The Cruelest Edging Challenges Ever
By BruceTheBoss(switch male)
November 22, 2024
NOTE: Originally published by me on Literotica.com (erotic story site.) I am the original author of this work.
*****
My girlfriend, Sharona, had spent the last week talking nonstop about some new kink she wanted to try. "Hey Zane, let's do it. Tomorrow!" I woke up next to her in bed on Friday morning before we had to get up and get ready for work. "Do what tomorrow?" I turned to face the beautiful redhead lying next to me. her huge breasts spilling out of her black lacy nightie. "My edging fantasy! I want to tease you ALL day tomorrow! Just mercilessly. Your cock will want to cum so bad, and I'll let you cum at the end of the day! Oooh I can't wait to see the volume and how far your load shoots out after all that!" I was horny as fuck now and put my hand on her right breast. We fooled around for a few minutes but then had to get ready for work.
Mid-morning, I got a text from her. It says "Something to get you thinking about tomorrow" With a really nice down blouse picture in a black tight tank top, with half of her breasts visible! I got hard instantly, wishing the work week was over! Midafternoon, another sext, this time of her ass in just a red thong. She was really trying to get me hot and horny! I was hoping she wouldn't be too tired to fuck after dinner later.
Since this "edging challenge" wasn't until tomorrow, I was hoping to get sexual relief tonight. Sharona had other plans for my cock. We finally finished working, me as a software engineer working at home, Sharona as a manager of a clothing store in a mall. After she arrived home, we had a nice dinner, pizza from a local restaurant. I began to make moves on her later that night, but she explained she was too tired to have sex. I was content with the idea of masturbating - her talk about edging had turned me on. She grabbed my arm and began to kiss my ear. Between kisses I learned how tough this was going to be as she whispered her plans to me about this day of edging coming up the next day. "Zane, I know you love to stroke yourself to sleep, pretty much any night we don't fuck." Guilty as charged, I thought to myself, wondering why she had brought that up. "Did you jack off last night?" She asked, and I felt her hand on my knee suddenly. "Yes, I did" "Mmm. Ok so you need some time to really build up your cum." I had an idea what she was leading up to, knowing that she planned to edge me all day the following day. She wanted to build up my reserves, so to speak. I knew I would hate this, and sure enough she said what I was dreading: "I'd really like it if you don't masturbate at all tonight." She was no longer kissing my ear, so she was speaking at a normal volume now. "I won't tease you more tonight, but will you do this for me, pretty please?" Looking at me with those cute blue eyes, and hearing her sexy voice ask nicely, how could I say no to her? Without much enthusiasm, I mumble "sure, sounds like an interesting game to play for a couple of days." My balls where aching, this did not feel natural, to be this close to orgasm but not to cum. But for some reason I also got really turned on just by the thought of having my orgasm controlled by Sharona! I had never even considered doing something like this. I am a simple man: I get turned on, then I try to find a way to have an orgasm when I can, either through masturbation or sex with her. I tossed and turned, and eventually went to sleep...
THE NEXT MORNING:
After breakfast, Sharona came behind me while I was in the kitchen putting away my cereal bowl, and pressed her soft body against my back. She reached around to the front of my jeans and stroked them where my cock was, immediately making me erect. Whispering in my ear, she seductively asked "Are you ready for your first challenge?"
"I thought this whole day was basically a challenge, since you won't let me fucking cum until tonight" I replied.
"Oh no! I thought you understood I was going to make it really difficult for you. And I mean REALLY difficult, that is what turns me on, being wicked and making you want to explode when you can't cum, Zane!"
Damn, I had thought she had meant something like wearing slutty clothing, maybe putting a porno on the screen and making me watch or something. I had no idea what specifically she meant by "Your first challenge." I soon found out, as she took me by the hand and lead me to the bedroom. Pulling down my pants, she could see how hard I was from just the teasing already. She pushed me onto our bed, aggressively, which was quite out of character for her, and then she yanked the jeans completely off. I took off my shirt as well, without being told, and touched my own nipples, turning myself on even more, which was a terrible idea. She smiled at me and said "The first challenge begins now, sweetie! You are going to hate me so much...
CHALLENGE ONE: THE CRUELEST HANDJOB EVER.
Down to just my boxers now, Sharona began to massage my feet. It felt really good. She moved her hands up, nails on the back of my lower legs. I felt so nice and relaxed. My precum was beginning to soak the front of my boxers, and noticing this, Sharona said "I think these need to come off now!" Ever so slowly she started to pull them down. Over my hips, stiff erection out, then I felt my silky boxers slide down my legs and then off all the way, leaving me naked now. She tells me the first 15 minutes she will not touch my cock, and I can't touch it either, myself. My cock twitches, and I felt so turned on as she touched me all over my body. She removed her bra; I always love that moment when they are bared and the soft flesh spills out of the cups of the bra. She pressed her soft white breasts on my chest, brushing her nipples on my own, which sent shivers down my spine. "Are you ready for a nice slooooooooow handjob, one that does NOT have a happy ending?" God, the thought of receiving one of Sharona's awesome handjobs and then not having an orgasm sounded so difficult. I guess was the idea here! She pulled out a bottle of oil. She squirted a huge amount on her hands and rubbed them together. Sitting next to me on the sofa, Sharona finally put her slippery hands on the base of my shaft! Fuck yes this felt good. Oh God, up and down her hand went, this was really happening! Looking into my eyes, she spoke to me. Eye contact during a handjob always feels so sexy to me. "Does this feel good baby?" She rubbed my cock head. Then she kissed my nipples a bit, still rubbing just the head of my cock. This was driving me mad, my hips rocked up and I felt I might cum soon just from her stimulation of the head of my cock. Sensing my breathing and motions, Sharona figured out I was close to exploding actually, and she removed her hand from my cock completely. SO CRUEL! I had been so close to cumming!
