Someone to Watch Over Me Pt. 2

[lovesthepain72]

This whole thing started as a simple short story, but has taken a life of its own and I'm just along for the ride. We'll see where it takes us and how long it lasts, but for now enjoy part two. In case you missed part one, you can find it here.

Someone to Watch Over Me Pt. 2

“Jesus, Victor, why can’t you just be happy to fuck like any other guy?”

It’s been several months since Kat and Sophie put me through the tease marathon. I haven’t dared asked to do that again, going back to using my machine on my own for no more than thirty minutes or so each time. Even though I often reminisce about that night and each time my cock swells at the memory, and even though I regret not taking Sophie up on her offer to trade more teasing for a blow job, I know I don’t have the guts to put myself in their hands again. Instead, Kat and I have gone back to casual sex while we’re both still single. I’ve also seen Sophie more often than I did before with the three of us hanging out together fairly often. Aside from a few lewd comments and references to that day or flirting from her, there was never anything sexual between us.

Even though I had my great teasing experience and was again having great sex with Kat, I always wanted something more. This time I had the idea of longer term denial. Basically, only being allowed to orgasm whenever Kat wanted. I knew the idea wouldn’t appeal to her but I came up with another workaround that would give me the experience without her having to change our relationship. I bought myself a chastity cage. It was a custom fit and very comfortable. I started locking myself up anytime I wasn’t with Kat, making sure there were no issues with sleeping, moving around, etc. Of course anytime I got too excited I was able to unlock myself and take care of it, which is why Kat and I were talking now. I showed her the cage and asked if she’d hold the key for me.

“I thought after the last time we got that out of your system since you never brought it up again. So how is this different and what am I getting out of it?”

She made me feel like a jerk for bringing this up, but in for a penny, in for a pound, so I plowed ahead, “So I’d lock this on and you’d keep the key, so I wouldn’t be able to remove it without you. Meaning I couldn’t have sex with anyone else, masturbate, or even get hard. When we’re together if you want to we can unlock and do everything we usually do, otherwise I’d stay locked.”

She did not seem impressed, “I dunno. You’ll just start pestering me about unlocking you or you’ll be so pent up when we do have sex you won’t last more than a couple minutes. Still not seeing the upside for me.”

Had to admit she has a point. I was quickly reminded of what she told me before, saying how selfish I was always wanting her to tease me. I started feeling like an asshole, “You’re right. Sorry. I really like hanging out with you and the sex is great. Not sure why this stuff turns me on so much, but just forget I mentioned it.”

She sat in silence for a moment, “Ok, tell you what, we can give it a try. But you have to promise to never ask to be released. The first time you do you get the key back and don’t bring it up again. Also, if you’re no longer able to satisfy me because of it, same thing. Sound fair?”

“Uh, yeah. As long as you’re sure. Sounds good to me.” I unlocked it and we didn’t discuss it again until the next morning when I was getting ready to leave her place.

“Okay, put it on and give me the key.” I did as I was told. “You’re sure about this? Can you even clean yourself and use the bathroom?” I assured her I did plenty of testing and would be fine. The next couple months went pretty well. I was really enjoying the lack of control and being dependent upon Kat for any kind of sexual relief. True to my word, I never once asked to be unlocked and any time we got together I made sure she was satisfied, probably overcompensating for fear of being premature. As far as I could tell, she didn’t mind all of the extra attention. We normally saw each other fairly often. The longest I had to wait was a week one time, which was tough but still exciting. Of course, Kat just had to tell Sophie about this so whenever I saw her she made a point to comment on it, be extra flirty and handsy with me, and even going so far as “checking” that I was still wearing it one time. Those nights had me even more eager to hop into bed with Kat and relieve my frustrations. She never complained and is probably one of the reasons we hung out with Sophie more often lately.

