Jake and Jessica – Sweet Brothings – NSFW

Chapter 6 – Sweet Brothings – NSFW

Chapter 1 – The Annihilator (NSFW -Explicit sex)
Chapter 2 – The Annihilator is Dead
Chapter 3 – It Was a Good Day
Chapter 4 – The Jake Must Go On
Chapter 5 – A Daring Rescue

“What’s the deal with this Kesley thing?” Jake asked, passing the pipe.

Jess used the butt of the lighter to mash the remaining weed back in the bowl and smoked carefully before answering.

“What Kelsey thing?”

Jake scoffed. “Do I have to spell it out?”

“Jake, when a girl likes another girl, they do a very special hug…”

He rolled his eyes. “Jess, this is serious. She brought you flowers.”

She set the spent pipe on a coaster. No sense in ruining the coffee table. Her and Jake used to talk about girls together all the time, but that was different.

“I don’t want to talk about it.”

“I always tell you about the girls I fuck.”

“I know.”

“You want me to stop?”

She thought about Amber, collapsed in a heap over the back of the couch, then imagined herself telling Jake about Kelsey in a similar situation, but ended up thinking instead about how Kelsey would sometimes cry when they only talked about fucking, how she so delicate in her arms that Jess fantasized about keeping her there in her safe bed and giving Kelsey pieces of her own heart to shore her up for the outside world, how she cherished every second of Kelsey’s pleasure and happiness like it was the very air she breathed.

She thought about how Jake took so much for granted. It was easy to brag about fucking girls until they came, it was easy to argue technique and talk positions, even to laugh together over sex tricks gone hilariously, sometimes horribly wrong. All the women they fucked and talked about fucking were so simple. Or at least they had seemed simple.

College was a blur of finding girls who wanted what they had to give and giving it to them. Every encounter had all the grace of a pizza delivery.

“It’s different.” She said instead.

“Is it the dick thing?” Jake asked. “You know that shit doesn’t bother me, we used to listen to Marco’s stories all the time in school.”

Marco’s stories about men had been the same as everybody else’s stories about women. Even when he was the one being pursued, he was just on the other end of the Pizza.

“You know I kind of fucked him once.”

Jake made an ick noise.

Jess raised an eyebrow.

Jake started to stammer a string of purposefully non-homophobic completely supportive phrases and sentences that only seemed to jam his foot further and further into his mouth with every word.

Jess kept a straight face for as long as she could, but then burst out laughing.

“Oh thank God” Jake said. “I thought you actually did it.”

“I did!” she said.

Jake sobered, looking both confused and worried until Jess relented and said “It was so weird, dude”

They collapsed into the couch in uncontrollable fits of laughter.

When he finally caught his breath Jake said “So…?”

It had been New Year’s, a few years after graduation, but a few years before transition, and Jessica had been drunk, but not that drunk. She’d run into Marco at a party that she’d gone to with another friend who immediately ditched her to get laid. Marco was in the same boat, and they ended up having an amazing time, so when he suggested they leave early to go get some food, she’d gone along. The conversation had continued at the restaurant, and when Marco invited her back to his house, she’d agreed happily, fairly certain in the knowledge of what would happen next.

“And then we kind of fucked. The end.” She teased.

“Oh come on!” Jake begged.

“It’s embarrassing!”

“I told you about the time I made out with Kevin Dolen!”

“To get his girlfriend to make out with you in exchange. That doesn’t count!”

Jake bit his lip, put on his serious face, and said “I told you about the girl in Manchester Hall.”

Jess had nearly forgotten. Early freshman year, Jake caught the eye of a Sophomore who lived in Manchester hall. The girl did things to him he now considered to be a part of a healthy adult sex life, but at the time his inexperience and naivety had caused him to confess shamefully to Jess in their dorm at night, to which his much more experienced and worldly friend had laughed, and pulled up about ten different websites as proof that what Jake had done was in no way abnormal. The story of the girl in Manchester hall was one that Jake didn’t tell very often.

Being a frightened and aroused eighteen year old under the tutelage of an educated and demanding older woman didn’t really fit the pizza delivery model. Jake had a point.

So, in the spirit of friendship, and in honor of Manchester Hall Girl, she went on.

