I had seen her before at the bar. She was very pretty and a good
dancer. But that wasn't surprising. I came to the dance club so often,
I was bound to see anyone who showed up more than once or twice. After
my divorce, I had moped around a while. But finally, I got back on my
feet and started going out again. At first it was just for a drink or
two, then I actually started dancing. I had always loved to do it and
wasn't bad either. It was a little intimidating to ask a strange woman
if she wanted to dance. I mean the rejection rate was high. The good
thing it only took one or two to say yes. It wasn't like I was using
dancing to hit on women, although occasionally it led to a hookup. Most
nights though, I would dance a few hours, have a couple of drinks and
then go home. Because of my divorce, I wasn't quite ready for a
relationship anyway. This night, I saw her nursing her drink at the
bar. They had just started to play some good music, so I said why not
her?
"Hi, would you like to dance? Sounds like they're going with some good
tunes."
"Okay, sure. Let's go."
We danced about four fast songs. She was good on her feet, very nimble,
and seemed really in sync with the beat of the music. As they began to
play a slow song, I looked at her. Normally, I didn't do slow tunes,
especially with a new woman. I mean they were more for couples to get
close to each other, you know? So, I indicated I was going back to the
bar for a drink, but she took my hand and pulled me close. She molded
her body against mine as we moved slowly in time to the song. She moved
her head so she could whisper in my ear.
"I really like the way you dance. You move so well in tune to the
songs. Most guys don't have that kind of rhythm. You know I've seen you
here a lot and I always wondered why you didn't ask me to dance."
She let that hang in the air. I knew what she meant, I mean I was white
and she was black. So I wanted to clear that up.
"Well to be honest, you're such a good dancer, I didn't think you'd say
yes. I never had the nerve to ask before tonight."
"Well, I'm glad you did. I'm Eve by the way."
"Nice to meet you, I'm Donnie."
We danced another slow song and by the time it ended, I was a little
embarrassed. I was rock hard from the close presence of her body. So I
had to negotiate the walk to the bar a little carefully. I ordered us
drinks and we talked. I could sense she was a special person. It wasn't
just her good looks either. I really hadn't talked this much with any
woman I met at the club without going somewhere for sex later, but I
wasn't sure that was in the cards. I would love it, but still. Looking
at her she seemed out of my league.
Eve was about my height, slim body with a small bust but a wide round
ass. Her skin was a rich coffee color, her hair was a short Afro style,
and her eyes were big and beautiful with long lashes. She was dressed
in a nice tight pair of jeans with heels. She wore just the right
amount of makeup and her perfume was intoxicating. Overall she was
killer.
So despite how well everything seemed to be going, I had no illusions
about how my evening would end. We danced a couple more sets, ending
each one with one or two slow songs. We also drank a few more drinks,
more than I usually did. Finally, it was getting late. I was debating
what to do next, mentally settling on asking for a phone number. But
she beat me to it.
"Donnie, this is wonderful. I don't want it to end just yet. I hate to
be forward, but how about we go back to your place for a nightcap, or
something?'
The way she said it made it clear she wasn't after another drink.
Smiling, I said sure. I didn't live far from the club, and she told me
she'd follow me there. The drive seemed to take forever and I
constantly glanced in the rearview mirror to see if her car was still
there. At my place, I walked her to my apartment. Inside, I was
congratulating myself, not only on getting lucky with such a beautiful
woman, but because I had the foresight to clean up my place. I even had
fresh sheets on the bed. Once inside, Eve took over.
Quickly unbuttoning my shirt, and then starting on my pants, Eve left
no doubt what she had in mind. I followed suit as I steered her toward
my bedroom. We were both quickly undressed and I got my first good look
at her. She was even prettier naked than dressed. I was surprised by
her breasts, although small they were very perky with full nipples.
Even though Eve was in her thirties, she looked more like a teenager.
Her butt was wide and round, and she had trimmed, but not shaved her
pussy. She looked delicious. I continued to kiss her, and lightly cup
her breasts. She saw the condom on my nightstand and opened it,
stroking my cock as she put it on me. Then, after she lay back on the
bed, I took one of her boobs into my mouth, kissing and sucking it
until her nipple was hard. I then kissed her again.
I was going off the formula I always used with women. Although my ex-
wife had complained toward the end of our marriage that I made love the
same way every time, I knew for a new lady this wasn't a problem. We
kissed for a while and then I began the process.
I lightly kissed each breast, running my tongue over her nipples and
sucking them into my mouth. Then I planted kisses down the center of
her stomach, making my way down her body to her pussy. I knew most
women liked cunnilingus, so I'd spend some time to make them wet. I ran
my lips over hers, kissing and sucking the outer labia first and then
the innermost ones. Since Eve had trimmed hair, this was a bit more
work than if she were smooth, but I forged on. After a few minutes of
this, I sought out her clit. I took it between to lips and flicked it
with my tongue and then softly sucked on it. I knew for women this was
their most sensitive spot, so again, I spent a few minutes here. I
could already feel Eve wiggling, so I knew she was ready for my cock.
I stopped kissing her pussy, and moved to position myself fully between
her legs. Spread open, I mounted her, driving my cock into Eve's wet
pussy. I quickly began to fuck her, moving in and out. I knew I wasn't
the biggest guy, so when I plunged all the way inside her, I rotated my
pelvis against her. This should further stimulate her clit and help her
stay aroused. As I pounded her, my desires took over and I went faster
and faster. I was approaching climax now, and focused on finishing. I
could feel and hear her response, but I was on auto-pilot. Soon I felt
my body lock up as my orgasm swept over me. I shot come into Eve,
several times, my cock as far in as I could push it. Finally I
collapsed on her. She was still wiggling, and as I began to soften, Eve
reached down to fondle my cock. But she couldn't bring it back to life.
I could get erect several times in a row occasionally, but not when I'd
been drinking. So finally we just settled into each other's arms.
Just as I was about to fall asleep, I felt Eve move. She was getting
dressed. Looking over at me, she smiled.
"Donnie, I'd love to stay, but I got work tomorrow. Thanks for a
wonderful time."
She kissed me and then made her way out of the house. I was so spent, I
just fell back on the bed and was asleep in minutes. The next morning,
when I was having coffee, I realized I didn't have her phone number, or
even her last name. I really had a good time, and hoped maybe I'd see
her again at the club. But as the week dragged on, I started having
doubts. Maybe she didn't enjoy it as much as me? If she had a good
time, she would have given me her number. Was this just a one-night
stand? I mean maybe she thought my performance, only getting hard once,
was typical. By the time Wednesday rolled around, I was convinced she
wasn't interested. Then when I picked up my mail as I got home from
work, there was a small padded envelope in my box. Normally, I only got
junk mail and bills, so this caught my eye.