Fast forward to today, Friday night. It’s been a week again since the last time I saw Kat with both of us being busy with work. We had plans to get together, which I was more than ready for, until she sent a text cancelling. I was heartbroken, but she had some kind of family emergency and needed to leave town for a few days. She never mentioned my key, and I knew better than to bring it up, so simply wished her the best and hoped to see her soon. The weekend was going to be tough. Sophie wanted to meet up, which we had never done without Kat before. I declined knowing it would just make things worse for me, but she was persistent so I gave in and we made plans for Saturday night. I had enough sense to at least meet in public, which apparently she took as a challenge. She dressed in the tightest and most revealing outfit I’d ever seen her in, not counting that night in my bedroom, of course. Every chance she got she was either touching me or bending forward so I could get a good look at her cleavage. I’d occasionally wince in pain as my cock tried in vain to get hard in its small cage, which of course she noticed. I start to wonder if we created a tease monster or if she just enjoys messing with me.

After a few drinks she became bolder, telling me how she wants to tie me up to my machine again and watch me squirm, which is exactly what I’m doing now as she’s talking. Where earlier my cock would try to get hard, fail, then go soft again, now it’s just permanently struggling against the cage. I should leave, instead I futilely try to change the subject and stop ogling her, but fail at both. She finally asks, “Do you really not have a spare key? Tell me the truth, I won’t tell Kat, promise!” I assure her I don’t have any copies. “Damn, that’s pretty hot. I never understood why you and Kat aren’t a couple. You guys have such a weird relationship. You like hanging out together, you have sex, what else is there?”

“Oh, well we both agreed we’re better off like this. We tried it at first, and something just wasn’t right. We both knew it. It’s hard to explain. It was just a feeling, you know?”

She contemplated that for a second, “Yeah, I guess so. Well if that’s the case, then why didn’t you ever ask me out? Do you not really like me or find me attractive?”

“Are you kidding? I’ve always liked when you come out with us and,” I lowered my voice a bit, “I haven’t been able to get the picture of you in your underwear out of my mind. You’re gorgeous.”

She blushed a bit, “Thanks. Then why haven’t you asked?”

“I’ve definitely thought about it, but you and Kat are so tight and I figured it’d be awkward. And if it didn’t work out between us it would be even worse. I didn’t want to get in the way of you and Kat’s friendship, or lose either of you as friends. Does that make sense?”

“Yeah, I get it. Same reason I never said anything before, I guess. I was going to talk to Kat about it after that day we all spent together, but then you two started up again and decided against it.”

We both were quiet for a moment until I changed the subject to our shared worry for Kat and her family, but that doesn’t last long as Sophie abruptly says, “Ah fuck it, why don’t you come back to my place? I want to see your cage.” I almost spit out my drink. “C’mon, what’s the big deal? I’ve already seen you buck naked and Kat gave me a copy of that picture she took of you too! Plus, as you obviously remember, you’ve seen me in my underwear. It’s not like we can have sex. Let’s go.” Without waiting for an answer, she grabbed my hand and led us to the exit. Her apartment was only a few blocks away so we walked/stumbled our way there. She didn’t waste any time once we were inside, “Okay, drop your pants, let me see!”

I nervously laughed as I slowly unbuckled my belt. I was standing in the middle of her living room while she sat in a comfy chair watching me, making me feel even more uncomfortable and self-conscious. Once undone I decided to stop delaying the inevitable and pulled both my pants and underwear down together. She couldn’t help but laugh once she saw it. Between that and my general embarrassment at this situation, my cock was mercifully flaccid. “Come closer, I want to see.” I started shuffling towards her before she told me to take off my shoes and ditch the pants completely. After doing so I walked in front of her. She sat forward and took the cage in her hands, inspecting it closely while fondling the cage and my balls. As I’m sure she intended, I was starting to get hard again, “Wow, look at it trying to break out! That must hurt like hell!”

Despite her concern, she never stopped fondling, “Yeah, it’s pretty uncomfortable.”

“I’ll bet. Are you sure you don’t have a key on you?”

“Yes, Kat has the only one.”

“Hmm, too bad.” She stood up in front of me and pulled my shirt up and off so I was now completely naked, and then surprised me by giving me a deep and passionate kiss that I was all too happy to return. My hands instinctively started caressing her sexy body, not caring about the discomfort I was causing my cock. We kissed for a few minutes before she slowly turned us around and gently pushed me down onto the chair. “Let’s see if you can bust out of it.” Sophie turned on some music and spent the next several songs giving me the best lap dance I’ve ever experienced. After the first song her dress came off. The next she removed her bra, revealing her glorious breasts to me for the first time. Finally, her panties were removed and she straddled me on the chair, grinding herself against my cage. As I cupped her breasts and we kissed again, my cock was in absolute agony but I didn’t care. I had a sexy goddess, who apparently got off on teasing me, naked on my lap and I wasn’t going to let her go so soon.

