Awkward First Time [Halloween Special 2023.]

“Well,” you examine her petite body and ample chest. You swallow hard on the lump that’s formed in the base of your throat. You weren’t complaining about being placed in situations like this, but you still felt a little awkward nonetheless. When you look at Delila’s face, you’re surprised to see them recognize the face– Delilah, with an H at the end, had an expression similar to her first time with you. “I suppose I should be on top?”

Delila nods. “Yes. I don’t know what I’m doing,” she tries to laugh, but it falters as the attempt leaves her lips.

It was no secret that you were getting excited at the aspect of being with Delila; you could have 0nly hoped for better circumstances. The whole “backroom” experience still left you a little unhinged. Still, it became easier to forget once you started to rub your hands against Delila’s exposed thighs and bare arms. Her tattoos stretched at your passes while your breathing increased in unison. A small whimper came from her mouth before she started to blink rapidly. “Are you supposed to get me this worked up?”

You smile at her, leaning in to kiss her. She took your kiss happily and twirled her tongue around yours, counting your teeth as she carefully grabbed your waist. She held onto you while you started to kick off your pants. The kiss breaks when you want it to. “I think it’s better when she’s worked up for me.”

Delila's crooked, cute smile is beneath a harsh pink from her blush. “You’re a playboy at home, aren’t you?”

You sit back and lift her into your lap, where you resume kissing. Both pairs of hands are busy exploring the body of her partners as the smacking of lips and tongue starts to join the lewd tunes playing from the speakers.

“I’m a contractor,” you breathe near her while you grab a handful of her ample rack. “But, I find pleasure where I can.”

Delila’s breath hitches at the top of her throat and is released throaty. Immediately, the bridge of her nose turns rosy red. Her eyes dance over yours, seeing your face as it burns differently in front of her. She leans back and you lay her back down. “Then, feel free to show me what you’ve learned.”

As the words left her mouth, she swallowed hard, and her eyes doubled in size. She glanced down where the bulge on your underwear throbs in anticipation. She runs her saliva over her bottom lip with her tongue.

“You want me to be gentle with you?”

She doesn’t respond to your question. She’s fixated on your penis. She blinks and then looks up at you. “Wh-what?”

“How do you want me?”

“However you want to be, I suppose.”

You glance at her body– she’s ripe for ravishing. She’s your first, but you feel no pressure to be careful with her. Instead, you want to use her body like a toy, a tool for your relief after all the stress. Somehow, it seems fitting that she’d share the name of your original love interest.

After brushing back her hair, you lean in and kiss her neck. Underneath, she writhes in pleasure. You can feel her back arch towards you as a cute bleep of noise emerges. “Those are dangerous words,” you remark, pulling only slightly away from Delila.

She squirms. “But, this isn’t the most dangerous position I’ve been in,” she giggles slightly but then moans as she feels your hand against her breast; most of all, however, she can feel your slick tongue drag along her collarbone.

You can’t tease yourself any longer. You finally reach between your legs and pull down on your underwear. Upon taking out your member, you give yourself a few self-applying strokes to stimulate your nerves of primal entertainment.

Delila can’t see what you’re doing, but she can feel your fingers training around her honeypot as you pull her panties aside. You can hear her gasp and feel her legs close slightly; feeling her hesitation, you hold back. “Are you ready?”

“I feel funny,” she admits sheepishly. “My heart feels like it’s about to burst out of my chest.”

With your hand still placed firmly on her boob, you then notice how fast her heart is racing. You lean in and kiss her again, moving her hand slowly between her thighs and chest– coaxing her into the mood. Despite your best efforts, she still feels a little awkward, so you continue petting her until she’s loosened up. A few minutes pass with her moaning before you get tired of getting her more relaxed, however.

“Tease me more,” she pleads. “I- I’m not ready yet–!?!”

You drive your middle and ring finger into her snatch, effectively cutting off her ability to break for a full second. She gasps while squeezing your sides. Her mind spins to cope with the sensation of being plugged for the first time. “Haah~ haaha~!! Oh! Ay, Dios mio!”

Delila doesn’t try to get away or push you off. Instead, what she proceeds to do, is hump your hand while mumbling heated Spanish. You start thrashing her pussy with your fingers. Watching her body become electrified with ecstasy. Her pupils widen while her mouth circles in a large “O.”

She’s gone stiff but has become more brave in exploring her limits. She nods while her eyes stream with tears. “Enough of that~!!” She grabs your wrists and tries to **** you back. She isn’t strong enough, but you withdraw yourself anyway. You sit back down and spread your legs, asking her if she needs a moment. She spots your cock and licks her hand. “It’s time I get you ready for entry, don’t you think?”

You only have to nod for her to get into position. She coils to her knees and grabs your erection. Your dick waves for attention, and when she wraps her digits around you, you fight the urge to shiver. She doesn’t need to be told how to treat you. She gradually spits, fondles, and adjusts her grip. You watch her expression shift. Her mouth moves, and her eyes fixate. When she looks up at you, she grins. “You like this?”

“You’re a natural,” you sigh.

“Don’t say that too loudly,” she coos at you, spitting again. This extra application of saliva makes another noise to join the music above. A wet, slimy noise emits from your cock and her hand. Her other hand massages your package, tugging it slightly and squeezing it with motherly care. “I like to think I’d only do this for you.”

