Roberta Montgomery Part 2
- 3 years ago
- 28
- 0
Roberta Montgomery - Part 1 free porn video
Roberta Montgomery - Part 1
Chapter 1 - Proposal
"Sweetie!" In the fog of sleep, I heard my girlfriend's voice. "Sweetie!
Sweetie, wake up! Sweetie!" Initially, the sound was distant, but it
quickly grew closer. Suddenly, I felt myself being shaken. I awoke to
Margret (yes, spelled without the second "A") hovering over me, with her
hands on my upper arm. She gave me a moment to collect myself.
Eventually, I asked her what was wrong, thinking there was an emergency.
"Nothing's wrong," she replied. "Sweetie... I know it's an odd hour, but
I really need to talk to you. It can't wait."
My name is Robert Bingham, and I go by "Bobby" to family and friends. It
was just after 3:00 a.m., and we were in the house of Margret
Montgomery, my girlfriend. We had met each other about two and a half
years ago, and we started dating soon after. We became infatuated with
each other very quickly, and it was rare that we didn't spend the night
together, either at her house or at my apartment. During the past few
months, we'd gotten in the habit of staying at her place much more
often; and recently, we had discussed my moving in with her. She had
more space, a more comfortable bed, and her house was somewhat secluded,
certainly more so than my place. Seclusion was a prime factor, because
privacy had become more important to us in recent months, considering
our lifestyle.
With Margret's help, I sat up and got situated. Being fully awake, she
had me at a conversational disadvantage, but the feeling of a metal ring
being slid over my finger got my full attention. I glanced downward at
my left hand, which was being held in both of Margret's hands. On my
ring finger was a golden ring with a heart-shaped diamond in the
setting. It wasn't small.
"Roberta, please be my wife!" We both still were in the bed, and Margret
was kneeling directly in front of me. She stared into my eyes with a
sense of urgency, as though one of us were about to go overseas to fight
in a war.
Chapter 2 - Backstory
When it came to our sex life, Margret and I both enjoyed a few kinks.
Initially, it was just erotic play, and I typically went with the flow
of Margret's imagination. After a few weeks of dating, she got the
notion to have me cross dress for her one weekend, complete with makeup,
nail polish, and high heels. I went along with it for her sake; and
while I'll admit it was fun, in a playfully erotic way, it wasn't any
different for me that any of the other kinky things we had experienced
together. Anything that I did with Margret was enjoyable.
However, Margret was more excited over my cross dressing than anything
else we had done, and she was in heaven for that entire weekend. Not
only did I have the best (and the most) sex of my life that weekend, but
during what little time we weren't in bed, Margret was more attentive to
me than ever before. She constantly complimented me, physically handled
me, put her arm over my shoulder when we watched a movie... she treated
me the way a man treats a woman whom he loves. She laughed and hugged me
when I told her that, but then she seductively whispered in my ear,
"Sweetie, you ARE the woman I love!" From then on, she took to calling
me "sweetie" all of the time, no matter how I was dressed, but I didn't
think anything of it. I enjoyed all of the attention, and I admitted as
much to Margret, but I considered it to be just another fun weekend of
sexual exploration.
Soon after, Margret confessed to me that she had a strong attraction to
feminine males. She explained that she wasn't gay, but she always had
found cross dressers and transsexuals irresistible. Margret told me that
her intention from our first date was to determine whether I'd be into
cross dressing, and she wanted me to explore my femininity more often.
She found it difficult to tell me that, and she knew that it might be
hard for me to hear, but it was something about her that I had to know,
and accept, if we were going to continue dating. She profusely
apologized for making her confession seem like an ultimatum, but she
made it clear that she wasn't apologizing for the way she was.
Naturally, I needed time to process what she had confessed, and she was
very patient with me.
