Jess was a Bitch Ch. 05

Jess and Jon deal with the fallout of their encounter with Caitlin and Travis.

This chapter was finished, other than editing, before I posted chapter four. I have not made any major changes based on the comments posted about chapter four but I have added emphasis regarding some of the topics brought up.

Having said that, this is a story not an essay. My hope is the dialogue between Jess and Jon is a reasonable reflection of what a couple in their situation might discuss.

Enjoy. I appreciated the thoughtful comments the previous chapter generated. Those are always welcome.

Thanks to LarryInSeattle.

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Jon scrambles away from Jess, almost spilling Caitlin on the floor. Travis reaches out to steady her. As Jon's cock pulls out of Caitlin's ass he feels something warm flow over his thigh. He edges away from the bed, hands over his crotch.

"Jon, what's wrong?" Jess hurries toward him. He shrinks away from her touch. "Jon?"

"Why did you do that?"

"Do what?"

"What do you mean, 'do what'? Put his cum in my mouth!"

"But we've done that. I thought you liked it," Jess protests.

"It's not the same when it's another guy's," Travis offers, sitting on the end of the bed. Caitlin moves around to lie with her head in his lap. "Jon, sorry, man. I would have warned Jess but I didn't know what she was going to do."

"That's what's bothering you?" Jess wonders. "I don't get it. You're okay with me eating Caitlin's pussy and then kissing me but a little cum bothers you?"

"Jess, hey, ease up," Caitlin suggests. "This is all new, especially for Jon. It sounds like a lot has changed in just a few days. Guys, in my experience, are very touchy when it comes to anything the makes them seem or feel 'gay'." She rolls her head over to look up at her husband. "You wouldn't believe how long it took Travis to admit he wanted to suck another guy's dick."

"I don't want to suck anyone's dick; that's the fucking point," Jon snaps. He glares at his sister. "Putting his cum in my mouth is the same as you forcing me to suck his dick."

"Oh, bullshit, Jon. I would never make you do anything you didn't wanna do. I'd never make you do anything. Don't you know that?" Her voice, initially full of irritation and defense is now only full of concern. When she touches his arm again, he doesn't pull away. "Jon, I'm sorry. I truly thought it was cool, that it would be, you know, hot. Why didn't you say no, or turn your head or something?" She's careful to keep any hint of accusation out of her voice. "I'd never force you to do something. Don't you understand that?"

"I didn't know what was happening," Jon tells her. "It never occurred to me that you'd do that, do something like that." He looks at Travis. "I don't have anything against gay people, or bi people. I really don't. It just doesn't appeal to me."

"Dude, seriously, don't worry about it. No one is blaming you for getting freaked out. I don't take it as a sign of homophobia, or biphobia, if that's a word. It's not your groove. Fine. I like sucking a guy's dick but I'm not into having another guy fuck me. I don't mind getting pegged by Caitlin but I don't want another guy's dick in my ass. Does that make any sense? It doesn't really make sense to me but that's the way it is."

Jess wanders over to the patio door and gazes out at the ocean. Jon starts to reply then freezes.

"Don't move, please," he whispers. Of course, Jess turns to look at him. Travis and Caitlin already are. "Jess look back at the ocean. Please?" He turns to the couple on the bed. "I want to snap a picture. I won't post it or anything creepy like that. I have an idea. Please?"

Travis looks at Caitlin. She shrugs. "Okay, Jon. What's your idea?"

Jon rummages through the pile of clothing in the suite's atrium, looking for his phone. "A painting," he answers. He finds his phone and hurries back. "Jess, lean against the door again and look out at the beach like you were." Travis and his wife haven't moved much. Their expressions have changed but not their positions. Jon closes his eyes, picturing how they had been looking at him, burning it into his brain. It might fail. He might find himself staring at a canvas, unable to re-construct the look on their face. It's happened before but, as with his vision of Jess and his mom, the picture he sees in his mind is vivid. He snaps a couple of pictures, checks the camera, and sighs. He's captured the scene as best he can with a camera. Now, he needs paint, canvas, time, and if he's lucky, his muse will stick with him.

His earlier panic is gone, burned away by his excitement. He's not sure he can wait until he gets home. His fingers already itch for a brush.

Caitlin smiles at him. "Wow, that's quite the turn around. You paint?"