You watch her handiwork on you. She’s either had practice or had seen enough of her colleagues do this before that she confidently gives you a handjob that isn’t lazy or undesired. She spits more, and every time she does it, she brings her mouth closer to the tip of your erection, teasing you with the thought of what she’d look like with her mouth full of your man-cock.

Eventually, she uses both of her hands, and she expertly pumps your shaft from the base and then all the way to the tip. Her alternatives were straight motions, twists, slow and fast– it keeps you focused, and most of all, rock hard. “Fuck, Delila…”

She peers up; her grin is devilish despite the hint of nervousness still plaguing her brown eyes. “I love the sound this is making.”

You’re both silent as the wet sounds of her handjob fills the room. Your breaths start to get harder, and Delila starts to giggle to herself. You aren’t sure how much time elapses, but all you know is that you’re ready for more than just what she’s providing currently, and you make this clear by announcing it.

Delila smiles at you crookedly, nodding slowly. “Are you close?”

“I’m rock-fucking-solid,” you chuckle. “I want to fuck you so badly right now.”

“Oh,” she blinks, her handjob slowing down. “Your cock is covered in my spit.”

“Ready for exploration,” you try to little the mood, and a genuine giggle greets your attempt.

“I’m ready for you,” she says. “I’m so wet right now anyway. I doubt you’ll need much time to get– you know... inside me.”

You take Delila’s hand, and she gets on her knees. You don’t move, but she straddles you. You can feel the tension in her body as you place a hand on her hip. “This part,” she has an excited quiver in her face. “It’s making my head spin.”

“I’m excited too,” you explain, letting your eyes linger on her lewdly covered tits. “You’re beautiful, you know?”

“I know,” she grins at you. “And you’re stupid-handsome.”

Delila closes her eyes and leans in. You do the same and meet her lips in the middle. There’s a lot of emotion that shoots through your system when your lips connect. The drag of your tongues and the squeeze of your hands. She lowers herself, and you carefully guide yourself between her puffy lips.

The tightness of a virgin is what you suspected from her. As you felt the resistance of her womanhood slowly open up to you, you knew you were in for an expected treat. Your throat closes while you subtly push your hips forward. Delila breaks the kiss and glances down as you take her virginity away from her. “Oh, baby…”

“I-it feels– it hurts, but–??” Delila tries to maintain a clear head but cannot express her feelings as she feels her hymen splitting. Her breathing starts to become heavier, but she there’s hardly a pause between movements. “You f-feel so good.”

You try to cope with the tightness, but admittly, you let out a satisfied groan as your member is slipped into her unused vagina. “Delila~...”

“Warren~!!” She squeals. “Fuuuck!! Eso se siente tan bein.”

You don’t have to know what she’s saying to understand her expression. She wraps herself around you while dipping further down. She can’t manage going balls deep yet, but she starts riding you nonetheless.

Delila begins to ride slow at first, but within the boundaries of her own pace, she gradually increases the speed, going slightly further down your shaft at every braved inch. More of her native tongue slips out in praise, and before you know it, she is telling you to fuck her.

Knowing what you want is now within reach, you push Delila flat to her back and get into a missionary position. You grab her tiny waist and ravish her figure with your eyes for only a few seconds before pounding into her.

Delila screams at first, but after the third thrust, she’s moaning and digging her fingers tightly into the sheets of the heart bed. Her legs tighten around your waist as you buck into her. It’s easy to do between her honey and her salvia around your rock-hard member.

You are only barely able to keep yourself at bay as you ram-and-buck Delila’s never-before-used gash. Over and over, you slam into her hips and watch the sexual madness unfold with intensity. Even though you’ve left her bra on, her tits bounce every time you send your cock forward. An incoherent ramble of Spanish words is spat from Delila’s mouth– you guess there are a few curses in the roll of heated language that’s exchanged, but don’t dare draw your attention anywhere else away from her tunnel in a vain attempt to translate her spill.

Your cock is swallowed better than any of your previous mortal interactions. You notice the sweat marbling down your forehead as Delila continues her pitched moans and harsh screams. In the meantime, the action of your lovemaking would have been enough to fill the room. Still, with your grunting and her screaming, you have no doubt it’s invading the neighbor’s walls and traveling through the vents.

“Te deseo tanto!! Eres un amante incredible!!!” She could be cursing. She might be saying you’re nothing, but beneath the blush and tear-streaming eyes, you know she wants more of you. And then she tenses. “I- I’m cumming!!?”

When she announced her climax, you expected her to tighten. Instead, she spasmed and started to unleash her clear substance all over you. One of her eyes closes in her first-ever orgasm, but they soon roll back in bliss. Her mind shatters, and now all she knows is sex: sex and you.

“I’m about to cum,” you gasp. “You’re so fucking tight, Delila.”

“Pull out,” she stutters. “Don’t forget– to pull out!”

You don’t want to. But, you suppose there might be some untold **** that could fall on your lap if you get someone pregnant her. Nonetheless, you continue thrusting into her needy pussy until the last moment. You just loved stretching her a little too much. Every second, you had to appreciate it.

At the last moment, you pulled out and grabbed yourself, jerking yourself just in time to feel the jetstream of cum shoot out as your balls contract in pleasure.

You get off the bed, getting a better look at what you’ve done to Delila. You hadn’t known her for long, but somehow, this didn’t feel wrong. She covered her face with an arm over her face. “That was intense,” she said. “Shit.”