I've always been attracted to curvier girls, but there was something about Madison that drew me to her. Madison is one of a small group of young female Assistants on my floor at the office. They are all attractive and stood out in an office made up almost exclusively of male executives. The girl I first noticed, and always caught my eye was Monica, who had big tits and a huge ass she shows off proudly like a Latina Christina Hendricks. She had everyone's attention though and never seemed to notice me. There is an Asian girl who is pretty curvy for her petite body petite body, but she wears a big diamond on her ring finger.
Madison is the most fun and flirty. She has Strawberry blonde hair, very white skin, freckles and is very slim and fit. She works out every day, so she has a perky, tight ass. Her tits are small, but she has a big personality.
Despite being 23, I didn't actually have a lot of experience with women, and would have considered a girl like Madison out of my league even a year ago at college, but now I was an Analyst at a prestigious Private Equity firm, and that gave me confidence. I had to work long hours so I naturally was interested in the girls I saw regularly at the office, especially Madison. She seemed to like me, but then again, she was nice to everyone, always with a big smile.
I wanted to ask her out, but I was still a bit hesitant,so I asked around about her with guys who had been around the office longer. They confirmed everyone liked her, but I also learned she had dated a few guys on my floor. This gave me a little pause, but also more confidence she might say yes. I asked her out to dinner and she gave me a big smile and said she'd love that.
I took her to a fancy restaurant, and I fell for her hard. She was so easy going and comfortable, more extroverted and confident than me, but always feminine. I was grateful when she agreed to see me again.
We went out on a few dates before I kissed her for the first time and we ended up fucking that night. She was clearly more confident and experienced than I was, but never made me feel awkward. I felt like I had won a lottery when she was still willing to see me after that, and I tried to learn what she really loved. She especially appreciated when I went down on her, and our habit became her straddling my face soon after we were alone.
I found it so hot to have her sit on me like this. I have a fetish for facesitting and even though Madison was very slim, I loved it every time.
As an 18 year old virgin, I actually had a girl sit on my face before I ever got to fuck a girl. At my prom, I struck out with my first choices for a date, and ended up taking a girl who was a little chunky. I thought I'd have a good shot at fucking her, but she would only let me do what she wanted, and what she wanted that night was for me to lick her ass. It was so exciting to see her bare ass lower on my face. I had never been so excited as when I was smothered by her big ass and I tried hard to lick her deep the way she told me to. When I had pleased her enough she jacked me off, and we did the same a few times that summer before I got to fuck her.
I haven't had many girls since then, but I have always tried to relive the experience, and with Madison, I was close. I would lick her pussy to orgasm every time we had sex, almost always before any other activities. I even convinced her to let me lick her ass a couple of times, and encouraged her to tease me that I had to do it right before I was allowed any other privileges.
At the office we kept our relationship discrete, but over the next couple of months we would see each other a few times each week. Nobody knew I was dating her which created an awkward moment. I was out to lunch with my manager, Bob, and Jack, a Senior Associate with the firm whom Bob is pals with. The Senior Associate, who is a big, cocky guy, started locker room talk about his many conquests. He bragged he had fucked a couple of girls from our floor, then surprised me by bringing up Madison.
"You know who is a real nice piece of ass is that Madison." he said, speaking to my manager as I listened. "I hear she fucks like a wildcat." He paused, clearly imagining her and added, "I should really tap that."
He moved on to talk about other girls, but I kept playing that back in my mind, and jacked off thinking about it when I got home. After I jacked off though, I felt anxious and called Madison. I told her I loved her, the first time I had said that, and she told me how sweet I was.
I had never had a serious girlfriend and decided I should make sure I committed to being a great boyfriend. I bought her flowers and started to read online about how to be the best partner. I started to closely follow an influencer who looked a lot like Madison, and the advice she emphasized more than anything was to 'communicate often and openly'. I made sure Madison knew how great I thought she was and asked her if we were exclusive. Madison looked a little surprised but said simply, "Sure, we can try that."
We continued seeing each other for another month and my birthday was coming up. Madison was sweet and said she wanted to get me something nice but didn't have much money. I told her I could take her out for my birthday but that only made her more frustrated.
One night I fell asleep after we fucked and she picked up my laptop to play a game only to find porn on it. She was not surprised to see I was into facesitting, but when I woke up she told me she didn't know I was into 'fat' girls.
I was so embarrassed she had seen this, but I couldn't help defend it a little. The girls weren't 'fat' I said, just thick. She said I must miss being with a thick girl. She didn't sound jealous at all, but I assured her I didn't miss it at all...this was just a fantasy. I hoped it would all be forgotten, but the next day she said she had a great idea. For my birthday she would get a fat girl to sit on my face and fulfill my fantasy. I was inclined to defend again that I wasn't into 'fat' girls, but instead told her I didn't need that gift at all, that she was all I wanted. To my surprise Madison became very insistent. "Let me get this for you, I really want to get you something special." I could never say no to Madison, so I agreed, even if I was unsure how it would play out.