She took her hand to my shaft and slowly began to stroke it up and down, FINALLY! I truly enjoy her expert handjobs as much as I enjoy fucking her sometimes, she is so deft at making my cock and body feel good with just her hands. I closed my eyes and imagined that she was on top of my shaft, grinding her cunt on me with her tits bouncing up and down as we fucked in my imagination. The sensations felt so good! She was keeping it slow, and I really wanted her to speed up but I lay back and let her take control of my pleasure any way she saw fit.
I have no idea how long this handjob was, but it did NOT have a happy ending, as she had promised, which was much worse in reality than it sounded when she had first said it. She slowed her hands to a stop and said "I think that is enough for now. Good boy, you made it without cumming!"
I wanted to ask her if she was cool with just stopping the all-day edging game now, my throbbing cock was primed for release, but I wanted to fulfil her fantasy and play along all day. But fuck it was a hard pill to swallow when she grabbed a clean pair of blue boxers from my dresser and put them on me. I was more used to her removing my clothing, and found it very erotic to have her put my boxers ON me again. My hard-on had not subsided. Not at all.
CHALLENGE TWO: THE CRUELEST BLOWJOB EVER.
"Lie on your back Zane!" Sharona told/ordered me, as she tugged at my jeans, having already unbuttoned and unzipped them. Yanking them down, she touched the outline of my erection through my blue CK boxers, precum staining the front of them as usual. I had been so close to cumming hours earlier, from a slow, long, teasing handjob, but without the happy ending the mind expects after having your throbbing cock stroked for an hour, hovering close to the edge of orgasm for the longest time you remember without getting that rush of endorphins and satisfaction from releasing the pressure.
I knew this was going to be much worse to get through, since the position she had me in hinted that she was going to be going down on me. The thought of a blowjob but with the same sad outcome of "Not cumming" as the cruel handjob I had already suffered through was very tough for my mind to accept. But I had signed up for this, hadn't I? I knew this was going to be delicious fun and also beyond frustrating! I was incredibly turned on by the control aspect of it too, knowing that I had signed up for 2 days of not cumming, with today being the final day, and the day she had decided to bring out the big guns to keep me beyond horny.
"Close your eyes babe!" she whispered. I felt her hands slide my underwear completely off. I still had a t-shirt on, which she told me to remove. I complied, and lay there nude, waiting for her mouth to kiss my cock. I bucked my hips up and opened my eyes, since the expected wet kiss had not reached my straining cock just yet. She had the most devilish grin on her face as she looked up into my eyes. "I thought I said to close your eyes! Bad boy, now you have to wait 5 more minutes before your aching cock can feel the wetness from my lips. Here, I'll give you a little hint of what the wetness will feel like soon." I kept looking up and she was drooling saliva from her mouth, which hovered only 3 inches from the tip of my cock. I felt her spit hit my skin, and it felt so hot!
I was really regretting agreeing to this twisted edging fantasy when I felt this drool slide down my shaft and touch my balls a bit. Oh fuck. My balls were so loaded with cum, and knowing that it was not yet time for that pleasure made this the most tortuous anticipation of a blowjob ever! And I knew I would lie there, and enjoy it immensely, until the part where she would inevitably withdraw and leave my poor balls aching even more. This was SO CRUEL!
My eyes closed, she suddenly just went for it! I was expecting more slow teasing before she practically deep throated my shaft, but in seconds I was balls deep into her mouth, and in the middle of a delightful blowjob, my mind floated as she worked her magic on my cock, using both her mouth and her tongue in interesting ways. She made beautiful sucking sounds that I could hear, adding another sense to the dimensions of pleasure I was in the middle of. She stopped for a brief moment, and for one terrifying instant I feared that this stage of the fun was already over, but instead she just wanted to treat me to a quick strip, and she peeled off her bra and brushed it across my nipples, fuck that was a nice touch! My nipples stiffened. Then she peeled her black lacy panties off, and brushed them right on my fucking balls, what a cruel temptress with that move! Her panties were wet in a spot in the front, and she made sure to mention that to me before she bent her head down again and continued to suck me off.
