I couldn’t stop thinking about Anna. Don’t ask me why.
All signs pointed to disaster, at least for me. First of all, I didn’t even think she’d give me a second look. I’m almost twenty years older than her, maybe two inches shorter than her, a belly, receding hairline, I’m married with kids…the list went on.
And of course, we worked together in the same office. I was considered her superior in the scheme of things, even though we were in different departments, so any move by me could be seen as harassment.
Unless she was interested too?
To look at her, you would probably wonder why I was so taken by her. Her hips are a bit too big (by “magazine” beauty standards), and so is her butt, she has a mouth on her like a longshoreman, and she’s a smoker, which is usually a big turn-off for me. She’s a single mom too. Not a classic beauty and not the usual target of extra-marital affections, but let me stop my story right here and say that I don’t think I am that shallow. Beauty is in the eye of the beholder, right? What about inner beauty?
I really never sat down and analyzed her, detail by detail, to find out what was wrong, or even what was right about her. She was just plain old Anna, and I was just plain old me. I’m nothing special either.
But whatever it was, I couldn’t get her out of my mind. Over time, we developed a pretty good level of communication, sometimes just talking for the sake of talking, looking at each other’s Facebook pictures (and adding each other as friends), and just getting to know each other a bit better. Nothing more than that.
Until the time she turned her head a funny way while sitting at her desk. It was after hours and she was working a bit of overtime, and I came over to her workstation and was just talking. And then she did it. She bent her neck to the left in an awkward or jerky kind of way. Tilting her head to the left. And then she did it again.
“What’s the matter?” I asked.
“Been typing too long. My neck is stiff.”
“You probably could use a good massage at the end of the day.”
“Right, and where am I going to get one I can afford?” she responded.
I walked behind her and touched the back of her neck gently. “Is this where you feel it?” I asked.
“A bit lower. Closer to my shoulders,” was the response as she leaned back in her chair.
I took this as her invitation for me to give it a try, if I wanted. So I did. Massaging her shoulders, her neck, moving down between her shoulder blades, and then down the upper part of her arms too.
She closed her eyes as I continued rubbing her, kneading her flesh to try to work out the tension and the kinks. She was wearing a rather loose sweater, and as I rubbed her neck I was able to slide my hands under the sweater to reach the upper part of her shoulders right on her skin.
“That feels good,” was all she said after about ten minutes of her massage.
I moved forward a bit and began to massage her collar bone, and then the upper part of her chest, still far enough away from the top of her breasts to be considered safe and not too presumptuous. I gently played with her skin and rubbed her softly, my hands gradually moving down until I could feel the first traces of that fleshy and bouncy slope that would lead down to her full breasts. My hands brushed against her bra straps as I continued my massage, and as my hands gradually kneaded the upper slopes of her breasts.
My fingers penetrated lower into her sweater, as the palms of my hands safely massaged her higher up. I could feel the softness of her luscious breasts at the bottom of my fingertips, and there was no way she was unaware of the slow descent of massaging hands.
She was completely aware, in fact, as she suddenly grabbed both of my arms and pulled them down so that my hands reached directly onto her breasts, over her bra.
“That’s where I want your hands,” she said. “Get to work.”
I massaged her breasts over her bra, rubbing the palms of my hands over the buds of her nipples pushing against the fabric.
“Inside the bra…I want to feel your hands on my tits,” she added.
I slid my hands inside her bra and felt the most luscious breasts imaginable. They were full and very soft, pliant and yet well-formed, and her nipples were thick and round, like small marshmallows atop her breasts. I cupped her breasts and caressed them, and continued to rub her nipples with my palms, occasionally finding her nipples with my fingers and pulling gently on them, or flicking them with my fingers. Then I would trace circles around her nipples with my fingers, before beginning to rub them again with my palms.
In a swift motion, she lifted my hands out of her bra and sweater, and then she pulled her sweater off herself, and turned around in her swivel chair facing me. She undid her bra and let it fall to the ground, leaving me face to face with two perfectly beautiful breasts, her nipples pointing at me, a brownish red that complemented her olive skin.
“Your mouth would feel so good on my tits now,” she said, almost begging in a whisper. “I’ll give you a hint…on a one to ten scale of how rough I like it with my tits, I’d suggest an eleven. I like to be bitten too, not just sucked and licked. No blood drawn, but I like teeth.”
