Sarah Carerra Chapter 27 There s Something about Seeing Mary
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Something About Mary
"Hey, Dillan! Mr. bleach blond!"
It wasn't completely out of the blue, but I was certainly caught off
guard when Mary called out to me. Though I was hardly one of the school
punching bags, I wasn't exactly a popular kid either. I had my small
circle of friends that I was happy with and we largely avoided the drama
riddled 'upper echelon' of the school hierarchy. So I never expected one
of the most popular girls in school to spontaneously initiate
conversation with me on her own.
"Uh. What's up, Mary?" I gulped suddenly over-conscious of my short,
platinum blond hair. She was close enough to smell the strawberry
fragrance of her shampoo. I had to take a step back so as not to be
overwhelmed. "Something the matter?"
Though she had started out her usual cheerful self when she approached,
her expression fell suddenly and she shifted her feet. Her normally
bright hazel eyes danced around refusing to meet mine. "I... well. I
need some help with something. Normally I'd ask Jack, but we had a bit
of a fight recently and I'm avoiding him. Since you and I share some
classes this year, and you seem like a nice guy. I figured if I asked
you to help, it might be a good opportunity to get to know you a little
better, too." She looked up at me through her light brown bangs. Her
girl-next-door game was so strong, I almost thought I could hear her
playing a tune on my heart strings. It wasn't as if I weren't interested
in her, too, so I figured I'd bite. I worried that I might regret not
doing so.
"What do you need help with?" I inquired. I almost choked on the last
word as a furious blush filled her cheeks and she began twirling a lock
of hair. There was no way this was going there.
"I can't say. Not here. But if you're willing, could we go to your
place after school today?"
Nope. No way. No way in hell. "Yeah, sure. I don't have any plans
this afternoon. My parents don't get home till later in the evening." I
have no idea why I included that last part. I originally had been
planning on hitting up the local arcade with my best friend, Ben, but he
canceled on me this morning saying something about drama club. So, yeah,
I really was free. Mary giggled softly behind a hand.
"Great, thanks! I'll meet you at the bottom of the stairs to the parking
lot after the last bell, kay? I'm looking forward to it. Seeya!" And
with that, she practically skipped away. She didn't let her short
stature get in the way of having a fit physic. She wasn't on any school
teams, but I had heard she played tennis recreationally. Her outfit
today looked like it would be at home on a tennis court, with its knee
length pastel green skirt topped with an equally pastel pink collared
polo.
Somewhat dazed by the encounter and the sudden promise of further
interaction, I almost didn't make it to my next class on time. And I
certainly struggled to focus the rest of the day.
---
My overactive imagination envisioned plenty of possible scenarios for
what Mary might want my company for over the course of the day. Almost
all of them seemed too good to be true. As Mary glanced curiously around
my room, I hoped desperately that she couldn't hear my heart thumping
because I could have sworn it was drowning out almost everything else to
my own ears. My guest helped herself to a seat on my bed. I flopped
into my desk chair and spun to face her grateful not to have to support
myself with my own legs for a time.
"Okay," she started taking a breath. "Jack told me I don't understand
boys' feelings. So I was hoping you might be able to help me learn about
boys a bit more." Mary stood up suddenly and moved closer. "Es...
especially here. He said I need to work on my... technique." Her face
was flushed. At least as much as I it felt mine was. Of all the
potential scenes I had imagined, this had to have been the least likely,
and yet here we were. I couldn't will myself to stop her as her hand
made contact with the tent in my pants. Our eyes met. "May I?" she
asked timidly. I swallowed and then nodded.
Mary undid my belt, and unzipped my fly. I had to restrain myself to
avoid blowing it from her merely closing her fingers around my shaft
through the fabric of my boxers. She found the opening in the boxers and
threaded my cock through it, exposing me to the open air.
"My. You're pretty big, too," I heard her murmur. She caressed me
gently, with one finger at first, and then adding another until she
enveloped me with her whole hand. Her lips followed soon after. I was
already at my limit though, and the feeling of warmth inside Mary's mouth
was too much. She may have bobbed over my crotch three times at most
before I spilled. Having to baby sit my cousins the last few days had
deprived me of good opportunities to masturbate, so I was plenty pent up.
