Natalie Ch. 01

Natalie had been a coworker of mine for about a year when it happened. It was the first time we had been sent out of town together.

I noticed Natalie the day she started. She reminded me of a girl I had a serious crush on in high school: short, about 5'2", brunette, and somewhat athletic. She has a cute shyness about her and an unpretentious way of dressing. That always appealed to me more than the skinny, boyish models or six foot tall amazonians that seem to appeal to the rest of the world.

We are both married, and I'm not the cheating type, so I never made a move. However, I always knew that if the opportunity presented itself, I would not be able to resist.

We arrived at the hotel at different times, but we had already agreed to go to dinner, so when she called me around 7:30, I went down to the lobby. She had changed a simple denim skirt that fell about three inches above her knees, a cotton top which she left unbuttoned to just above her bra, and a pair of strappy wedge sandals that made her legs and feet look great. Not the world's sexiest outfit, but until this point I had only seen her in much more conservative, business attire. Getting a peek at her soft b-cup breasts and more of her legs suddenly made this trip just a little more exciting. Still, I wasn't really expecting anything.

We drove downtown and walked around for a while before finding a nice looking place with a view of the city square. We split a bottle of wine and had a nice meal, talking about all sorts of things for more than two hours. During desert, the conversation shifted. She was having trouble with her husband. He was in a highly competitive law school program and wasn't doing well, so he spent almost 18 hours a day studying—even missing their anniversary for the second year running. She told me she wanted kids, but since she is already mid-30s, she was afraid she never would at this rate.

It was never vocalized, but I got the distinct impression that her needs weren't being met by her husband. Emboldened by the wine and the frank conversation, I started making little moves—leaving my hand on the table close to her, moving my leg so that her leg would brush mine now and then. Little, awkward moves made by someone who hasn't dated for over a decade.

She didn't shut me down, and after the first contact, she didn't stop brushing my leg with hers. When dinner was over, I took her gently by the small of her back as we walked back to the car. When I helped her into the car, she didn't bother to pull her skirt back down. While we drove back to the hotel, I had a hard time keeping my eyes on the road with her nearly bare legs next to me. It was clear she noticed my difficulty and was enjoying it.

I don't know what it was, maybe the wine, maybe something else, but Natalie had changed from the shy, reserved person I knew into a much bolder, overtly sexual woman.

My room was on an upper floor, but as if there were any doubt, she proclaimed her intentions by yanking me off the elevator on her floor. However, when we reached her room, neither of us was exactly sure what to do next. It was a suite with a large couch in the sitting area and a king bed and a nice bathroom. She walked over to the couch and sat, so I sat next to her and she swung her legs onto my knees.

I slipped her sandals off so I could start rubbing her feet. Starting with her toes, I slowly moved up her calves. She said, "Those shoes hurt my legs. Dig your fingers in." I obliged and massaged her calves very hard. She arched her back against the arm of the couch, emphasizing her perky breasts and flat stomach.

I started running my hands up her thighs, eventually grabbing both sides of her left leg with my hands. She parted her legs just a little to allow me to reach higher as I massaged her upper thigh. Eyes closed, she dropped her right leg to the floor and bent her left leg, allowing me to see the little, sheer black thong she was wearing. I took the opportunity to massage her bare ass.

Lifting her other leg, I grabbed both cheeks and pulled her towards me. Her skirt and shirt rode up, exposing her stomach to me. With one motion, I pulled her thong off to find something I didn't expect to find under her conservative clothing and shy demeanor.

She had just a small strip of short hair over otherwise completely bald lips. Never one to waste the opportunity to get close to a bald pussy, I began kissing the back of her legs, working my way down to her ass and began teasing her by brushing my lips and tongue lightly against her bare lips.

If there was any resistance to what we were doing left in Natalie, it was gone now as she let her legs fall open to give me full access. I decided to tease a little and make her want it before I gave it to her. I kissed all over the inside of her thighs, on the outside of her lips and on her pelvis, but never opening her up until finally she grabbed the back of my head and pushed my mouth directly over her clit. I obliged by pushing my tongue past her lips and tasted her for the first time.

Tasting a woman for the first time is a treat for me. I hear a lot of men don't like it, but I love it, and I resolved that her first orgasm with me should be from my tongue. With her hands still holding my head tight into her, I licked her for all I was worth. It didn't take long before she moaned and clenched her legs around my head in her first orgasm of the evening.

She released me and I moved up, planting kisses on her pelvis, navel, stomach, and still covered breasts on my way to her mouth. Reaching her soft lips, I gently parted them and she slid her tongue into my mouth briefly before pulling back and saying, "Let's go get cleaned up before the next act" with a mischievous little grin.

Standing up, I pulled my shirt off, kicked off my shoes and started pulling off my pants. Natalie paused on her way off the couch to give my cock a quick kiss before stripping off her remaining clothing and walking towards the bathroom.

I followed her, mesmerized by the swing of her tight, naked ass. As she bent over to turn on the water, I ran my hand over her ass, slipping my thumb into the crack and brushing her asshole lightly. She straightened and whispered up to me, "Make sure to clean that well" with the same mischievous grin she had given me earlier.

We climbed into the shower and she grabbed the soap and began rubbing my chest with the bar. It wasn't long before she started to clean my cock and balls with the soap. Her hands moved with confidence and tenderness. She spent much longer cleaning my cock than was absolutely necessary and I had to grab the walls to steady myself. After the water rinsed off the soap, she knelt down in front of me and took my cock into her mouth as she soaped up behind my scrotum and my ass. Her mouth was amazing. She sucked softly before pushing forward to take me down her throat. I didn't want to stop her, but I knew that if she made me come now, I would be useless.