Her tongue was getting much more into the stimulation of my poor cock now, which felt heavenly as she languidly licked up and down, at one point putting both of my full balls into her mouth and swirling her tongue like mad! I felt like I would blow my load if her mouth swallowed my cock again, but somehow this did not happen and she actually did begin to suck me off again but this time gripping my heavy sac in her hands tightly! Fuck fuck fuck that was a mean thing to do, she knew how full my balls were as she sucked me good! She took me so Goddamn close to the edge I would have sworn I was already cumming and blowing a load into her mouth, but she backed off just in time. My cock twitched. And twitched. It was almost mimicking the muscular responses of an orgasm, but the lack of super intense pleasure is the way I quickly knew that I had not in fact blown it so to speak. She wrapped up the hot and heavy part of giving me head, and I sadly felt her lips completely withdraw, although I still had the wonderful tight warm feeling of her hand cupping my balls still. My entire center craved physical touch, anywhere, from her mouth, her hand, whatever part of her body, I just needed it between my legs! It was such a hard pill to swallow when the blowjob ended without me releasing that pressure whatsoever, my cock was dribbling a steady stream of precum, but no orgasm was given to me yet! And I knew I had hours to wait, and I was very afraid of what she could possibly have in store for me that evening. I knew I had to wait until tonight to cum, and it was only 4 PM!
Oh, it was so hard to get dressed after that! My cock was a leaking mess in my underwear now, and then my jeans on and the bulge in my pants still making it very hard to even zip and button my jeans. And putting on my shirt further took me away from the brink of cumming, being fully dressed now I felt so far, far away from that sweet fucking release I needed needed needed NOW!
As much as I love Sharona, a primal part of my brain hated what she was putting me through, as she took my hand and told me we were going for a walk, to cool me off. I was so worried someone would see how erect I was through my jeans as we walked out the front door of our house and took a leisurely stroll around my neighborhood, hoping not to run into any neighbors who wanted to make small talk. Sharona held my hand, it felt so innocent and cute, and to anyone watching we must have looked like just a happy couple going for a walk on a warm spring afternoon. What would people think if they knew I was under the spell of a cruel woman who was locking up my need for orgasmic release for days, and that I had only myself to blame for allowing it? My erection was not subsiding, and I just prayed it wouldn't be as noticeable as I feared it might be. I got even more aroused when she squeezed my hand. She stopped, and then titled her head up, and just...kissed my left earlobe. Hot breathing in my ear. She didn't say a word, she just used her mouth and tongue on my earlobe in primal sexy ways that set my cock on fire even more if that was possible. Of course it was possible, I thought, she had kept escalating the arousal more and more already, and I knew she wasn't nearly done with me yet!
We got back from the walk and didn't do much for a few hours. I was just waiting for it to get dark, knowing I was getting closer to the moment I would be allowed to have my orgasm. We had a nice dinner of leftover take-out Italian food from the previous night, and I watched a bit of ESPN, not really paying attention to the topic or even what sport they were talking about, my mind was so focused on horniness.
A few hours later, after a somewhat relaxing afternoon and evening, I looked at the clock. 10 O'clock. This teasing had gone on long enough, I thought, frustrated beyond belief already from over 36 hours of not having an orgasm, but being cruelly teased. "It's night time Sharona, I made it, oh God I just need to fuck you so bad!" I spoke.
She smirked and said "I told you there would be three challenges. We are now arriving at the third challenge dear. After that we will be near the point that you can't wait to get to.
Jesus Christ, what did she have in store for me? "Strip!" she suddenly ordered. Still a bit shocked at her aggressive behavior today, I quickly obeyed her and stood two feet away from her, stark naked while she was fully dressed still, wearing a long red skirt, and a black blouse. She snuggled up to me and drove me crazy, kissing my mouth. It felt odd to be fully naked but pressed against her skirt and blouse. It felt like she had no bra on underneath her top, which I loved. I looked and I could see her nipples. Her long red skirt was brushing against my cock and legs. Then she lifted her skirt up and I instantly felt her wet cunt brush up against the head of my cock! I was so ready to fuck her brains out. She took the initiative, and with her hand, she slowly guided my cock into herself, still wearing the red skirt, it was just moved up over her waist...I was inside her and it felt even better than usual after all this edging and teasing.
CHALLENGE THREE: THE CRUELEST SEXUAL INTERCOURSE EVER.
"Just sit still and let me move" she said as she rolled me over and put her weight on top of me. I reached under her soft black blouse, and cupped both of her tits. They are a bit smaller than average, a nice handful that felt so good in my hands. She got my whole entire cock inside her pussy and I bucked my hips up. She completely stopped moving, and moved my hands off her tits. "NO MOVING! SIT STILL NOW!" I did my best to calm my hips, and she sat still on top of me. She removed her top as I watched, mesmerized by the sight of her bared breasts. The skirt remained on her as she began to grind on me.
"OK lover, you already probably hate me so much. But here is your final challenge -- I want to cum right on your cock, and you are not to cum until after we fuck. Got it?"
"No way! I can't possibly do that; my cock is about ready right this instant!" I strongly protested.
"Yes, you fucking can Zane! So close, don't deny me this, I want you to complete the final challenge!" she yelled. She wasn't yelling out of anger -- the tone of her scream was obviously one of arousal, but it was a jolt to hear anyway, coming from my girlfriend who was normally not at all this demanding. "Here is the plan, I KNOW you can do it if you really try. It would be so wild for me to cum right on your cock when you are this horny. I'll make it as easy as possible -- I will do all the moving myself, you just sit as still as possible, and I will touch myself and cum as quickly as possible.
