The Purse

By: A Happy Wife

Jim began carrying a purse a few years ago. Actually it wasn't a purse;
it was just a day-timer then it became a man's bag eventually evolving
to a unisex bag. Jim had heard all the teasing from the guys at work.
He had heard his bag called a purse, listened to all the comments about
matching shoes and room for make up. Jim was a good sport and even
enjoyed the good-natured kidding; he bristled inside at some of the
meaner and nastier stuff. The bag was very practical and handy and for
a busy guy who had to have lots of things readily at hand it paid off.
Jim carried a wallet, his cell phone, check book, a PDA and some pens.
If Jim tried to cram all that into his pants pockets he would be
uncomfortable and lumpy. The bag had become a given with Jim and he
always had it with him.

Jim was dating Kathy; even Kathy had teased Jim about his purse and had
asked Jim to carry her lipstick from time to time if her bag was too
full or too small. Jim didn't mind and didn't seem to even notice the
looks he sometimes got from others when Kathy asked Jim for the
lipstick. Kathy did notice and liked the approving looks she got from
other women when her purse carrying man retrieved lipstick from his
purse and dutifully handed it to her and then returned it to his bag
when she was finished. Kathy thought the purse thing was just a little
bit over the top and certainly did nothing to reinforce the masculine
image of Jim. She liked Jim and accepted his not being overly
masculine. They hadn't slept together and she had no plans to even
though she could tell that Jim would jump at the chance.

Kathy and Jim double dated with a married couple once in a while.
Darlene and Milton were nice to go out with. Milton was somewhat shy
and quiet. Darlene was the boss in that relationship and Milton did not
seem to mind the subservient role. Jim had no idea how under the thumb
of Darlene Milton was nor how much Kathy admired Darlene for
assertiveness in the relationship. Kathy and Darlene had talked about
Jim and Darlene wanted to know how serious Kathy was about him. Kathy
had confessed to Darlene that she thought Jim was really cute, nice and
smart but was a bit of a wimp. Kathy was used to more macho guys and
Jim was just not like that. Darlene laughed and said you mean he is too
much like Milton? Kathy just nodded. Darlene said don't worry about
hurting my feelings I know Millie is a pantywaist, I like it that way,
and if you were to work it right you could have it all your way and
have Jim too. Kathy didn't know for sure what Darlene meant but wanted
to know more. Darlene said he already carries a purse let's start
there. Kathy said OK and would let Darlene lead.

Darlene, Milton and Kathy did a little gift shopping for Jim. Kathy was
surprised at Milton's appearance but didn't say anything. She just
looked him over and realized he was dressed in women's clothing. Millie
as Darlene called him wore his gold small hoop earrings, light
foundation, blush and pink tint lip-gloss. Millie had on brown
crocodile print patent leather loafers. Millie wore nude hose and back
zip tan wool slacks with a narrow belt that matched his shoes. Millie
had a silk blouse tucked into the slacks, a gold chain and pendent. He
had on a very feminine wedding and engagement ring set and gold ladies
watch. Kathy couldn't help but smile at the brown patent leather bag he
had tucked under his arm with its short shoulder strap. Millie looked
like a girl or a very sissy boy. Whatever it was cute and really showed
the world that Darlene was in charge and this sissy she had on her arm
would kiss her ass in public and thank her for the privilege. Is this
the plan Darlene has for Jim? Oh well I think I can dig it she thought.

Millie was about the same size as Jim and Kathy knew just about all
Jim's sizes. Millie was able to convert men's sizes into women's sizes
so getting things that fit was pretty easy. Kathy expressed alarm at
the femininity of some of the things they were getting for poor Jim.
Darlene told her not to worry With Millie and her there at the present
opening and subsequent trying on Jim would in effect be ambushed.
Darlene assured Kathy Jim was a sissy just waiting to be developed.

At Kathy's house Kathy just watched as Darlene pointed and Millie
dropped to his knees and removed Darlene's pumps and began to massage
her feet. When Millie was finished he turned to Kathy and offered to do
hers, she accepted his offer and she thought to herself, Jim will be
doing lots of this. Millie wrapped the presents for Jim. Jim was
getting some nice lingerie, a few more purses and matching shoes,
slacks and blouses along with moderate priced jewelry. Kathy was
worried about Jim's reaction to all these feminine gifts, Darlene
assured her it would be fine, Millie didn't say much Darlene suggested
that Kathy give Jim the hand-bags and matching shoes first saving the
red flats and cute red purse till Jim was ready. Darlene reasoned that
if Jim would accept the purse and shoes the blouses and pants would be
easy. With Millie and Darlene both there offering encouragement to Jim
and telling him how cute he would look he would be a pushover. Darlene
told Kathy in private that she might have to promise to sleep with Jim
to convince him to wear this stuff. Kathy laughed at this and said she
had already considered that.