Over the next several months, we had countless conversations about what
we wanted from our relationship, and I allowed her to continue
feminizing me on occasion. We shared equal enthusiasm for most of our
erotic activities, such as BDSM, role playing scenarios (sometimes with
elaborate costumes and loose scripts, from which we would ad lib), the
use of vibrators and dildos, etc. Once in a while, one of us would come
up with an idea that didn't really excite the other; but we still
explored each other's kinks, and neither of us ever suggested anything
seriously dangerous or overtly public. While drag wasn't one of my
kinks, it clearly pleased her, so I was fine with it. What I discovered
about myself, though, was how much more I enjoyed being with Margret
when I was in "Roberta" mode (as she named me when I dressed as a woman
for her sake).
While I certainly looked different when in drag, Margret's personality
transformed even more. She always had been a fun, energetic, intriguing
woman with me as Bobby; but around Roberta, she exposed an additional
layer of her soul. She became more mature, protective, assertive, and
dominant, in a positive way. She never talked down to me or made me feel
smothered, but she more often took the initiative and sometimes made
plans without asking me. When we would go out to sit on her back patio,
she always held open the door for me, or when we sat at the dinner
table, she always pulled out the chair for me. She never would do those
things for me when I was Bobby.
After having cross dressed for Margret on several occasions, I began to
notice a significant drop in her enthusiasm around me when I was dressed
as a man. We still enjoyed being together, and the sex was still good;
but when I became Roberta for her, the sex was mind-blowing. Even our
non-sexual activities were enhanced when it was "just us girls."
Granted, Margret always was the "top" in our relationship, even when I
was being my relatively masculine self. But when I was being feminine,
Margret shifted gears into "pure alpha female" status (my phrase), which
made her feel more comfortable. As she explained it, she was concerned
that Bobby would be turned off by her natural aggressiveness, so she
always felt that she had to hold back with him; whereas Roberta seemed
more vulnerable and receptive to Margret's dominance, so she was free to
be herself to a greater degree.
Initially, I never felt like I was any different dressed either way; I
only felt different because Margret treated me differently. Over time,
my attitude began to change, and I didn't really notice that about
myself until I spent several hours alone one day. Margret unexpectedly
had to go into work on a Saturday, after I had already cross dressed and
cooked breakfast. She told me to stay feminine, because she wouldn't be
long; but two hours later, she called from her office and told me she'd
be stuck working all day, so I could go ahead and change back into my
"Bobby clothes." However, I spent the whole day alone dressed as
Roberta, and it felt natural. I had no desire to "get out of costume,"
even though my girlfriend wasn't around to enjoy it. I even found myself
maintaining the feminine mannerisms and movements that I had been
practicing for the role. That day, I felt like a woman instead of a man
in drag, and I didn't know what to make of it.
Margret came home that evening exhausted and quite pissed about having
one of her special "Roberta" weekends ruined, but I surprised her by
greeting her at the door wearing heavy makeup, a tight, sleeveless
minidress, spiked heels, and my hair extension in a high ponytail.
Without saying a word, I wrapped my arms around her neck, passionately
kissed her, then took her jacket and briefcase and tucked them away in
the closet. I then took her hand and led her into the dining room, where
I had prepared a full banquet, fit for an empress. It was the most
ambitious meal I had ever attempted to cook. Stunned, Margret slowly sat
down at the head of the table. I quickly donned an apron and poured her
favorite drink (stout beer, which didn't necessarily go with the meal,
but this was about serving her needs, not showing off my wine pairing
knowledge).
I turned away to uncover the serving dish so that I could fill her plate
with the first serving my culinary masterpiece; but when I turned back,
Margret was crying, and I could see tears dropping into her dinner
plate. I panicked, thinking I must've done something wrong. Before I
could ask, Margret rose and grabbed me. Still crying, she hugged me with
all of her strength.
"Oh, Roberta! You just turned one of the most miserable days of my life
into the best day of my life! If you knew what a bullshit dumpster fire
I had to deal with today... this is just... there's nothing else you
could've done that would've meant so much to me! Oh God, sweetie, I love
you so much! Thank you, thank you, thank you! You're my sweet, sexy,
little angel!"
