Jesse wasn’t sure why they had to come into a sex shop. Gas station condoms suited him fine when Tulip didn’t trust him to pull out and they had /real/ handcuffs for when they wanted things to get a little more exciting, no need for fuzzy pink ones designed to pop open. Though as he walked up and down the aisles of sex swings and dick shaped pasta and rubber genitalia that bordered on the line between intimidating and comical, Jesse suddenly got an idea of why he was dragged in here as he saw the box his girlfriend was reaching for. “Tulip…”
“What?” she asked innocently, or as innocently as Tulip could ever look to Jesse, as anyone could really look while holding a box that read “Bend Over Your Boyfriend: Beginner’s Kit (Instructional DVD Included!)”
“You’re not.” he huffed, his voice wavering between a firm order and a nervously hopeful suggestion without his permission.
Tulip grinned. “And why not?”
The grin just made Jesse swallow hard. “Because.”
“‘Because,’” Tulip laughed, knowing she’d already won but wanting to push anyway, as was her nature, “Because… you’re afraid you might like it?”
“I’m not ‘afraid I’d like it,’” Jesse grumbled in protest, knowing as well as Tulip that this battle was a losing one.
The grin on Tulip’s face morphed into a smirk, just on the edge of wicked. “Right, you know you’d like it. You like it when I do the finger thing.”
“That’s different,” he replied with more than a touch of embarrassment.
“How’s it different?” she questioned.
“It just is!,” Jesse insisted, his voice slightly hushed, “That’s just… a little tease. You’re not supposed to be really sticking… things up there.”
The look on Tulip’s face faded to a slightly unimpressed frown that was barely holding back against a laugh that threatened to bubble up. “And since just when have you, Jesse Custer, been a fan of avoiding things you’re ‘not supposed to’ do?”
Even if she hadn’t before, Tulip had him there, and with the smirk that appeared on her face as she watched him scramble for an answer, along with teasing look in her eyes as she gripped the box in her hands, Jesse really didn’t have it in him to deny her. “Fine,” he relented, taking the box from her and tucking it under his arm as they continued through the store.
After picking up a box of assorted condoms, a bottle of lube recommended by the cashier, and a vibrating stretchy cock-ring “just for fun,” Jesse and Tulip made their way back to the small apartment they’d secured for themselves. The neighborhood was a little sketchy, the upstairs neighbors fought a lot and the ones downstairs had a baby, but the door was solid with good locks, and the landlord didn’t check credit, so they couldn’t rightfully complain.
“I’m grabbing a beer, you want one?” Jesse called out as he made his way to the kitchen while Tulip locked the door.
“Yeah, just one though, neither of us are getting drunk tonight,” she called back.
Jesse didn’t protest, returning with two beers and seeing Tulip with the box open and the contents laid out on the storage container that stood in for a coffee table as she put the DVD into their player. “You want us to do that right now?” he asked as he sat down on their couch.
“What?” Tulip shrugged, joining him and grabbing the remote to press play, “Do you want me to wine and dine you before I bend you over?”
“I mean, I’d buy you dinner first if I was trying to convince you to let me stick my dick up there,” he grumbled, handing Tulip her beer.
“Y’know, I’ve never said you couldn’t stick anything up my butt, Custer,” she pointed out as she took the bottle and had a swig from it, “You’re just a goody two-shoes who ain’t tried.”
Jesse raised an eyebrow to that. “Do you want me to fuck you in the ass?”
Tulip smirked. “I’ll let you try it after I do you, deal?”
The moment of silence while Jesse tried to gather a dignified response of some sort to that proved that Tulip could still surprise him sometimes. He didn’t get a chance to answer before Tulip just laughed, grabbing the remote and starting the video.
Jesse’s beer went down far too fast, leaving him to just sit awkwardly, like a schoolboy in sex ed, slowly peeling off the label as the woman in the video gave a lecture about communication and consent, followed by an explanation of different types of lube. He glanced to Tulip, who was watching with rapt attention, and down to her hands as the voice coming from the television continued to narrate about gloves and delicate anal tissues. His eyes continued to trail down to the coffee table and the silicone dildo taking residence on it. It was smaller than his own length, mostly in girth but a bit shorter too, and a pearlecent sort of purple color, not the shade that Tulip favored but purple nonetheless. And he was going to let Tulip put that inside him.
