Derry Helps with a Yard Sale
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Derry Finds His Way free porn video
Derry Finds His Way
By Trisha Gilbert
CHAPTER 1
Derry was happy to escape the house and his sisters and do the chores at Ann's
house. Ann was the nurse who had stayed at his house when his mother had been
suffering from some type of internal problems that had not been discussed with
him. He liked Ann a lot because she was very reserved and serious, unlike his
screamy-mimi sisters, and she dressed in simple clothes (when not in her
regulation nursing uniform).
Typically at Ann's he helped her with projects like rolling up rugs and taking
them outside to be beaten. Today, however, Ann asked him to clean out the
contents of the basement, moving everything that was not junk to the garage, and
putting the junk out for the trashmen. She planned to paint the basement so that
it would be a more inviting, attractive space.
The work was grueling. Ann worked along side Derry, and they both worked up a
literal sweat and were covered in a thin grime of filth by day's end. It
probably had to do with the coal dust thrown off by her ancient coal boiler. At
lunchtime, Ann had brought food out back and the two of them sat on the cool
grass at the rear of her house.
"Well Derry, you are a sight." Ann laughed. She pointed out how the mask of dirt
coating him was broken where he flexed his elbows and along lines at his neck.
Derry kind of liked the ribbing from Ann, because it was gentle and well meant,
and it was a form of attention. He liked her, and he liked to have Ann pay him
attention. She had washed up to prepare the sandwiches, and her hands were clean
up to the elbow.
At about five, Ann excused herself to go and clean up, while Derry lugged the
last items in the backyard to the garage. The basement itself looked wonderful.
Then Ann called to him from upstairs, and he dropped the broom and went up to
her kitchen.
Ann was radiantly clean and freshly dressed in a denim skirt and sleeveless
white cotton blouse. She moved quickly around the kitchen, making preparations
for dinner. Derry loved the way she looked--her clean, smooth brown hair, her
wonderful face without a bit of makeup, her smooth tan legs and simple sandals.
Her hair was swept up at each side and held by a barrette--Derry loved her old-
fashioned look. He felt embarrassed he was so dirty and sweaty--he would not
even sit in a kitchen chair when she urged him to.
She asked if he could stay for dinner and he gratefully accepted, saying he
would call his Mom but he was sure it would be fine. Ann moved by Derry to place
two settings at the kitchen table, and Derry glanced her way. He thought his
heart would stop. Without knowing clearly how he knew, he realized that Ann was
not wearing a bra. As she arranged the table settings two feet in front of him,
Derry could look at her side, beneath her arm as she stretched forward, and saw
the side of her torso--and a lot of space between her torso and the armhole of
her white blouse. It was rather thin material, but it kind of buckled away from
her body as she moved back and forth. She then sat at the table and placed the
palms of each hand on a thigh, her elbows spreading outward somewhat like wings.
At this moment, Derry could clearly see the underside of Ann's left breast.
It was beautiful. Her breast stood clearly away from her body, but with a gentle
swoop that created a crease beneath. Derry could not see the tip of her breast,
but he knew that he would be able to under the right circumstances.
Derry was frightened. He did not want Ann to become aware of his eyes on her. He
felt for sure that she would be upset by his interest, even though he was only
eleven. It wasn't like being an infant or toddler, whose unapologetic curiosity
about the body could be viewed as innocent interest.
When Derry was upset or confused, his solution had always been passive, to do
nothing until a path appeared. In this case, remained rooted to the spot he was
in, but studiously avoided continuing to look.
Ann spoke. "Derry," she smiled, you are a sight. I don't think I've seen such a
dirty specimen in a long time, and I work in a hospital. I just cleaned up and
wasn't half as bad. You really did the hard part, and I really appreciate it.
What are we going to do? You can take a quick shower before dinner, but you can
get back into those jeans or that shirt. Even your underwear must be a fright."
Derry had no idea what was coming next. He had been thinking he could ask to
wear a sweatsuit he had seen hanging in the cellarway, but he thought suggesting
it would be forward. He would feel awfully funny in her clothes, especially when
he didn't have underwear on.
Ann went on. "I have it." she said. "You'll have to be a bit discreet Derry, but
the nurse who stayed here for her first semester left some clothes when she
moved to New York, and you could use some of them. Promise you'll never tell her
or your parents?"
