Barely Paralegal Ch. 05

"Oh I almost forgot." Linda says as she reaches into the first shoebox that had the Velcro straps. "This test is going to be blind." And then she pulls out a long piece of cloth that apparently is meant to blindfold me.

"Why do I need to be blindfolded???" I ask, and the first thought that crosses my mind is how I don't trust Linda and how maybe this is all part of a plan for her to pull some sort of bait and switch and end up using an even bigger dildo on me, without me knowing. That's how fucked up my head is right now.

With my hands still bounded to the back bed posts, Linda casually makes her way over to me and ties the blindfold around my face. It's a pretty big piece of cloth so it easily covers both my eyes and nose. "I want you to be able to focus on the feeling inside your ass, and this will remove any potential distractions that might get in the way of that." She says as she finishes tying one tight knot in the back, and I officially can't see anything.

So here I am, naked, blindfolded, and my arms are tied to the bed. Despite my overwhelming unease around the situation, I can't help but feel turned on, but part of that could be the extreme buildup of needing to cum though. As I sit and wait for what comes next, I hear a subtle squirting sound, followed by the touch of her hand on my thigh. She gives my legs a gentle suggestion to spread themselves open, and then I feel the cold sensation of her other hand applying a first dollop of lube right onto my butthole. Fuck. I was at least hoping for a quick rimjob before the penetration began, but I'm guessing that's not in the cards.

Linda starts feeling around my hole to make sure there's a solid covering of lubricant all over, and I brace for what I'm guessing will be a test plunge by one of her fingers inside me. Unlike yesterday when she completely surprised me with her finger in my ass, this time I'm mentally prepared for it. But it never comes.

Instead, I hear her dispensing even more lube, and as I lay here with my arms halfway locked to the bed, I can only assume she's now lubing up that black, bulbous, sex toy of hers. A few seconds pass, and then she finally speaks. "Up you go!" She says as she tilts my lower body back and lifts my legs up in the air. "Ok, I need your help here. I need you to hold your legs for me."

My hands don't have much free motion, but they have enough to be able to reach a little bit in front of me. With my ass now in the air, Linda pushes my knees apart, spreading my legs pretty wide open. This gets my knees close enough to my hands where I can actually grab the inside of them, despite being bound to the bed. Amazingly, it's not that uncomfortable, but holy shit does this position completely spread my butt open. I can't see it, but I can feel how totally exposed and defenseless my asshole is right now, as it's pointing straight up into the air.

And if spreading my own butthole wide open isn't humiliating enough on its own, Linda then adds an element of pressure to this position. She tells me, "Now don't let go of your legs here, no matter what happens." Yeah, that's easier said than done. She then continues, "Because if you do lose your grip, there will be a punishment." Fuck. I'm thinking I absolutely do not want to find out what this punishment is, so I reaffirm my grip and start holding on for dear life.

But there's something weird going on in my head right now. Here I am, being forced basically against my will to hold my ass open for this middle-aged woman to defile me for her own personal pleasure. By any reasonable definition, I am about to be raped. I feel confident that I don't want this to happen, but at the same time, if Linda were to cease this whole arrangement right this second and let me go, I am pretty sure that deep down I would be disappointed. What the fuck is wrong with me???

Why do I want this to happen? Do I actually want to feel this prostate massager shoved into my ass? Is it pure curiosity rather than potential pleasure? Is it my extreme horniness and needing to cum so badly that I'm willing to go to any lengths here, no matter how intimidating they are? Or is it less about the dildo and my response and more about just wanting to please Linda? Do I want to see her approval and satisfaction so badly that I'm willing to sacrifice my own severe discomfort? I've heard the term 'Stockholm Syndrome' before, and is THAT what's going on here? Has my brain already been warped this severely in the handful of days that have passed since my working situation turned so sexual?

As I'm trying to contemplate all of this while keeping my legs firmly held, I'm snapped back into the reality of the moment as I feel the first touch of Linda's dildo at the doorstep of my ass. At first, she just lightly makes contact with what I assume is the tip of it right on my button. And then she slowly slides it up and down my taint, and I can feel that if nothing else, she's applied a very generous amount of lube, because it's very slippery.

