Derry Finds His Way
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Derry Helps With A Yard Sale free porn video
Note to readers: I am inspired by Pamela's wonderful "Mrs.
Canvendish", which can be found on http://fictionmania.tv. Read
it and you'll love it like I do. Please encourage her to continue
this un-completed tale, as I have.
It is the gentle, non-sexual story of Matt, a young man going it
alone in life (a bit naively). He becomes gardener-helper-maid to
the elegant, living-alone Mrs. Cavendish, who is fascinated by
his long "not neat" hair, and insists on brushing it for him and
putting it up in a bun--and it just happens that when he stays
for dinner one evening at her invitation, that he showers and she
sets out a clean set of her clothes for him to wear. This story
is a true inspiration to good writing.
I'm always slow to get these done, so here's another installment
that isn't "finished" in the sense it should be. I will add more.
Derry Helps with a Yard Sale
Trisha Gilbert
Chapter Five
"Oh Derry, I'd like you to do my sister a real favor, if you
would. She's a nurse too." Mrs. Marshall seemed friendly about
her request, but she also sounded like she expected a "Yes".
"Sure." Derry replied, not certain what he might be getting into,
but just allowing things to take their course, as he typically
did.
Derry was the new male nurse at the Marshall's, and things there
were just a bit strange. Because he had replaced a female nurse
who'd decamped after just a few days on the job and with no
notice and none of her belongings, Derry had ended up making do
with her uniforms to the extent he could, because his own
suitcase had been lost at the time of his arrival.
This meant that Derry was wearing a woman's nursing pants and
tops on a daily basis, and actually her underwear as well.
Inexplicably, this pleased Derry. He did not know what excited
him so about the arrangement, although some of his growing up
experiences had involved being in girl's clothes, but for several
days now he had gladly donned as much as he could of his
predecessor's outfits. This meant pants and top, panties (full-
cut, pastel cotton briefs), and white oxfords and nylon
kneehighs. Mrs. Marshall, and his patient Junie (Mrs. Marshall's
anorexic, 19-year old daughter) acted as if there was nothing
strange in all this.
"You know we are a little short of uniforms that fit you." Mrs.
Marshall exclaimed. "My sister needs help preparing for a yard
sale in her neighborhood--it's kind of a community thing, and it
would be best if you went in 'civvies', know what I mean?"
"Not really." Derry admitted.
"I mean, even though she's a nurse too, aren't there some shorts
or jeans among Amy's things that you could wear instead of a
uniform?" asked Mrs. Marshall, a little as if she thought there
was a shortage of brainpower at Derry's end.
"We'll, I'll see." Derry replied. "I'd be pleased to help."
Later that morning Derry did return to his room, and he looked
through all the clothes left by Amy. He found plenty of shorts,
but they sort of advertised "feminine" because of their flared
look, the elastic tops, the lack of a fly in front, and the fact
that quite a few were white. He didn't thing boys wore white
shorts, except for tennis.
He also spotted several pair of jeans, and he gave them a try.
Amy had a nice pair of Levi jeans, and he correctly guessed that
they were for girls only, probably teens. However, he could
already feel the thrill of perhaps wearing these out in public,
in front of others than Mrs. Marshall, who so readily embraced
his wearing feminine gear. They fit just right. In fact, his rear
pressed into the rather narrowly cut jeans quite attractively,
and the panties he wore (Amy's full cut briefs) showed through
faintly. Awesome.
At just that moment, Mrs. Marshall knocked and asked if she could
come in. He said she could, of course, and the next thing he knew
she was assisting him in choosing an outfit.
"Derry, you do look just terrific in Amy's uniforms. I'll bet
these clothes work as well. I hope you don't mind that they may
cause some confusion about you're being a boy from people who
don't know you. My sister Suze knows you're a guy, so that'll be
no problem for her."
Derry shrugged. He actually thrilled at the idea of wearing these
"civvies" and being mistaken for a girl. He did note that, even
though he was 22, Mrs. Marshall regularly referred to him as a
boy as opposed to a girl, not a man as opposed to a woman. This
was somehow just right too.
