Barely Paralegal Ch. 04

Linda also doesn't say anything right away, but I can feel and hear her shuffling around on the bed. She's obviously getting herself into position, and soon enough I feel her two hands land right on my two raised ass cheeks. There's a slight but noticeable pull as she spreads my ass a little more open, and then I hear her softly say, "Yessssss... this is what I've been waiting for."

As apprehensive as I obviously am about this whole turn of events, I'd be lying if I ever claimed that Linda's joy doesn't affect me, because it clearly does. Hearing the pleasure that she's deriving and even taking from me, is such a weird dichotomy. Part of me genuinely fears that she is going to physically hurt me, or at the very least do something that makes me feel uncomfortable, but there's another part of me that feels so good that my body is giving her such pleasure. The positive feedback and compliments are becoming almost like a drug, in that I didn't even realize how good they've been making me feel until I've already become addicted to them. The bottom line is hearing Linda's joy always seems to give me satisfaction, even when it's coming at my own expense.

Next, I feel Linda's hands switch from simply holding my ass open, to slowly moving around as she caresses my butt and legs all over. "God, you're so hairless and smooth..." she gushes. "And this might be the most perfect asshole I've ever seen. I'm talking internet OR real life. Seriously, what an adorable, precious, virgin hole you've got here." She then leans around to direct her next comment directly at my buried face and says, "After 18 years, it's finally going to get the attention and appreciation it deserves."

As she continues to talk incessantly about my butthole, her hands start wondering over and around my cock and balls, and each gentle brush over my privates alleviates some of my anxiety with a physical sensation I'm much more comfortable with. Then she softly runs her fingers along my shaft and over my balls, but this time she keeps going and continues on a path that very slowly and deliberately passes over my taint. I can tell where she's going next, so I simply keep my face buried in the pillow and brace myself.

Her finger traverses my perineum and makes its way to the bottom of my asscrack, and then without stopping, it continues along until I can feel her fingernail unmistakably graze over my exposed asshole. The sensation of her touching me there feels like it triggers an alarm in my body, as my entire feeling of personal space has been compromised.

Last week when I was in a similar position, she had briefly touched me there as well, and I instinctively retreated my body away from her. But for whatever reason, maybe because this time I was actually expecting it, I'm able to hold my ground and not flinch at the moment of contact.

"There you go, darling." She tells me. And then as if she's purposefully testing to see how far she can push me, she decides not to keep her finger on a path up the rest of my ass crack, but instead she circles back and touches my butthole a second time. And then a third. She's just leaving it there and starts pressing it over and over again, like it's a button wired directly into my spinal cord where each time she pushes it, it sends a shock wave through my nervous system.

"It's so sticky to the touch." She then tells me. "Can you feel that?"

Of course I can feel her touching my asshole. I've never felt anything more apparent in my entire life. As to the part about it being sticky, I have no fucking idea. I still don't say a word, but I do turn my head so it's facing out from the pillow now, but I keep my eyes shut. It helps to be able to breathe freely, rather than trying to suck air through the pillow.

She must've noticed me poke my head out, because she then asks, "How're you holding up?"

I figure I should try and actually respond, so I say, "I'm ok." even though that's a pretty optimistic assessment of my own mental state.

"Good." She responds rather cheerfully. And then she continues, "So you're in for quite a treat today. And I'm saving the best for first." She says with a laugh.

And after she says that, she gives my legs and butt a fresh rub all over before reinitiating her firm grip on my ass with her two hands, spreading my cheeks wider than they've ever been spread before.

Then she tells me, "You're going to get to experience something that so many guys are DYING for their wives and girlfriends to do. But even though those girls aren't willing to, I am." And then she laughs. "I'm going to show you what it feels like to have your ass eaten. And I'm going to enjoy it every bit as much as you seemed to enjoy eating my pussy a few days ago."

My initial thought is, ok this isn't too bad. Things could definitely be worse. And to be honest, that last part she said about enjoying it like I enjoyed licking her pussy really hit home. Could that actually be true though? How could eating my butt possibly taste good? A pussy is one thing, but the only flavor my butt could have is shit, right?

