Giant Steps Ch. 03

Jane found it difficult to focus on her parents.

Sam knew just how to treat her penis. She liked having someone serve her, and couldn't help but be a little turned on by the taboo nature of their actions.

Sam ventured further into his quest to pleasure Jane. He'd put her panties resting just under her balls, making them lay out in the open over her underwear. As he stroked with one hand, he brought his head to her balls and began probing at them with his soft lips. He found that they were a little sweaty, but he didn't mind licking at them, even if it felt a little degrading. Maybe a part of him wanted to be degraded.

He ambitiously brought more of his tongue to her scrotum, lapping up and feeling around the shape of her balls with his tongue, all while maintaining a steady rhythm on her cock.

He now encompassed the whole of one ball in his mouth, feeling around the length of it with his tongue and sending waves and waves of pleasure which Jane desperately struggled to hide.

He brought his attention to her other testicle and repeated the same exercise, driving Jane crazy. Her previously quick tone took on an edge of desperation and perhaps even drama. Where she was speedy with her words she was now restrained, trying not to reveal anything through the noises that might escape her mouth.

Her parents seemed to have no shortage of things to discuss. Still, Sam took it as a personal mission to make her cum before her call was up.

He retracted his mouth from her balls and continued stroking, realizing that while he was focused on her balls he'd started to stroke faster, and with a less steady rhythm.

He returned to his prior rhythm, maintaining motion at a steady pace, now consciously increasing the speed of his strokes.

His own cock was struggling against his underwear, but he decided to keep a leash on it. Right now was about Jane, he thought.

As he stroked up and down, up and down, he noticed the first drivel of pre-cum emerge from the tip of her penis. He desperately wanted to taste it.

He brought his mouth to the tip of her cock. She slowed down the stroking to let his venturous tongue gently lap up her pre-cum. At this, Jane came the closest she had in the whole call to letting out an audible moan. To avoid the obvious tell of her face, she took her head to the side and pretended to sneeze, covering her face as she bit her lip in utter pleasure.

Sam relished the taste of her salty pre-cum and wanted more. He stroked with more intensity, bringing his tongue all around her head. He brought his lips finally to the head. Almost trying to suck out any pre-cum she might have been hiding. As he did so, he found it natural to bring his lips even further down her head, now finding the whole of her tip in his mouth. Even just the tip felt enormous to him with his mouth wrapped around it.

He stopped stroking with his hand, resting it in a ring around the base of her cock. He brought his mouth further onto her cock, finding it difficult to open his jaw wide enough to accept her giant shaft in his mouth. Still, he persisted, and bringing his mouth as far as he could, began bobbing up and down in steady rhythm.

With her cock pulsing and throbbing in his mouth, he could feel his own cock throbbing.

Jane could feel herself slowly building to an orgasm. She was worried about the sounds she might make when she cums, about the face she'd pull. Her sexual partners had always enjoyed that it was easy to tell when she was turned on, but that asset would be a detriment in this situation. She had been incredibly distracted, but she had managed to maintain pleasant conversation with her parents without seeming too strange. Still, that orgasm was building and building.

Sam figured he must have been getting close, and increased the intensity with which he was blowing her. He brought his hand in sync with his mouth and gave it everything he had.

He stroked and stroked until he could feel her balls tighten up and her legs tensing, every muscle in her body preparing for the oncoming orgasm.

Jane, feeling her body tense up, tried to subtly cover her mouth as if she were just casually feeling her chin. She was at her most visibly distracted, nodding along to her parents in an attempt to minimize the amount of words she was using.

Her breathing increased pace and her toes clenched and as Sam bobbed vigorously on her shaft she blew her first load of hot salty cum. It caught Sam by surprise, hitting the back of his throat and almost making him choke, but he was determined to not get any on the floor, to not miss any of her fresh cum.

As she orgasmed, Jane tried to control the contorting of her face, landing somewhere between normal and ecstasy to a face that seemed to convey to her parents concern and confusion, but moreso something deeply, physically felt. She'd stopped talking even though it was her turn to reply.

At the same time, Sam kept his mouth still but kept stroking with his hand as more loads shot straight into his mouth. Mouth full, he had to swallow the first load, surprised by the sensation her cum made in his throat. He slowed his stroking and swallowed the second load. He took his mouth from her cock and now tried his best to squeeze every last drop from her head, lapping it up anxiously with his tongue. It was gratifying, like tasting her very pleasure.

"You okay, Jane?" He dad asked.

She snapped back to reality. "Yeah, yeah, totally. Sorry, long day at work, I'm getting a little spacey."