I opened it and took out a single sheet of paper, fancy stationary. The
writing was almost like calligraphy, very sweeping, perfectly written
cursive. I hurriedly read it
"Donnie, I had a nice time with you the other night. I sense a lot of
potential in you and would enjoy being with you again. If you want to
see me, please come to the club on Friday wearing my little present.
Kisses, Eve."
I was ecstatic. I reached in the envelope and took out her gift. I was
immediately dumbfounded. It was a pair of woman's panties. Lace
triangles in front and back, connected by two side strings on each
side, all in a rich mocha. They felt silky smooth, but looked so small.
I just couldn't understand the purpose of them. If Eve wanted to see
me, why ask me to wear such an item? I showed no desire for her
lingerie when I undressed her, or in any conversations prior to that. I
just shook my head in confusion. I went ahead and had dinner, and did a
few chores around my apartment, the whole time trying to figure out the
meaning of her request. The next couple of days, my thoughts went to it
almost constantly.
I was dying to see her again, but I was very reluctant to wear her
gift. I had tried them on and the panties fit, surprisingly, well. I
mean they were snug, but not too tight. I looked funny in them of
course, as they were meant for a girl. I was so confused. When Friday
night came, I was still torn. But I couldn't pass up this chance. Maybe
it was some kind of funny test to see if I was really interested in
her? So I put them on, under a nice shirt and pants, and went to the
club about 9 o'clock. I knew it was early, but I didn't want to miss
her. I sat at the bar, nursing a drink, when about an hour later she
came in. Eve looked even hotter than I had remembered. She wore
skintight leather pants, a sheer lace top, and sky high heels, all in
black. I couldn't take my eyes off of her. When she saw me, she smiled
broadly and came to me, giving me a quick kiss on the cheek.
"Donnie, I'm so glad you came. I wasn't sure you were brave enough. Buy
me a drink, so we can chat."
I got her a drink and we talked, but avoided any mention of her
present. The words just seem to flow, I loved talking with her. Finally
after she finished her drink, she moved in close to my ear to whisper.
"So, are you wearing my present?"
"Yes, I don't know why you wanted me to, but I did. What's the meaning
of it?"
"I wanted to make sure you'd follow my requests. Unzip your pants, so I
can check to be sure you're wearing them."
I moved to face the bar, and discreetly unzipped my jeans. Without
hesitating, Eve put her hand down my pants, and lightly felt my cock
wrapped in the silky panties. Laughing, she took her hand out.
"Oh Donnie, that's not how you wear panties! Especially such tiny ones.
But don't worry I'll show you how to do it later at my place. But first
I need you to do something else for me. Then we can go, okay?"
I zipped my pants closed, while she reached into her purse. Eve pulled
out a small item of clothing that looked to be the same lace and mocha
color as my panty. She held up, between the two of us, using my body to
shield it. I saw right away it was a bra. A small one, with just a
couple of lace triangle cups and a thin band and straps. But a bra! I
looked at her like she was crazy, but she just smiled and handed it to
me.
"Now if you want to go home with me tonight, go into the bathroom and
put this on. Don't worry it's not big enough to show through your
shirt. No one else will see it. But it will show me that you're ready
for me. The other night, in bed, you started really strong, but you
rushed. I want to take you home, so we can go slowly and I can get you
focused. If you want to get me in bed again, go put this on."
I hurriedly crumpled up the bra, trying to make it as small in my hand
as I could. I could feel my face flush, and I glanced around to see if
anyone else had seen it. I couldn't believe Eve was asking me to do
this. But I kept hearing her say go back to my apartment for sex. I
really wanted it, so swallowing my pride, I got up and went to the
men's room.
Luckily, the only guy there left as I soon as I entered. I went into a
stall and hurriedly put it on. I had a pull on shirt so, that was easy
to take off. I hooked the bra in front, spun it around and then put my
arms through the straps to pull it up. I had seen my ex-wife do this
enough times to know about it. Again, I was surprised at how well it
fit. Putting my shirt back on, I was nervous. Was it really hidden? I
stepped out of the stall and quickly looked in the mirror. I couldn't
see any indentations, creases or signs that I had a bra on under my
shirt. By now, I just wanted to go back, get Eve, and leave. So I went
back to her at the bar.
As I walked toward her, she smiled even wider. She put her hand on my
back as I sat down next to her. I could feel her rub across my back,
her fingers tracing first the band and then one strap before she
removed her hand. I could tell she was pleased. I was about to say
let's go, when she asked me to get us another drink. I could see she
wanted to test me some more. So I did. We sat there talking, me nervous
as hell and she calm and relaxed. Finally after we finished, she
looked.
"Are you ready to go back to my place Donnie?"
"Yes, of course. Let's go."
"Hold on, first I want you to know that I expect you to do exactly as I
ask, okay? If I want you to do something I expect you to follow
through. If I am going to invest more time in you, I expect you to be
receptive."
"Sure, sure. I'll do as you ask."
Eve stood up and taking my hand led me out of the bar. Outside, she
told me to follow her car and she'd take me to her apartment. We headed
down the road, with me closely behind her. Her place wasn't as close as
mine was, so it took some time. But soon, we pulled up to a nice
complex. Her place was on the third floor, so we took the elevator up
and then went in. As soon as we entered, she turned to me.
"Go ahead and get undressed. You can fold your clothes, neatly, and put
them on the table by the door. I just want you in your new training
clothes whenever you're in my place, okay? If you are going to learn
how to really please a woman, you need to follow my lead."
I felt awkward, but did as she asked. It seemed so strange to be
standing there, in girl's underwear, while she was still fully dressed.
I didn't even get excited. I mean, she watched me the whole time, as if
I were in an interview. When I finished, I stood there, expectantly. I
thought it better if I just waited for her to tell me what to do.
"Wonderful, you look so cute in your new outfit. But let me show you
the proper way to wear your panties. Pull them down for me, not far,
just to mid-thigh."
I blushed, but did as she asked. I never imagined having a woman
comment on my wearing panties. Once I had them down, she continued.
"What I want you to do, is take your balls and push them back into your
body. There are natural cavities they can go up into and then you pull
your peter back between your legs, tight against your body. While you
hold it there, pull up your panty so it will stay where it belongs. Now
go on, try it yourself."
I did as she described. I was surprised at how easily my balls went
inside me, although it was a little difficult to maneuver my panty into
place with only one hand. Once I had everything done, though, I looked
at Eve, not sure what to expect. She smiled, indicating she was
pleased. She ran her hand over the front of my panties, down far enough
so her fingers could feel the shaft of my cock between my legs.