Linda keeps explaining though, "I think there are two reasons why guys fantasize about having their assholes licked. The first is because it feels damn good. Now don't get me wrong, as I'm sure you'll see soon enough, it can feel kinda weird. Especially on its own. But once you get past the initial weirdness, you'll see how amazing having a warm, wet, tongue on your asshole can feel when you're also getting your cock played with."

God, sometimes I just don't know what to think. Linda has a way of making me feel one way one second, only to say something else and get me to instantly doubt what I was just thinking. The way she just described getting a rimjob kind of actually makes me want to try it now? I'll tell you one thing, I'm a lot more open to the idea of getting my butt licked than getting it penetrated. That's for sure.

But Linda wasn't done with her explanation. "Now, the second reason guys LOVE getting their ass eaten... is the psychological aspect. I mean... think about it. Your butthole is the most protected, hidden, sweaty, and dirtiest part of your entire body. For a girl to voluntarily accept that into her mouth, and explore it with her tongue, tasting everything it entails, is just about the most submissive act she could ever do to a man. That's why my husband always says there's nothing that makes him feel more like a king, than when I'm rimming him."

Now I have no choice but to admit, I'm both VERY curious and really turned on at this prospect. Hearing Linda describe just how foul an experience this theoretically should be for her, but to know that she still really wants to do it to me anyway, is kind of insane. And she's right. Licking someone's asshole is extremely gross when you think about it, and it's something a week ago I probably would've assumed I would never experience in my lifetime. And I still don't think I would ever ask someone to do this, but if she really wants to do this to me, then I think I kind of want her to?

I still don't say anything, by my newfound arousal gets me to breathe a little heavier. I feel my heart rate pick up, and for the first time today I get that good nervous feeling of anticipation, not the buzzkill anxiety I had initially been experiencing since the conversation turned to my butt.

"Ok, you ready?" Linda asks me.

I open my eyes, see her and give her a slight nod. This instantly makes her break out into a big grin. But then her face disappears behind the rest of my body as I'm sure she's assuming her position. I feel her hands tighten their grip on my ass, and then I start feeling some soft, gentle kisses on my cheeks. My heart is racing now in anticipation of what it's going to feel like. I feel her mouth jump back and forth between the two sides of my ass as she continues to give me one tiny peck after another. Each one seems to land a little closer to the center of my crack than the one before it. There's nothing for me to see with the way my head's positioned, so I close my eyes. My breathing gets more and more intense as my chest expands and contacts against the mattress. For a moment, the kisses seem to stop and now I can feel her warm breath directly on my asshole, as I'm sure her tongue must be only an inch away.

"I LOVE how fucking nervous you are." She says, and I can literally feel the words from her breathe on my exposed hole. She then tells me, "I can feel you trembling." as I'm honestly trying my best not to shake, but it's hopeless.

And just as the anticipation was about to drive me insane, Linda finally commits and presses her warm, wet, tongue on my asshole. As she does this, I hear and feel her let out an audible moan into my rear end. "Mmmmmmmmmm." She says, sending vibrations directly into my ass.

The feeling is so fucking weird. It's slimy, and invasive, yet not uncomfortable at all. To be honest, it's not as good as I was hoping it would feel. But I can definitely tolerate it, as it's way more weird than bad. But it seems like Linda is enjoying the experience more than I am, as I can hear her continue to make satisfied moaning noises, and an occasional muffled sentence like, "So good..."

But then everything changes. The next thing I feel is Linda's soft hand reach around and grab ahold of my cock that had been pointing straight down. Holy fuck, had I apparently been waiting for this, because a jolt of pure pleasure courses through my entire body. And then, her hand moves and starts rubbing the back of my balls, and that feels incredible too. And then it's back to my shaft. And then oh my god, it all makes sense. The licking of my asshole goes from being a weird novelty to being the ultimate compliment to the attention on my penis. The two sensations work so well to compliment each other, the joy in the combination is far greater than the sum of its parts. It's fucking mind blowing.

And just as I finally settle in to a split of 100% enjoyment and 0% apprehension, I feel Linda abruptly back away from both my asshole and my cock and say, "Time to flip over."