When Margret finally let go, I joked that I feared I was going to die
from suffocation or having broken ribs puncture my lungs. She wiped her
tears and laughed, then grabbed my head with both hands, and kissed me
hard, three times. After eating and drinking our fill, Margret literally
dragged me upstairs to the bedroom, and we made love until sunrise,
despite her fatigue from working all day. I thought she would get a kick
out of finding Roberta waiting for her when she got home, but I really
didn't expect such an emotional reaction. That night taught me just how
much my feminine side meant to the love of my life.
As our relationship progressed, I no longer approached my cross dressing
as a mere activity that I engaged in during our kinky weekends. Instead,
each time I dressed up, I felt wholly transformed into my alter ego,
Roberta. And when I did so, all I wanted to do was make my darling
Margret happy. I expressed my confusion to Margret in many of our
conversations. Was I simply becoming acclimated to cross dressing
because I knew how important it was to my lover, or was I actually
starting to identify as Roberta as much as I identified as Bobby?
Margret loved that I was becoming more comfortable dressing and behaving
as a woman, and she continued to encourage me to do so more often. It
reached the point that, on every weekend and holiday, I was expected to
be Roberta by default. We both had office jobs during weekdays, and my
cross dressing had become so thorough, that I didn't have time to
transform during the week. That meant I still was Bobby, Monday through
Friday, and that frustrated Margret more and more as time passed.
Margret didn't want to pressure me, but she couldn't help herself. She
had crossed the threshold of loving Roberta more than Bobby, creating a
virtual love triangle.
Eventually, something had to give, but I didn't know how far I could
take this... or to be more accurate, how far I could let this take me.
Would adding weeknights even be enough for Margret, or would I need to
become Roberta full-time to satisfy the woman I love? Was I prepared to
break up with Margret to retain my manhood? It's not that I hated
dressing and behaving as a woman for her; in fact, I've grown to enjoy
our pseudo-lesbian weekends. But if we continue on this path, how will
my feminization affect our interaction with the rest of the world? So
far, only Margret knows about Roberta. Despite our open communication,
there's still an important question that I can't even answer for myself,
much less for Margret.
Chapter 3 - The Irresistible Force
Margret continued to stare at me, with her proposal hanging in the air.
I was in shock. We had discussed the possibility of marriage, but I had
no idea that she was ready to propose... although, I figured that when
the time came, she'd be the one to ask for my hand. It was only the
timing that surprised me, both by the calendar and by the clock.
"Margret, dear, it's three in the morning."
"I know... I'm sorry, sweetie. I tried to wait until later this morning,
but I've been staring a hole in the ceiling for the past three hours,
and my heart keeps beating faster just thinking about it. This is too
important, and I've already made up my mind. I bought the ring this
afternoon, on the way home. I was going to ask you at breakfast after we
were both well-rested and clear-headed, but... well, you know how I am
when something's this important to me... to us."
I looked back at the ring. "It's beautiful... and very feminine."
"It's a pink diamond, your favorite color, sweetie." She had playfully
decided months ago that pink would be my favorite color from then on.
Only now, it's not so playful.
"So, to be clear, you just asked Roberta to marry you, not Bobby,
correct?"
"Yes. I want YOU, ROBERTA, to be my lawfully wedded wife, for all
eternity. Fuck death!"
I nervously chuckled, but I knew Margret was serious. I love this woman
so much, and I can't bare to let go of her; but I know what she's
asking. We've had these conversations many times, and I know exactly
what she wants and needs. I want to marry her. It's simply a matter of
whether I want to be Roberta for her... permanently. I only wish that my
communication with myself was as open as my communication with Margret.
She was so much more confident and headstrong than I, generally
speaking; but when it came to my femininity, she was downright dogmatic,
as though it were a foregone conclusion. Obviously, I wasn't quite so
comfortable with it.
"But Margret, what about my job? And how would we handle our families
and friends? We've met each other's families only a couple of times. How
would they react?"
"Sweetie, don't you worry your pretty little ahead about anyone else.
I'll take care of my wife; and if anyone gives you any shit, I'll make
sure they know what time it is and who winds the clocks around here."