"Ok, I'm going to start with the tip. Just this first section here." She tells me. I take a deep breath as I feel my heart race with both anticipation and fear. I'll give Linda credit in that just like she said, being blindfolded is clearly adding to my physical awareness of what's going on down there. I then feel her apply a fair amount of pressure and the next thing I know, there's a strong burning sensation right in my ass. It doesn't feel like she stuck it in me, it feels like my asshole is simply on fire.

"Ow, fuck!" I sort of yell. "What did you do?"

"The first section is in." She tells me. "The hardest part is over."

"What? It's already in???" I respond, quite confused.

"Yep!" She cheerfully responds as if this is all just lighthearted fun. "But only about an inch or so."

"Here. See." Linda then says as she removes the dildo from my butthole. "Now it's out." And once she does that, the burning sensation is gone. But fuck that was intense. But before I can gather my wits about what just happened, I feel her give both my taint and my ass crack another slide with the dildo to lube it up even more, and then she pops it right back in. It's still intense the second time going in, but this time it's not as painful. The burning feeling has been replaced with more of a noticeable awareness that there is clearly something inside me.

"Now I just want you to hold onto your legs but try to relax." Linda instructs me. I decide to do as I'm told, so I recommit to my grip on the insides of my knees, and then I take an audible inhale and exhale deeply. While I do this, I feel Linda give the sex toy a much more significant push and I can feel it move deeper inside me.

I make a slight but audible grunt, before weakly asking, "Did you push the next section in?" As I say this, the burning sensation has come back and I also am very aware that there's something inside me. It's basically the worst aspects of both now.

"I pushed the whole thing in!" Linda then proudly declares. "How does it feel?"

This gives me a moment of panic as there's now a six-inch phallic object shoved all the way in my ass, but it also gives me some perspective as it doesn't feel nearly as big as I thought it would. I don't know how to describe the feeling, so I simply respond to Linda with, "It hurts."

"Ok, here." Linda says as she again removes the dildo completely from me, which initially is quite a shocking feeling of evacuation, but then soon gives me some reprieve. Then she tells me, "Each time will get easier and easier." And it's clear my break is quickly over as she proceeds to penetrate me again, but this time with just the tip. Then she takes it back out, and then slides it back in, but further. Over and over she does this, with each time seemingly being sent to a different depth in my rectum. Sometimes deep, sometimes less.

It certainly doesn't feel great getting ass fucked with this toy, but I do begin to get used to it, at least slightly maybe? Even though I'm blindfolded, I still instinctively have my eyes closed, and with the cloth also covering my nose I find I have to open my mouth to breathe. And boy am I breathing heavily right now. My main goal is just to get through this while making sure not to let go of my legs.

In and out, over and over, I feel the dildo go. "Oh my god... your ass is taking this pounding like a champ." Linda gushes, and hearing her compliment me like this gives me the first feeling of sexual satisfaction during this otherwise uncomfortable experience.

My mind is thinking about all sorts of things while Linda sodomizes my ass. I'm thinking about how I've only fucked someone once in my life, Linda last Friday, and now sadly I've been fucked myself as many times as that. I'm thinking about how little I knew about sex, and I had no idea women would ever want to do this to men, because I always assumed it was something only gay men did to each other. I'm worried about what this is going to physically do to me. Is it going to make my asshole loose? Am I going to have trouble going to the bathroom later? I have no fucking idea, but I sure hope it's not doing any lasting damage to my body.

After a full minute or two of Linda actively penetrating me over and over, I feel her remove the toy completely from me. "Keep holding your legs like that. You're doing great." She tells me. For a moment I think I might be all done with this part of her test, but then I hear her dispense some more lube on the object, and I realize I most certainly am not. Fuck.

And then yet another fear crosses my mind. What if this is where Linda tries switching out to an even bigger toy because I'm blindfolded? I just know she's planning on doing that. Fuck, I don't think I'm going to be able to handle anything bigger, but I can't see anything and I'm stuck holding my legs here, unable to move in any way.

