scent on her fingers. Maybe try this on her side?
She rolled to her left hip and using her right hand rested the phallus
at her opening. A small gasp still escaped her throat as the head moved
passed her first muscle. Pausing she checked to the video. The one girl
was stuffing the other girl's bum with the black toy. She followed suit
and the dildo entered into her valley to about 4", she rolled to her
tummy enjoying the fullness. She contemplated the toy and her cavity.
How did that long cock get so deep within the girl?
Shifting to the right side she withdrew the toy and brought it to her
mouth. When she was just cleaned she had no issue licking her fluids
off of her toys. Again she pressed the toy up but she twisted it
slightly as it moved and somehow more of the toy slipped inside. The
feeling of fullness was surprising and again she turned onto her tummy,
the end of the partially exposed toy dropped to the bed surface. She
relished this new feeling for several minutes, the meaty phallus moving
about inside her as she shifted slightly. Instead of a pounding fuck
her toy was somehow at home deep within her. Again she withdrew the
long toy, moistening it with her tongue and moved it inward again,
twisting but in the opposite direction and this time most of the toy
was trapped by her tight inner cavity. The toy was deep but the end
protruded.
"Wow" escaped from her mouth, her surprise so complete. This time when
she rolled to her tummy a new sensation was evident. The toy wasn't a
vibrator but due to her subtle movement it was stimulating her special
places. She realized she was excited enough to climax. It was deep
within, if she moved just so and felt the prick, it was fucking her or
at least it felt wonderful. She slipped a pillow beneath her tummy, and
just moved about, rolling side to side and, boom, she was coming, A
deeply felt climax continued for nearly a minute. A moment later she
was asleep or maybe passed out.
When I awoke, the phallus was still deep within my boi pussy. Removing
the 8 inches buried within me took a few moments and my full attention.
It reminded me of the rush of the orgasm. Pausing to consider the
intense pleasure I moved to the edge of the high bed still a bit woozy,
lowering my heels and went to the Kitchen to cleaned the now very
special phallus.
I was still in my sexy outfit when Charles called later that evening,
and we talked for well over an hour. I really liked him, how he
listened and paused to think when I spoke. We'd planned a lunch meeting
for Wednesday near his office off Madison Avenue.
I escaped from the Office a bit after Noon. I walked the short distance
in my black pumps. The place Charles had selected wasn't too busy and
they were able to talk quietly. He explained his new position at a
large accounting firm. He was the director of new clients and had to
travel lightly but enjoyed meeting the clients. He had studied
Accounting in Boston and completed a Masters in Marketing in Colorado.
"I started at this large firm about three years ago but was transferred
from their Miami office a couple of months ago. This is actually the
largest office within the firm."
Charles was the second child, born in the Midwest and the family lived
in Indiana. I shared my passed but kept to the general rather than the
details. He didn't need to know about my difficult teen life.
"I did a few years in a small college outside of Chicago but completed
my studies in Brooklyn. I see my career as a means to have an
independent life, rather than as a drive to work too much. I like to do
well but within a near forty hour work week."
I didn't explain the difficulty of being almost too beautiful, in a
City where every guy wanted a quick relationship and sex.
"My interest in dating is to expand my horizons. I need to meet people
and I love the social opportunities, but I want to, this may sound a
bit weird, but I want to control the situation a bit. Meeting in a
bar, or through friends can be ok, but there's a lack of sincerity, a
rush to get to the next step in a relationship."
Charles looked at me. "Your plan is a good one Louisa. Patience is
important to me as well."
We had a lovely date. I was in my business attire due to an afternoon
meeting away from the Office, low heels and a dark grey suit. My long
blonde hair was held in a ponytail. Though I was worried I was getting
too close he asked me to meet for a drink Friday evening near my
apartment.
"I'd like to see you again, sure, Friday evening can work, say after
6pm? Oh, but I have an early morning appointment so can we keep it
simple?"
He smiled. "Patience, it works for me."
I was a bit tardy Friday evening and I was excited to see Charles when
I arrived. He was standing near the doorway waiting. We relaxed with a
bottle of Pinot and shared an appetizer. Charles made me feel
comfortable as we talked until past eight but I told him I needed to
get some rest. We'd seen each other three times in less than a week.