Mrs. Marshall said, "I would recommend the sandals with those
jeans, you'll be working hard at moving things for the yard sale,
so slip-ons won't do. Why don't you just carry sandals in case
there's something social after the work party. I'd wear these
sneakers if I were you."
Derry blanched. This was s tough one. The cute white sneakers
Mrs. Marshall referred to could not be mistaken for men's
sneakers, running shoes or otherwise. They were clearly women's
Keds of the most traditional type. And they had pink laces!!
Yikes!! And for a 22-year-old, they gave off a definitely non-
vampish, girlish look.
Without waiting for a reply, Mrs. Marshall started to discuss his
top. She said, "You know it's hot and you'll be working hard.
What about a tank top? Amy has a few here."
Derry loved this. He had a slender torso and arms, and he thought
he looked great in a tank top. But he had always feared as a male
that some bully would notice him and pick a fight or at least
cause a humiliating moment about his lack of physique.
The only trouble was the lavender top that Mrs. Marshall was
holding up was not "unisex" in any respect. It was soft pima
cotton, had a light scalloped edging along the top above the
bustline, and very thin loose straps.
Nonetheless, Derry was going to do it. "Sure." he said, reaching
for the tank top.
She said, "Let me help."
She stood behind Derry, now outfitted in woman's panties and
jeans, and she put the tank top over his head and up stretched
arms. He fitted his arms trough the gaps properly, and Mrs.
Marshall pulled it down over his torso. It looked great.
"Derry, I just marvel at how well you can adapt Amy's styles to
something workable for a boy. You really are the cute-est thing.
I would love to give you a bracelet to wear with this."
"Well," said Derry, "even though your sister knows the story, it
might be better to not confuse other people and just add the
bracelet to prevent ambiguity. You know the thing I hate the most
is when people debate whether I'm male or female. It happens too
often, and it's much better to ward that off."
In truth, Derry was still concerned in the back of his mind that
some jerk, with more muscle than gray matter between his ears,
would make a point of Derry's look and humiliate him.
Mrs. Marshall smiled, knowing she could, and over time would,
help dispel doubt as to Derry's gender. "Derry you're right. I'll
loan you a simple gold bracelet. Let's make sure your hair looks
good too."
Mrs. Marshall got the bracelet and a teasing comb from her
bedroom (Derry has still not seen her bedroom) and went to work
on Derry's hair. She circled him and primped his medium long,
springy locks so that he easily could be a girl with an easy to
manage, summer cut. His ears nestled in the hair along the side,
but they were still evident. Mrs. Marshall's mind moved to
earrings, but perhaps that was pushing it. The bracelet went on
his left wrist.
And so it went. The two of them accepted that Mrs. Marshall's
sister would be expecting a man (or boy) but that Derry would
show up quite convincingly female.
Chapter Six
Derry was welcomed warmly into the Grovenor's kitchen. Mr.
Grovenor was just leaving for work, and the Governor's elder
child, daughter Anne, was preparing to go to work at the health
club.
Derry could not determine whether the Grovenor's younger child
was a boy or girl. Chris was an engaging kid or perhaps 12, who
seemed entirely comfortable with welcoming Derry into the
household.
"Derry, why don't you get a bagel and some OJ." suggested Mrs.
Grovenor, "Suze" to her big sister, Mrs. Marshall.
Mrs. Grovenor was extremely petite, and seemed to have a child's
body though she was twice a Mom. She was wearing a sundress and
seemed quite dressed up for the day ahead. Her hair was short-ish
and swept up away from her face in a pleasing, almost male way,
and she had tiny earrings dangling from her ears. Her eyebrows
were rather prominent, whether true eyebrows or from a pencil
Derry did not know, and she had a fresh application of bright red
lipstick applied. Her eyes were large and luminous blue.
Strangely, she could not be African American as was her "big
sister" Lea, for whom he worked. This would take some
explanation.