Fuck, fuck, FUCK! I wanted to cum so badly, this was torture. This was SO CRUEL! I suppose that was part of the fun for her, but she had no idea how hard it was for me to hold back a gusher of two days of built up cum when I was this aroused. I closed my eyes and then...I felt it, her wet cunt was sliding its way down my cock, and then I was all the way in, trying to sit still, and finding the sensation infuriating, not being able to just cum while she fucked me. But I was a good boy, and she did keep her word about trying to cum fast, so this wasn't too prolonged. I made the mistake of opening my eyes though, and watching her furiously rubbing her clit kicked up my arousal even more, somehow, and I didn't know if I could make it through her actual orgasm on my cock when I wasn't even allowed to cum myself! But I gritted my teeth....and felt her pussy muscles grip my cock, she clenched my cock tightly, and with no warning. This was the most difficult phase of the challenge, by far, because while I was denied, I had to feel, see, and hear her orgasm, right on my fucking cock! She dripped sweat down her little titties, and her nipples looked beautiful and perky, as she tilted her head back and let out a primal scream of sexual satisfaction. She spared me the full brunt of the wonderful clenching sensation that was making my cock about to explode beyond my control, and then she dismounted me, and thrashed her hips on the bed. I moved away from her body, as skin on skin contact would have probably made me cum even if my cock was not touched.
She came down and I looked into her eyes, and I began to stroke myself, seconds from shooting a load all over her body as she lay there in bliss. She looked at the clock. It was 11:18 P.M.
"STOP!" she yelled, startling me in mid stroke.
"Oh c'mon!" I protested, slamming the brakes on my hand motion.
"It isn't midnight yet!" She said.
"We never set a time, you just said tonight I could cum! Argh, please, I really can't bear this, my cock and balls are aching, and the thought of not cumming, I need to cum so soon, please, please, please?" I pleaded.
"Mmm...I love the begging, Zane!" she smiled. "Ok, fair enough, so I will give you these two choices: One, you can cum right now, or two, you wait until midnight...and you can do the same thing to me next weekend! Tease the Hell out of me, make me goon like a mindless slut, make my pussy a wet mess for 48 hours and not allow me to cum for two entire days! If anything, think of it as...revenge?"
My mind raced through the choices. I glanced at the clock. 11:23, so if I could make it through 37 minutes of just doing nothing, I would be able to turn the tables, and make her suffer like I was right now! I relished the thought of making her read erotic stories, and edge herself silly, and many other fiendish ideas I had for "Challenges" for her in this scenario. Cum now, or suffer through just a bit longer?
And the thirst for revenge just BARELY edged out the urgent throbbing need to CUM RIGHT THIS INSTANT! Just barely, this was the closet margin possible, and my snap decision could have easily gone the other way in my head. I wanted her to go through this Hell herself, get a taste of her own medicine, and I planned to be absolutely merciless, and...cruel even, as she had been to me! SO CRUEL!
"OK! As long as you promise to not tease me whatsoever until midnight Sharona, and then oh your next weekend is going to be rough!"
"Deal!" she said. She was about to shake my hand, both of us lying in bed together, me still naked, her in the red skirt and topless, but then she withdrew her hand, and said "I don't want to touch you, that might break the rules about teasing and turning you on more, dear!" She smiled. And to her credit, she did honor her word about not teasing me. I walked out of the room and actually got dressed in my boxers and t-shirt, and went outside the back door to our yard to get some fresh air...and hopefully cool off enough to restrain my libido for just about another half hour.
I paced back and forth a lot, that last half hour felt a lot longer than it actually was. But then one moment I happened to glance at the clock and saw it was 12:02 A.M!
I wasted no time. I didn't even try to make it to the bedroom, we were both in the living room. I ripped off my shirt, pulled down my boxers, and embraced her. I remembered that she had originally wanted to see the visual aspect of me shooting out a huge load of cum after all this edging, but I decided that fucking her brains out was the only thing that would do. She was still wearing just the skirt from earlier, the skirt I had fucked her in and also still topless, sitting on the living room sofa. I didn't even say a word, I just rolled her completely onto her back, and the I got on top of her to finish this off missionary style! I pumped away. I thought I would cum immediately, but I made it a good 2 or 3 minutes, enjoying just fucking the crap out of her, nailing her good, biting her shoulder a bit, my hands gripping her ass cheeks as I fucked away util I finally hit the sweet, beautiful point of no return, no stopping this gusher now!
And BOOM! It hit me. I could try to describe it to you, but you know what an orgasm feels like. So just imagine that feeling, multiply it by 3, and imagine that the feeling you normally feel most intensely in your cock when you orgasm is felt in every cell of your body as well. And the waves of pleasure just felt endless -- my mind could not even grasp when the end would be, it felt like the longest lasting involuntary spasms my cock had ever had. My eyes closed, I collapsed on top of her, still inside her, still quite hard, my cock still quivering. I have no idea what happened next to be honest, I think I must have blacked out when I was still inside her, and then I must have woken up some undetermined amount of time later, and I found myself naked on the sofa, with Sharona sitting on a chair 5 feet from the sofa, now dressed in a pair of purple silky pajamas that I knew were here favorite pajamas. She smiled at me, and I smiled back.