I let out a shaky breath as Mary's lips coaxed from me, every drop I had
saved up. My orgasm could not have lasted more than ten seconds, but it
felt like ten minutes. All the while, Mary sat there on her knees
steadily swallowing it down without hesitation. When I finally finished,
I felt her tongue clean me up, and when her lips freed my member from
their succulent grasp, I was as hard as when she started.
Mary sat back looking thoughtful, as if she had not just sucked me off.
"Hm... that seemed simple enough. What do you think?" She looked askance
at me. "Anything I might have been able to do better?"
While I wasn't a virgin, I couldn't really claim to be experienced
either. I did it a few times with my ex but she never did a blow job so
this was a new experience for me. When I finally reclaimed enough oral
dexterity, I explained as much. Mary seemed to understand.
"Hm.." she pondered with a nod. "Well, I'm not out of options just yet
and that works with the other thing I wanted to try. Would you mind
stripping for me?" She requested casually, beginning to pull her polo
over her head. I watched dumbfounded. Her rack bounced a bit, muffled
by her bra as her head reemerged from under the fabric of her now
discarded shirt. She looked at me expectantly until I realized I was
still sitting there staring like an idiot. I hastily shrugged out of the
rest of my pants and boxers, and my shirt joined Mary's skirt and panties
on the floor.
I took the opportunity to admire her nude form as she fetched something
from her school bag. She had the model figure, wide hips making smooth
curves. A generous and perky, but not oversized bust. Her silky,
shoulder blade length brunette hair hung loosely with an ever so slight
hint of a perm. She had a small patch of neatly trimmed pubic hair
crowning her crotch, reminding me of how I had neglected my own
manscaping after breaking up with my ex. My viewing pleasure was
abruptly interrupted by the two items Mary pulled from her bag.
"Wh..what are those?" I resisted the urge to gag. They looked like
human skins. In her left hand she held one with long light brown hair
much like her own. The right was larger and was topped with short black
hair. I had to stare at them for a second before I recognized their
surreally deflated genitalia.
"I found a very interesting site online a few weeks back that custom made
these. They're like... super realistic disguise suits. I had one made
of me, and one of Jack." I recognized Jack's crew cut now that it was
mentioned. "They arrived yesterday, and due to some snafu with the
shipping I only have till this weekend to decide if I want to return them
for a refund. Thanks to my little spat with Jack though, I can't...
fully test these by myself."
They were still creepy, but I was starting to put together the picture.
"So you want me to be Jack?"
"Actually, I want you to be me."
Huh?
Would that even work? Mary barely came up to my chin, how would I fit
into a copy of her? She handed me the Mary suit. It felt uncomfortably
real, from the hair on its head to the intricately painted nails at the
end of each finger. I looked up to see Mary already putting on the other
suit. She had it almost up to her hips, but it seemed that something in
the front was delaying her from pulling it up further, though with her
back to me, I couldn't tell what. Probably something with Jack's junk.
Mary had said that I was 'pretty big, too' but I guess I'd see for myself
soon enough. Though I was alarmed to realize that that last thought had
come naturally to me, I realized that I had already begun inserting my
leg into the opening in the Mary suit myself. What was it that had
compelled me to go along with this? The fervent desire to help or please
the naked cute girl in front of me? That it's too late to turn back now
that she seemed convinced I was okay to continue? Or perhaps there was
some twisted curiosity egging me on. Whether for fear of betraying
Mary's expectations or out of inquisitiveness for the unknown, I focused
on the suit already half way up my legs.
It was cool inside, and there was just enough of a clamminess to the
interior that it clung snugly to my limbs without inhibiting my entry.
Before I knew it, I found myself staring into the pelvis of the Mary suit
around the sight of my raging boner. Upon closer inspection, I noticed a
pouch built into the inside that looked like it would fit me. Nothing
ventured, nothing gained, right? I stuffed my junk in, pulling the suit
up around my hips as I went. With the suit wrapping my body below the
waist, I was amazed by the sight of that neat love patch I was admiring
earlier now adorning my own crotch. It felt expectedly bizarre. I could
still feel my penis encased in its weird flesh pocket, but a new
sensitivity blossomed in my loins to accompany it. I suppressed the urge
to explore between my now smooth shaven legs in favor of finishing the
process of donning the strange skin suit.
