Starting work at a new company with Kelly Part 4
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Seriously?
I turned 49 on my last birthday, my wife turned 56 on hers. When we were
younger the age difference never mattered, emotionally, it still
doesn't. Physically however, it has reared its ugly head.
Two years ago my wife told me that as much as she loved me, her interest
in sex was about nil. She was sad because that part of her life had
ended but despite her lack of "urge", she was still willing to
participate because she knew I was younger and still had needs. I loved
and still love her and I was willing to accommodate her wishes, but
honestly, sliding into wet pussy is, sliding into wet pussy.
I am her second husband. The first was abusive in many ways, emotionally
and occasionally physically, she loves me because I am neither. The fact
that I like to wear woman's lingerie amused her and because that is so
completely not macho, made her feel safe and unafraid.
Before her interest in sex diminished and her body changed, she enjoyed
me serving her as a maid or berated me when I was a school girl. She
liked when she took me in the ass with her strap on, as it gave her a
feeling of power and control that she had never known before. Yes, she
knew before we married that I was a cross dresser. So I was surprised
when she said, I really should shave.
She was reading in bed and I had just come out of the shower. I had a
towel wrapped around my middle. It stunned me when she said, "You know
Bill, your leg hair is so sparse, you should just shave it off. I mean,
assuming you are still dressing up when I am not around, it would be
much prettier when you wear stockings."
I said, "Huh, what?"
Susan laughed and said, "I am just saying that if you are still
dressing, if you want to be more feminine, you really should shave your
legs and chest."
I responded with, "Yeah, but, I mean, that would be a change, a big one.
But hey thanks for the suggestion."
She said, "Bill you know I have always thought that your wanting to wear
my panties was odd but cute. You know that I do not mind you pretending
in lingerie. Obviously, over the last couple of years, I have not been
there for you so if you want to take your cross-dressing to the next
level, I am ok with that."
"Seriously?"
"Yes baby and I will help if I can."
"Help?" "Help, how, I mean if you are suddenly interested, that's cool,
but how would you help?"
"Well I am not sure, I mean, I could help you with make-up and lipstick,
although you have never worn either that I know of. Or I could tell you
if a dress you have fits well or is too baggy. Gosh, I really have not
thought that far ahead, I was just thinking that I could help you be
more girly if that is what you want."
"Mary, I will have to think about it, I mean I thought I was doing it to
make you feel safer, but the longer we go without,....without contact,
the more I want to dress up."
"That's what I mean Bill, if you want to wear panties and a bra
everyday; I want you to know it is ok with me. What bra size are you by
the way, (giggling) in case I decide to buy you one?"
"Stop it Mary."
"No, seriously."
Blushing I tell her I am a 36C.
We did not speak of it for a couple of weeks and during that time I took
her suggestion and shaved from the neck down, figuring she was right, I
am not very hairy anyway. It did make my nylons feel much sexier and my
slightly puffy "man breasts" looked so much better in a bra, I was
amazed at the difference in the mirror.
A week before my birthday Mary asked me if there was anything special I
wanted. I answered no, I had what I needed. She then surprised me again
by asking, "Is there anything feminine that you need that you have been
too embarrassed to get on your own?"
Blushing, I swallowed and stammered that I had always wondered what a
corselet would be like.
She said, "That's it then, I will get one. But they are expensive so we
should get the right size."
"Seriously?" I heard myself say.
"Yes, seriously. Why don't you fetch the measuring tape? Change into
your best fitting bra and panty while you do so we get the measurement
right." she added' watching me.
"You want to see me in panties and a bra?" I gulped.
Laughing she said, "I want to not waste money."
Nervously I left the room, my head spinning. I got the tape and then
went to the spare room where I keep "her" things. I selected a light
blue sheer cup bra and the matching lace panty. I slipped both on
quickly and easily and tucked myself a bit down but not too much. I
swallowed and went back to the kitchen where she sat sipping coffee.
I cleared my throat and waited as she turned and looked.
After a moment she said, "That is a beautiful set and the panty fits you
nicely. Come closer."
I moved to her and she placed her hand on my bare thigh. "And you
shaved! You look adorable!"
I blushed more and muttered, "Thank you."
