Stay On Target

As enticing as it sounds to slide inside Melody right now, you **** yourself to hold back. This isn't what you had agreed to earlier and although there was a very obvious sexual vibe going on between you, you didn't want to cross that line too quickly, especially not while you are both heavily buzzed. Ass play was one thing; entering your friend's most sacred place was another altogether. Also...

"That does sound wonderful." You say out loud and place your hands on the redhead's hips. She bites her bottom lip, obviously expecting you to penetrate her. Instead, she groans in disappointment as you push her pelvis back to her original position. "But you promised me your virginity. And I plan to have it."

"Damn it." She hisses sharply. She looks into your eyes with a pleading look of desperation. "I can't wait any more, Jack! I am going crazy! I need you in me right now!" You do your best to hold steady against her sexy ****, but it isn't easy.

"I have been waiting years for this opportunity, Melody." You tell her, admitting a little more than you intended. "I think you can wait a few more minutes."

"Y-years?" Melody asks in surprise, temporarily forgetting her intense lust. She then gives a whole body shudder as your lower your free hand between her legs and probe her wet sex, brushing against her clit as you do.

"Yeah, years." You nod. "So please let me do this right, okay?" She lets out a low sigh of both acknowledgement and enjoyment of your finger's movements.

"Okay. I...I guess I can hold out for a bit. Just please don't leave me hanging for too long, okay?"

"Don't worry, I don't plan to." You assure her as you pull your hand away from her pussy, your index finger and middle finger both coated in her sweet juices. "Lean forward for me, Melody." Your request comes out half as a question and half as a command. You are not sure at what point you gained the control of this encounter, but you are enjoying it. The usually headstrong and dominate girl in your lap was willingly submitting herself to you and the feeling of power was almost as intoxicating as the bourbon. Obediently, Melody leans forward, pressing your erection harder against her so the head was rubbing her sensitive nub and eliciting some gasps from between her quivering lips. As good as that felt, you had a more important objective. Her ass was now more prominently sticking out.

"Now what?" She asks you. You don't reply directly and instead answer with actions. You pull the hand that was holding her underwear aside out from being pinned between your bodies; at this point you are so close, the panties are not going to be able to move back in place and get in the way. With your now free hand you reach behind her and get a good handful of her plump ass cheek through the light cotton material. She lets out a surprised yelp.

"Now this." You reply and move your drenched hand down to her ass as well, sliding it in to her underwear past the elastic border. Your other hand helps pull her cheek in a way as to allow you better access to her puckered hole. You put your lubed index finger against her rear entryway and rub your fingertip around in a clockwise fashion. She grunts and groans at the new sensations while burying her face in your shoulder. "You have such a sexy ass." You compliment her. "Ever have anything in there before?"

"J-just a finger or two sometimes when I play with myself." She says shakily. The thought of Melody fingering her ass with one hand while rubbing her clit with the other invades your thoughts and reinforces your hard cock.

"Just fingers? Never your vibrator?" You prompt. The fact she owns a vibrator is no big secret; you were with her when she first bought it.

"I tried a couple times, but couldn't relax enough to get it in myself." She admits.

"Do you want me to take control and fuck your ass myself?" You ask with a grin, enjoying teasing her. You can see why she likes teasing you so much; it's a lot of fun when she doesn't have a snide remark or vulgar comeback.

"Y-yes." She whispers, then her voice takes on an annoyed tone. "Now will you please stop playing 20 questions and get to it already?"

"As you wish." You say as you push your finger forward. Her asshole does not give at first, be after a minute of steady pressure, it eventually relents as accepts your digit into her butt. She lets out another gasp and grunt and you can feel her clench down tightly on your finger. "Hey, hey. You have to ease up or you will crush my finger." You whisper softly.

"Sorry." She manages to eke out, her voice cracking. You take your free hand off her ass cheek and rub her back softly. This helps her calm down and she eventually loosens back up.

"Just take some deep breaths and I will go slow, okay?" You tell her. You feel her bite down on your shoulder in response; not enough to leave a mark, but enough to elicit a little bit of pain.

"I'm not some virginal prude." She says, obviously frustrated at her lack of power over her involuntary reactions. "You don't need to give me anal 101 lessons, you know. I was just...surprised."

"I know." You assure her. You don't want to spoil the mood now that you are this close. "Do you want to take the lead?" She is silent for a moment before responding.

"No." She whispers. "I want you to continue."

"Okay. Are you ready?"

"Yes."

"Good." You wait until you feel her warm breath exhale onto the nape of your neck before making another push to sink your finger into her tight ass further, this time up to the knuckle. She gasps again, but manages to stay relaxed this time. After a few more breaths, you go again, this time sliding your full finger inside her.

"Oh wow." She says between ragged breaths. "Is that..."

"Yeah, that's the full finger." You nod.

"It is so much more intense then when I do it to myself. It feels a lot bigger too."

"Well it's not the biggest thing you will feel up there, you know." You remind her.

"Yeah, I can tell how big it is right now." She responds into your shoulder with a little laugh and gyrates against your manhood as best as she can with your finger in her ass. "It is so rigid right now, it feels like there is a pole between my legs. A hot, throbbing pole." Her voice gets a sexy raspy tone to it as she lifts her head up for the first time in a while to put her lips by your ears. "You are really excited to fuck my ass, ain't ya?"

"Absolutely." You reply, trying to adopt a husky voice as well. "And you're not one to talk, considering I can feel you getting even wetter on my dick."

"Well, why don't you stop playing around and get down to OH GOD!" Her taunt is cut short as you begin to piston your finger in and out of her asshole. You probably should have gone a little slower so she could acclimate to it better, but you really wanted to knock her back down a peg and replace that smug smarmy attitude of hers with the sexual submissive she was earlier. Her gasps and moans were exactly what you were looking for. Her fingers grasp your shirt tightly as you finger fuck her. "Oh fuck fuck fuck!" She repeatedly swears.

"That's the idea." You reply and prepare to introduce the middle finger to the mix. You find it surprisingly easy to work the second finger in and stretch her tight hole further.

"Oh my God Oh my God." She gasps breathlessly at the sudden feeling of two fingers inside her. You smile to yourself as you work over her ass and properly prepare it for what is coming next.

"Are you doing okay?" You ask her after a few minutes have passed.

"Yes. It is starting to feel really good." She admits to you. After a bit of silence, save for the wet sound of your fingers sliding in and out of her, she speaks up again, a little weaker. "Jack?"

"Yeah?"

"I don't know if it means anything now or if it is too late at this point, but...I really wish I could have given you my virginity. You know, my actual virginity." You are so floored by her words that you almost stop moving your fingers altogether in shock.

"Y-you do?" You ask, unsure of how to respond.

"Yeah. My first time was nothing special; the guy, the timing, the place...nothing of it was meaningful to me."

"You never told me this." You reply, concerned.

"I didn't want to admit my first time was such a failure, that it was something I was going to forever regret." You hear her sniffle a bit as she spoke. "And just being here like this with you make me wish that...that it was you. If I could go back and do it again I would. In a heartbeat." You open your mouth to respond, but not words come out. What do you say to that?

"I...I'm sorry." You eventually manage to **** out. "I do too. My first time was very special to me, but I would trade it all away for a chance to give my virginity to you." Now it was her turn to be speechless and you carried on in silence for another couple minutes before she finally speaks again in a hushed tone.

"Jack...I think...I think I am ready for the real deal now." She lifts her head off your shoulder again and puts her lips by your ear. But this time, there was no exaggerated sexy voice or erotic wordplay. Just a few words whispered out in pure need. "Please take my last virginity and fuck me."