Looks by Missy

Looks by Missy
I had met him several times before, and now that he and his new wife,
June, had moved into our neighborhood, we interacted more frequently. I
had actually dated her for a while before she and Jeff married, so I was
aware of more intimate aspects of her as well as their relationship. I
had always found it strange that they got married, as they seemed an odd
pair. He was not particularly attractive, nor personable. Also, June
complained a lot about him, in particular his tendency to be rude to her
and her friends, as well as flirtatious with other women. In fact, she
stopped dating me to be with him, but as we started tapering off June
introduced me to one of her friends from college, Susan; setting us up
on a blind date that went well. It went so well, that we continued to
date, became serious, and then got married. June and Susan remained good
friends, requiring we interact as couples. Recently, June had asked
Susan if they could borrow a folding table from us and after using it,
she called about returning it. I told them to come on over. Although it
had been in the past and we were both married now, I still found her
attractive and had to admit, I would agree to do things for her just so
I could spend time with her. That was particularly true now, since it
had been months since we had been together, because our work schedules
had been so hectic.

To say I was disappointed when I saw their van pull up and only Jeff was
inside was an understatement. But I was friendly and helped him get the
table out of his vehicle and into our garage. As we did so, I couldn’t
help but notice the way he looked at me, a sort of combination of a
sneer, amusement, and ogling. It made me feel both uncomfortable and
awkward. I knew my appearance had changed a lot lately. I had let my
hair grow out, so it was now down to my shoulders. Susan hadn’t liked it
but insisted if I was going to wear it long, that I take care of it and
that included covering the gray that was creeping in. Maybe that was
what caught his attention, as my hair was now a light honey blonde color
and was shiny and smooth from the hair products Susan gave me. I had it
pulled back in a loose ponytail with a tortoise-shell clip, a feminine
look but one I used around the house a lot. I had also lost a lot of
weight, a conscious effort to slim down, dropping nearly 25 pounds in
the last three months. So I no longer had the pudgy belly that Jeff was
used to seeing. My waist was now a trim 28 inches, but unfortunately the
lost weight didn’t include my chest. As a teenager, I had a bout of
gynecomastia which when combined with my weight gave me a definite
protruding set of ‘male boobs’. When I also had a large stomach, it
wasn’t as noticeable as I looked like any other fat guy. But now my bust
was more prominent, projecting out from my smooth trunk. I hadn’t
thought about how they might look under my loose t-shirt, bouncing as we
moved the table. So maybe that was what caught his eye. In any case, he
left and I went back to doing my chores around the house. I forgot all
about it until a few days later when June called.

“Hello Roger, how’s it going? Sorry I missed you the other day, it seems
like forever since we’ve been together. Jeff mentioned that you looked
so different. That you are much trimmer and your hair looked nicer too.
I wanted to come by and give you guys a thank you gift, is now a good

“That’s nice June, but you don’t need to do that. Besides, Susan isn’t

“Well I want to give you something. I don’t mind that Susan is not at
home. I’ll be over in a few minutes.”

She hung up and I was left standing there. I had tried to deflect her,
as she really didn’t need to reward us for loaning her the table, but I
would be glad to see her. I just didn’t want to sound too eager. Soon, I
heard a knock at the front door and I opened it to let her in. Standing
there, June looked great as always. Her soft brown hair was cut in a
short style that framed her face perfectly. She had just enough makeup
to highlight her bright blue eyes, high cheeks, and full lips. The cut
of her top, a white sleeveless mock turtleneck in a sheer fabric,
emphasized her large breasts. The lace bra she wore underneath was
visible and you could tell she was a D- or even DD-cup. The rest of her
outfit was a simple pair of jean short-shorts paired with high heel
sandals. Maybe because she was only about 5’3″ in height, but she almost
always wore heels. The fact that they made her ass look good too, was
also a plus, I’m sure. Seeing me, she smiled and reached out to lightly
grab my upper arm.

“Oh my! Jeff is so right. Your hair is lovely. I hadn’t realized it had
gotten so long and that color is suited perfectly to your skin tone and
hazel eyes. I can see why he was so struck by it. I also have to admit
your weight loss is very noticeable as well. Not that you were fat, but
without that typical male paunch like Jeff’s, you look years younger and
so trim. He told me you seemed to have developed up top as well. I can
see what he meant, although if I remember correctly, when we were
together you had a bit of that already, didn’t you?”

Her barrage of compliments and then questions about my appearance caught
me off-guard. Especially about my chest. I had gotten somewhat used to
it being atypical and most people didn’t mention it if they noticed. I
blushed and stuttered out something about it being a condition I had
since puberty. She quickly agreed that I was probably the same size as
before, but it just looked different with a trim waistline. As we
talked, she moved closer and I caught a whiff of perfume. I recognized
it immediately as it was a fragrance she wore when we had dated. I
hadn’t smelled it on her since she and Jeff married. The mere smell
bought back pleasant memories of our time together and put me in a
better mood. But June soon went back to my hair.

“Jeff told me, that he thought your hair was as pretty as any woman’s
and I agree. I would love to do something with it once, just for fun.
You know, he has been pestering me constantly about it. He’d love to see
how you would look with your hair done and maybe wearing something up
top that would show off your bust. I can see what he means now. I could
really work something out I think. How about it, would you do me a favor
and let me try? If you don’t, I know Jeff won’t give me a rest. He can
be so annoying about things he wants.”

I wasn’t quite sure I understood what she was asking, so I questioned

“What do you mean try something? Try what?”

“Oh just let me style your hair. You know, put some curl in it or maybe
some soft waves with a flip. That will be the hard part, deciding what
style might look best. I can already imagine four or five looks that
would be perfect for your hair and face. I could do even more, if we had
it cut right. Then if you wore some cute top or something that would
show off your bust, I think that would do the trick for Jeff.”

“What? You must be joking. I wouldn’t do something like that. Even if
agreed, Susan would think it would be silly too.”

“Susan’s fine with the idea. As soon as Jeff got home the other night he
started on me, so I called her to talk about it. She said it was okay
and acted like it wouldn’t be a big deal at all to her. Besides it would
just be us, a one-time thing you know. I’m sure you realize what a hound
Jeff is about boobs. He can’t seem to get enough of them.”

Although I was startled first by the idea itself, the fact that Susan
had agreed really put me off balance. I stuttered around trying to
figure out what to say. I seized on her last statements about how Jeff
like boobs.

“Well if Jeff is such a breast guy, why would he be interested in me? I
may be unusually large for a guy, but compared to women, especially
someone like you with your figure, I would look like a board. There’s
really not much there. Plus I’m a guy. The idea is just too strange.”

“I agree you’re not like me or even your lovely wife, but you
underestimate Jeff’s range of interest. He’s as hot for small boobs as
big ones really. In fact, he seems to get fascinated as much by someone
with ones different than my size. That’s what I like about this idea. I
mean, I know it is just a form of visual stimulation and since you’re a
guy, looking is all he’d want. I know it might seem pretty odd, but for
me I’d like the chance to do this. For one thing, I really enjoy being
together, just you and me. If we were to do it, you could come over to
our house, and we’d spend the day together. Try different looks, have
lunch, just be close. Ideally, if you would agree to Saturday, that
would be perfect. Jeff has to work till 4 PM, and we could have all day
to hang out, just the two of us. Then he could come check out how you
look. I’m sure once he got a few looks, he’d be satisfied. Please think
about it. I’d make it fun I promise. I just don’t think I can take more
pressure from Jeff about this.”