"Can I walk you home Louisa?" I was tempted to bring him home but I had
to hold to my plan. Tess would have been proud. We walked quietly along
the stone sidewalk, my heels clicking. When we parted I kissed him
deeply, but stopped short as his hand moved across my behind.
"You feel wonderful in my arms Louisa." His hand played across my skirt
covered bottom.
He pulled me close enough that I could feel his cock. Could he feel my
small bump? I had to slow my responses, it was exciting to be held and
kissed by him, but I had to keep focused.
"Goodnight Charles," my hand lingering in his as we parted.
I saw him watching me from the corner, so a turned at the stoop and
waved goodbye. The feeling of his awareness of my sex seemed clearer
each time we were together.
I'd scheduled my 8:30am dental appointment weeks earlier, so I got off
early. When I returned I had a simple lunch. Now what to do? Charles
was on my mind, so I decided to try my deep toy again. After bathing I
dressed in a soft pastel blue lingerie set and I settled on the bed to
try to enter my tight hole. Again I started slow and only inserted
about 4 inches. On the next penetration I moved it deeper and then
relaxed. Removing it slowly I wondered about Charles cock. Would he
enjoy having my bum atop his cock? The final time I pushed and twisted
the toy inside I felt the upper tip of the long cock move slightly and
then slip in deeper. I almost jumped up to see how much was within me,
but I needn't, my fingers proved that the phallus was protruding less
then four inches from my tight rosebud. Again with the soft rolling
movement I brought myself to an orgasm. I wondered if others were
enjoying their toys in the same manner.
Charles called late in the afternoon and asked if I was free Sunday to
take a stroll in Central Park. The next day I wore a simple ankle
length flowered light dress and flat sandals. We met at the corner of
65th Street near the Zoo and walked for over two hours, flirting and
talking, and some light kissing. We stopped at the Boathouse for a
glass of wine and some light food and afterward Charles held me close
and kissed me deeply. I almost came from the excitement of his lips,
his chest pressing my breasts. His hand came to cup my right butt cheek
and I allowed the intimacy as he moved lower, holding me closer while
we kissed. He suggested we meet for dinner during the week; we would
speak in a few days about a plan. I was quite excited, his hardness was
distracting and I needed to be careful.
"Charles, I'm very attracted to you and love spending time together.
The relationship may be moving quicker than may be prudent. I'm excited
to be near you, but, ahh, I want to get home since tomorrow is a work
day."
"I completely agree, I love being near you Louisa. Your beauty is
intoxicating and I need to know that you feel comfortable. I don't want
a superficial relationship but a, I mean I want someone special. I want
a serious relationship too. And I'm following your cues, ok?"
Again he watched me but this time from a bit closer to my stoop. I was
definitively lusting about his body. The close hug had allowed me to
feel his semi-hardness. I almost couldn't believe my boyfriend is so
attracted to me. He seemed to understand my pause but I knew I needed
to clear the situation Monday.
I awoke early Monday and considered how to broach the subject. It was a
work from home day for me and I found starting early was helpful.
Around 10am the bell rung. There was a package at the door and I
slipped on my low heels and went to collect it. Returning to my
apartment I saw the package was from Charles. I opened it to find a
beautiful pearl necklace. It was a three strands and about 13" long. My
hand went to my throat, wondering if my very small Adam's apple was a
give away. I was in shock; I'd receive gifts from lovers but nothing
like this. I saw the note and quickly torn the seal. The note was quite
long, but in the third part he said he was falling in love with me. As
I sat slowly onto my Living Room sofa I read :
"Louisa you are a very special, a very beautiful woman and I want to be
with you. I feel you've a secret that you feel is holding us back, but
I assure you, nothing you are or were will change my heart. Please
consider my heart and share your painful past so I can truly love my
new woman."
How could he have found my secret? Was there a mistake I made. Someone
was divulging my history on-line? What could I do now? I was in shock
and slid down on the cushions and cried until I slept.
When I awoke near 1pm I looked at the package again. He had written his
address on the return panel. I went to my Mac and googled the location.
He lives on the next block! I ran to the window to check what this
implied. Mine was a fourth floor apartment, and his number was #302. He
could have witnessed my display the past week? Now I was so ashamed.
Could he have seen my little clitty from across the yards?
After crying again, I considered his note and re-read it. Was I reading
something between the lines? 'His new woman'? 'you are or WERE'? I was
so unhinged I got a glass of white wine even though it was only 2pm.