I slowly open my eyes and turn to look towards her, and I can immediately tell that it's neither a joke nor open for negotiation, so I guess I should comply. I lift myself up and peel myself off the pillow and sheets to the realization that I'm actually pretty sweaty right now. Fuck, that was intense, despite seeming so short, and now my attention is obviously shifting towards the question of what's next.

Linda had told me to flip over, so that's what I do. I rearrange myself until I'm in a sitting position on the bed with my legs facing where she's standing to the side. I take the initiative and scoot myself closer to the edge, and this leads Linda to smile. Then, without saying a word, she takes my two heels in her hands, lifts them up, and tilts me back so my asshole is once again completely exposed, albeit in a very different position than the one I was just in.

"I need your help here." She tells me, as she reaches for my arms and pulls them forward. "Hold your legs like this." As she forces my elbows to lock and pin my legs back, much like the position she was in last week when I was licking and fingering her.

"Like this?" I ask, as I think I have them pretty well held back.

"Perfect." Linda says. And then she adds, "Now where was I?" as she crouches down, buries her face below my junk, and starts tonging my butthole once again.

I was a little worried when she had me flip over that we were going to be all done with this step, so the sensation of her wet mouth once again on my asshole gives me a great sense of joy and relief, and I can't help but let out a soft, "Ahhhh... fuck yeah."

After a few more seconds of this, with my cock pointing straight up and not getting nearly as much attention as I wish it was, Linda pokes her head up and says, "Now I have a test for you."

"Ok?" I respond. "What is it?"

"I want you to hold your cock in your hand, while keeping your legs back, and I'm going to keep eating your ass." She tells me, and all I can think of is how amazing this sounds. "But... and it's a big BUT." She stresses. "I don't want you to cum."

Fuck. That sounds less amazing, especially given my blatant issues last Friday of cumming too soon.

Linda then repeats herself, "Don't cum."

"Ok, I'll try not to." I respond as Linda was on her way back down to my asshole. But my response stops her in her tracks.

She comes back up, looks at me sternly and says, "DON'T. CUM."

"Ok, ok.... I won't. I promise." I tell her.

And then as Linda finally assumes her position back down at my exposed asshole, she adds, "Just let me know if you need me to stop."

And with that she starts licking. I savor the feeling of just having her tongue on my asshole for a few seconds before finally reaching out and grabbing ahold of my dancing cock, making sure I still keep my legs pinned back. Holy shit is this an amazing feeling. It's so good that I have no choice but to be very conservative with the amount of stimulation I give myself. I'm sure that if I just started jerking, I'd be shooting sperm six feet into the air in no time. But I restrain myself, and I alternate between not touching my penis at all, and just holding it softly without any jerking motion. But even this limited amount of touching feels so good with Linda's tongue constantly running circles around my rim, that I know I won't be able to do this for very long.

After a minute or two of this incredible tease, I start to feel like I might be getting close to the forbidden orgasm. I touch my cock one more time, and that causes a sense of panic as I realize, fuck, I'm really close. So I immediately release myself and let Linda know, "You should probably stop."

She actually does as I ask and immediately removes her tongue. As she stands up, I'm pretty sure I'm in the clear and I've managed to avoid cumming right now, at least for the time being. My cock is kind of flailing around freely though, just dying for someone, anyone, to touch it and release the huge load of jizz that's been building up not just today, but all weekend long.

Linda is now standing naked in front of me, and I can immediate feel one of her hands down by my ass, while her other hand comes up right near my twitching cock. She comes so close to touching it, surrounding it with her curved hand even, but she doesn't make contact. I momentarily get super excited that she's about to jerk me off and release all my tension into the air, but this optimism quickly turns to impatience, as she continues to tease me by just hovering her hand around my penis, as if she's purposefully toying with me just to torture me.

As I stare down at my raging boner, wanting so bad to feel the touch that will make me cum, I'm rocked by a completely different sensation. One that comes totally out of the blue and without warning. I feel Linda's other hand hit me hard, almost lifting my lower body off the bed. For a split second, I'm so confused as to why she would've struck me like that, but then I realize there's something else entirely going on. I feel something extremely invasive and uncomfortable, and then it hits me, she just jammed one of her fingers inside my ass!