Her torso followed the same pattern her lower body did. The arms were
not unlike putting on latex gloves, though whatever the suit was made of
was far more breathable than any gloves. Filling out the Mary suit's
shoulders brought with it the sensation of weight, and I had to resist
another inclination to start playing with the new girl parts I felt
attached to my chest and instead focus on putting the head on over my
own. I dove in through the seam in the suit's neck, plunging into
darkness while I tried to feel my way around inside the mask. I felt
hands that were not my own close up the opening in the back of the suit
and pull at the mask here and there until my eyes lined up properly and
light returned to my world.
My first sight through the eyes of a girl was a very close full frontal
view of Jack in all his manly glory.
"Gah!" I yelped in surprise. At first I thought my voice had cracked,
something I had just recently had celebrated not happening in a while.
When Jack opened his mouth, it slowly dawned on me just the situation I
had gotten into.
"Whoa there, Dillan. It's just me, Mary." The incongruity of the words
spoken in Jack's handsome baritone was as disorienting as the massive
erection that definitely dwarfed my own manhood poking up excitedly from
between Jack's legs. Jack backed off. "Here, take a moment and check
yourself out. Looking good if I do say so myself," he said with what
seemed to be a reasonably Mary-esque smile. He gestured to the mirror in
my adjoining bathroom.
Having seen Mary in her birthday suit not a minute earlier, I was baffled
by the impossible accuracy of the suit I now wore. I met the hazel eyes
of the girl in the mirror and watched in awe as she mimicked my every
move. My eyes wandered south. I was suddenly aware of the rhythmic
rising and falling of my chest with each breath as it moved the lovely
mounds of flesh attached to my front. I could get used to this sight.
My breath caught when I touched one such lump. I felt it. Somehow, I
could feel the tactile sense of my fingers contacting what should be my
fake boobs. If these felt real, then...
My attention raced lower. I spread my stance and let out an involuntary
cry when brushing against my new clit sent an electrifying arc through my
whole body. Jack looked in to check on me.
"These are incredible, huh?" He said with a funny grin. He took a step
closer. I could see him stroking his still plenty excited cock. "I
stuffed a dildo in the sleeve here, but I can feel it like it were real.
Makes me glad I chose one of my fancier cumming dildos." I wasn't as
enthusiastic about that as he was.
A little voice in the back of my head whispered, It's just a dildo. It's
not like I wasn't going to try pleasuring myself in the suit anyway.
Maybe this will help Mary understand guys better to be on the receiving
end. Yeah, it's Mary inside, just like I'm still me inside. This is to
help her out.
Still trying to convince myself, I followed Jack back out of the bathroom
and he sat on my bed again. His legs spread invitingly.
"I don't expect you to have amazing technique or anything since this is
your first time. I'm just curious about how it feels," he reassured me.
So it was a foregone conclusion that I'm giving him a blow job. Alright.
I'm probably already several feet down the rabbit hole already. Not sure
I'd want to know what he might do if I tried backing out now...
For just being filled with a dildo, whatever extra functions it might be
equipped with, the warm dick felt unsettlingly real and even bigger in my
dainty feminine hands than it had in his own masculine ones. Jack drew
rasping breath as I began stroking the fake(?) member. Trying to
remember how Mary had done it, I leaned in. Fortunately it did not smell
like the jock funk I was afraid it might, and on my tongue it tasted,
predictably fleshy, with a hint of salt, whether from sweat or whatever
Mary filled her ejaculating dildo with. I soon found my mouth full of
man meat and despaired at the sight of a few more inches to go. Could I
take any more? Should I? Is it okay that I'm even considering that?
Knowing my gag reflex, I decided against trying to deep throat, and
instead pulled back. I pumped over the cock, moving my upper body with
my diaphragm and as I found myself more comfortable with the feelings and
motions I started to pay more attention to what I could do with my tongue
with each pass. Just as I was really getting into it, Jack cried out.
"Aaah! Cumming!" was all the warning I got before an intense salty-sour
flavor assaulted my tongue. I wanted to get off, but Jack grabbed my
head and held me there as he continued to pump his semen into my mouth.
I refused to swallow and instead let it sputter and spray from my lips
with each contraction. Finally, after what felt like ten minutes, but
probably wasn't more than ten seconds, he finished his climax and I was
released to catch my breath. If girls had fake cum for their fancy
dildos, you'd think they would flavor it something pleasing to taste...
