Someone to Watch Over Me

[lovesthepain72]

Already have a follow-up to this in the works. You'll be able to find it and others and fun captions over at https://lovesthepain.blogspot.com

Someone to Watch Over Me

"Let me get this straight, Victor. You want me to tie you up and just leave you there?"

That was Kat. We were old friends, probably best described as occasional fuck buddies. When we first met years ago I was immediately attracted to her. A shorter brunette with a very toned, fit and firm body. We tried dating, but for some reason it didn't work out. We enjoyed each other's company and the sex was sensational, but a real relationship just never worked for us. So now we're just friends, and when neither of us are seeing anyone else, we'll fool around from time to time. Because of this, she knows me pretty well. She knows all my kinks and fetishes, mostly how I like being tied up and teased. It was never really her thing, but she indulged me a few times.

It was the same with other girlfriends, they might try it and play along for me, but since they were never really into it, it just never truly satisfied me. That's when I found out about this sex toy for men. It's called the Venus 2000. Basically, it's a machine that sucks cock, but what really interested me were the speed settings. They boasted it could be used to tease and please, so I figured this could be my answer. It was pricey, but I thought what the hell? Once I got it, I experimented for a while but never found the perfect setting that would keep me turned on but not let me cum without manual intervention. Either it was too slow and not as exciting, or it would slowly ramp me up and I’d cum within 30-45 minutes. Either I’d hold out and it would just happen or I gave into my desires and turned up the speed. I really wanted to be forced to endure a multi-hour tease session and came up with a couple ideas. First, I managed to hack the device and add some programming to it. This allowed me to add pauses, change speeds, program however I want or even make it random. The results were perfect, it would get me close and tease the hell out of me, but I still couldn’t go longer than a half hour before giving in and speeding it up. I considered self-bondage, but that idea scared the hell out of me. What if something went wrong and I was stuck? Best case scenario someone finds me and I'm embarrassed as hell, worse case I die with a massive case of blue balls!

My second idea was to ask Kat to help. Since I was single I figured she'd be the perfect person to get me secured and check up on me from time to time to make sure I was okay. She'd recently broken up with someone and made it clear she didn’t want sex for now, but since she would only be babysitting me I didn't think she'd have a problem with it. Plus, I would stay there for as long as she wanted, so even the duration was out of my control.

As I'm explaining this she says, "If you just want to be teased we could do that. We've played that way before, I don’t mind stroking you for a bit."

Well that’s good to know, I thought. It surprised me based on what she was saying about no sex. Guess a simple hand job was different. "I know, but with this device it's constant and relentless. It will just stroke non-stop, keeping me on edge for as long as it's on. It won't get tired or bored or anything."

"Ok, so what am I supposed to do, just sit and watch? Not very exciting for me if you’re worried I’ll get bored."

"Well no, not if you don't want to. I just need someone to check on me once in a while to make sure I'm ok. And of course, to eventually let me go. But since I'll be tied up you can do whatever you want with me, as long as it doesn't interfere with the device."

"So if I want to go in the other room and watch a movie that's fine?"

"Sure."

"I'd probably have to gag you so you don't bother me."

"That's fine, honestly I'd prefer it. Just peek in on me from time to time."

She thought it over for a moment, "Okay, how long do you want to go for?"

I did a poor job of hiding my excitement by smiling wide, "I'll leave that up to you. I'd like to try around two hours, but as long as you're willing to stay."

"Well I'm supposed to meet up with a girlfriend for dinner and it’s already four o’clock, but I think I can make it work. Okay, fine, get out of your clothes and on the bed and show me how this toy of yours works."

I do everything she says, and before I know it I'm completely immobile with the Venus slowly working on my cock, occasionally pausing and starting, varying the speed and duration each time. I have it rigged to the ceiling so that my cock is pointing straight up in the air while it's being stroked and less likely to slip off. Kat's final touch is putting a gag in my mouth.