"Well, we'll leave you to it, then. Have a great night, sweetey!" Her mom blew her a kiss and her dad waved bye-bye.

She gave a wave herself and finally hung up the phone.

When she was sure she was no longer on camera she immediately fell limp in the chair and let out a loud sigh and moan, as if she were holding them in the whole time.

Sam kept his focus on her cock, making sure to get every last dribble.

After a moment of calm, she finally looked down at Sam.

"You better not have gotten any on the floor!" She chided him semi-seriously.

Sam took a final lick of the tip of her penis, getting what was now the last drop of post-cum. "Don't worry, I got every last drop." he said with pride.

"Such a little slut." She said, impressed. She gestured for him to get up from under the desk. "Come up here you little slut."

Despite her orgasm she was still quite erect and quite turned on.

As Sam got up he realized just how hard on his knees the blowjob had been. He laughed at himself. Low cost to pay, he thought.

He was of course, still rock hard in his own jeans.

He got up and Jane had him sit on her lap so that they were facing each other. He was lighter than she'd expected, and found him quite comfortable on top of her.

She gave him a deep kiss, feeling the heat from Sam's exhausted mouth, and tasting a hint of her own cum.

Sam broke from the kiss.

"Your parents seem like nice people." Sam laughed.

"I can't believe you did that." She said.

"Hey, I asked first." He smiled. "And besides, was it such a bad time?"

"It was amazing." She said. "I've never gotten a blowjob that good. But, in the future let's save it for after I talk to my parents. Deal?"

"Deal." He said, trying to convey that he took her seriously.

She smiled at him.

"Now, what do we have here." She felt around for his penis, easy to find sticking out of his jeans.

He let out a soft moan. She undid his belt and threw it to the side. She then unbuttoned his jeans and zipped down the fly, now feeling his cock through one less layer of clothes. He was wearing short black boxer briefs. Jane dug out his cock from the fly of his boxers, making sure to get out his balls as well. She found it difficult to do because of how hard he was.

"Someone was having fun down there." She said with a sly grin. "But you didn't stroke yourself. You must have been so focused on pleasuring me. Is that so?"

She began stroking his cock gently, prompting him to look up and moan in pleasure

"I asked you a question." She said in a commanding affect and took her hand off his cock to bring his chin down to face her.

"Yes ma'am." He said earnestly.

Jane couldn't help but break character and giggle at her own commandeering persona.

"Well," She started. "How about I return the favor?"

With that, she began stroking his cock again. Sam knew it wouldn't take much for him to orgasm. He'd built up so much steam blowing her.

She commanded him to take off his shirt, which he quickly obliged, undoing each button haphazardly, and eventually letting the shirt fall to his shoulders to reveal his chest, which was at perfect head level for Jane.

She leaned forward and brought her mouth to his right nipple, surrounding the areola with her lips and licking at the nipple directly with her tongue. This sent a shot of pure pleasure directly to his penis, making it twitch in her stroking hand.

He began involuntarily moaning as she brought him close to orgasm. She could sense his muscles tensing up in preparation for an orgasm. She took her head off his nipple but kept stroking.

"Are you going to cum for me?"

"Yes, I'm so close." He said, not hiding any desperation.

"What makes you think I should let you?"

He laughed between moans. "You do owe me, remember?"

"Hmm, I guess you're right." She let out a slight laugh.

Noticing her own cock was hard again from giving Sam a handjob, she brought his cock to hers and began stroking them both at the same time.

"Whoa, what are you doing?" He asked in astonishment. "It feels...weirdly good"

"It's called frotting. You'll love it."

As she stroked their cocks together, they each enjoyed the sensation of each other's cocks hitting against themselves, contributing to their mutual pleasure. They moaned in unison.

Not wanting to clean herself of his cum, however, and having an already sore cock, she went back to just stroking his penis.

"I'm gonna cum so much for you." He said in a submissive voice.

"Of course you are." She said with a smile.

She pushed him back so that he was leaning more against the desk.

Finally she increased the speed of her strokes and brought him to a shattering orgasm. He shot load after load upon his own stomach, reaching his nipples and making him moan loudly.

He took a moment to catch his breath as Jane let go of his cock, still shooting the occasional spurt of cum onto his belly.

"Well, fun night for both of us, then." She said, gesturing Sam to get up.

He obliged and she guided him out of Holly's room.

"I can't believe we did it in her room. I feel like a dick." Jane said. "But then, she's probably done it in my room."

Sam laughed. "I guess you two have shared a lot."

"Yeah, I guess so. She can be annoying, but she's a good friend."

She handed Sam some tissues to clean himself up and went to start up the shower.

