Steamy Stories

Her Inverted Intimacy Challenge: Part 4


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Anna almost loses Jake, then beds him.

By darrenr - Listen to the

► Podcast at Steamy Stories.

Wordlessly they lay there, Anna clutching his hand as he

held her. Eventually her breathing returned to normal, and her grip softened.
Jake realized he had his dick pressed against her bottom in their hug, but it
had softened during the past few minutes. He felt proud of himself and his soft
dick. Anna was the epitome of his sexual desires, but in this moment even his
perpetually rude cock recognized this was not the time to make selfish demands.
It felt nice snuggled up against her soft bottom.

His face resting on Anna’s back, he couldn’t

help smiling. He had done it! He had most definitely given her something
she’d never felt before.

A small movement from Anna brought him out of his reverie,

and he realized she was crying. In a single second his heart fell from
impossible heights of blissful pride and satisfaction down into despair.

“Anna, are you okay?” Jake asked, his voice

small. “Did I hurt you?” For what felt like an eternity, there was
no response at all. Then Anna’s grip on his hand tightened, and she
pulled it against her chest.

“Thank you,” she said, her voice cracking.

Holding his hand tight, she moved to sit up and he pulled back to give her
space. She looked at him with cheeks wet with tears. “I have no idea why
I’m crying. No, you didn’t hurt me. You made me feel more pleasure
than I ever thought possible. I don’t know where all this emotion is
coming from.” She leaned her head against his shoulder, and he put his
free arm around her again. They sat in silence for a few minutes more. Jake’s
heart gradually recovered from its moment of terror, and he breathed easy
again, the sweet scent of her hair in his nose.

With a deep breath Anna lifted her head and looked at Jake.

Still feeling elated from his success, he started to grin. This in turn made
Anna smile.

Making a goofy face, he said, “Well?”

They both burst out laughing. Jake felt elated at what he

had accomplished, giddy with delight at what they had shared, at how close he
felt to Anna.

When the laughter died down, Anna’s face grew thoughtful.

“What I just experienced, was that normal? Is that what everyone feels
when they orgasm? Is that what you feel?”

“I doubt I’ve ever experienced anything even a

tenth as good as that,” Jake said. “That seemed to be in the
earth-shattering category.

“It really was. My legs feel weak. I can’t get

over how good that felt. I honestly didn’t know anything like that was
possible. How did you know how to do that?”

He thought about all the ‘how to’ videos about

sex he had watched, all the guides to please a woman he had read, how he poured
all his love and focus into doing the best he could for her. “I think I
just got lucky.”

Anna laughed. “No, I’m the one who got

lucky.” She sat in silence for another moment looking at her toes.

“Jake?”

“Yes?”

“You kissed my pussy.” It still caught him off

guard when she used that word, but he liked it.

“Yes. I hope you don’t mind. I knew you needed

more and that was my only idea,” Jake said.

“Was it, was it gross?” Anna asked.

“Quite the opposite,” Jake said. Of course, the

truth was he was overflowing with affection for her. Confessing all that now
seemed too much. He kept silent.

“Anna,” Jake said quietly, “Did I hurt

you?”

“What on earth are you talking about?” she said.

“You know, when I, when I put my finger inside.”

“Oh!” she giggled. “No, it didn’t

hurt at all. Quite the opposite. Completely different from the doctor.”

“Oh good,” Jake said, his finger remembering.

Warm, snug, delicate. He felt his arousal start to grow and tried to think
about something else instead.

After a few minutes, Anna asked, “How tired are

you?”

“Oh, I’m fine.”

“But it took me ages to reach the climax. You must

have been getting a little tired?”

“A little,” Jake admitted. “But I’m

fine now.”

“All recovered?”

“Yes, all recovered!” Jake said, laughing at the

interrogation.

“Good!” Anna said, distractedly stroking the top

of her thigh. “Good, I’m glad. That was an incredible thing you did
for me, just an incredible thing.”

“Anna, please,” Jake protested, turning his head

to meet her eyes. “I enjoyed it too, you know.”

Anna smiled but quickly looked away in embarrassment.

“Of course, now, now it’s your turn.” Anna was clearly
getting nervous. “I owe you some–”

“No,” Jake said a little too firmly, sitting up.