She handed me the soap and turned around to stand up slowly, rubbing her ass up the front of my legs. She's so much shorter than me that her ass only just reached my cock, but she wiggled her ass as my cock bounced across her cheeks and giggled, "I'm ready for my cleaning."

I began to rub the bar of soap around her buttocks, working up lather before setting the soap aside and using my hands to scrub her crack, asshole, and pussy. I stroked her from clit to asshole several times before slowly sliding the tip of my finger into her cute little brown hold.

"So, you're after my asshole?" she asked.

"Yes."

"Just as well, I don't have any birth control, and I think I'd like a cock in my ass."

I still couldn't believe what was happening; I would never have thought I'd even talk to her about anything personal, and now I had my finger in her ass and she was asking me to fuck it.

We rinsed off and toweled the water off each other's bodies. My cock was rock hard at the thought of sliding it into her tight, virgin asshole and she paid special attention to it, taking it in her mouth and teasing my balls with her fingernails. I had to flinch away from her to avoid shooting my wad right then. The anticipation was definitely getting to me. She looked disappointed when I stopped her, but she knew what effect she was having on me, and she was clearly enjoying that power.

On the way to the bed, she stopped at her suitcase and pulled out a tube of lubricant saying, "I bought this so my husband could fuck my ass, but he thought it was gross. I don't know why I keep it with me all the time, but I'm glad I have it now."

"And so am I."

"Just one more thing I want you to do first—loosen up my asshole with that sweet tongue of yours." With that, she slid her finger down my jaw and into my mouth before standing on her toes and kissing me, hard. She grabbed the back of my neck to pull herself up, and I wrapped my arms around her and pulled her up into me, my cock pressing against her stomach.

I'm not sure how long the kiss lasted. I ran my hands across her firm, athletic ass and she wrapped her legs around me and pulled herself higher. My cock slipped down her pussy and under her ass. She smiled as she teased me my sliding back and forth across my cock.

I lowered her onto the floor and she turned around to kneel on the edge of the bed with her ass in the air. The thought of licking her ass made me stop to think for a moment, but the sight of that beautiful brown hole and the thought of my cock inside of it made me throw caution to the wind.

I lowered my face to her crack and spread her ass cheeks. After one quick lick between her pussy lips, I moved up and circled my tongue around her asshole. She jumped and squirmed a bit and moaned, "Don't stop." as I started to push my tongue inside her asshole. I felt her clench a little, so I slid two fingers into her pussy to try and loosen her up. With two fingers working in and out of her pussy and my thumb rubbing her clit, she loosened enough for me to slide the tip of my tongue into her asshole. "Use your finger." she breathed back to me as she rocked her hips back into me. With my other hand, I slid my index finder slowly into her tight hole. She took is easily, pushing her hips back onto my finger with a little squeal of pain. "Too much?" I asked her.

"No, it feels even better than I thought it would. Use some lube and fuck me with your fingers."

I dribbled a few drops out of the bottle onto my finger and pushed it back in. With the extra lubrication, it slid in easily, so after a few strokes, I slid in two fingers, very slowly. The second finger was harder for her to take, so I moved down and licked her clit to help her relax. Suddenly, and without any warning, she screamed out loud as an orgasm rocked her body. I grabbed her hips to keep my tongue on her clit as she shook for what must have been a full minute. Sometime during this, the two fingers in her ass managed to slide all the way in and I started slowly fucking her with them as her orgasm subsided. I could tell she had to rest for a while after that powerful and unexpected orgasm, so I paused for a few minutes and let her recover.

"I think I'm ready; lie on your back." she finally said, grabbing the lube off the bed. After stroking the lube onto my cock, she straddled me and guided my cock towards her asshole. With the tip of my cock pressed against her ass, she slowly backed onto it. After a bit of a painful moment for both of us, the head of my cock popped into her asshole. Just then, I looked up at her and saw her face contorted in the most exquisite expression of pleasure and pain I've ever seen.

It took her a few minutes to relax enough to move, so I just lay there watching her face shift from pain to pleasure. She bit her lower lip and smiled down at me as she started rocking her hips back and forth just a little, slowly driving my cock deeper and deeper into her ass. Eventually, she was sliding my cock nearly all the way out and then plunging back onto it.

Then, something amazing happened. She committed to taking my cock all the way into her ass and sat down on it with all the force she could muster. My cock must have hit her g-spot because she kept repeating "Oh, yes!" over and over every time she forced my cock deep into her ass. I had heard it could happen when fucking a woman in the ass, but I'd never seen it before.

The feeling was amazing. She had loosened considerably, but the sensation of my cock working in and out of her hot, little asshole was simply indescribable.

I couldn't take it anymore, and with her breasts swinging above me as she drove herself onto me; I came deep into her ass. She reacted by rocking back and drove me deeper as she, too exploded with one last orgasm before collapsing onto my chest, not bothering to pull my cock out of her.

After a few minutes just lying on top of me trying to catch her breath, she repeated over and over, "I had no idea, I had no idea..."

"You had no idea about what?"

"I had no idea a cock in my ass could make me come so hard."

With that, she slid off me and quickly went to sleep with one leg and arm still wrapped around me. Sleep for me wasn't far behind.