Tulip noticed Jesse just staring at the kit after a few moments and paused the video which had finally moved on from disclaimers and diagrams to educational porn. “Jesse,” she said softly, putting her hand on his thigh and squeezing until he finally looked away from the coffee table and at her, “I ain’t gonna make you do it if you don’t want to. I just thought it’d be fun.”
“I know that,” Jesse assured quickly, shaking his head and putting his hand atop Tulip’s, “It’s just… weird. The thought of getting something put up there. Like I’m a... “ He trailed off before finishing his sentence, noticing the way the look on Tulip’s face changed as the sentence began.
“Like a what?” she pressed lightly.
Jesse took a moment to look sheepish and think of better phrasing than he had been going to use. “It’s just not a position I’m used to being in, alright?” There was a beat where Tulip kept giving him a look before he sighed. “John Wayne never took it up the ass.”
“Fine,” she huffed, hitting stop on the video and letting the blue ‘no signal’ screen come up in place of the frozen image of a woman wearing a strap-on similar to the one on the table in front of them, “I’m still not going to make you do it. Even if that’s a stupid reason. And you don’t know John Wayne never took it up the ass.”
“John Wayne never took it up the ass. I’m sure of it,” Jesse protested, clearly offended.
Tulip rolled her eyes. “Yeah? Did you live up his ass his whole life? Made sure it was Exit Only?”
“Maybe I did,” he replied matter-of-factly and with a little bit of a smile, crossing his arms in front of him.
“Uh-huh…” Tulip shook her head, sighing a bit as she changed the tv input and the evening local news started playing. She shifted on the couch so she could curl her feet up under herself, taking a moment to kick at Jesse’s leg. “Well, if we’re not fucking tonight, go grab me another beer,” she muttered, only cracking a smile when Jesse got up and did as she requested.
The strap-on kit remained untouched on the coffee table for three days before it was mentioned again.
“There a reason this is still laying around?” Jesse asked with a gesture and a sigh as he and Tulip settled down after dinner.
Tulip shrugged. “Not really. Just haven’t put it away yet. It bothering you?”
“It’s a dildo, Tulip,” he half whined, “You can’t just leave a dildo on the coffee table. Someone might see…”
“Who? Not like we ever have company over to see anything in this place.” Tulip countered, “I could leave a thousand dildos out and no one would ever know.”
“Fine, leave the dildo out,” Jesse relented, mostly grumbling under his breath, turning on the tv.
The drone of a syndicated sit-com filled the apartment for a few moments before Tulip looked over at Jesse. “Does it make you uncomfortable?”
It took for a moment for Jesse to realize he’d been spoken to and what Tulip was referring to before he could respond. “No. I just don’t know why you’re leaving it out. You waiting for me to give in and let you use it on me or something?”
“I don’t want you to ‘give in’,” she huffed, “I just don’t know why you let me get it if you were so against the idea…”
“Why did you want to do it so bad?” he huffed in return.
Tulip just looked at Jesse for a moment, shaking her head. “Cause I’d thought it would be fun! You like the finger thing, I didn’t think you’d have a fit about it.”
“I didn’t ‘have a fit about it,’” Jesse protested, “I just… men don’t get fucked.”
Tulip made a face at that. “Men get fucked all the time, Jesse. You’ve just got a huge stick up your ass about having anything else up there ‘cause you think it’d make you less of a man.”
Jesse frowned at the look on Tulip’s face, crossing his arms over his chest defensively. “Why’s it such a big deal to you anyway, huh?”
“Because it’s stupid that it’s such a big deal to you. Look, Jesse, tell me straight out that you don’t want to try it, not that ‘John Wayne never took it up the ass’ or that you’re afraid it’ll make you a girl or any of that shit,” she said simply, “Tell me you just don’t want it and I’ll drop it. Stuff it all back in the box and toss it in the dumpster in the alley, never bring the idea up again.”