"Very good. From now on I want you to tuck yourself that way whenever
you wear panties for me. It not only gives you a smooth flat look down
there, but helps de-emphasize your cock. I've found that men,
naturally, focus on their sex organ and their pleasure when they have
sex with a woman. Like you did the other night. You started off so
well. Once you began to kiss my pussy, you were giving me the kind of
pleasure I like, and deserve. But you stopped just as I was starting to
respond and moved to put your peter in me. I mean it was okay, buy you
immediately focused on yourself, not seeming to care whether I orgasmed
or not. That's not unusual for men. So what I want to do tonight, is
show you exactly what I want you to do to give me my orgasms. So if you
peter is put away, out of sight and uninvolved then you'll be more
likely to remain focused on my pussy. That's one reason you'll wear
cute girl things for me while I train you. From now on, you're my
little girl."
I blushed a bit more upon hearing her describe our sex the other night,
as I knew she was right that all I focused on was myself. I mean, I
made token efforts to keep her stimulated, but mostly it was my cock
that I was concerned about. Having explained her plan, Eve took my hand
and led me back to her bedroom. She quickly removed her clothes,
handing them to me to put in her hamper. Once she was nude she lay back
on her bed, her legs slightly spread. I reacted to the sight of her
beautiful pussy, spread open, and my cock began to stiffen a little.
But given its new position, there wasn't a lot of room to expand. In
any case, my thoughts and efforts were soon directed elsewhere. I knelt
between her legs, as Eve explained how this would work.
"Donnie, I want you to start like you did the other night. Slowly
kissing me and working your way to my pussy. Begin at my feet,
alternate between each leg, as you go upward. Soft, light kisses will
do. Your goal is to begin to excite me. That was one of your saving
graces the other night. Your kisses were quite good. It's an advantage
to have such big soft lips like yours, most men don't have such a
pretty mouth with full lips. Now I'm going to tell you how to use them
to please me. Just listen to my instructions and you'll learn what to
do."
I began to kiss her feet, then legs, and made my way upward until I was
kissing around her pussy. Eve was very detailed in her instructions,
telling me exactly where to kiss, when to use my tongue, whether to be
soft, or hard, and how much time to put into every area. She had me
start at the outer edges of her labia, kissing them first, then lightly
licking them and finally taking them into my mouth to suck on them. I
had never spent this much time on a woman's pussy and I haven't even
been inside her vulva. Eve had me thoroughly focused on her labia for
at least ten minutes, before she allowed me to repeat the same
techniques on her inner labia, at this point, I could smell and taste
how she was starting to get excited. But Eve had me go slowly, not
rushing at any stage. But she did lead me finally to where I was
kissing, licking, and sucking both her clitoris, vagina, and the whole
vulva area.
I could tell my efforts were appreciated and finally after a half hour
she began to really moan, squirm, and react as she approached climax.
She was fully lubricated, the touch of my tongue and lips eliciting a
steady stream of moisture from her. Eve had a very distinctive taste,
spicy and tangy, but with a hint of sweetness. As she fully entered her
orgasm, she pressed her pussy tight against my face, my tongue and lips
focused on her inner labia and vaginal opening, while she rubbed her
clit on me. Hitting her peak, she pressed her thighs against my head,
holding me in place while her body was rocked by spasms. When she
finally relaxed, she told me to go back to the outer edges of her pussy
and lightly begin the process again.
My jaw muscles were a little tired and I felt like I had been eating
her forever, but I did as she said. I could sense, she wanted another
orgasm, so I repeated what she had asked me to do before. Eve was
pleased by how well I had learned my lessons, but this time as she
began to build her excitement she told me to just focus on her clit. I
was to suck on it and lightly flick it with my tongue, changing speeds,
pressure, and rhythm in response to her directions. I knew she was
starting at a more excited state, but still it took her a while to
reach her second orgasm. This one seemed so much more focused and
localized, I guess because all my attention was on her clit. When she
came, her body shook but she kept her clit pushed tightly against my
mouth. Eve began to relax, and I started to move my face away from her
thoroughly soaked pussy. Eve stopped my movement with her right hand,
holding me near her.
"Donnie, don't stop until I tell you. When you begin to please a woman
properly, you keep going until she has told you she's had enough. Men
get the idea that sex is just one big orgasm, but women can have and
really need multiple climaxes. They continue to build, each one more
powerful than the last. So I want you to continue to kiss me down here
until I say no more. Begin this time, with cat licks. Use your tongue,
flat and broad as you can make it, to lap up my juices. Focus on my
labia, outside, inside, and over the top. I need you to continue to
provide me with sensations, as I can feel my ultimate orgasm building.
Just do as I say."
By now, I was really starting to feel fatigued. My jaw, lips and even
my tongue were tired, sore, and a little raw from the constant
movement. But I did as Eve wanted. Her instructions were even more
detailed, as I worked her toward her third climax. Each step seemed to
be quicker, as she was obviously very excited. Finally as she began her
final push, Eve reached out to hold my head, her hands grabbing it
between them. With me firmly in place, she began to rub and hump my
face. I kept trying to kiss and lick, but she was more interested in
generating friction by herself. She moved faster and faster, pushing
her pussy hard against me. In the process, she had coated my face with
her juices, leaving it slimly and shiny. Eve finally peaked, screaming
as she held her pussy tight to me, actually squirting as her body was
racked with a tremendous orgasm. Her thighs were tight against my head
as her hands still held on. It was like she was being overwhelmed so
much that she needed to hold on for dear life. This time, when she
finished, her legs, arms and whole body fell away from me, leaving me
kneeling there still.
Eve whispered that I need to clean her up. To softly lick her to get as
much of her secretions as possible. I began to do so, trying to be as
gentle as possible. After a few minutes, I heard a contented sigh. She
reached down and lifted my chin up, away from her pussy. She was
smiling, obviously very satisfied.
"That will do Donnie. I knew from the first time we kissed, that those
lovely, soft lips would be perfect for cunnilingus. Your face looks so
perfect, all shiny from pleasing me. That's a look you'll come to
cherish. You did very well. With more training, instruction, and
practice you'll be able to please any woman at any time. Is you cock
throbbing? Once you've been fully trained it will not only throb, but
might even come on its own, even tucked tightly in your panties. But
for now, you should be very pleased with your effort. I bet you've
never given a woman three orgasms in one night, have you? You can get
up now, bring me my robe from the back of the door, please."
I got up and brought Eve her dressing gown. By now she was standing up
and began to leave the bedroom, with me following. I was happy I had
done so well for her, but a little put off that I had gotten no orgasm
of my own. As we entered the living room, she went to the table that
held my clothes. Picking up the pile, my shoes on top, she handed it to
me. Then opened the door.
"Donnie, I need to get to bed now. But don't worry I'll contact you
very soon for more training. I see you have lots of potential and I've
got to keep working with you. Night honey."