He wiped all the cum he could find and gladly hopped in the cold shower.

While Sam showered, Jane checked Holly's room for any stains or smells and made sure everything was back in its place.

Sam stepped out of the shower. Jane had placed a light lavender towel ready for him as he got out. He quickly ran a towel around his body. He'd put his hair up in a pony-tail to avoid getting it wet. He wrapped the towel around his waist and walked into Jane's room, where she'd been digging through her albums for something to play.

As he walked in, Jane took a moment to appreciate his body. She could see the hint of an adonis belt peaking above the towel and his chest and neck muscles all came together perfectly.

"Why do you dress so poorly" She asked, retreating from the album crate and laying at the head of the bed, wearing panties and an oversized Van Halen shirt.

"Gee...thanks?" He said in sarcastic confusion.

"I mean, you're so fucking hot, why don't you show off more?"

He put his hand behind his head bashfully, revealing the arc of his shoulder muscles and biceps.

"I don't know, to be honest." He said. "I guess I was never that confident in myself, and guys get to get away with looking a little schlubby, I suppose. Girl clothes are all tight-fitting, body-hugging...guy clothes are all baggy and lame."

"Believe me, I know." She said, recalling her pre-transition days.

He caught his reflection in her mirror. "When I dress like a girl, I get to admire my body, but it's almost like a type of game, like, it's not really me, but some alternate universe version of me. Sometimes I wish I was born a girl, or rather, sometimes I wish I just 'was' a girl. Sometimes I'll see girls at the gym and I won't think 'she's so hot, I want to have sex with her,' I'll think 'she's so hot, I want to 'be' her."

"That sounds a lot like dysphoria."

"Sure, but dysphoria doesn't really go away right?"

"Yeah, I mean besides after transitioning."

"Right, sorry, that's what I meant. With my thing, it ebbs and flows and usually only flares up when I'm alone and horny. At those times, I wish I had a magic button that would turn me into a girl, and another button to turn right back when I want to. It's weird."

"It's not that weird." Jane said, seriously. "I'd have fucking killed for a button like that before my transition."

"But you wouldn't want a button to change back, right?"

Jane thought for a moment then said resolutely: "No, never."

"I don't know what to make of it for myself. I'm mostly fine with my gender, but sometimes I feel its constraints chaining me down." He sat himself down at the edge of the bed.

"Well, how was it wearing panties out to lunch the other day?" Jane asked.

"It was...fine, anticlimactic." He paused and laughed. "It kind of just felt like wearing underwear that couldn't really support my penis."

"Welcome to my world!" She cracked up. She brought herself next to him, sitting at the foot of the bed.

"But you like it?" He asked earnestly.

"Like wearing unsupportive underwear?" She scoffed. "No, it's not that simple. It...it just feels...right, like it's the way I'm supposed to be. It feels natural. Do I like that part? One hundred times yes; I wouldn't give it up for anything.

Part of me was worried before my transition that I'd regret it, but here I am only wishing I'd done it sooner." She smiled and turned her head towards him.

"Is it bad that I'm a little envious of that?"

"Bad? Not necessarily, but it does undersell the whole process. It's not easy, Sam, at all. I don't think I can convey to you just how world-shatteringly difficult a thing it is to do, and my experiences fall on the better end of the spectrum! My parents were on my side the whole time, most of my friends were chill about it, but it's still so, so much."

"I can only imagine."

"That's right." She said with an almost vindictive tone. "You can only imagine."

"I didn't mean to be insensitive." He said. "I just don't know where that leaves me."

"Well, look, I'm pretty confident you're not trans, but I think it's fair to say that the cis binary doesn't describe you well, and that's totally cool. You can mess with your gender expression and identity to what best suits you. But you can't carry this shame with you all the time. I just know it'll tear you apart your whole life. That's what I've been trying to help you deal with. It's what I was hoping encouraging you to experiment would yield."

"It was never going to go away overnight." He said. "But I appreciate that you're trying. It means a lot. You shouldn't have to deal with my bullshit."

"Yeah, well, I like you." She took his hand in hers. "And I keep feeling like this thing could go somewhere. So, we're going to have to deal with it sooner or later."

He smiled deeply and could feel himself beginning to well up. He brought his head to hers and let himself rest in that space.

"Shit, I didn't bring any clothes." He paused. "Can I...borrow some of yours?"

"Of course." She said, pushing him down to the bed and giving him a big kiss before grabbing a pair of boy shorts from her dresser. She threw them to him and turned off the lights as he put them on.

She crawled back into bed.

He nestled into the crook of her arm and they both went to sleep, breathing soft and gorgeous together.