Derry thought this was a little strange. He was the one who would be embarrassed
by the disclosure that he had worn a woman's clothes, no matter how innocent the
circumstances. But he felt that Ann was smart and that he should follow her
lead.
"I promise." he stated soberly. Ann then led Derry upstairs to Minae's room. He
could think of nothing but the body in front of him, the smooth tan legs that
disappeared up under her skirt as she moved up the stairs. Although Derry could
see nothing, he could imagine Ann's bare legs, without socks or stockings, and
how they rose under her skirt naked to her torso. He correctly assumed she was
not wearing a slip.
The petite Japanese nurse who had occupied this room was close in size to Derry.
Ann moved to her dresser and pulled out a set of khaki shorts, a sleeveless
pullover, a pair of yellow cotton panties, and a set of slip-on Japanese
sandals. She laid them out on the bed, and then led Derry into the adjoining
bathroom, which obviously had just been used by her due to the evident moisture.
Explaining where the towels and shampoo were, Ann departed.
Derry was dumbstruck. Without any discussion, Ann was assuming he would dress
like a girl for dinner. The thought panicked him, because it thrilled him. He
quickly washed, dressed, and trotted downstairs.
Ann made no comment on his appearance, except to ask him to pull the blouse from
out of his shorts, explaining that it was supposed to be loose on him and
thereby emphasize his slimness. She served their meal, and they ate and
discussed the day's project.
When they were finished with the meal, Ann offered to comb out his hair, which
was fairly curly and about the same length all over his head. He agreed, of
course, enthralled by Ann's interest in him and his appearance. As she moved
around him with the brush and comb, Derry could not bear to avert his eyes from
the armholes of her blouse, and the body within. He could see one breast at a
time, wobbling faintly as she raised and moved her arms and leaned toward him,
then away. She propped her arms on her hips enough times that Derry began to
wonder if she was aware of what was being exposed. But he couldn't believe it
because she made absolutely no reference to the situation. Although he could
clearly see each dangling breast as it stood away from her chest, he wanted to
see her nipple.
As she finished working on his hair, a knock came at the back door, and Ann's
neighbor walked in without further ceremony. It was Mrs. Cobbles, who Derry knew
only as the wife of the town's most important surgeon. She was a cheerful
looking woman of about 50, with a classic hourglass figure and slim arms and
legs.
"And who is this Ann?" she exclaimed? "Minae's replacement?"
"Oh this is Derry, who may want to become a nurse one day but certainly hasn't
set career plans yet. We worked on the basement all day today, and just cleaned
up for dinner."
"I saw all the junk out there. That's what attracted me in fact. Do you think I
could scavenge a few things? Would this cute little lady help me lug them home?"
Derry gulped. He didn't know what to do. He looked so much like a girl in the
sandals, sleeveless blouse, and non-zippered, flared shorts that Mrs. Cobbles
had assumed as much, and there was no un-embarrassing way to explain his dress.
Ann seemed to understand, and to play along.
"Helen, Derry would be pleased to help I'm sure. Just push any big things for
the men to handle if you select something." Ann had clearly implied Derry was a
girl.
So Derry went outside with Mrs. Cobbles to the curb. He felt frightened and
wonderful. Something about being in these clean, simple, female clothes and the
feminine sandals absolutely gripped Derry. And he was out in public in these
wonderful clothes.
CHAPTER 2
Mrs. Cobbles did find several things she wanted from the material at the curve,
but they were all small enough that Derry had no problem carrying them over to
her house next door. The doctor evidently wasn't there. Mrs. Cobbles offer Derry
a soft drink or ice cream, and he accepted an ice cream cone.
"Well Derry, I appreciate this a lot, getting help on the spur of the moment. I
wonder if I could presume just a bit more? I manage the hospital's thrift shop
downtown, and I've been trying to get some tables and bookcases moved for weeks.
With you there, we could do it together easily. What do you say? It's only a few
block's walk."
Once again Derry took the path of least resistance and said he would certainly
help. Mrs. Cobbles called Ann to let her know and they were off.
At the store the work was quickly accomplished. It really seemed like Mrs.
Cobbles could have done it alone, but she obviously enjoyed showing the place to
Derry. She pointed out the women's' and girls' section to him, obviously still
mistaking him for a young adolescent girl. She suggested he look through the
nightgowns and bathing suits because they were such bargains, but Derry said no
thanks.
