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How I became a pillow princess pleaser
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This is a true story, an early sexual experience that set me onto a path where I love to pleasure women orally, often with no reciprocation.

Years ago, at my first job after college, I developed a flirtation with a woman who would visit the office I worked at. Not a co-worker, she was a contractor who came in for meetings a couple times a month. I wasn't directly involved in the meetings but I would end up seeing her around and I was just immediately taken with her. I'll call her Julie. Julie was absolutely magnificent - 5'6" of pure confidence and sexuality. Dark blonde hair, glowing blue eyes, smart as a whip. She had a gorgeous curvy body, I guess you would say a small BBW, and dressed to accentuate it - form-fitting clothes hugging her round ass and her big breasts. Julie was sexy and owned it. A lot of people took notice of her, but somehow she really picked up that I did. I would interact with her a bit and it wasn't long before she had me wrapped around her little finger. 

I was younger, in my early 20s, and Julie was in her late 30s or early 40s. And she worked for one of our most important clients. So there definitely was a power imbalance. It was a long tease starting with glances and then slowly her asking me for things, to get her a cup of coffee, to locate a specific file, etc. It wasn't totally out of my purview but definitely more appropriate for an office assistant (most of whom were women in that office, so I always found it interesting that Julie didn't ask them but always asked guys for stuff), but I didn't mind. Over the span of a year we got to know each other a little bit, she was flirty with lots of guys but seemed to take a special interest in me. Julie came to our office holiday party which was always a big bash. Nothing happened, but she was extra flirty with everyone, she somehow always managed to have packs of guys around her, there was lots of booze. I was having a good time but was still on the quieter side than most, and perhaps I was more obvious in my staring at her. We had a fun chat near the end of the evening where we were both pretty buzzed (although she definitely could hold her liquor) where she kept putting her hand on my arm, I think she was sussing me out. But that was it, she left on her own, and I went out later with a bunch of other colleagues.

To jump to the when things started heating up, one day maybe a month later, she came by my desk and asked me to show her where she could get some kind of office supply. I brought her to the supply room. When you went in, the door shut behind you automatically. She came up close and ran a finger along my arm, and asked if that was okay. I shivered and said yes. She nodded and asked if I minded doing these small things for her. I said I didn't mind at all, I was happy to help her, and she said I was doing a good job, and she liked that I did what I was told. I sort of blinked and stuttered at that. And then that was that.

I thought about her a lot the next few weeks, and then next time she was in town she came by my desk, asked me for something, and slipped me a note. It said, "I have something else that I need some help with outside of office hours. Meet me in the bar of the Hotel XXX at 7 o'clock Friday night. If you aren't interested, that's okay...but I hope you are."

So my heart was pounding in my throat all week, as I saw her around the office and she would nod at me with a little smile. But she never made mention of it, never even asked if I would show up. She left the office early Friday afternoon and gave me a little wicked glance, saying, "I hope you enjoy your Friday night," as she left but that was it.

I arrived at her hotel lobby at 7 pm, clean shaven and showered, dressed as best as I could as a kind of dorky 23 year old kid. She was there in the bar area at one of those couch/low table setups. She stood as I entered and she looked spectacular. She said, "how about a drink?" and motioned the bartender over.

I barely remember the conversation to be honest. I was so nervous and horny (and a little unsure where this was going) and she just had me in her power and we both knew it. We had a drink, and talked. Then she gave me a deep, slow, sexy smile and said something to the effect of: "I really appreciate that you've been taking such good care of me when I come by your office all this time. It takes a special kind of man to take care of a woman, you know? I think a man who serves a woman's every need, no matter how big or how small, is very sexy..."

I gulped and squeaked out something awkward. Then she said, "I have some other needs that I would really love for you to help me with. Would you be willing to help me with that?" I could only nod, and she laughed, and she said "Well, let's go up to my room then." She waved the waiter over and paid the bill, and up we went. The elevator ride was kind of awkward, I wasn't sure what to do, and she just stood there and sort of smirked at me. She was clearly in control.

When we got into the room Julie locked the door and drew the curtains. When she turned back around she came over to me and got very close, ran her hand through my hair, began to caress my arm and chest. She told me that for the next hour, I was to do whatever she told me, and that I was going to like it. She kindly told me that of course, if I really didn't like it, that I could say the word "Charity" (inside joke from work) and that was the safeword, and we would stop. I don't think I had realized it was going to go in this direction, and I felt so incredibly nervous and turned on. I wasn't sure how kinky she was going to get, but this felt very sexy and yet the unknown was slightly disconcerting.

Then Julie told me to take off all of my clothes. It felt so intimidating but so intense, to be undressing in front of her. She watched and nodded appreciatively, I guess I looked okay. I stood there naked in front of her, my erection throbbing. Then she told me to sit down, and that I was not to touch myself.

Then she began a simple striptease - not performative but teasing and businesslike. She took off her blouse and turned around to slide down her snug skirt. Julie stood in front of me in a black bra that showcased her spectacular breasts and a black thong that framed her incredible big ass, along with stockings and heels. She turned back to face me, standing in front of the bed.

Then she told me to crawl to her. My heart was pounding in my throat. I got down on the floor and crawled to her, and she told me to kiss my way up from her feet. I began to do so, her feet, her calves, her thighs. When I got to her pussy I could smell her damp wetness through her thong and I thought I was going to die. I kissed her pussy through her panties, and she slowly revolved, allowing me to kiss her ass cheeks, and then turned back facing me.