As she spoke, June moved even closer. So close that her bare leg rubbed
against mine and her breasts were literally brushing my shirt. The heady
aroma of her perfume filled my brain and I felt like I was in a fog. The
mere idea of trying to dress to look like a woman was so outlandish as
to be ridiculous. I knew I was not overly masculine, with neither big
muscles nor lots of body hair, but even with a modest 5’8″ frame, I did
not think I had a feminine profile. Plus, the way Jeff looked at me in
the garage was creepy enough. This would be way worse. But then the idea
of spending all day with June, just us two was a big draw. I mean I had
gotten hard as soon as she arrived and now it seemed like it was going
to explode. I had a serious crush on her and still consider the night we
went to bed together to be one of the high points of my life. Even my
subpar sexual performance didn’t alter how I looked at that night. So I
stuttered a second, trying to think of what to do. June must have sensed
my indecision, as she stared at me deeply before leaning in to kiss my
cheek. Her boobs pressed against my arm and it seemed like her perfume
was swirling around me. Staying close to my face she whispered again.

“Please say yes. I need your help, okay?”

That pushed me over the edge. Although I couldn’t voice it, I managed to
nod my head in the affirmative. Getting the response she wanted, she
grabbed me in a big hug and again kissed my cheek. I could feel my face
flush from embarrassment, as I was sure she felt my erection as we were
pressed together. Finally she let me go and stepped back. As if by
magic, she pulled a cloth tape measure from her pocket. Stepping behind
me, she looped it around me, and quickly measured around a few places on
my frame. Finally satisfied, she rolled it back up and moved in front of

“This should give me enough to work with, I mean for what he wants. I
promise you won’t regret this at all. Just come over about 10 on
Saturday morning so we can get started. No need to dress up either, a
tee shirt and jeans will be fine. Thanks again, I knew I could count on
you to be there for me.”

As she headed back to her car, I began to realize what I had agreed to
do and started to panic. But seeing her smile so big, with relief
obvious on her face, made me swallow my protests. Plus her nipples were
hard and poking through her top, suggesting to me that she was excited
too. I would just have to do it, get it over with, and forget it. It
seemed a small price to pay to have time alone with her. Later when
Susan came home, I thought of telling her but before I could say
anything she matter-of-factly mentioned that she had plans to shop on
Saturday, would be gone all day, and that I should find something to
keep me busy. She had a knowing smile as she talked, which told me she
had spoken with June and was apparently okay with it all. The next two
days were crazy as I alternated between excitement about being with June
and dread at what I had agreed to do. The visual of Jeff leering at me,
haunted my thoughts about the day, but I tried to balance that with
knowing I could be close to June.

Finally, it was time. I took a quick shower and shaved my face. I was so
nervous, I could only eat a slice of toast. Susan was prepping for her
day and as she left she told me to have fun, behave, and she would see
me later for dinner. I headed over to June’s house, dressed as she
suggested in jeans and a tee. When she opened the door, I was
immediately glad I had agreed to do this for her. She was wearing a sexy
romper with cutouts on the sides and a deep v-neckline revealing lots of
cleavage. Her boobs were taut against the fabric and I could tell she
wasn’t wearing a bra. She gave me a big hug and a quick kiss on the
cheek. I started getting hard immediately as I smelled the perfume she
had worn for me before. Taking me by the hand she led me to the kitchen.

“Roger I am so glad you are here. We are going to have a wonderful day.
A day we will remember for a long time. But before we start getting you
ready, I want to just relax and chat. I’ve brewed up some tea and we can
talk and catch up on each other’s lives, okay?”

I followed her to the kitchen, where we sat at her table and talked for
the next 30 minutes sipping tea and just being with each other. It was
perhaps the most we had talked and the closest we had been since we
stopped dating. I loved it, as she was both interested in me and flirty
as well. It was hard not to just stare at that wonderful cleavage. That
kept me hard as well as interested, as my cock seemed to like being
close to her even more than my mind did. Even when she described how
excited Jeff was about today, it did little to dampen my growing
enthusiasm. I did have to ask how her marriage was and couldn’t resist
digging a bit to see what she had found so intriguing about him. I did
feel a bit awkward after I asked her, but she merely smiled and answered
my personal question.

“Jeff does have some disagreeable qualities and tends to annoy me at
times, but he has a few things that most women desire. Although he
doesn’t seem to be a smooth talker most of the time, especially in a
group, he is really skilled at it. When you’re alone with him, he has a
way of talking with you that makes you feel like you’re the sexiest,
most special woman in the world. He seems to know what buttons to push
to get you excited or feeling good about yourself. He also has a sort of
inner command that radiates confidence, control, and experience; that he
knows what he is doing at all times and will be there to protect and
provide for you. That is a sort of masculinity that a lot of women love.
That personality strength is combined with a physicality that is
special. Jeff isn’t the handsomest guy and in everyday situations he
doesn’t stand out. But I’ll tell you, in the bedroom arena, so to speak,
he shines. He has the right equipment you might say that puts him in
elite company. It’s a kind of sexual experience you can’t get from most
men. He does know he is special and that he can get his way with many
women, so you have to deal with his wandering, but that’s a price I was
willing to pay.”

I had to blush when she answered, because it immediately made me think
of our sexual encounter. I had finally lured her to bed and when she lay
naked before me I tried to make her as pleased sexually as I could. I
did give her multiple orgasms, but it was only by kissing and licking
her sweet pussy until she came. Unfortunately, when I moved up and began
to fuck her, I was so excited that I didn’t last but a few strokes. She
told me it was okay and we cuddled after I came. But that was the only
time we had sex and we only had one more date, although we’d get
together for lunch or other daytime activities. I had to know that I
didn’t really deliver the sexual excitement she wanted. So when she
described how Jeff was able to please her that answered my question in a
way I was not ready for. But that seemed to be the perfect transition
for her to indicate that it was time we started my transformation. I was
docile by that time and having resigned myself to do this, I went with
her upstairs to their master suite. Following her as she went upward,
my eyes gravitated to the bottom of her romper where her butt cheeks
were showing and I could see she had no more than a thong panty
underneath. Of course my cock was rock hard. As we entered the room, she
turned and gestured toward the bed.

“Go ahead and slip out of your clothes. Also put your hair up with the
clip I left on the nightstand. I want to see what I have to work with
and how much we need to do.”

I started to hesitate, but she waved me on, and then turned to go into
the adjoining bath. This was where my nerves kicked in. Swallowing and
trying to convince myself it would be fine, I pulled off my shirt and
then slid the pants down my legs. I pulled my hair back and twisted it
so the clip would keep it on top of my head. Standing there in my
underwear, I interlocked my fingers and held my hands just in front of
my still erect cock. I was trying to wish it to get soft, but with no
response. She returned and smiled again.

“I need everything off Roger. We don’t need to be coy, I mean we’ve seen
each other nude before, right?”

Glancing downward, her slight smile turned into a wide grin.

“Oh I understand now. That’s so cute, you still find me sexy.”

Moving closer, she put her hands on each side of my briefs and slowly
but steadily pulled them down. My cock hung in the fabric a second
before popping out and bobbing in the air while she pulled my briefs
down far enough for me to step out of them. I nearly jumped when she
wrapped her hand around it, lightly grasping the shaft.

“There’s my little fellow. Glad to see he’s still perky. I just love how
he fits so easily in my hand. Sometimes it feels like I can barely wrap
my fingers around Jeff, you know? I’m also pleased that I remembered how
you look. I was hoping that I was right that you didn’t have a lot of
body hair. It should be easier to make you presentable.”

Turning, she kept a light grip on me and pulled me toward the bath. I
was blushing furiously now, both from what she said as well as from her
actions. But what worried me most was her statement about my hair. I was
right to worry, as once we were in the room, she let go of me to turn on
the water in the claw-foot bathtub. She reached over and began to put on
some vinyl gloves that were on the counter.

“Roger go ahead and step in the tub. I’m going to apply some depilatory
crème to make your skin smooth and soft.”