Whatever dildo she's using now comes knocking at my asshole's door again and immediately just forces itself in. Although, it only takes a second for me to realize she definitely didn't switch to a bigger dildo, because it slides in so easily this time. In fact, it seems to go in so smoothly that for a split second I contemplate whether she actually switched to a SMALLER toy, before I realize by its size and feeling that it's definitely the same black prostate massager she's been using all along. I'm guessing it's just a combination of the extra lubrication with how much she's already loosened me up, that's causing it to seem like no big deal now. Fuck, that's really scary to think about. I can't believer she's made my asshole that much looser already.

But even with the effortless entry, once it's all the way in I feel like I'm definitely at maximum fullness. And even though it's already so deep, I feel Linda press just a little bit harder, and she clearly hits something inside of me that I've never felt before. It's almost as if she's hitting the bottom of my stomach, and for some godforsaken reason this spot has a bunch of nerve endings, and it's tickling my entire body.

"You feel that?" Linda asks me, as if she can read my mind.

I do, but for some unknown reason I play ignorant. "Feel what?" I respond.

Then I feel her apply even more pressure to the toy, and wherever that spot is, she nails it even harder. Another shockwave gets sent through my body and it's honestly probably half-pleasure, half-weirdness.

"That." Linda says. And then she explains, "That's your prostate. I can tell by the expression on your face I'm hitting it. Your cock is giving it away too."

Being blindfolded and unable to reach my penis, I wasn't even aware of the state of my own cock, and whether it had stayed hard this whole time or gone limp. But now that she mentions it I realize that I am in fact still rock hard. And that becomes even more apparent when for first time since this ass fucking began, I feel her hand take ahold of my penis.

More than anything, it reminds me how badly I NEED to cum. Fuck, it feels so good and yet not enough, all at the same time. But as she slowly starts jerking me up and down, I can't help but get a little optimistic that she's finally going to let me blow my load. It feels so fucking good. It's so good in fact, that I actually start to enjoy the feeling of this toy inside my ass. It wasn't obvious that I would get to this point, as my experience with this dildo has gone from painful, to uncomfortable, to weird, to neutral, and now I have to admit, pleasure.

Linda continues to hold the toy both firmly against and up my ass, and it's putting a nice constant pressure on that spot she claims is my prostate. At this point, I don't care what that spot is, as all I care is that it feels like magic. And then oh my fucking god, completely out of the blue, I'm jolted by one of the biggest surprises of my life.

She turns the vibrator on! This whole time, I've been so fixated and overwhelmed with Linda repeatedly inserting this object into me, that I had completely forgotten the toy also vibrates! This new sensation on top of everything else, catches me so off guard that I simply exhale and grunt into one loud "Uggggggghhh." The vibrations are coursing through my entire body, and now Linda starts jerking me even harder, and there is no doubt I'm going to cum. I've never been more sure of an orgasm in my life.

I start to make new, uncontrollable noises, and Linda picks up on this and tells me, "It's so hot hearing you moan like that." Of course, this only turns me on even more, leading me to become even louder.

In between my moany grunts, I find myself taking huge deep breaths through my mouth, because I still can't breathe that well with the blindfold over my nose. I reaffirm my grip on the insides of my knees, because that's literally the only thing I have control over right now. But as I desperately hold onto my legs, I can feel the vibrations from the toy all the way to my fingers. My ass is pointed straight up in the air, and Linda has one hand furiously jerking my cock while the other holds the vibrating dildo as far up my rectum as it could possibly go.

I continue to gasp for air and exhale in moans all at the same time, and then finally, after this huge sexual buildup over multiple days, I start releasing my cum in what will undoubtedly be the most intense orgasm of my life. It feels so unbelievably good that I don't even care that my first shot of jizz hits me right in the chin. I can't see it, but I can feel it. My second spasm feels even better and stronger than the first, and this shot of semen flies right into my wide-open mouth. I obviously know instantly because I can both feel it, and taste it. Eating my own cum is far from desirable, but I barely even care. I manage to close my mouth though, and as the third, fourth, and fifth loads of cum come flying out, they hit me in different places around my mouth and chin, and I hear Linda giggling as she watches my face take this barrage of friendly fire. Although, then it dawns on me. She's the one holding my cock, so I'm sure she's the one controlling the aim, and I have to imagine she's aiming at my mouth on purpose.

