Date: Sat, 13 Apr 2024 06:10:01 +0000 (UTC)
From: J J <cpt.original@yahoo.com>
Subject: Sandy's Journey, Chapter 11

CHAPTER 11: Bobbing for Dicks


We swam back into consciousness about 9 the next morning. I can't tell
you how pleasant it was waking up in the arms of these two beautiful
gurls. Kim and I both wanted to get home and change, but Char held us
long enough to get some hot coffee into our bodies. A quick naked
breakfast of bagels and coffee sufficed to wake us all up. Char threw on
a robe while Kim and I dressed in our clothes from the previous night,
and a round of serious kisses at the door almost lured us back into bed.


Kim's car was there, so we said a long, sweet goodbye in the parking lot.


"This has been very quick, but I'm getting quite used to being with
you," I said between kisses.


"I know," said Kim, "Me too. Just don't get crazy on me and run
away."


"Not today, doll. It's all a big change to me, but you're the kind of
light I didn't know I was looking for."


She kissed me again. "Oh, baby," she sighed. "I promise not to get
crazy on you either. Play it by ear and we'll see where it all goes."


One last kiss, and we each drove off. I can't say I wasn't a little
scared at this point. So many changes in such a short time. I had this
wonderful new girl, and her world was completely outside my previous
experience. Tom and Judy, Kim and Charlotte. I could feel a tingling
where I'd been penetrated, and a warmth inside from the acceptance I'd
felt. I couldn't stop smiling.


I got back to my place and took a long hot shower, made some lunch and
checked my email and the news websites I followed. While I was online I
couldn't resist going to one of the clothing sites I'd found that sold
lingerie tailored to men. I picked out a babydoll set, something
completely out of character for me -- I wasn't the helpless little girl
type. Deep inside me there was still a man. Still, I thought Kim might
get a kick out of it. No top/bottom hierarchy had been established. We
seemed equals, our roles varying by the moment. I also bought some
saucier men's underwear -- thong briefs with enough support to keep my
junk corralled, in shades of blue and grey.


The girls had given me the address of a store where I was to meet them at
3. They hadn't told me what to wear, so I just threw on boy clothes,
jeans and a polo shirt. I checked the route and left in plenty of time to
get there on schedule. They had just told me it was "Bob's place" and
given me the address, no business name. I was a bit surprised to find it
was a thrift store, but it really was named "Bob's Place."


I didn't see Kim or her car nearby, so I just wandered in to look around
and wait for them. It was a fairly large building, with all of the used
clothes and general junk you usually find. I strolled down the racks of
women's clothing. A sheer nightgown caught my attention, and I paused to
feel the fabric when I heard a voice behind me.


"No, no, that's not you, Sandy. The good stuff is in the back." I
looked behind me and immediately recognized Kim's friend Penny, this time
in male form. He was wearing khakis and a button-down long sleeve shirt,
all pressed with perfect creases.


"Hello, Sandy," he said. "The girls told me you'd be coming by and
asked me to take care of you. Follow me."


I followed him towards the back of the store. "I was sorry I didn't get
to spend much time with you last night," He said. "I sort of got swept
off my feet at the club." He turned and smiled, then unlocked a door
marked PRIVATE -- NO ENTRANCE.


Stepping through, I found myself in a whole other section of women's
clothing, but of much better quality. There were racks of dresses,
skirts, slacks, jeans, blouses, and lingerie. "I set this up for girls
like us," Bob said. "Here you can find things in our sizes, of good
quality, and try things on in complete privacy. No one will come back
here except other gurls. You'll find anything you need for whatever level
of dressing you want to try."


"I'll leave you here. Help yourself. There are dressing rooms and
mirrors over in that corner. I'll be back in a while to check on you. If
you need any help, press the button near the dressing rooms -- that
signals me." He put his hand on my shoulder and added with a grin, "I'm
really looking forward to seeing you all pretty."


With that he left me alone, and I heard the lock click after he went out
to the front.


The racks were labeled with both women's and men's sizes, which was quite
helpful. I really had no idea what women's sizes would fit me. I knew I
wasn't ready to dress in public, so I passed by the street clothes and
went to the sleepwear and lingerie section.


Oh, my. Such nice things, so very feminine. I picked out a bra and panty
set in robins-egg blue. Then there was a pretty black set with just a
bare front, no cups. I had a pink set like them at home, but the size on
that set wasn't quite right. There were some lovely garter belts -- I'd
never tried one of these, always wearing thigh-highs that were supposed
to stay up but seldom did. I picked out a couple to match my lingerie
sets. In the sleepwear section I found a wonderful green robe. I needed
something to wear when I was being femme, and my grey terrycloth robe
just didn't do it.