“June, you didn’t mention anything like this. I don’t know if that is
something I want to do. I mean, I thought you just wanted me to let Jeff
look at my chest? Why do I need to remove my body hair?”

“Oh don’t worry, you have such fine hair, and it’s so light in color, no
one will really notice. But Jeff expects you to look feminine for him.
Besides, you do have a little patch of chest hair that is totally wrong
for the outfit I chose for you. This will only take about 15 minutes.
The crème is real effective, although so gentle you can use it to remove
pubic hair. You still remember how smooth I was for you when we had sex,
don’t you?”

By now June was applying the crème, as she had not waited for me to
agree. She had just started. I had to admit I didn’t have a lot of hair,
as it was only noticeable on my legs, forearms, the small patch in the
center of my chest, and under my arms. The thickest area was my pubic
hair and even that was so light it didn’t really hide anything. June
seemed oblivious to how this might affect me later, but as she smoothed
it over my body I couldn’t help but wonder how I would explain this to
Susan. I would have to tell her I had done it, as she would surely be
jealous if she knew I had allowed June to see me completely nude, not to
mention handle my cock. These thoughts tumbled in my head as June
finished by putting crème on the base of my cock, all over my balls and
between my cheeks. She did leave a narrow strip of hair above my cock
which immediately made me remember that was how she had looked when I
went down on her. Having completed the application, June peeled off her
gloves and told me to just stand there, it would only be about 15
minutes and she could wash me off.

That was the longest quarter hour of my life. I could see myself
reflected in the mirror over the sinks, and I couldn’t help but focus on
how feminine I looked in this situation. The shock of what I was doing
began to affect me and my hard-on quickly softened making everything
worse. As it shriveled up, it appeared so small. All I could think about
was that I was going to present my body as a female to another man. By
the time June re-entered the bath, I was almost shaking from the cold of
standing there nude, nerves, and embarrassment. If she noticed, June
didn’t say anything but picked up the hand-nozzle, a washcloth, and
immediately began to wipe and then wash the crème and the dissolved hair
off my legs. As she worked her way upward, she smiled at me.

“Time for the unveiling! I know you’re going to look so cute when I’m
done getting you ready. I hope you are as excited as I am, but honestly
I’m glad you’ve gone back to your tiny softness. It will make the rest
of the transition a lot easier.”

The shower of slightly cool water had been aimed right at my cock and
balls as she talked and when she moved it up to rinse off my stomach and
chest hair, I couldn’t help but see how small and powerless they looked.
It was almost as if my cock was reticent to be seen, as it had shrunk
back on itself. My balls were no better, being like almonds inside my
sack. When she finished rinsing the crème off my body, June told me to
sit on the edge of the tub so she could wash my hair. She went through
the process, first shampooing, then conditioning and lastly a final
rinse. After my hair drained a bit, she wrapped it up in a turban towel
to allow it to dry and handed me another bath towel to dry my body. As I
did so, I couldn’t get over how my appearance had changed by the simple
removal of body hair. I knew I wasn’t overly masculine but my soft,
smooth skin highlighted the feminine aspects of my appearance. It wasn’t
helped by how small my cock and balls looked without pubes; they still
seemed in shock over this whole episode. Once I was dry, I went to the
bedroom where June was waiting. Entering the room, I subconsciously
placed my hands in front of my genitals as if I instinctively knew that
had to look small and delicate. If June noticed she didn’t say but
merely indicated for me to stand in front of her. I noticed she was
holding a small tube and a spray can.

“Okay Roger, time for the next step. This may seem extreme, but I think
it will work for the best. Even though you are small for a man, your
cock still can disrupt the appearance we want for Jeff. So, what I’m
going to do is apply some medical adhesive to help cover it up. The good
thing is the adhesive is very gentle and non-toxic, plus it’s easy to
remove. Here let me show you how it works.”

June sprayed a little of the clear liquid on the forefinger and thumb of
her left hand. Pressing them together, they were immediately glued
tight. She had me pull slightly on them and I could tell that they would
not come apart without tearing the skin. June then put some liquid from
the bottle where they were stuck together. The liquid rapidly dissolved
the medical adhesive and her fingers separated easily. She smiled
broadly at me.

“See, it works like a charm. What I want to do is use this to help tuck
your male parts, so they are hidden. I think it should work well for
what we need. You’ll have to help but it should only take a few minutes
to complete. Just do as I say.”

“June, it looks safe, but this is too much. I mean, I really didn’t want
to remove my body hair, but I could kind of understand it. But why is it
necessary to glue me like this? Can’t I just push my cock back between
my legs?”

“Well that might help a little, but the panty I picked for you is fairly
sheer, so I just don’t want to take any chances on what might show. Tell
you what, let me try it and if you don’t see how it improves your new
look, then I’ll remove the glue.”

Not really convinced, I felt like I had no other choice, so I let her
proceed. It went pretty easily, I had to admit, although it felt odd to
have her handle me so much. We first worked on keeping my balls inside
of me; I pushed them one at a time into the cavity on each side while
she pulled back my sack skin and glued it tight against my body. She
only had to hold it a minute or two to allow the glue to set. The balls
protruded a little against my taut skin, but mostly stayed concealed.
June finished by spraying the underside of my cock, avoiding the more
sensitive skin on the glans, and then stretched it back toward my ass.
Since it was pulled tightly backwards, she held it for a good five
minutes to be sure the glue was firm. Releasing her hand, my cock stayed
in place, making it feel quite weird between my legs. From the front, I
now had a smooth curve running from my narrow patch of pubic hair down
between my legs. It didn’t really look like a woman’s labia but it
looked even less like a man’s genitals. June was very pleased. Seeing
how she had solved that issue, she had me slip on the panties she had
chosen. They were a cheeky tanga style made of a sheer beige nylon with
lace trim around the waist, legs and up the cheeks. I understood what
she meant now, as I looked very feminine from the front with the pubic
landing strip and flat front providing a convincing look.

“Oh Roger that looks so much better, better than I had even hoped. I
guess I had forgotten how small you really were. That made it much
easier to convert you to a smooth sexy look under your panties. Now we
need to work on your hair. Just slip on this robe and sit down at my
vanity. I’m going to use rollers to give you the curl and wave I want in
your hairstyle. Once your hair is in curlers, then we can take a break
for lunch. Later I can do your makeup and we can finish getting you
dressed. We should have lots of time before we show you off to Jeff.”

That short conversation sort of summed up my relationship with June. She
could praise me and insult me within the same sentence. Despite all the
changes she had done to my appearance, I enjoyed being with her. I
hadn’t spent this much time with her, or been this close since we
stopped dating. Just having her hold my cock, even if it was to glue it
out of the way, gave me a special feeling inside. Of course, my thoughts
also flashed to my wife and I felt a tinge of guilt at still lusting for
June, but I convinced myself that Susan was okay with me being here.
Overall, I was beginning to adjust to following June’s lead and doing as
she said. You could tell that she was used to setting hair, because it
took her only about 15 minutes to roll mine in large plastic curlers.
She used setting gel on each one and secured them with bobby pins so
they would stay in place. Once she had all my hair done, June covered it
with a stretchy hair bonnet. She seemed really pleased and assured me
that my hair would looked really nice once she styled it. We would need
to let my hair dry naturally for a while and then I could sit under her
portable hair dryer to finish it.