I was not expecting this at all, so I'm caught completely off guard and let out a pretty loud half-grunt, half-scream. Linda immediately tries to soothe and reassure me by calmly rubbing my stomach and saying "shhhhhhhh... it's gonna be ok."

But she doesn't let up with her hand or finger one bit, in fact she keeps it so firmly inside of me that I can feel her other knuckles pressing into the flesh of my ass. "It's ok. It's ok." She continues to tell me. "The hard part is already done."

I look up and stare into Linda's eyes, and she's not smiling right now, but rather has this motherly look of concern. I take some deep breaths and try to compose myself, and once I get over the emotional shock of what this means, I realize that the current feeling of Linda's finger pressed all the way inside of me doesn't feel THAT uncomfortable. It surprisingly doesn't even feel like much of anything. It's certainly not pleasant, and I can kind of tell she has something inside of me, but to be honest the most prevalent feeling of all is her hand pressing hard against the outside of my ass.

"You're gonna be ok." She reassures me yet again. And I finally start calming down enough to get a grip on the whole situation.

I'm even able to get a question out. "What did you just do?" I ask, even though I already know the answer. The better question would've been to ask why she did it.

"I stuck my middle finger in your asshole." Linda bluntly answers. And then she asks me, "How does it feel?"

A couple more deep breaths, and I let her know, "Not good."

Linda still appears sympathetic, and then she tells me, "Just relax, it's going to be ok. But I guarantee you the more relaxed you are, the better." And as she says this, she starts gently rubbing my abdomen, trying to get me to lean back and calm down. So I do, and I continue to get more and more at ease with the situation, and it feels like Linda lets up a little on how hard she's pressing her hand into me as well.

"There you go..." She soothingly tells me, and then as she's continuing to rub her hand around, she leaves my mid section and starts running her fingers through my pubes at the base of my cock. She does this for a second or two, and then she actually goes up the side of my shaft with her soft hand. Her touch is instant relief in every way. Holy fuck does it feel amazing and seemingly fixes everything right in that moment.

She continues to very lightly caress my cock, and I'm once again introduced to this new sensation that comes from the combined stimulation between my ass and penis. There's no doubt that Linda's finger inside me is a different feeling that when she was licking my asshole, but shockingly it also seems to work in harmony with the attention on my cock.

I feel the need to asses what's going on down below, so I reach down with my hand to feel exactly how she's positioned inside of me, and I confirm that yep, it's her middle finger on her right hand plunged all the way up my butt. I may not be able to see it, but I can certainly feel it. It's so fucking crazy that this is happening.

"Does it feel a little better now?" Linda asks.

"Yeah, it's a little better." I let her know, as she continues lightly touching my penis in such an amazing way.

"How about now?" Linda then weirdly asks, but I also realize something does feel different in the few seconds since the last time she asked. It almost feels like her finger inside of me is moving?

"What is that you're doing?" I ask, genuinely confused and curious.

"I'm wiggling my finger around inside you." Linda answers, and for the first time since jamming herself inside me without asking, she breaks out into a smile. "Can your feel that?"

I can. But it's so indescribable. It's subtle, but I can clearly feel there is something out of my control moving around inside of me, and it's unlike any sensation I've ever felt before in my life. And so I respond, "Yeah, it's really weird."

Linda then fully grabs ahold of my cock with her free hand, and a wave of joy washes over my body. I can tell she's continuing to move her finger around inside me, and overall the experience of that and her grip on my cock feels pretty good.

Then Linda says, "Ok, how does this feel?" And as she asks that, I feel her extract her finger from my ass, and it almost feels like I'm taking a shit. And as soon as I realize that she's done that, she's already sliding it back in. And then out. And then back in. She's clearly finger fucking me now, and I'm definitely not sure about this. My first instinct is I'm not a fan of the feeling at all. The only saving grace is that she's at least still holding onto my penis while she does this.