A commercial advertising a chicken sandwich filled what would have been silence until Jesse broke it. “...And what if I don’t want to say that?” Jesse asked carefully, his posture still defensive and looking half ready to stand up and walk out.
Tulip held back a sigh, though just barely. “Then it stays on the table. Literally, I’m leaving it out, and y’know, figuratively. We don’t gotta do it tonight, or tomorrow, or next week even. But you can’t have a crisis about your manliness or any of that shit. You’re still Jesse Custer, my boyfriend, who I love ‘til the end of the world, even when you’re an idiot, no matter if I’m underneath you or on top of you or behind you with you on your hands and knees. Understand?”
There was another would-be silence, this time filled with a new car ad, until Jesse let out a breath and nodded, uncrossing his arms in favor of wrapping one around Tulip. “Yeah, I understand.”
It was the middle of the next week before the subject was brought up again.
“If you wanted to, tonight, you could do that thing you’ve been wanting to do,” Jesse attempted but failed to say casually as he wrapped his arms around Tulip from behind as she stood at the bathroom sink, brushing her teeth.
Tulip spat a mouthful of toothpaste into the sink and turned on the water to rinse it down. “What thing?” she asked before cupping her hand under the faucet and getting enough water to rinse her mouth.
Jesse squirmed a bit as he replied. “The thing. With the thing on the coffee table.”
“Oh, you mean the taking you up the ass thing,” she laughed, turning around in Jesse’s arms and leaning up to kiss him before he could object to the phrasing. “Yeah, I could do that thing tonight. Brush your teeth and come lie down. I’ll get everything ready.”
With that, Tulip slipped out of Jesse’s arms and into the other room, leaving him to take his time in the bathroom working up the courage to join her.
Eventually, Jesse did make his way into the bedroom to be greeted by the sight of Tulip lounging on the bed nude save for the strap on slung low on her hips.
“Took you long enough,” she laughed, gripping the dildo at its base and giving it a teasing stroke before laughing at herself. “Do you feel this ridiculous when you do that to me?” she asked, grinning.
“No, mine’s attached to me. Makes it less ridiculous,” he managed, tentatively stepping towards the bed but stopping at the edge of it.
Tulip noted how Jesse was hesitant, even if he was less nervous than when he’d first walked in the room after responding to her, and rolled her eyes. “Jesse, relax,” she sighed, “I watched the video, and I’ve been fucked before, I think I’ve got a good handle on this.”
Jesse frowned a bit, but nodded, “Alright. I trust you. Just… tell me what to do.”
“I like hearing you say that,” Tulip teased lightly, patting the spot on the bed next to her, “Hands and knees. It’s supposed to easier that way.”
Taking a deep breath, Jesse settled onto the bed on his hands and knees stiffly, before yelping at a playful smack to his ass.
“You trust me? Then act like it,” Tulip said firmly, giving Jesse’s ass a squeeze before tugging at his underwear, “Relax.”
“Relax, right,” he managed, trying to force himself to relax and somehow making himself more tense.
An annoyed sigh escaped Tulip’s lips as she paused for a moment before pulling away from Jesse. “Yeah, it ain’t gonna work like this.” There was another pause before she smirked, “Roll over.”
Jesse made his own noise of frustration, then one of confusion. “I thought it was supposed to be easier with me on my knees?”
“That’s what the lady in the video said,” Tulip admitted, “But lady in the video don’t know us, so let me handle this.”
There was no protest to that as Jesse laid down on his back, already more relaxed just by virtue of not trying to hold a particular position, and the solid weight of Tulip climbing into his lap helped, too. He smiled as he settled his hands on her hips, his thumbs running over the straps of the harness as well as her skin before he slid his hands up her sides.
Tulip leaned into Jesse’s touch, making a pleased noise at his rough hands against her, and rolled her hips, just enough to tease but nothing more, before leaning in to kiss him.
The kiss was eagerly returned, Jesse claiming Tulip’s mouth as she claimed his, and his hips rolled upwards, seeking more than a tease. He paused after a moment though, after a few failed attempts at breaking the kiss and not immediately resuming it, muttering “Tulip? It’s poking me,” before their lips rejoined.