With a light slap on my butt, she guided me out into the hall and shut
her door. I was petrified, looking quickly around. No one else was in
the hallway, so I quickly put on my pants and then a shirt. I didn't
bother with my socks, and was just putting my shoes on when the
elevator door opened. Two young women came out, and I immediately
blushed. I knew my face was still covered in pussy juice, and I
imagined Eve's scent was all over me. I couldn't look at them, as I
made my way to the elevator. After we passed, I heard them whisper and
then giggle. I quickly went downstairs and drove home. My head was
spinning, as I reviewed what had happened. It was clear Eve was going
to control our interactions, as I still did not have her phone number
or last name.
At home, I was so horny I had to jerk off right away. I got undressed,
although for some reason, I left the bra and panties on. I pulled my
cock from between my legs and began to stroke it. I exploded after no
more than a dozen strokes, cum spurting out and covering my stomach. My
tensions released, I got up to take a shower. I made quite a sight, my
face covered in dry vaginal secretions and my body covered with my own
semen. I just shook my head as this was something I had never imagined.
But I was also worn out. I took a quick shower and fell asleep.
The next few days were pretty nerve racking, as I waited to hear from
Eve. I both wanted her to contact me, but also had some trepidation
because of how odd our relationship had gotten. I did go ahead and
clean the bra and panty she gave me, doing them by hand as I had seen
my ex-wife do hers. The days drug by at work and I was about to give up
on Eve, until I found another package in my mail. The envelope looked
similar to the one she had sent before. I opened it, half-afraid of
what was inside. This time I emptied it all before reading her note. As
I was afraid of, inside there were more female items, a pair of dark
brown stay-up stockings and a tube of lip gloss. I quickly read the
letter Eve had included.
"Dear Donnie, I suspect you're getting eager for another lesson in how
to please women. Well don't worry if you do as I request, you can meet
me again Friday night at the club. First, I love that shiny look on
your face when you were done pleasing me. So I've given you a nice
shiny lip gloss. I want you to wear it for me and don't worry, it's
clear but oh so shiny. Also, I found you so cute in your new bra and
panties, I just had to add on to your attire. These are nice silky
stockings that should match your lingerie. If you haven't already, be
sure to wash you panty and bra set. Then you can wear those and your
new stockings when you come to see me on Friday. But first you need to
do a little prep. Wearing stockings require certain conditions to make
them shine.
Sheer stockings are very sexy, highlighting your legs and making them
look really cute. But stockings must be worn over smooth legs, legs
with no hair, so they look flawless. So if you want to see me again,
you need to be smooth. You can wax or shave, but you must be smooth.
Since it would look silly to just have smooth legs and hairy elsewhere,
go ahead and do it all. I will let you keep a little puff of hair above
your cock. I'll let you choose whether you want a little triangle, a
landing strip or a cute design, but keep it small. Elsewhere you'll be
smooth, including your balls and peter. Luckily for you, you're not the
extremely hairy type.
Smooth legs do help stockings look nice, but to finish the look, you'll
need a sexy pair of heels. I know you've enjoyed seeing me in high
heels, the way they curve your legs and elongate them can't be beat. So
pick out a pair, something that will match the nice brown look of your
lingerie and new hosiery. I suspect you'll have some difficulty walking
in heels, so you might be tempted to keep them short, like two or three
inches. But I will appreciate the strength of your commitment if you
choose a taller heel. Anything above three inches will be send me the
best signal. One last tip, you have small feet for a man, so you won't
have problems finding shoes in your size. Unless you want to go to a
store to try them on first, I think if you go one size bigger than your
male size, you'll be fine buying them online.
I can't wait to see you on Friday. When you enter the club, I want to
see your sexy, shiny lips glowing with your new gloss. Wear your
panties, bra, and stockings, and when we go to my house, you can slip
on your new heels to show off for me. If you continue to show your
commitment to learning to please women, then you'll also get a nice
treat. Kisses, Eve."
I put the letter down and picked up the lip gloss. I unscrewed the top,
pulling out the applicator wand. Just from how it reflected the light,
I could tell it would make my lips look wet and moist. Even if it had
no color, it would be a very feminine look. Then I looked at the
package of stockings. It showed a woman in heels, her long smooth legs
looking super sexy. I thought about how exciting my past few dates with
Eve had been. But then I shook my head no. She was asking too much.
Wearing a couple pieces of lingerie for her was one thing, but buying
women's shoes? No. Even worse, shaving my body? No. Walking anywhere
with my lips coated in a shiny gloss? No. I couldn't see myself going
that far for any woman. Even if she was the sexiest, most exciting
female I had ever been with. Just the thought of her perfect body got
me excited. But I couldn't do this could I?
I put Eve's letter and package down and went to get a drink. I needed
time to think. Rather than eat dinner, I had a couple of drinks and ate
some pretzels, thinking about my choices. It was true, I hadn't had sex
with a woman in some time and I had never been as excited as I was with
Eve. I thought about what she was really asking for. After closely
looking at it, she was really asking for more commitment from me.
Wearing the lip gloss would only be a momentary thing. Something to
visibly show her a willingness to do as she asked. If I shaved myself,
it would be clear I cared about her and wasn't interested in other
women. Also, realistically, it was fall and I wasn't going to wear
shorts or go swimming for months. So who besides Eve would see my
hairless body? I'd have time to let my hair grow if we broke up. As far
as the women's shoes, if I went ahead and ordered them tonight on
Prime, I'd have them in time. I had another drink and decided I should
at least look and see what was out there.
So I logged on, and starting looking at shoe styles. I knew I found the
gladiator style sandal sexy, and I soon found a site that had them, in
a dark brown leather and on sale. I checked out the heel height - 4 ?
inches, should really impress Eve. But could I wear those? The site had
a deal, buy one get one free. To be safe, I found a simple black pump
with only a four inch heel. Nursing my fourth drink, I decided what the
hell? So, I ordered them. As soon as I made the purchase, I thought now
it's too late to change my mind. I picked up the gloss, opened the
tube, and slowly coated my lips with it. I instantly thought of my ex-
wife, as she loved lipstick, especially shiny ones. I glanced at the
mirror by the door. My lips were shiny, but clear. At least they
wouldn't look like I had lipstick on them. I looked at my forearm. How
different would it really be without my light blonde fuzz on it?
It took a while, much longer than I thought it would, but by the end of
the evening I had done it. I was silky smooth everywhere. I did choose
a simple landing strip look, and I had to admit it made me look very
feminine. By the time I was done, I had time only to finally eat a
sandwich before going to bed. I wanted to try on my new stockings, but
decided to just wait until my heels got here. That way I could see the
whole image. I was shocked at how nice my smooth legs felt when I
slipped into bed. The way they glided over the sheets sent a chill up
my spine. The next day, I got up and realized what I had done, I
blushed. I knew if I hadn't had a few drinks I would never have had the
courage to do it. But now I was glad, I couldn't wait to show Eve.