Taking my hand in hers, June began to file my fingernails. She wanted to
polish my nails, telling me she wished we had gone to a nail salon
first. I would look much cuter with nail extensions, but she could at
least shape them and give them a pretty color. June worked quickly,
doing first my right and then left hands. While the bright red polish
dried, she repeated her work on my toenails, even buffing my feet to
make them smoother. I questioned her a bit about removing the polish
when we were done, but she said it would only take a few minutes to
remove it. After Jeff had seen me, she would remove the glue, polish,
and I could take a quick shower so that I was free of all traces of her
feminization efforts. That made me feel a little more comfortable with
how far she was going with all of this. Once the polish was done, I sat
there waiting for it to get dry enough for me to move around. Sitting
there, I could see my image in her vanity mirror. I appeared as feminine
as could be with my hair in curlers, polished nails, smooth hairless
skin and light pink satin robe. Although I was loving being so close to
her, I was paying a high price for June’s attentions. While we waited,
we talked about how my marriage to Susan was going and exchanged
intimate details about each other’s love lives. The more we talked the
closer I felt we were getting. Maybe it was just coincidental, but she
made a lot of contact with me as we talked, letting her fingers trace
over much of my body and face or occasionally brushing against me with
her breasts or hips. Finally, she felt my nails were dry enough and
pulled out a pair of high-heel slippers. She wanted me to wear them so I
could practice walking in heels. They felt really odd as they shifted my
whole body posture, but combined with the other unique feelings of my
tucked genitals and the tight pull of the rollers on my hair, it didn’t
seem out of place. I followed her gingerly downstairs to get something
to eat.

We spent the next hour in her kitchen, snacking on a tray of fruits,
vegetables, and cheeses, while we sipped a glass of white wine. June was
so bubbly about all of this, it made me more relaxed. She emphasized how
much she appreciated me doing this for Jeff, since it would keep him
from lusting after some other woman. That theme had surfaced several
times as we had talked through the day, giving me the feeling that his
womanizing ways had made her doubt her own self-worth and
attractiveness. So I took special pains to compliment her on her
appearance, sexiness and style. She didn’t quite seem to get how much I
was drawn to her, as she constantly reflected my comments back to me;
she assured me I would look spectacular once she had finished my
transformation. For example, she insisted I walk back and forth in the
heels, while she gave me pointers on a sexy walk. June praised me for
being such a quick study and said I had a naturally sexy twitch when I
moved in my heels. Not exactly what I was going for, but I did enjoy our
intimate conversations. The most embarrassing point was when I needed to
pee. The wine had worked its way through me and I excused myself to go
to the bathroom. Of course, I had to sit on the toilet, and the way it
felt when I peed, was surprisingly natural. It only reinforced how
feminine I was becoming in both actions and image. Finally, it was
nearly two o’clock and she said it was time to get ready. With a fair
amount of trepidation, I finished my wine and we went upstairs.

The first step was for me to sit for about 10 minutes under her portable
hair dryer. It finished drying my hair while June got ready to do my
makeup. Once she turned off the dryer, she had me sit at her vanity and
began the process. I expressed my reservations again, and asked her if
we could just do the minimum necessary. Her laugh, a lilting, teasing
chuckle, told me that she would have none of that. For the next 30
minutes, she worked her magic on me starting with foundation and
finishing with thick false eyelashes and glossy red lipstick. I could
see the transformation in her mirror and was stunned both by how much
detail she took with each step and how successful she was in crafting a
female appearance to my face. When she lightly stroked a shiny lip gloss
on my blood red lips, I wanted to cringe. I no longer looked like a man
and could only imagine how Jeff would see me. Of course, June was
overjoyed, telling me I was much cuter than she had ever hoped for. With
my face done, she had me shed the robe and stand in front of her.
Smiling she picked up some brownish red lip color.

“Now Roger, you may have the cute little breasts that Jeff is seeking,
but your nipples and areolas still look like a boys’. So I’m going to
use a little lip stain to give you some more size and darker color.
Although this is a stain, we need to let it dry a bit before we dress
you. But I assure you, Jeff will love your new look.”

Using a narrow makeup brush, June carefully worked on each nipple. With
small strokes, she doubled the size of my areolas and made them much
darker. When she had applied enough, she had me turn to look at my new
boobs in the mirror. The effect was sobering; they now looked much more
feminine with this small step resulting in a big change in appearance.
June had to compliment me and tease me a bit at how cute my boobs were
while we waited for the stain to dry. Once she felt the color was set,
she indicated it was time to put them in my first bra. June took a beige
bra, trimmed in lace with sheer cups and fitted it around my chest. As
she adjusted the shoulder straps and lifted my small boobs on top of the
push-up pads at the bottom of each cup, I blushed a bright red visible
even through my new makeup. I was flabbergasted by how much cleavage she
had created and it was even worse, because my enhanced areolas were
visible through the sheer lace at the top of the bra cups. She was
beside herself, telling me I had a killer body. It was hard to argue at
that point, as my chest was very prominent while my panties were smooth
with no sign of a cock. I was now regretting my decision to go along
with this. Maybe it wasn’t too late to back out.

“June, I’m having second thoughts about this. I mean, I didn’t expect to
have to go this far and you’ve done such a good job that I am nervous
about Jeff seeing me like this. How can he look at me as a man after he
sees how feminine you have portrayed me? I thought I was just going to
have to wear a girl’s top or some sort of lingerie camisole, but you’ve
totally redesigned my whole image. It feels unnatural to have my
manhood glued down as if it doesn’t exist and the way you’ve highlighted
my chest plays on my sensitivity about how it looks. Plus, I can’t
imagine that Susan thought you would take me this far. If she saw me
now, I’m sure she would want me to stop as well. I’m sure she wouldn’t
want her husband to look like a woman. I should have said more about my
concerns earlier, but I think it’s time I put my foot down.”

I tried to look stern and determined as I finished, but I felt nothing
but fear of my upcoming humiliation. My insides felt like they were
being squeezed, with stomach in knots and my chest compressed tightly. I
was acutely aware of my cleavage and uplifted breasts as I breathed;
they rose and fell with each breath which were now coming faster as I
began to get more and more nervous. It was even worse because you could
see my enhanced nipples peeking through the lace. My cock seemed to be
crying out for help, as it was pressed tightly against me, snugly
trapped between my legs, covered in silky nylon. I sensed it was not how
I should look or be dressed. I had been so overcome by my desire to
spend one-on-one time with June that I had overlooked how much I was
sacrificing. Finally I had to look down at my hands, as I was getting so
upset I was afraid I would cry. They were folded across my body, arms
pushing my padded breasts further forward. I had them resting at the top
of my panty, the shiny red nails making my fingers look longer and
thinner. I couldn’t help but see how my fingers were trembling, my
resolve fading as I hoped that June would allow me to escape this
torment. I could sense her moving closer and glanced upward, my thick
lashes partially shading my eyes as she looked at me. She took my hands
in hers, lightly squeezing them as if to give me the strength to stop
shaking. My lower lip quivered as I waited for her response.

“Oh Roger, you are so adorable. I figured you might have doubts about
this as we got closer to making it real. But don’t worry, you look
fantastic, so sexy yet vulnerable and demure. Jeff will go crazy over
you. I mean, you’re like a virginal sex goddess. This will be more than
he ever expected. As far as how he will see you in the future, I bet
he’ll have a new found appreciation of your potential. I have to admit,
he has always teased me about the fact that we dated and how you aren’t
the kind of man I needed. But I’m sure once he sees you as a beautiful,
sexy woman, he’ll understand what I found appealing about you. Susan
will have the same reaction, too. Bet you didn’t know she had a hot
lesbian fling with one of her sorority sisters when she was in college,
did you? If she saw you like this, she’d eat you alive. I know she’s
bragged to me before about how good you are with your lips and tongue. I
know you were the best pussy licker I ever had and to be truthful, I
miss that now, as Roger is not the kind of guy to do that for his women.
So just try to relax, have fun and enjoy the moment. I guarantee once
Jeff starts drooling over you, you’ll forget your worries and realize
what you are capable of.”

