Handy Work

I'll never forget that first time my girlfriend Darlene caught me jerking off. It's something every guy lives in fear of I'm sure. I mean, we've all done it, and might even admit to having done it, although none of us wants to say we still do it while we're in a relationship. But whether I'm in a relationship or out, I still take time for me. No matter how much sex I'm getting I always crave a little more. Which is how she found me one wanton Wednesday morning.

"Oh my, what are you up to?" Darlene said, a broad grin lighting up her pretty face as she perched on the edge of our bed. Having surprised me, she laughed, enjoying my predicament. "Don't stop on my account. I've always wondered how you guys do it for yourselves, maybe you can give me some pointers. Left or right-handed, full fist or finger-tips?"

Even though her reaction was friendly, good-natured even, I felt positively mortified. I might have thought of pulling the covers over me and pretending this hadn't happened, but there was no denying she had caught me. And even though I felt drained of any feelings of arousal my penis stiffened reflexively, standing to attention, rigidly saluting Darlene's presence. She touched me, casually running a finger along the length of my penis.

"I'll bet you thought I was well on my way to work? Good thing I'd forgotten my lipstick and had to come back." She kissed the head of my penis and then my lips before grabbing her lipstick off the night table.

"Too bad I don't have time to watch you now, but we'll pick this up later. Depend on it. You know I can't let go of this." She fixed her lipstick, smiled and blew me a kiss. Before putting her lipstick away she traced a ruby streak along my penis and winked.

"That'll give you something you can enjoy washing off without feeling guilty. Try to think of me when you do."

I did think of her, moments later in the shower and throughout the rest of my day. At first I felt embarrassed, having been so careful never to get caught, but the more I allowed myself to be distracted by Darlene's reaction that morning the more relaxed I became. In the end, curiosity about the promised "later" and what she might have meant turned to arousal. By the time I saw her again that evening I eagerly anticipated the sort of ribbing Darlene would lay on me welcoming it as the prelude to some good dirty fun. She didn't disappoint me and we were soon rolling around naked on our couch.

Darlene would clutch at her full breasts and rub her pussy against my face encouraging me to touch myself as she looked over her shoulder to watch. She asked lots of questions, most of which I answered easily though I had trouble with telling her who I might think about when I jerk off. I figured she could handle the truth that I rarely if ever thought of her. After all, it's no fun fantasizing about the things you already have. Wisely, I avoided any mention of lusting after her two sisters, though when pressed, admitted a few of her friends had made it to my imaginary harem but refused to name which ones. When she complained I was being unfair in not revealing whom, I countered by saying I wouldn't want to know who, if any, of my friends might make a similar roll call for her.

This led us to a discussion with accompanying demonstrations of her own techniques in self-pleasure. Several times she interrupted herself to lubricate my swollen penis with her moistened fingers as an example of how jerking off together was making her so incredibly hot. I let her know how turned on I felt, nearing the brink and needing to slow down so we could both enjoy it longer.

"Yes", she said. "And you still have to show me how you do it for yourself so I can get better."

She swung herself around to sit behind me with her legs spread out, one on either side of me. She kept teasing herself with her left hand and slipped her right underneath mine so I could guide her fingers over my penis. The throbbing pleasure I had felt before her touch intensified, becoming a sweet, aching desire for release. I felt Darlene's breasts press against my back as she closed her cool, tiny fist around me.

"It's so hot." She breathed in my ear.

I shut my eyes and guided her hand in slow, steady strokes. She slid her slick breasts up and down my back and I wondered if the sweat between us was from me, her, or both of us?

"Bet your dream lover doesn't do this for you." Darlene cooed. "And does she taste this good?" She brushed her moist fingers across my lips.

Darlene started to moan softly and she began pumping me faster, her other hand sustaining a fast, grinding shiver on her pussy. My muscles tautened and I groaned loudly, certain she could feel my approaching orgasm boiling up from deep inside me struggling to burst free from her ever-tightening grip. My eyes snapped open in time to see the hot, sticky semen shoot out, flooding my belly and dribbling down over Darlene's still pumping fist. Her cheek pressed against mine as she avidly watched each successive spurt she could jerk and squeeze from me. The fingers on her other hand never stopped vibrating over her pussy as she coaxed her own climax to escape through clenched teeth in the form of plaintive cries followed by gasps and shrieks.

Finally we both collapsed in a sated, sweaty heap. Darlene ran her fingers over my belly rubbing and smearing the semen into my skin before making a show of licking her fingers off.

"Bet you'll think of me next time you do that for yourself." She said.

I agreed that I would definitely think of her, adding that from now on I might even be more inclined to do it when she was around to catch me.

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  1. I've only caught a guy once, but I think it's human nature to still masturbate in a relationship!

    (btw your links to WW are broken, pls fix?)

  2. Very hot. Nothing turns me on like watching a man stroke himself. The veins on his arm, the hard firm grip, lost in his own pleasure. God.

  3. Yummy! I know I love watching my guy jacking off...but I always get distracted/horny and want to 'help'. :P

  4. I love it when he cums over me....I agree with DDD, being made me watch...damn i am getting wet just thinking about it.

    Great post


  5. Wow! Have I under-estimated the turn-on factor women experience watching a guy jerk off? Apparently so.

  6. That's hot! I always wish I could catch my boyfriend in the act, but it's never happened.

  7. I walked in on my husband jerking it the other night. Hot hot hot. *swoon* Sadly he wouldn't finish for me so I took over. *grin*

  8. That is so damn hot! I have always wanted to catch Arthur but so far it hasn't happened. I'm still hopeful :)