"I try," Jon admits, suddenly feeling embarrassed. He's not sure if that's because he feels like a fraud, pretending to be an artist, or because of Caitlin's comment about the sudden change in his mood. He shifts his gaze from Caitlin to Travis. "I didn't mean to lose my shit like that. I like you, both of you," he says, looking at Travis. "My brain understands why women find you attractive but I don't feel, like, any urge to do stuff, sex stuff, with you." He shakes his head. "I mean, we were doing stuff together to the girls but not to each other, that's what I mean. Does that make sense?"

"Totally," Travis says, nodding. "Dude, what have I been telling you?" He brushes the hair back from his wife's face. "I'd totally love to suck your cock. I'm not going to lie about that but it's cool if you aren't into that. What I really want is for you to fuck Caitlin again. She denies it but I know my dick is too small for her."

"That's so not true!" Caitlin cries, rolling over to look at her husband.

"Yeah, it is, babe. It's okay."

Jon had noticed that Travis wasn't very big, probably less than five inches. Jon knew, having measured and researched, that he was a little, a smidge, well, maybe more than a smidge, above normal for length.

"I wish you wouldn't say that," Caitlin continues. "It's bullshit. I love your dick. I love the way you fuck me."

"I didn't say you don't, babe. I believe you. But, I also know that sometimes you like to feel totally filled up with cock and my cock doesn't give you that sensation. It's cool. I love watching your face, like just now, when you had my cock in your pussy and another in your ass. Jesus, the look of joy on your face is enough to make me cum just looking at you."

"What does it feel like?" Jess asks, turning from the window. "Having two cocks in you, does it hurt?" Fucking her in the ass was something Alex had pushed for. She had always denied him. She told herself at the time, it was because anal was gross; now she understands that on some level she had never trusted Alex.

"It shouldn't," Caitlin tells her. "Not if you take your time and do it right. If you do, well I can't describe it. I know women who've really tried and just don't like it. Not me. It's not something I need every time I make love but as a treat? All I can say is - goddamn." She draws the last word, making it last. Jess smiles. "Is it something you've been interested in trying?" Caitlin asks softly. Jess nods. "Come lie down then," Caitlin tells her.

"Uh, don't I need to get cleaned up or something?" Jess asks, looking worried.

"Not for this, no." Caitlin pats the bed. "Come on, lie down here." She turns to Jon. "Join us? No pressure, this will be more like a massage than sex but no pressure." Her smile is so open, Jon moves toward the bed with a shrug.

"May I?" Travis asks as Jon stands by the bed. Jon looks at him, confused. "May I join you guys?" Jon nods, then kneels on the bed and moves to sit, lotus-style by Jess's head. Travis moves to the other side of the bed, the two women between them.

"On your tummy, girl," Caitlin tells her. Jess rolls onto her stomach and rests one hand on Jon's crossed ankles. He puts a hand on her head. "Baby, toss me the oil would you." Travis stretches out on the bed and reaches into one of the bedside table drawers. When he sits up, he hands a bottle of clear liquid to his wife. "This is massage oil not lube," Caitlin explains, showing Jess and Jon the bottle. "You shouldn't use this as lube. I mean it will work but it's hard to wash off. If you're swinging with someone you don't know, not all condoms are compatible with non-water-based lubes; be careful." Jon starts to open his mouth. Caitlin cuts him off. "We're taking anti-retrovirals as prophylaxis. If Jess, or if the two of you I mean, decide to let Travis fuck her, he'll use a condom, for her, not him. We both do when we're on vacation. At home, we use rapid STD kits. They're not perfect so we use the prophylaxis regimen, too." She passes the bottle to Jon. "Squirt some on my hands, Jon. Thanks." He does. She rubs her hands together. "If we were doing this right, I'd warm the bottle up first." She places her hands on Jess' lower back. "Is that too cold?" Jess shakes her head. "No," she whispers. Caitlin looks at her husband. "Trav, put some oil on Jon's hands." She smiles at Jon. "You can help. That'll make Jess feel more comfortable."

She begins to massage Jess' lower back, moving her hands when Jon's join her. "Mmm, that feels nice," Jess whispers. Caitlin's hands move lower, to the top of Jess' butt; Jon's follow. Soon, they're massaging Jess' ass. She murmurs her contentment. "Follow me," Caitlin instructs Jon. She fans the fingers of one hand and rolls her wrist, dragging each finger, one at a time, up Jess' ass crack. Jon does the same, then Caitlin follows with her other hand. He gets the idea. They alternate - Caitlin, Jon, Caitlin, Jon. Jess feels a seemingly endless wave of fingers caressing her crack. She presses her ass up. Caitlin's hands shift slightly. Jon copies her. His fingertips glide over his sister's asshole. Jess moans.