Part of my own smile turned into a smirk at the very end, because I had just thought of a really lovely, cruel, beautiful, evil, and sexy way to tease her next weekend...
*****
My girlfriend, Sharona, had spent the last week talking nonstop about some new kink she wanted to try. "Hey Zane, let's do it. Tomorrow!" I woke up next to her in bed on Friday morning before we had to get up and get ready for work. "Do what tomorrow?" I turned to face the beautiful redhead lying next to me. her huge breasts spilling out of her black lacy nightie. "My edging fantasy! I want to tease you ALL day tomorrow! Just mercilessly. Your cock will want to cum so bad, and I'll let you cum at the end of the day! Oooh I can't wait to see the volume and how far your load shoots out after all that!" I was horny as fuck now and put my hand on her right breast. We fooled around for a few minutes but then had to get ready for work.
Mid-morning, I got a text from her. It says "Something to get you thinking about tomorrow" With a really nice down blouse picture in a black tight tank top, with half of her breasts visible! I got hard instantly, wishing the work week was over! Midafternoon, another sext, this time of her ass in just a red thong. She was really trying to get me hot and horny! I was hoping she wouldn't be too tired to fuck after dinner later.
Since this "edging challenge" wasn't until tomorrow, I was hoping to get sexual relief tonight. Sharona had other plans for my cock. We finally finished working, me as a software engineer working at home, Sharona as a manager of a clothing store in a mall. After she arrived home, we had a nice dinner, pizza from a local restaurant. I began to make moves on her later that night, but she explained she was too tired to have sex. I was content with the idea of masturbating - her talk about edging had turned me on. She grabbed my arm and began to kiss my ear. Between kisses I learned how tough this was going to be as she whispered her plans to me about this day of edging coming up the next day. "Zane, I know you love to stroke yourself to sleep, pretty much any night we don't fuck." Guilty as charged, I thought to myself, wondering why she had brought that up. "Did you jack off last night?" She asked, and I felt her hand on my knee suddenly. "Yes, I did" "Mmm. Ok so you need some time to really build up your cum." I had an idea what she was leading up to, knowing that she planned to edge me all day the following day. She wanted to build up my reserves, so to speak. I knew I would hate this, and sure enough she said what I was dreading: "I'd really like it if you don't masturbate at all tonight." She was no longer kissing my ear, so she was speaking at a normal volume now. "I won't tease you more tonight, but will you do this for me, pretty please?" Looking at me with those cute blue eyes, and hearing her sexy voice ask nicely, how could I say no to her? Without much enthusiasm, I mumble "sure, sounds like an interesting game to play for a couple of days." My balls where aching, this did not feel natural, to be this close to orgasm but not to cum. But for some reason I also got really turned on just by the thought of having my orgasm controlled by Sharona! I had never even considered doing something like this. I am a simple man: I get turned on, then I try to find a way to have an orgasm when I can, either through masturbation or sex with her. I tossed and turned, and eventually went to sleep...
THE NEXT MORNING:
After breakfast, Sharona came behind me while I was in the kitchen putting away my cereal bowl, and pressed her soft body against my back. She reached around to the front of my jeans and stroked them where my cock was, immediately making me erect. Whispering in my ear, she seductively asked "Are you ready for your first challenge?"
"I thought this whole day was basically a challenge, since you won't let me fucking cum until tonight" I replied.
"Oh no! I thought you understood I was going to make it really difficult for you. And I mean REALLY difficult, that is what turns me on, being wicked and making you want to explode when you can't cum, Zane!"
Damn, I had thought she had meant something like wearing slutty clothing, maybe putting a porno on the screen and making me watch or something. I had no idea what specifically she meant by "Your first challenge." I soon found out, as she took me by the hand and lead me to the bedroom. Pulling down my pants, she could see how hard I was from just the teasing already. She pushed me onto our bed, aggressively, which was quite out of character for her, and then she yanked the jeans completely off. I took off my shirt as well, without being told, and touched my own nipples, turning myself on even more, which was a terrible idea. She smiled at me and said "The first challenge begins now, sweetie! You are going to hate me so much...
CHALLENGE ONE: THE CRUELEST HANDJOB EVER.
Down to just my boxers now, Sharona began to massage my feet. It felt really good. She moved her hands up, nails on the back of my lower legs. I felt so nice and relaxed. My precum was beginning to soak the front of my boxers, and noticing this, Sharona said "I think these need to come off now!" Ever so slowly she started to pull them down. Over my hips, stiff erection out, then I felt my silky boxers slide down my legs and then off all the way, leaving me naked now. She tells me the first 15 minutes she will not touch my cock, and I can't touch it either, myself. My cock twitches, and I felt so turned on as she touched me all over my body. She removed her bra; I always love that moment when they are bared and the soft flesh spills out of the cups of the bra. She pressed her soft white breasts on my chest, brushing her nipples on my own, which sent shivers down my spine. "Are you ready for a nice slooooooooow handjob, one that does NOT have a happy ending?" God, the thought of receiving one of Sharona's awesome handjobs and then not having an orgasm sounded so difficult. I guess was the idea here! She pulled out a bottle of oil. She squirted a huge amount on her hands and rubbed them together. Sitting next to me on the sofa, Sharona finally put her slippery hands on the base of my shaft! Fuck yes this felt good. Oh God, up and down her hand went, this was really happening! Looking into my eyes, she spoke to me. Eye contact during a handjob always feels so sexy to me. "Does this feel good baby?" She rubbed my cock head. Then she kissed my nipples a bit, still rubbing just the head of my cock. This was driving me mad, my hips rocked up and I felt I might cum soon just from her stimulation of the head of my cock. Sensing my breathing and motions, Sharona figured out I was close to exploding actually, and she removed her hand from my cock completely. SO CRUEL! I had been so close to cumming!