“No, listen. There’s nothing owed. Nothing transactional here. If
some day in the future you find yourself needing to touch me, truly deeply
needing it, then nothing would be more welcome. Nothing. But I’ve been
slapping this salami and having orgasms for years. I’m fine. What’s
important now is you’ve taken a huge risk with this first step, and it
was a good experience. I think you should load up on good experiences before
taking more risks.”

“'Good experience’ rather understates

things,” Anna said with a laugh.

“Here’s what I think,” Jake said. “No

offense, but you look a bit worn out. How about I get us a snack and we watch a
movie to relax?”

Anna smiled. “I do feel a bit drained. That would be

nice.”

Jake returned with some apple slices, cheese, and crackers.

Anna cued up a movie and he realized he was feeling pretty drained himself.

Sometime later he awoke to find Anna still sitting with him.

The movie was over. It took him a moment to notice she was looking down at his
crotch.

Jake must have moved a little because Anna startled, looked

away, and began to get up.

“What’s the matter?” he asked.

“Sorry, I shouldn’t have been staring while you

were asleep.”

Jake laughed. “Are you joking? We’ve been naked

with each other for weeks now. Why would I mind if you looked at my ugly
wiener?”

“I don’t know,” Anna said, settling back

down on the couch beside him and leaning against him. “It just felt like
peeping or something.” She smiled. “I guess I was being
silly.” Jake nodded and put his arm around her again, feeling her shoulders
rise and fall as she breathed, enjoying how her breasts moved.

“I don’t think it’s ugly,” Anna said

after a few minutes.

“Huh?”

“Your penis. Your cock,” she added with a smile.

“I don’t think it’s ugly. It got super small while you slept.
I thought it was cute.”

Jake felt the topic of discussion begin to swell. He

whispered, “Uh oh, it knows you’re talking about it.”

Anna bent down close to his dick and whispered to it,

“I think you’re cute when you’re all shrunk up small!”
Then she sat back up, giggling.

His dick jumped a little in response, and Anna laughed more.

“Can I tell you something stupid?” Anna asked.

“Of course.”

“This is embarrassing, but, when your cock gets really

big…” Anna looked down. In a quiet voice, she said, “I feel a
little bit scared of it.”

Jake immediately began to shrink. He frightened her? He

moved to cover himself with his hands.

“No wait,” Anna said, grabbing his arm and

pulling him back down. “That’s not what I meant. You didn’t
do anything wrong.” She pulled his hands up so his crotch was exposed
again. “All I meant was it’s intimidating when it gets big.”

Jake thought for a moment. “I have to be honest.

It’s hard to not be aroused when I’m with you. But I will
try!”

“No,” Anna said. “No, I don’t want

that. This doesn’t make sense, but I also like when it gets big. I feel
both excited and a little afraid.” She looked down and then back into his
eyes. “I guess what I mean is I appreciate how patient you’re being
with me. I intend to return the generosity you’ve shown me, but, but
I’m just not ready yet.”

Jake let out the breath he didn’t realize he was

holding. “Oh, well that’s no problem. I thought we already settled
this? You don't 'owe' me anything."

"I know," Anna said, "I just--"

"Listen," Jake interrupted. "Believe me. I'm

having a... profoundly good time. All I can think about is hoping you'll invite
me back for another round."

"What does your schedule look like tomorrow

evening?" she asked.

Jake chuckled, and he felt his dick jump at the thought.

"I think I can fit you in," he said.

Anna smiled, and leaned her head against his shoulder again.

Unexpressed Desires.

Anna didn't like to directly ask for Jake to work his magic

on her. Her face would occasionally get this hungry look that was extremely
obvious, and Jake made sure to offer. As he practiced on her more and more, he
became immensely proud of his growing expertise. He had learned to read her
feelings, her body's reactions, and her needs. Sometimes it was clear she
needed immediate relief, and he would give it to her. Other times, his favorite
times, she enjoyed dragging it out. He would bring her right to the edge, and
then back away, teasing her over and over until she couldn't stand it even one
more second. When she reached that point, he would take her over the edge into
an incredibly powerful orgasm that left both of them exhausted afterwards.