The presents were for Jim's birthday and the small party was at Kathy's
home. Kathy could tell Millie was uncomfortable and embarrassed about
his costume. Kathy thought it was hilarious and made the poor boy do a
little runway show for her and Darlene. Millie was decked out in what
Darlene referred to as serving attire. It was somewhere between a six-
year old girls dress and a French maid's outfit. The dress was pink its
skirt was short stopping well above the knees the two full petticoats
made the already short skirt stand almost straight out from the
humiliated sissy's waist. The ruffled white panties were clearly
visible when the unfortunate sissy moved or bent forward. Millie wore
nude sheer to the waist pantyhose and white one strap Mary Jane shoes.
The dresses sleeves were short and puffed the sissy wore a frilly white
tea apron over this humiliating outfit. Millie was made up and on his
head was a lovely strawberry blonde wig. Millie was adorable and Kathy
gushed over how cute he was much to the poor sissy's humiliation.

Millie just hated this kind of embarrassment and dreaded the moment
that Jim saw him. It was little consolation to Millie that the girls
had the same plan for Jim soon. Millie would be out of sight when Jim
arrived Millie breathed a sigh of relief at that. Millie stood before
the two women and as told lifted his petties and dropped his panties.
Millie heard the sharp intake of breath as Kathy saw the modesty device
that Millie was forced to wear. Kathy started to giggle at the sight of
Millie's little penis all wrapped up in its pink sheath. Kathy knew
that no man enjoyed having two women laughing at his penis. Words like
darling and adorable were not words men liked to have used to describe
their penis. Kathy just couldn't help but use feminine sounding
adjectives to describe Millie's little penis. The sheath wrapped
tightly around poor Millie's' penis and reduced the diameter down to
about the size of a finger. The sheath had a single row of lace at the
base and a full double row at the head, the sheath obviously eliminated
any chance of an erection, which added to the sissy's humiliation.

Millie was shaved and the penis and the testicles appeared child like
and ever so small, almost girlish. Millie stood there and held his
skirt and petticoats up as the ladies heaped scorn and ridicule on his
symbols of masculinity. Kathy felt bad about Millie's' suffering but it
was just too funny and the power the women had over this silly sissy
was intoxicating to her and she wanted it. Kathy had never seen Jim's
penis and testicles and didn't know how they compared to Milton's but
Kathy thought that with that sheath on Jim's manhood could be reduced
to girlhood. Kathy had become hungry for this kind of power. She took
Millie's penis in her hand and could feel the heat coming from it and
she just knew the desire poor Millie felt and she also knew the
humiliation his forced impotence had on the little sissified man.
Darlene said to Kathy, got any ideas? Kathy just smiled and shook her
head yes.

Jim arrived right on time and greeted Kathy and Darlene he asked about
Milton and was told he would be along later. Millie was in a bedroom
sulking from his latest humiliation at the hands of the two women. He
sat on the bed his hands were drawn behind his back and held in place
with a pair of finger cuffs in his mouth was an over sized pacifier. He
had instruction to keep it in or suffer the consequences he didn't know
what they might be but didn't want to suffer them. He could hear the
party begin to start up and heard Kathy go and get some gifts for the
unsuspecting Jim. The first gift Jim opened was a black purse with a
short shoulder strap and a gold clasp. It had a holder for a cell phone
and a mirror inside. It was shiny black not patent but a very waxed
look. It was obviously a women's bag and Jim knew it. Kathy began
pointing out the advantages of this bag and Jim could see that she was
correct. He was worried about the feminine appearance of this purse. To
make matters worse the girls called the bag a purse and wanted to see
him carry it. Terms like so cute and very pretty were flying around.
Jim thought he could carry it when he was with Kathy.

The next gift was the matching shoes. Jim was somewhat taken aback by
them. These were girl's shoes! They were the same shiny black leather
as the purse. They had a thin hard sole with a covered heel about two
inches tall. The vamp was high and the shoes had an elastic gore for a
good fit. These things were pumps and Jim knew it. He looked at Kathy
and Darlene with disbelief. Kathy handed him a pair of knee high
stockings and said try them on! Both Kathy and Darlene stood before Jim
and it was clear to Jim that he had best try on the stupid shoes. He
untied his wing tips and slipped of his socks. Darlene showed Jim how
to put on the stockings and Jim slid on the little pumps. Kathy told
Jim with a smile that the shoes were pant shoes and he would look nice
in them. After all she reasoned Jim was secure enough in his manhood to
apply a little femininity if it worked. Kathy assured him it would
work. Jim was modeling the shoes and bag for the girls when Millie made
his or her appearance.