When they got to Marco’s apartment, he’d been a perfect gentleman. He dimmed the lights, put on soft music, and sat on the couch with his arm around her, just talking and absently rubbing his hands up and down her forearm at first. In hindsight, she realized that it was his courtship, and not his body she’d responded to. Having doors opened for her, having a conversation partner that would absently touch her leg, or rest his arm at the small of her back was a slightly feminine feeling that she hadn’t experienced much of in the past.

She’d played the girl with various girlfriends, but that always felt so achingly artificial. Pretending to be something adjacent to who she was, but never quite getting there. This was different. Marco had her feeling like a woman in a romance movie. Pursued, desired. It was entrancing.

So when he leaned in and gently, almost cautiously kissed her lips, she’d felt soft and small, and all the other delicate female things she’d fantasized about for so long, and it thrilled her. As the kissing grew more intense, Marco reached under her shirt, rubbing slowly up and down her stomach, teasing the waistband of her jeans, but more often than not reaching up to play with her nipples, another thing her regular sex life had not had a lot of.

She’d melted under him then, laying pliant on the couch with her legs wrapped around the backs of his thighs. She sighed high and light when he’d dragged his tongue over the sensitive pulse point on her throat. At first, she’d been appalled by the girlishness of the sound she made, but Marco was either completely unaffected, or used to those results, so she gave herself permission to sigh, and to moan, and to beg for this attentions in whatever way she wanted.

She ran her hands up and down his back, digging in with her short nails when things became especially heated. When his hand strayed down to the button on her jeans, she dragged it back up under her shirt again.

“Play with my tits” she begged, followed by a volley of yeses and affirmative cries when he tweaked and pulled her nipples while sucking and biting her neck, and lips. Her world became the ends of her breasts, the hollow of her throat, and the weight of him on top of her while she drew more of him down to her, hands grabbing and pulling at his hips.

Jessica thought that she could kiss and wrestle under him all night long, feeling him press against her, feeling his large, warm hands on her skin. She moaned and writhed, drinking in the sensations of being so perfectly small and sweet in that moment.

“Hold on.” Marco said, reaching towards their conjoined crotches, she tensed, worried he’d ruin everything by grabbing for her dick. He noticed her apprehension and smirked, slowly sitting up and putting his hand in his own jeans, adjusting his straining cock down the side of his pant leg. “I was getting a little uncomfortable.”

He gestured to her own tenting fly, asking without asking if she wanted to do the same. Quickly, she reached into her pants and flipped her cock under her waistband, exposing the crown of the head, and flattening the sensitive underside against the back of her fly. She stroked two fingers along her length, caressing the skin with the long, petting motion she used when she was alone. She looked up at Marco, invitation and challenge, but also naked, vulnerable need.

He growled and started to grind his cock against hers, she rocked her pelvis up and imagined him fucking into her. She brought her legs higher and reached through them to resume her grip on his hips. In this newly exposed position, the tension built quickly. Marco’s relentless rhythm consumed her and she realized that she had been whimpering and moaning loudly, arching her back to give him access to her exposed throat and chest.

She imagined his thick, hard dick driving into her over and over again. She envisioned her body opening for him. She wrapped her legs around his waist, and her arms around his back, pulling him closer, trying to articulate the primal, universal need welling up inside of her.

Above her, Marco practically cried “I can’t stop.” His voice was frantic. “I wish I was fucking you, Oh God.”

“You are.” She said, as his tempo reached a fever pitch. She rose up to meet him, wanting to feel like this for as long as humanly possible, watching Marco’s face as his eyes rolled wildly and he thrust blindly against her, into her.

The orgasm started in her toes, and it rolled up and around her body in wave after wave of mind-blowing pleasure. She screamed with joy and flew apart under him, ecstatic pieces of her conscious mind propelled themselves into orbit before floating blissfully back to earth. She became aware of herself a piece at a time, and realized a little bashfully that she’d been panting and unfocused for quite awhile.

Marco sat beside her on the couch, a gentle hand running up and down her arm and across her chest. “I’ve never seen anybody cum like that.”

She laughed, and looked down at her stomach, which was covered in uncomfortably cooling spunk, thankful that the shirt she’d have to wear home was scrunched up under her armpits, well outside the blast radius.