She broke our kiss long before I wanted to, “Fuck! This is teasing me now. Come on!” She got up and pulled me to my feet, leading me to her bedroom. She practically threw me on her bed and quickly climbed on top of me in a sixty-nine position. I dove into her sex like I was starving while she finally gave me the blowjob she promised a few months ago. Of course, this wasn’t how I’d imagined it! As she pressed herself harder and harder against my face it was becoming more difficult to breathe, but I didn’t care. My sole focus was making this gorgeous woman cum! Soon my efforts were rewarded as she sat up and screamed out in orgasm, putting her full weight on my head making it impossible for me to get any breath. Despite my light headedness I kept licking, ensuring she was completely satisfied. She rolled off of me right before I thought I might black out, leaving me a mess trying to catch my breath.

Sophie spun her body around and laid next to me, “Wow! Who knew locking up a cock could make sex better?!” Her hand began fondling my cage again, “Still wish I could open this up, though.” A few seconds later she was sound asleep, half her body draped over mine with her hand resting on my angry, confined cock. It took some time, but eventually I was able to calm down enough to fall asleep as well.

The next morning was slightly awkward. Even though I think we both loved what happened, we agreed the drinks may have had something to do with it and that we should not mention this to Kat. I left in a hurry and took a cold shower as soon as I was home, hoping to dull the ache in my balls. I was tempted to text Kat and see when she was coming back, but decided better of it. Then I considered texting Sophie but knew that was a mistake on so many levels. Instead I tried to forget about women or sex or anything that might cause further frustration. I did well for a few days until the dream I had Tuesday night. When i woke up the next morning the details were hazy, I only remembered women and sex, the two things I’ve been trying to ignore. My poor cock was throbbing in its small prison and after my long, cold shower I broke down and was ready to text someone...but who? The decision was made for me as I saw I was already part of a group text with Kat and Sophie. Kat’s father became suddenly ill and passed away over the weekend. She wanted us both to come out for the funeral on Friday and offer our support. Hate to say, but I was a little thankful as that completely killed any lingering sexual desires I had. Naturally I agreed and made plans with Sophie to rent a car and head out there.

As I drove the conversation was a bit awkward, but necessary. Sophie began, “So you never texted me.”

“Yeah, sorry, I wanted to, but…”

“Yeah, no, I get it. I know you and Kat aren’t dating, but still kind of feels like I betrayed my best friend. And now that I know we did that while her dad died makes me feel like an asshole.”

“Jeez, now I feel bad too. But that wasn’t the only reason. You had me so frustrated I was afraid even a text from you would make it worse.”

That seemed to life her spirits a bit, “Oh yeah? That was pretty fucking hot, huh? And your mouth was so good, I haven’t cum like that in a while.”

My mind began drifting to that night causing a chain reaction of my cock swelling, hitting the confines of the cage, and causing me to wince and squirm in discomfort, “Um, maybe we should change the subject?”

That just made her bolder, “Oh? What’s the matter? Is it getting tight down there? I don’t know why but I love seeing you all frustrated. I admit when I first saw you tied up in bed it freaked me out. I didn’t believe any guy would subject himself to that and I felt sorry for you. But Kat convinced me you were really into it, and then when I saw you struggling and begging something clicked. Fuck, I would have left you there all night if she didn’t stop me.” She paused for a moment, “Sorry. This is fucked up, we’re going to a funeral. I’ll drop it.” I assured her it was fine, but inside I was completely torn. Sophie sounded like my dream girl, but she was right this wasn’t the time or place to think about it.

The rest of the ride was relatively quiet. Thankfully, once we got to Kat’s family home we were able to forget about our tiny problems and focus on her. Kat was, understandably, a bit of a wreck. We let her cry on our shoulders and stood by her and was there for her the entire day. Late that night after everyone had left, the three of us sat at the kitchen table eating some leftover snacks with her mother. Kat broke the somber silence, startling us all, “Fuck! I need to get out of this house! Oh, sorry mom.”