But fuck, this orgasm is so good I almost don't even care. I finish spewing every last drop of semen I could possibly have, and then Linda releases my cock and pulls my hands off my legs, so they can finally relax and fall to the bed. At the same time, she slides the black toy that both violated and pleasured me like nothing else before, gently out of my asshole and then turns it off.

She lifts my blindfold up to my forehead, and asks, "How was THAT?" while she immediately starts taking the straps off my wrists and releasing my arms so they too can relax.

The euphoria from my orgasm and the feeling of being free from my restraints is more than enough to overcome all the other discomfort of what just happened, so I simply answer, "Good."

As I continue to get my bearings with my eyes now open, I realize what a mess I am, both physically and mentally. My asshole feels totally used and slimy and I have multiple streaks of cum all over my face, not to mention the taste of semen from the squirt that landed inside my mouth. And on top of all that, I'm trying to process everything that just happened. Linda seems to notice that I could use some help, so she heads to the bathroom and brings me a large hand towel for me to clean up with.

I wipe my face and chest off before using it to give my ass a solid wiping as well. The towel is light gray in color, but after giving my butthole a good once over, I can see some remnants of beige and tan that I'm sure are the result of all that anal probing. That's kind of gross, but I try not to react. Linda takes the towel, and I'm sure she can see the hint of brown as well but doesn't bat an eye. I can only assume that's a normal occurrence with any kind of butt sex?

"So I thought you did pretty well for your first test." Linda tells me. I'm not sure I'm a big fan of her using the word 'first' here, but I guess it's not that surprising the more I get to know her. Then she tells me, "I think I'd give you a B right now."

I really don't care what kind of made up grade she gives me, I'm just glad this test is over and I finally got to cum.

Then Linda continues, "But you do have one more chance to bump that up to an A, if you're up for doing a little extra credit."

Fuck, I hope this extra credit really is optional because I'm 90% sure I'm not going to be interested. I don't say anything as I'm just waiting to hear what earning this meaningless A will entail.

Linda then holds the toy in front of me and tells me, "If you're willing to suck and lick this guy clean, I'll bump you up to an A!"

Change that 90% to 100%. No fucking thank you. After seeing what that hand towel ended up like, thinking about putting that dildo in my mouth is so fucking foul. What in the world would make her think I might want to do this? Like how gross does she think I am? Or more accurately, how little self-respect does she think I have?

I figure I don't want to be too confrontational here, so I answer her politely, "I think I'm happy with my B if that's ok."

"Of course." She answers, and I'm thinking thank god it really was optional. But still, fuck that's gross. Then Linda mentions, "Good work holding onto your legs the whole time, I'm sure that wasn't easy."

Yeah, it wasn't easy. It was actually quite taxing and my arms and hands are tired as shit right now. Then I remember how she had told me there would be some sort of punishment if I ever lost my grip. I'm glad that never happened, and then it dawns on me. Is there a reason she just mentioned this right after I turned down her gross offer to suck that dildo clean? Oh my fucking god. Those two things are probably related. I think that's it. I think THAT was going to be my penalty if I had let go of my legs. She was going to take the dildo out of my ass and make me suck it, blindfold and all.

Oh my fucking god, every single time Linda and I do something sexual, part of me leaves happy and satisfied, and the other part of me is so freaked out. I'm trying to process everything that just happened, both the good things and the bad, and I feel completely lost and overwhelmed.

"Why don't you get dressed and head down to Mark." Linda then says, and with everything going through my mind right now, I'm thinking that sounds like a good idea.

It's around 9:30am, and I make my way down to the basement, now fully clothed yet still quite in shock from the events of the morning.

Mark greets me, "Hey, how's it going?"

"I'm ok." I respond as I have a seat at my desk.

"You and Linda all done?" He asks.

"Yeah." I say.

"What'd you guys do?" He then inquires quite curiously.

I honestly have no desire to discuss this, even with Mark, who I probably feel more comfortable talking about stuff like this than anyone I've ever known, so I politely tell him, "I'm really not in the mood to talk about it, if that's ok."