A few years ago, my ex and I were breaking up. It was an amicable split so we ended up doing what many couples in this same situation do when coming to the end of the relationship, we had sex one last time. Although this time it wasn’t full intercourse. It was more of a playful fondling and mutual masturbation, at least at first.
Since this was going to be our last time being sexual together, I wanted to give her something that she would remember. I pulled out every technique in my bag of tricks and focused completely on her needs. For about 40 minutes I played, rubbed, teased and massaged her way through many orgasms before she was totally spent.
After a few minutes of catching her breath, she began to focus on me.. and this is where the fun really started…
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Killing the pleasure
When she grabbed me, I could tell that something was a bit different. In her post-orgasmic clarity, my pleasure had seemed to turn into a job that she wanted to get over with and was taking no pleasure in doing. She was rough and uncaring with her handjob. As her hand wrapped tightly around my shaft, she would repeatedly squeeze it as hard as she could, and then would let go. I was convinced that she was doing it just to see how red she could get my head to turn. It hurt a little but also felt oddly erotic because she had never done anything like this before to me.
Once my head was the proper shade of reddish-purple that she was going for, she started to alternate between teasing me and then ruining that tease… With my shaft held firmly in one hand, she would use her other hand to gently rub my head. As I felt myself starting to sink into the pleasure, she would then playfully pinch or flick my head just hard enough to bring me sharply out of that pleasure zone.
I didn’t know what to do. It felt good and it was maddening at the same time, but I found myself getting very turned on by what she was doing. I wasn’t sure if it was because I liked the pleasure and pain combination or if it was simply because it was different than anything I had experienced before.
When she was finished toying with my head, she began to move her hand along the entire length of my shaft in long and slow strokes. I can feel my body starting to relax again and begin to enjoy the feeling of her soft hands on me. I closed my eyes and let the total enjoyment start to take over. She continued to stroke me just long enough for me to let out my first moan of pleasure. Then she changed the pace and rhythm. With my shaft held firmly in her grasp, she started to slowly give more emphasis to the down strokes. It took a number of attempts before I realized what she might be doing. It was almost as if she was aiming her hand for my balls as she brought her hand down to the base of my shaft.
Time to add some pain to the mix
I began to feel the side of her pinky finger lightly brush against the top of my balls. Not every time, but just frequent enough to keep me from fully entering that sweet spot of enjoyment again. At first, it was very light and playful, and it actually felt good in a weird sort of way, but the impacts gradually became more and more forceful. I started to get a little worried about her hurting me, accidental or otherwise. It doesn’t take much to double a guy over when he takes a wrong hit down there.
I suddenly felt my body involuntarily react to one of the hard strokes. This one hurt a little. I felt the dull pain in my lower abdomen that usually accompanies a strike to the balls, starts almost immediately. I grimaced and let out a small painful moan. She countered my reaction by quickening her stroking pace bringing my body from pain to pleasure.
Just as I felt myself start to relax again, a second firm blow came down on my balls. This one was just as hard as the last. Although comparatively speaking it was about the same amount of pressure one would use patting an infant on the back. playful, yet firm… I could feel the abdomen pain start to return. My body again jerked in reaction, and again she quickened her stroking pace, reluctantly dragging me back over the line from pain to pleasure.
My inner turmoil was really starting to set in at this point. I didn’t know if I still wanted to have an orgasm or get up and run. Each impact hurt, but it also felt wildly erotic. Was she deliberately trying to take some aggression out on me and hurt me? Or was she just pulling out all of the stops and experimenting or doing something that she always wanted to do? I Was debating on what my next move should be when the third blow came down.
Again, my body reacted to the initial jolt. Ok, I had enough. I have to say something. My mouth opened, but all I managed to say were the words ‘I don’t think..’ when she leaned over and took my head into her mouth and started to suck me. I was instantly distracted and I had all but forgotten about the pain I was feeling. She slowed down and took her time, giving me a few wet licks and playful long sucks. Then she went back to stroking me again.