I started to giggle, but I could see that Margret wasn't joking. She was
prepared to get in people's faces, draw lines in the sand, and write off
anyone who wasn't on board with us. She was an equal partner in her law
firm with two other friends from law school. Of the three, she was the
"wartime consigliere" when cases couldn't avoid going to court. In fact,
her courtroom reputation was so fierce that it made things easier for
her two partners during their settlement negotiations, because no one
wanted to square off against her in court. That suited Margret just
fine, because she didn't enjoy the research side of practicing law, at
which her partners excelled. Long story short, confrontation wasn't
something that kept her awake at night. She easily could handle our
families and friends, if I actually took the drastic step of living as a
woman for my wife... or would she be my husband?
I so loved it when Margret had that intimidating expression on her face.
It wasn't aimed at me, but I still felt it, and it always turned me on.
I calmly responded, "O.K., point taken. You probably can smooth things
over in our private lives. But, I still have a good job... in a
professional office environment. I can't just tell everyone, 'Hey, even
though I'm not trans, my wife wants me to be a girl, so I'll be dressing
and acting like one from now on. I hope that's not awkward for any of
you.'"
Margret flashed an understanding smile. "Your point also is taken,
although it's a moot one."
Inquisitively, I raised my eyebrows, and she moved into kissing range. I
could feel the breath from her nose on my skin. She wasn't looking
directly into my eyes; instead, she was studying the contours of my
face, as though pondering a work of art. A couple of seconds later, it
felt more like she was salivating over the presentation of a delicious
meal that I had just served.
"Sweetie, no wife of mine will ever have to work a single day outside of
our home... nor will I allow it. Roberta, you'll be living the dream
life... that of a traditional housewife. You'll spend your days cooking
and cleaning for me, wearing the beautiful dresses, shoes, makeup, and
jewelry that I'll buy for you. I'll be the breadwinner and head of our
household. I'll take care of all of those pesky bills and expenses we
incur. I'll always provide for you, protect you, and shelter you from
that big, bad world out there. When I come home from work every day,
you'll be here to comfort me, to help me relax, to serve me, and to wait
on me hand and foot, which we both know you enjoy."
Margret then forced herself on me, and she met absolutely no resistance.
She pushed me back down on the mattress and probed my mouth with her
tongue while maneuvering her body directly over mine. She took my wrists
and pinned them next to my ears, properly mounted me, and began
grinding. Did I mention that I love this woman?
As usual, we climaxed simultaneously. I had learned how to sync my
body's rhythms with hers, so that we never were more than a couple of
seconds apart. Her body emits strong sexual waves, making it easy for me
align my orgasms, my heartbeat, and my breathing with hers... whether
that's real or just my imagination, it always works. While we often
gently make love to each other for hours when we have the time, this was
a one-sided power fuck on Margret's part. It was quick and our eruptions
were violent. This particular act was more about the lustful assertion
of her sexual dominance over me than a physical expression of love,
although an undertone of pure love always was present between us.
After we caught our collective breath, she starting kissing me again,
still lying on top of me, and asked, "So, is that a 'yes'?"
"Margret, you know I want to please you, more than anything. And I want
to marry you. But you're asking me to become a woman for you, full-time.
That's a big ask." I couldn't help but chuckle at my own understatement.
"Yes, I realize that. I know it'll be difficult at first, for you to
adjust to being feminine around others, and that's why I'm taking over.
All you need to say "Yes, I'll marry you," which we both know you want
to do, and I'll take it from there. You won't have to worry about
anything else. I'll do all of the thinking and planning for both of us.
You'll simply need to have complete faith in me. Just trust me, follow
my lead, and do exactly as you're told, sweetie. I'll take care of you."
I smiled. "You know how attracted I am to you when you talk like that.
It's an unfair tactic."
She smiled. "Like what, sweetie?"
"Oh, don't give me that innocent look," I giggled. "You know... when you
get all domineering like that... I get all tingly and passive. Not only
do you expect me to become your wife, you want me to become your
obedient wife. What if I want a career, too?"