I needed the afternoon to think of how to see him. He worked in midtown
so at 6pm I walked to his address to await his return on the steps of
his Brownstone. This could prove a fool's errand. Now my phone was
ringing, a unique sound that meant my office needed me. I returned to
my apartment to deal with the office call.
After I dealt with the office matter it looked at the clock, 6:40pm. I
saw that Charles had tried to reach me on the cell. The message was
simple :
"I need to see you soon."
It was date stamped at 6:28pm. I considered what to do. I decided to
run to him, but I had to dress just so. I entered my closet but the
impulse to be clean lead to my ablutions and then a quick shower. I
just threw on a dress without stockings nor a bra. Just a thong and a
dress. I slipped on my flats and ran down the stairs but realized I
forgot the pearls. Returning I placed the pearl collar about my neck,
touching the very discrete bump at my throat. Maybe it was the tell?
I walked quickly around the block and paused at the bottom of Charles
stoop. I had an idea about what I was about to do, but it wasn't a
complete plan. I stepped up each of the stairs slowly considering my
options. I turned to return home; stop girl. Go to the bell and ring
for Charles!
"Hello?" it was his voice but I couldn't speak.
"Is someone there?" I was panicking. He wanted me right?
"Charles it's me, Louisa."
The door buzzed and I pushed it, but I heard the sound of falling feet,
pounding on the stair. We met on the second landing and he embraced me,
kissing me deeply, my very being. Wow, he did want me. After some
moments we walked up to his apartment. I didn't watch the steps, nor
the space, I was looking into his face, his eyes, and I felt his semi-
hardness again.
He opened the door; I pushed him aside and slammed it shut. Dropping to
my knees I pulled open his zipper while looking up to his eyes,
reaching within for the rising hardness. And then my mouth engulfed his
sex, his meaty thick long cock. It was now in me, my mouth was loving
him. My tongue was making him hard, harder; my fingers grasping the
thick cock that was pointing at my future. I wanted his seed in me, I
looked again to his face, he was watching me, and my eyes were seeing
Charles's soul, while I loved his great cock. I suckled him as he
started to pulse, the thickness swelling in my mouth and hand. And
boom, he exploded into me, my tongue trying to capture all of his
essence. I loved his salty seed, as it filled my mouth a bit escape and
dribbled down my right cheek. Was I in love? I needed more but I was
now surprised by my behavior. I wasn't this kind of girl, but I jumped
up, the cum still on my cheek, and kissed him. I nearly collapsed but I
had to run away. Turning, I opened the door and ran down the stairs. It
took a moment for Charles to realize I was leaving but by then I was on
the stairs. He called to me but I needed to get away.
I didn't return home for several hours. I wandered the Upper East Side
just trying to comprehend my actions and the possible impact. I was
moving slowly along the sidewalk in front of my Brownstone when I saw
Charles, sitting near the door.
"I'm just happy to see you're ok Louisa." He arose and started down the
steps passing so near. I could feel his warmth and reached to touch
him. He took my hand and kissed it gently.
"Call me sometime tomorrow, and get some sleep. I loved your very
special kiss Louisa," and he stepped away while looking over his
shoulder, smiling.
In the morning I decided to ask him to a late lunch, but I had a lot to
do. My hairdresser found a spot for me at 10:30am. I'd planned my
outfit, hoping we might find a reason to runoff the afternoon. I texted
Charles and he agreed to meet at the MoMA bar at 1:30pm. I had to get
my face just right and was dressing at 12:30pm. For this date I was
going with the lacy ivory lingerie, a shelf bra and nude hose with a
lovely 4" white lace welt, a lovely white suit and 5" white heels. The
clincher wasn't necessary but I wanted to be dressed just so he'd want
to spend the afternoon with me; just me and Charles. I'd primed my
rosebud after my cleansing. Looking into the mirror I placed the pearl
collar about my neck; they were so beautiful. Then I brushed out my
hair and set it in a half up bun. My afternoon face was easy; mascara
and lipstick, oh and some blush. I was in a taxi at 1:10pm and traffic
was only a bit heavy. The young cute driver tried to flirt.
"Miss you must be going to a photo shoot. You look so beautiful. And
you've got a great smile, and wow, sexy legs." I smiled but turned to
watch the pedestrians along the way down Fifth Avenue.