She smiled, “That’s ok, sweetie. Why don’t you kids go out, have a drink. Honestly, I wouldn’t mind some peace and quiet here for a bit. I already made up the spare room for you, Sophie. And Victor, I'll get you some blankets for the sofa. Go, try and have some fun.” We tried to argue, but she was having none of it so the three of us went to a local bar.

The ladies grabbed drinks while I stuck to soda. Kat downed a few pretty quick and Sophie wasn’t that far behind. Before I knew it I had two drunk women on my hands. We were just making stupid small talk and telling bad jokes until Kat blurted, “Hey Victor. I didn’t forget about that thing you’re wearing. I have your key in my purse somewhere”

“Um, that’s ok. Don’t worry about it right now.”

“Oh c’mon, it’s been what, two weeks? When was the last time you ever went that long? Ever? You must be ready to explode!”

Sophie couldn’t help herself, “Oh, you have no idea...I mean…”

Somehow Kat knew exactly what she meant, “Hey, did you two hook-up? I mean, I know you didn’t fuck, but what did you guys do?” I was like a deer in headlights but Sophie spilled her guts, telling her more details than she probably needed. We both felt ashamed as a silence seemed to linger until Kat said, “Well it’s about fucking time! I kept waiting for one of you to ask me about the other or do something. I think you guys would make a great couple.”

I was shocked, “But Kat, what about our, uh, relationship?”

“Eh, I’ll miss having sex with you, not gonna lie, but even without sex we’re still friends. Just boring friends.” We all laughed, though two of us nervously and very confused, “Besides, I should quit messing around and try having a normal relationship with a guy, no offense Victor. And really you should too! Well, with a woman I mean. Here, let’s make it official.” Kat then began digging through her purse and pulled out my key! I put out my hand, but to my surprise she gave it to Sophie instead! “There, take good care of it.”

Sophie’s smile was a mile wide, “Oh, you know I will. What do you think, Victor?”

I couldn’t help but smile back, “I think I might be in trouble.”

“See? You guys are cute. Ok, I think I need to be sick and go home.” Sophie stumbled with her to the ladies room. Once that was taken care of I drove them back to Kat’s house and we put her to bed. Sophie stayed with her in case she got sick again and I crashed in the guest room. The rest of the weekend was uneventful as we helped Kat’s family around the house. Sophie and I got along great without anything sexual between us, which was good to know. We kept the same sleeping arrangement Saturday night, much to my dismay, and Sunday morning the three of us drove back to the city. Kat insisted she wanted some time alone, so we dropped her off and returned the car, then Sophie and I went back to my place.

Instead of attacking each other, Sophie sat us down, “So, we should probably talk. I know we don’t know each other that well and wanted to see if you wanted me to keep your key or not. I’m really into seeing you all frustrated and horny, and I really like you. When I get into something I tend to go overboard and could see myself giving you more than you could handle, especially since this is all so new to me. Just wanted to warn you and see what you think.”

Is it wrong that her saying that made me unbearably hard right now? “Wow. I’ve been turned on by this for years, but never really experienced any of it until recently. You’re the first woman I’ve met that gets it. I don’t know how much I can take, but I’d like to find out with you.”

She smiled, “Awesome. Have you been hooked up to your little toy since that one day?”

“Um, not like that, no. That might have been too much, but if I’m being honest, I kinda wish I took you up on your offer.”

That piqued her interest, “Oh really? Well how about now? The offer still stands, let me tie you up and tease you more and I’ll give you the best blowjob of your life!”

She can’t be serious? I’m not sure which would be stupider to consider it or to pass it up. “Jeez, I dunno. It’s been over two weeks and I’m already going crazy.”

“Ah, ok, then this should help. I’ll only unlock your cage today if you’re naked and tied to the bed, otherwise we’ll wait. What do you say?”

This is exactly what I’ve been dreaming about! I’m sure one way or another I’ll regret this, “Ok, you win. Tie me to the bed, please.”