Mrs. Grovenor's sundress was a simple cotton print, with a
halter-style top that went around her neck and crossed her slim,
girlish chest. Derry could not see her breasts, but he surmised
that they were small, well separated on her chest, and rather
droopy. Her hem stopped well short of her knees.
Derry obliged her suggestion for some breakfast, and sat at the
kitchen table with his bagel and cream cheese. In front of him
was a pile of laundry that had just come from the dryer.
"Chris, please sort this load of laundry." said Mrs. Grovenor.
"Derry, perhaps you could help. The fact is that most of the help
I need today will be sorting used clothing contributions for the
yard sale tomorrow. The neighbors all divvy up the work, and we
have about eight or 10 tables each spring and fall. It's very
popular."
Derry was pleased and amazed. He had no idea what sorting was
involved, but it was clearly Mrs. Grovenor's underwear, along
with her daughters, or was it her daughter and son? Though it
wouldn't interest him, presumably Mr. Grovenor's underwear was
included as well.
"Chris can start and give you the picture. Mr. Grovenor's will be
obvious. Basically, I wear the full-cut briefs and Anne wears the
more exciting cuts--plus those are all her bras, cause I rarely
wear one--just not much to support." she smiled.
"So Chris's underpants aren't here?" asked Derry.
"Oh sure, but he wears our castoffs, so just ask him or look for
the faded items. Our sizes are pretty much alike and fit him
fairly well."
Derry was dumbfounded. Here was Mrs. Grovenor readily
acknowledging that she dressed her 12-year old son, at least in
part, in her own panties. Chris seemed totally unperturbed by
this announcement to a perfect stranger.
Derry did his best to react in the same spirit. He gestured
silently for Christ to begin. Chris held up a pair of powder blue
hi-cuts. "I just got these from Anne. She likes to wear cotton
only in the summer, and I got a bunch of these.'
Derry nodded, and picked up a bra off the pile. I was a fairly
skimpy, unshaped bra in nude. Mrs. Grovenor said, "That's one of
mine Derry, for when I need to show a bra through my top in the
interests of so-called 'modesty'. Except for my prominent
nipples, I would have no problem 'going without' all the time."
She stood up to display her micro-breasts for Derry's inspection.
"See what I mean? No protrusions at all, except for my nipples."
In fact, her small drooping breasts did poke out the top of her
sundress, and Derry felt it necessary to say something.
"Yes," gulped Derry, "but I do see something. I think they look
nice." He could not believe how easily exhibitionist Mrs.
Grovenor was, especially in front of her son.
Chris in the meantime had started five or so piles, and Derry
hurried to get his hands on the underwear of this relaxed family.
He picked up some white, full-cut Hanes "Her Way" panties and
offered, "These must be your panties, Mrs. Grovenor, because they
look so new."
"Yes indeed Derry." she agreed. "You are really going to be a big
help today, because you're so alert."
"Obviously, Chrissy mostly has the panties that show stains in
the gusset. Those are the ones we tend to put Chris in. But
sometimes we have some favorites we hold on to no matter what, so
feel free to ask as much as you need to. I actually take up a
little in the waist bands of mine before giving them to Chris, so
that will help identify his too."
Derry loved handling Mrs. Grovenor's bras and panties right in
front of her, discussing the stains she had left in the gussets
and her willingness to put her son in her old panties, especially
because she was freely sharing this with an outsider. He had not
even known her 15 minutes ago.
Derry took a chance. He asked "Are you putting any panties or
bras in the yard sale today Mrs. Grovenor? I think they really
look great."
"Well Derry, the answer is yes. And I wonder if you might be a
willing purchaser." She smiled.
"Actually, I haven't been paid, and I couldn't buy anything
today." Derry answered, trying to slip by a direct reply.
"Oh, but you will be paid for your help today, and you could take
part of your salary in merchandize--even chosen before the
customers arrive. So, would you be interested in having some of
my underwear for yourself?"