"Okay, you perv. I'm going to run out for a bit, I'll be right back." This concerns me as the whole point was to have someone here for my safety, so I start making as much noise as I can through the gag. "Oh relax, I'll be gone 20 minutes tops. Besides, you have plenty here to keep you busy." And just like that she's gone and I'm trapped. It doesn't take long for the device to start having an effect on me. Since I've done this before I know what to expect, but since this is the first time I’m truly helpless I’m much more excited than normal. After around 15 or 20 minutes I’m already wanting to cum, and would if I wasn’t tied up. Instead all I can do is get close, not quite on the edge, but like the edge of the edge, and that's where I stay and I know it won't stop until Kat allows it.

That's when I hear the front door and am relieved that she's back. It's a few minutes later when my bedroom door opens, and if it wasn't for the gag my jaw would have dropped. I guess she went home to change because she's wearing sexy lingerie and looking sensational. I can only moan in my gag. "Oh, do you like?" she asks innocently, twirling around to give me a show. "I didn't think I was properly dressed. Did you really think I was going to sit in the other room while you're like this? It's been over a half hour, from what you've told me you should really be feeling it by now, which means you'll be very obedient if you want me to let you go. So we're going to remove the gag and I'm going to sit on your face. Better try real hard to make me happy."

As soon as the gag is out I tell her, "My god, you look so fucking hot!"

"Oh you sweet talker, now shut up and get to work." And just like that she's on my mouth and I start sucking and licking her pussy. Just seeing her and having her on top of me drives me crazy. Now I’m desperate to cum and would be begging if my mouth wasn’t full. Instead the random stroking continues and I'm no closer to cumming than I was 10 minutes ago, and I won't be any closer 10 minutes from now, or for however long Kat decides to keep me here. Since I can't speed things up, I concentrate all my efforts in getting her off. Part of me is hoping if I do a good enough job she'll reward me by untying me so I can fuck her. Oral sex was always foreplay for her, no matter how long I go or how often she cums, she always craves a cock inside her after, and I'm hoping the same happens here. Imagine my surprise when after her third orgasm she staggers off the bed and instead of freeing me replaces the gag and tells me, “Good boy,” before leaving the room All I can do is moan into the gag and await her return, which I realize may be a while as I can hear the shower running.

As I lay there waiting I’m both loving and hating it, but definitely getting exactly what I wanted as I’m being teased for longer than I’ve ever managed before. Some time later the door opens again and Kat is there wearing only a towel, her hair still damp from the shower. “It’s been over an hour, how you doing?” I can only moan and whine through the gag. “What’s the matter, Victor? More than you imagined? Too much for you to take?” I don’t want to admit it is so I only whine again and shake my head in response. “How many times when we were fooling around would you pester and beg me to tease you, and I would, but it was never enough. It was kinda boring for me and selfish of you to keep asking. But this...this is a great idea! You’re getting exactly what you thought you wanted and all I have to do is nothing!” The towel dropped revealing her gorgeous, nude body as she slowly walked toward me, “You said you wanted two hours...nope. I’m going to keep you like this all night, baby! I changed plans with my friend, she’s coming over here. We’re going to order pizza and watch a movie. Maybe I’ll tell her what we’re doing and show her what a pervy little slut you are.” She got back on the bed, straddling my head. I could smell her excitement rising again, but with the gag and ropes could do nothing about it. “You remember Sophie? Imagine if she saw you like this. You’d never be able to look her in the eyes again! Or maybe I’ll just say I’m house sitting for you and you’ll need to be quiet to keep this our little secret. I haven’t decided yet.” She lowers herself so my nose is almost buried in her. I can still breathe, just barely, but her scent overwhelms me making my cock surge. “Do you think she’d be disgusted? Or maybe she’d want to sit where I am. Would you like that? Forced to please both of us while your poor cock gets teased non-stop. Fuck! I really need to get dressed but want to feel your tongue again. I’ll just settle for this…” Her hand slid down her body and began to massage herself, slowly rubbing at first but quickly picking up speed and soon she was cumming on my face. Once again when she was calm she got off the bed and told me to behave myself and left the room, closing the door behind her.

