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I confess that I just got a handjob at work from my middle-aged supervisor, Elaine. I work in a tiny office with just the head boss, my supervisor, and one other employee most days. The head boss and the other guy were both out yesterday, so Elaine and I were alone. I'm a tall, slightly chubby guy in my mid 20s. Elaine is short and petite, I'd guess in her early 50s, with long blonde hair that's turning pale white. She's fit and looks really good, kinda like a shorter, slightly older version of this woman's body: http://i.penisbot.com/a/anilos-com/6394346/09.jpg She's been a huge fan of mine ever since I started this job. She really likes what I'm doing professionally, and we've clicked well on a personal level. We grabbed dinner once after work a few weeks ago - which was her idea, in retrospect - but I figured that she wanted to hang out. Elaine is married, but her husband spends a lot of the time outside the country. I'm pretty oblivious about women, and since she was so much older and married, I wasn't even thinking about her sexually. Things started getting interesting when I stumbled into her yesterday. I lost my balance a bit while trying to put something on a high shelf and backstepped right into her. Elaine was facing me, and her arms went around my waist like she was on autopilot. Her hands definitely brushed my junk, and she leaned in a bit against my back. I froze, and she stayed there like that for several seconds, basically holding me. I was just embarrassed at first, but when I started moving away, she had turned bright pink and was stammering an apology. Elaine is normally very composed, so I knew something was different. We went out for lunch together, which was also unusual, and chatted a bunch. The conversation came around to her husband, who's been gone for two months and won't be back for another six weeks. She laughingly talked about feeling lonely, but she kept blushing when we made eye contact. Okay, now I know what's up - there's oblivious about women, and then there's braindead. I wrestle with my conscience all afternoon about her husband, and decide to just go for it. Maybe not the right call, but I was horny and I have no regrets (yet). I started stepping up the physical contact to gauge Elaine's interest - little things, like putting my hand on her shoulder to get her attention instead of calling across the room. She responded really positively, and when I started putting little intimate touches in (like softly massaging her shoulder instead of just touching it), she practically purred. At the very end of the day, Elaine went around to turn off unused computers, and "accidentally" stumbled into me. There was no way she did it by accident - she was way out of her way to even stand near me. She slid along my chest so that her back was against my torso, and leaned in, still feigning that it was just a stumble. With alpha instincts I've never displayed before, and may never display again, I just went for it. I put my arms around her sides, resting on her hips. Elaine's head doesn't even reach my shoulders, so I was easily able to bend my neck and press my lips against the crown of her head. She froze. And then, just as I started to wonder if I'd fucked up, she purposefully leaned back into me and started ever-so-gently grinding her hips against my crotch. I ran my hands up and down her thighs, and after a few moments I started playing with the edge of her blouse, running my fingers up inside to touch her skin. Elaine was grinding more quickly, moving more of her body. We did this little dance for about a minute, and then she placed her hands over mine, holding them onto her body. Elaine held them onto her as she turned around to face me, and then she leaned in to kiss me. We made out for about ten minutes, I think, and it kept getting dirtier. It's like she broke some sort of mental dam and a flood of nymphomania got released. She was sucking on my neck, pinching my nipples, and making these adorable squeak-moan sounds when I touched something good. My hands were all over her - under her shirt, feeling her breasts, grabbing her ass, pulling her hair. She really got turned on when I was playing with her hair, which I intend to remember. At some point I hooked one of the armless rolling chairs with my foot and dragged it over. I sat down, and pulled Elaine to sit in my lap. She shimmied out of my hold and instead straddled my right leg. She leaned in to kiss me again, but this time I could feel her grinding her pussy on my thigh. We were both panting by this point, and I was just thrilled to take whatever she wanted to give me. When I felt her start grabbing for my fly, I was about ready to sing hosannas. My dick was like a steel rod at this point, and I KNOW she'd felt it. She spoke for the first time in this whole little adventure and told me to lean back and close my eyes. I did, and I felt her unbuckle my pants, unzip my fly, and pull my cock out of my underwear. Her hands were tiny and soft, and my dick was twitching constantly. She made a pleased humm-purr sound, which may be the sexiest thing I've heard in my entire life. There's nothing like a woman who's genuinely happy to see your dick. Then I heard her spit. I opened my eyes to see that she'd just spat into her hand. She met my eyes and, without breaking eye contact, grabbed my cock and started giving me a handjob. It was a damn good handjob - not the absolute best I've ever gotten, but definitely the best overall experience. It was in the office, with an older woman, and she seemed to be getting off on it so much. Elaine started grinding on my leg again and was moaning in chorus with me. After five or six minutes of this, I was ready to pop, and I told her so. She just smiled devilishly and leaned into my chest again, kissing my neck and playing her free hand around my chest. The extra stimulus was too much and I came. She'd moved so that nothing would hit her, and I got a good four or five long jets of cum all across the office carpet. We kissed again for a few minutes, and then just hugged for a bit, still in basically the same position. She seemed to like playing with my cock when it was limp, and that just made me start to get hard again. She laughed at that and put my dick away for me. We had part one of the serious conversation beside my car in the parking lot. Elaine's husband apparently has side flings on his trips all the time. He doesn't think she knows. She doesn't mind too much, but takes it as an excuse to have some on the side when SHE wants to. That's an arrangement I can live with, ethically. She had turned shy again and kinda stammered when I asked if this was going to be a one-time thing, but she's definitely down for more. We texted throughout last night, and she's pretty kinky. She wants me to get tested before we do anything else, and promised that she'd do the same. She said she hates condoms, and since she isn't fertile anymore she wants to do everything without protection. (WIN WIN WIN WIN WIN) I'm going to set up an appointment for that STD test as soon as possible. With any luck, I'll be balls-deep in MILF next week.
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