"Gosh Ma'am. I don't want you to get angry."
Why did Derry feel he needed to explain himself. He risked real
humiliation, yet he felt safe with the exhibitionist Mrs.
Grovenor.
"Even though I'm a boy, I have just tried on some panties at your
sister's because I had to, and they actually feel great. So, yes
I would like some of your underwear to wear."
Mrs. Grovenor smiled broadly. "Well Derry, I think a boy's
private parts go best in the full-cut briefs I wear. But just for
now, why don't you try on a pair of really nice satin hi-cuts I'm
planning to put in the sale?"
She found them in the pile of laundry and handed them to Derry.
He took them to the powder room off the hall and slipped down his
jeans and cotton panties, and slipped on the satin ones. They
shimmered in the light--they were gorgeous. They seemed to be
made of nothing, except for pretty prominent elastic leg bands.
He knew they would show through the bottom of his jeans, and
everyone would know he did not have standard boy's underpants on,
but he looked forward to that. It would help his "disguise".
"Well Derry, if you like them, they are yours. Our prices are
really reasonable, so can choose a lot more."
Derry gulped. "I don't have any need of a bra, of course, but
somehow I'd love to have one you've worn."
"Sure Derry, I know how interested boys are in the underwear of
the opposite sex. Actually, if I were ever to sneak you into my
hospital, I'd recommend wearing a bra so that it shows through
your top. That'd really convince people."
Whew--something more to look forward to!
Chapter Seven
Derry's first assignment was to pick up clothes at a Mrs. Mohr's.
When he arrived, he couldn't get anyone to answer the front door,
so he skirted the house and entered the back yard.
As he pushed open a tall wooden gate that guarded the back yard,
he spotted a swimming pool and three young girls cavorting in it.
They seemed to be engaged in a battle from inflatable rafts being
used as men 'o war.
All three of the girls wore two-piece, skimpy swimsuits, but two
were actually topless. Swollen little nipples pocked out from
their chests, advertising they had all arrived at puberty.
"Hi." one of them cried out, obviously taking Derry's lavender
tank top as proof he was one of the clan. "Are you in the right
place?"
Derry replied that he was looking for the Mohr's to pick up
things for the yard sale.
"I'll get Mom." the same girl cried out.
She had no top on and, at about 13, her breasts were just gently
protruding, though her nipples still remained the dominant look.
Her nipple color was so faint that Derry could not detect where
they left off, but the whole effect was of puffiness. He had to
admit that it looked good and that we was envious.
Mrs. Mohr did not come out, but asked that Derry come into the
kitchen. She was as generous in proportion as Mrs. Grovenor was
slim--her jutting breasts obviously needed the substantial bra
they were encased in. However, her arms and legs were quite
slender, and Derry was attracted to her milk-white thighs and
well turned calves. She had on short shorts, so that Derry could
see a lot of thigh, seemingly practically to her crotch, and her
top was one of those cut-off styles that hang loose above the
midriff. Derry fleetingly dreamed of seeing up under the front of
her loose top at her swelling breasts.
She told Derry that she understood what was needed for the yard
sale due to long experience, and that she had pretty much sorted
her contributions in advance, and packed them accordingly. She
then asked if he had enough time to join her daughter and herself
for a quick swim. The other two girls were neighbors. Basically,
Mrs. Mohr wanted to keep an eye on them for safety's sake, and
Derry could help a lot by agreeing to a quick swim. Of course,
she had referred to Derry as "you" without acknowledging gender.
Derry gulped. He feared what would follow, but he needed to tell
the truth. "You see," he started, "I may look like another girl,
but I'm actually a boy. I don't have a suit that would be
correct."
Mrs. Mohr was amazed. She had noted Derry's Levi's jeans, clearly
the preserve of teenage girls, and had seen the obvious bikini
panty line the boy was displaying. The scalloped lavender top and
bracelet were just icing on the cake. It was hard to imagine he
wasn't a cute, 14-year-old girl.