She took her hand to my shaft and slowly began to stroke it up and down, FINALLY! I truly enjoy her expert handjobs as much as I enjoy fucking her sometimes, she is so deft at making my cock and body feel good with just her hands. I closed my eyes and imagined that she was on top of my shaft, grinding her cunt on me with her tits bouncing up and down as we fucked in my imagination. The sensations felt so good! She was keeping it slow, and I really wanted her to speed up but I lay back and let her take control of my pleasure any way she saw fit.
I have no idea how long this handjob was, but it did NOT have a happy ending, as she had promised, which was much worse in reality than it sounded when she had first said it. She slowed her hands to a stop and said "I think that is enough for now. Good boy, you made it without cumming!"
I wanted to ask her if she was cool with just stopping the all-day edging game now, my throbbing cock was primed for release, but I wanted to fulfil her fantasy and play along all day. But fuck it was a hard pill to swallow when she grabbed a clean pair of blue boxers from my dresser and put them on me. I was more used to her removing my clothing, and found it very erotic to have her put my boxers ON me again. My hard-on had not subsided. Not at all.
CHALLENGE TWO: THE CRUELEST BLOWJOB EVER.
"Lie on your back Zane!" Sharona told/ordered me, as she tugged at my jeans, having already unbuttoned and unzipped them. Yanking them down, she touched the outline of my erection through my blue CK boxers, precum staining the front of them as usual. I had been so close to cumming hours earlier, from a slow, long, teasing handjob, but without the happy ending the mind expects after having your throbbing cock stroked for an hour, hovering close to the edge of orgasm for the longest time you remember without getting that rush of endorphins and satisfaction from releasing the pressure.
I knew this was going to be much worse to get through, since the position she had me in hinted that she was going to be going down on me. The thought of a blowjob but with the same sad outcome of "Not cumming" as the cruel handjob I had already suffered through was very tough for my mind to accept. But I had signed up for this, hadn't I? I knew this was going to be delicious fun and also beyond frustrating! I was incredibly turned on by the control aspect of it too, knowing that I had signed up for 2 days of not cumming, with today being the final day, and the day she had decided to bring out the big guns to keep me beyond horny.
"Close your eyes babe!" she whispered. I felt her hands slide my underwear completely off. I still had a t-shirt on, which she told me to remove. I complied, and lay there nude, waiting for her mouth to kiss my cock. I bucked my hips up and opened my eyes, since the expected wet kiss had not reached my straining cock just yet. She had the most devilish grin on her face as she looked up into my eyes. "I thought I said to close your eyes! Bad boy, now you have to wait 5 more minutes before your aching cock can feel the wetness from my lips. Here, I'll give you a little hint of what the wetness will feel like soon." I kept looking up and she was drooling saliva from her mouth, which hovered only 3 inches from the tip of my cock. I felt her spit hit my skin, and it felt so hot!
I was really regretting agreeing to this twisted edging fantasy when I felt this drool slide down my shaft and touch my balls a bit. Oh fuck. My balls were so loaded with cum, and knowing that it was not yet time for that pleasure made this the most tortuous anticipation of a blowjob ever! And I knew I would lie there, and enjoy it immensely, until the part where she would inevitably withdraw and leave my poor balls aching even more. This was SO CRUEL!
My eyes closed, she suddenly just went for it! I was expecting more slow teasing before she practically deep throated my shaft, but in seconds I was balls deep into her mouth, and in the middle of a delightful blowjob, my mind floated as she worked her magic on my cock, using both her mouth and her tongue in interesting ways. She made beautiful sucking sounds that I could hear, adding another sense to the dimensions of pleasure I was in the middle of. She stopped for a brief moment, and for one terrifying instant I feared that this stage of the fun was already over, but instead she just wanted to treat me to a quick strip, and she peeled off her bra and brushed it across my nipples, fuck that was a nice touch! My nipples stiffened. Then she peeled her black lacy panties off, and brushed them right on my fucking balls, what a cruel temptress with that move! Her panties were wet in a spot in the front, and she made sure to mention that to me before she bent her head down again and continued to suck me off.