She wasn't ready to return the attention. Occasionally she

would offer, though it clearly came from a sense of obligation. Jake wanted her
to touch him out of desire, not guilt. At least he wasn't embarrassed about
being erect around her anymore. Sometimes he got that "blue balls"
ache, but not often. After she left every evening, he didn't even feel the need
to masturbate anymore. He just missed her and tried to get to sleep quickly so
the morning would bring her back.

Jake hated hiding his true feelings from her, but he feared

ruining what they had. Maybe someday he would have to confront that. He wasn't
ready.

The Saturday of changes.

It had been a tiring Saturday, but fun. Hiking in the nearby

foothills, taking countless photos, and talking about all kinds of things. She
seemed so fond of him as they explored and laughed together, he could almost
believe she loved him as much as he loved her. He hoped so, at least. Lost in
his thoughts, he realized Anna was talking to him as she drove them home.

"It's funny," Anna said. "I was talking with

my mom the other day and she was acting all confused about us. Apparently, I
talk about you all the time and she thinks we're actually dating. 'Mom!' I
said, 'Jake doesn't think of me that way. We're just good friends.' I don't
know why she won't let this go."

Jake felt his ears burning. He doesn't feel about Her

that way? Feeling exhausted from the hike, he was unable to slow the emotion
building in his heart.

"That's bullshit," he said, more anger in his

voice than he intended. He stared out the front window.

Anna glanced at him with surprise. Jake didn't turn toward

her. He knew Anna wasn't a malicious person, and he knew he was probably
messing up everything, but it hurt.

"What do you mean?" Anna asked quietly.

Jake knew his anger was out of control, but he spoke anyway.

"You always assume too much. Mostly I don't mind, but you don't get to
make assumptions about my feelings, to lie to my face. It couldn't be more
obvious how I feel about you, how I've felt about you from the very start. I
don't expect you to love me back. You don't owe me anything. But it would be
really fucking decent of you to at least be honest that You set the rules. You
don't get to put words in my mouth."

Anna didn't respond. Jake stared straight ahead. He heard

some sniffling and saw her wiping her eyes. He wanted to comfort her. He hated
to see her in pain, no matter the reason. But his angry heart felt better, even
if he dreaded to think what he had done to their friendship.

The rest of the drive home was silent. They went to their

separate apartments that evening. Jake showered by himself for the first time
in weeks feeling lonely and sad. Fearing he had made the biggest mistake of his
life, he made it as far as the couch before breaking down in tears and crying
himself to sleep beneath the throw blanket.

Sometime later, Jake heard Anna's voice. Was it a dream? His

head felt heavy with sleep. In the darkness, Anna was pulling his hand.

"Come on, sleepy-head, you'll be more comfortable in

bed," she said.

Her voice held no anger, only kindness. It must be a

dream. He found himself in his bed. Anna climbed in beside him, her warm
back snuggled up against him as she pulled his arm around her. He longed for it
to be real, though he knew it couldn't be. Anna hated him now. It was over.
Jake's mind drifted into blank despair again.

Anna was smiling at him. Her face was the most beautiful

thing in the world and her gaze felt like being bathed in warm sunshine. She
leaned in to kiss him. In the dream logic, this wasn't a surprise. She loved
him as he loved her, and kissing him was the most natural thing in the world.
Her lips touched his and he felt his heart grow and expand until it consumed
the universe with their love and joy. All they needed was each other, forever.
Touching her face, he was the happiest man in the world. He called out her
name.

"Jake," he heard Anna's voice, gentle and tender.

"Jake, are you okay?" He felt a warm hand on his cheek.

He opened his eyes and saw the light of dawn, soft on Anna's

face. What was she doing here? Genuine concern was in her eyes.

"Jake, you were having a dream. Are you okay?"

As he woke up more, he realized his dick felt strange.

Moving his hand, he found it was on Anna's hip, and her hip was wet. The sheets
were wet. His crotch was wet. With horror he realized it had been a wet dream.
The biggest, messiest wet dream of his life. And it was all over Anna.

His body involuntarily jerked in panic. Tears erupted from

his eyes and he started gasping, unable to speak even if he knew what to say. What
was she even doing here? He couldn't see clearly through the tears, but he
had no trouble imagining the hateful look she must be giving him.