The heels showed up on Friday, so they were waiting on me when I got
home. I was truly excited, as I got ready. I decided to take a shower,
lightly shaving my face first, then my legs and underarms. I put on the
fragrant lotion I had picked up yesterday, after reading a story that
emphasized how you must moisture your shaved skin if you want to keep
it silky soft. A month ago, I would have never considered reading
women's magazines for beauty tips, but now it seemed logical, I mean I
wanted to impress Eve.
Once I was done, I slipped into my panties and bra. They had been on
top of my dresser for days, tempting me every time I walked by. But now
it was their time. It felt good, if embarrassing to be safely tucked
away, my peter snug between my legs. I slowly worked the stockings up
my legs, something I had watched my ex-wife do many times, so I knew
how to roll them up, pulling them tightly as I worked the silky nylon
up my leg. God did that feel sexy! I knew Eve would like them. Standing
in front of my bathroom mirror, I slowly applied my gloss. The light
literally bounced off of my coated lips. I laughed inside. Eve was
right, they looked like I had just finished licking up her juices from
her pussy. I consoled myself that any guy noticing my lips would think
twice, once he saw me with Eve. Her sexy body would be justification
for anything.
I slipped on my pumps first. They fit nicely, which was a relief. I
stood up anxiously. I wobbled just standing there. I slowly took a
step, holding on to the bed as I did. Another one. Then I made it all
the way around to the other side of the bed. I was getting a feel for
this. I ventured away from the bed walking toward the full-length
mirror on the back of my bedroom door. My word, I looked pretty
feminine, at least from the neck down. My body wasn't very curvy, but
the bra, panty, and stockings made it look like a girl's. I watched
myself as I walked back and forth. I was getting a feel for how to
step, how to keep my balance. I had to constantly pay attention when I
walked, but I had an idea with more practice, it would soon be second
nature. So, I sat down on the bed again, and switched to the higher
gladiator sandals. They were a bit tighter and I immediately felt more
pull on my tendons from the heels, but I felt Eve would love the look.
I took it slow but soon, was walking acceptably. I had another three
hours to practice before meeting Eve.
I decided to just put on a white dress shirt and walk around the house,
get something to eat and practice walking. I imagined how Eve would
like how I looked in the shirt, my stockings peeking out. I went about
my plan, but after an hour, my feet were hurting. Since I could walk
reasonably well, I decided to take them off to rest. I mean, I
shouldn't be moving a lot at Eve's place anyway. Soon, it was time to
get ready. I decided the shirt was okay, if I wore a blazer over it to
help hide my bra. I also picked a looser pair of dress pants rather
than jeans, as I didn't want to damage my stockings. I skipped socks,
figuring in the dark club the dark hose and a pair of loafers would do.
I was excited and anxious as I drove to the Club. This time, Eve showed
up early, and we got a drink. She loved my lips, moving her nail around
the outside of them, as if she wanted to touch them. I could see she
was curious, so I showed her my ankles and she seemed pleased. Pretty
soon we headed out.
As we pulled into her parking lot, I was getting excited. All the
preparation I had done during the week was for this moment. I followed
her up the stairs, carrying the box with my sandals in my hands, and
into her apartment. I instinctively looked at the table, where I
imagined she would want my clothes. I was right, she even had a big
shopping bag there. I turned to look at her.
"Go ahead Donnie, you know the rules. You can put your clothes in the
bag, except for your blazer. I'll get you a hanger for that. You can
also put on your training shoes, and touch up your lips. You need to
reapply your gloss frequently."
While she went for the hanger, I stripped down to my lingerie and hose.
Quickly slipping on my heels, I had everything in the bag by the time
she returned. I was using the applicator, to put on more gloss and I
glanced at her to see her reaction, as she handed me the hanger. Eve
was smiling, but was also holding her phone, as it had started to ring.
Answering it, she looked at me.
"Hold on a minute, okay? Donnie, I have to take this call first. You
don't mind doing me a favor do you? I noticed how clean your place was,
so you can help me. I left some dishes in the sink. You can help me by
washing them up. Everything you need is under the sink, including a
pair of rubber gloves to keep your hands soft and aprons to protect
your pretty little underthings. I won't be long."
While she talked to me, Eve had run her hands over my smooth belly,
down over my panties to feel my legs covered in nylon. Her touch sent
chills over me. I was surprised at how easily she asked me to help her,
but I felt good that she saw how clean I kept my own place. It would be
easy to do a few dishes for her. I went to the kitchen, while she sat
down in the living room and began to talk to her mystery caller. There
were more dishes than I expected, but the supplies were under her sink
like she said. There were a couple of aprons, a plain one with a note
saying to wear this for washing and a pretty style that was for
serving.
I looped the apron over my head, and with my gloves on, I filled the
sink with hot, soapy water. While the dishes soaked, I checked out her
cabinets to see where she kept the rest of her dinnerware. It didn't
take long to wash and dry them, putting them away. When I finished, I
went ahead and wiped off her counters and the breakfast table in her
kitchen. I wanted her to know I cared enough for her, to do a good job.
With my chores done, I switched aprons to a cute white eyelet style
that covered me enough so my stocking tops were under it. I stuck my
head around the corner to tell her I was done, but she was still
chatting. Seeing me, she waved me over, breaking her conversation a
second.
"Donnie, bring me a glass of wine sweetie, there's an open bottle in
the fridge. I'll just be a bit longer here, so if you don't mind, you
could help me by going through my place and picking up a bit. That's my
girl."
Eve immediately returned to her phone conversation, not really waiting
for me to agree. I could sense she just expected it. So I found the
wine, poured her a glass, and took it to her. A curt nod of her head
showed her appreciation. Then I began to check out her apartment. Eve
was right, there were things out of place everywhere. She had empty
soda cans, food wrappers, used dishes, dirty clothes, coats to be hung
up, and everything was dusty. I was lucky that I still had soapy water
in the sink and I quickly put on my work apron. I let the dishes soak,
put her dirty clothes in her hamper, and dug out a feather duster from
under the sink. In short order, I had the place looking much better,
which I knew Eve would love. Seeing my work was done, I was ready to
play. I took off the gloves and apron, checked to be sure my nylons
were pulled up, coated my lips with gloss again, and went to see Eve.
As I came in the room, she stood up, still talking on the phone. She
unbuttoned her jeans with one hand, while she kicked off her pumps. A
simple gesture indicated I was to remove her pants. I knelt in front of
her and worked them down and off her legs. Another gesture led me to
remove her panty as well. Naked below the waist, Eve sat back down on
the chair, and positioned her legs over the arms of the chair,
spreading her pussy open for me. Another simple gesture and I moved
closer, starting to please her using the techniques she showed me last
week. I couldn't believe she had me doing this, all the while chatting
with her friend. Finally after she began to get very excited, as I had
remembered my training well, she ended her conversation, so she could
really focus on her rapidly approaching orgasm. As it swept over her,
she wrapped her legs around me, pulling me as close as possible. When
she began to come down from the sexual peak, she looked at me.