She measured me and told me that I was right, a 36, but then added, more
a b cup without pads, and definitely a size 6 panty. "You know if you
had bigger breasts you would have a figure any other girl would envy."
I said nothing as she handed me the tape back. I turned to leave when
she said, "Bill, since you have them on, why don't you leave your set on
for the rest of the night? I mean just slip a shirt and pants over it.
Ok?"
I am not sure if she saw me nod or not. I put the tape away and put on a
pair of man's jeans and a golf shirt before returning and starting
supper. We did not speak of it again the rest of the night. I slipped
them off before bed, my head still confused at her new, sort of but not
really interest.
My birthday was on Wednesday and when I came home I could smell dinner
already cooking. I smiled to myself because this was the only day all
year I did not have to cook. Mary greeted me with a smile and a kiss and
then said, "We have about an hour and a half until dinner. Why don't you
go shower and I will make you a drink? Oh, and shave real, real close
and I mean everywhere!" She giggled and added, "I left a bathrobe on the
bed for you to wear when you get out of the shower."
She turned back toward the stove as I headed for the bedroom, happy, a
little confused by her attitude and wondering what she was up to. Then I
remembered her comment about getting me a corselet. Oh God I thought,
had she really done it?
The robe on the bed was light blue and a moderate length; there was
nothing either feminine or masculine about it. The material was a bit
silky and a little thin. I put it down and started the shower. I had
shaved rather close the day before so except for making sure my guy
whiskers were done there was not a lot to do. I stepped out and used
deodorant, slipped on the robe and padded barefoot to the kitchen.
Mary heard me despite my soft steps, turned and said, "Oh good it fits
nicely."
She handed me my drink and we discussed our day, ignoring the fact I was
naked under the robe and she was fully dressed in a smart and for her
revealing work outfit. I asked if she had worn it all day and she told
me she had not, in fact wore her regular, dowdy stuff as she put it.
She told me she had decided to look more feminine for dinner and then
slyly added that she even had stockings and a garter belt on underneath.
I was shocked. She had not worn them in years as far as I knew and to
openly tell me, it was like she was flirting or teasing me. Mary knew I
was clean shaven and naked under the robe and for her to comment on her
choice of lingerie is something she may have done years ago, but baffled
me as to why she had said anything now.
She must have seen the surprise and confusion on my face because she
reached across and stroked my thigh a bit before adding, "I just wanted
to be as feminine as I could for you on your birthday, especially given
my lack of interest these last few years. I also wanted you to be a
comfortable as possible when you open the gifts I got for you're for
your birthday. And I thought if I had on some sexy lingerie, you may be
less shy to try on your gifts in front of me instead of alone like you
usually have to."
As she finished and pulled her hand away, I realized several things, she
was flirting; although how far she would go was unknown, she had in fact
gotten me some sort of lingerie as a gift and that I still desired her;
my cock was full and thick and evident in the tenting of my robe.
As I picked up my drink to go to the living room I saw her try to hide
her smile, even as I tried to hide my erection. I sipped my drink and
wondered about the odd changes happening, tried to sort it out and
decided it really did not matter. She loved me and I loved her and that
is all that mattered.
Mary refilled my drink and told me dinner was about forty-five minutes
away. She and returned a moment later with several white, unwrapped
boxes from a very expensive lingerie store in our town.
As she set them down on the table before she said, "I was hoping you
might wear these for the rest of the night, um, your choice of course."
I wondered at the nervousness in her voice, the uncertainty. It matched
my own that is for sure.
"This one first please Bill," she said, still sounding unsure.
I took the box from her my hands barely shaking. I set it down and
lifted the lid off, nervous and oddly pleased the tissue inside hid the
treasure. I folded the tissue aside to reveal a pair of ivory colored
panties. They were lightly graced with lace, sensual in an elegant but
not trashy way.
"Do you like them?" she asked, in a way I thought quite shy. I nodded
and reached in to remove them from the box, my fingers tingling at the
touch. I drew them up and out. They had elastic leg openings and waist,
were full coverage front and back and they glimmered in their softness.
I was speechless.
"Put them on under your robe Bill," Mary spoke quietly.
In a trance, I stood and bent down, bunching the silk in my hands,
stepping one foot and then the other through the leg openings before
drawing them slowly up my shaven legs. My cock could not get harder than
it was, but it tried.