The fitting rooms were large, with great mirrors. I stripped to my skin
and tried on the lingerie sets. The men's and women's size tags were
right on. The black set seemed to push my ass out, which I was sure would
make me popular in any gay club, but the blue set really worked for me.
The blue went with my eyes, and the AA cups felt wonderful on my chest.
The light color panties really seemed to accentuate the curve of my ass.
They really didn't work with the green robe though, so I thought I'd find
a second robe to buy. I tied the sash on the robe and tip-toed barefoot
out to find another. It only took me a minute to find a longer robe in a
better color for the blue. It was kind of sheer, but had great lace
details.


I went back into the fitting room and tried everything on. I was amazed
that my cock wasn't rock hard from the feel of all this soft fabric. I
was glad Kim had sent me here. I kind of wondered where she was, but I
was having too much fun to worry about her.


I had stripped naked again and tried on a low-slung red garter belt. It
felt so nice on my hips, but I didn't have any red panties to go with it.
I wanted to find a pair, so I threw on the green robe and slid out into
the main room.


And immediately found Kim, going through the rack I was headed for. Bob
stood nearby, his greater height looming above us both. Kim was wearing a
sleeveless print blouse over a skirt that was just a bit too short for
the office.


"Oh, my," said Bob, and Kim turned to face me and smiled.


"Very nice, babe!" she said. What's under the robe?


"Not much, I'm afraid," I said. "Should I show Penny?"


Kim looked at Bob, who nodded enthusiastically. I took hold of the robe,
opened it wide, and slid into a slinky pinup pose I'd seen in an old
photo somewhere. My cock flopped back and forth against my thighs before
settling. Kim and Bob applauded, I did a slight curtsy and closed the
robe again.


"I came out to find panties to go with this garter belt," I said.
"Would you care to help me look?"


Bob held put a hand. "I've got just the thing. Stand right there." He
looked me up and down for a moment, gauging my size, then went to the
lingerie racks, returning with a red bra and panty set. "These were made
to go with that garter belt. You try them on while I find you some
stockings. I think you're the same size as Kim."


I took them from his hand, then leaned into Kim for a kiss. She responded
like we were an old couple who'd been doing this for years. She fit so
perfectly against my body.


"Will you do a fashion show for us?" she asked. I kind of blushed and
she laughed at me. "I've seen all of you, and Bob will eventually, so go
ahead."


I went back into the fitting room and changed into the black set, adding
a black garter belt, then put the green robe back on. Kim was sitting in
a chair, and I did my best catwalk performance, swaying hips, opening the
robe in front of her. "Good choice, babe!" she exclaimed. Then I
repeated the performance with the blue set and the blue robe. "I love
that!," Kim said. "I can see you right through it. Very sexy!"


I went back in and changed into the full red ensemble Bob had helped me
put together. I didn't have a robe to go with it, so I stepped out
without one.


"Wow, that is so hot," Kim said. As I posed for her Bob returned with a
package of stockings.


"You look quite edible in that, Sandy," Bob said, and Kim giggled.
Opening the package, Bob held up a pair of black seamed stockings. "May
I do the honors?" he said. There was a chair nearby, and I sat down, my
butt near the edge, and put one of my legs out and up. Bob threw one of
the stockings over his shoulder. Bunching the other up in his hands, he
placed it over my foot and slid it up my leg. He massaged the stocking to
get the seam placed correctly.


His soft hands on my thigh, so close to my cock, had an expected effect.
Putting my ankle on his shoulder, Bob attached the stocking to the garter
belt snaps. Then he grabbed the other leg and repeated the performance.
When he finished, I was almost lying in the chair, my ankles over Bob's
shoulders, and he was caressing my legs. His gaze shifted from my eyes
down to where my cock was stretching the front of the panties.


"I don't know what you think, but this feels wonderful to me," he said.
"This is the brand I usually wear when I want to get fucked hard."


"There's an idea," I almost whispered, and smiled up at him. Bob
dropped my legs and I put my stockinged feet back on the floor and spread
my legs. I looked over at Kim, who smiled at me and nodded. Her hand was
between her legs, rubbing her crotch. I guessed this had been the plan,
and decided to just go with it. The girls had alluded to Bob's giant
cock, and I wanted to find out for myself.