A giggle echoed against Jesse’s lips before Tulip broke the kiss again. “Now you know how I feel,” she teased, kissing him again before he could respond. She rolled her hips again, letting the dildo shift so it was at least pressing against a different spot, as well as teasing him a bit more.
Eventually, the kisses stopped, but Jesse couldn’t complain, even as Tulip climbed off him, settling between his legs so she could push his shirt up and off in order to leave small bite marks in the skin of his chest and then stomach. He desperately wanted her to turn her attentions to the underwear he was still wearing, tented with keen interest, and his half hard length longing for the pressure and friction of the earlier teasing to return. He knew better than to try to rush things though, especially when Tulip was on top, so he just balled the sheets in his fists and tried not to squirm too much.
Tulip took note of Jesse’s tells and didn’t tease for too much longer before pulling back enough to remove Jesse’s underwear, tossing it aside and taking the moment to grab the condoms and lube she’d set on the bedside stand and move them closer to her, distracting Jesse with a proper kiss as she did. It didn’t last long before she decided a better better place for her lips would be along the side of Jesse’s shaft, sucking lightly between licks to bring him to full hardness. Once he was ready, she pulled away again, just enough to look at him. “Gonna do the finger thing, then we’ll go from there. Okay?” she murmured, running her hand along his outer thigh.
Jesse whined when Tulip’s mouth was occupied with speaking and not his dick, but he nodded eagerly. “Yeah. Do that. Please.”
Smirking at Jesse’s eagerness, Tulip gripped him and took just the head of his cock into her mouth, sucking lightly as her hand slid from his outer thigh to between his legs and back until she could just tease at his entrance with one dry finger.
They had done this before dozens of times, and even with thoughts of what they had planned for the night, Tulip’s finger rubbing rhythmically around the rim of his entrance and teasing pressure at his perineum only made him groan and his cock twitch. He was torn between twitching back against her finger and forward into her mouth, until her hand was gone momentarily and he pushed back in search of the sensation again.
Tulip took Jesse further into her mouth as her hands were busied with the lube, slicking up her fingers and trying not to make a mess of things before returning her finger to Jesse’s ass.
The slickness surprised Jesse a bit, but as Tulip’s finger slid into him far more easily than it ever had before, he decided it wasn’t a bad thing. He moaned again, pushing back against Tulip’s finger needily and lightly clenching around it.
After a few moments of letting Jesse enjoy the finger as usual, she began to tease with a second finger, using her other hand to press at his hip to help keep him from bucking too much as she took more of him into her mouth, teasing at the head with her tongue.
Adding a second finger was new, but Jesse couldn’t say he didn’t like it, not that he was saying much of anything at the moment besides occasional moans and pleased groans among his heavy breathing. Then, Tulip started to push the second finger in and he wasn’t sure how to react. It didn’t hurt, and he didn’t make any move to stop her, but it didn’t feel as natural and easy as just one finger did. Once she’d managed to push it in fully, it was enjoyable enough, and he gave Tulip an encouraging nod as she glanced up to his face after he let out a huffed “fuck,” under his breath.
She didn’t want to rush things after the second finger, but it didn’t seem like Jesse had any inclination to stop, either, so Tulip just kept the two fingers inside him, letting him buck back against them at his own pace, for long enough that her jaw started to twinge with the beginnings of being tired. Soon Jesse would start getting too close to the edge, and she didn’t plan to finish him off like this, not tonight, so she finally started to spread her fingers inside him, working him open with intention of slipping a third finger into him.
Jesse was a bit surprised at the new movement, but the slow stretching was pleasurable and by the time Tulip did slide in the third finger, he was at the point of wanting more.
Tulip didn’t spend too long with three fingers in Jesse, he already pushing back against them actively almost as soon as the third finger’s length was fully inside him. She pulled her fingers out all at once and pulled off his dick, giving him one last lick before looking up at him. “Wanna get on your hands and knees now?”
The sudden emptiness and the air of the room hitting him made Jesse gasp, and it took him a moment to realize what Tulip had asked, but once he did, he nodded eagerly. “Yeah. God yeah.” He let her move so he could turn over again, pushing himself back up to his hands and knees, much more relaxed than the first attempt at the position. He did yelp at the repeat of Tulip’s playful smack, but he was grinning as he looked back at her expectantly.