As I lay there wondering which I’d prefer my mind drifted to Sophie. Her and Kat were close friends, and I had spent time with them on numerous occasions. She seemed like a good person, fun to be around, and she was just as beautiful as Kat. She’s blonde and much taller than Kat. While her body wasn’t as fit, she had perfect curves in the right places. The only thing that ever prevented me from asking her out was my “relationship” with Kat that she knew all about and my assumption that it would be too weird for everyone. She’d probably take one look at me like this and leave disgusted. Like Kat said, I’d never be able to look her in the eyes again. Of course in my current state my mind instead focused on the fantasy of her being turned on by it and joining in, which only helped to tease myself even more. In reality I didn’t want to risk being found out or calling Kat’s bluff, so I did my best to keep quiet once I heard voices outside my door. I had a small apartment with basically three rooms; the front door opened into the kitchen, leading to the living room and bathroom, and finally my bedroom. As the conversation slowed and the TV started playing, my mind began to drift. It had to have been around two hours by now and I wasn’t sure how much more I could take. I didn’t know which I needed more, an orgasm or just have this damn machine shut off! At some point I started moaning again and didn’t even realize until the door opened, startling me back to focus.

Thankfully, it was only Kat as she got close to me and whispered, “Just checking in. You know we could hear you? Better behave, but to be honest hearing you and knowing you’re in here is turning me on again. Here, let me prove it.” She quickly slid off her pants and underwear, then put her pants back on and her underwear over my face, both obscuring my vision and allowing me to smell her scent and nothing else. I heard my door open and close as she left me to stew in both my juices and hers. Time lost all meaning with only two of my senses able to register anything, the nerve endings of my impossibly hard cock and the aroma from her panties. Eventually it became too much and I furiously struggled to break free from my bonds, no longer caring who heard me. I just knew I needed this to end one way or another. I was so lost in my desperation I didn’t hear the door open or the voices. It wasn’t until the toy was pulled off my cock and the panties off my head did I realize what was happening. Both Kat and Sophie were standing next to the bed looking at my naked, bound body. Sophie with a look of shock, Kat with a bit of concern but mostly lust.

Sophie broke the silence, “Holy shit! You weren’t joking! How long has he been like this?”

Kat checked the time on her phone, after taking a quick pic of me despite my muffled protests. “Looks like a little over three hours. He always talked about how much he wanted this, but looks like I broke him. What do you think, Victor? Had enough?”

She finally removed the gag from my mouth, “Yes! Please, no more! Let me cum now, please!”

Sophie couldn’t help but giggle a little while Kat flat out laughed at my pleading, “Hmm, maybe just a little break before round two. What do you think, Soph?”

“Oh, shit, I can’t decide that. How the hell did he last three hours, anyway? No guy has that kind of stamina.” Kat made me explain to her how the machine worked and why I wanted to do this. I’m sure I was all kinds of red in the face, embarrassed at not only being in this helpless situation, but also having to explain my secret kinks to her. Naturally, none of this stopped my cock from staying at complete attention. Once I finished, Sophie’s eyes were wide, but her shock didn’t stop her from reaching out and very softly caressing my cock, causing it to jump around on my stomach. “Wow, I bet you’d cum in seconds if I stroked you, huh?”

My eyes screwed shut, “Yes, yes, please god, yes!”

Kat ordered, “Hey, look at her while you beg,” and for some reason I immediately obeyed and forced myself to keep eye contact with her.

“I’m kind of torn, part of me wants to see how much would cum out, but another part likes seeing you so crazy horny.” She kept lazily caressing my cock as she thought for a moment, “I have an idea, we’ll let your cock decide! We’re gonna leave the room for five minutes. If your cock is still hard when we come back more teasing, if it’s soft we’ll let you go. What do you think, Kat?”

She laughed again, “Sure, sounds good to me.”