Marco, gentleman that he was, ran to get a damp cloth. “I came in my pants” he said, handing it to her. “I can’t remember the last time I did that. That was amazing.”

She wiped absently at her own cum. “Do you..?” She made an attempt to re-fold the cloth so he could use it if he wanted. He took it back, but made no motion to use it, despite the obvious wet spot at the front of his jeans.

“I’m going to go change.” His eyes traveled the length of her body. She’d already pulled her shirt back down around her torso. “God you look so hot.” He hesitated. “Don’t go anywhere.”

She laughed, but as she imagined how Marco was seeing her, a fucked-out frat bro, and not the seductive woman she imagined, a cold, sick dread began to pool where hot desire had washed her only minutes before. While Marco changed into basketball shorts, she took the time to arrange her spent dick more comfortably. This couldn’t happen again.

In the moment, it had been fabulous and intoxicating, but post-orgasmic reason had started to work its way back into her head, and she was nauseous with reality. Details of the encounter that hadn’t seemed that important at the time came flooding back to her. His dick, chief among them with hers a quick second. How could she have let it happen, how could she have been so short-sighted? Since childhood, she’d known two things: that she was meant to be a girl; and that she could never let anybody know this about her. Marco had made her feel more female than anyone else ever had, but now she felt very much like a gay man, despite the fact that she’d always thought of herself as a lesbian.

Revulsion rolled through her, followed by guilt. Marco hadn’t done anything wrong, but she had forgotten herself, and now she dreaded the awkward, uncomfortable interaction she was about to have with a man who was, first and foremost, a brother.

When he came back into the room, she was sitting on the couch with her head in her hands.

“Oh.” Was all he said.

“I’m sorry.” she said, voice muffled by her own hands. Sorry for lying, sorry for feeling this way, and sorry for not just being cool about it. Somewhere there was a guy who would not act like this. Not for the first time, she wished she could be him, and not herself. Anything but herself in this moment.

Marco slumped on the couch next to her. “What happened?”

She leaned back, mirroring his wrung-out posture. “I’m not…” she started to say, but Marco’s incredulous look made her change direction. She searched for some excuse or explanation. Something that would fix everything without ruining it again with what she considered to be her personal damage.

She’d only ever told this to her online friends. Online friends nobody knew she had. Online friends she had deleted at least twice before when it all got too terrifyingly real. She wracked her brain for anything they’d ever said about coming out as a lesbian to the gay bro you’d just had sloppy middle school sex with. Nothing presented itself.

She turned so her back was against the couch arm, a tense, terrible echo of her previous position. From this new vantage point, she was able to see Marco head to toe. She drew her knees into her chest, protecting her vital organs. Since college, she’d stopped lifting, while Marco had obviously kept it up. She couldn’t see Marco ever hurting her, but she felt so much safer as soon as she wrapped her arms around her legs.

She expected anger when she looked at him, but what she saw instead was worry and a mirror of her own guilt.

What did he have to feel bad about? She was the one who had lied.

“Don’t..” look like that? Feel like this? Ask me anything? She couldn’t finish that sentence.

Marco gestured in her general direction. “Did someone abuse you?”

This shocked her. “No! God, why would you say that?!”

“Maybe because you’re curled up into a ball right now and all we did was make out.” His tone was accusatory, hurt. Clearly he’d overcome his brief battle with feeling responsible.

She put her forehead on her knees and groaned. He had every right to be mad, she was a cock tease, and a mess. “I’m just going to go” she mumbled into her legs.

Marco sighed. “I’m sorry, that as a shitty thing to say. If you want to go, I understand, but I’m not kicking you out.”

“Oh, what a kind invitation.” Despite her derision, she didn’t move.

The silence stretched between them, tense and uncertain. Finally Marco asked “Was it something I did?”


“Then what…”

“Is wrong with me?” she raised her head, defensive.

He shrugged an affirmative, as if to say ‘well.. yeah.’ “Because I’ve hooked up with some straight guys in my day, but nobody did this.” He pointed at her. “You look like you’re afraid of me.”

She nodded. If only he knew, he would understand. Or would he? The years of their brotherhood paraded through her head. The shit they’d done in rush alone made up for a large chunk of secrets no one would ever tell.