Jim was embarrassed to be seen in these women's shoes and the purse but
he could only imagine how embarrassed Milton must feel. Jim wondered
how Darlene had gotten Milton to ever agree to this. Milton gave each
woman a small curtsy and then looked down to avoid Jim's eyes. Instead
he saw the shiny toes of his white patent girl's shoes and his shaved
girly legs extending from the skirt of his juvenile dress. Embarrassed
by his own attire and sissy appearance Millie shifted his gaze to Jim's
shoes. Millie was further humiliated at his thoughts. Millie had looked
at Jim's shoes and thought how pretty his feet were and how stylish
Jim's feet looked in those cute pumps. Jim was having his own problems,
as he had become aware of how cute a girl Milton made and how attracted
Jim was to him. Not only was Jim attracted to Milton but Jim couldn't
help but wonder how he might look in an outfit like Milton was wearing
and how it must feel to stand there in front of these two women and
wear it.

The rest of the evening was a blur for Jim. He remembered receiving
many presents and being embarrassed about the femininity of them. Jim
remembered promising Kathy he would wear them. He had made a deal to
dress for her as she wished and she had made a deal to have sex with
him. He was so hungry for sex with Kathy that he would have promised
her his manhood, and he just about did. The sex that night was amazing.
Jim was on his back and Kathy slid her vagina up to his face and
settled over his mouth. Jim had never preformed oral sex in his life.
Kathy was not shy about letting him know her preferences. She batted
his head and slapped him to get him in position and get his tongue
speed where she wanted it. After she had over four orgasms she mounted
Jim and still in the superior position road him until he reached a
quick and draining climax. When she pulled off she remarked that he
certainly didn't have much staying power. She then said men with a
small penis often have that problem. She smiled and said it is a good
thing there is nothing quick or small about your tongue. Jim was given
one of her nighties to wear and she went to sleep. Jim wondered what
had happened he had a ladies clothing selection, been ridiculed about
penis size, how long his erection lasted, been ridden like a woman and
now had on a nightie. Jim remembered the subjugated little Millie and
couldn't help but think he would be taken down that road and he would
be wearing pretty shoes when he made the walk.

Jim stood naked on the small stool Kathy had provided; his penis was at
about eye level to the slightly bent over Millie. Darlene stood beside
Jim with a ruler in her hand. Jim had his hands on his hips and had
been told not to move them. Kathy sat in a comfortable chair and
watched the events before her with undisguised amusement. The women
were dressed for a warm Saturday in shorts, sandals and cool crisp
tops. They had on little makeup and their hair was loose and
comfortable. Both looked cute and athletic for a summer day. Millie
looked cute too and this fact was troubling to Jim. Millie was clad in
shorts, sandals and a cute top also his lightly made-up face looked
surprisingly pretty even with out a wig. Jim was bothered by his
attraction to this sissy. The attraction had not gone unnoticed by the
women and the teasing was unmerciful.

Millie was shaving Jim. The sissy had shaved Jim's body, legs, arms,
and pits and was now denuding Jim's crotch. Every few minutes Jim would
start to become erect and Darlene would smack the offending penis with
the ruler. Jim would say thank you after each swat and that would be
met with giggles from Kathy. Jim and Millie had been told that they
would from now on be assisting each other with their shaving needs.
They were told that each would responsible for the other, they would be
come very close and know each others cracks and crevices very well. In
addition to this indignity they would give each other manicures and
pedicures. Jim had already had a pedicure from Millie and his
embarrassingly red toenails were on display right now. Jim eyed the
little pink sheath with its tiny little lock lying on a table. Jim had
seen Millie's sheath and knew he was about to be put into one himself.
Jim knew that once locked in place any hope of an erection was gone.
Kathy would be the one controlling his penis. He would be in effect a
sissy gelding and would suffer all the humiliation that entailed.
Millie and Darlene guided Jim into the bathtub and Millie showered off
any shaving cream. Jim was bent forward and had his rear cheeks spread
by Millie and any stray hairs were taken care of. Millie carefully
looked over all Jim's private places and at least three more smacks
were required to keep Jim presentable. Kathy had told Jim that his
sexual performance was poor and a period of time in the sheath would
help. Besides she still had the use of that wonderful tongue, and she
said with a smile that if she just had to have a penis she thought she
could find one.

Kathy had the honor of putting the sheath on Jim. There was a ring his
testicles slipped through and the sheath wrapped around Jim's member.
There was lace at both ends and it laced up the top like a little
corset. A portion of the head stuck out beyond the lace. The little
lock prevented Jim from untying the whole thing. Jim knew he could cut
the thing off but dreaded the consequences if he did. The penis could
be drawn back and attached to a short chain on the testicle ring or a
leash could be attached so that his penis could lead Jim around. Jim
was allowed to dress. He was dressed in shorts like the others. His
were pink with white flowers on them. His sandals were white with a
high wedge heel and dainty straps. The top he wore was white and
sleeveless his bra straps were visible. Darlene helped him with makeup
and jewelry. When Jim saw himself in the mirror he looked at himself
and though there was no doubt he was a sissy. Jim picked up the white
purse and held it by the little handle. Darlene and Kathy stood back
and took it in. Kathy turned to Darlene and said I like my males to
carry a purse.