Naughty Gift Exchange Ch. 01

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.

Madison told me I would get my gift the night before my birthday and sure enough that morning on the way to work I received a picture from an unknown number. It showed a very curvy girl, wearing tiny panties. She was facing away from the camera which was positioned on the ground looking up and showing her giant ass cheeks spilling out of the thong. She held her hands over her big tits and her face was cut off but I got hard right away just looking at it and even more excited when I read her note, "I heard there is a naughty birthday boy who is looking to get smothered under this big ass?"

I looked at the picture again and again and reread the note at my desk before I responded. "Yes, thank you. I would like that very much."

My heart was beating fast and my cock was pushing a tent up in my pants. I waited for an answer but after some time put the phone away. I pulled it out immediately when I heard a buzz but it was an early birthday message from my Grandma. I told myself to get it together and carried on with my work but when my phone buzzed again I grabbed it right away. It was from her. "I know you will. Tell me your fantasy."

I got so horny thinking about this that I had to go to the bathroom and jack off. I felt guilty thinking so much about this girl, but Madison had insisted after all. I gave it a lot of thought and finally answered her, "I... would really like it if you made me beg to kiss your big ass."

The minutes that went by after sending this felt like hours but she finally answered, "Oh, I'll be having a subbie underneath me tonight? This will be fun."

I smiled, but my heart sped up and cock twitched when she followed up with, "I will be there at 8pm. Leave the door unlocked and kneel naked on the floor while you wait for me".

I told Madison that I'd made arrangements but left out the details. I asked if she was really ok with this and she texted back "Absolutely. Enjoy your fantasy on your birthday!" So I was feeling nervous and shy, but not guilty as I knelt in my living room, naked with my cock already hard in anticipation, with more than 10 minutes to go before 8pm.

I finally heard the sound of high heeled steps approaching in the hallway before my apartment door swung open. The door shut and with a few more clicks, my 'Mistress' was standing above me, looking down with a smirk. Even wearing an overcoat (with bare legs and heels) her generous curves were evident, but that was not the reason my jaw dropped. The girl standing above me with a clear air of superiority was Monica, one of our Office Assistants. I had stared at her from afar so many times, but had barely spoken a word to her.

"Surprised?" she asked, her smirk still present. I couldn't manage a response, my mouth dry, my mind trying to catch up with the implications.

"I know you've enjoyed watching this ass sway past often, can you imagine what it will be like to see it lowered onto your face?" she asked with a giggle. My cock got harder just with the suggestion, and as she moved closer I could see her panties up her coat I was breathing heavily in anticipation. Monica had the body of my dreams and here she was to fulfill my fantasy. And yet, while my cock throbbed, my thoughts was racing... Madison asked her to sit on my face? did the other girls know? would they find out?

I was snapped back to the beautiful girl in front of me when Monica kicked off her heels and thrust her bare sole in my face. "Maybe you should beg me first?" she taunted.

I had encouraged girlfriends to be dominant with me before, but I could feel the difference immediately with Monica. She knew she was superior and expected me to obey. I fell immediately into a subspace and started kissing the bottom of her foot gratefully.

"Please Monica... please please may I kiss your ass?"

Monica laughed down at me and finally pulled her foot away. "Look at you." she teased. "Such a desperate puppy. You've fantasized about this Puerto Rican ass and now you can almost taste it." With this she turned around and dropped the overcoast on my face. When I pulled it away I was staring up at Monica, now turned away from me, wearing lingerie that barely covered her giant ass. It was big, bouncy perfection.

I'm not sure I had ever been so horny. "Yes." I hissed. "Yes.... I am desperate... please may I kiss it Monica?"

She turned to look down at me over her shoulder and laughed, "Such an impatient boy." Then she paused and smirked, "Does Madison know how desperate you are?"

My mind flashed to my girlfriend and I blushed. "No... she.... errrr...."

"Never mind birthday boy." Monica giggled. "You can kiss me..." she paused, then pointed to the bottom of one ass cheek, "here."

I didn't hesitate, my heart pounding, cock throbbing. I sat up on my knees, and planted a kiss exactly where she told me to, my nose pushed into her flashy ass cheek. Monica giggled as she looked at me over her shoulder.

"Again." she commanded, and I obeyed gratefully. This carried on for some time as she pointed at different spots until she pointed her finger directly between her two ass cheeks. On my knees I lifted my head and pushed my face into her ass, my nose buried deep in her ass crack and kissed her thong. My lips did not quite reach her asshole, but I loved the feeling.

"Thank you Monica." I said without thinking.

"Mmm.." she said. "Lie down. On your back."

I was quickly lying down, naked on my floor, looking up at Monica's beautiful body. She allowed me to enjoy this view a while, then slowly peeled down her panties, revealing her shaved pussy with big inviting lips. I imagined what it would be like to fuck her, and remembered Jack, the cocky guy from my office, saying Monica was one of his conquests. Monica smacked her ass, "You want this in your face birthday boy?"

"God yes!" I said, surprising myself with the urgency in my voice. "Please please Monica?"

Monica laughed as she turned so her giant bare ass was facing me then slowly lowered herself. She stopped just above my face, her big ass cheeks spread so I could see her asshole presented to me. I begged more and she giggled again, "Oh my, imagine what the girls in the office would say if they saw you like this?" She lowered herself onto my face, slowly, until I was smothered under her big ass, my nose deep in her ass crack. I kissed her ass crack until I started gasping for air. She lifted for a moment but as soon as I took a deep breath she was on me again. "That's a good boy, but use your tongue."I immediately pushed my tongue up into Monica's asshole and she moaned until she let me breathe again.

"Much better." she said her ass just above me. I craned my neck and rimmed her more. "Mmmmm... all the boys love my ass, but they always wanted to fuck me from behind, or even stick their cocks in it. Nice to have someone who is grateful just to kiss it." I felt her juices drip on my chin as she smothered my face again and I tongued her asshole.

My cock twitched at the intensity of the stimulation and Monica's teasing and she giggled more. "Well... since it's your birthday, perhaps I can help you out a little."

Burying me in her fleshy ass again, she used two fingers to wrap around my cock and slowly stroked up and down. I could feel the precum oozing and knew I wouldn't last long. When she lifted for a moment I thanked her and she said simply "Cum for me."

Almost immediately I did, shooting high as she continued stroking slowly. It felt amazing as I continued to kiss her ass crack gratefully. When I finished cumming Monica stood and looked down at me, still smirking.

"Happy Birthday." she said softly. "Why don't you lie there and think about what you've done while I get dressed?" I watched this Goddess put her panties, then put on and button her overcoat. Before I knew it she had her shoes on, bent to give me a soft kiss goodbye and was gone.

I dozed off there, exhausted from the excitement after all the anticipation but maybe 15 minutes later, I heard the door open again. Madison's voice called my name and I answered with a croak in my voice. She walked in to see me naked on the floor. Unshowered, I was still sticky with my own cum and Monica's juices, so felt very self-conscious when Madison snuggled up next to me and gave me a tender kiss on the lips that had kissed her friend Monica's asshole again and again.

"Did you have a good time birthday boy?" she asked sweetly.

"I did... thank you Madison. You're the best. You really made it special."

"Of course!' she answered earnestly. Then she added with a more mischievous tone, "My birthday is only a few weeks away... I can't wait to see what you get me!"