She gave me a big hug and a kiss on the cheek. Earlier, I would have
been thrilled to be this close to June, but looking down all I could see
was how her breasts were pushed up against mine, accentuating both our
cleavages. That was not how I wanted it. Plus rather than be reassuring,
her little speech made my mind reel. Not only imagining Jeff ‘drooling’
over me but the idea that my wife had a lesbian past. I thought I knew
all her inner secrets. If she had gone that far, what else had she done
or was still doing that I didn’t have a clue about? At least this last
worry got my mind off my catwalk for Jeff. I had decided if I went
through with this, it would be a brief walk around so he could see me
and then I would retreat and change back to my own attire. June had been
very clear that I could stop at any point. So with that small plan in
mind, I let her continue the last phases of my transformation.

Getting fully dressed didn’t take much time. June gave me a pair of
fishnet thigh-hi stockings in a light beige with lace trim on the
elastic at the top. She showed me how to bunch them up and slowly work
them up each leg. I had to admit the feel of the silky material on my
now smooth legs gave me a sexual rush. My cock twitched even as it was
held in place between my legs by the medical adhesive. The stockings
went almost to my panty, giving me a much longer leaner look. June had
me slip on the dress she had selected and helped me by zipping up the
back. It was a simple sundress with spaghetti straps, triangular cups
for the top, and a baby-doll style that extended just past the top of my
hose. The cups covered my bra cups, but left the straps exposed and
highlighted the padded cleavage. It was a cream white, with eyelet
details on the cups, around the hem, and under the bust. I was a bit
surprised at this choice because it was a relaxed style. With my dress
on, she had me fastened my shoes, a pair of strappy high heel sandals in
a nude color. Once I was fully dressed she had me walk around a bit and
I could see that I looked quite feminine in the outfit and although it
was very short, the dress still kept my stocking tops covered most of
the time.

Now that I was dressed, June turned to styling my hair. She slowly
unwound each roller, letting the resulting softly curled hair bounce
toward my shoulders. With each one, I saw more and more how curling my
hair would finalize the change of my overall image. Once she had then
all removed, she lightly tousled my hair with her fingers, separating
the curls only a bit to make then a little looser. She also used a hair
pick to position them, but she made it clear that my hair style would be
very curly. Satisfied that she had it the way she wanted, June used hair
spray to help the curls maintain their shape. She was very excited, as
Jeff loved curly hair. I had to admit, looking at my image in the
mirror, I could see why she was excited. I had the look of a real
female. Enough to make me resume my worries about how Jeff would think
of me going forward. As my mind focused on my upcoming debut, she gave
me some jewelry accessories, including a necklace, bracelet, anklet and
clip on earrings, all in a silver-rhinestone theme. The last piece of
jewelry made me blush again. It was a solitaire-style ring with a single
large rhinestone simulating a diamond. She slid it up my left ring
finger against my silver wedding band, giving me the appearance of a
married woman. Her final act was to spray me with perfume. I recognized
it right away as the perfume she used to wear when we dated and glanced
up at her. June sensed my question.

“Yes, I used to wear this for you, but now I only use it occasionally.
Jeff calls it my ‘please fuck me’ perfume, because I use it to signal
him when I’m horny. He’ll flip when he smells it on you, as he will get
the impression that you want him. I’m making sure that we’ve pushed all
his buttons. He’ll think of you as all female in every way: sight,
smell, sound, and touch. Just remember how women react with you, and
mimic those moves and you’ll be fine. I know you look all girl to me.”

With that she gave me a quick hug, then told me to go downstairs that
Jeff would be here any minute. As I negotiated the stairs in my heels,
my mind was numb. Her description of how I should approach him confirmed
my worst fears. The five minutes waiting for her to join me were
torture, as I was worried he would come in first. I felt the need for
her presence to support me. Luckily, she came down and we went in to the
kitchen, just as I heard his car pull into the garage. The sound of the
garage door sent my heart racing and I felt light-headed as if I were
going to pass out. June sensed my nervousness and took my hands in hers
and squeezed them.

“Now just relax, you look wonderful. Jeff is going to be overwhelmed by
your appearance. I think once you see how taken he is with your new
look, that you’ll calm down and enjoy the experience. You’re lucky in a
way, because most guys never get to feel what a woman feels when she is
noticed by a man. I can guarantee that Jeff will make you feel totally
beautiful, sexy, and desirable. Remember to treat him with respect,
answer his questions and do as he asks. Jeff is forceful, especially if
he is attracted to you, but his demeanor is positive if he gets his way.
That strength and confidence in a man, is what a lot of women look for
in a guy and Jeff certainly will ease your sense of vulnerability with
his strength.”

She finished with another hug and a light kiss on my cheek. Despite her
assurances, I began to tremble and my head was still spinning. I knew I
no longer looked like a man. My masculine shortcomings and feminine
tendencies, like my flabby chest and longer hair, were emphasized so
much that I had to look like a total wuss to him. How could I have let
June talk me into this? Why had I agreed to sacrifice my masculinity,
just to please Jeff? I mean, I didn’t even like the guy and had little
respect for him because of how he treated June. I just wanted to curl
up and die, but June was whispering in my ear that I was to wait in
here, until she called for me to join them in the living room. She left
to greet her husband as we heard him shut the door from the garage and
make his way into the house. Standing there alone, I resolved to never
allow this to happen again. I was going to walk out there, let him have
his looks, and then ask her to help me change back. I realized I had
gone too far down this path and I needed to stop it now. If I lingered
this way, dressed like a needy girl seeking attention, then I may never
be able to regain my male identity in front of him. I would get June to
promise to never tell Susan the details of this and to never bring it up
around Jeff or her. As I built this wall of containment to convince
myself that this event would not change my future, I heard her tell me
to come join them.

With the sounds of my pounding heart echoing in my ears, I took my first
steps from the kitchen, concentrating on my short stride so I wouldn’t
wobble in my high heels. Beginning to turn the corner into the living
room, I felt a sudden coolness swirl around the bottom of my skirt,
chilling the small gap of bare skin between my panty and the lace top of
my stockings. It felt like an omen of bad things ahead, but all I could
do is reflexive pull down the hem of my dress, attempting in vain to
make it longer so my legs would not be so exposed. As I pulled I could
see that motion unintentionally exposed more of my upper chest, giving a
hint of the lace detailing on my bra cups. Focused as I was on my
clothing, I barely noticed Jeff and June sitting on the couch. It was
only when I heard the click and accompanying flash of the camera in her
smart phone did I really look at them. That was followed by several more
photos in quick succession, documenting my approach. June was perched on
the couch arm, close to Jeff who had sat down there. His grinning face
sickened my stomach immediately, making me wish I were dead. June was
looking at her phone, glancing my way in between photos. I really began
to panic now.

“June don’t take my picture. I want this to remain our secret. There’s
no need for photos of this.”

“Don’t be silly, you look lovely. Besides, Susan’s been pestering me all
day about how you look. We’ve been texting back and forth, and I’ve
given her lots of details to her questions but I delayed sending her a
photo until you were all done.”

“Yes don’t be shy, little one, you look great. I must admit I was right
to assume that June could take the raw material I saw in you and produce
a sexy vixen. Honey you’ve done a fantastic job with him. I wouldn’t
think he was anything but a woman if I didn’t know the truth. How’d you
convince him to go so far? I mean I just wanted to see what his little
boobs looked like, but you made him a regular sex doll. By the way, did
you give him a new name to fit his new look?”

“Yes, Susan suggested we use her old lover’s name, Roxanne. She felt it
would be appropriate for her hubby’s feminine alter ego since both of
them loved to give oral. I have to admit, he looks a lot like her too if
my memory serves me right. Both are blonde, small up top but sexy, with
long legs and a tight little ass. Did I meet your expectations with
Roxie’s new image?”

“Oh more than that, he or maybe we should just say she, looks so real
it’s unbelievable. I know she is cuter this way than before. But let’s
chill a bit, I could sure use a cold one. How about you bring us all
some drinks Roxanne? Then we can get to know each other better.”