“Cool! Who knows, if you can control yourself maybe I’ll even reward you with a blowjob. Imagine my lips all over your big cock and then taking you deep into my mouth until you finally explode. God, I hope I don’t drown! Anyway, five minutes.” They left and closed the door. For the first couple minutes my mind couldn’t help but picture Sophie sucking my cock, which of course kept my erection standing tall. I finally forced it aside and started using all the old tricks, thinking of family members, baseball statistics, boring stuff about my job...and it was working! As my breathing slowed my cock was gradually softening, that is until the door opened and both Kat and Sophie were standing there in only their bras and panties. It was a dirty trick and I didn’t stand a chance as my cock instantly sprang back to life before they were two steps into the room.

I moaned and began begging them to stop and to let me go. Sophie shook her head, “I dunno, we had a deal. It’s not our fault you can’t control yourself. But I’ll leave it up to Kat, this was her game after all.”

“No, this was his idea. I’m just helping out. But you have a good point. I’ll bet if he won and you backed out of the blowjob he’d be pretty upset. So guess it’s only fair.” Next thing I know Sophie is putting the gag back in my mouth while Kat is putting the toy back onto my cock. I’m in shock while they do this. They must be joking or bluffing. They can’t possibly be serious about tormenting me any further. By the time I fully realize what’s happening, I begin thrashing and shaking my head, begging them to let me go, but of course they only hear muffled noises and my limited movements are futile.

Sophie seems to have second thoughts, “Hey, I don’t know about this. Maybe he’s had enough?”

Kat studies me for a second, “Nah. That’s one of his things. He likes to beg you to stop, but deep down he gets off on you saying no and doing it anyway. Trust me, he wants this.” Normally she’s right, but not this time. I truly want this to end, but instead the machine is turned back on and it goes back to work mindlessly teasing me. “C’mon, let’s finish the movie, we’ll check on him after.” I’m still shaking my head, but Sophie reluctantly agrees and they leave me alone. The break, as short as it was, turned out to be a lifesaver as I was able to handle this round of teasing a little better. At first, anyway, but soon my lust and frustration return to their previous levels and I am desperate to cum. I’m left in this state for at least another half hour, but I can’t really be sure. Maybe it was only ten minutes, maybe it was two hours, I only know when they finally return, fully clothed this time, my eyes are full of tears as I plead for mercy through the gag.

In answer to my prayers, Kat turns off the toy and says, “We’ve been talking and think you’ve had enough, but wanted to give you a choice. We’ll stop now, even have this thing make you cum, or Sophie here can give you that blowjob she mentioned earlier.” My eyes went wide and I began nodding furiously, “Hold on there, big guy. There’s a catch. If you want the blowjob you have to suffer through another movie. What do you think?” She removes the gag and as tempting as it is, there’s no way I can suffer through another couple hours of teasing and immediately tell them so.

Sophie leans down by my head, wipes a few tears off my face, and sexily whispers into my ear, “Are you sure? I was feeling sorry for you at first, but Kat convinced me you really like this and probably want more. And I know you’d love to feel me sucking that poor, horny cock of yours. Did I mention I can deep throat you? I could make you cum so much harder than this silly toy. You have no idea.”

Fuck, that sounds so good! I doubt I’ll ever get this offer from her again, and it’s so tempting to say yes...but I can’t. I just can’t take any more. “Oh god, I want that so bad, but I can’t handle any more teasing. Please just let me cum!”

She had a pouty expression, “Fine. Your loss. Enjoy fucking a machine.”

Kat couldn’t help but laugh at her, “Bet you never thought you’d see the day where a guy turns you down to suck him off.”

That only seemed to make her mad, “It’s not funny!” She turned back to me, “Now you have to get my permission to cum.” She had Kat show her how to use the manual controls and started it up again but on the slowest setting, “Here’s the deal. When you get real close you have to beg me for permission and I’ll decide if you’re ready or not. I promise I’ll let you soon, but I think you deserve just a little more of this for turning me down.”

I wanted to argue but was in no position, so meekly replied, “Whatever you say, Sophie.”

She smiled wide at that and asked Kat, “Sound good to you?”

Kat laughed again, “Whatever you say, Sophie,” then they both laughed. Despite my insane levels of frustration, the slowest speed was still not enough to bring me to the edge. Maybe it would after an extreme amount of time, but fortunately neither of us had the patience and Sophie gradually increased the speed.