Then she guided me up, over her slightly soft belly, up to her tits, and she undid her bra, letting them out. There was this indelible moment then, when it went from tentative on my part to just driven, and somehow tasting her nipples did it, and I began to just devour and worship her. Julie moaned as I sucked on her stunning tits, grabbing my hair gently. I kissed her neck and then we kissed passionately, my cock pressed up against her. She guided me back down to her tits and I kept going, kissing her stomach, and back down to her pussy. She hooked her fingers into her thong and I helped her, sliding it down, and she laid back on the bed, spreading herself wide. She was magnificent, so incredibly sexy. She was trimmed but not shaven. I had been with a few women at that point, and had had a girlfriend for a few months in college, and the sex had been great. But Julie was just so open and confident, exposing herself to me so immediately and clearly, that it was shocking and sexy all in one.

I kissed along her thighs and worked my way up to her pussy. I teased a little along the edges and then dived in. Her pussy tasted incredible, and it was slick and wet with her excitement. I was experienced at that point, but not incredibly so, especially when it came to giving women oral. But she was good with directions - guiding me up and down; I knew where the clit was but she would help with pacing, tell me when to tongue the clit, when to slide back down for a break. It slowly built up and she came hard, clutching at my hair.

The whole time I was so incredibly horny, my cock sticking out and throbbing, but I barely thought about it, other than when it would whack into something. After her orgasm she sighed and paused, sat up and removed her stockings and heels, and then rolled over and raised onto her hands and knees, and ordered me to taste her from behind. I started to lick her from behind but the angle made it difficult, so I slid back down onto the floor and she scooted back. From behind and slightly below her I approached and began to tongue her from behind. I had never done that, and it was so incredible - licking her pussy from behind, my nose in her ass, and knowing my face was in that big beautiful ass of hers. Then Julie reached back and grabbed my hair and gently pulled me up, guiding me, and told me to eat her ass. I had never done that before and it was so dirty and so wrong but so sexy. Tentatively and first, and then firmer, I began to tongue her asshole. She was moaning and spreading her legs wider, and I was on the floor, approaching her from below. There was something so intense and hot about that and all of a sudden I knew I was going to cum, and hard. It was almost as she could tell because she reached back and grabbed my hair again and held me in there, tonguing her asshole, and I was mumbling and groaning and she was moaning and then all of a sudden, without even touching myself, I just exploded everywhere and moaned in a muffled way. She shuddered and made a deep sexy sigh herself, I think with a smaller orgasm.

She laughed and laughed, sexily, not meanly, and let go of me, and slowly rolled back onto the bed. She pulled me up next to her and gave me a deep, passionate kiss, licking her own juices off my face. My cock was still shuddering, with cum still leaking out. She said that it was okay, I deserved that, and that it was very very sexy that I had come just from pleasuring her. I was pretty embarrassed. But she assured me it was very hot and nothing to worry about. She said, "I think you must have really liked doing that to cum without me touching you...and that means we should spend a little more time on me. We're not going to have sex tonight, and I hope that is okay. It seems to me that you enjoyed that enough." I probably would have been disappointed but at the moment I was feeling just sort of embarrassed and catching my breath.

We took a little break after that, and then she brought me into the shower, and we washed each other and then before long she had me back licking her pussy and ass again. I stayed for another hour or so, with so much oral for her - she rode my face, standing, lots of different positions. It felt like a very sexy education in oral pleasure for women. She never reciprocated, she didn't touch my cock or suck it or anything. And no penetration, and I was never sure why, nor did I ask. I felt very intimidated, and just assumed she didn't want to. Of course once I left I went back home, my mind spinning, and I spent the rest of the night (well, and the next few weeks) masturbating furiously.

I was lucky enough that this happened a few more times over the next couple of months. Next time she came back into town and I saw her at the office, my heart skipped several beats. This time she just asked if I could bring some paperwork by her hotel, to meet her in the lobby. On that night and a couple of others, we had a couple more really intense oral sessions where I pleasured her for a couple of hours in a variety of positions. I didn't cum these times and she seemed to like that, to leave me so pent up. It was such a sexy tease, frustrating but also somehow so sexy. She very well understood - it was never using D/S language, but she would say that I was there for her pleasure, that it was all about her, and that her pleasure was my reward. And quite frankly, I agreed.

On the 4th occasion, I did not know this at the time, but it would be the last time. She seemed to know - and she really did it up. There was room service champagne, and she had an incredibly sexy lingerie outfit. This time she reciprocated the pleasure - per usual, I focused on her for a while. She was riding my face and getting close to cumming, when suddenly she leaned over and I felt her hair tickling my cock that was sticking into the air. Then I felt the most incredible feeling as her mouth enveloped my cock. I was already obviously pretty close, and I did not last long, but it was a stunning experience, as she took me in deeply and my face was buried in her pussy in a 69. I came explosively in her mouth as I devoured her pussy and we both moaned in pleasure. It was one of the most intense orgasms of my life. I asked her what happened, and she simply smiled and said, "you earned it...but don't expect that again. You're here for MY pleasure..." and I just nodded and said thank you.

We never even said a proper goodbye - I assumed this would keep happening, but after that visit Julie did not return to the office, and my supervisor reported in a staff meeting that we were done with that project for the client and that they would not likely be returning. I was shocked and disappointed - I didn't even have her phone number. I still think about her all the time, and she definitely carved some grooves into me that make me take so much pleasure in pleasuring a woman...ever since it is one of my greatest pleasures, to give women oral pleasure. Cumming hands-free while pleasuring a woman has only happened one other time since then, perhaps a story for another time.

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