There was already a large bulge visible in Bob's khakis, and I leaned
forward and placed my hand on it. Oh, yes, it was definitely bigger than
mine or even Tom's. I opened my mouth and placed it against the bulge,
breathing out hot air through the fabric onto his rod. A stripper had
done that to me once, and I almost came in my pants. It had the desired
affect on Bob, and he moaned.


I undid his belt, pulled down his zipper, and let his pants fall around
his ankles. Underneath I found hot pink panties, with a thick long cock
pushing out over the top. Reaching around and grabbing his ass with both
hands, I pulled him against my face. I repeated the trick of breathing
hot air through the fabric, starting down near his balls and moving
slowly up to the exposed head, which I kissed repeatedly. Putting my
hands in the waistband, I pulled his panties down over his hard cock and
let them fall down to his bunched trousers. He stepped out of all of it
and kicked it to the side.


I reached down and held his balls with one hand, grabbed his cock shaft
with the other, and went to wor stuffing it into my mouth. It had to be
8, maybe 9 inches long, and thick, at least 2 inches across. I took the
whole head into my mouth, and could only accommodate a few inches more.
The tip hit the back of my throat, but getting it into that opening would
take a lot more practice than I'd had. I took it out of my mouth and
honored it with kisses, then licked all the way around before sucking it
back in. I fucked it with my mouth, taking all I could, and matched my
mouth with strokes of my hands. His balls were equally big, and all of
him was shaved bare. I could smell a little bit of lotion on it.
Everything I felt was wonderful.


I felt a pair of hands on my shoulders. Kim had stood and pressed herself
against Bob from behind, reaching around to encourage me. "Suck that big
cock, baby," she said, "You look so sexy dressed like that with a big
prick in your mouth.


I felt so sexy. I felt like a slut, really, but one of a community of
sluts. I could picture Kim or Charlotte or Penny doing exactly the same
thing, so I was quite comfortable.


Bob unbuttoned his shirt and tossed it aside, revealing a bra that
perfectly matched his panties. Penny, I thought, he's Penny now. Call her
that.


"Penny," I said, "I love this cock. I want to suck it for a while, but
if there are other things you have in mind, I'm easy." I felt easy. I
felt like one of those cum dumps I'd seen in porn films. My asshole
twitched, asking for cock and wondering if this one would fit.


Behind Penny, Kim unzipped her skirt and let it fall to the floor,
kicking it over to the pile Penny had started. She dropped her panties
and kicked them over as well. She stuck her cock between Penny's thighs,
and I began to stroke it in time with my mouth on Penny's gigantic prick.
I was too busy to remove my own, but the soft fabric rubbing against it
felt wonderful. I'd have to buy this set now, because I could feel an
increasingly wet spot of precum on the front of them.


My cock work was having the desired effect. Both Penny and Kim moaned
softly as I stroked them. I used saliva to wet my hand for sliding up and
down on Penny. Kim's cock gave me a few drops of precum that I rubbed
around the head. Kim's hands went to my head, holding the sides and
forcing me to take every inch I could fit. She increased my speed,
fucking Penny's big rod with my mouth.


Then Kim came around next to me. With one hand she held Penny's ass. The
other went over mine on Penny's cock, and we masturbated her together.


"What do you think, Sandy?" she whispered to me. "Do you want to try
it? It's okay if you don't feel ready."


I did have to think for a minute. Penny was bigger than anything that had
been inside me before. I'd look like one of those gape videos I'd seen
online.


"It really is okay, honey," Penny added. "I don't want to hurt you."


I came to a decision. "Let Kim go first and open me up, and we'll see
what I can do then," I told them.


I disengaged from Penny's cock and stood up. Kim came into my arms and we
kissed for a bit while Penny bent her knees and rubbed her cock between
my thighs. Then I felt Penny move away. Kim eased me over to the chair,
where I knelt on the seat cushion, my elbows on the back. She moved in
front of me and I took her cock in my mouth. It tasted wonderful, and I'd
had enough of it that it was familiar and comforting.


Penny came up behind me, and I felt her hand between my cheeks, spreading
lube over my hole, then pressing it inside. Penny's hands were larger
too, and two of her fingers slipping into my boy pussy were almost as
large as Kim's cock. Penny fingered me for a few minutes, then my two
fuckers switched places. Kim slipped easily past my stretched sphincter,
and in one long slow movement penetrated me completely, until I felt her
hips against my ass. Penny's large cock went back inside my mouth. Bent
over I could take a little bit more into my mouth, but I still needed my
hand to encompass the whole length.