She clapped with glee, “Yay! But don’t forget, call me Miss Sophie from now on when we’re playing, got it?”

“Yes, Miss Sophie.” We went to my bedroom and set up the restraints and my toy, going over all the programming and controls for her. Once she understood the controls I was stripped down and secured to the bed.

She left for a moment and returned with a keychain, “I need to find a more convenient place for this,” and unlocked the cage. For the first time in weeks my cock was able to stretch out and get hard. I sighed in relief. It felt so good at that moment that I didn’t care what would happen next. She slid the tube on me and started up my program. Feeling it slide up and down was heavenly, watching Sophie give me another striptease was even better. Just five minutes in and I was already feeling desperate to cum. I have no idea what she has planned or how long I’ll be here, my only choice is to lie there and enjoy the show as she’s now down to her underwear. After the bra comes off she dances towards me and lowers her breasts to my waiting mouth. She practically smothers me as I kiss and suck on each nipple. She stands back up and turns away from me. While looking back at me over her shoulder, she bends at the waist and lowers her panties to the floor. After tossing them aside she saunters back towards me and climbs onto the bed, straddling my head. I have an odd sense of déjà vu going back to the last time I was tied like this, and begin licking and pleasing her. It isn’t very long before I’m rewarded with her screaming out in orgasm. As she slowly gets off the bed, she tells me, “Fuck! That was even better than last time! It’s like the hornier you are the better it feels. Maybe I should never let you cum!” There’s genuine fear in my eyes as she grabs the gag and places it in my mouth. “I get really sleepy after an orgasm, so I’m going to crash on your couch for a bit while you’re busy in here. Be a dear and don’t disturb me or I might have to lock you back up before your blowjob!” I beg her no through the gag, but she ignores me as she collects her clothes and leaves the room, closing the door behind her.

I couldn’t see any clocks so had no idea how long she left me there. I only know it was almost no time before I was as desperate as I was at any point the last time I was in this position. It took all of my will to stay still and not make any noise. I was positive this time that she wasn’t bluffing. It must have been a couple of hours when the door finally opens again and I immediately begin thrashing and begging. Sophie, fully clothed now, comes and sits on the side of the bed, watching my face as I break down. Once I tire myself out she removes the gag and I weakly beg, “Please, please, Miss Sophie, please just let me cum!”

She let me go on for a couple minutes, “Damn, why does watching you beg turn me on so much! If you’re not careful I’m going to have to ride your face again and take another nap.” I stopped begging and could only whimper. She chuckled and turned off my toy, removing it from my cock. She began gently caressing my hardness with her soft hands, “Now remember, you can never cum without my permission. That’s a permanent rule for you, got it?”

“Yes, Miss Sophie.”

“Good boy.” I thought a machine would be able to give me the ultimate tease, but was I ever wrong unless Sophie is some kind of robot. Still sitting on the chair, she began stroking me slowly, gradually picking up speed. It didn’t take very long for me to beg to cum and of course she promptly stopped telling me, “Good boy,” and rewarded me by removing her top. After letting me cool down for a few minutes she repeated it. She’d edge me then remove another article of clothing, each time she’d vary how she stroked me. Sometimes quickly getting me there, other times dragging it out and very slowly taking me to the edge. When she was nude, she laid down next to me, pushing her breasts up against the side of my chest, and draping a leg over mine. One hand was back on my cock while her other went down and began touching herself, “I’m going to tease myself while I play with you. When I can’t take it anymore, then we’ll see about finally giving you some relief.” Before I could say anything, her lips were on mine and we moaned into each other’s mouths as she worked us both up. The only time we’d break the kiss is when I got close and begged her to cum, “No, for now I want you to beg me to stop when you get close. Beg me to keep teasing both of us.” Like an idiot, I did as she told me. Over and over she edged me, edged us.

The longer we went, the more passionate her kisses were becoming and the more her body was squirming against mine. “God, this is driving me crazy! I can see why you like it so much. Maybe one of these days I’ll let you tie me down.”

“Imagine how much better it would feel if we both came?”

She laughed, “Naughty boy. No, I’m enjoying this too much. Besides, I just had an orgasm a couple hours ago. I’m fine to wait a little longer.” I could only moan in response. The only thing more powerful than my desperation right now is my desire to please her, so each time I reach the edge I continue begging her to stop.