I adjusted them with a tug or two and looked at Mary. "Thank you," I
stuttered.
She smiled and asked, "Do they feel nice?"
"They feel....beautiful," I answered.
"I got one that would hold you, um, either up or down, I was not sure if
you still, you know. got that way." Again she seemed embarrassed by her
participation.
Coughing she said, "Well then, there is this," handing me another box,
heavier than the first. I took it and sat down again.
Opening it with hands that now obviously shook some and inside found the
thing I had confessed to having been afraid to buy for myself; a
matching corselet. It was the same color and material as the panty but
except for the sheer cups, solid to look at. How beautiful I thought.
Now Mary stammered a bit, "I will have to help you a bit, I mean it
laces in the back but hooks in the front. Do you think I should help?"
My turn to stammer, "Yes, Mary I would like that, like it a lot."
I handed it to her and stood. I slipped the robe off my shoulders and
let it fall to the floor. I stood before her in the panties she had
given me, not sure if she wanted to see my aroused state in them or not.
I thought I heard her gulp before her business sense took over and she
said, "Turn then."
I turned and shivered as she slipped the garment over my shoulders from
behind and asked me to hook the front. When I finished she laced the
back, not tight but comfortably snug. When she was done, I felt rather
than saw her step away and sit down.
"Slip your garters through your panties Bill and then look in the box
again." I heard her say. I followed her direction, twitching when my
hand brushed my member. In the box I found sheer white stockings.
Mary sat on the couch and asked, "Do you mind if I watch while you put
your stockings on Bill?"
I looked at her and thought I saw, well, not lust but interest. I told
her I would welcome her watching as I pulled the stockings from the box,
separated them and then rolled and slowly pulled them up my legs. I
admit that I was a little flirty as I slipped the tabs of the garters
into their holders and adjusted them so the seams were straight. Not
sure what Mary's motivations were, I had at some time decided to accept
the pleasures of the moment.
"Why don't you open the last box and then slip into your robe again
Bill, while I go get comfortable and then we can have dinner." Mary said
as she stood.
"Ok," I whispered as she left. The last box contained a pair of ivory
colored mules, complete with a two inch heel and feathery material on
the toe bridge. I slipped them on as I wondered what getting comfortable
meant and again wondered if maybe her interest was coming back.
As I slipped my robe back on, Mary returned and "getting comfortable"
turned out to be without her blouse and skirt. She entered the room in
her black stockings with the promised garter belt, beautiful above her
black heels, a black lace bra and panties, covered by a sheer black lace
teddy. Over it all she had put on a black silk robe.
"Ready to eat?" she asked in a teasing tone.
Dinner was as normal as any we had ever had. Neither of us mentioned the
fact that we were wearing the silkiest of lingerie, nor did it seem odd
that my wife would be chatting so comfortably with me as my cock
strained against the slippery nest of the panties she had given me.
I guess because we were behaving as if we dressed this way together all
the time and the fact that neither of us mentioned it as we ate, I did
soften a little. Not completely because the panties were of the softest
I had ever felt, but some. As I bent over putting plates in the
dishwasher, my thin robe tight across my bottom, I heard Mary say, "You
do have a darling ass and great legs you know Bill." I hardened fully
again.
After the kitchen was clean we sat in the family room quietly watching
television. As the evening drew to a close, Mary patted the couch beside
her, inviting me to sit near her. I moved closer and sat, our thighs
barely touching.
"You know I love you don't you Bill?" she asked shyly.
Surprised by the question, I immediately responded, "Of course I do, I
have never doubted that."
"Well I know that I have not been there for you in recent years," she
sighed.
"Yes you have, we have always been there for each other," I answered.
"I meant sexually, Bill. I was hoping that the outfit I got you would
not cause you to become aroused. I guess I thought if you no longer
responded, I would not have to feel so guilty."
I stammered, "But Mary it is not your fault that you, well you have a
lessened desire. It certainly is not your fault that I still get
aroused! It is just the way it is."
She reached across my lap and gently stroked my hard cock through the
panty. "Still, I know you are disappointed not to have help getting
relief."
I moaned very quietly at her touch but did not comment.
She continued to lightly caress my cock, sliding her open palm up its
length. She smiled, "Do you remember when we used to use the strap on?