Kim moaned softly behind me. "Sandy, you have the best pussy ever," she
whispered, her voice husky as she fucked in and out. Penny's hands
caressed my shoulders and head, and she began pumping her cock in and out
of my mouth.


Here I was, once again being a girly gurl, being a slut, with cocks in
both of my holes, this time bent over a chair in the back room of a
store. There was just a moment when I wondered how I got here, but the
pleasant feeling in my ass as Kim gently fucked me, and the challenge of
the much bigger cock in my mouth, pushed any wonder, any worry, out of my
mind. There were cocks in me, and I was enjoying them. Very shortly there
would be cum inside me somewhere, and that would feel good too. For the
moment that was all I needed to know.


Behind me Kim varied her strokes, sometimes long and slow, sometimes hard
and fast. Her balls slapped against my own, and the sound of flesh on
flesh supplanted the voices of three people quietly moaning in the quiet
room.


"Doll, you are a great cocksucker," Penny said. "If I don't get the
chance to fuck you today, I'd be quite happy to cum in your mouth."


"She cums a lot," Kim added. "Be ready if that happens." They both
laughed, and I redoubled my efforts to produce cum from both of them. I'd
slid over an edge here, and was listening only to the feelings of
pleasure my body was producing. My cock was rock hard, but it was
difficult to stroke it balanced as I was on my knees, with my thighs so
close together. But I could feel it -- every time Kim's strokes made my
rod move, I felt myself creeping towards orgasm.


The two cocks were dancing to their own tunes in my holes, out of rhythm,
and my body was jolted back and forth as Kim's hips pushed me forward and
Penny's cock trying to wedge itself into my throat pushed me backwards.
Kim took hold of my hips, pulling me against her as she pushed forwards.
I became that cum dump, willing these two to fill me up. My own moans,
wordless because of the giant ram in my mouth, almost drowned out the
moans of pleasure from either end of me. I was ready. I wanted that giant
cock. I'd try it.


I pushed Penny away, out of my mouth. I couldn't quite find the words to
express my feelings at that moment, and I was quite out of breath. I just
looked up at Penny's face and said, "Switch." I drew my hips forward,
releasing Kim's cock from my ass. She trotted off to clean herself in the
ladies room, while Penny moved behind me. Opening the lube again, she
poured it into my ass crease, catching it with her hand. She spread lube
around the opening, then once again penetrated my hole with two thick
fingers. I moaned with the feel of it. "I don't know if I can handle it,
Penny, but I want to try," I said, looking back over my shoulder at her.


Penny added a third finger to my ass, gently stretching me further. It
hurt a little, but my moans were as much about pleasure as pain. Penny
reached down and stroked my cock and balls, playing with them gently, as
she pressed deeper inside me. About that time Kim came back into the
room. Dropping some towels on the chair, she knelt in front of me and
kissed me. "You're sure, baby?" she asked. I nodded, my face drawn taut
in pleasure and pain, and she kissed me.


I felt Penny's fingers withdraw, and the huge knob that had filled my
mouth completely pressed against my asshole. It was very slick, as Penny
had been generous with the lube. She took hold of my hips, and as Kim
continued to kiss me, Penny jolted forward, driving the helmet of her
cock inside me, past the muscle rings and into my rectum. I couldn't
describe the noise I made, kind of a mixed scream and moan (scroan?). I'm
sure the only thing that kept the employees out front from calling 911
was Kim's mouth pressed hard against mine.


Everything stood still for a moment, as Penny graciously waited for my
hole to get used to having a truck driven through it. Kim kissed me some
more, and I decided to continue. I pushed my hips back towards Penny.
Understanding the signal she let me take charge. I got a little more
inside me, then pulled forward and gently pushed back again. After a few
more tries, I had about a telephone pole worth of cock inside me. I put
one of my hands under Kim's arm and pulled her to her feet. Grabbing her
still-stiff rod I pulled it to my mouth and began sucking.


I turned my ass over to Penny's mercies, keeping a hand on her hip as a
safety. I started bobbing back and forth between the two cocks, slowly,
gently. Penny began fucking me. Kim began fucking my mouth. My ass felt
incredibly full.


Was it a guy thing, that I wouldn't admit defeat? Was I a woman who
wanted badly to completely please her lover? I couldn't say -- but I
wanted all of that motherfucking cock inside my ass. The going was slow
for a long while. Finally, after 10 minutes or so, Penny's hips touched
my ass. I started pushing back harder. I had taken it all, now I wanted
Penny's cock to fill me to overflowing. If she came that much, I wanted a
puddle of it on the floor under my boy-pussy. At the other end I started
fucking Kim's cock with my mouth. I pulled her hard against me, until she
was sliding inside my throat and my nose was pressed into her belly with
each stroke.