Many, many edges later I reach another breaking point, “Please let me cum! Please, Miss Sophie, I can’t take it anymore, please!”

She leaned up so her face was hovering above mine and watched me plead for a few moments. “Okay, I guess you’ve waited long enough.” She spun around putting us back in a sixty-nine position and right before lowering herself onto my face told me, “Lick me slow and tease me.“ In my state it was difficult to go slow, especially when she took me inside her mouth. She could have finished me off in seconds but was taking her time yet again and dragging it out. I struggled to keep my tongue moving slowly despite her wiggling and pressing herself harder onto me as she searched for more stimulation. As her head slowly bobbed up and down it was becoming more difficult for me to breathe. Finally, her pace quickened and she pressed herself down on me just hard enough that I could not breathe at all. As my long awaiting orgasm was approaching, my lungs began to burn for air. Unable to move my head, I begged into her pussy to ease up so I could breathe again. Instead, she took me completely in her mouth, proving she wasn’t just bragging about her ability to deep throat. I don’t know what exactly she did, but it felt amazing and seconds later I had the best orgasm I could remember. Her mouth never left my cock as I came and came until I grew very light headed and passed out.

Next thing I knew Sophie was lightly slapping my cheeks, asking if I was ok. I was a little disoriented as my eyes fluttered open and I wondered why I couldn’t move my arms or legs, until I remembered where I was and what we were doing. I focused on Sophie and she looked relieved, “Whew, you scared me there. Are you ok? What happened?”

“I think so. I couldn’t breathe,” She apologized, but I assured her it was okay and I was fine. “Did you pass out before or after your orgasm?”

I smiled, “After. I think that helped knock me out.”

She smiled back, “Good. Now it’s my turn. I’ve never been teased like that before.” She held my soft cock, “Think we can wake him back up?” Without waiting for an answer she caressed and fondled me until my greedy cock was erect and ready for round two. Straddling my body she slid me inside of her. Still bound and helpless I could only watch as she sat up and rode me. Ordinarily, I doubt I’d be able to last very long watching this sexy woman’s body bounce up and down on me, but since I had just cum I had the stamina she needed. Her first orgasm hit her quickly, no doubt thanks to the teasing she gave herself. Her second took a little longer. After her third I could finally feel myself getting close so I asked for permission. She promptly stopped and got off of me and the bed, “Greedy boy. You already had one today. Can’t spoil you so soon.” I was too in shock to protest or make any sounds as I watched her leave the room. I could only lay there and stare at my cock, still hard and glistening with her juices.

Gradually it began to soften and a moment later she returned drinking a glass of water. After setting it down she sat on the bed and freed my ankles, then my wrists and I immediately sat up and began kissing her passionately, which she was more than happy to reciprocate. “Mmmm, guess you had as much fun as I did?” I assured her that was true. Before things could escalate, she had me drink some water to rehydrate and suggested we clean up and eat something. Taking my hand and helping me up, she led me to the bathroom and we took a long, hot shower together. We helped each other clean up, paying special attention to a few obvious areas. By the time we rinsed off I was hard and throbbing again, but instead of acting on it I found myself naked in the kitchen making sandwiches for us while Sophie was lounging on the couch, naked as well. I joined her and we snuggled under a blanket together, watching TV and eating our sandwiches. That’s how we spent the rest of the day, and of course after we finished eating she made sure to place her hands on my cock, keeping me hard as much as possible.

When it was time for dinner, she went and grabbed the chastity cage and some frozen vegetables from my freezer. After icing down my cock she put the cage on me and locked it. We got dressed and went out for dinner, said goodnight and parted ways with promises to see each other soon. As I walked home alone replaying the day's events and feeling my cock begin to swell against its prison, wondering when she will let me be free again to orgasm, I smiled realizing how lucky I suddenly was.

-----------------------------

I feel like I could write about Sophie and Victor (and Kat too?) for a long time. Maybe not too soon, but I can see coming back to them at some point. Stay tuned!

[CagedAnimal]

WOWZA! Super hot story!! Thanks for sharing here