"Okay, Jess, I'm going to touch you. Is that okay?" Caitlin asks softly.

"Uh-huh."

"Good. I'm only going to touch. Jon spread her cheeks, just a little. Easy, just a little. Okay?"

He nods. His hands pull. He's seen his sister's pucker before. He'd tried to kiss it. This is different. He feels his cock stirring. He uncurls his legs, moves lower in the bed. Jess' ring is pink. It shines from the oil. Caitlin presses the tip of her finger against it. It twitches. She begins to rub it, up and down and in circles. Caitlin catches Jon's eye, nods at Jess' ass, raises an eyebrow. From where he's sitting it's easier to rub her with his thumb than his finger. "Mmm," Jess sighs, acknowledging the switch. Jon is surprised at how firm the ring of muscle is. He shifts positions, stretching out along his sister's side, his head toward her feet. He rests one arm across the back of her thighs and rests his cheek on his arm. He touches her with his index finger and begins to massage.

"How you doin' up there, girl?" Caitlin asks in a soft voice.

"Mmm, fine, good, I'm good."

"Trav, squirt a little more oil on Jess' tush, babe." She looks at Jon. "After you've fingered someone's ass don't go back to their pussy, same for your dick. If your dick has been in her ass don't put it back in her pussy, not unless you wash or change condoms. It's a great way to get a UTI. You want to keep the bottle clean, too. Put some oil in a bowl."

"I wanted to kiss her, kiss her down there, last night," Jon whispers.

"Did you? Good for you. I wouldn't now. This oil doesn't taste very nice. If I'd known, I would've had you get her wet with your mouth."

"Uh, after, do you..."

"Brush my teeth, rinse my mouth?" Caitlin smiles. "Not usually. I know, I just told you not to go from ass to pussy but your mouth already has a lot of bacteria. So, no, if I rim Travis, I don't go brush my teeth or anything before I suck his dick." She smiles at her husband. "Or kiss him. If some asshole, no pun intended, thinks their ass is too dirty for you to kiss them after rimming them, then it's too dirty to rim, tell 'em to fuck off and move on." Travis has been waiting. She nods and he squeezes some oil into Jess' crack, just above her asshole. "Smooth that over her gorgeous hole, Jon." He does. "Push a little harder. Don't try to put your finger in her, just add a little pressure to the massage." He does. Jess arches her back. "Nice, huh?" Caitlin asks her, stretching out to lie beside her. Jess nods.

Caitlin pushes Jess' hair away from her face and moves closer. They kiss. Caitlin fingers her own clit. She pulls away from Jess. "That's probably all the work we should do on the back porch, until you have time for a little prep. That okay?"

"Sure," Jess whispers.

Jess looks at her brother. "Do you want to go, babe?" He nods, cheeks flaming.

Travis leans past his wife and kisses Jess on the shoulder. "It's cool. I appreciate, we both appreciate, the two of you letting us share your love and enjoyment of each other. If it works out, maybe we'll try it again some time."

Jon nods and climbs off the bed. He's pulling his trunks on as Jess climbs out of the bed. "Uh, thanks, I guess? Has Miss Manner's weighed in on the proper way to say good-bye after group sex?"

"I think, see ya, good-bye, later, any of those work." Caitlin tells her as she hugs her. Jess slips back into her suit. She kisses Travis on the cheek and joins Jon at the door.

***

"I'm so sorry. I'm such a baby, a fucking dork..." he starts as soon as the door closes.

Jess kisses him hard. "Hush, you aren't, so stop it. Let's go to our room and relax. I'm the one who should apologize. It was too much, too fast. I wasn't paying enough attention to how you were reacting. I was the one being stupid. I got carried away. I truly thought it would be fun. I'm sorry about that. Don't make me feel worse by imagining it's your fault somehow. It's not, so stop." She puts an arm around his waist. "Come on, silly. Let's get out of here." They only go a few steps when Jess stops. "Hang on a sec. Be right back." She hurries back to the door, knocks. When Travis answers, Jess asks to speak to Caitlin. They talk softly for a minute. Caitlin smiles. Jon hears her tell Jess to "just relax and it'll be fine".

"What was that about?"

"Oh, just girl talk." They walk on. "I asked her what she meant by 'a little prep'. I want to go further, you know, back there but I'm not sure how. That's all. I don't want you worrying I'm plotting something. Well, I am but it's for us, for me, not with them."

"It's cool, Jess. I wasn't worried you were going behind my back. Thanks for telling me though." He squeezes her hand. "I'd like to try more, too, if that's what you really want."

