Maggie at Work

I've been a very sexual person ever since I can remember. Even at the age of six I was fascinated with my erections and was often preoccupied with figuring out ways to show them to other people. I have many stories to tell but I thought I'd start off with one of my more daring ones. My parents owned a small business when I was growing up. They had about a dozen employees, pretty much all of them women. I worked there in my teenage years during the summer months and always enjoyed being around all these females. Mom and Dad would also go on work trips often throughout the year, to attend seminars here and there. I would usually tag along. Even though I spent most of the time in a hotel room then, it still beat going to school and I got to see many interesting places. At first I shared a hotel room with my parents. They'd get one with two beds. As I got older, they let me have my own room. Sometimes an employee from work would also come along, to help them at the seminar, and the girl would stay in her own room. Until one day...... One of these girls was Maggie. Well, I shouldn't call her a girl, because she was in her mid 30s and twice my age at the time. I really liked Maggie. She was always fun and confident. Maggie was kind of plump but I always found her beautiful. She was well proportioned, had an angelic face, and God was I fascinated by her big chest. I know she had been married for about a dozen years then and had a son around the age of 10. Maggie was also interesting in that she was kind of obsessed about collecting bras the way other people collect stamps or baseball cards. It became a running joke at the office for someone to ask her what bra she was wearing today, and Maggie was actually not shy about lifting up her shirt. This was a small business and things weren't as politically correct as they are today, so nobody cared. In fact, Maggie didn't even care when I was around, and naturally seeing her wonderful breasts nestling in a bra was a highlight for me. One week, when I was about 16, my parents and I had to travel halfway around the country to attend one of those seminars. They needed to take along some props and boards, and we therefore couldn't fly. I passed the time by watching some videos on the VCR we had installed in the van. Nobody was coming along with us this time, until the second day that is...... Maggie had come along two or three times before, and after the first day of this seminar my parents decided they needed her help again. She was on the next plane to where our seminar was. The only problem as it turned out was that our hotel was pretty much booked full. So my parents began thinking about having Maggie stay at another hotel, when she suggested that she could stay in my room, if it didn't make my parents or me uncomfortable. The room had two beds after all. Was I uncomfortable with that idea? Hell, no! Thankfully, my parents were fine with it as well, just as long I didn't feel embarrassed sharing a room with a woman. Was I embarrassed? Hell, no! So Maggie flew in at 9 am and went straight to the conference center. I was watching some daytime TV show in the hotel room while doing my homework, as usual. Then things got interesting...... The phone rang and it was my mother. Mom said that Maggie was on her way to the hotel for lunch and that I shouldn't be surprised if the door opened. Maggie was stopping by to drop off her bags and take a nap. No problem, Mom. Suddenly, my mind went into overdrive. I had been horny all day, but there were no laptops yet to watch porn, and I wasn't willing to sneak a Playboy in my bags that I had borrowed off a buddy. What if Maggie would catch me masturbating? She always seemed so cool, especially when she showed off her newest bra while I was around to get a good look, but might she snap and get angry? Might she tell my parents? Could I get into heaps of trouble? I almost forgot about the idea because I was so worried that Maggie catching me with my dick in my hand would go horrible wrong, and yet, at the end I still felt I could pull it off if I played my cards right. I stripped, jumped onto the bed, and began stroking my dick. The plan was for Maggie to open the door, walk in, and catch me like this. It was about a ten minute drive from the conference center back to the hotel room and I still had plenty of time to rethink my decision. But no, I figured if she was open minded enough to show off her bras, she should be open minded about this. If she wasn't, I'd just feign ignorance. After all, I was a 17 year old horny kid, and maybe I had forgotten already that my Mom called me to tell me Maggie was on the way. Next I found the channel with Baywatch and turned up the volume. That