"Donnie, I'm so impressed with you right now. Not only are you totally
smooth and sexy, wearing my gifts to you, but the type and height of
the heels you choose show me how much you value me. Then you go the
next step and help me in my home, showing me the care and devotion
you're developing. I've never had such a quick learner. You've my best
girl so far. Your technique was very good, you obviously remembered
what I showed you last week. But now, it's time I teach you a few more
lessons. You know sometimes a woman likes to take control, to really
guide her own sexual needs. Tonight I'm going to teach you how to
surrender to a woman that way. You pour me another glass of wine and
bring it to me in my bedroom. Also, don't forget to pick up my things.
I expect you to remember these lessons as well, if you want to continue
to impress. Oh but put on your pretty little apron before you come
back. You'll wear it in my place and it will be a part of your new
training attire until further notice."
I did as she asked, although it felt a bit humiliating to wear the
apron. I reasoned Eve wanted to emphasize my training status a little
more emphatically than just having to wear women's wear. I had to
admit, it did give me a more polished look, as it complimented my
stockings almost like a dress. I put her clothes in the hamper and
entered her bedroom, carrying the wine and her heels. I saw her smile
when I entered, seeing me in the apron must have pleased her. I put her
heels in the closet and moved to her. As she took the wine glass from
me, she reached over to caress my nipple through the fabric of the
apron and my bra. It responded favorably to her touch.
"Donnie I need you to lay down on the bed, on your back, hands above
your head near the headboard. Tonight I am going to mount your face. I
also want to emphasize your loss of control, so I'm going to tie you in
place."
Eve's description, especially about tying me up, made my heart race. I
hadn't ever done anything like this. Once I had assumed the position
she wanted, Eve took a pair of pantyhose softly tied my hands together
on the head board. She repeated that to restrain my legs as well. It
was pretty clear these were symbolic bonds, as they were not tight
enough to really keep me from getting out. With me held in place, Eve
ran her hands over me, feeling my hairless, smooth skin. Caressing my
legs through their nylons, pinching my nipples under their bra, and
reaching between my legs to stroke my peter in its panty. Smiling she
told me loved how committed I had become. Being willing to go outside
of my comfort zone was the strongest sign someone really cared for you
and she was very pleased. Now it was time for her to take full
possession of me. This time, the sex would be rough. She was going to
grind away on me, using me to achieve the friction and pressure needed
to give her this kind of orgasms. If given the opportunity to lick or
kiss her sex, I was to do it. I was to listen for any instructions, but
tonight it was going to be all her.
The next two hours she lived up to her proclamation. Eve found so many
ways to rub her pussy on my face, to use my nose, lips, even my chin,
to give her what she wanted. I counted three big climaxes, and many
small, shuddering type releases, where she achieved some type of
emotional peak. Several times, she planted her pussy tightly on my nose
and mouth, so that even breathing was difficult. When I could get a
breath it was full of her moistness, her scent, her sexual essence. Her
motions coated my entire face with her juice, so much that it was
slick. When she was recovering from an orgasm, she would positon
herself, so I could have full access to her pussy, allowing my tongue
to tease her back toward another climax. But the ultimate action to
take her over the top, was always from her. While she used me, Eve did
constantly praise me, telling me that I was such a good lover, far
better than before she began to train me.
Finally, after her third big orgasm, Eve reached up and untied my
hands. She then turned, a hundred and eighty degrees, so her legs were
on either side of my head and her ass cheeks pressed against my face.
Looking over her shoulder, she told me it was time for me to learn how
to help a woman cool down from a climax. She said any loving man,
should eagerly show the woman who he was pleasing that he wanted her
more than anything. That he would do everything for her.
"Donnie, take your hands to separate my cheeks, so you can use your
tongue and lips to softly kiss my ass. I want you to make love to it,
but lightly and tenderly. You should be as close to me as you can. I
want to feel your kisses of devotion and worship, as my emotions settle
down. Now show me how much you appreciate me."
This request was totally unexpected. I had never kissed a woman there,
never tasted a woman's ass. Eve had made it clear what she expected.
So, I took each cheek in hand and pulled them apart. I could see her
asshole, covered with her juices, sitting just above her swollen pussy.
I reasoned it had to be about the same. I also decided immediately,
that I would approach her ass like I did her pussy. So I began by
licking and kissing her cheeks, and the cleft between them, as I worked
my way to her hole. Eve softly moaned, confirming my strategy.
After a few minutes, I worked my way to her opening. Slowly, with a bit
of hesitation, I put my lips on her puckered hole and gave it a soft
kiss, then another. Taking the plunge I went ahead and French kissed
her ass, pushing my tongue in. At first her muscles kept me from making
much of a dent, but as Eve realized what I was doing, she reacted by
pushing outward. That allowed my tongue to go in, as far as I could
reach it. The taste was strong, different, but partly because of all
the pussy juice that covered it, not bad. With my eyes closed, I
pretended I was merely licking her pussy and not her asshole. I
continued to kiss her, running my tongue in and around her. As I
removed her pussy juice, her taste became stronger, but now I was too
focused to stop. It did hit me what I was doing. Before I met Eve, I
would never have considered doing this, for any woman. Now I was trying
my best to kiss her asshole, like it meant everything. I felt my face
blush as I realized just how submissive I had become for her. Finally,
after about 20 minutes, Eve looked over her shoulder at me again.
"That will do. That will do Donnie. Time for your reward. You've been
so good at learning lessons, I need to let you have something in
return."
Eve's promise of sexual favors peaked my interest. Since we began my
'training' any sexual release had been through my masturbation after I
got home. I was hoping for her to mount my peter instead of my face
now, but would gladly take any attention from her. She untied my legs
and told me to get up on my knees, head on her bed. I was concerned
about this positioning, but did I as I was told. Eve spent a few
minutes rubbing my body, running her nails over my skin, as if to
highlight how soft and smooth I was now. Then she stepped behind me.
Eve reached between my legs to stroke my peter.
"Donnie, I just love feeling you like this. It just seems so right and
natural now. When you are tucked back, safe and sound, your peter just
seems better somehow, don't you think? You know, I think the next thing
we should do, is have you tuck yourself all the time, not just when
you're with me. I bet the more you keep your little peter between your
legs the more you will come to like it. Also, I'm going to have to find
a way to make you come with it like this. Then you'll be so much more
in tune with your feminine personality. It will be a real improvement.
But for now, I'll have to let you out."