Her tongue was getting much more into the stimulation of my poor cock now, which felt heavenly as she languidly licked up and down, at one point putting both of my full balls into her mouth and swirling her tongue like mad! I felt like I would blow my load if her mouth swallowed my cock again, but somehow this did not happen and she actually did begin to suck me off again but this time gripping my heavy sac in her hands tightly! Fuck fuck fuck that was a mean thing to do, she knew how full my balls were as she sucked me good! She took me so Goddamn close to the edge I would have sworn I was already cumming and blowing a load into her mouth, but she backed off just in time. My cock twitched. And twitched. It was almost mimicking the muscular responses of an orgasm, but the lack of super intense pleasure is the way I quickly knew that I had not in fact blown it so to speak. She wrapped up the hot and heavy part of giving me head, and I sadly felt her lips completely withdraw, although I still had the wonderful tight warm feeling of her hand cupping my balls still. My entire center craved physical touch, anywhere, from her mouth, her hand, whatever part of her body, I just needed it between my legs! It was such a hard pill to swallow when the blowjob ended without me releasing that pressure whatsoever, my cock was dribbling a steady stream of precum, but no orgasm was given to me yet! And I knew I had hours to wait, and I was very afraid of what she could possibly have in store for me that evening. I knew I had to wait until tonight to cum, and it was only 4 PM!
Oh, it was so hard to get dressed after that! My cock was a leaking mess in my underwear now, and then my jeans on and the bulge in my pants still making it very hard to even zip and button my jeans. And putting on my shirt further took me away from the brink of cumming, being fully dressed now I felt so far, far away from that sweet fucking release I needed needed needed NOW!
As much as I love Sharona, a primal part of my brain hated what she was putting me through, as she took my hand and told me we were going for a walk, to cool me off. I was so worried someone would see how erect I was through my jeans as we walked out the front door of our house and took a leisurely stroll around my neighborhood, hoping not to run into any neighbors who wanted to make small talk. Sharona held my hand, it felt so innocent and cute, and to anyone watching we must have looked like just a happy couple going for a walk on a warm spring afternoon. What would people think if they knew I was under the spell of a cruel woman who was locking up my need for orgasmic release for days, and that I had only myself to blame for allowing it? My erection was not subsiding, and I just prayed it wouldn't be as noticeable as I feared it might be. I got even more aroused when she squeezed my hand. She stopped, and then titled her head up, and just...kissed my left earlobe. Hot breathing in my ear. She didn't say a word, she just used her mouth and tongue on my earlobe in primal sexy ways that set my cock on fire even more if that was possible. Of course it was possible, I thought, she had kept escalating the arousal more and more already, and I knew she wasn't nearly done with me yet!
We got back from the walk and didn't do much for a few hours. I was just waiting for it to get dark, knowing I was getting closer to the moment I would be allowed to have my orgasm. We had a nice dinner of leftover take-out Italian food from the previous night, and I watched a bit of ESPN, not really paying attention to the topic or even what sport they were talking about, my mind was so focused on horniness.
A few hours later, after a somewhat relaxing afternoon and evening, I looked at the clock. 10 O'clock. This teasing had gone on long enough, I thought, frustrated beyond belief already from over 36 hours of not having an orgasm, but being cruelly teased. "It's night time Sharona, I made it, oh God I just need to fuck you so bad!" I spoke.
She smirked and said "I told you there would be three challenges. We are now arriving at the third challenge dear. After that we will be near the point that you can't wait to get to.
Jesus Christ, what did she have in store for me? "Strip!" she suddenly ordered. Still a bit shocked at her aggressive behavior today, I quickly obeyed her and stood two feet away from her, stark naked while she was fully dressed still, wearing a long red skirt, and a black blouse. She snuggled up to me and drove me crazy, kissing my mouth. It felt odd to be fully naked but pressed against her skirt and blouse. It felt like she had no bra on underneath her top, which I loved. I looked and I could see her nipples. Her long red skirt was brushing against my cock and legs. Then she lifted her skirt up and I instantly felt her wet cunt brush up against the head of my cock! I was so ready to fuck her brains out. She took the initiative, and with her hand, she slowly guided my cock into herself, still wearing the red skirt, it was just moved up over her waist...I was inside her and it felt even better than usual after all this edging and teasing.
CHALLENGE THREE: THE CRUELEST SEXUAL INTERCOURSE EVER.
"Just sit still and let me move" she said as she rolled me over and put her weight on top of me. I reached under her soft black blouse, and cupped both of her tits. They are a bit smaller than average, a nice handful that felt so good in my hands. She got my whole entire cock inside her pussy and I bucked my hips up. She completely stopped moving, and moved my hands off her tits. "NO MOVING! SIT STILL NOW!" I did my best to calm my hips, and she sat still on top of me. She removed her top as I watched, mesmerized by the sight of her bared breasts. The skirt remained on her as she began to grind on me.
"OK lover, you already probably hate me so much. But here is your final challenge -- I want to cum right on your cock, and you are not to cum until after we fuck. Got it?"
"No way! I can't possibly do that; my cock is about ready right this instant!" I strongly protested.
"Yes, you fucking can Zane! So close, don't deny me this, I want you to complete the final challenge!" she yelled. She wasn't yelling out of anger -- the tone of her scream was obviously one of arousal, but it was a jolt to hear anyway, coming from my girlfriend who was normally not at all this demanding. "Here is the plan, I KNOW you can do it if you really try. It would be so wild for me to cum right on your cock when you are this horny. I'll make it as easy as possible -- I will do all the moving myself, you just sit as still as possible, and I will touch myself and cum as quickly as possible.