"Haa... ha... Wow... so that was a guy's orgasm..." Jack panted. "Sorry
about that, it just, felt too good. It's different from how a girl
feels..." He met my eyes. "I'll show you how it is for us girls, if you
want." He patted my bed. The tingling in my mouth said 'no,' but the
burning in my crotch screamed 'do me.' I climbed onto the bed.
O Holy Lord of Shit, my mind fizzled as if Jack's tongue were caressing
my brain itself through my cunt. I felt my pussy convulse as my pleasure
peaked and was vaguely aware of the now rampant moisture pouring from my
female lips, but to my surprise, the pleasure didn't fade like I
expected. The feeling of greater pressure against my crotch drew my
sight back to my partner. Jack rose, advancing from oral to preparing
for penetration. Was I ready? Yes.
No. Insertion was accompanied by a rainbow of sensations: warmth,
fullness, the buzz that I had come to recognize as female pleasure, and a
pain all bent together in my head, in my vagina, in my everything. It
was overwhelming, and it only intensified as he started to thrust. I
came. I came again. A third time. My body was on fire and it was not
calming down no matter how much liquid my cunt produced. I was exhausted
by the time I felt a new feeling blossom inside me, a further spreading
warmth that traveled from my pelvis up towards my stomach. Towards my
womb, I realized, as Jack came inside me. The final feelings of him
pulling out ultimately left me a quivering pile of limbs upon my bed.
The sound of Jack's movements compelled me to try to rouse, but the grip
of physical and emotional fatigue clung too strongly, and my world soon
faded to black.
---
"Dude, I know these suits did a lot of the heavy lifting, but you're a
fantastic fuck," Jack chuckled softly over his sleeping friend. In the
adjoining bathroom, Jack stood over the toilet and let his urine clear
out any semen remaining in his shaft. He checked on the sleeping Dillan
before stripping out of the Jack suit. Mary extracted herself from
Jack's back, enjoying the feeling of her breasts free to bounce around
again. As she hauled the suit to her waist, she took extra care to
remove her cock from the sheath of Jack's before continuing to slip out
of his hairy legs.
Free from the male disguise, she drew a delicate hand along her smooth
leg, reveling in the feeling of her feminine body. As her hands drifted
up from foot to calf to thigh, the eventually reached her hips where the
paused, taking a moment to close around the thick penis protruding from
the lips of her pussy. Like before, the throbbing member looked small in
her girly hands, but she loved it that way. She did not think she could
masturbate normally ever again. The thought renewed life in the male
appendage.
With renewed fervor, Mary's fingers danced along her shaft. She watched
Dillan's sleeping form while she pumped the incongruous member. One hand
moved to heft and grope one of her breasts. She moaned softly, getting
closer until finally her whole body tensed and the phallus pulsed,
shooting a stream of jizz over the sleeping Dillan. Even having been
saving for several days, Mary knew having a real partner would make her
sexual adventures even more exciting, and her cock's stamina and volume
today showed that it agreed. Finally flaccid, Mary carefully pushed her
manhood into its hiding spot within her womanhood. She borrowed the
bathroom again to freshen up a bit before finally redressing and packing
the Jack suit up. She penned her friend a quick note to explain the
situation before excusing herself. Her friend might be upset for a bit
after reading her note, but she knew he would get over it.
Pleased with his performance, Ben wondered what other sexual adventures
he could have with these suits. He couldn't claim to understand how the
suits worked, but he was more than happy to use them to their fullest.
The website, 'Max-imum Realism: Custom Disguises by Max,' he had ordered
them from had plenty of instructions but revealed no secrets. He was
looking forward to bringing Dillan in on it after he wakes up. But there
was time to kill until then. Aside from the blow job, Ben had pitched
all afternoon. Maybe it was time to try catching, especially after
seeing Dillan's reaction to female pleasure.
He fished a Hello Kitty themed smart phone from the purse under his
shoulder as he locked up Dillan's house with their spare key and looked
out at the street.
"Heya, Jack, baby. My family got home a bit early from our beach house.
It was nice, but it would have been nicer with you. I missed you soooo
much! Are you busy now? I wanna come over and maybe... you know..."
Myra
- 08.07.2022
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