"I do."

"So, what do we need to do?"

"Uh, I'd prefer not to go into details, if that's okay. It's pretty simple, really."

"Sure, I mean, that's cool. If you need me to, you know, whatever, uh..."

"I will, dork," Jess giggles and leans against her brother's shoulder.

***

"You go on in. I need to run to the lobby for a few minutes. Don't take a shower. Wait till I get back. Okay?"

Jon nods and opens the door. He watches Jess hurry down the hall, shrugs and enters the room. He doesn't shower but he does wash his dick at the sink. He doesn't see anything, which surprises him a little. He runs the sink full of warm water, dips the soap in it a few times and then soaks his trunks and the Speedo. He rinses them, squeezes them dry, no wringing, and pads back through the room to lay them to dry over the back of one of the patio chairs. He stands there, naked, for a moment. He's surprised to discover he hopes someone looks at him, sees him naked. He shakes his head and goes back inside, leaving the door open.

***

Jess feels ridiculous. She's sitting in the ladies' room in the lobby. Caitlin had told her all she really needed to do to prep was - poop, then shower really well 'back there'. She told her she only used enemas if she knew she was in for a lot of anal play. Yes, she had used an enema before approaching Jess and Jon. Yes, even so there might be a little 'mess'. She warned her again not to go too fast. "You aren't ready to let Jon put his dick in your butt," was the way she phrased it.

Jess covers her face with her hands and concentrates on why she's there. She had stopped and picked up a travel pouch of Handi Wipes at the shop in the lobby. She wants to make sure she is already pretty clean before getting in the shower with Jon.

***

Jon walks in from the patio, naked, as she's closing the door.

"Are you teasing your big sister?" She hurries to him and wraps her arm around his body. He feels so good there. He's just the right height for her head to fit comfortably under his chin. "Come on, let's get cleaned up, relax, and then swim or go get something to eat. What ya say?"

He squeezes her back and kisses the top of her head. He feels himself getting ready to say he's sorry again and swallows it. "Sounds like a plan. You can't shower in this." He lifts the gauzy beach wrap over her head. He helps her out of her suit. He rinses it in the sink, as he had his own. This time when he takes the suit outside to dry, he's half-hard. He takes Jess' hand and leads her to the bathroom. They brush their teeth and hop in the shower.

They take their time, letting the water and their touch ease away the last of the tension. Jess' hands are on his chest. He pulls her close and turns her, so that her back is out of the water streaming from the showerhead. He fills his hand with body wash from the dispenser on the wall and his soapy fingers begin to work at her ass. Jess rests her hands and face against her brother's chest as his fingers probe deeper. Her fingers tighten slightly when his fingers brush over her asshole. She consciously relaxes, letting her body sag against his hand.

"That feels good," she whispers, ensuring there's no misunderstanding. The pressure against her backdoor increases. She rubs the side of her face against his chest. Her sphincter softens and just the pad of his finger enters. He's not penetrated her, not even close, but his finger is no longer simply rubbing the surface.

"That hurt?"

"Uh-uh, it's fine." She lowers herself. He presses and a little more of his finger is inside of her. "Jon, just hold your hand still, okay?"

"Of course. Tell me what to do."

"Just what you are. Hold me."

She eases herself onto his finger. There's no pain but she has to remind herself to relax. It takes time before she understands that in order to relax back there, she needs to bear down a little. She's paralyzed for a moment by the horrifying thought of passing gas while Jon has his finger in her ass.

"Move your finger, okay? In and out."

He does, as gingerly as if he were defusing a bomb. "Tell me if I hurt you," he whispers. She nods. They discover that soap is not a great lubricant. "I think that's enough," she whispers as she kisses his chest. "I should be clean, don't you think?"

Jon eases his finger out. Jess is surprised that the most uncomfortable moment is when his finger leaves her. She turns back toward the shower and thrusts her butt under the water. She soaps her own hand and washes her crack and hole, probing it again, then hold her cheeks open and lets the water rinse her. She soaps her hands, washes Jon's hands, clasping them between their chests as they kiss. A final rinse and Jon shuts the shower off. He dries his sister's body with one of the large fluffy towels as gently as if she were a new born babe. She dries him with the same care, stopping to kiss and briefly swallow his erection.

They make their way to the bed. The sheer curtain over the patio door billows, allowing in the sound of the waves, the constant cries of the gulls, and the rustling of the palms. They hear not one sound produced by humans, no voices, no sound of jet skis, fishing boats, or planes. They feel as if they've been transported to a deserted isle.