Slowly and deliberately, Eve pulled my panties off my ass, down to my
thighs, allowing my peter to drop down, although my balls were still
inside of me. She reached between my legs from behind to stroke it a
couple of times. Her touch felt like magic, and I began to get erect
immediately. I looked backwards under my body, as she fondled me. The
sight of her pumping my peter, and the feelings from it, made
everything she had asked of me worth it. But she stopped, leaving me
throbbing. I could see her walk along the bed and she opened a drawer
from her nightstand. What she took out, made me shudder. It was a
thick, long dildo, with a big cock head and realistic balls at the
base. I watched, stunned, while she squirted some lube on it, stroking
up and down as she had done my peter. Smiling, she saw me looking.
"Isn't it beautiful? I love big cocks, there's just something about
them. So I keep this around, since most guys don't really have anything
like this. I thought you'd like to feel what it's like to take this in
you. Now I know you're likely a virgin when it comes to your boy pussy,
so I'll take it easy and use lots of lube. I'll also stroke your pretty
peter so you will truly associate the feelings of this cock with
pleasure."
Eve moved back behind me. I felt the cold lube gel on my asshole, as
she squirted a big glob on it. My legs started to tremble and my peter
was getting soft. The idea of that monster cock entering me was scary
and not at all erotic. I was trying to prepare myself for it, when I
felt another cold shock on my peter, but it was followed by the warm
touch of Eve's hand. She put some lube on it and resumed stroking me.
Once again, it got hard as the slick lube allowed her hand to easily
slide up and down my shaft. Her masturbation distracted me, until I
felt a hard presence at my asshole. Eve had positioned the dildo at my
opening.
She slowly began to push and I, just as slowly, began to open up. As
Eve forced her dildo into me, she continued to masturbate my peter. The
distraction was working, as it made its way inside. I felt the pressure
on my asshole, as the muscles were tensed up, but the lube helped the
big head of the dildo finally slip past the ring of muscles. With the
head inside, the smaller shaft kept me open, but not painfully so. Eve
was able to continue to fill me with the huge dildo, matching her
pushes into me with her stroking of my peter. I had to admit, after
several weeks without her touch, this was becoming erotic despite my
hesitation about the anal play. What really flipped the switch was when
she began to pull back on the dildo and then set up a regular in and
out. Eve matched her play with my peter with her play with my ass, so
that I was now getting overwhelmed by sensual feelings.
Eve took this opportunity to quiz me about how I had prepared for her.
Where I had gotten my shoes, how I had selected the narrow landing
strip, whether I had shaved it all, or waxed some areas, she asked
about almost everything. My answers were generally short, as I was
almost breathless from her attentions on my peter and ass. But I did
elaborate occasionally. Eve seemed very pleased when I admitted I
actually bought two pairs of heels. She told me that was a good sign,
as for most women, shoes were a big part of their identity. The fact I
wanted to have more than the minimum was an excellent sign. Finally,
she seemed satisfied with my responses and began to focus full force on
her manipulations of me, increasing her pace when fucking my ass and
fondling my peter.
When her dildo began to rub against my prostrate, then it was only a
matter of minutes before that and her manipulation of my peter, caused
me to climax. I had my head buried in a pillow as my body twitched. I
shot stream after stream of come, the apron draped below me catching
it. When she saw me coming, Eve giggled.
"Feels pretty good, doesn't it? I knew you'd love it. Every girl loves
a big cock, once you get used to them. You've certainly earned this
reward for how well you've accepted your training, Donnie. I am so
happy that you've embraced the idea of learning to really please a
woman. Many men can't or aren't willing to put their partner's pleasure
above their own. But once you make that commitment, you'll find that
your pleasure will be even better in the end. Now, you need to go get
cleaned up. Rinse out your come from your apron before it stains. You
can take it home for a real washing. I want you to wash off my cock.
We need it ready for the next time. Finally write down your email
address, I need to send you a couple of links."
Eve had left the massive dildo buried in my ass, so it was awkward
making my way to the bathroom. I had to hold it in reaching around with
my hand. Pulling it out, was almost as bad but holding it in my hands
to clean it, as if it were a man's cock, was the worst. But I did as
she asked, also wiping the lube off my body. When I returned, she had
wrapped up in a robe and I could tell it was time for me to leave. I
put the clean dildo back in her nightstand and followed her out of the
room, carrying the wet apron. She told me to get a plastic bag for my
apron from the kitchen and again, I did as I was told. When I returned
to the living room, Eve was holding my blazer open, and helped me slip
it on. She then gave me my gloss, watching as I slowly coated my lips.
As before, she handed me my bag of clothes and with a quick peck on my
cheek, ushered me out into the hallway.
I felt totally exposed now, even with the blazer. It covered my bra and
panty, but the stockings and heels put me on display. I was torn about
what to do. Should I try to change in the hall, or just hurry to my
car? I fumbled with the bags a second, but then I just wanted to go. I
went down the elevator and with a quick glance around, scurried to my
car. Once safely inside, I drove to my apartment complex. After parking
I slipped on my pants and changed shoes before going upstairs. By the
time I was inside my apartment again, I was beginning to feel some
relief. My ass sill throbbed, but I was hard again. So I undressed and
lay back on the bed to quickly jerk off. My second orgasm of the night
wasn't as good as the one Eve had given me, but it did relax me. A
relaxing shower and I fell asleep wondering where this relationship
would lead next.
I woke late the next day, stumbling my way to get some coffee and then
breakfast. As I thought back to last night, I realized I had crossed
boundaries I had never thought of before. Allowing her to tie me to the
bed, emphasized how submissive to her I was becoming. The range of anal
play, from my kissing hers to her fucking mine, was something I had
never imagined doing. But it was over. I suspected the next training
sessions would focus on something else, perhaps improving how I used my
peter to please her pussy. I knew whatever it would be, it would be
exciting. I noticed I had been on a sexual edge ever since I met Eve. I
saw no reason for that to stop now. I remembered she had asked for my
email address and I opened my laptop to check. Sure enough, there were
a couple of messages from Eve. My first real way of corresponding with
her.
The first email was loaded with praise about how sincere I had become.
Eve acknowledged she was asking me to do things that were unusual, for
a man, but she felt that my acceptance of her requests was the most
sincere form of admiration there was. She loved how I had been able to
give her multiple orgasms, it was among her best sex ever. She also
liked how I had remembered my training techniques without any prompting
from her. That kind of retention was going to be very important,
because to be the best sexual partner for a woman, I would need to be
able to please her without being told what to do at every step. She
wanted it to be instinctual for me and was sure I could do it. Eve
praised my enthusiasm for her 'calming', telling me that no man had
ever plunged so deeply into her, nor shown such an eager willingness to
prove their devotion. She ended the email by telling me not to be
hesitant to embrace the next steps.