I was left speechless by the turn of events, as more and more I felt
like a trapped a****l. Finding out that Susan was involved so heavily in
my transformation was gut-wrenching, plus the level to which Jeff found
me attractive was terrifying. I could see the lust in his eyes as he
spoke. I hurried back to the kitchen to get some drinks, happy for this
short reprieve. June had told me that Jeff would want a drink, so I knew
what beer to get and to pour white wine for her and myself. I really
wanted something stiffer than wine, but she had told me we wanted
something lady-like to start with. I put the drinks on a mirrored tray
and headed to the living room again. The break had been too short for
sure, although I had moved as slow as possible. When I returned, June
had sat in the chair next to the sofa, so I offered her the wine first,
then gave Jeff his beer and took my wine as I put the tray on the end
table. I glanced around the room, but the only seat options were next to
Jeff on the couch, or far across the room at a small writing desk with a
straight back chair. June could tell I didn’t want to sit next to Jeff
so she spoke up.

“Roxanne, why don’t you just stand in front of Jeff so he can take in
your whole image? The whole idea of this party was for you to show off
your cute figure to him and let him fully appreciate the hidden talents
he had noticed before. Do a slow twirl and then move closer to him.”

I swallowed about half my glass of wine as she spoke. I had made up my
mind to end this humiliation at this point and figured if I did as she
said, it would make a good breaking point. I felt ridiculous, turning
around on the balls of my feet to complete my twirl and I’m sure my face
was a bright red as it felt warm to me. Once I was facing Jeff again, I
felt this surge of fear wash across me. His eyes were intently focused
on my chest and glancing down I could see my rouged up nipples poking
through the sheer lace of my bra. I plunged ahead with my hasty plan and
leaned forward just a bit, so he could get a good look. I figured that
would meet all my obligations of my earlier promises.

“There you go. I did as you wanted as a favor for June, but now that
you’ve seen what you asked for, I think it is time to stop. Surely this
satisfied your desire to see my hair and body done up as a girl and I
gave you all the looks, and more, that you told June about. So June,
let’s go upstairs so I can start getting out of this stuff, okay? You
said whenever I was ready to let you know.”

Just as I was finishing, I felt Jeff put his hand on my leg, running it
up my stocking. I almost jumped as this was totally unexpected. I had
turned to look at June as I spoke as I figured my deal was with her. But
Jeff’s action caused me to look back at him. His face had a sneer to it,
making him look like a real life Snidely Whiplash. My heart was racing
now, as I was worried about whether he would allow me to leave and get
changed. I knew June did almost everything he asked, so I wasn’t sure
she would go along with my plan. The presence of his hand, lightly
gripping my thigh, highlighted this fear. I was about to speak up when I
heard June giggle a bit.

“Roxie, don’t be in such a hurry. You’ve not even let him see all your
pretty lingerie yet. When I told you that I would help you get changed,
it was with the understanding that Jeff said it was okay. This party is
really for him, don’t you know. You’ve barely been with him at all. Why
don’t you sit down next to him, so you two can get better acquainted? I
think once you relax, you’ll enjoy being a pretty girl.”

“Sit down here and relax. I promise I won’t bite, nibble maybe, but not

June chuckled again at Jeff’s weak joke, but I could tell that I
wouldn’t get any support from her, and he wasn’t relinquishing his grip
on my leg, so I nervously obeyed. I sat down, on the edge of the couch,
trying to maintain some distance from him. Because my skirt was so
short, I ran my free hand over my rear and then held the hem when I sat
down to be sure it covered as much of my legs as possible. I knew this
motion would make me look more feminine, but I felt I needed to do it.
Once I was on the couch, Jeff easily slid his arm around my waist and
pulled me closer toward him. His hand was wandering up and down my side,
going from my hip to my enhanced bust. This made me really feel awkward
as it seemed so creepy to be felt this way by a man. I nervously took a
big sip of wine, as I tried to calm myself. That seemed to catch Jeff’s
eye and he leaned in to whisper in my ear.

“I like the way you swallow. I love girls that can handle a big load
without choking. I must admit, I didn’t think June could deliver you
like this. When I saw you the other day I just knew you had an inner
girl that needed to come out. Now that you’ve released your feminine
side, I’ll be sure to make your experience a full blown one.”

As he finished, he took my ear lobe between his teeth and pulled
slightly. The whole episode made my body shiver and his last move
prompted goosebumps over my exposed skin. I felt sick inside, as his
insinuations as to my interest in being feminine struck to core of my
self-worth. Ever since June had proposed this idea to me, I had worried
about how I would be able to put it behind me. Now I knew Jeff would
never see me as a man again, and maybe June wouldn’t either. I just
wanted to end this as quickly as possible. Despite how it might look to
Jeff, I took another big swig of wine, emptying my glass. Watching me
finish my drink, he followed suit and emptied his beer. Smiling that
evil grin, he handed me his empty bottle.

“I think were both ready for a little more, don’t you Roxie? How about
you honey, you need a refill?”

“Sure, I can use some more. Why don’t you go back to the kitchen and get
us all another drink Roxanne?”

I obeyed June’s request and stood up to get more drinks. As I gathered
my tray and the empties, she stood up and came over behind me. Grabbing
the zipper at the back of dress, she slowly pulled it down and leaned in
to whisper.

“When you get to the kitchen, why don’t’ you go ahead and slip out of
this? I think Jeff would love to see you in just your pretty lingerie.
That way he can get a real taste of what you have to offer. I know he
loves it when I anticipate his needs. I’m sure he will feel the same
towards you. Just remember, pleasing him is the goal tonight, okay

I should have known it would come to this, but her actions blindsided
me. I could only nod my head and go to the kitchen. I refilled the wine
glasses and got Jeff another beer. I stood there a moment, feeling my
legs start to shake. The idea had seemed so innocent when June first
talked to me about it. Just the thought of being near her all day, had
clouded my judgement and helped me avoid thinking about what I was
really agreeing to do. But now, it was time. I slowly slipped the straps
off my shoulders and let the dress fall around my feet. Stepping out of
it gingerly so my heels wouldn’t catch, I reached down and picked it up.
I carefully folded it and put it on the table, taking my time so as to
delay the inevitable. I felt a shiver run up my spine, both from the
coolness of being half naked and the fear of what Jeff would do. I
adjusted my panty slightly and tugged on my stockings, making minute
changes as if they would provide better cover for me. I finished by
pulling up the cups of my bra to cover my nipples. I knew inside that
the sheer fabric of my bra and panties would hide little and I would
appear to be totally a woman. I had to reach between my legs to feel my
cock, hoping it had somehow worked free of the adhesive so I could
position it in front, as a sign of my masculinity. But it was
steadfastly attached, even as it had shrunk from the cool air and the
fear of my impending show for Jeff making it retract as much as the
adhesive would allow. It would be no help to me now. Taking a deep
breath and trying to steady myself, I turned and began the slow walk to
the living room. I focused on the tray, to be sure I didn’t spill
anything and to take my mind off how I would appear to him. It seemed
odd, but I walked smoothly now in my heels and noticed the soft sounds
of my stockings rubbing against each other and the change in the sound
of my stilettos as I moved from the tile floor of the kitchen to the
carpeted living room.