How could I not comply? I was already hard inside my pants, and she must have seen my cock pushing against the material as I stood in front of her. I knelt down and took her left breast in my mouth and began to lick around her nipples, in circles and then take the nipple in my mouth and swirl it around inside with my tongue as I sucked hard. Then a bite. Gently at first, but she pulled my head in closer to her and said “Harder” as I then took another nibble, holding her erect nipple firmly between my teeth.
As I did this she reached down and found my belt buckle, which she then undid, and all the while, as I played with her breasts with my mouth, she opened my pants and pushed them down below my waist, leaving me only in my boxers kneeling in front of her. She reached down and put her hand inside my boxers and found my cock and began to play with the tip with her fingers, more tickling than stroking.
She pushed me up away from her breasts and gestured for me to stand up. As I did, she pushed my boxers down so that my cock stood straight up in the air in front of her face, as she was still sitting in her chair. She leaned forward and took me in her mouth, first sucking on the head in short strong pulses, and then enveloping my entire shaft inside her mouth, using her tongue to stroke me up and down inside her mouth. Her mouth felt like a vacuum cleaner, she was sucking so hard on me, and it felt incredible. While she sucked me, she played with my balls.
I’ve always been a little unsure about blowjobs, because sometimes they feel too intense and I feel like I’m going to lose control. This time, Anna’s mouth was completely in control of me, and I felt such incredible things as she sucked me, and it was probably the first blowjob I ever had that I completely enjoyed. Her mouth was like silk against my cock, but her grip on me was like steel, sucking hard and steadily.
Then she took me out of her mouth and started jacking me off.
“You’re going to cum on my tits, and then you’re going to lick if off my tits.”
So I stood and steadied myself by leaning on her shoulder with one hand, as she jacked me hard and fast. I could feel my climax approaching, and I think she could too, since she started jacking me even faster with a vengeance. I screamed out “I’m cumming,” just as the first shots of cum erupted from the head of my cock, onto her lovely breasts, dripping down across her nipples and some onto her belly.
“You know what to do now,” she said, and I immediately bent over and started to lick my own cum off of her tits.
“Swallow it too,” she added, “it really makes me fucking hot to watch a guy eat his own cum.”
I obeyed. I had tasted my cum many times before without thinking twice about it, but somehow it seemed a bit naughty and daring this time with Anna.
I laughed. I don’t know why, but I laughed, maybe more like a giggle. Anna looked up at my face, as I stood there with my cock still hard even after cumming, and with her naked breasts in front of me.
“One last thing,” she said, as I let out another laugh. With that she pulled me closer to her and reached behind me, and with her left hand she spread my ass apart and shoved her middle finger right up my ass, deep to her knuckle, and with her right hand she grabbed my cock and took me back in her mouth. I nearly fainted from the sensation of having her finger up my ass while she sucked me hard again. I hardly lasted two minutes before I shot another load, this time into her mouth as she continued sucking my cock and playing with my balls, while fingering my ass with her other hand.
“I feel so much more relaxed after that massage,” she said while smiling at me. “How do you feel?”
I couldn’t answer. I was breathing too heavily and couldn’t get a single word out. My head was spinning and I felt close to falling over.
“Don’t get any weird ideas,” Anna said to me, as she wiggled her finger inside my ass. “This has nothing to do with love or anything like that. We work together and I am not your girlfriend. This isn’t even an official affair as far as I am concerned. We work together and occasionally we can provide massage services to each other. Got it?”
I nodded my head “yes” and before I could speak, she continued.
“Today my neck and upper body were bothering me. I have a feeling that the next time I work late, I might get a bit stiff in my lower half from sitting too long. Do you know how to massage me there if I need it?”
“I think so,” I answered.
“Good,” she said. “Don’t forget to bring a condom. I’m not on the pill, and neither of us needs a surprise in nine months. Actually, bring several condoms…I have some ideas about a couple of different kinds of massage I might need. A hint…I also like it up the ass too, and not just your finger. And I’ll clean up too, so don’t be afraid to rim me. Got it?”
“Good. Now before we leave I want to see you jack off for me, while I finger fuck your ass some more. I want you to cum on my tits again and then rub your cum all over my skin with your cock. Then we’ll clean up and head out. You’ll give me a lift home, right?”
I was beginning to see what I saw in her all along, why I couldn’t stop thinking about her. She knew exactly what she wanted and nothing more and nothing less.
And I knew what I wanted now too. I thought about what I wanted as I jacked off one last time, feeling her finger in my ass and as I came one more time on her breasts.
“Nice shot,” she said, looking at me again with a smile. “Nice shot.”
I knew exactly what I wanted, and that was to see her smile again and again.
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