That was doing the trick. It was still slower than I’d prefer, but it was finally taking me to the place I’ve been craving for hours now. I wasn’t shy about letting them both know what it was doing to me. “Don’t forget to beg permission. If you cum without my say so we might leave you here all night!”

I was 99% sure that was an empty threat, but didn’t dare risk it. Once I was seconds away I begged, “Please, Sophie, please may I cum?”

She immediately shut it off, leaving my cock to throb in the tube while she told me, “No, I don’t think you’re quite ready yet. Take a break and we’ll try again. Also, why don’t you call me ‘Miss Sophie?’”

Defeated, I simply replied, “Yes, Miss Sophie,” which caused her to giggle uncontrollably. After letting me rest a few minutes she turned it on again at the same slow speed. She edged me seven or eight times this way. I was losing count and my mind! After the latest denial I was broken, “Please, Miss Sophie, please let me cum! I’ll do anything for you, please, please, please!”

She arched her eyebrow, “Anything? Really? Fine, if you’ll do anything then beg me to not let you cum.”

I was flummoxed and didn’t hide it well, “I, uh, but, uh, um…”

“You should be a little more careful when you say anything. Okay, I’m getting bored anyway. You have my permission to cum.” I was thrilled as she started the machine again. It was still at the same slow speed, but I didn’t care. Part of me feared she was playing another game and would deny me again, but my hope won out as I grew closer and closer. Even though she already said I could, I found myself begging for permission anyway. Instead of a response she simply turned the machine up to full. It surprised me, but not enough to stop an orgasm. I had never cum so hard in my life! My eyes were sealed shut, both from the overwhelming sensations, but also so I wouldn’t have to see the two of them watching me. The machine kept going, milking me dry, but soon the elation of release quickly turned into sensation overload. Instead of each stroke bringing me pleasure it became torture as my now super sensitive cock was being assaulted at high speed.

“Please, Sophie, please stop, please make it stop, too much, it’s too much…”

She smiled at me, “It’s Miss Sophie, remember? Besides, isn’t this what you’ve been begging for all night? Isn’t this what you wanted? I don’t understand, doesn’t it feel good?”

It was so hard to form words, “No, too good, too much, please, Miss Sophie, please stop!”

Instead she leaned in close again to whisper, “You know if that was my mouth I would have stopped. I would have made you feel even better than that thing and you’d be laying there thinking you were the luckiest guy on the planet. But no, you got impatient.” All I could do was repeat “please” over and over again while Sophie simply watched my expressions from a few inches away until finally the damn thing stopped and I sagged into the beg, desperately trying to catch my breath. Sophie quickly turned back to Kat, “Hey, what the hell?”

“C’mon, Soph. He’s had enough and you had your fun. I’m bored. Let him up and we can all watch TV together.” She grudgingly agreed and left the room while Kat freed my ankles and wrists. “I’ll let you clean yourself up. Come join us in the living room when you’re ready. Hope that was as much fun as you imagined!” She gave me a quick kiss and went to join Sophie in the other room. I didn’t move for several minutes, simply relaxing and replaying what I just experienced. I’m thrilled it happened, but also not sure if I ever want to do it again. But that’s a worry for tomorrow Victor. Right now I just want to clean up and get some food. I grab some tissues and clean myself off as best I can after removing the tube, then put on my robe and dash through the living room to the bathroom, trying to ignore the whistles and catcalls from the girls. After a nice, warm shower I throw on some sweats and a t-shirt and join them on the couch. I’m terribly self-conscious even though they both seem indifferent to everything that just happened. I eat some pizza while we watch TV together.

As it starts getting late, the ladies decide they need to head home. Everything still feels very surreal to me as I hug and kiss them goodbye. I almost start to wonder if this even really happened or was it just a fantasy in my head until Sophie says, “This was fun! We should do it again sometime,” then winks as they walk away.

[cl13a]

Awesome story! A personal fantasy of mine. Femdom + milking machines + bondage is perfect. I can't wait to see what happens next...

[alejandro979]

It's indeed awesome story!