I avoided looking at Jeff, although I could hear a hiss of breath from
him as I came into the room. I went to June to give her the wine. Before
she had reached out for the glass, but this time she lay back forcing me
to bend forward to get it to her. I knew instinctively that this action
would push my ass out and give Jeff a bit of a show, but I saw no other
way. As I held the tray out for her, she moved her hands to my bra
rather than taking the drink. With a slight tug downward, she
repositioned it, so that my nipples were clearly visible through the
lace trim. She winked at me and mouthed “Don’t be shy” before she took
her glass. Now that I had served her, I had no other choice but to turn
and face Jeff. I walked to him and as with June, I reached the tray out
to him. He too hesitated to take his beer off the tray. I could see his
eyes widen as he looked up and down my body. Jeff took a moment to stare
at my breasts and then again at my crotch. I could only imagine what he
was thinking, but it had to be bad for me. Finally he reached out and
placed his hands on my hips, looking over at June. He smiled in that
creepy way I had seen before and slowly ran his hands back around my
panties until he could caress my butt cheeks. He gave them a soft
squeeze and then another. With a chuckle he looked up at me.

“Well this is a sweet surprise. I knew you had a woman’s tits, but a
plump woman’s ass as well is a nice bonus. Tell me Roxie, have you
always been this much of a girl, or did you come by it late in life? You
certainly look sexy in these panties. I imagine now that you see how hot
you look, you will want to wear them more often.”

I didn’t bother to answer his lewd question, as I could tell it was more
rhetorical than real. I was becoming super annoyed at this point, so I
pushed the tray forward even more to try to force him to take his beer
and remove his hands from my body. But he just looked up at me with that
sick grin. I could feel him move his hands back to the front of my
panties. He pulled out the front a bit, exposing my trimmed pubic hair.
Looking down the front of my panty, he had a questioning look on his
face. Releasing the fabric, he used his right hand to trace over the
panty feeling the flat surface below my pubes and following the smooth
curve down until his hand rested between my legs. Jeff lightly stroked
the shaft of my penis, still held tight against my body by the adhesive.
I shivered reflexively at this point, totally uncomfortable with his
sexual advances. As my body twitched he grinned widely and looked at me
eye to eye, while he continued to fondle me through the silky fabric of
my panty.

“Getting excited little girl? I know you girls pretend to be cool and
not as horny as men, but you really like it as much as we do. June you
told me he’d be small, but I had no idea he’d feel and look like a pussy
down there. What’d you do, cut it off?”

“Oh Jeff, don’t be silly. He just wanted to really look the part. So he
suggested we tuck it away and it just took a tiny bit of glue to hold it
all back. You like his new look?”

“Definitely, I mean he looks so fem already, this just makes sense. So
how well does the glue work? I mean, how long will it hold?”

“It’s good until we use the solvent to release it. The adhesive is a
high-grade medical brand that’s designed for extended applications.”

“That’s good, more or less permanent, or at least until she shows me
otherwise. As I said before honey, you done a wonderful job with her.
She looks and feels so real.”

Jeff had moved two of his fingers even further back so they rubbed
across the top of my cock head. This was too much and I squeezed my
thighs together tightly, so I trapped his hand in place. Jeff grinned
again and looked up at me as he wiggled his fingers.

“Am I making your pussy hot little girl? Don’t worry, I’ll take care of
you. I bet you’re getting wet too, huh?”

As he spoke he freed his hand from the pressure of my thighs and
continued to push back. I was mortified by his brazen actions and words.
But what was even worse, was that I knew how I had reacted to his touch.
Despite my embarrassment at being displayed to a man as a woman, the
mere stroking of my cock had caused a natural reaction. I had been
aroused all day by my interactions with June. Seeing her body, feeling
her touch, and imagining what could have been, these had all kept my
cock hard, or at least aroused even after she glued me down. So the
sensual movement of Jeff’s hand on my penis had caused it to leak the
pre-cum that had been just inside. To me it was a natural response, as I
had been doing it all day with June, but now as his fingers found the
wet spot in my panties, it looked like I was indeed turned on by him and
his fondling.

“Just like I thought, you love being a girl don’t you? I can tell you
love showing off and really want to please me don’t you? Otherwise, your
pussy wouldn’t be dripping wet when I touched you.”

Now I was getting mad. He was cocky and seemed to have no sense of
decency about touching me in such a personal area. I had been scared and
embarrassed by his attention, but this triggered a defensive response
from me, unfortunately I tripped over my words when I tried to set him

“Jeff stop that. My pussy is not wet because of you. I mean, my cock is
not wet. Aggh, whatever, I’ve just been leaking because it’s been such a
stressful day. I’ve just dressed this way because June asked me to
help. Having your hand down there is not acceptable and I want you to
stop. I agreed to let you have your looks, but not to be manhandled.”

I had tried to be firm and forceful, but when I realized I said pussy,
my voice cracked and I trembled a bit. I was more mortified now than
before I spoke up. Partly, because as soon as I stumbled over my words,
Jeff laughed and began to pinch my cock head harder. That made it even
worse because a little more pre-com leaked out as he did so. My panty
was so wet you could actually hear his fingers squish as he rubbed me.
Continuing to laugh, Jeff removed his hand from between my legs and
finally reached for the bottle on the tray, taking a quick slug of beer.
As he finished he put it on the side table and looked up at me.

“Whatever, cock, pussy, I guess there all the same when you’re built
like that. I love it. Roxie you are so cute, you’re driving me crazy.
But don’t worry I’ll respect you and realize that no means no. Just let
me get a closer look at those Grade-A tits of yours. Take your drink and
put down that tray.”

I did as he asked, grateful to have his hand off my cock, grabbing my
wine glass and placing the tray on the couch. I was still shaking and
mad. Mad at myself for flubbing my response to his groping and for even
agreeing to this whole thing in the first place. Mad at him for being so
damn smug and condescending. It irked me to no end the way he felt he
could just touch me anywhere he wanted. Even now, just the presence of
his left hand on my hip felt unnatural. I have never been interested in
men and now, despite being dressed like a woman, my desire remained
focused on women, like June and Susan. Jeff was just an annoyance,
highlighted by how vulnerable I felt being dressed only in girls’
underwear. I was ready to get this over with and change out of this
humiliating outfit. I noticed when I moved to place the tray on the
couch that Jeff shifted slightly, so his legs were together and centered
between mine. As I reached to place the tray and began to stand up
straight, I felt his hand shift toward my ass while he moved his other
one up so he could cup my left breast. I was now steaming mad; he was
continuing to fondle me in the most inappropriate places and I needed to
stop it.

But just as I was about to say something, he swiftly pulled my bra strap
off my shoulder, exposing my nipple. His eyes were focused on it, but he
smoothly pulled the strap forward while at the same time he pushed my
ass with his other hand. Those motions put me off balance and I began to
topple forward. Aware that I had a glass of wine in one hand, I focused
on keeping it steady so I wouldn’t spill it on June’s couch. At the same
time I glanced quickly down and realized I could place my knees on the
couch to steady myself. Unfortunately that put Jeff squarely between my
spread legs and let him lean forward to take my exposed breast into his
mouth, which he did. I was trapped with his hand holding my ass in
place, his lips sucking my breast into his mouth, and my knees
precariously balanced on the couch, leaving only the toes of my high
heels touching the floor. I gasped as soon as I felt Jeff’s mouth on my
breast, which turned into a squeal when he lightly bit my nipple and
sucked hard on it. I felt like I had touched an electric wire, as the
feel of his mouth on my breast shocked me throughout. I was also trapped
as I was off-balance but held teetering in place by his teeth lightly
grasping my hard nipple.

“Oh Jeff, what are you doing? I thought you understood I was just for
show. Please stop.”

