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I’m a firm believer in the surprise handjob. Not knowing it’s coming is pure bliss. It can truly make a day or night eons better. But the best handjob I ever got was far from a surprise, although it was my first handjob from this particular girl. I learned a lot from my best handjob experience, mainly those good things come to those who wait.
A few years ago, I was in a relationship. Susan, as we shall call her, eventually parted ways with me after a year. I get it, a year isn’t a lifetime, but I’m 25 years of age, so it felt exactly like a lifetime.
She wasn’t the best girlfriend. She was convenient in her own way. And I was convenient for her. We were bored and had a desire to party at bars.
She gave me good blowjobs, but only while drunk. She hated cum in her mouth sober. Actually, she hated dick in her mouth sober. But one day, she gave me a handjob during the day and I ended up telling her that her handjob was better than her blowjob .
At first, she was somewhat offended. And rightfully so, because it sounded bad. But her emotions were tempered by her inner-opportunist. She didn’t love giving blowjobs while sober during the day, so it was a win for her.
But still, that wasn’t what I meant. I wasn’t really saying I hated her blowjobs, in fact, I loved them. But when you are always drunk during them, it’s not as fun. That said, my point was more that I loved the handjob a ton. My statement was a reflection on my surprise, rekindled love of the glorious handjob.
Not only was her handjob technique nutty good, but also, it felt like a pity handjob . Oh boy, now things are gonna get weird. But hey, this is anonymous handjob confessions, I’m allowed to let my freak flag fly.
Just before it happened, I got all up on her. I had the hangover hornies. My dick was a rock. I was fantasizing about face fucking her on the couch. I was certain I probably couldn’t pull that off.
As I began to adjust my hips front and center on her, she slid her hand into my jeans and began rubbing me. My jeans were fully buttoned, my belt tight, so it was rough for a minute. But I laid back into the couch. The less I touched her, the more she interacted with the handjob.
But this time, things were different. She began to open my pants up.
I shuffled my hips to remove both my pants and underwear in fast order. While my pants were hitting the floor, I meandered my feet from my underwear while removing my shirt. I expected a cum fest, so I wanted it on my stomach. Plus, I didn’t want the t-shirt obstructing her hand.
Now, I’m not going to lie, I was holding out hope for a rare sober blowjob. But her head wasn’t even fidgeting that direction. She had this long brown hair, it was straight but glowing, that fell across her upper shoulders and draped over the upper section of her cleavage. Susan didn’t have huge tits, but she was young and made the best of bra/shirt selection.
I was on her left, so she was using her left hand to erotically feather finger my dick and balls. She’d never done that. I knew this handjob was lining up to be a better experience.
I mentioned earlier that this became a pity handjob. You can read about pity handjobs here if you need, but just know this, they are what they say they are.
It’s when a girl, typically a friend, gives you a handjob out of pity. Maybe you are down on your luck sexually.
It could be a girlfriend, as was the case with me, that feels bad for how hard your dick is.
While Susan was fondling my dick and balls, I was unaware that a great handjob was in my future. I decided to put all my money on red and go for it all.
So, I nudged her head towards my hard dick. Simultaneously, I thrust my hips up a little. It was a transparent blowjob play. She was fully clothed, I was wearing nothing. It was sunny outside, the TV was on, it was so chill. I just wanted to cum in her mouth so bad. Hangover blowjobs are great, but with Susan, I never got them.
“I can’t do that. I’m too hungover. I’ll gag.” Susan said.
The air didn’t fully fly from my sails because she kept her hand engaged with my extremely hard cock. The head nudge is a risk. She could have gotten offended and told me to pound sand. My cum was moments from flying into a bathtub, but instead, the direction remained good.
“Look, I want to give you a pity handjob. And I promise it will be the best handjob you’ve ever had.” Susan said, looking me right in the eyes in a way she never had. There was loads of intent in her eyes, I was captivated.