Those steps were described in the second email. First she gave me a
couple of links, to online sites where I could purchase more feminine
things. Eve told me that my willingness to wear women's items, to
voluntarily subdue my masculinity was such an important step in proper
training. Only by embracing my inner girl, would I be able to put a
woman's needs first and foremost. I would then reap benefits beyond my
wildest dreams as a reward. I had signaled my willingness to take these
steps by buying more than one pair of shoes. So, to help me reach this
peak, I was to acquire more items. She wanted me in a new outfit every
time we were together. She also wanted to wear women's things all the
time. If I wore a pretty pair of panties, a sexy bra and silky hose
under my clothes all the time, then I would be comfortable with them.
Eve stressed that I should look at other lingerie options, too. A cute
garter belt, a body-shaping briefer, even an old-fashioned boned girdle
or corset, would signal a broader embrace of femininity. She wanted me
to accept wearing women's things as a natural state for me during my
training.
Beyond clothing, she wanted me to accentuate my personal femininity.
For example, it wasn't enough to be tucked when we were together. I
should embrace putting my peter in a proper place, all the time. That
way I would be smooth and flat in front, like a girl. I would elevate
my sexual desires to places other than just my peter. I was already
accepting my mouth and even my face as suitable sex organs to please
women. The more I put aside my male organ, the easier it would be to
please others and myself too, with alternatives. To this end, she
wanted me to consider enhancing my female appearance. A nice wig,
breast forms, even cosmetics would not only make me look more like a
woman, it would help me think more like a woman, which in turn would
help me please women better. It was an all reinforcing cycle. So, she
had included a discrete site for crossdressers that would be able to
give me the right kind of accessories. Her email spelled out specific
cosmetics, by brand and color that suited my skin tone. I could also
order these online.
Eve made it clear. I should be bold. Just like the heel height I had
chosen to wear, I should look for a sexy wig, bright cosmetics, and
most importantly, breast forms that would give me a real bust. I cursed
myself inwardly for being so eager to please her with the shoes, with
the lip gloss, with everything. Why did I find her so magnetic? I mean
after the first date, we've not even fucked. Sure she's gotten lots of
orgasms, but I've only had the one. And for that one, I had to let her
rape my ass. It still buzzed from that big dildo. Although, if I was
being honest, I would admit it was among my most memorable orgasms.
Now, to continue, she wanted me to basically become a woman, at least
appearance wise.
I quickly looked over the rest of her email and then looked at each
site in her links. The images of beautiful women in sexy, lacy lingerie
stirred my desires. But I had to remember, it wouldn't be Eve in these
wispy bits, it would be me. The crossdresser site was even worse,
because I knew the beautiful feminine images were really men, like me.
Or at least formerly like me. Now if I did what Eve wanted, I would
look like them. The choice of breast forms was mesmerizing. So many
options, sizes, and styles. I had never considered nipples and areolae
separately from breasts. But I could select what kind I wanted, color,
shape, and size, to make the perfect breast form. I had to think about
all this. So I closed my laptop. I needed some fresh air. Maybe I'd go
for a run.
I started to get ready and realized, it was too warm to run in sweats
and if I wore shorts, then my smooth, hairless legs wouldn't be hidden.
But I needed to think and burn off some stress, so what the heck. No
one ever noticed me anyway. I changed and headed out the door for a
nice leisurely run. I passed a few people, but I didn't see any
reaction to my smooth legs. The more I ran and thought about it, I
realized most people don't really care or even notice details like
that. Unless they're close to you. And for me, the only one close
enough now, was Eve. So by the time I got back home, exhausted because
it had been weeks since I ran this far, I knew what I was going to do.
I had thought out a plan. I definitely wanted to continue this
relationship, odd as it was, with Eve. I also wanted to impress her as
much as I could. So, all out was the only way to go. I knew my first
decision would be what size of breast form to get. I saw they ranged
from a cute little mound, an A-cup type, to super large. I found myself
drawn to those that would produce a D-cup size look. My ex-wife had
large breasts and I had always liked how they looked in lingerie. I
knew Eve would like me going big, but it had a high risk factor. She
had mentioned me wearing lingerie all the time. What if she included
breast forms in that request? I could hide A- or even B-cups, but
something like a D-cup would be seriously visible to everyone. But
there was one style, with full areola and a nipple that projected an
inch above the form, that I thought looked perfect. It came in my skin
tone and could even be glued onto my chest, if Eve wanted that. So I
put that in my cart. But before buying it, I wanted to see what kind of
bras, colors, styles, etc., could accommodate a D-cup breast.
To my relief, the sites to which Eve gave me links, had a wide range of
bra choices for D-size breasts. The more I looked the more I was
convinced that was me, or more accurately, the new me. Selecting my new
attire I decided to mix up my look, but meet what Eve had asked for.
Some were straightforward choices. I wanted each bra to have matching
panty, both color and style. I wanted them to be very feminine, with
lace, ribbons, bows, sheer panels, and as much feminine frill as
available. Pretty colors too, not just white, black or beige, although
I would have at least one of those as well. Surprisingly, I found once
I started putting together my lingerie trousseau, it was hard not to
buy a lot. I was becoming enamored with the idea of being a sexy girl
for Eve. But I forced some restraint, deciding seven bras, one for each
day, would do. I might have more than one panty for each bra, but that
was my baseline.
I had in mind what I would wear day to day, under my clothes, to please
her. Bra, panty, and pantyhose would meet that minimum. So I selected a
half-dozen pantyhose, in both tans and blacks. I figured when I was
with her, stockings would be my choice, as I felt they were much
sexier. Even though she had gotten me a stay-up style, I didn't like
the feel of the tight bands on my thighs, so I figured old-fashioned
style stockings would be better. That meant buying something with
garters, either a sexy garter belt, maybe a longer-style bra, like a
merry widow, or some other sort of shapewear. Once I began to look, I
saw a wide range of options. Once again, I had to resist the urge to
overspend. I eventually limited my picks to items with garters, that
each matched a bra and panty combo. I chose two garter belts, a wide
waist-cincher, a longline bra, a control panty brief, and a long-leg
girdle. I imagined wearing the girdles under my regular clothes, the
long-leg would be great over pantyhose, if I used it without its
removable garter tabs. Once I had decided to do this, I wanted to
really show Eve how much I embraced it. These kind of extras I hoped
would pay big dividends in the bedroom. I could see her letting me fuck
her again, of course after I properly warmed her with a few oral
orgasms.
I knew at her place she would expect me in heels as well, so I went to
the site where I bought my first heels. I soon had another half-dozen
pairs in varying colors and styles, the only constant being heels of at
least 4 inches in height, in my shopping cart. From her reaction to my
first pair, I knew she'd love that look. Maybe Eve was on to something
about me, because I loved looking for shoes to buy. It was harder to
limit my selection of these than lingerie. Once I had the items in the
shopping carts, I looked at the total cost. It was high, but I had
expe