My plea, in a high octave expressed between an even higher pitched
squeal and a breathy gasp, only caused him to chuckle lightly without
even releasing my nipple from the grip of his teeth. But he did move his
other hand, sliding over my cheek, down the crack until he once again
found the head of my trapped cock. Other than my shocked gasps, the
loudest sounds were the suckling noises he made as he tasted my breast
and the squishy noise of his thumb rubbing across my panty to stroke my
cock. He had placed his right hand on my waist so as to maximize control
of my body. I was limited in my defense to placing my free hand on his
shoulder in a pitiful attempt to push him off me. Behind me I could hear
June giggling. I must have made an embarrassing sight, since I straddled
across her husband as he devoured me. My face was blazing hot from the
humiliation of being in this position and I couldn’t imagine anything
worse. Until I heard the doorbell ring. I glanced over my shoulder in
fear, which escalated as June called out that the door was unlocked and
to come on in. I was panicking now, as the only thing worse than the
position I found myself in, was to have to face another person. Of
course, Jeff never wavered, but kept sucking my boob, and feeling my
crotch while he tightened his grip on my waist. I heard the steps of
someone enter the house, and close the door. I made another pitiful
attempt to push Jeff away, but he remained focused. As the steps drew
closer, my heartbeat raced and I glanced over that way again, trying to
figure out how to escape and find somewhere to hide. But it was too
late, the visitor came into the room. I about had a heart attack. It was
my wife.

“Oh my gosh, Susan, this is not what it looks like. Please believe me
this is not my fault or what I wanted. Thank goodness you are here to
help me. I can’t get him to stop.”

She didn’t respond, but stood and stared. The only sounds were the
squish of Jeff’s fingers in my wet crotch and the slurp from his kisses
on my boob. I finally had enough and took my free hand to push his face
off my chest and then grab his hand to pull it away from me.

“Jeff, just stop. Leave me alone. I’m not just a plaything, plus I’m
married for goodness sake.”

Having reclaimed my body, I turned toward my wife again to try to make
her understand. I carefully readjusted my bra, pulling up the strap so
my small breast was nestled in the cup, with the lace trim once again
partially covering my wet nipple. I also tugged down on the rear of my
panty, trying to free the fabric wedged between my cheeks by Jeff’s
fingers. The moves were both clearly feminine, as was the last one where
I pushed back my curled locks from where they had fallen across my eyes.
I was scared to death to have Susan see me this way, blushing both from
embarrassment at how I looked and from how forward Jeff had been. I
wanted to tell her how this day had gone so wrong, but I couldn’t figure
out where to start. Just when I was ready to speak, she beat me to it.

“Well Roxie this is just wonderful. It certainly looks clear to me
what’s going on. I mean you seem to be sitting all over my best friend’s
husband, letting him have his way with you. Not to mention, how cute
you’re dressed. Seems you’ve really embraced this role. I mean it looks
like you’re shaved all over, you hair is curled into a pretty hairdo
which goes perfectly with your new made-up face, and you’re practically
nude in those tiny panties and pushup bra. How could I not expect Jeff
to find you so desirable? Plus if I’m not mistaken, it sounded like you
were dripping wet between your legs as well. You’re not going to tell
me, that you aren’t enjoying his attention now are you? But don’t worry,
I know how persuasive Jeff can be and I understand how a hot little slut
like you would be eager to experience all he has to offer. I know I
certainly did. Well June, you were right about Roger. He seemed to have
embraced his new persona as Roxanne eagerly. She just looks perfect and
so adorable. When I walked in I was afraid I was too late and the party
had started without me.”

Her laugher rang out as she quickly hugged June and then to my
amazement, kissed her before leaning in to kiss Jeff. He was grinning
like a madman as they broke their kiss. Susan turned without hesitation
and gave me a hot kiss, our lipsticks sliding smoothly against each
other, as her tongue plunged into my mouth. I was totally confused now,
my head spinning from what was going on. As we kissed, she lightly
grabbed one of my breasts and squeezed it softly, moving her fingers to
tweak the nipple before releasing it. Finally she broke off the kiss and
looked down, as if mystified. She hesitantly ran her hand down the front
of my panty, obviously seeking the cock that should be there. Moving her
hand down until she lightly grasped the shaft of my cock, she smiled and
turned toward June.

“June you are a magician. Roxanne looks so believable. It’s like you’ve
turned my meek little boy of a husband into my dream lesbian partner.
You told me that he would be realistic and he is. I just can’t wait to
have my way with him at home, now that his real identity has been
exposed. But first, I want Jeff to finish what he has started. If Roxie
is going to be all girl from now on, then she needs to know what a man’s
cock feels like. We both know Jeff can deliver that and more.”

She turned back to me, while she put her hand further back between my
legs. Slowly she began to stroke my cock head, the light sounds of the
wetness apparent to everyone. Smiling, she leaned down as she took her
other hand to pull down my bra freeing the other boob. Kissing it and
then lightly sucking the nipple, she assumed the assault on me that Jeff
had started. This allowed him to unzip his pants and slide them down
slightly exposing his tented briefs. I was focused on Susan’s actions
but out of the corner of my eye, saw what Jeff was doing. I began to
panic now, which turned into full blown terror, once Susan stopped and
stepped back so that I was face to face with Jeff again. I glanced down
and involuntarily inhaled – he looked huge down there. I was still
trying to understand what all was happening to me, particularly the fact
that Susan seemed to be so pleased by my appearance and her suggestion
that she had been with June and Jeff before. The confusion must have
been apparent on my face, as June stood up and came to join our close
circle. She slid her romper off her shoulders, freeing her large bouncy
breasts that had captivated me for so long. While my eyes were now
focused on her, Susan took the glass of wine from my hand and moved it
so I could hold one of June’s boobs.

“Go on Roxanne, I know you’ve wanted these for a long time. June and I
decided that it was time to bring you in on our fun. Jeff had lusted for
you and wanted to make you part of his harem. So, when you eagerly
agreed to June’s request that you dress up for him, then we knew it was
time. You see, June and I have shared each other ever since college; I
just have a fondness for the female form. Since Jeff is always so horny,
it was natural that we eventually included him in our lovemaking. Once I
was properly fucked by his large cock, I knew I didn’t need your little
one that way anymore. What I did want from you, is your marvelous
lesbian kisses on my body. I just wanted to have you look more like my
old college flame. That fit perfectly with Jeff’s desire to have you as
his A-cup alternative. So this is just the start of a new life. From now
on, you will assume the role that suits you best; your looks will match
your real persona. Plus you can now please June like you do me, since
Jeff prefers to fuck rather than suck pussy. I’m sure once you’ve seen
what he can do, that you’ll realize that looks aren’t what makes a man,
but in your case, looks are what makes a girl.”

I glanced at both women totally stunned by what was happening. Then
realizing I had little choice I looked down at Jeff, his large cock lay
there slowly getting hard right before my eyes. I couldn’t believe how
big and menacing it appeared. I knew my cock looked nothing like this
and despite hearing that my wife had been fucked by it, I was more
worried about what it meant for me. June obviously saw my fears and
leaned to my ear, her bare breast resting on my shoulder.

“Go ahead and hold it. Once you feel it you’ll want to do more. It’s one
thing that’s actually bigger than it looks.”

I was shaking now, but knew what I had to do. As I looked again toward
his huge cock, I saw my reflection in the small mirrored tray on the
couch. What I saw made me realize that I was becoming just like I looked
like, my face, hair and body looked totally female. Closing my eyes, my
new image swirled in my brain reinforcing that my looks were now right
for who I would be. The idea that I would be able to lick, kiss, and
taste Susan’s lovely pussy again made me feel warm inside. Seeing how
the women had kissed, also made my trapped cock twitch with lust. I
could already imagine lying in bed with both of them, alternating my
kisses between each pussy. All I had to do now, was take the leap with
Jeff. Opening my eyes, I gazed at it again as it jutted upward,
twitching in the air as it waited for my touch. Being honest with
myself, I had to admit his cock looked magnificent, representing
masculinity far better than my little one did. With my mind made up, I
opened my mouth, ran my tongue over my lips tasting the lipstick and
preparing them to be stretched out by his size, and reached out to grab
onto it. As my small hands with their red polished nails, wrapped around
his cock, I could see how my looks now matched my true self and I was
ready to begin my new life.

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