Fuck, fuck, FUCK! I wanted to cum so badly, this was torture. This was SO CRUEL! I suppose that was part of the fun for her, but she had no idea how hard it was for me to hold back a gusher of two days of built up cum when I was this aroused. I closed my eyes and then...I felt it, her wet cunt was sliding its way down my cock, and then I was all the way in, trying to sit still, and finding the sensation infuriating, not being able to just cum while she fucked me. But I was a good boy, and she did keep her word about trying to cum fast, so this wasn't too prolonged. I made the mistake of opening my eyes though, and watching her furiously rubbing her clit kicked up my arousal even more, somehow, and I didn't know if I could make it through her actual orgasm on my cock when I wasn't even allowed to cum myself! But I gritted my teeth....and felt her pussy muscles grip my cock, she clenched my cock tightly, and with no warning. This was the most difficult phase of the challenge, by far, because while I was denied, I had to feel, see, and hear her orgasm, right on my fucking cock! She dripped sweat down her little titties, and her nipples looked beautiful and perky, as she tilted her head back and let out a primal scream of sexual satisfaction. She spared me the full brunt of the wonderful clenching sensation that was making my cock about to explode beyond my control, and then she dismounted me, and thrashed her hips on the bed. I moved away from her body, as skin on skin contact would have probably made me cum even if my cock was not touched.
She came down and I looked into her eyes, and I began to stroke myself, seconds from shooting a load all over her body as she lay there in bliss. She looked at the clock. It was 11:18 P.M.
"STOP!" she yelled, startling me in mid stroke.
"Oh c'mon!" I protested, slamming the brakes on my hand motion.
"It isn't midnight yet!" She said.
"We never set a time, you just said tonight I could cum! Argh, please, I really can't bear this, my cock and balls are aching, and the thought of not cumming, I need to cum so soon, please, please, please?" I pleaded.
"Mmm...I love the begging, Zane!" she smiled. "Ok, fair enough, so I will give you these two choices: One, you can cum right now, or two, you wait until midnight...and you can do the same thing to me next weekend! Tease the Hell out of me, make me goon like a mindless slut, make my pussy a wet mess for 48 hours and not allow me to cum for two entire days! If anything, think of it as...revenge?"
My mind raced through the choices. I glanced at the clock. 11:23, so if I could make it through 37 minutes of just doing nothing, I would be able to turn the tables, and make her suffer like I was right now! I relished the thought of making her read erotic stories, and edge herself silly, and many other fiendish ideas I had for "Challenges" for her in this scenario. Cum now, or suffer through just a bit longer?
And the thirst for revenge just BARELY edged out the urgent throbbing need to CUM RIGHT THIS INSTANT! Just barely, this was the closet margin possible, and my snap decision could have easily gone the other way in my head. I wanted her to go through this Hell herself, get a taste of her own medicine, and I planned to be absolutely merciless, and...cruel even, as she had been to me! SO CRUEL!
"OK! As long as you promise to not tease me whatsoever until midnight Sharona, and then oh your next weekend is going to be rough!"
"Deal!" she said. She was about to shake my hand, both of us lying in bed together, me still naked, her in the red skirt and topless, but then she withdrew her hand, and said "I don't want to touch you, that might break the rules about teasing and turning you on more, dear!" She smiled. And to her credit, she did honor her word about not teasing me. I walked out of the room and actually got dressed in my boxers and t-shirt, and went outside the back door to our yard to get some fresh air...and hopefully cool off enough to restrain my libido for just about another half hour.
I paced back and forth a lot, that last half hour felt a lot longer than it actually was. But then one moment I happened to glance at the clock and saw it was 12:02 A.M!
I wasted no time. I didn't even try to make it to the bedroom, we were both in the living room. I ripped off my shirt, pulled down my boxers, and embraced her. I remembered that she had originally wanted to see the visual aspect of me shooting out a huge load of cum after all this edging, but I decided that fucking her brains out was the only thing that would do. She was still wearing just the skirt from earlier, the skirt I had fucked her in and also still topless, sitting on the living room sofa. I didn't even say a word, I just rolled her completely onto her back, and the I got on top of her to finish this off missionary style! I pumped away. I thought I would cum immediately, but I made it a good 2 or 3 minutes, enjoying just fucking the crap out of her, nailing her good, biting her shoulder a bit, my hands gripping her ass cheeks as I fucked away util I finally hit the sweet, beautiful point of no return, no stopping this gusher now!
And BOOM! It hit me. I could try to describe it to you, but you know what an orgasm feels like. So just imagine that feeling, multiply it by 3, and imagine that the feeling you normally feel most intensely in your cock when you orgasm is felt in every cell of your body as well. And the waves of pleasure just felt endless -- my mind could not even grasp when the end would be, it felt like the longest lasting involuntary spasms my cock had ever had. My eyes closed, I collapsed on top of her, still inside her, still quite hard, my cock still quivering. I have no idea what happened next to be honest, I think I must have blacked out when I was still inside her, and then I must have woken up some undetermined amount of time later, and I found myself naked on the sofa, with Sharona sitting on a chair 5 feet from the sofa, now dressed in a pair of purple silky pajamas that I knew were here favorite pajamas. She smiled at me, and I smiled back.
Part of my own smile turned into a smirk at the very end, because I had just thought of a really lovely, cruel, beautiful, evil, and sexy way to tease her next weekend...