"Baby, you are so tight back here, you're strangling my cock. I'm gonna
cum soon, and fill your ass full of Penny's jizm," Penny rasped.


Kim moaned gently as I fucked her cock. I had never felt so full, and in
a strange way, fulfilled. The biggest cock I'd ever seen was inside me,
and I was pleasing a woman I'd become quite attached to with my mouth.


Kim said, "Tell me when you're ready, Penny. I want us both to fill this
girl with cum. I want it streaming out of her at both ends.


I let them take over, take me, use my body for their pleasure. I held
onto the chair while I was rapidly fucked in both ends. Penny had
stretched me beyond any normal measure. Kim was in my throat with each
stroke.


"Soon, baby," Penny moaned.


"I'm gonna cum in her throat," Kim replied


Penny gave up any pretense of gentleness, and pounded me with her massive
prick. Kim took hold of my head and fucked my mouth. I was aware of
nothing other than those two penetrating poles. I wanted their cum. I
squeezed my lips around Kim's cock, squeezed the muscles in my ass around
Penny's mighty penetrator, and held on for dear life. The chair was even
moving as they fucked back and forth into my holes.


"Now, Kim, NOW!" yelled Penny, her voice rising.


Kim took one more hard stroke, then pulled my head against her belly, her
cock buried in my throat. I felt it jump and twitch as she came directly
into my stomach. Behind me it felt like a fire hose had gone off in my
rectum, as spurt after spurt of hot cum was forced up inside me by
Penny's rapid strokes. With both pressed so hard into me, my spine was
being compressed. Kim finally relented so I could breathe. She squatted
in front of me and kissed me, then put my head on her shoulder and hugged
me tight against her. "Baby, you're crazy," she whispered in my ear.
Then she kissed me again.


Penny slowly eased out of my ass, and I could feel a breeze blow through
the gape she'd left there. Her cum dribbled out of me in a steady stream.
Kim helped me to my feet, then laid a towel over the chair and I sprawled
out over it. Penny's cum poured out of me, soaking the towel.


Kim leaned over me and kissed me. "After all that, I can't let you leave
here with a case of blue balls," she said.


With that she got on her knees in front of me and moved my legs apart.
Even with all the distraction of having an artillery piece shoved up my
ass, my cock was still halfway hard. She took it in her hand and took the
entire thing in her mouth. It didn't take long for me to get back up to
full stiffness, and she sucked like she'd never see cock again. Penny
came back in and gathered up her clothes. As she bemusedly watched, she
put her big girl panties back on and began the transformation back into
Bob.


I smiled back at Penny turning back into Bob, then closed my eyes to
concentrate on what Kim was doing to me. I had just gotten my breath back
before she started, and now my heart pounded and my breath rasped in my
sore throat as she sucked me to orgasm. I felt my ravaged asshole trying
to squeeze shut as she had her way with my prick. Finally, I was there,
there, THERE, and my load exploded into her mouth. My whole body twitched
as I pumped cum into her. She kept sucking until she had every bit and my
cock was completely clean.


The two of them pulled me to my feet and walked me to the bathroom. Bob
went back and collected my clothes, hanging them on the back of the door
as I sat on the toilet dripping out the last of his load.


"Come up front when you're dressed," Kim said, and kissed me. Then they
left me to my own devices. It took a few minutes and a lot of soap and
towels, but I managed to make myself respectable enough to be seen in
public. I threw the towels in a laundry bin there, dressed in my boy
clothes, and went back to the fitting room. Everything I'd laid out was
gone, so I went back out into the store and met Bob and Kim at the front.
Kim put her arm around me, bumping her hip against mine and smiling at
me.


Bob smiled and handed me a gift bag. "We'll settle up another time," he
said. "You've got me too worn out to work the cash register. That
doesn't happen very often."


I thanked him profusely and told him not to forget to charge me. It was
important to me to pay my own way. "Today was an experience I won't soon
forget. In fact, I think I'll be feeling it for quite a while."


They laughed, and Kim and I left arm in arm to go looking for some
dinner.


AUTHOR'S NOTE:


Sandy's had some very serious experiences. His world has been broken wide
open, and he's slid into an alternate universe.  We're not close to any
conclusion, so I'll keep working on more chapters. If you like my
stories, drop me a note. Even if you don't like them, HIT THE DONATION
BUTTON. This only works with my writing and your donating.