The best handjob I’ve ever had? Really? This sounded enticing. On a hangover day, Susan sure was sexually and erotically lively.
“OK, but a pity handjob? I don’t get it?” I said.
“So, my friend apparently gave her guy friend what’s called a pity handjob. Basically, its where a guy is so desperate to cum with a girl, you take pity on him and jerk him off. I found it hot.” She replied.
It then became obvious to me. Susan was totally into this pity handjob mindset. It turned her on to hold so much power. It was sort of this BDSM play, but not fully there because I’d most definitely never be in pain and always be in total ecstasy. It was as if she was skirting around the Femdom thing , but not kicking me in the balls, if that makes sense.
But to her, the pity handjob represented a power play. It turned her on.
So it isn’t as if it hadn’t already begun. Her hand had been floating and caressing my balls and dick. I’d tried to push for a last-minute blowjob.
But the actual best handjob ever? That began now.
She was totally into things. More than she’d ever been before. Her blowjobs, even when drunk, were always rushed and she only sucked the tip. When I’d fuck her, she seemed to like it, but she also always seemed to want me to just cum at some point.
In this case, she was in full control. Making eye contact. Telling me erotic things.
“Its so built up. I’ve let you down. I’m going to make you explode with cum.”
Moreover, she was savvy in making sure to jerk me at a speed that kept me heightened but didn’t make me fully cum. I got close at times, but she’d pull back. It was super tantric.
“I’ve watched some handjob porn .” She whispered.
I couldn’t tell if she was serious. I was so in Ecstacy, yet perplexed, all at once. I just didn’t care if she was lying.
She reached into her purse and pulled out a bottle of lotion. She squeezed it all over my dick and balls. If you know anything about lotion handjobs , you can imagine my incredible excitement already.
She spent at least 5 full minutes massaging it in, while pouring moreover my dick and balls, and into her hand. She even lathered up her wrist so that when it brushed by dick while she was massaging my balls, it was lubed.
At that moment, I realized, I was the hardest I’d ever been. As she began jerking me off, she used a full grip. Her hand slid from the bottom of my dick to over the top.
About 15 minutes into the handjob, I realize I was combustible and that I’d almost have to cum.
I gripped her inner-thigh super tight. With my left hand, I grabbed onto a throw pillow.
She increased speed, whispering, “Its OK to cum, I can’t wait to see it.”
I could feel the tip of my dick building more pressure than I’d ever experienced in my life. The lotion allowed her hand to slide up and down with complete control and amazing speed. All I could hear was the sound of her hand slapping down on my lower abdomen and lotion crackling.
And then, out of nowhere, as I realize the explosion was near, she lobbed her head down and put my balls into her mouth and pointed my dick straight up.
When the cum came, it was explosive. It shot feet into the air and landed everywhere. There was cum all over her wrist and streaming down her face as she had both of my balls in her mouth while her tongue twisted and turned.
The cum session lasted for what felt like a full minute. I would not stop cumming.
When it was over, she lifted her head and wiped some cum from her cheek. There was also lotion on her mouth.
She then licked up some of my cum from my stomach. The only time she’d ever swallowed my cum was during drunk blowjobs, now she was lapping it up like we were finishing up a porno shoot.
She never did that again. And I never completely understood what sparked the best handjob of my entire life to happen. Although, I had theories. Maybe she’d developed a freak fetish for the handjob and cum shot. Maybe it was through watching porn, or talking to a friend.
All I know is months after that, she left me. I fucked her a few more times following that. She gave me a drunken blowjob just a week before she bailed, I came on her face. She didn’t care.
What hurts me the most is realizing that some lucky sap out there is probably having the time of his life. She most likely didn’t feel totally comfortable being a freak with me because I was such a nice, romantic type.
She left me with a handjob addiction, however. I masturbate to handjobs. I’m lucky to have Handjob Hookup . It’s been my saving grace.
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