way, I wasn't going to hear Maggie open the door and walk in, and I'd have an excuse for why I was stroking my dick. Then it came. I almost came. I heard a key going into the lock and the door opening. I quickly turned my head to the TV and shut my eyes. "Oh my. I can come later if you want. Sorry for interrupting you." I heard Maggie say. I opened my eyes to see a big grin on her face. Then I quickly reached for the duvet and pretended to cover up. Oh, no, no. I'm terrible sorry. I hope I didn't embarrass you. "I understand. Boys your age have...... certain needs. But what about that big boner of yours?" Maggie still had a big grin on your face. Uhm, well, I could keep stroking it if you want. But what about you? "What do you mean?" Well, do you masturbate? "No, not really." Oh, I guess you and Peter have lots of...... fun time in the bedroom, then? I asked, now having a big grin of my own. "No." Her demeanor was changing. "Peter hasn't really touched me since our son was born. You know, that was ten years ago." Now I went for the Hail Mary. I asked Maggie why she didn't join me. I was half expecting her to freak out on me and call me a pervert...... "I couldn't. I don't want you to think less of me. Especially since you're still a minor. I wouldn't want to be the creepy woman taking advantage of a kid." Well, I didn't think I was a kid anymore at 18. Besides, I was the one making the suggestion, and I promised on everything that was holy and dear to me that I would never tell a soul, should Maggie decide to change her mind. With that, her big grin returned, and she started making her way to my bed. She began to strip down. In just a few seconds, she was down to her bra and her panties, and I had to slow down not to shoot my load then and there. Her big tits stuffed into one of those bras she always like to talk about. Her big panties that still showed off some of her dark pubic hair. Her big tummy, which yes, I wanted to kiss, caress, and do whatever else she might let me do. Maggie then took off her bra and panties, and holy fuck, that might have been the best moment in my life. Her tits were just as plump as I had imagined. Her pussy was beautifully hairy and inviting. Yes, I know, everybody shaves down to the skin these days, but to me a hairy, juicy pussy is a sign of a woman who is sexually mature and ready to fuck. I wouldn't want it any other way. I began to stroke again and she started rubbing that hairy pussy of hers. We were both kind of slow, uneasy about what to do. Then I asked her if I could start sucking on one of those beautiful, big, plump, juicy tits of hers? "Of course!" she said with another big smile. I buried my face in her chest. I licked and sucked her tits like my life depended on it. Meanwhile, I was stroking harder and her fingers went deeper and deeper into her pussy. Then I got an idea...... I quickly grabbed Maggie's masturbating hand and pulled it to my face. That looks delicious, I told her, as her eyes got big. Then I forced her went hand into my mouth, savored her sweet juices, and moaned loudly. Oh, good Lord, I need more of that! I exclaimed and jumped between her legs, before she even had a chance to respond. I already knew all about pussy licking, and I stuck my tongue deep into her sweet nectar. I loved the sensation of her juices on my taste buds, of her meaty lips against my tongue, and her furry pubes against my face. Her breathing became shorter and her moans louder and eventually she had a wonderful orgasm. Maggie then grabbed me by the shoulders and pulled me up. She began to kiss me deeply. Somehow, we both felt it was for the best not to go all the way, but she still kept grabbing my hips and pulling me against her as my throbbing cock was nestled between her folds. With all that had already happened and now this dry humping, it didn't take long for me to erupt. "Sweetie, I haven't felt this alive in years and years. But I hope I didn't take advantage of you." No, I reassured her. It had been my idea, and if anything, she had made me extremely happy. And as I said previously, this was just a one time event and I wouldn't tell anyone. It wasn't exactly a one time event. The seminar went on for two more days, and let's just say that Maggie never slept in her own bed, and both nights were her idea...... But nothing more happened after we returned home, which is fine. Maggie had still given me some unforgettable experiences in that hotel room. Besides, we both worked for the family business a few more years, and it wasn't unusual for me to press against her thick ass or grab those beautiful tits when we were in a room alone, and every once in a while she would actually turn around and passionately kiss me on the lips.