I instinctively spread my legs, not because I liked the sensation and wanted more, but I was hoping to give my balls a little space to drop down and out of striking distance… big mistake… She seized the opportunity, almost as if she was waiting for me to do that. She cupped my balls with her other hand and lifted them back up, even higher than they were before and then continued her stroking and playful abuse to my balls, except now they were trapped between her hands
I didn’t know what to do or how to react. It hurt, and it felt amazing at the same time. At this point I was scared to say anything to her, after all, she quite literally had my balls in her hands and obviously didn’t have any issues roughing them up a bit. I felt like my body was simply there for her amusement and not my pleasure.
This is when something began to happen that up until now was a completely foreign thought to me. Somewhere between my pleasure and pain, I could feel my orgasm beginning to stir. She was stroking me at a good pace while her other hand was working my balls, squeezing and pulling them and every so often giving my body another jolt when her hands came together.
Here comes the big ruined O
I didn’t know what to do… Should I say something? Should I tell her that I was going to cum? I was afraid of what she would do if I told her, but it felt too good to tell her to stop. I was quickly approaching the point of no return, I had to make a decision before my indecision chose for me.. I blurted out.. ‘I’m going to cum!’.. she then sped up, her strokes grew faster and harder… the impact to my balls grew more frequent and they were aching from the pain… and also aching for release… she brought me right to the brink of explosion… and just as my orgasm began to take over, she let go of my shaft gave my balls one last long and hard squeeze… The sound that I made was a questionable groan.. as if to say “Why did you stop!!?”…My pleasure and pain were milliseconds from colliding together when she looked me right in the eyes as I started to explode all over myself and simply said ‘Just let it happen..’.
I couldn’t stop myself from cumming. My balls were in pain but I was in the midst of having the most intense, yet strangely unfulfilling orgasm that I ever had. I felt my cum start landing on my stomach and chest as my cock had begun uncontrollably launching one long stream after another. I don’t think I have ever expelled that much in a single orgasm… I’m not sure if it was my body that pushed out all of that cum or if it was her squeezing it out of my balls… I wanted to grab my pulsing shaft thinking that I could still get in a few good strokes to get the fulfillment that I needed, but it was too late the orgasm was ruined…
Post orgasm torture
Just as my cock had finished pumping its last drop, she grabbed my shaft again and began to rub my head with a newly found conviction. I started to squirm… She knows that Once I have my orgasm, that continued stimulation is uncomfortable, if not downright painful for me… But she didn’t seem to care. As I brought my hands up to stop her, she shifted her position and weight so she was now laying across me, with her back facing me. My head, still covered in cum, made for the perfect self-lubricant, and she took full advantage.. she kept rubbing.. I kept squirming.. The harder I tried to pull her off, the more pressure and speed she applied, sapping my focus and strength. The sensation was driving me crazy. the pressure, the pain, the over stimulation… I made one last push to get her off, when I felt her hand come down to dish out another firm pat to my balls.
Oh God, it hurt so bad… and I felt like I was going to cum again. I squirmed, she rubbed… I tried to stop her, she hit my balls… I moaned, pleading with her to stop. She answered by reapplying that grip to my balls with one hand and began stroking me with the other. The uncomfortable feeling intensified and I felt as if my head and balls were going to explode from pain.. or another orgasm. I couldn’t believe it, she was going to make me cum again. A quick thought flashed through my mind before the pain drove it away… I made her cum 5 or 6 times, I hope she wasn’t planning the same for me!
I couldn’t take it anymore.. between my pleasurable moans and painful groans, I managed to tell her that I Was about to cum again… And then.. nothing… She stopped. She stopped stroking me. She stopped squeezing and patting my balls, she stopped all stimulation altogether… I could hear my heart thumping in my hears.. I was confused.. Was this a tease? Was she done? “What are you doing??” I asked, almost out of breath… “You only get one”, was her reply.
My mind felt like it was going to explode! I had all of these intense feelings that needed some kind of conclusion, yet she just denied me…. She continued to lay across me until I went soft again. It was probably only a few minutes, but it felt like hours.. my muscles ached and I had a huge sense that she was wanting to prolong the Pain, pressure, and frustration that I was feeling. She seemed to savor it.
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When she was done, she released my balls, which amid my confusion, I hadn’t realized were still firmly in her grip. She simply got up, got dressed and walked out… Leaving me covered in my own cum and thinking … What the hell just happened to me?
Last Updated on 2 years by pseudonymous