While Jesse got himself into position, Tulip took the condom and rolled it onto the dildo, not wanting to have to bother with extensive clean-up after, then liberally lubed it up. “Ready?” she asked, running her clean hand over Jesse’s ass as the other gripped the artificial length to steady it as she nudged the head against Jesse’s entrance.
“Fuck me, Tulip,” Jesse said, the words surprising even himself as they came out, but he quickly distracted himself by rocking back, attempting to push the strap-on into himself.
Usually, Tulip would have attempted to tease a little bit, having not quite started yet and Jesse being so eager, but this was their first time trying this and she was willing to indulge him fully. She let the tip slip in with relative ease and slowly but steadily pushed in until her hips met Jesse’s ass.
The sensation was different than Tulip’s fingers. Smooth and a different firmness, but Jesse felt pleasantly full with the strap-on inside him and comfortably stretched around it, realizing the hadn’t a need to be nervous at all about the whole thing.
It was Tulip’s turn to be nervous then, though, having bottomed out in Jesse and realizing she needed to start moving. The harness had a pocket for a bullet vibe, but Tulip hadn’t put one in tonight, this was mostly for Jesse, and it was her first time, too. After what felt like too long being still, she opted to just back most of the way out and slide back in steadily, though a little faster than her initial entrance, repeating the action several times before asking, “Is this alright?”
“Yeah,” Jesse assured, having picked up on Tulip’s nerves, “It’s alright. Little faster maybe.”
“Faster, okay,” Tulip nodded, starting to push into Jesse a bit faster. After a few moments, she remembered a portion of the instructional video and changed the angle she was pushing in at.
“What are you doing?” Jesse asked, having been enjoying the previous motions notably more than what Tulip had switched to.
“Fucking you, what do you think I’m doing?” she asked in light offense, though she paused in her thrusting.
Jesse huffed with little amusement. “No, with the whatever you’re doing. Go back to what you were doing before.”
Tulip huffed in frustration. “I’m trying to hit your prostate.”
“Well you’re not managing it,” he grumbled.
“I can keep trying,” Tulip insisted, testing with a few thrusts at a different angle, then another, then another, hoping to get a positive reaction out of Jesse.
Jesse let Tulip make several attempts until just the wrong angle made him hiss lightly. “Ow. Just… don’t worry about that tonight. We can do that some other time. Go back to what you were doing in the first place and just give me a reach around.”
Tulip stopped immediately when Jesse hissed, though there was a hopeful look on her face that fell to a pout when it turned out to not have been a positive reaction. “Okay. Some other time, I guess,” she said a little flatly, but she readjusted to her original angle, working herself back up to her previous speed as she slid her hand around to grip Jesse’s length and start stroking him.
With Tulip’s hand around him and the dildo inside him, Jesse began to feel the pleasure pooling at the base of his spine and he began to encourage a faster, slightly rougher pace but pushing himself back and bucking forward into Tulip’s hand. It was less time than Jesse might’ve wanted to admit before he tensed and came, spurting onto the sheets and moaning Tulip’s name.
Once Jesse was obviously enjoying himself, Tulip pulled herself out of her disappointment and started to get something out of it, too, even if she wished she could get more than the misplaced pressure she was getting now. Jesse liked this and there would be other times. She stroked him through his orgasm before letting him go and pulling out slowly to let him lay down and settle into bed as she undid some buckles and took the strap on off so she could cuddle up to his side.
Jesse could hardly keep his eyes open after his orgasm, but he wrapped an arm around Tulip as soon as she was near, and his other hand made its way to her thigh. “That was good. Real good. Want me to…?”
Tulip couldn’t help but laugh at Jesse’s offer, seeing how he was ready to fall asleep at any second. “Not with you so worn out,” she said, smirking just softly, “It’s my turn next, but I want you to have a chance to give as good as you get.”
If Jesse had actually heard anything Tulip had said, he would have replied with a very interested assurance that he could, but his answer instead was only a light snore as he’d already drifted off to a satiated sleep.