On the other hand, it titillated her the way Mrs. Grovenor's son
Chris was outfitted in his mom's panties, and she sometimes
regretted not having a son to enjoy in this way. This was her
moment. Furthermore, she was really excited to think that Derry,
once at the pool, would be gazing not only at her own, uncovered
daughter, but also at the seductive but obnoxious Merry Benfield,
from the private school across town that was a feeder to the prep
school in Avendon. Merry showed off constantly and was, in fact a
bit exhibitionist (for a barely budding 12-year-old), but she'd
have no idea she was displaying herself to a male in disguise.
"All we have left is Ginny's one-piece Lycra suit--it's one I'm
putting in the yard sale because she won't wear it anymore. It's
purple, and it will show your hips right up to your waist, but I
know it will fit. Unfortunately it's not lined, and the crotch is
very narrow--so that Ginny can show off a bit of here vulva in
public, if you ask me. You know how naive kids can be. Because
it's stretchy thin material, the cleft in her mons is completely
evident when she's in it. That's an issue right there. How are we
going to disguise your testicles and penis?"
"Here's what we'll do. Ginny has oodles of 'skrunchie' hairstyle
elastics, and some of them have little plastic balls on them to
make them easier to manage. If you're OK with my little
experiment, we'll just gather the tip of your "big man" in one
end of the skrunchie and tuck the other end with the ball into
your anus. This will hold your penis back between your legs, and
I'll bet your crotch will look perfect in Ginnny's suit."
Derry was tremendously excited by the prospect of Mrs. Mohr
manipulating his penis in this way, minimizing his male equipment
for her purposes. Of course, he wanted to join the fun in the
pool too, as a female, but he was more excited by her suggestions
and dominant role. It was as if she had planned this or done it
before, because her ideas were so specific about hiding his
member. So he nodded assent.
"First, put this 'ponytailer' on around your penis and testicles.
Then, tuck each testicle up through the elastic band so that it
leaves your sac and "retreats' into your groin. The ponytailer
will hold the empty sac to your penis, so the testicles will not
descend. The second step is to find a skrunchie with a ball on
it, and to gently let it enter your anus. I can help with that.
Finally, we will feed a rubber band through the end of the
skrunchie elastic and twist it over once, to form a loop, and
then place that loop over the head of your penis. I think it will
grip just fine behind the head.
Mrs. Mohr was right, of course. She found the needed items in her
daughter's bedroom, and then took Derry to the guest room. She
had him lie down on the bed after removing his jeans. Then, in a
pretence of discreetness, she asked him to raise his legs high,
as if getting his diaper changed, and then asked his permission
to raise his panties "just for a sec" to insert the little
plastic ball into his anus.
Derry was in the thrall of this wonderful lady. He didn't feel 22
years old, he felt five, and he felt very much like a little boy
being examined by this mother, not a little girl. He removed his
jeans, he lay down, he raised his legs high and wide, and he
grasped the waistband of his panties and raised them out of the
way.
Mrs. Mohr had a perfect, unobstructed view of the 22-year-old's
anus. It was quite dark, perfectly clean, and surrounded by
darkish skin that continued forward up into his crotch. Probably
the "Mediterranean influence" from his father's genes that gave
him this coloring. Mrs. Mohr was quite awed by the unfolding
events, never imagining that the yard sale could have led to
this.
"Okay, hold on. I'm going to press this little ball into your
anus so gently that you'll not even feel it. It will be just like
when you defecate, and things are going in the other direction."
True to her work, she pressed the little green, sparkly plastic
ball from her daughter's hair-styling aides into Derry' anus. She
moistened it first with spit. Without pushing hard, it took about
20 seconds for his sphincter to relax and admit the ball. To say
the least, Mrs. Mohr was in no rush and enjoying the moment and
the view. It was as if she were finally diapering a boy. It was
that intimate. His little flaccid penis lay at rest.