"Derry, do you go to the parochial school?" she next asked. He said he did, in
fifth grade. She triumphantly went to her office and returned with a plaid
jumper and white blouse, which she explained, had just come in that day, freshly
cleaned, and she was certain it would fit Derry. "Why don't you try it on?" she
asked, "Your mother would really appreciate you're getting a practically new
outfit for $7.00.
Derry didn't know what to do. Refusing could certainly bring attention to his
problem, and she seemed pretty insistent on actually making this a gift of
thanks. So Derry agreed.
In front of Mrs. Cobbles and right in the aisle, Derry first dropped his shorts
and then pulled the sleeveless top up over his head. There he stood, his flat
narrow chest shining and not a stitch on except Minae's yellow panties. A small
bulge poked out in the crotch area due to his penis, which was not erect but
felt wonderful nonetheless. For some reason, Derry was enjoying his virtual
nudity in front of this 50-year-old, matronly woman, her easiness in front of
him, and the fact that he had pretty cotton underpants on, with a narrow elastic
circling his narrow waist and holding them up.
Mrs. Cobbles helped him first with the blouse and then the plaid jumper. They
did fit well. Mrs. Cobbles was very pleased. Derry's slim legs peeped out from
the skirt at about knee level. A light dusting of body hair showed on his legs.
Mrs. Cobbles suggested that he put on some suitable oxfords as well, with white
cotton anklets. He simply looked great. She suggested a bracelet, simple gold
chain necklace, and barrette to help him "look grown up" in her view, and he
acceded to this as well. She topped it off with a nice small clutch for a purse.
Mrs. Cobbles suggested walking the short way to the hospital to see if her
husband was ready to come home. This meant walking up the street in a dress but
Derry was strangely pleased and excited by the prospect.
Mrs. Cobbles hesitated. "You know, the minimum age to enter the hospital during
non-visiting hours is still 14, although we've tried to get a change. You look
so young in that outfit; I'm going to suggest one more "improvement". Why don't
we find you a training bra so that it will show through and everyone will think
you're developing. That will get you in, no question."
Derry agreed. He loved this. He feared slightly being seen by someone who knew
him, but the thrill of masquerading as a young girl and entering the woman-only
hospital was overwhelming.
"Well, there surely are enough possibilities here" Mrs. Cobbles laughed, combing
through the hundreds of bras in the girls' section. Soon enough they found a
simple, white training bra with a bit of padding in the cups, and Derry slipped
down his jumper top and removed his blouse. Mrs. Cobbles leaned down and slipped
the bra around Derry's waist, then indicated how he should put his arms through
the straps.
"I declare, you look like a 15-year old with a bit of development" Mrs. Cobbles
exaggerated when they were ready. In fact, little of the bra showed beneath the
jumper, but a little did at the back. Derry clearly looked more feminine with
the bra showing through his blouse and the slight swelling at his bust line.
Mrs. Cobbles seemed inordinately pleased by having Derry in a bra.
They left the store together. They entered the hospital across the street, Derry
very aware of the "exposed" feeling of having air swirl around his bare legs and
knowing that his cotton underpants were all that stood between him and the
outside world. He carried a bag with his shorts, sandals, and sleeveless blouse
for the trip home.
Inside, everyone seemed to know Mrs. Cobbles. They were directed to a ward where
her husband was completing rounds. They found him consulting with a nurse over
an evidently anorexic young woman, propped up in her bed for an examination.
"Hello there young lady" boomed out Dr. Cobbles. "Holly, your goal is to look as
well rounded and developed as Derry here."
The patient did not even look Derry's way. Derry, however, went towards her and
looked her over. She was in nothing but a paper examination outfit that was wide
open in the rear. Derry could see her backbone protruding clearly, right down to
her buttocks, which seemed non-existent.
Derry could see down the front of Holly's outfit. Two tiny, protuberant breasts
dangled loosely on Holly's chest, wrinkles showing in the front around the
standing nipples due to the significant shrinkage they had suffered. Derry was
very excited. He looked again, and realized he could see down to her crotch, and
could even see her largish labia, which protruded from the emaciated crotch.
Dr. Cobbles asked the nurse to put Holly on a bedpan to see what she might be
able to evacuate. Risking whatever Mrs. Cobbles might think, Derry kept looking
as Holly's covering fell away, and her bony genital area was exposed.
"Try urinating dear' said the doctor. Holly did, and a thin, yellow stream of
urine exited her body, splashing into the pan.
To be continued...
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