I was seated at the Bar when Charles turned the corner entering the
MoMA bar. He smiled when he saw me. I turned on the stool as he
approached, my legs flashing my stockings, he kissed me tenderly and
grasped my waist.
"You are a vision my beautiful girlfriend. Can you buy me a drink?"
We talked of simple things, but I stopped him.
"Charles, I want to apologize for my behavior yesterday. I can't say I
didn't want to have you, but my running away surprised me. You're
special to see me today."
"You're kidding, right? You needn't ask for my forgiveness Louisa."
"But do you still want me Charles, even though I acted like a slut, I
mean do you want me, like I want you?"
He just tilted his head and moved closer, then he kissed me deeply, the
longing evident.
"Can you spare the afternoon? I'd like to take you to the St. Regis for
the afternoon."
We left after the glass of white wine. I was happily looking at him as
he guided us out to the street to a taxi. Once in the car his hands
were all over me; my legs and breasts were clearly ok to him during the
short ride. I wasn't too disheveled when I stepped out to the Valet.
We got a simple room, which was still extraordinary. After the Butler
left I approached him and pushed his jacket off, turning to hang it up.
"Can I kiss you again?" as I removed my suit jacket.
He smiled as I dropped to my knees and again released his beautiful
cock. He wasn't flaccid but I immediately licked his entire length,
measuring as I did. He was large but not too big, thick but not too
great. My stay-on lipstick was leaving a stain just below his helmet
and as he stiffened he stopped me. I needed to be certain he
understood. I didn't want to be mistreated nor did I want to deceive
him, "Charles do you understand about my, ahh, how I'm not like other
girls?"
"Louisa, I need to be inside," he stumbled his speech, "huh, inside
your, can I watch you disrobe?" He was nervous as he pulled me to my
heels and it was exciting that he needed me to show him what to do.
I smiled and stepped back three steps, turning while I unfastened the
button and zip of my skirt. It slipped to the floor and I posed a
moment and released the clasp in my hair.
Spinning about on my tall heels I posed my bubble butt by rotating my
left hip, "Can I interest you in my unique pussy Big Boy?" Charles
leaned back, his bottom on the bed, his cock was hard as I walked
closer. He stood and positioned me on the edge of the bed, tittering on
my 5" heels. He seemed to be aware of my thong as he pushed it aside
and licked me deeply, his tongue at my hole. He placed his cock at my
opening.
"You need to take over Louisa. Slide my cock inside your body please."
I would handle his meaty cock, reaching for the shaft I settled just
the tip into my opening and I paused for a breathe. Turning to look
over my shoulder at Charles I slid down a few inches and stopped. I
worked my hips in a slow circle, holding him inside me. I continued so
slowly, relishing his girth as his balls reached my bum.
"You're so tight and smooth dear. Fuck my cock baby."
Slowly I increased the pace of the plunging, and the depth, but I
couldn't easily look to his face. I paused and he slid out of me and I
mounted the bed. He followed me lying down, his head on a pillow. I
shifted up toward him while on my knees, looking into his eyes I pushed
down atop his cock.
"Do you like my pussy just a bit? Can you see fucking me every day
honey? I need a lot of cock, and your sweet seed. You're getting a bit
flushed Big Boy. Can you please fill my pussy? I want you to erupt
inside of me dear. Or do you want to fill my mouth? Please just love
me, love my body, love my heart."
He couldn't hold his orgasm any longer, and Charles came strongly, and
I came as well. Maybe not a release like a boy but I trembled as I rode
his great cock like a pornstar, my heels aside his knees. We made love
a second time a bit later, after he inspected my clitty and licked my
gushing rosebud. He snowballed his seed with me. The champagne arrived
and I covered up when the sweet young waiter came in, his dick semi-
erect seeing my scattered lingerie.
We talked until near dinnertime. He explained how he'd come to
appreciate the world of transfemmes. Early this year he had dated a
girl from a Canadian city for a month while on an assignment. She
wasn't totally into guys and therefore not for him. I thanked the good
fairy for finding this special man. He seemed to love my body, and just
before dinner he took my clitty in his lips and though small, I
released a small amount of sweet seed.
I was falling in love with Charles.
On Wednesday morning I had to get home so I left Charles at the Hotel
around 6am. Before I left I woke him with my mouth on this beautiful
soft cock. He was limp but my mouth settled that quickly. His seed was
deep in my belly as I got the taxi; a breakfast before an office day.