When the ball disappeared, Mrs. Mohr looked at Derry's face and
gave a nod. He seemed a little spaced out, but acknowledged her
signal and smiled. It was a glorious moment.
"All right, I needed to grasp your 'big man' for a moment, to
attach the rubber band to the new anchor. If this works out, and
you can wear the anchor without discomfort, you'll be well ahead
of the game in the future.
Mrs. Mohr went right ahead and threaded the rubber band through
the skrunchie elastic protruding from Derry's anus, and then,
with a single twist, created a loop that went over then head of
his penis. It snugly grasped his penis and drew it back between
his legs.
"Why, I think you'll be able to urinate with this arrangement
too, as long as you sit down." she smiled. She had already
pressed his testicles up into his groin so that they did not
bulge out.
"Into the suit please. I have it right here. No false modesty now
I imagine." She was enjoying herself a lot.
Derry removed his top. He looked own. His penis and testicles
were simply missing. A tiny puff of pubic hair decorated his
crotch and that was it! This made him tremendously happy, because
he knew now that he could be entirely convincing as a girl, even
a young girl, at least in any circumstance other than nude.
Mrs. Mohr helped him into the stretchy one-piece. While probably
a little small for the diminutive Derry, that only accentuated
the emphasis on a barely covered crotch. In fact, half the area
above his genitals was completely on display. He was lucky his
pubic hair was so limited, because he presented a perfect bikini
line. His penis was pulled back sharply enough that it just
seemed that he might have somewhat more protuberant labia than is
typical in an adolescent.
Mrs. Mohr grinned. "Derry, you truly look great. I would love to
have a son like you who is so adaptable and so damn plain cute.
You're just breaking my heart. One thing though. Your development
up top just doesn't match your labia look, and any girl of 14--
about how you look--should have at least some serious nipples."
"I have it. I'll just get some "butterfly bandages" I have and
we'll tuck them in under your nipples, gathering a little flesh
as we go. This I'm sure will cause your nipples to protrude."
And protrude they did. In the Lycra suit, Derry's every contour
showed--and his new, tiny breasts were the highlight. His
buttocks also looked great in the Lycra, though, as he walked, he
constantly had to pull the seat of his suit out of his crack.
When he forgot, his buttocks glistened beautifully in the morning
sun. And his "vulva" was completely convincing to the girls and
to Mrs. Mohr. She would have to have a friendly conversation with
Mrs. Grovenor's sister about this.
At one point, Derry needed to urinate, and he went into the pool
house. Ginny was there, seated on the toilet, inserting a tampon.
She grimaced and said, "Wait a minute Derry. I'm sure you know
all about the curse."
Derry did in fact because of his days nursing female enlisted
personnel (never female officers for some reason when it came to
intimate matters--he guessed they were able to shield themselves
from male nurses in such cases), and he had occasionally changed
sanitary pads in the case of seriously sick personnel.
Nonetheless, it excited him to have Ginnny seated in front of
him, her knees apart, extracting a tampon from herself and then
inserting a fresh one. She flushed the used tampon, and got up
off the toilet.
"Do you use tampons or pads Derry?" she asked. "I'm kind of young
for tampons, but they are great for swimming, and I swim almost
every day all summer."
Derry hesitated and then said "Pads." because that's all he had
experience with.
Derry then pulled the crotch of his suit aside and sat on the
throne. Ginny wasn't intending to embarrass him, but she saw no
reason to leave Derry alone while he urinated. Modern young
thing, Derry concluded.
So it was "baptism by fire". He hoped that he could urinate with
his penis pulled back, and that the urine would exit easily and
end up in the bowl--not all over him.
It did work perfectly. It was kind of amazing that is his first
effort urinating as a girl, in front of another girl who paid no
attention, came off just right. He was smart enough to do the
obvious and grasp a bit of toilet paper to dab dry the tip of his
penis when he was done. In a way, he supposed, it was perfectly
comparable to a girl gently dabbing dry her labia.
(To be continued)
Charlize
- 07.01.2023
- 30
- 0