"Oh, sweetie, being a housewife will be your career. It's a perfectly
legitimate occupation. And if you ask me, you housewives don't get
nearly enough appreciation and recognition in our society. I promise you
that, as your female husband, I'll never take you for granted."
"Let's table the housewife part for now and focus on the part where you
expect me to transition from living as a man to living as a woman for
the rest of my life."
"Yes, and you have a problem with that because...?" We were both
giggling at this point.
"Come on, now. It's one thing to dress up for you on weekends, but every
day, for life, is a complete lifestyle change. I'll have to get used to
putting on my makeup every morning, doing my hair, keeping my
fingernails and toenails painted all the time (to meet with your
approval), having a completely different type of wardrobe than I grew up
wearing (with all of the buttons on the wrong side), getting used to
wearing the high heels you love seeing me in almost every day, keeping
my arms and legs shaved... and my face will need shaving twice a day,
not to mention all of the facial and body moisturizing routines I'll
have to adopt. And that's just for my outward appearance."
"Sweetie, I'll pay to have all of your facial and body hair permanently
removed, so that argument won't fly. And, if you don't think you'll
enjoy doing your makeup every morning (but I think you will), then I can
take you to the beauty clinic to have most of your makeup tattooed on.
They do great work; one of my girlfriends had her eyebrows and liner
done, and she loves it... saves her thirty minutes every morning, she
claims. And don't even try to pretend that you don't enjoy wearing all
of those pretty dresses I've bought you so far. You get a kick out of
showing off your sexy legs for me. I sure as Hell enjoy it."
I sighed, feeling that I was losing every point of this debate. "And
what about beneath the skin? Socially, psychologically, emotionally...
becoming a woman, not just with you, but all the time I'm alone, and all
the time we're with family, friends, strangers... everywhere we go,
everything we do... I'll always be Roberta, and Bobby will be gone
forever. Everyone else will start treating me as a woman, and I'll have
to think of myself as a woman, too. That's a monumental adjustment,
especially for someone who isn't even transsexual to start with. It
could be traumatic for me. The more I think about it, the scarier it
seems."
"Then stop thinking about it," Margret casually insisted. "You're too
focused on the empty half of the glass. Sure, there will be an
adjustment period, but you've got me to help you through that, sweetie.
Once you come through the other end of the transition, think about how
great our marriage will be. Like I said before, it'll be a dream come
true for both of us. You're emotionally stronger than you realize,
girl."
"Girl..." I whispered to myself. Margret took my hands and pulled me up
to sit. She hugged me from behind, and leaned her head over my shoulder.
"Yes, MY girl. So, it's been decided... if you marry me, you'll quit
your job, live as a woman for the rest of your life, and be my adorable
(and obedient) little housewife. The only real question is, will you
marry me, Roberta? Please say 'Yes.' Please make my life complete.
Please make me the happiest woman on Earth."
I turned to face her. "Yes. YES! I'll be your wife! I trust you,
Margret. I'm willing to place all of my faith in you, and I trust you to
decide what's best for both of us. I'll marry you, and I'll proudly be
Mrs. Roberta Montgomery!" I was sobbing at this point.
"Oh, sweetie!" Moved by my act of faith, Margret started sobbing, too.
She spun me around and kissed me all over my face, then she held me in
her arms, patted my head, and stroked my hair. I was trembling as she
laid us both back down and proceeded to make love to me. This time, she
was slow and gentle, comforting and caring. She caressed me with her
hands, her lips, and her tongue. I tried to respond, but feeling
physically weak and emotionally exhausted, I managed to contribute only
an occasional kiss. A wave of submissiveness overtook me, and I cried
tears of joy. Margret was in total control, and she magically wiped away
both my irrational fears and my practical concerns. By permanently
placing myself in her hands, knowing that I would be following my
lover's lead for the rest of my life, I finally felt safe and secure
regarding our future.
Cheryl
- 11.05.2022
- 23
- 0
Roberta Montgomery Part 3
- 3 years ago
- 25
- 0
Roberta and CousinsChapter 2
- 4 years ago
- 27
- 0