"Sorry!" he blurted. "Oh god, I'm so

sorry." He started to pull back, to climb out of the bed and away from the
mess, away from everything. But she gently pulled him back down beside her.

"Shhhh, don't talk," she said. "Just look

into my eyes and breathe."

Jake squeezed his eyes shut, too ashamed to look at her.

"Everything's okay, Jake," Anna continued.

"I'm here with you, and everything is okay."

Jake opened his mouth to apologize again but she put a

finger over his lips before he could speak.

"There's nothing to say. Just breathe with me."

He opened his eyes and through the tears saw Anna's kind

eyes looking into his. He inhaled, and his chest jerked with a suppressed sob.

"Everything's okay, Jake. Just breathe with me."

Jake took another breath, and he managed to make it a bit

smoother. Anna smiled and stroked his temple. He focused on the warmth of her
hand on his face and tried to forget the shameful wet mess between them on the
sheets.

Eventually his breathing calmed down. Anna used her thumb to

wipe the tears off his cheeks, and she smiled at him.

"Now we're going to do something silly," Anna

said, "And you're not going to argue with me. You're going to come with me
to the shower, but first you're going to close your eyes. Do you trust
me?"

Jake was puzzled but he nodded and closed his eyes. He felt

her pull the cold sticky sheet off them, and then she helped him stand up.
Holding him from the side, she slowly guided him, and he realized she was doing
this so he wouldn't look at the mess on the bed. He felt the shame lurch back
into his heart, but at that very instant she put her hand on his chest, right
over his heart, and he calmed back down.

He kept his eyes closed as his feet touched the cold tile of

the bathroom. He heard Anna start the shower, and then she pulled them together
into the hot water. She pressed the front of her body against the front of his
and squeezed him close, her head on his shoulder with her face against his
neck. Her breasts were soft and comforting. Her hips pushed against his and he
felt his shrunken, ashamed dick press against her thighs. He put his arms
around her and returned the hug. The hot water poured over them both and he
felt his body relaxing.

For a few minutes they just held each other. Anna adjusted

the water slightly hotter. The air filled with steam and their bodies seemed to
blend as the water coursed over their shoulders. Anna sighed happily against
his neck. She didn't hate him for ejaculating on her in his sleep. She wasn't
repelled. She didn't find him revolting. Anna squeezed him tighter, then pulled
back from her hug.

"You can open your eyes now." She was smiling at

him. She put her finger to his lips and then grabbed the shampoo bottle. Her
fingers massaged the shampoo into his scalp and his eyes rolled back in
pleasure. She rubbed far longer than was needed to wash his hair, clearly
enjoying his reaction. With a soapy wash cloth, she rubbed his shoulders. Her
thumbs worked into his muscles as she washed down his back, down each arm,
across his chest and down his belly.

Without hesitation she gently held his shrunken dick and

stroked it carefully with the wash cloth. It wasn't sexual as she cleaned him,
it was simply loving. She washed his bottom, his legs, and his feet, including
scrubbing between each toe.

She pushed him back into the hot water to rinse and held a

finger up to tell him to stay there. Then she carefully shampooed her own hair,
and washed her own body, making sure he was watching. Finally, she joined him
in the hot stream of water and hugged him as she rinsed.

When Anna turned the water off she grabbed a fresh towel and

dried him carefully over his whole body before drying herself while he watched.
He laughed when she used the hair dryer on him, blowing warm air all over their
bodies until they were fully dry before she got a brush and started drying his
hair too. She had fun styling his hair to look ridiculous, and then quickly
dried her own hair too.

Anna wrapped them each in bath robes to stay warm, and

walked him to the kitchen. She put him in a chair and he watched while she made
coffee, toast, and eggs. She sat beside him while they ate in silence, watching
each other and giggling now and then.

When they finished eating, she held up her finger again to

tell him to stay in his chair, and then went off to the bedroom. Anna was gone
only a few minutes before returning and leading him by the hand back to the
bed, which now had fresh sheets. She sat beside him on the bed and smiled at
him.

"How are you feeling now?" Anna asked.

"Better?"

Jake smiled. He was clean, warm, and fed. Also, he realized,

he was loved

...more
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