Tess called me later that afternoon. "So is he as nice as you'd hope?
As sexy as he appeared?"
I gushed for nearly twenty minutes. She got a clear understanding after
I said 'I love his cock' four times.
"So he knows of your history?"
Tess could be such a big sis "Of course he does."
"And you told him about Madeline and I?"
"No way dear Tess. That's for you to decide, not me. But don't worry.
Charles will love you two beauties."
Later that evening we spoke on the phone, Charles asked if he could
visit that evening but I was behind at work. We agreed to sleep at his
apartment Thursday night. We discussed getting some take-out, but the
sex was what we both intended to enjoy. We awaited the delivery petting
and kissing on the couch. As soon as the bill was settled he stripped
off my dress and laid me across the sofa arm. Taking me from behind.
Previously this hadn't been a favorite for me. Maybe he just was
special, his cock slipped deeply inside me, not as deep as my toy had
the other day, but his cock was alive and warm and I came more quickly
then the first two times. He filled my cunny and I wondered if he might
clean me like the other evening.
I didn't need my lover to enjoy sharing his seed every time. I just
loved that he was that much in lust with me. Maybe lust is ok at this
point? We fucked in the middle of the night with me riding him reverse
cowgirl. My little clitty was bouncing a bit because we were sleeping
naked. The size of his phallus was not evident but I felt him deeper in
this position. He came holding me tightly and I awoke with his still
swollen member in my ass.
In the morning he asked about my past girlfriends.
"How did you know I've been with women?"
He got a bit tense "I just figured you'd have been helped, I mean, in a
positive way, ahh, by other women. Women who wanted to enjoy your sexy
body." But I wondered if he was being completely forthright.
"Do you feel comfortable that I've had multiple partners Charles?" I
hoped he'd say yes.
"Of course, it's just that I've watch others struggle with gender based
discrimination. Ahh, someone very close."
I looked at Charles, my big stud, and he had a small tear forming. "Are
you ok sweetie? Can you talk about this comfortably?"
I was near enough for a hug and he started to weep "My sister is gay
Louisa, and she has struggled to find acceptance. There are so many
subtle sub groups in the gay community and Missy hasn't found someone."
This discussion needed more time, I hugged him, "Can we talk about this
over the weekend Charles? This is important for me to understand and
support you but I've got an appointment in thirty-five minutes, Ok?"
On Friday afternoon I asked Charles to find something to do that
evening. I wanted to see Tess and her new lover without being
distracted by his nearby phallus. I met the girls in the Bar of the
Hotel, and they were dressed for the evening whereas I was in my
business skirt and 3" heels.
"Tess didn't tell me you worked in Fashion Louisa. You are so much more
beautiful than her old photos" Madeline said as she kissed my cheek and
hugged me. "And so slim too."
Her smile made me think of how far I had come to be me. I sat between
the two girls and the wine arrived. "So Madeline, how did she snag you?
She can get very possessive huh?"
Seeing these two beauties, with their lovely long legs and sexy heels,
they're hair styled and the faces made to perfection was great. I
didn't miss my lesbian days but women can be so soft and smelled
luscious and their skin so smooth. I felt a bit dowdy surrounded by the
Manhattan evening crowd.
Tess jumped in. "Don't be opening any secrets, either of you, at least
not until tomorrow. I found her wandering about at my club, you recall
I mentioned Faunesse Lulu." Tess and Madeline describe their history.
"Than you've only been together about 3 months?" I sipped the cool
wine.
Madeline smiled. "It's been nearly four now."
"Has she tied you up yet?" I giggled recalling a past tradition of
Tess'.
"I asked for no secrets Lu! And no, I'm into Maddie's beauty, not
pain." Tess wasn't perturbed.
We dined at Sette on the East side, than returned to their Hotel for a
drink in their room. I could enjoy Tess from a different perspective. I
wasn't being chased and pushed by her. Madeline was an amazing beauty,
a bit taller than me, and five pound lighter. I found myself
strategizing a new diet. Tess looked extraordinary also. She'd trimmed
a bit and was happy to be in love. I didn't feel nor look sexy but Tess
was shocked by my figure, the length of my hair and the style. She also
commented on my manner.
"You've learned a great deal young Lady." Tess ordered a bottle of Moet
and met us at the window. "Lets take a bathe, did Maddie show you the