“I’m not straight.”

“So is this a regular thing?”


Marco circled his hand in the air between them, gesturing for her to continue. She didn’t want to.

She took a deep breath. “Why do you want to know?”

Marco stared

“Because if you just want to know if it’s your fault, or if you’re responsible for something, it’s not. I shouldn’t have come here, I’m sorry I freaked you out, I’m just weird. Really, I’m fine.”

Marco laughed. “You are not fine right now. There’s obviously something going on with you, you look really freaked out and all I care about is making sure you’re okay. Whatever else doesn’t matter.”

She took a deep breath. God, this was so stupid. “I’m a lesbian.”

“You’re what?”

She groaned and buried her face in her knees again. This was such a terrible idea, but the need to be understood propelled the words out of her. “I’m…” she murmured “I’m trans… a woman a-a” and then it felt like all the air was sucked out of the room. Her chest heaved as she tried to breath with no cooperation from her lungs. Her head spun, and she felt incredibly light, and suddenly cold.

Marco’s hands fluttered around her at first, but then he made a decision, and they resolutely grabbed her shoulders.

“You’re hyperventilating.” he said. “You need to sit up straight.”

He coached her to regulate her breathing, rubbing his hands up and down her arms, and looking directly into her eyes until she calmed enough to break into choking, hiccuping sobs, then he drew her into his arms and petted and soothed her until she lay spent against him for the second time that night.

Eventually, they talked softly to each other. It turned out he had a cousin who was trans. She’d come out when they were still in college, but he didn’t tell the frat about it because he was worried about how the guys would act.

Jessica confessed that she had always been a little jealous of him, being out since high school, then the conversation turned toward the good old days, talking shit about keggers and catching each other up on the bros that they’d seen most recently, even as they snuggled on the couch.

After a while they lay in silence. Eventually Marco said “I’ve never done it with a girl before.”

She giggled.

“It was really fun.” He said. “Do you think I might be bi?”

She laughed harder and buried her face in his chest, shaking her head back and forth, knowing that neither of them were.

When she finished her story, Jake was quiet for a moment, then he said “You told Marco before you told me?!”

“That’s what you got from that story? Seriously?”

“I thought we were bros, Jess.”

“And you wonder why I never tell you anything.”

Jake broke into a ‘just fucking with you’ smile. “I miss Marco.” he said.

“We keep in touch. You want me to see if he’s free to hang?”

“Yeah. Let’s see what your old flame is up to.”

Then Jessica groaned and flopped back against the couch.

Chapter 7 – Girl Talk


This chapter would not have been possible without original and biographical works from the trans and gender non-binary people that I would be remiss in not mentioning. I also owe a debt of gratitude to the trans community on Reddit, without them, this would be way shittier.

Bellwether, Mira. Fucking Transwomen. 0 vols. N.p.: CreateSpace, 2013. Print.

Taormino, Tristan. Take Me There: Trans and Genderqueer Erotica. Berkeley, CA: Cleis, 2011. Print.

Bornstein, Kate. A Queer and Pleasant Danger: The True Story of a Nice Jewish Boy Who Joins the Church of Scientology, and Leaves Twelve Years Later to Become the Lovely Lady She Is Today. N.p.: Beacon, 2012. Print.

And to my beta readers, your help was invaluable:

Zoe G. Miller

Sabrina McCoy

Jayna L-Ponder

Some readers may wish to remain anonymous.

JakeandJessica_vol1_minicover Dear Reader,

Due to your amazing support for Jake and Jessica, I have been able to publish Volume 1 on Amazon. Chapters 1-6 are available for $1.49.

At that price, I make about $0.50 a book. I’ve set the price more than a dollar lower than Amazon suggested because I want the story to stay as accessible as possible in all its formats.

You can still read the entire story absolutely free on the blog, and I have no intention of changing that ever. But if you want a more portable, searchable, note-able format, it’s available to you on Amazon. I’ve also made it lend-able, so you can lend it to your friends.

Even if you don’t intend to buy the book, I’d appreciate it if you could go and give me a favorable review so that more people can find it.

Thank you again for your constant encouragement and good will. You guys are awesome.