How we pretended I was the male of the house and you were the hired
maid? You would bring me my drink and pretend to clean the room, bending
over to show your behind and stockings."
"I do, I remember," I said, breath coming a little quicker.
"I always enjoyed that." she continued. "I also always wondered if you
were thinking of the strap on as a real cock, you know, flesh and blood,
jutting out from a real male. It is ok not to answer, but did you?"
I wanted not to answer, but I also wanted her to keep teasing my aching
cock. "I did, but not a cock on a real guy, I mean a macho guy. I
sometimes thought of another cross dressers cock, I guy like me that
likes being dressed." I blushed furiously at this confession.
"Oh my," she laughed, "That never occurred to me. So a cock excited by
lingerie excites you?"
"Um, yes, well only in fantasy, I mean I would never cheat on you, you
know that." I squirmed at the conversation and her constant gentle touch
on my cock head.
Shifting the topic Mary suddenly asked, "Bill do you have any condoms in
the house?'
Confused I said, "Well yes, I use them when I, when I. well it keeps me
from ruining my panties." Again I was blushing bright red.
"Go get one please," Mary stated.
Even more confused by her motives now, I quickly retrieved one from the
bedroom and returned. While I stood before the couch, she asked me to
pull my panty down, slip the condom on and then pull my panty back up.
As I did as she asked, I saw her staring at my hard cock. She motioned
for me to sit by her again when I was done.
As I settled next to her she placed her arm over my shoulders and used
her other hand to gently rub my nipples, both equally as stiff as my
cock. "I had forgotten what a good size cock you had," she commented.
The hand brushing my nipples trailed down my belly and back to my cock.
As she gently grasped it she asked, "Do you still fantasize of being
with another cross dresser?"
I nodded as I murmured, "When I am, well, you know, masturbating."
"Do you imagine him sitting next to you on the couch like I am? Dressed
in sexy black lingerie and stockings, teasing your cock through your
panties? Like this?" Like this meant rubbing her thumb over and across
the head and then squeezing and slowly pumping me.
"Oh yes." I shuddered.
"What would you be doing?" she asked.
I thought for a moment, my mind distracted by her hand on my cock,
remembering all the times in the past she had played with me. "I would
be touching him that way too," I said.
"Mmmm, and have you ever thought about slipping to your knees between
his legs? Sliding his panty down to touch his naked cock?" Mary asked.
At her continued touching and her question, I felt my balls tighten. "Oh
Mary," was all I could say.
"Maybe leaning in and licking him? Taking his cock in your sexy mouth?
Cupping his balls as his hardness slid across your lipstick? What do you
think Bill? Would you like to do that?" Mary persisted.
I know Mary felt my reaction to her words transmitted from my cock to
her hand, but still I found myself answering aloud. "Yes, I have
fantasized about that, but I would never actually do it. I would never
betray you.' I moaned as her fingers reached further between my legs to
tease my balls.
"Mmmm, but it would not be cheating if I was there watching you suck
cock would it Bill? Or watching you take his cock in your ass? I know
you loved the strap on sliding in and out of your ass," I heard her say
through a mind fog.
My cocked throbbed in her hand and I knew I could not lie to her.
"Mary," I whispered, "you want to, to watch me with another cross
dresser? You want me to have sex in front of you with a stranger?"
"I want you to be happy Bill. I know masturbating can not be that
fulfilling and if you have that fantasy I am ok with it, as long as I am
there as your safety valve." Devilishly smiling she added, "Besides I
may even get horny enough to let you both do me."
"Mary I don't know, I mean I do not want you to think I am gay or. I
don't even know another CD," was all I could think to say.
"Maybe you could meet one online," she said as her hand began to grip
and relax on my still panty covered cock. "Someone close by and that you
found attractive in a girly way. Someone like you that may be lonely and
dreams of being with another panty-boy."
I guess I gave in, I don't quite remember. I do remember opening my legs
further and her hand caressing my balls. I remember cumming very hard in
the condom as her lips came down and sucked one of my nipples through my
lace bra.
Friday morning before she left for work, Mary kissed my cheek and said,
"Really Bill, if you want to invite a cross dresser over to play in
front of me, I am 100 percent ok with it."
"Seriously?" I asked.
Mary laughed. "Stop saying that!"
Latisha
- 15.11.2022
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